CN111886223A

CN111886223A - Organic compound, light-emitting element, light-emitting device, electronic device, and lighting device

Info

Publication number: CN111886223A
Application number: CN201980018238.8A
Authority: CN
Inventors: 门间裕史; 铃木宏记; 长坂显; 铃木恒徳; 桥本直明; 泷田悠介; 奥山拓梦; 濑尾哲史
Original assignee: Semiconductor Energy Laboratory Co Ltd
Current assignee: Semiconductor Energy Laboratory Co Ltd
Priority date: 2018-03-09
Filing date: 2019-03-04
Publication date: 2020-11-03
Also published as: WO2019171233A1; KR20200130409A; JPWO2019171233A1; JP7282737B2

Abstract

The present invention provides a novel organic compound. Further, a novel organic compound having a hole-transporting property is provided. In addition, a novel hole transport material is provided. In addition, a novel light-emitting element is provided. Further, a light-emitting element having excellent light-emitting efficiency is provided. Further, a light-emitting element having a long life is provided. Further, a light-emitting element with low driving voltage is provided. The present invention provides an organic compound in which any one of a benzocarbazole skeleton, a dibenzocarbazole skeleton and a triphenylcarbazole skeleton is bonded to any one of a carbazole skeleton, a benzocarbazole skeleton, a dibenzocarbazole skeleton and a triphenylcarbazole skeleton at naphthalene-1, 4-diyl or naphthalene-1, 5-diyl. Note that these skeletons or groups may also each include a substituent.

Description

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

Technical Field

One embodiment of the present invention relates to an organic compound, a light-emitting element, a display module, an illumination module, a display device, a light-emitting device, an electronic device, and an illumination device. Note that 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 manufacturing method. Alternatively, one embodiment of the present invention relates to a program (process), a machine (machine), a product (manufacture), or a composition (machine). Therefore, 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 storage device, an imaging device, driving methods thereof, and manufacturing methods thereof can be given.

Background

Light-emitting elements (organic EL elements) using organic compounds and utilizing Electroluminescence (EL) are actively put into practical use. In the basic structure of these light-emitting elements, an organic compound layer (EL layer) containing a light-emitting material is interposed between a pair of electrodes. By applying a voltage to the element, carriers are injected, and light emission from the light-emitting material can be obtained by utilizing the recombination energy of the carriers.

Since such a light-emitting element is a self-light-emitting type light-emitting element, there are advantages such as higher visibility, no need for a backlight, and the like when used for a pixel of a display device, compared with a liquid crystal. Therefore, the light-emitting element is suitable for a flat panel display element. In addition, a display using such a light emitting element can be manufactured to be thin and light, which is also a great advantage. Further, a very high speed response is one of the characteristics of the light emitting element.

Since the light-emitting layers of such a light-emitting element can be formed continuously in two dimensions, surface light emission can be obtained. This is a feature that is difficult to obtain in a point light source represented by an incandescent lamp or an LED or a line light source represented by a fluorescent lamp, and therefore, the light emitting element has high utility value as a surface light source applicable to illumination or the like.

As described above, although a display or a lighting device using a light-emitting element is suitably used for various electronic devices, research and development of a light-emitting element having higher efficiency and longer life is being actively pursued.

Patent document 1 discloses a substance having a pyrene skeleton including a plurality of carbazolyl groups having a condensed ring structure.

The characteristics of the light emitting element are remarkably improved, but it is not enough to meet the high demands for various characteristics such as light emitting efficiency and durability. For this reason, development of new materials is required.

[ Prior Art document ]

[ patent document ]

[ patent document 1] Japanese patent application laid-open No. 2010-195708

Disclosure of Invention

Technical problem to be solved by the invention

Accordingly, an object of one embodiment of the present invention is to provide a novel organic compound. Another object of another embodiment of the present invention is to provide a novel organic compound having a hole-transporting property. It is another object of the present invention to provide a novel hole transport material. Another object of another embodiment of the present invention is to provide a novel light-emitting element. Another object of the present invention is to provide a light-emitting element having excellent light-emitting efficiency. Another object of the present invention is to provide a light-emitting element having a long lifetime. Another object of the present invention is to provide a light-emitting element with low driving voltage.

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

The present invention can achieve any of the above objects.

Means for solving the problems

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

[ chemical formula 1]

A-L-A (G1)

Note that, in the above general formula (G1), L represents a substituted or unsubstituted naphthalene-1, 4-diyl group or a substituted or unsubstituted naphthalene-1, 5-diyl group. Further, a represents a group represented by the following general formula (gA), and B represents a group represented by the following general formula (gB).

[ chemical formula 2]

Note that, in the above general formula (gA), Ar¹Represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. In addition, in R¹To R⁷In, R¹And R²、R⁴And R⁵、R⁵And R⁶And R⁶And R⁷At least one group of (b) is fused to form a benzene ring, and the others independently represent any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

In the above general formula (gB), Ar²Represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. In addition, R¹¹To R¹⁷Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. Note that R¹¹And R¹²、R¹⁴And R¹⁵、R¹⁵And R¹⁶And R¹⁶And R¹⁷They may also be fused to form a benzene ring.

Another embodiment of the present invention is an organic compound having the above structure, wherein L is represented by the following general formula (gL-1).

[ chemical formula 3]

Note that, in the above general formula (gL-1), R⁴¹To R⁴⁶Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring.

Another embodiment of the present invention is an organic compound having the above structure, wherein L is represented by the following general formula (gL-2).

[ chemical formula 4]

Note that, in the above general formula (gL-2), R⁵¹To R⁵⁶Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring.

Another mode of the present invention is an organic compound having the above structure, wherein in the group represented by the general formula (gA), R is⁴And R⁵、R⁵And R⁶And R⁶And R⁷At least one group of (b) is fused to form a benzene ring.

Another mode of the present invention is an organic compound having the above structure, wherein in the group represented by the general formula (gA), R is⁴And R⁵And R⁶And R⁷At least one group of (b) is fused to form a benzene ring.

Another embodiment of the present invention is an organic compound having the above structure, wherein the group represented by the general formula (gA) is a group represented by the following general formula (gA-1).

[ chemical formula 5]

Note that, in the above general formula (gA-1), Ar¹Represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. In addition, R¹To R⁵And R²¹To R²⁴Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

Another embodiment of the present invention is an organic compound having the above structure, wherein the group represented by the general formula (gA) is a group represented by the following general formula (gA-2).

[ chemical formula 6]

Note that, in the above general formula (gA-2), Ar¹Represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. In addition, R¹To R³、R⁶、R⁷And R²⁵To R²⁸Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

Another embodiment of the present invention is an organic compound having the above structure, wherein the group represented by the general formula (gA) is a group represented by the following general formula (gA-3).

[ chemical formula 7]

Note that, in the above general formula (gA-3), Ar¹Represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. In addition, R¹To R³And R³¹To R³⁸Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

Another embodiment of the present invention is an organic compound having the above structure, wherein Ar is¹Is phenyl.

Another embodiment of the present invention is an organic compound having the above structure, wherein the group represented by the general formula (gA) and the group represented by the general formula (gB) have the same structure.

Another embodiment of the present invention is an organic compound having the above structure, wherein the group represented by the general formula (gB) is a group represented by the following general formula (gB-1).

[ chemical formula 8]

Note that, in the above general formula (gB), Ar²Represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. In addition, R¹¹To R¹⁷Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

Another embodiment of the present invention is an organic compound having the above structure, wherein Ar is²Is phenyl.

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

[ chemical formula 9]

Note that, in the above general formula (G2), Ar¹And Ar²Each independently represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. In addition, in R¹To R⁷In, R¹And R²、R⁴And R⁵、R⁵And R⁶And R⁶And R⁷At least one group of (b) is fused to form a benzene ring, and the others independently represent any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. In addition, in R¹¹To R¹⁷In, R¹¹And R¹²、R¹⁴And R¹⁵、R¹⁵And R¹⁶And R¹⁶And R¹⁷Or may be fused to form a benzene ring, and the remainder independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atomsOne. In addition, R⁴¹To R⁴⁶Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring.

Another embodiment of the present invention is an organic compound having the structure described above, wherein R is⁴And R⁵And R¹⁴And R¹⁵The groups of (a) are fused to form a benzene ring.

Another embodiment of the present invention is an organic compound having the structure described above, wherein R is⁶And R⁷And R¹⁶And R¹⁷The groups of (a) are fused to form a benzene ring.

Another embodiment of the present invention is an organic compound having the above structure, wherein Ar is¹And Ar²Is phenyl.

Another embodiment of the present invention is a material for a light-emitting element including the organic compound having the above structure.

Another embodiment of the present invention is a light-emitting element including the organic compound having the above structure.

Another embodiment of the present invention is a light-emitting element including the organic compound having the above-described structure between an anode and a light-emitting layer.

Another embodiment of the present invention is a light-emitting element including the organic compound having the above structure in a light-emitting layer.

Another embodiment of the present invention is a light-emitting device including the light-emitting element having the above structure and a transistor or a substrate.

Another embodiment of the present invention is an electronic device including the light-emitting device, a sensor, an operation button, a speaker, or a microphone.

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

In addition, a light-emitting device in this specification includes an image display device using a light-emitting element. In addition, the light-emitting device may further include the following modules: a module in which a light emitting element is mounted with a connector such as an anisotropic conductive film or TCP (Tape carrier package); a module of a printed circuit board is arranged at the end part of the TCP; or a module in which an IC (integrated circuit) is directly mounted on a light-emitting element by a COG (Chip on glass) method. Further, the lighting device and the like may include a light-emitting device.

Effects of the invention

One embodiment of the present invention can provide a novel organic compound. Another embodiment of the present invention can provide a novel organic compound having a hole-transporting property. Another aspect of the present invention can provide a novel hole transport material. A novel light emitting element can be provided. Further, a light-emitting element having a long life can be provided. Further, a light-emitting element with excellent light-emitting efficiency can be provided.

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

Note that the description of these effects does not hinder the existence of other effects. In addition, one embodiment of the present invention does not necessarily have all of the above effects. Further, effects other than these effects are obvious from the descriptions of the specification, the drawings, the claims, and the like, and the effects other than these effects can be extracted from the descriptions of the specification, the drawings, the claims, and the like.

Brief description of the drawings

Fig. 1A to 1C are schematic views of a light-emitting element.

Fig. 2A and 2B are schematic diagrams of an active matrix light-emitting device.

Fig. 3A and 3B are schematic diagrams of an active matrix light-emitting device.

FIG. 4 is a schematic view of an active matrix light-emitting device.

Fig. 5A and 5B are schematic diagrams of a passive matrix light-emitting device.

Fig. 6A and 6B show diagrams of the lighting device.

Fig. 7A, 7B1, 7B2, and 7C illustrate diagrams of an electronic device.

Fig. 8A to 8C show diagrams of electronic apparatuses.

Fig. 9 shows a view of the lighting device.

Fig. 10 shows a view of the lighting device.

Fig. 11 is a diagram showing an in-vehicle display device and an illumination device.

Fig. 12A and 12B show diagrams of an electronic apparatus.

Fig. 13A to 13C show diagrams of an electronic apparatus.

[ FIG. 14A and FIG. 14B]Of PaBC2N¹H NMR spectrum.

FIG. 15 shows an absorption spectrum and an emission spectrum of a solution of PaBC 2N.

FIG. 16 shows an absorption spectrum and an emission spectrum of a thin film of PaBC 2N.

[ FIG. 17A and FIG. 17B]Of PacDBC2N¹H NMR spectrum.

FIG. 18 shows an absorption spectrum and an emission spectrum of a solution of PacDBC 2N.

FIG. 19 shows an absorption spectrum and an emission spectrum of a thin film of PacDBC 2N.

[ FIGS. 20A and 20B]Of PcBC2N¹H NMR spectrum.

FIG. 21 shows an absorption spectrum and an emission spectrum of a solution of PcBC 2N.

FIG. 22 shows an absorption spectrum and an emission spectrum of a thin film of PcBC 2N.

[ FIGS. 23A and 23B]Of PCNPaBC¹H NMR spectrum.

FIG. 24 shows an absorption spectrum and an emission spectrum of a PCNPaBC solution.

FIG. 25 shows an absorption spectrum and an emission spectrum of a thin film of PCNPaBC.

[ FIG. 26A and FIG. 26B]10- [4- (9-phenylcarbazol-3-yl) -1-naphthyl]Benzo [ c ]]Of carbazoles¹H NMR spectrum.

[ FIGS. 27A and 27B]Of PCNPcBC¹H NMR spectrum.

FIG. 28 shows an absorption spectrum and an emission spectrum of a PCNPcBC solution.

FIG. 29 shows an absorption spectrum and an emission spectrum of a thin film of PCNPcBC.

[ FIG. 30A and FIG. 30B]10- [5- (9-phenyl) phenylCarbazol-3-yl) -1-naphthyl]Benzo [ c ]]Of carbazoles¹H NMR spectrum.

[ FIG. 31A and FIG. 31B]Of 1, 5PCNPcBC¹H NMR spectrum.

FIG. 32 shows absorption and emission spectra of a solution of 1, 5 PCNPcBC.

FIG. 33 shows absorption spectrum and emission spectrum of a thin film of 1, 5 PCNPcBC.

Fig. 34 shows luminance-current density characteristics of the light-emitting element 1 and the comparative light-emitting element 1.

Fig. 35 shows current efficiency-luminance characteristics of the light-emitting element 1 and the comparative light-emitting element 1.

Fig. 36 shows luminance-voltage characteristics of the light-emitting element 1 and the comparative light-emitting element 1.

Fig. 37 shows current-voltage characteristics of the light-emitting element 1 and the comparative light-emitting element 1.

Fig. 38 shows external quantum efficiency-luminance characteristics of the light-emitting element 1 and the comparative light-emitting element 1.

Fig. 39 shows emission spectra of the light-emitting element 1 and the comparative light-emitting element 1.

Fig. 40 shows luminance-current density characteristics of the light-emitting element 2 and the comparative light-emitting element 2.

Fig. 41 shows current efficiency-luminance characteristics of the light-emitting element 2 and the comparative light-emitting element 2.

Fig. 42 shows luminance-voltage characteristics of the light-emitting element 2 and the comparative light-emitting element 2.

Fig. 43 shows current-voltage characteristics of the light-emitting element 2 and the comparative light-emitting element 2.

Fig. 44 shows external quantum efficiency-luminance characteristics of the light-emitting element 2 and the comparative light-emitting element 2.

Fig. 45 shows emission spectra of the light-emitting element 2 and the comparative light-emitting element 2.

Fig. 46 shows normalized luminance-time change characteristics of the light-emitting element 2 and the comparative light-emitting element 2.

Fig. 47 shows luminance-current density characteristics of the light-emitting element 3 and the comparative light-emitting element 3.

Fig. 48 shows current efficiency-luminance characteristics of the light-emitting element 3 and the comparative light-emitting element 3.

Fig. 49 shows luminance-voltage characteristics of the light-emitting element 3 and the comparative light-emitting element 3.

Fig. 50 shows current-voltage characteristics of the light-emitting element 3 and the comparative light-emitting element 3.

Fig. 51 shows external quantum efficiency-luminance characteristics of the light-emitting element 3 and the comparative light-emitting element 3.

Fig. 52 shows emission spectra of the light-emitting element 3 and the comparative light-emitting element 3.

Fig. 53 shows luminance-current density characteristics of the light-emitting element 4 and the comparative light-emitting element 4.

Fig. 54 shows current efficiency-luminance characteristics of the light-emitting element 4 and the comparative light-emitting element 4.

Fig. 55 shows luminance-voltage characteristics of the light-emitting element 4 and the comparative light-emitting element 4.

Fig. 56 shows current-voltage characteristics of the light-emitting element 4 and the comparative light-emitting element 4.

Fig. 57 shows external quantum efficiency-luminance characteristics of the light-emitting element 4 and the comparative light-emitting element 4.

Fig. 58 shows emission spectra of the light-emitting element 4 and the comparative light-emitting element 4.

Fig. 59 shows normalized luminance-time change characteristics of the light-emitting element 4 and the comparative light-emitting element 4.

[ FIG. 60 ]]Of PbBC2N¹H NMR spectrum.

FIG. 61 shows an absorption spectrum and an emission spectrum of a solution of PbBC 2N.

FIG. 62 shows an absorption spectrum and an emission spectrum of a thin film of PbBC 2N.

Fig. 63 shows luminance-current density characteristics of the light-emitting element 5.

Fig. 64 shows current efficiency-luminance characteristics of the light-emitting element 5.

Fig. 65 shows luminance-voltage characteristics of the light-emitting element 5.

Fig. 66 shows current-voltage characteristics of the light-emitting element 5.

Fig. 67 shows external quantum efficiency-luminance characteristics of the light-emitting element 5.

Fig. 68 shows an emission spectrum of the light-emitting element 5.

Modes for carrying out the invention

Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and those skilled in the art can easily understand that the mode and details thereof can be changed into various forms without departing from the spirit and 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)

One embodiment of the present invention is an organic compound in which any one of a benzocarbazole skeleton, a dibenzocarbazole skeleton, and a triphenylcarbazole skeleton is bonded to any one of the carbazole skeleton, the benzocarbazole skeleton, the dibenzocarbazole skeleton, and the triphenylcarbazole skeleton at naphthalene-1, 4-diyl or naphthalene-1, 5-diyl. These skeletons or groups may also each include substituents.

The organic compound having such a structure, which is one embodiment of the present invention, is a material very suitable for a material constituting a hole injection layer, a material constituting a hole transport layer, and a host material of a light-emitting layer of a light-emitting element, and has excellent hole-transporting properties. Further, the organic compound according to one embodiment of the present invention, in which the substituent does not include a polyacene skeleton, can be suitably used as a material constituting the electron blocking layer, and contributes to improvement of efficiency and life of the light-emitting element.

The organic compound may be represented by the following general formula (G1).

[ chemical formula 10]

A-L-B (G1)

Note that, in the above general formula (G1), L represents a substituted or unsubstituted naphthalene-1, 4-diyl group or a substituted or unsubstituted naphthalene-1, 5-diyl group. L in the above general formula (G1) may be represented by the following general formula (gL-1) or (gL-2).

