Organic compound and electronic device

Abstract

To provide a new light-emitting element. A light-emitting element with high emission efficiency is provided. A light-emitting element with a long lifetime is provided. A light-emitting element with low driving voltage is provided.SOLUTION: A light-emitting element comprising: an anode; a cathode; and a layer containing an organic compound between the anode and the cathode, wherein the layer containing an organic compound comprises a first layer, a second layer, and a light-emitting layer in this order from the anode side, and the first layer comprises a first substance and a second substance, the first material has a HOMO level of greater than or equal to - 5. 8eV and less than or equal to - 5. 4eV, the second material has an electron-accepting property with respect to the first material, and the third material has a structure in which at least two substituents including carbazole rings are bonded to naphthalene rings.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] One embodiment of the present invention relates to a light-emitting element, a display module, a lighting module, a display device, a light-emitting element, a display module ... The present invention relates to an optical device, an electronic device, and a lighting device. The technical field of one embodiment of the invention disclosed in the present specification and the like is related to an object, a method, or a manufacturing method. Alternatively, one aspect of the present invention relates to a process, a machine, a manufacture It is about cha, or composition of matter. More specifically, the technical field of one embodiment of the present invention disclosed in this specification is a semiconductor device, a display, display devices, liquid crystal display devices, light-emitting devices, lighting devices, power storage devices, storage devices, imaging devices, and the like One example is a driving method or a manufacturing method thereof. [Background technology]

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

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

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

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

[0006] In Patent Document 1, a first hole injection layer is provided between a first hole transport layer in contact with the hole injection layer and a light emitting layer. Hole transport properties with a HOMO level between that of the interlayer and that of the host material A configuration for applying the material is disclosed.

[0007] The characteristics of light-emitting elements have improved dramatically, but there are still many issues regarding their efficiency, durability, and other characteristics. It must be said that this is still insufficient to meet the high level of demands that are being placed on the market. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] International Publication No. 2011 / 065136 Brochure Summary of the Invention [Problem to be solved by the invention]

[0009] In view of the above, an object of one embodiment of the present invention is to provide a novel light-emitting element. It is an object of the present invention to provide a light emitting element with good efficiency or a light emitting element with good life span. Another object is to provide a light-emitting element with a low driving voltage. .

[0010] In another embodiment of the present invention, a light-emitting device, an electronic device, and a display device each having high reliability are provided. Another object of the present invention is to provide a light-emitting device with low power consumption. The present invention aims to provide a device, an electronic device, and a display device.

[0011] The present invention is intended to solve any one of the above problems. [Means for solving the problem]

[0012] One aspect of the present invention is a device comprising an anode, a cathode, and an organic compound located between the anode and the cathode. The organic compound-containing layer includes, in order from the anode side, a first layer, a second layer, and a light-emitting layer, the first layer comprising a first material and a second material, the second layer comprising and a third substance, wherein the first substance has a HOMO level of -5.8 eV or more and -5.4 eV or more. The second substance is an organic compound having an electron transfer coefficient of 0.05 eV or less, and the ... The third substance is a substance having a septa property, and the third substance has a carbazole ring in a naphthalene ring. The light-emitting element is an organic compound having a structure in which at least two substituents are bonded.

[0013] Alternatively, another aspect of the present invention is a liquid crystal display device comprising an anode, a cathode, and an active element positioned between the anode and the cathode. The organic compound-containing layer includes a first layer and a second layer, in this order from the anode side. a second layer and a light-emitting layer, the first layer having a first material and a second material, The second layer has a third material, and the first material has a dibenzofuran ring or a dibenzofuran ring. the second substance is an aromatic amine having a substituent containing a thiophene ring, a substance having electron acceptor properties for the third substance, It is an organic compound having a structure in which at least two substituents having a carbazole ring are bonded. It is a light-emitting element.

[0014] Alternatively, another aspect of the present invention is a liquid crystal display device comprising an anode, a cathode, and an active element positioned between the anode and the cathode. The organic compound-containing layer includes a first layer and a second layer, in this order from the anode side. a second layer and a light-emitting layer, the first layer having a first material and a second material, The second layer has a third material, and the first material is an aromatic mono-olefin having a naphthalene ring. an amine, and the second substance has electron acceptor properties with respect to the first substance; and the third substance has at least one substituent having a carbazole ring on a naphthalene ring. The light-emitting element is an organic compound having a structure in which two fluorine atoms are bonded together.

[0015] Alternatively, another aspect of the present invention is a liquid crystal display device comprising an anode, a cathode, and an active element positioned between the anode and the cathode. The organic compound-containing layer includes a first layer and a second layer, in this order from the anode side. a second layer and a light-emitting layer, the first layer having a first material and a second material, The second layer has a third material, and the first material has a 9-fluorenyl group as an arylene group. an aromatic monoamine bonded to the nitrogen through a group, and the second substance is and the third substance has an electron acceptor property to the naphthalene ring. A light-emitting organic compound having a structure in which at least two substituents having a benzol ring are bonded. It is an element.

[0016] Alternatively, another aspect of the present invention is a method for manufacturing a semiconductor device according to the above-mentioned embodiment, wherein the first substance is N,N-bis(4 The light-emitting element is an organic compound having a (-biphenyl)amino group.

[0017] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein between the first layer and the second layer a third layer formed on the first layer, the third layer including a fourth substance, the fourth substance having a hole transporting property; The light-emitting element is an organic compound.

[0018] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein between the first layer and the second layer a third layer having a fourth material at its HOMO The light-emitting device is an organic compound with an energy level of -5.8 eV or more and -5.4 eV or less.

[0019] Alternatively, another aspect of the present invention is a method for manufacturing a semiconductor device having the above-described configuration, wherein the fourth substance and the first substance are It is a light-emitting element made of the same material.

[0020] Alternatively, another aspect of the present invention is a liquid crystal display device comprising an anode, a cathode, and an active element positioned between the anode and the cathode. The organic compound-containing layer includes a first layer and a second layer, in this order from the anode side. a light-emitting layer, the first layer comprising a third material and a second material, the second material is a substance having electron acceptor properties with respect to the third substance, and the third substance is A compound having a structure in which at least two substituents having a carbazole ring are bonded to a naphthalene ring. It is a light-emitting element that is an organic compound.

[0021] Alternatively, another embodiment of the present invention is a semiconductor device having the above structure, wherein the HOMO level of the third substance is The light emitting element has a capacitance of −5.8 eV or more and −5.6 eV or less.

[0022] Alternatively, in the above-described structure, another aspect of the present invention is a method for manufacturing a semiconductor device, wherein the third substance is represented by the following general formula (G1 ) is an organic compound represented by the formula (I).

[0023] [ka]

[0024] In the above general formula (G1), L is a substituted or unsubstituted naphthalene-1,4- A represents a diyl group or a substituted or unsubstituted naphthalene-1,5-diyl group. represents a group represented by the following general formula (gA), and B represents a group represented by the following general formula (gB).

[0025] [ka]

[0026] However, in the above general formula (gA), Ar 1 is a substituent having 6 to 13 carbon atoms forming a ring. represents a substituted or unsubstituted aryl group. 1 ~R 7 are independently hydrogen, carbon number an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a cycloalkyl group having 6 to 25 carbon atoms; represents a substituted or unsubstituted aryl group, provided that R 1 and R 2 , R 4 and R 5 , R 5 and R 6 , and R 6 and R 7 condenses to form a benzene ring It's okay to do so.

[0027] In addition, in the general formula (gB), Ar 2 is a substituent having 6 to 13 carbon atoms forming a ring or an unsubstituted aryl group. 11 ~R 17 are independently hydrogen, carbon, an alkyl group having 1 to 6 prime numbers, a cycloalkyl group having 3 to 6 carbon atoms, or a cycloalkyl group having 6 to 10 carbon atoms; 25 represents a substituted or unsubstituted aryl group, provided that R 11 and R 12 , R 14 and R 15 , R 15 and R 16 , and R 16 and R 17 is condensed to Ben A Zene ring may be formed.