[ chemical formula 11]

Note that, in the above general formula (gL-1), R⁴¹To R⁴⁶Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and the number of carbon atoms forming a ring6 to 13, or a substituted or unsubstituted aryl group.

[ chemical formula 12]

In the organic compound represented by the above general formula (G1), when L represents a substituted or unsubstituted naphthalene-1, 4-diyl group, i.e., a group represented by the above general formula (gL-1), it is preferable because it is easy to obtain a raw material, its synthesis is simple, and its reduction potential is high.

In the organic compound represented by the above general formula (G1), when L represents a substituted or unsubstituted naphthalene-1, 5-diyl group, i.e., a group represented by the above general formula (gL-2), it is preferable because it is easy to obtain a raw material, its synthesis is simple, and its reduction potential is low.

In the general formula (G1), a represents a group represented by the following general formula (gA) and B represents a group represented by the following general formula (gB).

[ chemical formula 13]

In addition, the compound represented by the general formula (gA)In the group (A) of (B), R⁴And R⁵、R⁵And R⁶And R⁶And R⁷At least one group of (a) is preferably fused to form a benzene ring.

In the presence of R⁴And R⁵And R⁶And R⁷Any of the above groups is preferably fused to form a benzene ring structure because the reduction resistance is high.

In the organic compound represented by the general formula (G1), the group represented by the general formula (gA) is preferably a group represented by the following general formula (gA-1). A light-emitting element using the organic compound can have high light-emitting efficiency.

[ chemical formula 14]

In the organic compound represented by the general formula (G1), the group represented by the general formula (gA) is preferably a group represented by the following general formula (gA-2). A light-emitting element using the organic compound can have a long life.

[ chemical formula 15]

Note that, in the above general formula (gA-2), Ar¹Represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. In addition, R¹To R³、R⁶、R⁷And R²⁵To R²⁸Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted alkyl group having 6 to 25 carbon atomsAny of substituted aryl groups.

In addition, in the organic compound represented by the general formula (G1), when the group represented by the general formula (gA) is a group represented by the following general formula (gA-3), the thermal properties are high, which is preferable.

[ chemical formula 16]

In addition, in the groups represented by (gA), (gA-1) to (gA-3) above, when Ar is¹The phenyl group is preferred because it can be easily synthesized and has good sublimability.

In the organic compound represented by the general formula (G1), the group represented by the general formula (gB) is preferably a group represented by the following general formula (gB-1).

[ chemical formula 17]

Note that, in the above general formula (gB), Ar²Representing the formation of a ringA substituted or unsubstituted aryl group having 6 to 13 carbon atoms. In addition, R¹¹To R¹⁷Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

In addition, in the groups represented by (gB) and (gB-1), when Ar is²The phenyl group is preferred because it can be easily synthesized and has good sublimability.

In the organic compound represented by the above general formula (G1), when the group represented by the general formula (gA) and the group represented by the general formula (gB) have the same structure, the synthesis is simpler, and the yield and purity are improved, which is preferable.

The organic compound according to one embodiment of the present invention may be represented by the following general formula (G2).

[ chemical formula 18]

Note that, in the above general formula (G2), Ar¹And Ar²Each independently represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. Note that when they are all phenyl groups, the synthesis is simple and the sublimability is good, so that they are preferable.

In addition, in R¹To R⁷In, R¹And R²、R⁴And R⁵、R⁵And R⁶And R⁶And R⁷At least one group of (b) is fused to form a benzene ring, and the others independently represent any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

In addition, R¹¹To R¹⁷Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. Wherein R is¹¹And R¹²、R¹⁴And R¹⁵、R¹⁵And R¹⁶And R¹⁶And R¹⁷They may also be fused to form a benzene ring.

In addition, R⁴¹To R⁴⁶Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring.

In the above general formula (G2), R is used⁴And R⁵And R¹⁴And R¹⁵The light-emitting element of the organic compound in which each group is condensed to form a benzene ring is preferable because it has a long life.

In the above general formula (G2), R is used⁶And R⁷And R¹⁶And R¹⁷The light-emitting element of the organic compound in which each group is condensed to form a benzene ring is preferable because it can have high efficiency.

R¹To R⁷、R¹¹To R¹⁷、R²¹To R²⁴、R²⁵To R²⁸And R³¹To R³⁸Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. Examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, and a hexyl group. Examples of the cycloalkyl group having 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. Examples of the substituted or unsubstituted aryl group having 6 to 25 carbon atoms include a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, an anthryl group, a triphenylene group, a fluorenyl group, a 9, 9-diphenylfluorenyl group, and a 9,9' -spirobifluorenyl group. Note that in order to suppress the occurrence of electron-transporting property, it is preferable to use a group excluding 3 or more rings of polyacene among the above groups.

Further, in the case where the above-mentioned substituted or unsubstituted aryl group having 6 to 25 carbon atoms has a substituent, as the substituent, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 13 carbon atoms may be used. Specific examples thereof include methyl, ethyl, propyl, isopropyl, tert-butyl, hexyl, cyclopropyl, cyclohexyl, phenyl, tolyl, naphthyl, and biphenyl groups.

As for R¹To R⁷、R¹¹To R¹⁷、R²¹To R²⁴、R²⁵To R²⁸And R³¹To R³⁸Specific examples of the substituent(s) of (c) include the following groups.

[ chemical formula 19]

R⁴¹To R⁴⁶And R⁵¹To R⁵⁶Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring, and specifically, examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, and the like, examples of the cycloalkyl group having 3 to 6 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like, and examples of the substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring include a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, an anthryl group, a fluorenyl group, and the.

Further, in the case where a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring has a substituent, as the substituent, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 13 carbon atoms can be used. Specific examples thereof include methyl, ethyl, propyl, isopropyl, tert-butyl, hexyl, cyclopropyl, cyclohexyl, phenyl, tolyl, naphthyl and biphenyl groups.

As for R⁴¹To R⁴⁶And R⁵¹To R⁵⁶Specific examples of the substituent(s) of (c) include the following groups.

[ chemical formula 20]

In addition, Ar¹And Ar²Each independently represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, and specific examples thereof include a phenyl group, a naphthyl group, a biphenyl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a tert-butylphenyl group, a tolyl group, a trimethylphenyl group and the like.

As for Ar¹And Ar²Specific examples of the substituent(s) of (c) include the following groups.

[ chemical formula 21]

Specific examples of the organic compound represented by the above general formula (G1) are shown below.

[ chemical formula 22]

[ chemical formula 23]

[ chemical formula 24]

[ chemical formula 25]

[ chemical formula 26]

[ chemical formula 27]

[ chemical formula 28]

[ chemical formula 29]

[ chemical formula 30]

[ chemical formula 31]

[ chemical formula 32]

Since the above organic compound has a good hole-transporting property, a light-emitting element with low driving voltage can be manufactured by using the organic compound as a host material or a material for a hole-transporting layer. Further, a light-emitting element with good light-emitting efficiency can be manufactured.

The above organic compound can be synthesized, for example, by the following synthesis scheme. As shown in the following synthesis scheme (a-1), in an organic compound according to one embodiment of the present invention, a halide of a naphthalene derivative or a trifluoromethanesulfonic acid compound (compound 1) is reacted with an organoboron compound of a carbazole derivative or a fused polycyclic carbazole derivative or boric acid (compounds 2 and 3) by a suzuki-miyaura reaction, whereby a target compound can be obtained.

[ chemical formula 33]

In the synthetic scheme (A-1), Ar¹Represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. In addition, in R¹To R⁷In, R¹And R²、R⁴And R⁵、R⁵And R⁶And R⁶And R⁷At least one group of (b) is fused to form a benzene ring, and the others independently represent any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. Ar (Ar)²Represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. In addition, in R¹¹To R¹⁷In, R¹¹And R¹²、R¹⁴And R¹⁵、R¹⁵And R¹⁶And R¹⁶And R¹⁷The aromatic ring may be fused to form a benzene ring, and the others independently represent any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. Note that R⁶⁰And R⁶¹And R⁶²And R⁶³The ring may be bonded to each other to form a ring. In addition, X¹And X²Represents halogen or trifluoromethylsulfonyl.

The suzuki-miyaura reaction is a chemical reaction in which an organoboron compound and an aryl halide are cross-coupled by the action of a nucleophile such as a palladium catalyst and a base to obtain an asymmetric biaryl (biphenyl derivative), and examples of the palladium catalyst include palladium (II) acetate, tetrakis (triphenylphosphine) palladium (0), bis (triphenylphosphine) palladium (II) dichloride, and examples of the ligand of the palladium catalyst include tris (o-tolyl) phosphine, triphenylphosphine, tricyclohexylphosphine, and the like. Examples of the base include organic bases such as sodium tert-butoxide and inorganic bases such as potassium carbonate and sodium carbonate.

In the above reaction, the compound 2 and the compound 3 are an organoboron compound or boric acid, but may be an organoaluminum compound, an organozirconium compound, an organozinc compound, an organotin compound or the like.

In the above reaction, the organoboron compound or boric acid of the carbazole derivative may be reacted with a halide of the naphthalene derivative, or the organoboron compound or boric acid of the naphthalene derivative may be reacted with a halide of the carbazole derivative.

As shown in the following synthesis scheme (a-2), an organic compound according to one embodiment of the present invention can be obtained by coupling a fused polycyclic carbazole derivative (compound 4) with an aromatic halide (compound 5, compound 6) by a Hartwig-buhwald reaction.

[ chemical formula 34]

In Synthesis scheme (A-2), Ar¹Represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. In addition, in R¹To R⁷In, R¹And R²、R⁴And R⁵、R⁵And R⁶And R⁶And R⁷At least one group of (b) is fused to form a benzene ring, and the others independently represent any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. Ar (Ar)²Represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. In addition, in R¹¹To R¹⁷In, R¹¹And R¹²、R¹⁴And R¹⁵、R¹⁵And R¹⁶And R¹⁶And R¹⁷The aromatic ring may be fused to form a benzene ring, and the others independently represent any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. In addition, X³And X⁴Represents halogen, preferably iodine, bromine and chlorine.

The hartweichi-buhward reaction is a chemical reaction in which an aromatic halide and an amine are bonded in the presence of a palladium catalyst and a base, and examples of the palladium catalyst include bis (dibenzylideneacetone) palladium (0), palladium (II) acetate, and the like, and as a ligand of the palladium catalyst, tri (tert-butyl) phosphine, tri (n-hexyl) phosphine, tricyclohexylphosphine, and the like can be used. Examples of the base include organic bases such as sodium tert-butoxide and inorganic bases such as potassium carbonate, and examples of the solvent include toluene, xylene, benzene, tetrahydrofuran, and the like.

As the reaction represented by the above synthesis scheme (A-2), in addition to the Hartvich-Buhward reaction, Ullmann reaction and the like can be used.

(embodiment mode 2)

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

The EL layer 103 includes a light-emitting layer 113 and may further include a hole-transporting layer 112. The light-emitting layer 113 contains a light-emitting material and a host material, and the light-emitting element according to one embodiment of the present invention emits light from the light-emitting material. The organic compound according to one embodiment of the present invention may be included in any portion of the EL layer 103, but is preferably used as a material of the light-emitting layer 113 or the hole-transporting layer 112.

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

The organic compound according to one embodiment of the present invention can also be used as a host material for emitting a light-emitting substance in a light-emitting layer. In this case, the exciplex formed from the electron-transporting material and the organic compound according to one embodiment of the present invention may be formed by co-evaporation with the electron-transporting material. By forming an exciplex having an appropriate light-emitting wavelength, efficient energy transfer to a light-emitting material can be achieved, and thus a light-emitting element having high efficiency and a long lifetime can be provided.

Further, since the organic compound according to one embodiment of the present invention has a good hole-transporting property, it is effective to use the organic compound for the hole-transporting layer 112 or the electron-blocking layer provided between the hole-transporting layer 112 and the light-emitting layer 113.

Next, a detailed structure and material example of the light-emitting element will be described. As described above, the light-emitting element according to one embodiment of the present invention includes the EL layer 103 formed of a plurality of layers between the pair of the first electrode 101 and the second electrode 102. The EL layer 103 includes at least a light-emitting layer 113.

The EL layer 103 is not particularly limited, and various layer structures including layers having various functions such as a hole injection layer, a hole transport layer, an electron injection layer, a carrier block layer, an exciton block layer, and a charge generation layer can be used.

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

Here, as a laminated structure of the EL layer 103, the following two structures are explained: the structure shown in fig. 1A includes 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; fig. 1B shows a structure including a hole injection layer 111, a hole transport layer 112, a light-emitting layer 113, an electron transport layer 114, an electron injection layer 115, and a charge generation layer 116. The materials constituting the respective layers are specifically shown below.

The hole injection layer 111 is a layer containing a substance having a receptor. Although both organic and inorganic substances can be used as the substance having a receptor, the organic compound having a receptor tends to be easily vapor-deposited and handled, and the inorganic compound has a strong receptor and a high hole-injecting property.

Examples of the organic compound having an acceptor include compounds having an electron-withdrawing group (a halogen group or a cyano group), 7,8, 8-tetracyano-2, 3,5, 6-tetrafluoroquinodimethane (abbreviated as F4-TCNQ), chloranil, 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (abbreviated as HAT-CN), 1,3,4,5,7, 8-hexafluorotetracyano-naphthoquinodimethane (naphthonodimethane) (abbreviated as F6-TCNNQ), and [2- (7-dicyanomethylene-1, 3,4,5,6, 8,9, 10-octafluoro-7H-pyrene-2-ylidene) propanedinitrile ]. 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 preferable because it has a very high electron-accepting property, and specifically, there are: α, α ', α ″ -1,2, 3-cyclopropane triylidene (ylidene) tris (4-cyano-2, 3,5, 6-tetrafluorophenylacetonitrile), α ', α ″ -1,2, 3-cyclopropane triylidene tris [2, 6-dichloro-3, 5-difluoro-4- (trifluoromethyl) phenylacetonitrile ], α ', α ″ -1,2, 3-cyclopropane triylidene tris (2,3,4,5, 6-pentafluorophenylacetonitrile), and the like.

As the inorganic compound having a receptor, molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, or the like can be used. In addition, phthalocyanine compounds such as phthalocyanine (abbreviated as H) can also be used₂Pc), copper phthalocyanine (abbreviation: CuPC), and the like; aromatic amine compounds such as 4,4' -bis [ N- (4-diphenylaminophenyl) -N-phenylamino]Biphenyl (DPAB), N' -bis {4- [ bis (3-methylphenyl) amino group]Phenyl } -N, N ' -diphenyl- (1,1' -biphenyl) -4,4' -diamine (abbreviation): DNTPD), and the like; or a polymer such as poly (3, 4-ethylenedioxythiophene)/poly (styrenesulfonic acid) (PEDOT/PSS), etc. to form the hole injection layer 111.

In addition, as the hole injection layer 111, a composite material containing an acceptor substance in a substance having a hole-transporting property can be used. Note that by using a composite material in which a substance having a acceptor is contained in a substance having a hole-transporting property, the limitation of selection of an electrode-forming material according to the work function can be greatly alleviated. In other words, as the first electrode 101, not only a material having a large work function but also a material having a small work function can be used. Examples of the organic compound having acceptor and the transition metal oxide include those described above. Further, oxides of metals belonging to the fourth to eighth groups of the periodic table may be mentioned. As the metal oxide belonging to the fourth to eighth groups of the periodic table, a metal oxide having high electron acceptor such as vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, rhenium oxide, or the like is preferably used. Molybdenum oxide is particularly preferably used because it is also stable in the atmosphere, has low hygroscopicity, and is easy to handle.

As the hole transporting substance used for the composite material, various organic compounds such as aromatic amine compounds, carbazole derivatives, aromatic hydrocarbons, high molecular compounds (oligomers, dendrimers, polymers, etc.), and the like can be used. As the hole-transporting substance used in the composite material, it is preferable to use a substance having a hole mobility of 10^-6cm²A substance having a ratio of Vs to V or more. Hereinafter, organic compounds that can be used as the hole-transporting substance in the composite material are specifically exemplified.

Examples of the aromatic amine compound that can be used in the composite material include N, N ' -di (p-tolyl) -N, N ' -diphenyl-p-phenylenediamine (abbreviated as DTDPPA), 4' -bis [ N- (4-diphenylaminophenyl) -N-phenylamino ] biphenyl (abbreviated as DPAB), N ' -bis {4- [ bis (3-methylphenyl) amino ] phenyl } -N, N ' -diphenyl- (1,1' -biphenyl) -4,4' -diamine (abbreviated as DNTPD), 1,3, 5-tris [ N- (4-diphenylaminophenyl) -N-phenylamino ] benzene (abbreviated as DPA3B), and the like. Specific examples of the carbazole derivative include 3- [ N- (9-phenylcarbazol-3-yl) -N-phenylamino ] -9-phenylcarbazole (abbreviated as PCzPCA1), 3, 6-bis [ N- (9-phenylcarbazol-3-yl) -N-phenylamino ] -9-phenylcarbazole (abbreviated as PCzPCA2), 3- [ N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) amino ] -9-phenylcarbazole (abbreviated as PCzPCN1), 4' -bis (N-carbazolyl) biphenyl (abbreviated as CBP), 1,3, 5-tris [4- (N-carbazolyl) phenyl ] benzene (abbreviated as TCPB), 9- [4- (10-phenylanthracen-9-yl) phenyl ] -9H Carbazole (abbreviated as CzPA), 1, 4-bis [4- (N-carbazolyl) phenyl ] -2,3,5, 6-tetraphenylbenzene, and the like. Examples of the aromatic hydrocarbon include 2-tert-butyl-9, 10-di (2-naphthyl) anthracene (abbreviated as t-BuDNA), 2-tert-butyl-9, 10-di (1-naphthyl) anthracene, 9, 10-bis (3, 5-diphenylphenyl) anthracene (abbreviated as DPPA), 2-tert-butyl-9, 10-bis (4-phenylphenyl) anthracene (abbreviated as t-BuDBA), 9, 10-di (2-naphthyl) anthracene (abbreviated as DNA), 9, 10-diphenylpnthracene (abbreviated as DPAnth), 2-tert-butylanthracene (abbreviated as t-BuAnth), 9, 10-bis (4-methyl-1-naphthyl) anthracene (abbreviated as DMNA), 2-tert-butyl-9, 10-bis [2- (1-naphthyl) phenyl ] anthracene, 9, 10-bis [2- (1-naphthyl) phenyl ] anthracene, 2,3,6, 7-tetramethyl-9, 10-di (1-naphthyl) anthracene, 2,3,6, 7-tetramethyl-9, 10-di (2-naphthyl) anthracene, 9' -bianthracene, 10 ' -diphenyl-9, 9' -bianthracene, 10 ' -bis (2-phenylphenyl) -9,9' -bianthracene, 10 ' -bis [ (2,3,4,5, 6-pentaphenyl) phenyl ] -9,9' -bianthracene, anthracene, tetracene, rubrene, perylene, 2,5,8, 11-tetra (tert-butyl) perylene, and the like. In addition, pentacene, coronene, or the like can be used. May have a vinyl skeleton. Examples of the aromatic hydrocarbon having a vinyl group include 4,4' -bis (2, 2-diphenylvinyl) biphenyl (abbreviated as DPVBi) and 9, 10-bis [4- (2, 2-diphenylvinyl) phenyl ] anthracene (abbreviated as DPVPA). Further, the organic compound according to one embodiment of the present invention can also be used.

In addition, polymer compounds such as Poly (N-vinylcarbazole) (abbreviated as PVK), Poly (4-vinyltriphenylamine) (abbreviated as PVTPA), Poly [ N- (4- { N '- [4- (4-diphenylamino) phenyl ] phenyl-N' -phenylamino } phenyl) methacrylamide ] (abbreviated as PTPDMA), Poly [ N, N '-bis (4-butylphenyl) -N, N' -bis (phenyl) benzidine ] (abbreviated as Poly-TPD) and the like can be used.

By forming the hole injection layer 111, hole injection properties can be improved, and a light-emitting element with a small driving voltage can be obtained.

The hole transport layer 112 is formed to contain a hole transport material. The hole-transporting material preferably has a density of 1X 10^- ⁶cm²A hole mobility of Vs or higher. The hole-transporting layer 112 preferably contains an organic compound according to one embodiment of the present invention. By containing the organic compound described in embodiment 1 in the hole transport layer 112, a light-emitting element having a long lifetime can be obtained. Further, a light-emitting element with good light-emitting efficiency can be obtained.

The light-emitting layer 113 is a layer containing a host material and a light-emitting material. The light-emitting material may be a fluorescent light-emitting material, a phosphorescent light-emitting material, a material exhibiting Thermally Activated Delayed Fluorescence (TADF), or another light-emitting material. The light-emitting layer may be a single layer or may be composed of a plurality of layers containing different light-emitting materials. In one embodiment of the present invention, the light-emitting layer 113 is preferably used as a layer which exhibits fluorescence emission, particularly blue fluorescence emission. The organic compound according to one embodiment of the present invention can be used as a host material, and is particularly suitably used as a host material for a blue fluorescent material.

In the light-emitting layer 113, as a material which can be used as a fluorescent light-emitting substance, for example, the following materials can be given. In addition, other fluorescent substances may be used.

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), 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-3Amine (abbreviated as PCAPA), perylene, 2,5,8, 11-tetra-tert-butylperylene (abbreviated as TBP), 4- (10-phenyl-9-anthryl) -4'- (9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviated as PCBAPA), N' - (2-tert-butylanthryl-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-anthracenyl]-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-2-)-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 '-diphenyl-N, N' - (1, 6-pyrene-diyl) bis [ (6-phenylbenzo [ b ] b]Naphtho [1,2-d ]]Furan) -8-amines](abbreviation: 1, 6BnfAPrn-03), 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 high hole-trapping properties and good light-emitting efficiency and reliability.

In the light-emitting layer 113, as a material which can be used as a phosphorescent substance, for example, the following materials can be given.

For example, there may be mentioned: tris {2- [5- (2-methylphenyl) -4- (2, 6-dimethylphenyl) -4H-1,2, 4-triazol-3-yl- } - κ N2]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']And organometallic iridium complexes having, as a ligand, a phenylpyridine derivative having an electron-withdrawing group, such as iridium (III) acetylacetonate (abbreviated as "FIRacac"). The above substance is a compound emitting blue phosphorescence, and has a peak of light emission at 440nm to 520 nm.

In addition, 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) (abbreviation: [ Ir (mpmppm))₂(acac)]) And (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 compounds that mainly emit green phosphorescence, and have a peak of luminescence at 500nm to 600 nm. In addition, an organometallic iridium complex having a pyrimidine skeleton is particularly preferable because of its particularly excellent reliability and light emission efficiency.

In addition, 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) (abbreviation: [ 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 that emits red phosphorescence, and has a peak of light emission at 600nm to 700 nm. In addition, the organometallic iridium complex having a pyrazine skeleton can emit red light with good chromaticity.

In addition to the phosphorescent compound, a known phosphorescent material may be selected and used.

As TADF material, fullerene can be usedAnd derivatives thereof, acridine and derivatives thereof, and eosin derivatives, and the like. Further, metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), palladium (Pd), or the like can be cited. 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 35]

In addition, 2- (biphenyl-4-yl) -4, 6-bis (12-phenylindole [2, 3-a) represented by the following structural formula can also be used]Carbazol-11-yl) -1,3, 5-triazine (abbreviation: PIC-TRZ), 9- (4, 6-diphenyl-1, 3, 5-triazin-2-yl) -9 ' -phenyl-9H, 9' H-3, 3' -bicarbazole (abbreviation: PCCzTzn), 9- [4- (4, 6-diphenyl-1, 3, 5-triazin-2-yl) phenyl]-9 ' -phenyl-9H, 9' H-3, 3' -bicarbazole (PCCzPTzn), 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 (abbreviated as PPZ-3TPT), 3- (9, 9-dimethyl-9H-acridin-10-yl) -9H-xanthen-9-one (abbreviated as ACRXTN), bis [4- (9, 9-dimethyl-9, 10-dihydroacridine) phenyl]Sulfosulfone (DMAC-DPS), 10-phenyl-10H, 10 'H-spiro [ acridine-9, 9' -anthracene]And heterocyclic compounds having both a pi-electron-rich heteroaromatic ring and a pi-electron-deficient heteroaromatic ring, such as-10' -ketone (ACRSA). The heterocyclic compound preferably has a pi-electron-rich heteroaromatic ring and a pi-electron-deficient heteroaromatic ring, and is high in both electron-transporting property and hole-transporting property. In the substances directly bonded with the pi electron-rich heteroaromatic ring and the pi electron-deficient heteroaromatic ring,the donor properties and acceptor properties of the pi-electron-rich and pi-electron-deficient heteroaromatic rings are high and S is₁Energy level and T₁The energy difference between the energy levels becomes small, and thermally activated delayed fluorescence can be obtained efficiently, so that it is particularly preferable. In addition, instead of the pi-electron deficient heteroaromatic ring, an aromatic ring to which an electron withdrawing group such as a cyano group is bonded may be used.

[ chemical formula 36]

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

In addition, examples of the material having a hole-transporting property include: 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) Amine (short for PCBA1BP), 4' -diphenyl-4 ' - (9-phenyl-9H-carbazol-3-yl) triphenylamine (short for PCBBi1BP), 4- (1-naphthyl) -4' - (9-phenyl-9H-carbazol-3-yl) -triphenylamine (short for PCBANB), 4' -di (1-naphthyl) -4' - (9-phenyl-9H-carbazol-3-yl) triphenylamine (short for PCBNBB), 9-dimethyl-N-phenyl-N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl ] -fluorene-2-amine (short for PCBAF), Compounds having an aromatic amine skeleton such as N-phenyl-N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl ] -spiro-9, 9' -bifluorene-2-amine (PCBASF); 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, the organic compound described in embodiment 1 can be used as appropriate.

Examples of the material having an electron-transporting property 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-oxadiazole-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]Heterocyclic ring having pyridine skeleton such as benzene (abbreviated as TmPyPB)A compound (I) is provided. 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 fluorescent light-emitting substance is used as a light-emitting material, a material having an anthracene skeleton is preferably used as a host material. By using a substance having an anthracene skeleton as a host material of a fluorescent substance, a light-emitting layer having excellent light-emitting efficiency and durability can be realized. Among the substances having an anthracene skeleton used as a host material, a substance having a diphenylanthracene skeleton (particularly, a 9, 10-diphenylanthracene skeleton) is chemically stable, and is therefore preferable. In addition, when the host material has a carbazole skeleton, the hole injection/transport properties are improved, which is preferable. In particular, in the case of a benzocarbazole skeleton in which a benzene ring is fused to a carbazole, the HOMO level is shallower by about 0.1eV than that of carbazole, 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 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 the above-described hole injecting/transporting property, 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-phenyl-9-anthryl) 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), and the like. In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA are preferable because they exhibit very good characteristics. Note that the organic compound according to one embodiment of the present invention is very suitable for a material of a hole transport layer adjacent to a light-emitting layer of a fluorescent light-emitting element using these host materials.

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 a material having an electron-transporting property and a material having a hole-transporting property. By mixing a material having an electron-transporting property and a material having a hole-transporting property, 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 of the material having a hole-transporting property to the material having an electron-transporting property may be 1:9 to 9: 1.

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. In addition, this structure is preferable because the driving voltage can be reduced.

The electron transport layer 114 is a layer containing a substance having an electron transport property. As the substance having an electron-transporting property, the substance having an electron-transporting property which can be used for the host material described above can be used.

Lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF) may be disposed between the electron transport layer 114 and the second electrode 102₂) And the like, an alkali metal, an alkaline earth metal, or a compound thereof, as the electron injection layer 115. As the electron injection layer 115, a layer containing an alkali metal, an alkaline earth metal, or a compound thereof in a layer made of a substance having an electron-transporting property, or an electron compound (electrode) can be used. Examples of the electron compound include a compound in which electrons are added to a mixed oxide of calcium and aluminum at a high concentration.

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

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

The electron relay layer 118 contains at least a substance having an electron-transporting property, and can prevent interaction between the electron injection buffer layer 119 and the P-type layer 117 and smoothly transfer electrons. The LUMO level of the substance having an electron-transporting property included in the electron relay layer 118 is preferably set between the LUMO level of the acceptor substance in the P-type layer 117 and the LUMO level of the substance included in the layer in contact with the charge generation layer 116 in the electron transport layer 114. Specifically, the LUMO level of the substance having an electron-transporting property in the electron relay layer 118 is preferably-5.0 eV or more, and more preferably-5.0 eV or more and-3.0 eV or less. In addition, as the substance having an electron-transporting property in the electron relay layer 118, 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 119 may 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 the case where the electron injection buffer layer 119 contains a substance having an electron-transporting property and a donor substance, the donor substance may be an alkali metal, an alkaline earth metal, a rare earth metal, or a compound of these substances (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, and a carbonate), or a compound of a rare earth metal (including an oxide, a halide, and a carbonate)), or an organic compound such as tetrathianaphthacene (abbreviated as TTN), nickelocene, or decamethylnickelocene. The substance having an electron-transporting property can be formed using the same material as that used for the electron-transporting layer 114 described above.

As a substance forming the second electrode 102, a metal, an alloy, a conductive compound, a mixture thereof, or the like having a small work function (specifically, 3.8eV or less) can be used. Specific examples of such a cathode material include alkali metals such as lithium (Li) and cesium (Cs), elements belonging to group 1 or group 2 of the periodic table such as magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing them (MgAg, AlLi), rare earth metals such as europium (Eu), and ytterbium (Yb), and alloys containing them. However, by providing an electron injection layer between the second electrode 102 and the electron transport layer, various conductive materials such as Al, Ag, ITO, indium oxide-tin oxide containing silicon or silicon oxide, or the like can be used as the second electrode 102 regardless of the magnitude of the work function. These conductive materials can be formed by a dry method such as a vacuum evaporation method or a sputtering method, an ink jet method, a spin coating method, or the like. The metal oxide layer can be formed by a wet method such as a sol-gel method or a wet method using a paste of a metal material.

As a method for forming the EL layer 103, various methods can be used, regardless of a dry method or a wet method. For example, a vacuum vapor deposition method, a gravure printing method, a screen printing method, an ink jet method, a spin coating method, or the like may be used.

In addition, the electrodes or layers described above may be formed by using different film formation methods.

Note that the structure of the layer provided between the first electrode 101 and the second electrode 102 is not limited to the above-described structure. However, it is preferable to adopt a structure in which a light-emitting region where holes and electrons are recombined is provided in a portion distant from the first electrode 101 and the second electrode 102 in order to suppress quenching that occurs due to the proximity of the light-emitting region to a metal used for the electrode or the carrier injection layer.

In addition, in order to suppress energy transfer from excitons generated in the light-emitting layer, a carrier transport layer such as a hole transport layer and an electron transport layer which are in contact with the light-emitting layer 113, particularly a carrier transport layer near a recombination region in the light-emitting layer 113 is preferably formed using a substance having a band gap larger than that of a light-emitting material constituting the light-emitting layer or a light-emitting material contained in the light-emitting layer.

Next, a mode of a light-emitting element (hereinafter, also referred to as a stacked element or a series element) having a structure in which a plurality of light-emitting units are stacked will be described with reference to fig. 1C. The light-emitting element is a light-emitting element having a plurality of light-emitting units between an anode and a cathode. One light-emitting unit has substantially the same structure as the EL layer 103 shown in fig. 1A. That is, it can be said that the light-emitting element shown in fig. 1C is a light-emitting element having a plurality of light-emitting units, and the light-emitting element shown in fig. 1A or 1B is a light-emitting element having one light-emitting unit.

In fig. 1C, a first light emitting unit 511 and a second light emitting unit 512 are stacked between an anode 501 and a cathode 502, and a charge generation layer 513 is provided between the first light emitting unit 511 and the second light emitting unit 512. The anode 501 and the cathode 502 correspond to the first electrode 101 and the second electrode 102 in fig. 1A, respectively, and the same materials as those described in fig. 1A can be applied. In addition, the first and second

light emitting units

511 and 512 may have the same structure or different structures.

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

The charge generation layer 513 preferably has the same structure as the charge generation layer 116 shown in fig. 1B. Since the composite material of the organic compound and the metal oxide has good carrier injection property and carrier transport property, low voltage driving and low current driving can be realized. Note that in the case where the anode-side surface of the light-emitting unit is in contact with the charge generation layer 513, the charge generation layer 513 may function as a hole injection layer of the light-emitting unit, and therefore the light-emitting unit may not be provided with a hole injection layer.

In addition, in the case where the electron injection buffer layer 119 is provided for the charge generation layer 513, since the electron injection buffer layer 119 has a function of an electron injection layer in the light emitting cell on the anode side, the electron injection layer does not necessarily have to be provided in the light emitting cell on the anode side.

Although the light-emitting element having two light-emitting units is illustrated in fig. 1C, a light-emitting element in which three or more light-emitting units are stacked may be similarly applied. As in the light-emitting element according to the present embodiment, by disposing a plurality of light-emitting cells with the charge generation layer 513 being separated between a pair of electrodes, the element can realize high-luminance light emission while maintaining a low current density, and can realize an element having a long lifetime. In addition, a light-emitting device which can be driven at low voltage and has low power consumption can be realized.

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

Each of the EL layer 103, the first light-emitting unit 511, the second light-emitting unit 512, the charge generation layer, and the like, and the electrode can be formed by a method such as vapor deposition (including vacuum vapor deposition), droplet discharge (also referred to as an ink jet method), coating, or gravure printing. In addition, it may also contain low molecular materials, medium molecular materials (including oligomers, dendrimers) or high molecular materials.

(embodiment mode 3)

In this embodiment, a light-emitting device using the light-emitting element described in embodiment 2 will be described.

In this embodiment, a light-emitting device manufactured using the light-emitting element described in embodiment 2 will be described with reference to fig. 2. Note that fig. 2A is a plan view showing the light-emitting device, and fig. 2B is a sectional view taken along a-B and C-D in fig. 2A. The light-emitting device includes a driver circuit portion (source line driver circuit) 601, a pixel portion 602, and a driver circuit portion (gate line driver circuit) 603, which are indicated by broken lines, as means for controlling light emission of the light-emitting element. In addition, reference numeral 604 denotes a sealing substrate, reference numeral 605 denotes a sealing material, and the inside surrounded by the sealing material 605 is a space 607.

Note that the lead wiring 608 is a wiring for transmitting signals input to the source line driver circuit 601 and the gate line driver circuit 603, and receives a video signal, a clock signal, a start signal, a reset signal, and the like from an FPC (flexible printed circuit) 609 serving as an external input terminal. Note that although only the FPC is illustrated here, the FPC may be mounted with a Printed Wiring Board (PWB). The light-emitting device in this specification includes not only a light-emitting device main body but also a light-emitting device on which an FPC or a PWB is mounted.

Next, a cross-sectional structure is explained with reference to fig. 2B. Although a driver circuit portion and a pixel portion are formed over the element substrate 610, one pixel of the source line driver circuit 601 and the pixel portion 602 which are the driver circuit portion is illustrated here.

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

There is no particular limitation on the structure of the transistor used for the pixel or the driver circuit. For example, an inverted staggered transistor or a staggered transistor may be employed. In addition, either a top gate type transistor or a bottom gate type transistor may be used. The semiconductor material used for the transistor is not particularly limited, and for example, silicon, germanium, silicon carbide, gallium nitride, or the like can be used. Alternatively, an oxide semiconductor containing at least one of indium, gallium, and zinc such as an In-Ga-Zn metal oxide can be used.

The crystallinity of a semiconductor material used for a transistor is also not particularly limited, and an amorphous semiconductor or a crystalline semiconductor (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, or a semiconductor in which a part thereof has a crystalline region) can be used. When a crystalline semiconductor is used, deterioration in characteristics of the transistor can be suppressed, and therefore, the crystalline semiconductor is preferable.

Here, the oxide semiconductor is preferably used for a semiconductor device such as a transistor provided in the pixel or the driver circuit and a transistor used in a touch sensor or the like described later. It is particularly preferable to use an oxide semiconductor whose band gap is wider than that of silicon. By using an oxide semiconductor having a wider band gap than silicon, off-state current (off-state current) of the transistor can be reduced.