[0028] Alternatively, in the above-described structure, another aspect of the present invention is a method for manufacturing a semiconductor device, wherein the third substance is represented by the following general formula (G1 ) is an organic compound represented by the formula:

[0029] [ka]

[0030] In the above general formula (G1), L is represented by the following general formula (gL-1) or the following general formula ( gL-2), A represents a group represented by the following general formula (gA), B represents a group represented by the following general formula (gB).

[0031] [ka]

[0032] However, in the above general formula (gL-1), R 41 ~R 46are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a ring-forming group; The aryl group represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

[0033] In addition, in the above general formula (gL-2), R 51 ~R 56 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a ring-forming group; The aryl group represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

[0034] [ka]

[0035] However, in the above general formula (gA), Ar 1 is a substituent having 6 to 13 carbon atoms forming a ring. represents a substituted or unsubstituted aryl group. 1 ~R 7 are independently hydrogen, carbon number an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a cycloalkyl group having 6 to 25 carbon atoms; represents a substituted or unsubstituted aryl group, provided that R 1 and R 2 , R 4 oh Yobi R 5 , R 5 and R 6 , and R 6 and R 7 is condensed to form a benzene ring is also good.

[0036] In addition, in the general formula (gB), Ar 2 is a substituent having 6 to 13 carbon atoms forming a ring or an unsubstituted aryl group. 11 ~R17 are independently hydrogen, carbon, an alkyl group having 1 to 6 prime numbers, a cycloalkyl group having 3 to 6 carbon atoms, or a cycloalkyl group having 6 to 10 carbon atoms; 25 represents a substituted or unsubstituted aryl group, provided that R 11 and R 12 , R 14 and R 15 , R 15 and R 16 , and R 16 and R 17 is condensed to Ben A Zene ring may be formed.

[0037] Alternatively, in another aspect of the present invention, in the above-mentioned configuration, the third substance is 3,3'-(naphthalene). talen-1,4-diyl)bis(9-phenyl-9H-carbazole), or 3,3' -(naphthalene-1,5-diyl)bis(9-phenyl-9H-carbazole) It is an optical element.

[0038] Alternatively, another embodiment of the present invention is a semiconductor device having the above structure, wherein the second substance is an organic compound. It is a light-emitting element.

[0039] Another aspect of the present invention is a device having the above-described structure, wherein a sensor, an operation button, a speaker, or the like is provided. Or, it is an electronic device having a microphone.

[0040] Another embodiment of the present invention is a semiconductor device having the above structure, further comprising: It is a light emitting device having the above structure.

[0041] Another embodiment of the present invention is a lighting device having the above structure and a housing.

[0042] In this specification, the term "light-emitting device" includes an image display device using a light-emitting element. In addition, a connector, such as an anisotropic conductive film or TCP (Tape Carrier), is attached to the light emitting element. The module has a printed wiring board at the end of the TCP. The COG (Chip On Glass) method is used for the module or light emitting element. A module on which an IC (integrated circuit) is directly mounted may also be included in the light emitting device. , lighting fixtures, etc. may include a light-emitting device. [Effects of the Invention]

[0043] According to one embodiment of the present invention, a novel light-emitting element can be provided. Alternatively, a light-emitting element having good luminous efficiency can be provided. do.

[0044] In another embodiment of the present invention, a light-emitting device, an electronic device, and a display device each having high reliability are provided. In another embodiment of the present invention, a light-emitting device with low power consumption can be provided. An electronic device and a display device can each be provided.