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

In particular, as the semiconductor layer, the following oxide semiconductor films are preferably used: the semiconductor device includes a plurality of crystal portions, each of which has a c-axis oriented in a direction perpendicular to a surface of the semiconductor layer to be formed or a top surface of the semiconductor layer and has no grain boundary between adjacent crystal portions.

By using the above-described material for the semiconductor layer, a highly reliable transistor in which variation in electrical characteristics is suppressed can be realized.

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

In order to stabilize the characteristics of a transistor or the like, a base film is preferably provided. The base film can be formed using an inorganic insulating film such as a silicon oxide film, a silicon nitride film, a silicon oxynitride film, or a silicon nitride oxide film in a single layer or a stacked layer. The base film can be formed by a sputtering method, a CVD (Chemical Vapor Deposition) method (a plasma CVD method, a thermal CVD method, an MOCVD (Metal Organic CVD: Organic Metal Chemical Vapor Deposition) method, an ALD (Atomic Layer Deposition) method, a coating method, a printing method, or the like. Note that the base film may not be provided if it is not necessary.

Note that the FET623 shows one of transistors formed in the driver circuit portion 601. The driver circuit may be formed using various CMOS circuits, PMOS circuits, or NMOS circuits. In addition, although this embodiment mode shows a driver-integrated type in which a driver circuit is formed over a substrate, this structure is not always necessary, and the driver circuit may be formed outside without being formed over the substrate.

Further, the pixel portion 602 is formed of a plurality of pixels each including the switching FET 611, the current controlling FET612, and the first electrode 613 electrically connected to the drain of the current controlling FET612, but is not limited thereto, and a pixel portion in which three or more FETs and capacitors are combined may be employed.

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

In addition, the upper end portion or the lower end portion of the insulator 614 is formed into a curved surface having a curvature to obtain good coverage of an EL layer or the like formed later. For example, in the case of using a positive photosensitive acrylic resin as a material of the insulator 614, it is preferable that only the upper end portion of the insulator 614 includes a curved surface having a radius of curvature (0.2 μm to 3 μm). As the insulator 614, a negative photosensitive resin or a positive photosensitive resin can be used.

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

The EL layer 616 is formed by various methods such as a vapor deposition method using a vapor deposition mask, an ink jet method, and a spin coating method. The EL layer 616 has the structure described in embodiment 1. As another material constituting the EL layer 616, a low molecular compound or a high molecular compound (including an oligomer and a dendrimer) may be used.

As a material for the second electrode 617 which is formed over the EL layer 616 and used as a cathode, a material having a small work function (Al, Mg, Li, Ca, an alloy or a compound thereof (MgAg, MgIn, AlLi, or the like)) is preferably used. Note that when light generated in the EL layer 616 is transmitted through the second electrode 617, a stack of a thin metal film having a reduced thickness and a transparent conductive film (ITO, indium oxide containing 2 wt% to 20 wt% of zinc oxide, indium tin oxide containing silicon, zinc oxide (ZnO), or the like) is preferably used as the second electrode 617.

The light-emitting element is formed of a first electrode 613, an EL layer 616, and a second electrode 617. The light-emitting element is the light-emitting element described in embodiment 2. The pixel portion is formed of a plurality of light-emitting elements, and the light-emitting device of this embodiment may include both the light-emitting element described in embodiment 2 and a light-emitting element having another structure.

Further, by bonding the sealing substrate 604 to the element substrate 610 with the sealing material 605, the light-emitting element 618 is provided in the space 607 surrounded by the element substrate 610, the sealing substrate 604, and the sealing material 605. Note that the space 607 is filled with a filler, and as the filler, an inert gas (nitrogen, argon, or the like) may be used, or a sealing material may be used. By forming a recess in the sealing substrate and providing a drying agent therein, deterioration due to moisture can be suppressed, and therefore, this is preferable.

In addition, epoxy resin or glass frit is preferably used as the sealing material 605. These materials are preferably materials that are as impermeable as possible to moisture and oxygen. As a material for the sealing substrate 604, a glass substrate or a quartz substrate, and a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (polyvinyl fluoride), polyester, acrylic resin, or the like can be used.

Although not shown in fig. 2, a protective film may be provided on the second electrode. The protective film may be formed of an organic resin film or an inorganic insulating film. Further, a protective film may be formed so as to cover the exposed portion of the sealing material 605. The protective film may be provided so as to cover the surfaces and side surfaces of the pair of substrates, and the exposed side surfaces of the sealing layer, the insulating layer, and the like.

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

As a material constituting the protective film, an oxide, a nitride, a fluoride, a sulfide, a ternary compound, a metal, a polymer, or the like can be used. For example, materials containing aluminum oxide, hafnium silicate, lanthanum oxide, silicon oxide, strontium titanate, tantalum oxide, titanium oxide, zinc oxide, niobium oxide, zirconium oxide, tin oxide, yttrium oxide, cerium oxide, scandium oxide, erbium oxide, vanadium oxide, indium oxide, and the like, materials containing aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, titanium nitride, niobium nitride, molybdenum nitride, zirconium nitride, gallium nitride, and the like, materials containing nitrides containing titanium and aluminum, oxides containing aluminum and zinc, sulfides containing manganese and zinc, sulfides containing cerium and strontium, oxides containing erbium and aluminum, oxides containing yttrium and zirconium, and the like can be used.

The protective film is preferably formed by a film formation method having good step coverage (step coverage). One such method is the Atomic Layer Deposition (ALD) method. A material that can be formed by the ALD method is preferably used for the protective film. The protective film having a high density, reduced defects such as cracks and pinholes, and a uniform thickness can be formed by the ALD method. In addition, damage to the processing member when the protective film is formed can be reduced.

For example, a protective film having a uniform and small number of defects can be formed on a surface having a complicated uneven shape or on the top surface, side surfaces, and back surface of a touch panel by the ALD method.

As described above, a light-emitting device manufactured using the light-emitting element described in embodiment mode 2 can be obtained.

Since the light-emitting element described in embodiment mode 2 is used for the light-emitting device in this embodiment mode, a light-emitting device having excellent characteristics can be obtained. Specifically, the light-emitting element described in embodiment 2 is a light-emitting element having a long lifetime, and thus a light-emitting device having high reliability can be realized. Further, a light-emitting device using the light-emitting element described in embodiment mode 2 has good light-emitting efficiency, and thus can realize a light-emitting device with low power consumption.

Fig. 3 shows an example of a light-emitting device which realizes full color by providing a colored layer (color filter) or the like for forming a light-emitting element which emits white light. Fig. 3A illustrates a substrate 1001, a base insulating film 1002, a gate insulating film 1003,

gate electrodes

1006, 1007, 1008, a first interlayer insulating film 1020, a second interlayer insulating film 1021, a peripheral portion 1042, a pixel portion 1040, a driver circuit portion 1041,

first electrodes

1024W, 1024R, 1024G, 1024B of a light emitting element, a partition wall 1025, an EL layer 1028, a second electrode 1029 of a light emitting element, a sealing substrate 1031, a sealing material 1032, and the like.

In fig. 3A, colored layers (a red colored layer 1034R, a green colored layer 1034G, and a blue colored layer 1034B) are provided on the transparent base 1033. In addition, a black matrix 1035 may be provided. The transparent base 1033 provided with the colored layer and the black matrix is aligned and fixed to the substrate 1001. The color layer and the black matrix 1035 are covered with a protective layer 1036. Fig. 3A shows a light-emitting layer in which light is transmitted to the outside without passing through the colored layer, and a light-emitting layer in which light is transmitted to the outside with passing through the colored layer of each color.

Fig. 3B shows an example in which colored layers (a red colored layer 1034R, a green colored layer 1034G, and a blue colored layer 1034B) are formed between the gate insulating film 1003 and the first interlayer insulating film 1020. As described above, the coloring layer may be provided between the substrate 1001 and the sealing substrate 1031.

In addition, although the light-emitting device having the structure (bottom emission type) in which light is extracted from the side of the substrate 1001 where the FET is formed has been described above, a light-emitting device having the structure (top emission type) in which light is extracted from the side of the sealing substrate 1031 may be employed. Fig. 4 illustrates a cross-sectional view of a top emission type light emitting device. In this case, a substrate which does not transmit light can be used as the substrate 1001. The steps up to the production of the connection electrode for connecting the FET to the anode of the light-emitting element are performed in the same manner as in the bottom emission type light-emitting device. Then, the third interlayer insulating film 1037 is formed so as to cover the electrode 1022. The third interlayer insulating film 1037 may have a function of flattening. The third interlayer insulating film 1037 can be formed using the same material as the second interlayer insulating film or another known material.

Although the

first electrodes

1024W, 1024R, 1024G, 1024B of the light emitting elements are anodes here, they may be cathodes. In addition, in the case of using a top emission type light-emitting device as shown in fig. 4, the first electrode is preferably a reflective electrode. The EL layer 1028 has the structure of the EL layer 103 described in embodiment 1, and has an element structure capable of obtaining white light emission.

In the case of employing the top emission structure shown in fig. 4, sealing may be performed using a sealing substrate 1031 provided with coloring layers (red coloring layer 1034R, green coloring layer 1034G, blue coloring layer 1034B). The sealing substrate 1031 may also be provided with a black matrix 1035 between pixels. The color layers (red color layer 1034R, green color layer 1034G, and blue color layer 1034B) and the black matrix 1035 may be covered with a protective layer 1036. As the sealing substrate 1031, a substrate having light-transmitting properties is used. Although an example in which full-color display is performed with four colors of red, green, blue, and white is shown here, this is not limitative, but full-color display may be performed with four colors of red, yellow, green, and blue, or three colors of red, green, and blue.

In the top emission type light emitting device, a microcavity structure may be preferably applied. A light-emitting element having a microcavity structure can be obtained by using the reflective electrode as the first electrode and the semi-transmissive/semi-reflective electrode as the second electrode. At least an EL layer is provided between the reflective electrode and the semi-transmissive/semi-reflective electrode, and at least a light-emitting layer which is a light-emitting region is provided.

Note that the reflective electrode has a visible light reflectance of 40% to 100%, preferably 70% to 100%, and a resistivity of 1 × 10^-2Omega cm or less. In addition, the semi-transmissive and semi-reflective electrode has a visible light reflectance of 20% to 80%, preferably 40% to 70%, and a resistivity of 1 × 10^-2Omega cm or less.

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

In this light-emitting element, the optical length between the reflective electrode and the semi-transmissive/semi-reflective electrode can be changed by changing the thickness of the transparent conductive film, the composite material, the carrier transporting material, or the like. This makes it possible to attenuate light of a wavelength not resonating while strengthening light of a wavelength resonating between the reflective electrode and the semi-transmissive/semi-reflective electrode.

Since the light (first reflected light) reflected by the reflective electrode greatly interferes with the light (first incident light) directly entering the semi-transmissive and semi-reflective electrode from the light-emitting layer, it is preferable to adjust the optical path length between the reflective electrode and the light-emitting layer to (2n-1) λ/4 (note that n is a natural number of 1 or more, and λ is the wavelength of light to be amplified). By adjusting the optical path length, the phase of the first reflected light can be made to coincide with that of the first incident light, whereby the light emitted from the light-emitting layer can be further amplified.

In addition, in the above structure, the EL layer may contain a plurality of light emitting layers, or may contain only one light emitting layer, and for example, a structure in which a plurality of EL layers are provided with a charge generation layer interposed therebetween in one light emitting element and one or more light emitting layers are formed in each EL layer and the above tandem type light emitting element are combined may be used.

By adopting the microcavity structure, the emission intensity in the front direction of a predetermined wavelength can be enhanced, and thus low power consumption can be achieved. Note that in the case of a light-emitting device which displays an image using subpixels of four colors of red, yellow, green, and blue, yellow light emission exhibits an effect of improving luminance, and a microcavity structure suitable for the wavelength of each color can be adopted for all subpixels, so that a light-emitting device having good characteristics can be realized.

Although the active matrix light-emitting device has been described so far, the passive matrix light-emitting device will be described below. Fig. 5 shows a passive matrix light-emitting device manufactured by using the present invention. Note that fig. 5A is a perspective view illustrating the light-emitting device, and fig. 5B is a sectional view taken along X-Y of fig. 5A. In fig. 5, an EL layer 955 is provided between an electrode 952 and an electrode 956 over a substrate 951. The ends of the electrodes 952 are covered by an insulating layer 953. An insulating layer 954 is provided over the insulating layer 953. The sidewalls of the isolation layer 954 have such an inclination that the closer to the substrate surface, the narrower the interval between the two sidewalls. In other words, the cross section of the partition layer 954 in the short side direction is trapezoidal, and the base (the side which faces the same direction as the surface direction of the insulating layer 953 and is in contact with the insulating layer 953) is shorter than the upper side (the side which faces the same direction as the surface direction of the insulating layer 953 and is not in contact with the insulating layer 953). Thus, by providing the partition layer 954, defects of the light-emitting element due to static electricity or the like can be prevented. In addition, in a passive matrix light-emitting device, a light-emitting device with high reliability or a light-emitting device with low power consumption can be obtained by using the light-emitting element described in embodiment 2.

The light-emitting device described above can control each of a plurality of minute light-emitting elements arranged in a matrix, and therefore can be suitably used as a display device for displaying an image.

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

(embodiment mode 4)

In this embodiment, an example in which the light-emitting element described in embodiment 2 is used in a lighting device will be described with reference to fig. 6. Fig. 6B is a top view of the lighting device, and fig. 6A is a cross-sectional view along e-f of fig. 6B.

In the lighting device of this embodiment mode, a first electrode 401 is formed over a substrate 400 having a light-transmitting property, which serves as a support. The first electrode 401 corresponds to the first electrode 101 in embodiment 1. When light is extracted from the first electrode 401 side, the first electrode 401 is formed using a material having light-transmitting properties.

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

An EL layer 403 is formed over the first electrode 401. The EL layer 403 corresponds to the structure of the EL layer 103 in embodiment 1, the structure of the combination of the light-emitting unit 511, the light-emitting unit 512, and the charge-generating layer 513, or the like. Note that, as their structures, the respective descriptions are referred to.

The second electrode 404 is formed so as to cover the EL layer 403. The second electrode 404 corresponds to the second electrode 102 in embodiment 1. When light is extracted from the first electrode 401 side, the second electrode 404 is formed using a material having high reflectance. By connecting the second electrode 404 to the pad 412, a voltage is supplied to the second electrode 404.

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

The substrate 400 on which the light-emitting element having the above-described structure is formed and the sealing substrate 407 are fixed and sealed with the sealing

materials

405 and 406, whereby an illumination device is manufactured. Only one of the sealing

materials

405 and 406 may be used. Further, the inner sealing material 406 (not shown in fig. 6B) may be mixed with a desiccant, thereby absorbing moisture and improving reliability.

In addition, by providing the pad 412 and a part of the first electrode 401 so as to extend to the outside of the sealing

materials

405 and 406, they can be used as external input terminals. Further, an IC chip 420 or the like on which a converter or the like is mounted may be provided on the external input terminal.

In the lighting device described in this embodiment mode, the light-emitting element described in embodiment mode 2 is used as an EL element, and a light-emitting device with high reliability can be realized. In addition, a light-emitting device with low power consumption can be realized.

(embodiment 5)

In this embodiment, an example of an electronic device including the light-emitting element described in embodiment 2 in part will be described. The light-emitting element described in embodiment 2 has a long life and is highly reliable. As a result, the electronic device described in this embodiment can realize an electronic device including a light-emitting portion with high reliability.

Examples of electronic devices using the light-emitting element include television devices (also referred to as televisions or television receivers), monitors of computers and the like, digital cameras, digital video cameras, digital photo frames, cellular phones (also referred to as cellular phones or cellular phone devices), portable game machines, portable information terminals, audio reproducing devices, large-sized game machines such as pachinko machines, and the like. Specific examples of these electronic devices are shown below.

Fig. 7A shows an example of a television device. In the television device, a display portion 7103 is incorporated in a housing 7101. In addition, a structure in which the housing 7101 is supported by a bracket 7105 is shown here. An image can be displayed on the display portion 7103, and the light-emitting elements described in embodiment 2 are arranged in a matrix in the display portion 7103.

The television apparatus can be operated by using an operation switch provided in the housing 7101 or a remote controller 7110 provided separately. By using the operation keys 7109 of the remote controller 7110, channels and volume can be controlled, and thus, an image displayed on the display portion 7103 can be controlled. In addition, the remote controller 7110 may be provided with a display portion 7107 for displaying information output from the remote controller 7110.

The television device is configured to include a receiver, a modem, and the like. General television broadcasts can be received by a receiver. Further, by connecting the modem to a wired or wireless communication network, information communication can be performed in one direction (from a sender to a receiver) or in two directions (between a sender and a receiver or between receivers).

Fig. 7B1 shows a computer including a main body 7201, a housing 7202, a display portion 7203, a keyboard 7204, an external connection port 7205, a pointing device 7206, and the like. The computer is manufactured by arranging the light-emitting elements described in embodiment 2 in a matrix and using the light-emitting elements for the display portion 7203. The computer in FIG. 7B1 may also be in the manner shown in FIG. 7B 2. The computer shown in fig. 7B2 is provided with a second display portion 7210 instead of the keyboard 7204 and the pointing device 7206. The second display unit 7210 is a touch panel, and input can be performed by operating an input display displayed on the second display unit 7210 with a finger or a dedicated pen. In addition, the second display portion 7210 can display not only an input display but also other images. The display portion 7203 may be a touch panel. Since the two panels are connected by the hinge portion, it is possible to prevent problems such as damage, breakage, etc. of the panels when stored or carried.

Fig. 7D shows an example of a portable terminal. The mobile phone includes a display portion 7402, operation buttons 7403, an external connection port 7404, a speaker 7405, a microphone 7406, and the like, which are incorporated in a housing 7401. The mobile phone 7400 includes a display portion 7402 manufactured by arranging light-emitting elements described in embodiment 2 in a matrix.

The mobile terminal shown in fig. 7C may be configured to input information by touching the display portion 7402 with a finger or the like. In this case, an operation such as making a call or writing an email can be performed by touching the display portion 7402 with a finger or the like.