[0045] The description of these effects does not preclude the existence of other effects. The embodiment does not necessarily have to have all of these effects. , the specification, drawings, claims, etc., and It is possible to extract other effects from the claims and other descriptions. [Brief explanation of the drawings]

[0046] [Figure 1] Schematic diagram of a light-emitting element. [Figure 2] 1 is a conceptual diagram of an active matrix light-emitting device. [Figure 3]1 is a conceptual diagram of an active matrix light-emitting device. [Figure 4] 1 is a conceptual diagram of an active matrix light-emitting device. [Figure 5] FIG. 1 is a conceptual diagram of a passive matrix light-emitting device. [Figure 6] FIG. [Figure 7] 1 is a diagram showing an electronic device. [Figure 8] 1 is a diagram showing an electronic device. [Figure 9] FIG. [Figure 10] FIG. [Figure 11] FIG. 2 is a diagram illustrating an in-vehicle display device and an illumination device. [Figure 12] 1 is a diagram showing an electronic device. [Figure 13] 1 is a diagram showing an electronic device. [Figure 14] 1 shows the luminance-current density characteristics of the light-emitting element 1 and the comparative light-emitting element 1. [Figure 15] Current efficiency-luminance characteristics of Light-emitting element 1 and comparative light-emitting element 1. [Figure 16] 1 shows the luminance-voltage characteristics of the light-emitting element 1 and the comparative light-emitting element 1. [Figure 17] Current-voltage characteristics of the light-emitting element 1 and the comparative light-emitting element 1. [Figure 18] 1 shows the external quantum efficiency-luminance characteristics of the light-emitting element 1 and the comparative light-emitting element 1. [Figure 19] 1 shows emission spectra of the light-emitting element 1 and the comparative light-emitting element 1. [Figure 20] Normalized luminance vs. time change characteristics of the light-emitting element 1 and the comparative light-emitting element 1. [Figure 21] 1 shows the luminance-current density characteristics of the light-emitting element 2 and the comparative light-emitting element 2. [Figure 22] Current efficiency-luminance characteristics of the light-emitting element 2 and the comparative light-emitting element 2. [Figure 23] luminance-voltage characteristics of the light-emitting element 2 and the comparative light-emitting element 2. [Figure 24] Current-voltage characteristics of the light-emitting element 2 and the comparative light-emitting element 2. [Figure 25]1 shows the external quantum efficiency-luminance characteristics of the light-emitting element 2 and the comparative light-emitting element 2. [Figure 26] 1 shows emission spectra of the light-emitting element 2 and the comparative light-emitting element 2. [Figure 27] Normalized luminance vs. time change characteristics of the light-emitting element 2 and the comparative light-emitting element 2. [Figure 28] 1 shows luminance-current density characteristics of the light-emitting element 3 and the comparative light-emitting element 3. [Figure 29] Current efficiency-luminance characteristics of the light-emitting element 3 and the comparative light-emitting element 3. [Figure 30] luminance-voltage characteristics of the light-emitting element 3 and the comparative light-emitting element 3. [Figure 31] Current-voltage characteristics of the light-emitting element 3 and the comparative light-emitting element 3. [Figure 32] 1 shows external quantum efficiency-luminance characteristics of the light-emitting element 3 and the comparative light-emitting element 3. [Figure 33] 1 shows emission spectra of the light-emitting element 3 and the comparative light-emitting element 3. [Figure 34] Normalized luminance vs. time change characteristics of the light-emitting element 3 and the comparative light-emitting element 3. [Figure 35] 1 shows luminance-current density characteristics of the light-emitting element 4 and the comparative light-emitting element 4. [Figure 36] Current efficiency-luminance characteristics of the light-emitting element 4 and the comparative light-emitting element 4. [Figure 37] luminance-voltage characteristics of the light-emitting element 4 and the comparative light-emitting element 4. [Figure 38] Current-voltage characteristics of the light-emitting element 4 and the comparative light-emitting element 4. [Figure 39] 1 shows external quantum efficiency-luminance characteristics of the light-emitting element 4 and the comparative light-emitting element 4. [Figure 40] 1 shows emission spectra of the light-emitting element 4 and the comparative light-emitting element 4. [Figure 41] Normalized luminance vs. time change characteristics of the light-emitting element 4 and the comparative light-emitting element 4. [Figure 42] Normalized luminance vs. time change characteristics of a light-emitting element and a comparative light-emitting element. [Figure 43] 1H NMR chart of YGTBi1BP. [Figure 44]Absorption and emission spectra of YGTBi1BP in toluene solution. [Figure 45] Absorption and emission spectra of YGTBi1BP in the thin film state. [Figure 46] 1H NMR chart of 4-[4'-(carbazol-9-yl)biphenyl-4-yl]-4'-biphenylamine. [Figure 47] 1H NMR chart of YGTBiβNB. [Figure 48] Absorption and emission spectra of YGTBiβNB in ​​toluene solution. [Figure 49] Absorption and emission spectra of YGTBiβNB in ​​a thin film state. [Figure 50] BBAFLP1H NMR chart. [Figure 51] BBAFLBi1H NMR chart. [Figure 52] mBBAFLP1H NMR chart. [Figure 53] mpBBAFLBi 1H NMR chart. [Figure 54] Absorption and emission spectra of mpBBAFLBi in toluene solution. [Figure 55] Absorption and emission spectra of mpBBAFLBi in the thin film state. [Figure 56] TPBiAβNB1H NMR chart. [Figure 57] Absorption and emission spectra of TPBiAβNB in ​​toluene solution. [Figure 58] Absorption and emission spectra of TPBiAβNB in ​​the thin film state. [Figure 59] TPBiAβNBi1H NMR chart. [Figure 60] Absorption and emission spectra of TPBiAβNBi in toluene solution. [Figure 61] Absorption and emission spectra of TPBiAβNBi in the thin film state. [Figure 62] BBAPβNB-031H NMR chart. [Figure 63] Absorption and emission spectra of BBAPβNB-03 in toluene solution. [Figure 64] Absorption and emission spectra of BBAPβNB-03 in a thin film state. [Figure 65] 1H NMR chart of YGTBi1BP-02. [Figure 66] Absorption and emission spectra of YGTBi1BP-02 in toluene solution. [Figure 67] Absorption and emission spectra of YGTBi1BP-02 in a thin film state. DETAILED DESCRIPTION OF THE INVENTION

[0047] Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. The present invention is not limited to the above description, and the form and details thereof may be changed without departing from the spirit and scope of the present invention. It will be readily apparent to those skilled in the art that various modifications may be made to the present invention. It should not be construed as being limited to the description of the embodiments.

[0048] (Embodiment 1) FIG. 1 shows a diagram illustrating a light-emitting element according to one embodiment of the present invention. The device has a first electrode 101, a second electrode 102, and an EL layer 103. The EL layer is a hole injection layer. The organic EL device has an injection layer 111 , a hole transport layer 112 , and an emission layer 113 .

[0049] In addition to these, the EL layer 103 in FIG. 1(A) and FIG. 1(B) may also include an electron transport Although the electron injection layer 114 and the electron injection layer 115 are shown in the figure, the configuration of the light emitting device is not limited to these. There is no.

[0050] The hole injection layer 111 contains a first substance and a second substance. The first substance has a HOMO quasi- The second substance is a substance having a potential of -5.8 eV or more and -5.4 eV or less. It is a substance that exhibits electron acceptor properties toward other substances.

[0051] The third substance contained in the hole transport layer 112 is a naphthalene ring having a carbazole ring. It is an organic compound having a structure in which at least two substituents are bonded.

[0052] The light-emitting element of the present invention having the above-described structure has good luminous efficiency and a long life. It can be an element.