The display portion 7402 mainly has three screen modes. The first is a display mode mainly in which images are displayed, the second is an input mode mainly in which information such as characters is input, and the third is a display input mode in which two modes, namely a mixed display mode and an input mode, are displayed.

For example, in the case of making a call or composing an e-mail, characters displayed on the screen may be input in a character input mode in which the display portion 7402 is mainly used for inputting characters. In this case, it is preferable that a keyboard or number buttons be displayed in most of the screen of the display portion 7402.

Further, by providing a detection device having a sensor for detecting inclination, such as a gyroscope or an acceleration sensor, in the mobile terminal, the direction (vertical or horizontal) of the mobile terminal can be determined, and the screen display of the display portion 7402 can be automatically switched.

Further, the screen mode is switched by touching the display portion 7402 or operating an operation button 7403 of the housing 7401. Alternatively, the screen mode may be switched depending on the type of image displayed on the display portion 7402. For example, when the image signal displayed on the display portion is data of a moving image, the screen mode is switched to the display mode, and when the image signal is text data, the screen mode is switched to the input mode.

In the input mode, when it is known that no touch operation input is made to the display portion 7402 for a certain period of time by detecting a signal detected by the optical sensor of the display portion 7402, the screen mode may be controlled to be switched from the input mode to the display mode.

The display portion 7402 can also be used as an image sensor. For example, by touching the display portion 7402 with the palm or the fingers, a palm print, a fingerprint, or the like is captured, and personal recognition can be performed. Further, by using a backlight that emits near-infrared light or a sensing light source that emits near-infrared light in the display portion, it is also possible to image finger veins, palm veins, and the like.

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

As described above, the light-emitting device including the light-emitting element described in embodiment 2 has a very wide range of applications, and the light-emitting device can be used in electronic devices in various fields. By using the light-emitting element described in embodiment mode 2, an electronic device with high reliability can be obtained.

Fig. 8A is a schematic view showing an example of the sweeping robot.

The sweeping robot 5100 includes a display 5101 on the top surface and a plurality of cameras 5102, brushes 5103, and operation buttons 5104 on the side surfaces. Although not shown, tires, a suction port, and the like are provided on the bottom surface of the sweeping robot 5100. The sweeping robot 5100 further includes various sensors such as an infrared sensor, an ultrasonic sensor, an acceleration sensor, a piezoelectric sensor, an optical sensor, and a gyro sensor. In addition, the sweeping robot 5100 includes a wireless communication unit.

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

The sweeping robot 5100 analyzes the image captured by the camera 5102, and can determine the presence or absence of an obstacle such as a wall, furniture, or a step. In addition, in the case where an object that may be wound around the brush 5103 such as a wire is detected by image analysis, the rotation of the brush 5103 may be stopped.

The remaining power of the battery, the amount of garbage attracted, and the like may be displayed on the display 5101. The walking path of the sweeping robot 5100 may be displayed on the display 5101. The display 5101 may be a touch panel, and the operation buttons 5104 may be displayed on the display 5101.

The sweeping robot 5100 can communicate with a portable electronic device 5140 such as a smartphone. An image taken by the camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the sweeping robot 5100 can know the condition of the room even when going out. In addition, the display content of the display 5101 can be confirmed using a portable electronic device such as a smartphone.

The light-emitting device according to one embodiment of the present invention can be used for the display 5101.

The robot 2100 illustrated in fig. 8B includes a computing device 2110, an illuminance sensor 2101, a microphone 2102, an upper camera 2103, a speaker 2104, a display 2105, a lower camera 2106, an obstacle sensor 2107, and a moving mechanism 2108.

The microphone 2102 has a function of detecting the voice of the user, the surrounding voice, and the like. In addition, the speaker 2104 has a function of emitting sound. The robot 2100 may communicate with a user using a microphone 2102 and a speaker 2104.

The display 2105 has a function of displaying various information. The robot 2100 may display information desired by the user on the display 2105. The display 2105 may be mounted with a touch panel. The display 2105 may be a detachable information terminal, and by installing the information terminal at a predetermined position of the robot 2100, charging and data transmission and reception are possible.

The upper camera 2103 and the lower camera 2106 have a function of imaging the environment around the robot 2100. The obstacle sensor 2107 may detect the presence or absence of an obstacle in front of the robot 2100 when it moves using the movement mechanism 2108. The robot 2100 can safely move around a world wide-bug environment using the upper camera 2103, the lower camera 2106, and the obstacle sensor 2107. The light-emitting device according to one embodiment of the present invention can be used for the display 2105.

Fig. 8C is a diagram showing an example of the goggle type display. The goggle type display includes, for example, a housing 5000, a display portion 5001, a speaker 5003, LED lamps 5004, operation keys 5005 (including a power switch or an operation switch), a connection terminal 5006, a sensor 5007 (which has a function of measuring a force, a displacement, a position, a velocity, 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 5008, a display portion 5002, a supporting portion 5012, an earphone 5013, and the like.

A light-emitting device which is one embodiment of the present invention can be used for the display portion 5001 and the second display portion 5002.

Fig. 9 shows an example in which the light-emitting element described in embodiment 2 is used for a desk lamp as a lighting device. The desk lamp shown in fig. 9 includes a housing 2001 and a light source 2002, and the lighting device described in embodiment 3 is used as the light source 2002.

Fig. 10 shows an example of an illumination device 3001 in which the light-emitting element described in embodiment 2 is used indoors. The light-emitting element described in embodiment 2 is a highly reliable light-emitting element, and thus a highly reliable lighting device can be realized. In addition, the light-emitting element described in embodiment 2 can be used for a lighting device having a large area because it can have a large area. In addition, since the light-emitting element described in embodiment 2 has a small thickness, a lighting device which can be thinned can be manufactured.

The light-emitting element described in embodiment 2 can be mounted on a windshield or an instrument panel of an automobile. Fig. 11 shows an embodiment in which the light-emitting element described in embodiment 2 is used for a windshield or an instrument panel of an automobile. The display regions 5200 to 5203 are displays provided using the light-emitting elements described in embodiment 2.

The display region 5200 and the display region 5201 are display devices provided on a windshield of an automobile and having the light-emitting element described in embodiment 2 mounted thereon. By manufacturing the first electrode and the second electrode of the light-emitting element described in embodiment mode 2 using the light-transmitting electrode, a so-called see-through display device in which a scene opposite to the first electrode can be seen can be obtained. If the see-through display is adopted, the field of view is not obstructed even if the display is arranged on the windshield of the automobile. In addition, in the case where a transistor or the like for driving is provided, a transistor having light transmittance such as an organic transistor using an organic semiconductor material or a transistor using an oxide semiconductor is preferably used.

The display region 5202 is a display device provided in a pillar portion and having the light-emitting element described in embodiment 2 mounted thereon. By displaying an image from an imaging unit provided on the vehicle compartment on the display area 5202, the view blocked by the pillar can be supplemented. Similarly, the display area 5203 provided on the dashboard portion displays an image from the imaging means provided outside the vehicle, thereby compensating for a blind spot in the field of view blocked by the vehicle cabin and improving safety. By displaying an image to supplement an invisible part, security is confirmed more naturally and simply.

The display area 5203 may also provide various information such as navigation information, speedometer, tachometer, distance traveled, fuel gauge, gear status, air conditioner settings, and the like. The user can change the display contents and arrangement appropriately. These pieces of information may be displayed in the display regions 5200 to 5202. In addition, the display regions 5200 to 5203 may be used as illumination devices.

Fig. 12A and 12B show a foldable portable information terminal 5150. The foldable portable information terminal 5150 includes a housing 5151, a display area 5152, and a bending portion 5153. Fig. 12A shows a portable information terminal 5150 in an expanded state. Fig. 12B shows the portable information terminal in a folded state. Although the portable information terminal 5150 has a large display area 5152, by folding the portable information terminal 5150, the portable information terminal 5150 becomes small and portability is good.

The display area 5152 may be folded in half by the bent portion 5153. The curved portion 5153 is composed of a stretchable member and a plurality of support members, and the stretchable member is stretched when folded, and is folded so that the curved portion 5153 has a radius of curvature of 2mm or more, preferably 3mm or more.

The display region 5152 may be a touch panel (input/output device) to which a touch sensor (input device) is attached. A light-emitting device according to one embodiment of the present invention can be used for the display region 5152.

Further, fig. 13A to 13C illustrate a foldable portable information terminal 9310. Fig. 13A shows the portable information terminal 9310 in an expanded state. Fig. 13B 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. 13C 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 panel 9311 is supported by three housings 9315 to which hinge portions 9313 are connected. Note that the display panel 9311 may be a touch panel (input/output device) mounted with a touch sensor (input device). In addition, by folding the display panel 9311 at the hinge portion 9313 between the two housings 9315, the portable information terminal 9310 can be reversibly changed from the unfolded state to the folded state. The light-emitting device according to one embodiment of the present invention can be used for the display panel 9311. Information icons, shortcut of applications or programs that are frequently used, and the like can be displayed on the side surface of the display panel 9311, and information can be confirmed or applications can be started smoothly.

[ example 1]

Synthesis example 1

In this example, a method for synthesizing an organic compound 8, 8' - (naphthalene-1, 4-diyl) bis (11-phenyl-11H-benzo [ a ] carbazole) (abbreviated as PaBC2N) according to one embodiment of the present invention will be described in detail. The structural formula of PaBC2N is shown below.

[ chemical formula 37]

A100 mL three-necked flask was charged with 0.56g (2.0mmol) of 1, 4-dibromonaphthalene, 1.7g (4.1mmol) of 2- (11-phenylbenzo [ a ] carbazol-8-yl) -4,4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan, 68mg (0.22mmol) of tri (o-tolyl) phosphine, 1.1g (8.2mmol) of potassium carbonate, 20mL of toluene, 4mL of water, and 4mL of ethanol. The mixture was stirred under reduced pressure to degas, and the air in the flask was replaced with nitrogen. To the mixture was added 22mg (96. mu. mol) of palladium (II) acetate, and the mixture was stirred at 80 ℃ for 6 hours under a nitrogen stream. After stirring, water was added to the resulting mixture, an aqueous layer and an organic layer were separated, and the aqueous layer was extracted with toluene. The organic layer and the extract solution were combined, washed with water, saturated brine and then dried over magnesium sulfate. The mixture was filtered, and the filtrate was concentrated to give an oil. This oil was purified by silica gel column chromatography (developing solvent toluene: hexane ═ 1: 2), and recrystallized using a mixed solvent of toluene and ethyl acetate to obtain 0.98g of the desired product as a white powder in a yield of 70%. The synthetic scheme is shown below.

[ chemical formula 38]

0.83g of the obtained powder was purified by sublimation using a gradient sublimation method. Sublimation purification was performed by heating at 330 ℃ under a pressure of 3.3Pa and an argon flow rate of 5.0 mL/min. After purification by sublimation, 0.71g of white powder was obtained in a recovery rate of 85%.

Further, FIG. 14 shows the compound obtained¹H NMR spectrum, numerical data are shown below. As a result, it was found that the organic compound PaBC2N according to one embodiment of the present invention was obtained in the present synthesis example.

¹H NMR(DMSO-d6，300MHz)：＝7.27-7.40(m，6H)，7.48-7.61(m，6H)，7.68-7.84(m，14H)，8.03-8.06(m，2H)，8.11(d，J＝8.4Hz，2H)，8.46(d，J＝8.7Hz，2H)，8.52(d，J＝1.2Hz，2H)

Ultraviolet-visible absorption spectrum (hereinafter referred to as "absorption spectrum") and emission spectrum of the toluene solution and solid film of PaBC2N were measured. Next, the absorption spectrum and emission spectrum of the toluene solution and solid film of PaBC2N were measured. A solid thin film was formed on a quartz substrate by a vacuum evaporation method. The measurement of the absorption spectrum was carried out using an ultraviolet-visible spectrophotometer (solution: V-550 manufactured by Nippon spectral Co., Ltd., film: U-4100 manufactured by Hitachi High-technologies corporation). Note that the absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured by putting only toluene in a quartz cell, and the absorbance (-lo) was obtained from the transmittance and reflectance including the substrateg₁₀[％T/(100-％R)]The absorption spectrum of the film was calculated. Note that,% T represents transmittance, and% R represents reflectance. Further, the emission spectrum was measured using a fluorescence spectrophotometer (FS 920 manufactured by hamamatsu photonics corporation).

Fig. 15 shows an absorption spectrum and an emission spectrum of the toluene solution, and fig. 16 shows an absorption spectrum and an emission spectrum of the thin film.

In FIG. 15, the toluene solution of PaBC2N has absorption peaks at around 360nm and 317nm, and similarly, the peak of the emission wavelength is 408nm (excitation wavelength 360 nm). In fig. 16, the thin film of PaBC2N has absorption peaks at around 362nm, 345nm, 320nm, and 290nm, and similarly has a peak of emission wavelength at around 420nm (excitation wavelength 340 nm). In addition, PaBC2N was confirmed to emit blue light.

Further, it was found that the film of PaBC2N was less likely to aggregate even in the air, had a small change in morphology, and had good film quality.

The HOMO and LUMO levels of PaBC2N were calculated using Cyclic Voltammetry (CV) measurements. The calculation method is shown 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 (PTE platinum electrode manufactured by BAS corporation) was used as the working electrode, a platinum electrode (Pt counter electrode (5cm) for VC-3, manufactured by BAS Inc.) was used as the auxiliary electrode, and Ag/Ag was used as the reference electrode⁺An electrode (RE 7 non-aqueous solution reference electrode manufactured by BAS corporation). Note that the measurement was performed at room temperature (20 ℃ or higher and 25 ℃ or lower). The scanning speed during CV measurement was set to 0.1V/sec, and the oxidation potential Ea [ V ] with respect to the reference electrode was measured]And a reduction potential Ec [ V ]]. Ea is the intermediate potential between the oxidation-reduction waves and Ec is the intermediate potential between the reduction-oxidation waves. Here, it is known that the potential energy of the reference electrode used in the present embodiment with respect to the vacuum level is-4.94 [ eV [ ]]Thus making use of the HOMO level [ eV](ii) LUMO energy level [ eV ] of-4.94-Ea]The HOMO level and LUMO level were determined for each of the two equations-4.94-Ec.

Furthermore, CV measurement was repeated 100 times, and the oxidation-reduction wave in the measurement of the 100 th cycle was compared with the oxidation-reduction wave in the measurement of the 1 st cycle to investigate the electrical stability of the compound.

The results show that: the HOMO level in the measurement of the oxidation potential Ea [ V ] of PaBC2N is-5.71 eV. On the other hand, the LUMO level in the measurement of the reduction potential Ec [ V ] is-2.21 eV. Further, from comparison of the waveforms after the 1 st cycle and the 100 th cycle in the repeated measurement of the oxidation-reduction wave, it was found that 94% of the peak intensity was maintained in the Ec measurement, and thus it was found that PaBC2N was an organic compound having very high reduction resistance.

[ example 2]

Synthesis example 2

In this example, a method for synthesizing an organic compound 12, 12' - (naphthalene-1, 4-diyl) bis (9-phenyl-9H-dibenzo [ a, c ] carbazole) (abbreviated as PacDBC2N) according to one embodiment of the present invention will be described in detail. The structural formula of PacDBC2N is shown below.

[ chemical formula 39]

Into a 200mL three-necked flask, 0.37g (1.3mmol) of 1, 4-dibromonaphthalene, 1.4g (2.6mmol) of 2- (9-phenyl-9H-dibenzo [ a, c ] carbazol-12-yl) -4,4, 5, 5, -tetramethyl-1, 3, 2, -dioxaborolan, 80mg (0.26mmol) of tri (o-tolyl) phosphine, and 0.82g (6.0mmol) of potassium carbonate were placed, and the atmosphere in the flask was replaced with nitrogen. To the mixture were added 13mL of toluene, 3.0mL of ethanol, and 2.0mL of water, and the mixture was stirred under reduced pressure to conduct degassing. To the mixture was added 30mg (0.13mmol) of palladium (II) acetate, and the mixture was refluxed at 80 ℃ for 4 hours under a nitrogen stream.

After stirring, the mixture was suction filtered to collect a solid. The solid was dissolved in heated toluene, and the solution was filtered through a suction filter using celite, alumina, and magnesium silicate. The solid obtained by concentrating the filtrate was washed with ethyl acetate to obtain 0.60g of a white solid of the objective compound in a yield of 62%. The following formula shows the synthesis scheme of the above synthesis method

[ chemical formula 40]

0.60g of the obtained white solid was purified by sublimation using a gradient sublimation method. Sublimation purification was performed by heating at 340 ℃ under a pressure of 3.4Pa and an argon flow rate of 5.0 mL/min. After purification by sublimation, 0.50g of a pale yellow solid was obtained in a recovery rate of 83%.

In addition, FIG. 17 shows the resultant pale yellow solid¹H NMR spectrum, numerical data are shown below. From the results, it was found that the organic compound PacDBC2N according to one embodiment of the present invention was obtained in the present synthesis example.

¹H NMR(CDCl₃，300MHz)：＝7.30-7.39(m，4H)，7.46-7.50(m，2H)，7.54-7.77(m，22H)，8.18-8.21(m，2H)，8.81-8.86(m，6H)，8.94(d，J＝8.1Hz，2H)

Next, the absorption spectrum and emission spectrum of the toluene solution and solid film of PacDBC2N were measured. A solid thin film was formed on a quartz substrate by a vacuum evaporation method. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (solution: V-550 manufactured by Nippon spectral Co., Ltd., film: U-4100 manufactured by Hitachi high and New technology). Note that the absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured by putting only toluene into a quartz cell, and the absorbance (-log) was obtained from the transmittance and reflectance including the substrate₁₀[％T/(100-％R)]The absorption spectrum of the film was calculated. Note that,% T represents transmittance, and% R represents reflectance. Further, the emission spectrum was measured using a fluorescence spectrophotometer (FS 920 manufactured by hamamatsu photonics corporation). FIG. 18 shows the absorption light of the resulting toluene solutionMeasurement of spectra and emission spectra. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. Fig. 19 shows the measurement results of the absorption spectrum and the emission spectrum of the solid thin film.

From the results of fig. 18, it is clear that the toluene solution of PacDBC2N has absorption peaks at about 375nm and 335nm and emission peaks at 423nm, 401nm, and 380nm (excitation wavelength 336 nm). From the results of fig. 19, it is understood that the solid thin film of PacDBC2N has absorption peaks at around 377nm, 358nm, 336nm, and 304nm, and emission peaks at around 432nm and 390nm (excitation wavelength 330 nm).

Further, it was found that the thin film of PacDBC2N was less likely to aggregate even in the air, had a small morphological change, and had good film quality.

The HOMO and LUMO levels of PacDBC2N were calculated using Cyclic Voltammetry (CV) measurements. The calculation method is the same as in example 1, and therefore, overlapping description is omitted.

The results show that: the HOMO level in the measurement of the oxidation potential Ea [ V ] of PacDBC2N was-5.73 eV. On the other hand, the LUMO level in the measurement of the reduction potential Ec [ V ] is-2.26 eV. Further, from comparison of the waveforms after the 1 st cycle and the 100 th cycle in the repeated measurement of the oxidation-reduction wave, it was found that the peak intensity of 95% was maintained in the Ec measurement, and thus it was found that PacDBC2N was an organic compound having very high reduction resistance.

[ example 3]

Synthesis example 3

In this example, a method for synthesizing an organic compound 10, 10' - (naphthalene-1, 4-diyl) bis (7-phenylbenzo [ c ] carbazole) (abbreviated as PcBC2N) according to one embodiment of the present invention will be described in detail. The structural formula of PcBC2N is shown below.

[ chemical formula 41]

A100 mL three-necked flask was charged with 0.51g (1.8mmol) of 1, 4-dibromonaphthalene, 1.6g (3.8mmol) of 2- (7-phenylbenzo [ c ] carbazol-10-yl) -4,4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan, 64mg (0.21mmol) of tri (o-tolyl) phosphine, 1.1g (7.6mmol) of potassium carbonate, 20mL of toluene, 4mL of water, and 4mL of ethanol. The mixture was stirred under reduced pressure to degas, and the air in the flask was replaced with nitrogen. To the mixture was added 22mg (99. mu. mol) of palladium (II) acetate, and the mixture was stirred at 80 ℃ for 7 hours under a nitrogen stream. After stirring, water was added to the resulting mixture, the organic layer and the aqueous layer were separated, and the aqueous layer was extracted with toluene. The extract solution and the organic layer were combined, washed with saturated brine, and then dried over magnesium sulfate. The mixture was filtered, and the filtrate was concentrated to give an oil. The oil was purified by silica gel column chromatography (developing solvent toluene: hexane ═ 1: 2) to obtain an oil. The methanol suspension of the obtained oily substance was irradiated with ultrasonic waves, and the solid was collected by suction filtration. The resulting solid was purified by High Performance Liquid Chromatography (HPLC) to give an oil. Methanol was added to the obtained oil, and the precipitated solid was collected to obtain 0.68g of a white powder in a yield of 53%. The synthetic scheme of the present synthesis is shown below.

[ chemical formula 42]

The obtained white powder (0.65 g) was purified by sublimation using a gradient sublimation method. Sublimation purification was performed by heating at 370 ℃ under a pressure of 3.2Pa and an argon flow rate of 5.0 mL/min. After sublimation purification, 0.45g of white powder was obtained with a recovery rate of 69%.

FIG. 20 shows the white powder obtained¹H NMR spectrum, numerical data are shown below. As a result, it was found that organic compound PcBC2N according to one embodiment of the present invention was obtained in the present synthesis example.

¹H NMR(CDCl₃，300MHz)：＝7.46-7.71(m，22H)，7.77(s，2H)，7.89(d，J＝9.0Hz，2H)，8.03(d，J＝7.2Hz，2H)，8.17-8.21(m，2H)，8.83-8.85(m，4H)

Next, the absorption spectrum and emission spectrum of the toluene solution and solid film of PcBC2N were measured. A solid thin film was formed on a quartz substrate by a vacuum evaporation method. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (solution: V-550 manufactured by Nippon spectral Co., Ltd., film: U-4100 manufactured by Hitachi high and New technology). Note that the absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured by putting only toluene into a quartz cell, and the absorbance (-log) was obtained from the transmittance and reflectance including the substrate₁₀[％T/(100-％R)]The absorption spectrum of the film was calculated. Note that,% T represents transmittance, and% R represents reflectance. Further, the emission spectrum was measured using a fluorescence spectrophotometer (FS 920 manufactured by hamamatsu photonics corporation).

Fig. 21 shows the measurement results of the absorption spectrum and the emission spectrum of the obtained toluene solution. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. Fig. 22 shows the measurement results of the absorption spectrum and the emission spectrum of the solid thin film.

In FIG. 21, the toluene solution of PcBC2N has absorption peaks at about 368nm and 333nm, and similarly, the emission wavelength peaks are 376nm and 400nm (excitation wavelength 335 nm). In FIG. 22, the thin film of PcBC2N has absorption peaks at about 374nm and 338nm, and similarly has a peak of emission wavelength at about 430nm (excitation wavelength 355 nm). In addition, PcBC2N was confirmed to emit blue light.

Further, it was found that the film of PcBC2N was less likely to aggregate even in the air, had a small morphological change, and had good film quality.

Next, the HOMO and LUMO levels of PcBC2N were calculated using Cyclic Voltammetry (CV) measurements. The calculation method is the same as in example 1, and therefore, overlapping description is omitted.

The results show that: the HOMO level in the measurement of the oxidation potential Ea [ V ] of PcBC2N is-5.73 eV. On the other hand, the LUMO level in the measurement of the reduction potential Ec [ V ] is-2.24 eV. Further, from comparison of the waveforms after the 1 st cycle and the 100 th cycle in the repeated measurement of the oxidation-reduction wave, it was found that the peak intensity of 83% was maintained in the Ea measurement and 82% was maintained in the Ec measurement, and thus it was found that PcBC2N was an organic compound having very high oxidation resistance and reduction resistance.

[ example 4]

Synthesis example 4

In this example, a method for synthesizing an organic compound 11-phenyl-8- [4- (9-phenylcarbazol-3-yl) -1-naphthyl ] benzo [ a ] carbazole (abbreviated as PCNPaBC), which is one embodiment of the present invention, will be described in detail. The structural formula of pcnpacbc is shown below.

[ chemical formula 43]

2.0g (4.5mmol) of 3- (4-bromo-1-naphthyl) -9-phenylcarbazole, 2- (11-phenylbenzo [ a ] carbazol-8-yl) -4,4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan, 2.3g (5.5mmol), 0.29g (0.94mmol) of tris (2-methylphenyl) phosphine, 2.8g (20mmol) of potassium carbonate, 45mL of toluene, 10mL of ethanol, and 10mL of water were placed in a 200mL three-necked flask. The mixture was stirred under reduced pressure to conduct deaeration, and the air in the flask was replaced with nitrogen. To the mixture was added 0.12g (0.53mmol) of palladium (II) acetate, and the mixture was stirred at 100 ℃ for 23 hours under a nitrogen stream. After stirring, the aqueous layer and the organic layer were separated, and then the aqueous layer was extracted with toluene. The obtained extract solution and the organic layer were combined, washed with saturated brine, and dried over magnesium sulfate. The resulting mixture was gravity filtered and the filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography (toluene: hexane ═ 3: 2), and recrystallized using a mixed solvent of ethyl acetate and methanol, thereby obtaining a solid. The obtained solid was purified by high-speed liquid chromatography (developing solvent: chloroform), and recrystallization was performed using a mixed solvent of ethyl acetate and methanol, whereby 1.7g of the objective white solid was obtained in a yield of 58%. The synthetic scheme is shown below.

[ chemical formula 44]

1.7g of the obtained white solid was purified by sublimation using a gradient sublimation method. Sublimation purification was performed by heating at 320 ℃ under a pressure of 5.0Pa and an argon flow rate of 10 mL/min. After purification by sublimation, 0.64g of a white solid was obtained in a recovery rate of 38%.

FIG. 23 shows the white powder obtained¹H NMR spectrum, numerical data are shown below. As a result, it was found that the organic compound PCNPaBC according to one embodiment of the present invention was obtained in the present synthesis example.

¹H NMR(DMSO-d₆，300MHz)：＝7.26-7.84(m，25H)，8.01-8.06(m，2H)，8.11(d，J＝8.4Hz，1H)，8.35(d＝7.8Hz，1H)，8.45-8.51(m，3H)

Subsequently, the absorption spectrum and emission spectrum of the toluene solution of PCNPaBC and the solid film were measured. A solid thin film was formed on a quartz substrate by a vacuum evaporation method. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (solution: V-550 manufactured by Nippon spectral Co., Ltd., film: U-4100 manufactured by Hitachi high and New technology). Note that the absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured by putting only toluene into a quartz cell, and the absorbance (-log) was obtained from the transmittance and reflectance including the substrate₁₀[％T/(100-％R)]The absorption spectrum of the film was calculated. Note that,% T represents transmittance, and% R represents reflectance. Further, the emission spectrum was measured using a fluorescence spectrophotometer (FS 920 manufactured by hamamatsu photonics corporation).

Fig. 24 shows the measurement results of the absorption spectrum and the emission spectrum of the obtained toluene solution. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. Fig. 25 shows the measurement results of the absorption spectrum and the emission spectrum of the solid thin film.

In FIG. 24, the toluene solution of PCNPaBC has absorption peaks at about 358nm, 317nm, and 300nm, and the peak of the emission wavelength is 415nm (excitation wavelength 323 nm). In FIG. 25, the PCNPaBC thin film has absorption peaks at around 372nm, 362nm, and 319nm, and has a peak of emission wavelength at around 423nm (excitation wavelength 340 nm). The compound according to one embodiment of the present invention can also be used as a host material and a hole transporting material for a light-emitting substance and a fluorescent light-emitting substance in a visible region.

Further, it was found that the film of PCNPaBC was less likely to aggregate in the air, had a small change in morphology, and had good film quality.

Subsequently, the HOMO level and LUMO level of PCNPaBC were calculated by Cyclic Voltammetry (CV) measurement. The calculation method is the same as in example 1, and therefore, overlapping description is omitted.

The results show that: the HOMO energy level in the measurement of the oxidation potential Ea [ V ] of PCNPaBC is-5.70 eV. On the other hand, the LUMO level in the measurement of the reduction potential Ec [ V ] is-2.21 eV. Further, from comparison of waveforms after the 1 st cycle and the 100 th cycle in the repeated measurement of the oxidation-reduction wave, it was found that 99% of the peak intensity was maintained in the Ec measurement, and thus pcnpabb was an organic compound having very high reduction resistance.

[ example 5]

Synthesis example 5

In this example, a method for synthesizing an organic compound 7-phenyl-10- [4- (9-phenylcarbazol-3-yl) -1-naphthyl ] benzo [ c ] carbazole (abbreviated as PCNPcBC) according to one embodiment of the present invention will be described in detail. The structural formula of PCNPcBC is shown below.

[ chemical formula 45]

< step 1: synthesis of 10- [4- (9-phenylcarbazol-3-yl) -1-naphthyl ] benzo [ c ] carbazole >

2.0g (4.5mmol) of 3- (4-bromo-1-naphthyl) -9-phenyl-9H-carbazole, 1.9g (5.4mmol) of 2- (benzo [ c ] carbazol-10-yl) -4,4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan, 0.28g (0.91mmol) of tris (2-methylphenyl) phosphine, 1.5g (11mmol) of potassium carbonate, 45mL of toluene, 6mL of ethanol, and 6mL of water were placed in a 200mL three-necked flask. The mixture was stirred under reduced pressure to conduct deaeration, and the air in the flask was replaced with nitrogen. To the mixture was added 0.070g (0.31mmol) of palladium (II) acetate, and the mixture was stirred under a nitrogen stream at 80 ℃ for 6 hours and at 90 ℃ for 8 hours. After stirring, the organic layer and the aqueous layer were separated, and the aqueous layer was extracted with toluene. The obtained extraction solvent and the organic layer were combined, washed with saturated brine, and dried over magnesium sulfate. The resulting mixture was gravity filtered and the filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography (toluene: hexane ═ 11: 9), and recrystallization was performed using a mixed solvent of ethyl acetate and methanol, whereby 2.0g of the objective white solid was obtained in a yield of 76%. The synthetic scheme for step 1 is shown below.

[ chemical formula 46]

FIG. 26 shows the white solid obtained¹H NMR spectrum, numerical data are shown below.

¹H NMR(CDCl₃，300MHz)：＝7.30-7.35(m，1H)，7.48-7.75(m，18H)，7.91(d，J＝8.7Hz，1H)，8.02(d，J＝7.2Hz，1H)，8.12-8.20(m，3H)，8.36(d，J＝0.9Hz，1H)，8.58(s，1H)，8.75-8.78(m，2H)

< step 2: synthesis of 7-phenyl-10- [4- (9-phenylcarbazol-3-yl) -1-naphthyl ] benzo [ c ] carbazole (abbreviation: PCNPcBC) >

2.0g (3.3mmol) of 10- [4- (9-phenylcarbazol-3-yl) -1-naphthyl ] benzo [ c ] carbazole, 0.75mL (6.7mmol) of iodobenzene, 0.68g (7.0mmol) of sodium tert-butoxide, and 17mL of xylene were placed in a 100mL three-necked flask. The mixture was stirred under reduced pressure to conduct deaeration, and the air in the flask was replaced with nitrogen. To the mixture were added 0.40mL (0.13mmol) of a tri-tert-butylphosphine 10 wt% hexane solution and 0.074g (0.13mmol) of bis (dibenzylideneacetone) palladium (0), and the mixture was stirred at 150 ℃ for 14 hours under a nitrogen stream. After stirring, water was added to the resulting mixture, the organic layer and the aqueous layer were separated, and the aqueous layer was extracted with toluene. The obtained extract solution and the organic layer were combined, washed with saturated brine, and dried over magnesium sulfate. The resulting mixture was gravity filtered and the filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography (toluene: hexane ═ 1: 2), and recrystallized using a mixed solvent of ethyl acetate and methanol, whereby 1.8g of the objective white solid was obtained in a yield of 84%. The synthetic scheme for step 2 is shown below.

[ chemical formula 47]

1.8g of the obtained white solid was purified by sublimation using a gradient sublimation method. Sublimation purification was performed by heating at 340 ℃ under a pressure of 5.0Pa and an argon flow rate of 10 mL/min. After purification by sublimation, 1.1g of a white solid was obtained in a recovery rate of 61%.

Further, FIG. 27 shows the white solid obtained¹H NMR spectrum, numerical data are shown below. As a result, it was found that the organic compound PCNPcBC according to one embodiment of the present invention was obtained in the present synthesis example.

¹H NMR(CDCl₃，300MHz)：＝7.30-7.35(m，1H)，7.43-7.75(m，23H)，7.88(d，J＝9.3Hz，1H)，8.03(d，J＝7.8Hz，1H)，8.13-8.20(m，3H)，8.36(d，J＝0.9Hz，1H)，8.83-8.85(m，2H)

Subsequently, absorption spectra and emission spectra of a toluene solution of PCNPcBC and a solid film were measured. A solid thin film was formed on a quartz substrate by a vacuum evaporation method. Using an ultraviolet-visible spectrophotometer (solution: V-550 manufactured by Nippon spectral Co., Ltd., film: U-4100 manufactured by Hitachi high and New technology)And (4) measuring the received spectrum. Note that the absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured by putting only toluene into a quartz cell, and the absorbance (-log) was obtained from the transmittance and reflectance including the substrate₁₀[％T/(100-％R)]The absorption spectrum of the film was calculated. Note that,% T represents transmittance, and% R represents reflectance. Further, the emission spectrum was measured using a fluorescence spectrophotometer (FS 920 manufactured by hamamatsu photonics corporation).

Fig. 28 shows the measurement results of the absorption spectrum and the emission spectrum of the obtained toluene solution. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. Fig. 29 shows the measurement results of the absorption spectrum and the emission spectrum of the solid thin film.

In FIG. 28, the toluene solution of PCNPcBC has absorption peaks at around 369nm and 333nm, and the peak of the emission wavelength is 400nm (excitation wavelength 333 nm). In fig. 29, the film of PCNPcBC has absorption peaks at around 375nm and 336nm, and has a peak of emission wavelength at around 423nm (excitation wavelength 350 nm). In addition, it was confirmed that PCNPcBC emits blue light.

Further, it was found that the film of PCNPcBC was not easily aggregated in the air, and the film had a small change in morphology and good film quality.

Subsequently, the HOMO level and LUMO level of PCNPcBC were calculated by Cyclic Voltammetry (CV) measurement. The calculation method is the same as in example 1, and therefore, overlapping description is omitted.

The results show that: the HOMO energy level in the measurement of oxidation potential Ea [ V ] of PCNPcBC is-5.71 eV. On the other hand, the LUMO level in the measurement of the reduction potential Ec [ V ] is-2.26 eV. Further, from comparison of the waveforms after the 1 st cycle and the 100 th cycle in the repeated measurement of the oxidation-reduction wave, it was found that 82% of the peak intensity was maintained in the Ea measurement and 87% of the peak intensity was maintained in the Ec measurement, and thus PCNPcBC was an organic compound having very high oxidation resistance and reduction resistance.

[ example 6]

Synthesis example 6

In this example, a method for synthesizing an organic compound 7-phenyl-10- [5- (9-phenylcarbazol-3-yl) -1-naphthyl ] benzo [ c ] carbazole (abbreviated as 1, 5PCNPcBC) according to one embodiment of the present invention will be described in detail. The structural formula of 1, 5PCNPcBC is shown below.