[0053] The first substance is preferably an organic compound having a hole transporting property. Aromatic amines having a substituent containing a benzofuran ring or a dibenzothiophene ring, naphthalene Aromatic monoamines having an aryl ring, or 9-fluorenyl groups are bonded to the amines via arylene groups. The first substance may be an aromatic monoamine bonded to the nitrogen of the amine. A substance having an N-bis(4-biphenyl)amino group can be used to create a light-emitting element with a long life. As the first substance, specifically, N- (4-biphenyl)-6,N-diphenylbenzo[b]naphtho[1,2-d]furan-8 -amine (abbreviation: BnfABP), N,N-bis(4-biphenyl)-6-phenylbenzene Zo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf), 4,4'- Bis(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)-4''-furan N,N-bis(4-biphenyl)triphenylamine (abbreviation: BnfBB1BP), ) Benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: BBABnf(6)) , N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8-amine N,N-bis(4-biphenyl)benzo[b]naphtho[4-biphenyl] ... [2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4)), N,N-biphenylamine bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation Name: DBfBB1TP), N-[4-(dibenzothiophen-4-yl)phenyl]-N -phenyl-4-biphenylamine (abbreviation: ThBA1BP), 4-(2-naphthyl)- 4',4''-Diphenyltriphenylamine (abbreviation: BBAβNB), 4-[4-(2 -naphthyl)phenyl]-4',4''-diphenyltriphenylamine (abbreviation: BBA βNBi), 4,4'-diphenyl-4''-(6;1'-binaphthyl-2-yl)triphenyl Phenylamine (abbreviation: BBAαNβNB), 4,4'-diphenyl-4''-(7;1 '-Binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB-03), 4 ,4'-Diphenyl-4''-(7-phenyl)naphthyl-2-yltriphenylamine (Abbreviation: BBAPβNB-03), 4,4'-diphenyl-4''-(6;2'-binaf (2-ethyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B), 4,4'-diphenyl Nyl-4''-(7;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA (βN2)B-03), 4,4'-diphenyl-4''-(4;2'-binaphthyl-1- 4,4'-diphenyl-4''-yltriphenylamine (abbreviation: BBAβNαNB), -(5;2'-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB- 02), 4-(4-biphenylyl)-4'-(2-naphthyl)-4''-phenyltriflate phenylamine (abbreviation: TPBiAβNB), 4-(3-biphenylyl)-4'-[4-( 2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: mTPBiA βNBi), 4-(4-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4 ''-Phenyltriphenylamine (abbreviation: TPBiAβNBi), 4-phenyl-4' -(1-naphthyl)triphenylamine (abbreviation: αNBA1BP), 4,4'-bis(1 -naphthyl)triphenylamine (abbreviation: αNBB1BP), 4,4'-diphenyl-4 ''-[4'-(carbazol-9-yl)biphenyl-4-yl]triphenylamine (Abbreviation: YGTBi1BP), 4'-[4-(3-phenyl-9H-carbazole-9- YGTBi 1BP-02), 4-diphenyl-4'-(2-naphthyl)-4''-{9-(4-biphenyl) (phenylyl)carbazole}triphenylamine (abbreviation: YGTBiβNB), N-[4- (9-phenyl-9H-carbazol-3-yl)phenyl]-N-[4-(1-naphthyl) PCB NBSF), N,N-bis(4-biphenylyl)-9,9'-spirobi[9H-fluorene N,N-bis(1,1'-biphenyl-4-yl)amine (abbreviation: BBASF), (9H-fluorene)-9,9'-spirobi[9H-fluorene]-4-amine (abbreviation: BBASF(4) ), N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoro) fluoren-2-yl)-9,9'-spiro-bi(9H-fluoren)-4-amine (abbreviation: o FBiSF), N-(4-biphenyl)-N-(dibenzofuran-4-yl)-9,9- Dimethyl-9H-fluoren-2-amine (abbreviation: FrBiF), N-[4-(1-naphthyl) N-[3-(6-phenyldibenzofuran-4-yl)phenyl]- 1-Naphthylamine (abbreviation: mPDBfBNBN), 4-phenyl-4'-(9-phenyl (4-phenyl-)-fluoren-9-yltriphenylamine (abbreviation: BPAFLP), 3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFL P), 4-phenyl-4'-[4-(9-phenylfluoren-9-yl)phenyl] Biphenylamine (abbreviation: BPAFLBi), 4-phenyl-4'-(9-phenyl-9 H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4' -diphenyl-4''-(9-phenyl-9-H-carbazol-3-yl)triphenyl PCBBi1BP, 4-(1-naphthyl)-4'-(9-phenyl- 9H-Carbazol-3-yl)-triphenylamine (abbreviation: PCBANB), 4,4 '-Di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl) ester PCBNBB, N-phenyl-N-[4-(9-phenyl- 9H-carbazol-3-yl)phenyl]-spiro-9,9'-bifluorene-2-a Examples include PCBASF (abbreviation: PCBASF).