[ chemical formula 48]

< step 1: synthesis of 10- [5- (9-phenylcarbazol-3-yl) -1-naphthyl ] benzo [ c ] carbazole >

2.0g (4.4mmol) of 3- (5-bromo-1-naphthyl) -9-phenylcarbazole, 1.8g (5.2mmol) of 2- (benzo [ c ] carbazol-10-yl) -4,4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan, 0.13g (0.44mmol) of tris (2-methylphenyl) phosphine, 1.5g (11mmol) of potassium carbonate, 43mL of toluene, 5mL of ethanol, and 5mL of water were placed in a 300mL three-necked flask. The mixture was stirred under reduced pressure to conduct deaeration, and the air in the flask was replaced with nitrogen. To the mixture was added 0.036g (0.16mmol) of palladium (II) acetate, and the mixture was stirred at 100 ℃ for 11 hours under a nitrogen stream. After stirring, the aqueous layer of the resulting mixture was extracted with toluene. The obtained extract solution and the organic layer were combined, washed with saturated brine, and the organic layer was dried over magnesium sulfate. The resulting mixture was gravity filtered and the filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography (toluene), and recrystallization was performed using a mixed solvent of ethyl acetate and methanol, whereby 2.0g of the objective white solid was obtained in a yield of 80%. The synthetic scheme for step 1 is shown below.

[ chemical formula 49]

FIG. 30 shows the white solid obtained¹H NMR spectrum, numerical data are shown below.

¹H NMR(CDCl₃，300MHz)：＝7.29-7.35(m，1H)，7.43-7.74(m，18H)，7.91(d，J＝9.0Hz，1H)，8.02(d，J＝7.2Hz，1H)，8.08(d，J＝8.1Hz，2H)，8.18(d，J＝7.8Hz，1H)，8.34(d，J＝1.5Hz，1H)，8.56(s，1H)，8.72-8.76(m，2H)

< step 2: synthesis of 7-phenyl-10- [5- (9-phenylcarbazol-3-yl) -1-naphthyl ] benzo [ c ] carbazole (abbreviation: 1, 5PCNPcBC) >

2.0g (3.5mmol) of 10- [5- (9-phenylcarbazol-3-yl) -1-naphthyl ] benzo [ c ] carbazole, 0.80mL (7.1mmol) of iodobenzene, 0.68g (7.1mmol) of sodium tert-butoxide, and 18mL of xylene were placed in a 100mL three-necked flask. The mixture was stirred under reduced pressure to conduct deaeration, and the air in the flask was replaced with nitrogen. To the mixture were added 0.30mL (0.098mmol) of a tri-tert-butylphosphine 10 wt% hexane solution and 0.043g (0.075mmol) of bis (dibenzylideneacetone) palladium (0), and the mixture was stirred at 150 ℃ for 7 hours under a nitrogen stream. After stirring, water was added to the resulting mixture, the organic layer and the aqueous layer were separated, and the aqueous layer was extracted with toluene. The obtained extract solution and the organic layer were combined, washed with saturated brine, and dried over magnesium sulfate. The resulting mixture was gravity filtered and the filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography (toluene: hexane ═ 1: 1), and recrystallization was performed twice using a mixed solvent of ethyl acetate and methanol and a mixed solvent of toluene and hexane, whereby 1.9g of the objective white solid was obtained in a yield of 84%. The synthetic scheme for step 2 is shown below.

[ chemical formula 50]

1.9g of the obtained white solid was purified by sublimation using a gradient sublimation method. Sublimation purification was performed by heating at 340 ℃ under a pressure of 5.0Pa and an argon flow rate of 5.0 mL/min. After purification by sublimation, 1.1g of a white solid was obtained in a recovery rate of 58%.

Further, FIG. 31 shows the white solid obtained¹H NMR spectrum shown belowAnd (6) outputting numerical data. As a result, it was found that the organic compound 1, 5PCNPcBC according to one embodiment of the present invention was obtained in the present synthesis example.

¹H NMR(CDCl₃，300MHz)：＝7.29-7.35(m，1H)，7.42-7.73(m，23H)，7.88(d，J＝8.7Hz，1H)，8.02(d，J＝7.2Hz，1H)，8.07-8.11(m，2H)，8.18(d，J＝7.8Hz，1H)，8.33(d，J＝1.5Hz，1H)，8.80-8.83(m，2H)

Next, the absorption spectrum and emission spectrum of the toluene solution of 1, 5PCNPcBC and the solid film were measured. A solid thin film was formed on a quartz substrate by a vacuum evaporation method. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (solution: V-550 manufactured by Nippon spectral Co., Ltd., film: U-4100 manufactured by Hitachi high and New technology). Note that the absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured by putting only toluene into a quartz cell, and the absorbance (-log) was obtained from the transmittance and reflectance including the substrate₁₀[％T/(100-％R)]The absorption spectrum of the film was calculated. Note that,% T represents transmittance, and% R represents reflectance. Further, the emission spectrum was measured using a fluorescence spectrophotometer (FS 920 manufactured by hamamatsu photonics corporation).

Fig. 32 shows the measurement results of the absorption spectrum and the emission spectrum of the obtained toluene solution. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. Fig. 33 shows the measurement results of the absorption spectrum and the emission spectrum of the solid thin film.

In FIG. 32, the toluene solution of 1, 5PCNPcBC had absorption peaks at around 369nm, 332nm, and 323nm, and the emission wavelengths were 375nm and 395nm (excitation wavelength: 333 nm). In fig. 33, the thin film of 1, 5PCNPcBC has absorption peaks at around 372nm and 334nm, and emission peaks at around 385nm and 407nm (excitation wavelength 330 nm).

Further, it was found that the film of 1, 5PCNPcBC was less likely to aggregate in the air, had a small change in morphology, and had good film quality.

Subsequently, the HOMO level and LUMO level of 1, 5PCNPcBC were calculated by Cyclic Voltammetry (CV) measurement. The calculation method is the same as in example 1, and therefore, overlapping description is omitted.

The results show that: the HOMO level in the measurement of the oxidation potential Ea [ V ] of 1, 5PCNPcBC is-5.76 eV. On the other hand, the LUMO level in the measurement of the reduction potential Ec [ V ] is-2.25 eV. Further, from comparison of the waveforms after the 1 st cycle and the 100 th cycle in the repeated measurement of the oxidation-reduction wave, it was found that 80% of the peak intensity was maintained in the Ea measurement and 88% of the peak intensity was maintained in the Ec measurement, and thus it was found that the oxidation resistance and the reduction resistance of 1, 5PCNPcBC were extremely high.

[ example 7]

In this example, a light-emitting element 1 as one embodiment of the present invention described in the embodiment and a comparative light-emitting element 1 as a light-emitting element of a comparative example will be described in detail. The structural formulae of the organic compounds used in the light-emitting element 1 and the comparative light-emitting element 1 are shown below.

[ chemical formula 51]

(method for manufacturing light-emitting element 1)

First, indium tin oxide (ITSO) containing silicon oxide was formed over a glass substrate by a sputtering method, thereby forming the anode 101. The thickness of the anode 101 was 70nm and the electrode area was 4mm²(2mm×2mm)。

Next, as a pretreatment for forming a light emitting element on the substrate, the surface of the substrate was washed with water, baked at 200 ℃ for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

Then, the pressure of the substrate introduced into the chamber is reduced to 10^-4In the vacuum vapor deposition apparatus of about Pa, vacuum baking was performed at 170 ℃ for 30 minutes in a heating chamber in the vacuum vapor deposition apparatus, and then the substrate was cooled for about 30 minutes.

Next, the substrate having the anode 101 formed thereon was fixed to a substrate holder provided in a vacuum evaporation apparatus so that the surface having the anode 101 formed thereon faced downward, and 8, 8' - (naphthalene-1, 4-diyl) bis (11-phenyl-11H-benzo [ a ] carbazole) (abbreviated as PaBC2N) represented by the above structural formula (i) and molybdenum oxide (VI) were co-evaporated on the anode 101 by an evaporation method using resistance heating, whereby the ratio by weight was 4: 2(═ PaBC 2N: molybdenum oxide) and a hole injection layer 111 was formed to a thickness of 10 nm.

Next, PaBC2N was vapor-deposited on the hole injection layer 111, and the hole transport layer 112 was formed to have a thickness of 30 nm.

Next, 7- [4- (10-phenyl-9-anthryl) phenyl ] -7H-dibenzo [ c, g ] carbazole represented by the above structural formula (ii) (abbreviated: cgDBCzPA) and N, N '-bis (3-methylphenyl) -N, N' -bis [3- (9-phenyl-9H-fluoren-9-yl) phenyl ] -pyrene-1, 6-diamine represented by the above structural formula (iii) (abbreviated: 1, 6mMemFLPAPrn) were co-evaporated, thereby producing a copolymer having a weight ratio of 1: the light-emitting layer 113 was formed to have a thickness of 25nm and 0.03(═ cgDBCzPA: 1,6 mMemFLPAPrn).

Then, 2- [3' - (dibenzothiophen-4-yl) biphenyl-3-yl ] dibenzo [ f, h ] quinoxaline (abbreviated as 2mDBTBPDBq-II) represented by the above structural formula (iv) was deposited on the light-emitting layer 113 in a thickness of 15nm, and 2, 9-bis (2-naphthyl) -4, 7-diphenyl-1, 10-phenanthroline (abbreviated as NBPhen) represented by the above structural formula (v) was deposited in a thickness of 10nm, thereby forming the electron-transporting layer 114.

After the electron transit layer 114 was formed, an electron injection layer 115 was formed by depositing lithium fluoride (LiF) to a thickness of 1nm, and then the cathode 102 was formed by depositing aluminum to a thickness of 200nm, thereby manufacturing the light-emitting element 1.

(method of manufacturing comparative light-emitting element 1)

The comparative light-emitting element 1 was produced in the same manner as in the light-emitting element 1 except that the PaBC2N used for the hole injection layer 111 and the hole transport layer 112 of the light-emitting element 1 was replaced with 3,3' - (naphthalene-1, 4-diyl) bis (9-phenyl-9H-carbazole) (abbreviated as PCzN2) represented by the structural formula (vi).

The following table shows the element structures of the light-emitting element 1 and the comparative light-emitting element 1.

[ Table 1]

In a glove box in a nitrogen atmosphere, sealing treatment (coating a sealing material around the element, UV treatment at the time of sealing, and heat treatment at a temperature of 80 ℃ for 1 hour) was performed using a glass substrate so that the light-emitting element 1 and the comparative light-emitting element 1 were not exposed to the atmosphere, and then initial characteristics of these light-emitting elements were measured. In addition, the measurement was performed at room temperature.

Fig. 34 shows luminance-current density characteristics of the light-emitting element 1 and the comparative light-emitting element 1, fig. 35 shows current efficiency-luminance characteristics, fig. 36 shows luminance-voltage characteristics, fig. 37 shows current-voltage characteristics, fig. 38 shows external quantum efficiency-luminance characteristics, and fig. 39 shows an emission spectrum. Table 2 shows luminance 1000cd/m²Nearby element characteristics.

[ Table 2]

As is apparent from fig. 34 to 38 and table 2, light-emitting element 1 according to one embodiment of the present invention using PaBC2N has higher light-emitting efficiency than comparative light-emitting element 1 using PCzN 2.

[ example 8]

In this example, the light-emitting element 2 as one embodiment of the present invention described in the embodiment and the comparative light-emitting element 2 as a light-emitting element of a comparative example will be described in detail. The structural formulae of the organic compounds used in the light-emitting element 2 and the comparative light-emitting element 2 are shown below.

[ chemical formula 52]

(method for manufacturing light-emitting element 2)

Next, the substrate provided with the anode 101 was fixed to a substrate holder provided in a vacuum vapor deposition apparatus such that the surface provided with the anode 101 faced downward, and 10, 10' - (naphthalene-1, 4-diyl) bis (7-phenylbenzo [ c ] carbazole) (abbreviated as: PcBC2N) represented by the structural formula (vii) and molybdenum oxide (VI) were co-deposited on the anode 101 by a vapor deposition method using resistance heating, whereby the weight ratio of the substrate to the substrate was 4: the hole injection layer 111 was formed to have a thickness of 10nm and 2(═ PcBC 2N: molybdenum oxide).

Next, PcBC2N was vapor-deposited on the hole injection layer 111, and the hole transport layer 112 was formed to a thickness of 30 nm.

Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 15nm, and 2, 9-bis (2-naphthyl) -4, 7-diphenyl-1, 10-phenanthroline (NBPhen for short) represented by the above structural formula (v) was deposited to a thickness of 10nm, thereby forming an electron transporting layer 114.

After the electron transit layer 114 was formed, an electron injection layer 115 was formed by depositing lithium fluoride (LiF) to a thickness of 1nm, and then the cathode 102 was formed by depositing aluminum to a thickness of 200nm, thereby manufacturing the light-emitting element 2.

(method of manufacturing comparative light-emitting element 2)

The comparative light-emitting element 2 was produced in the same manner as the light-emitting element 2 except that PcBC2N used for the hole injection layer 111 and the hole transport layer 112 of the light-emitting element 2 was replaced with 3,3' - (naphthalene-1, 4-diyl) bis (9-phenyl-9H-carbazole) (abbreviated as PCzN2) represented by the structural formula (vi).

The following table shows the element structures of the light-emitting element 2 and the comparative light-emitting element 2.

[ Table 3]

In a glove box in a nitrogen atmosphere, sealing treatment (coating a sealing material around the elements, UV treatment at the time of sealing, and heat treatment at a temperature of 80 ℃ for 1 hour) was performed using a glass substrate so that the light-emitting elements 2 and the comparative light-emitting elements 2 were not exposed to the atmosphere, and then initial characteristics of these light-emitting elements were measured. In addition, the measurement was performed at room temperature.

Fig. 40 shows luminance-current density characteristics of the light-emitting element 2 and the comparative light-emitting element 2, fig. 41 shows current efficiency-luminance characteristics, fig. 42 shows luminance-voltage characteristics, fig. 43 shows current-voltage characteristics, fig. 44 shows external quantum efficiency-luminance characteristics, and fig. 45 shows an emission spectrum. Table 4 shows luminance 1000cd/m²Nearby element characteristics.

[ Table 4]

As is clear from fig. 40 to 44 and table 2, light-emitting element 2 according to one embodiment of the present invention using PcBC2N emits good blue light with chromaticity of (0.14, 0.17), and has high efficiency characteristics, that is, external quantum efficiency thereof is 11.3%.

Further, FIG. 46 shows that the current density was 50mA/cm²Graph of luminance change versus driving time. As is clear from fig. 46, the light-emitting element 2 which is one embodiment of the present invention has a small decrease in luminance with the accumulation of driving time and a good lifetime.

[ example 9]

In this example, the light-emitting element 3 as one embodiment of the present invention described in the embodiment and the comparative light-emitting element 3 as a light-emitting element of a comparative example will be described in detail. The structural formulae of the organic compounds used for the light-emitting element 3 and the comparative light-emitting element 3 are shown below.

[ chemical formula 53]

(method for manufacturing light-emitting element 3)

Next, the substrate on which the anode 101 was formed was fixed to a substrate holder provided in a vacuum evaporation apparatus so that the surface on which the anode 101 was formed faced downward, and 11-phenyl-8- [4- (9-phenylcarbazol-3-yl) -1-naphthyl ] benzo [ a ] carbazole (abbreviated as PCNPaBC) represented by the structural formula (viii) and molybdenum oxide (VI) were co-evaporated on the anode 101 by a vapor deposition method using resistance heating, whereby the ratio by weight of the substrate to the substrate was 4: 2(═ pcnpabb: molybdenum oxide) and 10nm thick, the hole injection layer 111 was formed.

Next, pcnpabb was vapor-deposited on the hole injection layer 111, and the hole transport layer 112 was formed to have a thickness of 30 nm.

After the electron transit layer 114 was formed, an electron injection layer 115 was formed by depositing lithium fluoride (LiF) to a thickness of 1nm, and then the cathode 102 was formed by depositing aluminum to a thickness of 200nm, thereby manufacturing the light-emitting element 3.

(method of manufacturing comparative light-emitting element 3)

The comparative light-emitting element 3 was produced in the same manner as the light-emitting element 3 except that PCNPaBC used for the hole injection layer 111 and the hole transport layer 112 of the light-emitting element 3 was replaced with 3,3' - (naphthalene-1, 4-diyl) bis (9-phenyl-9H-carbazole) (abbreviated as PCzN2) represented by the structural formula (vi).

The following table shows the element structures of the light-emitting element 3 and the comparative light-emitting element 3.

[ Table 5]

In a glove box in a nitrogen atmosphere, sealing treatment (coating a sealing material around the elements, UV treatment at the time of sealing, and heat treatment at a temperature of 80 ℃ for 1 hour) was performed using a glass substrate so that the light-emitting elements 3 and the comparative light-emitting element 3 were not exposed to the atmosphere, and then initial characteristics of these light-emitting elements were measured. In addition, the measurement was performed at room temperature.

Fig. 47 shows luminance-current density characteristics of the light emitting element 3 and the comparative light emitting element 3, fig. 48 shows current efficiency-luminance characteristics, fig. 49 shows luminance-voltage characteristics, fig. 50 shows current-voltage characteristics, fig. 51 shows external quantum efficiency-luminance characteristics, and fig. 52 shows an emission spectrum. Table 6 shows luminance 1000cd/m²Nearby element characteristics.

[ Table 6]

As is clear from fig. 47 to 51 and table 6, the light-emitting element 3 according to one embodiment of the present invention using PCNPaBC has higher light-emitting efficiency than the comparative light-emitting element 3 using PCzN 2.

[ example 10]

In this example, the light-emitting element 4 as one embodiment of the present invention described in the embodiment and the comparative light-emitting element 4 as a light-emitting element of a comparative example will be described in detail. The structural formulae of the organic compounds used for the light-emitting element 4 and the comparative light-emitting element 4 are shown below.

[ chemical formula 54]

(method for manufacturing light-emitting element 4)

Next, the substrate on which the anode 101 was formed was fixed to a substrate holder provided in a vacuum evaporation apparatus so that the surface on which the anode 101 was formed faced downward, and 7-phenyl-10- [4- (9-phenylcarbazol-3-yl) -1-naphthyl ] benzo [ c ] carbazole (abbreviated as PCNPcBC) represented by the structural formula (ix) and molybdenum oxide (VI) were co-evaporated on the anode 101 by an evaporation method using resistance heating, whereby the ratio by weight of the substrate to the substrate holder was 4: 2(═ PCNPcBC: molybdenum oxide) and a hole injection layer 111 was formed to a thickness of 10 nm.

Next, PCNPcBC was vapor-deposited on the hole injection layer 111, and the hole transport layer 112 was formed to have a thickness of 30 nm.