[0054] The second substance may be an inorganic compound or an organic compound. Examples of the second substance include transition metal oxides. or oxides of metals belonging to groups 4 to 8 in the periodic table, electron-withdrawing groups (especially fluorine) Organic compounds having halogen groups such as fluoro groups or cyano groups can be used. From the above substances, a substance that exhibits electron acceptor properties with respect to the first substance is appropriately selected. Just do it.

[0055] The transition metal oxides that can be used as the second substance include those of Group 4 or above in the periodic table. Oxides of metals belonging to Group 8 include vanadium oxide, niobium oxide, and tantalum oxide. oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, rhenium Titanium oxide, ruthenium oxide, zirconium oxide, hafnium oxide and Silver oxide and molybdenum oxide are preferred because they exhibit high acceptor properties. It is suitable because it is stable in the air, has low hygroscopicity, and is easy to handle.

[0056] The second substance has an electron-withdrawing group (halogen group or cyano group) that can be used as the second substance. The organic compound is 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroethane. Nodimethane (abbreviation: F4-TCNQ), chloranil, 2,3,6,7,10,11-hexyl Hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN ), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviation :F6-TCNNQ), 2-(7-dicyanomethylene-1,3,4,5,6,8,9,1 0-octafluoro-7H-pyren-2-ylidene)malononitrile, etc. In particular, electron-withdrawing groups are bonded to condensed aromatic rings with multiple heteroatoms, such as HAT-CN. Compounds containing an electron-withdrawing group (especially a fluoro group) are preferred because they are thermally stable. Radialene derivatives containing halogen groups or cyano groups have low electron acceptor properties. It is preferable because it is always high, specifically, α,α',α''-1,2,3-cyclopropanetri Ylidenetris[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile] ], α,α',α''-1,2,3-cyclopropanetriylidenetris[2,6-dic 3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], α ,α',α''-1,2,3-cyclopropanetriylidenetris[2,3,4,5,6 -pentafluorobenzeneacetonitrile].

[0057] In addition, inorganic compounds such as molybdenum oxide have better electron acceptability than the organic compounds mentioned above. In a light-emitting element in which the second substance is an organic compound, the HOMO of the first substance tends to be strong. If the level is deep (for example, deeper than -5.4 eV), the driving voltage increases and the lifetime decreases. However, the light-emitting device of the present invention is characterized in that such inconveniences are unlikely to occur.

[0058] Furthermore, the third substance has a HOMO level of -5.8 eV or more and -5.6 eV or less. This is also preferable because it facilitates hole injection into the light-emitting layer host having a deep HOMO level. This is particularly important when a blue fluorescent light-emitting layer is used as the light-emitting layer. When the light-emitting material exhibits blue fluorescence, the The band gap is required to be wider than that of blue light, and as a result, the HOMO level is deep. Therefore, when the HOMO level of the third substance is between -5.8 eV and -5.6 It is preferable that the width is less than 100 eV for hole injection into the light-emitting layer. Typical examples of wide-gap host materials include organic compounds with an anthracene skeleton. It can be obtained.

[0059] The LUMO level of the third substance is −2.4 eV or higher, preferably −2.2 eV or higher. If the thickness is large, electrons can be effectively prevented from escaping from the light-emitting layer, leading to an improvement in light-emitting efficiency. For the same reason, the difference between the LUMO level of the third substance and the LUMO level of the host material is is 0.3 eV or more, preferably 0.5 eV or more.