After the electron transit layer 114 was formed, an electron injection layer 115 was formed by depositing lithium fluoride (LiF) to a thickness of 1nm, and then the cathode 102 was formed by depositing aluminum to a thickness of 200nm, thereby manufacturing the light-emitting element 4.

(method of manufacturing comparative light-emitting element 4)

The comparative light-emitting element 4 was produced in the same manner as the light-emitting element 4 except that PCNPcBC used for the hole injection layer 111 and the hole transport layer 112 of the light-emitting element 4 was replaced with 3,3' - (naphthalene-1, 4-diyl) bis (9-phenyl-9H-carbazole) (abbreviated as PCzN2) represented by the structural formula (vi).

The following table shows the element structures of the light-emitting element 4 and the comparative light-emitting element 4.

[ Table 7]

In a glove box in a nitrogen atmosphere, sealing treatment (coating a sealing material around the elements, UV treatment at the time of sealing, and heat treatment at a temperature of 80 ℃ for 1 hour) was performed using a glass substrate so that the light-emitting elements 4 and the comparative light-emitting elements 4 were not exposed to the atmosphere, and then initial characteristics of these light-emitting elements were measured. In addition, the measurement was performed at room temperature.

Fig. 53 shows luminance-current density characteristics of the light emitting element 4 and the comparative light emitting element 4, fig. 54 shows current efficiency-luminance characteristics, fig. 55 shows luminance-voltage characteristics, fig. 56 shows current-voltage characteristics, fig. 57 shows external quantum efficiency-luminance characteristics, and fig. 58 shows an emission spectrum. Table 8 shows luminance 1000cd/m²Nearby element characteristics.

[ Table 8]

As is apparent from fig. 53 to 57 and table 8, the light-emitting element 4 according to one embodiment of the present invention using PCNPcBC has high light-emitting efficiency equivalent to that of the comparative light-emitting element 4 using PCzN 2.

Further, FIG. 59 shows that the current density was 50mA/cm²Graph of luminance change versus driving time. As is clear from fig. 59, the light-emitting element 4 which is one embodiment of the present invention has a small decrease in luminance with the accumulation of driving time and a good life.

[ example 11]

Synthesis example 7

In this example, a method for synthesizing an organic compound 2,2' - (naphthalene-1, 4-diyl) bis (5-phenyl-5H-benzo [ b ] carbazole) (abbreviated as PbBC2N) according to one embodiment of the present invention will be described in detail. The structural formula of PbBC2N is shown below.

[ chemical formula 55]

1.0g (3.6mmol) of 1, 4-dibromonaphthalene, 3.3g (7.8mmol) of 2- (4, 4,5, 5-tetramethyl- [1, 3, 2] dioxaborolan-2-yl) -5H-benzo [ b ] carbazole, 0.11g (0.36mmol) of tris (2-methylphenyl) phosphine, 2.2g (16mmol) of potassium carbonate, 35mL of toluene, 8mL of ethanol, and 8mL of water were placed in a 200mL three-necked flask. The mixture was stirred under reduced pressure to conduct deaeration, and the air in the flask was replaced with nitrogen. To the mixture was added 60mg (0.27mmol) of palladium (II) acetate, and the mixture was stirred at 100 ℃ for 10 hours under a nitrogen stream. After stirring, the aqueous layer was extracted with toluene. The obtained extract solution and the organic layer were combined, washed with saturated brine, and the organic layer was dried over magnesium sulfate. The resulting mixture was gravity filtered and the filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography (toluene: hexane ═ 2: 1), and recrystallized using toluene/hexane, thereby obtaining a solid. The obtained solid was purified by high-speed liquid chromatography (developing solvent: chloroform), and recrystallization was performed using toluene/hexane, whereby 1.5g of the objective yellow solid was obtained in a yield of 58%. The synthetic scheme is shown below.

[ chemical formula 56]

1.4g of the obtained yellow solid was purified by sublimation using a gradient sublimation method. Sublimation purification was performed by heating 2,2' - (naphthalene-1, 4-diyl) bis (5-phenyl-5H-benzo [ b ] carbazole) at 355 ℃ under a pressure of 3.9Pa and an argon flow rate of 6 mL/min. After purification by sublimation, 0.75g of a yellow solid was obtained in 52% recovery.

Further, FIG. 60 shows the obtained yellow solid¹H NMR spectrum, numerical data are shown below. As a result, it was found that the organic compound PbBC2N according to one embodiment of the present invention was obtained in the present synthesis example.

¹H NMR(CDCl₃，300MHz)：＝7.40-7.58(m，10H)，7.69-7.80(m，14H)，7.90(d，J＝7.8Hz，2H)，8.08(d，J＝7.8Hz，2H)，8.17-8.19(m，2H)，8.48(d，J＝1.5Hz，2H)，8.65(s，2H)

Next, the absorption spectrum and emission spectrum of the toluene solution and solid film of PbBC2N were measured. A solid thin film was formed on a quartz substrate by a vacuum evaporation method. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (solution: V-550 manufactured by Nippon spectral Co., Ltd., film: U-4100 manufactured by Hitachi high and New technology). Note that the absorption spectrum of the solution was calculated by subtracting the absorption spectrum measured by putting only toluene into a quartz cell, and the absorbance (-log) was obtained from the transmittance and reflectance including the substrate₁₀[％T/(100-％R)]The absorption spectrum of the film was calculated. Note that,% T represents transmittance, and% R represents reflectance. Further, the emission spectrum was measured using a fluorescence spectrophotometer (FS 920 manufactured by hamamatsu photonics corporation).

Fig. 61 shows the measurement results of the absorption spectrum and the emission spectrum of the obtained toluene solution. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. Fig. 62 shows the measurement results of the absorption spectrum and the emission spectrum of the solid thin film.

In FIG. 61, the toluene solution of PbBC2N had absorption peaks at around 397nm, 378nm, 335nm, and 327nm, and similarly, the emission wavelength peaks were 409nm and 434nm (excitation wavelength 335 nm). In FIG. 62, the thin film of PbBC2N has absorption peaks at around 404nm, 382nm, 336nm, and 325nm, and similarly has emission wavelength peaks at around 421nm and 447nm (excitation wavelength 350 nm). The compound according to one embodiment of the present invention can also be used as a host material for a light-emitting substance and a fluorescent light-emitting substance in a visible region.

Further, it was found that the thin film of PbBC2N was less likely to aggregate even in the air, had a small morphological change and had good film quality.

Subsequently, the HOMO level and LUMO level of PbBC2N were calculated by Cyclic Voltammetry (CV) measurement. The calculation method is the same as in example 1, and therefore, overlapping description is omitted.

The results show that: the HOMO level in the measurement of the oxidation potential Ea [ V ] of PbBC2N was-5.59 eV. On the other hand, the LUMO level in the measurement of the reduction potential Ec [ V ] is-2.36 eV. Further, from comparison of the waveforms after the 1 st cycle and the 100 th cycle in the repeated measurement of the oxidation-reduction wave, it was found that 96% of the peak intensity was maintained in the Ea measurement and 95% of the peak intensity was maintained in the Ec measurement, and thus it was found that PbBC2N was very high in oxidation resistance and reduction resistance.

[ example 12]

In this example, the light-emitting element 5 described in the embodiment as a light-emitting element according to an embodiment of the present invention will be described in detail. The structural formula of the organic compound used for the light-emitting element 5 is shown below.

[ chemical formula 57]

(method for manufacturing light-emitting element 5)

Then, the pressure of the substrate introduced into the chamber is reduced to 10^-4In a vacuum deposition apparatus of about Pa, the temperature in a heating chamber in the vacuum deposition apparatus was set at 170 DEG CAfter vacuum baking for 30 minutes, the substrate was left to cool for about 30 minutes.

Next, the substrate on which the anode 101 was formed was fixed to a substrate holder provided in a vacuum evaporation apparatus so that the surface on which the anode 101 was formed faced downward, and 2,2' - (naphthalene-1, 4-diyl) bis (5-phenyl-5H-benzo [ b ] carbazole) (abbreviated as PbBC2N) represented by the structural formula (x) and NDP-9 (analytical house co., ltd., material serial No. 1S20170124) were co-evaporated on the anode 101 by a resistance heating evaporation method, whereby the weight ratio was 1: the hole injection layer 111 was formed to have a thickness of 10nm and 0.1(═ PbBC 2N: NDP-9).

Then, PbBC2N was deposited on the hole injection layer 111 to a thickness of 20nm, and 3,3' - (naphthalene-1, 4-diyl) bis (9-phenyl-9H-carbazole) (abbreviated as PCzN2) represented by the above structural formula (vi) was deposited on the hole injection layer 111 to a thickness of 10nm, thereby forming a hole transport layer 112.

Then, 7- [4- (10-phenyl-9-anthryl) phenyl ] -7H-dibenzo [ c, g ] carbazole represented by the above structural formula (ii) (abbreviated as cgDBCzPA) and N, N' - (pyrene-1, 6-diyl) bis [ (6, N-diphenylbenzo [ b ] naphtho [1,2-d ] furan) -8-amine ] (abbreviated as: 1, 6BnfAPrn-03) represented by the above structural formula (xi) were co-evaporated, whereby the ratio by weight was 1: the light-emitting layer 113 was formed to have a thickness of 25nm and 0.03(═ cgDBCzPA: 1,6 BnfAPrn-03).

After the electron transport layer 114 was formed, an electron injection layer 115 was formed by depositing LiF to a thickness of 1nm, and then the cathode 102 was formed by depositing aluminum to a thickness of 200nm, thereby manufacturing the light emitting element 5.

The following table shows an element structure of the light emitting element 5.

[ Table 9]

In a glove box under a nitrogen atmosphere, a sealing treatment (coating a sealing material around the element, UV treatment at the time of sealing, and heat treatment at a temperature of 80 ℃ for 1 hour) was performed using a glass substrate without exposing the light-emitting element 5 to the atmosphere, and then initial characteristics were measured. In addition, the measurement was performed at room temperature.

Fig. 63 shows luminance-current density characteristics of the light emitting element 5, fig. 64 shows current efficiency-luminance characteristics, fig. 65 shows luminance-voltage characteristics, fig. 66 shows current-voltage characteristics, fig. 67 shows external quantum efficiency-luminance characteristics, and fig. 68 shows an emission spectrum. Table 10 shows luminance 1000cd/m²Nearby element characteristics.

[ Table 10]

As is clear from fig. 63 to 67 and table 8, the light-emitting element 5 according to one embodiment of the present invention using PbBC2N has high light-emitting efficiency and high color purity.

[ description of 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, 116: charge generation layer, 117: p-type layer, 118: electron-relay layer, 119: electron injection buffer layer, 400: substrate, 401: first electrode, 403: EL layer, 404: second electrode, 405: sealing material, 406: sealing material, 407: sealing substrate, 412: pad, 420: IC chip, 501: anode, 502: cathode, 511: first light-emitting unit, 512: second light emitting unit, 513: charge generation layer, 601: driver circuit portion (source line driver circuit), 602: pixel portion, 603: driver circuit portion (gate line driver circuit), 604: sealing substrate, 605: sealing material, 607: space, 608: wiring, 609: FPC (flexible printed circuit), 610: element substrate, 611: switching FET, 612: current control FET, 613: first electrode, 614: insulator, 616: EL layer, 617: second electrode, 618: light-emitting element, 951: substrate, 952: electrode, 953: insulating layer, 954: partition wall layer, 955: EL layer, 956: an electrode, a 1001 substrate, a 1002 base insulating film, a 1003 gate insulating film, a 1006 gate electrode, a 1007 gate electrode, a 1008 gate electrode, a 1020 first interlayer insulating film, a 1021 second interlayer insulating film, an 1022 electrode, a 1024W first electrode, a 1024R first electrode, a 1024G first electrode, a 1024B first electrode, a 1025 partition wall, a 1028EL layer, a 1029 second electrode, a 1031 sealing substrate, a 1032 sealing material, a 1033 transparent base material, a 1034R red coloring layer, a 1034G green coloring layer, a 1034B coloring layer, blue, a 1035 black matrix, a 1036 protective layer, a 1037 third interlayer insulating film, a 1040 pixel portion, a 1041 driver circuit portion, a 1042 peripheral portion, 2001: outer shell, 2002: light source, 2100: robot, 2110: arithmetic device, 2101: illuminance sensor, 2102: microphone, 2103: upper camera, 2104: speaker, 2105: display, 2106: lower camera, 2107: obstacle sensor, 2108: moving mechanism, 3001: lighting device, 5000: shell, 5001: display portion, 5002: second display portion, 5003: speaker, 5004: LED lamp, 5005: operation keys, 5006: connection terminal, 5007: sensor, 5008: microphone, 5012: support portion, 5013: earphone, 5100: sweeping robot, 5101: display, 5102: camera, 5103: brush, 5104: operation button, 5150: portable information terminal, 5151: outer shell, 5152: display area, 5153: bend, 5120: garbage, 5200: display area, 5201: display area, 5202: display area, 5203: display area, 7101: housing, 7103: display unit, 7105: support, 7107: display unit, 7109: operation keys, 7110: remote controller 7201: main body, 7202: shell, 7203: display unit, 7204: keyboard, 7205: external connection port, 7206: pointing device, 7210: second display unit, 7401: housing, 7402: display section, 7403: operation button, 7404: external connection port, 7405: speaker, 7406: microphone, 7400: mobile phone, 9310: portable information terminal, 9311: display panel, 9313: hinge portion, 9315: outer casing

Claims

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

[ chemical formula 1]

A-L-B (GI)

(Note that, in the above general formula (G1), L represents a substituted or unsubstituted naphthalene-1, 4-diyl group or a substituted or unsubstituted naphthalene-1, 5-diyl group, and further, A represents a group represented by the following general formula (gA) and B represents a group represented by the following general formula (gB))

[ chemical formula 2]

(Note that, in the above general formula (gA), Ar¹Represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. In addition, in R¹To R⁷In, R¹And R²、R⁴And R⁵、R⁵And R⁶And R⁶And R⁷At least one group of (b) is fused to form a benzene ring, and the others independently represent any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. In the above general formula (gB), Ar²Represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. In addition, R¹¹To R¹⁷Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. Note that R¹¹And R¹²、R¹⁴And R¹⁵、R¹⁵And R¹⁶And R¹⁶And R¹⁷They may also be fused to form a benzene ring. )

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

wherein L is represented by the following general formula (gL-1).

[ chemical formula 3]

(Note that, in the above general formula (gL-1), R⁴¹To R⁴⁶Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. )

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

wherein L is represented by the following general formula (gL-2).

[ chemical formula 4]

(Note that, in the above general formula (gL-2), R⁵¹To R⁵⁶Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. )

4. The organic compound according to any one of claims 1 to 3,

wherein in the group represented by the general formula (gA), R⁴And R⁵、R⁵And R⁶And R⁶And R⁷At least one group of (b) is fused to form a benzene ring.

5. The organic compound according to any one of claims 1 to 3,

wherein in the group represented by the general formula (gA), R⁴And R⁵And R⁶And R⁷At least one group of (b) is fused to form a benzene ring.

6. The organic compound according to any one of claims 1 to 3,

wherein the group represented by the general formula (gA) is a group represented by the following general formula (gA-1).

[ chemical formula 5]

(Note that, in the above general formula (gA-1), Ar¹Represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. In addition, R¹To R⁵And R²¹To R²⁴Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. )

7. The organic compound according to any one of claims 1 to 3,

wherein the group represented by the general formula (gA) is a group represented by the following general formula (gA-2).

[ chemical formula 6]

(Note that, in the above general formula (gA-2), Ar¹Represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. In addition, R¹To R³、R⁶、R⁷And R²⁵To R²⁸Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. )

8. The organic compound according to any one of claims 1 to 3,

wherein the group represented by the general formula (gA) is a group represented by the following general formula (gA-3).

[ chemical formula 7]

(Note that, in the above general formula (gA-3), Ar¹Represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. In addition, R¹To R³And R³¹To R³⁸Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. )

9. The organic compound according to any one of claims 1 to 8,

wherein Ar is¹Is phenyl.

10. The organic compound according to any one of claims 1 to 9,

wherein the group represented by the general formula (gA) and the group represented by the general formula (gB) have the same structure.

11. The organic compound according to any one of claims 1 to 10,

wherein the group represented by the general formula (gB) is a group represented by the following general formula (gB-1).

[ chemical formula 8]

(Note that, in the above general formula (gB), Ar²Represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. In addition, R¹¹To R¹⁷Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. )

12. The organic compound according to any one of claims 1 to 11,

wherein Ar is²Is phenyl.

13. An organic compound represented by the following general formula (G2).

[ chemical formula 9]

(Note that, in the above general formula (G2), Ar¹And Ar²Each independently represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. In addition, in R¹To R⁷In, R¹And R²、R⁴And R⁵、R⁵And R⁶And R⁶And R⁷At least one group of (b) is fused to form a benzene ring, and the others independently represent any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. In addition, in R¹¹To R¹⁷In, R¹¹And R¹²、R¹⁴And R¹⁵、R¹⁵And R¹⁶And R¹⁶And R¹⁷The aromatic ring may be fused to form a benzene ring, and the others independently represent any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. In addition, R⁴¹To R⁴⁶Each independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. )

14. The organic compound according to claim 13, wherein said organic compound,

wherein R is⁴And R⁵And R¹⁴And R¹⁵The groups of (a) are fused to form a benzene ring.

15. The organic compound according to claim 13, wherein said organic compound,

wherein R is⁶And R⁷And R¹⁶And R¹⁷The groups of (a) are fused to form a benzene ring.

16. The organic compound according to any one of claims 13 to 15,

wherein Ar is¹And Ar²Is phenyl.

17. A light-emitting element comprising the organic compound according to any one of claims 1 to 16.

18. A light-emitting element comprising the organic compound according to any one of claims 1 to 16 between an anode and a light-emitting layer.

19. A light-emitting element comprising the organic compound according to any one of claims 1 to 16 in a light-emitting layer.

20. An electronic device, comprising:

the light-emitting element according to any one of claims 17 to 19; and

sensors, operating buttons, speakers or microphones.

21. A light emitting device comprising:

the light-emitting element according to any one of claims 17 to 19; and

a transistor or a substrate.

22. An illumination device, comprising:

the light emitting device of claim 21; and

a housing.