[0060] In addition, when the host material has an anthracene skeleton and a carbazole skeleton, the anthracene skeleton is particularly When the host material has a benzophenone skeleton and a dibenzocarbazole skeleton, the host material has high electron mobility. This reduces the driving voltage, but at the same time, the light-emitting layer becomes electron-rich. This reduces the recombination area and electrons escape from the light-emitting layer, resulting in a decrease in reliability. However, in the light-emitting element of one embodiment of the present invention, the light emission of the third substance as described above can be easily obtained. This problem can be overcome by the good hole injection properties into the layer.

[0061] The third substance is preferably an organic compound represented by the following general formula (G1). These compounds have a deep HOMO level and are excellent in hole injection into the light-emitting layer. Therefore, it is possible to make a more reliable light-emitting element. It will be possible to provide.

[0062] [ka]

[0063] In the above general formula (G1), L is a substituted or unsubstituted naphthalene-1,4- It represents a substituted or unsubstituted naphthalene-1,5-diyl group or a substituted or unsubstituted naphthalene-1,5-diyl group. is an unsubstituted naphthalene-1,4-diyl group or a substituted or unsubstituted naphthalene-1, The 5-diyl group can also be represented by the following general formula (gL-1) or general formula (gL-2): .

[0064] [ka]

[0065] However, in the above general formula (gL-1), R 41 ~R 46 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a ring-forming group; The aryl group represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

[0066] In addition, in the above general formula (gL-2), R 51 ~R 56 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a ring-forming group; The aryl group represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

[0067] In addition, R 41 ~R 46 Or, R 51 ~R 56 If all of is hydrogen, synthesis is simple. Yes, and preferable.

[0068] In the general formula (G1), A represents a group represented by the following general formula (gA), and B represents It represents a group represented by the following general formula (gB).

[0069] [ka]

[0070] However, in the above general formula (gA), Ar 1 is a substituent having 6 to 13 carbon atoms forming a ring. represents a substituted or unsubstituted aryl group. 1 ~R 7 are independently hydrogen, carbon number an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a cycloalkyl group having 6 to 25 carbon atoms; represents a substituted or unsubstituted aryl group, provided that R 1 and R 2 , R 4 oh Yobi R 5 , R 5 and R 6 , and R 6 and R 7 is condensed to form a benzene ring is also good.

[0071] In addition, in the general formula (gB), Ar 2 is a substituent having 6 to 13 carbon atoms forming a ring or an unsubstituted aryl group. 11 ~R 17 are independently hydrogen, carbon, an alkyl group having 1 to 6 prime numbers, a cycloalkyl group having 3 to 6 carbon atoms, or a cycloalkyl group having 6 to 10 carbon atoms; 25 represents a substituted or unsubstituted aryl group, provided that R 11 and R 12 , R 14 and R 15 , R 15 and R 16 , and R 16 and R 17 is condensed to Ben A Zene ring may be formed.

[0072] R 1 ~R 7 , R 11 ~R 17 , R 21 ~R 24 , R 25 ~R 28 and R 31 No To R 38 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, represents an alkyl group, 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, and an isopropyl group. group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, pentyl group , hexyl group, etc.; cycloalkyl groups having 3 to 6 carbon atoms include cyclopropyl groups, Substituted groups having 6 to 25 carbon atoms, such as cyclobutyl, cyclopentyl, and cyclohexyl groups Alternatively, the unsubstituted aryl group may be a phenyl group, a biphenyl group, a naphthyl group, a phenanthyl group, or the like. Tolyl group, anthryl group, triphenylenyl group, fluorenyl group, 9,9-diphenylfluorene group Examples of the electron-containing group include a fluorenyl group and a 9,9-spirobifluorenyl group. In order to suppress the development of transportability, among these exemplified groups, polyacenes with three or more rings should not be included. It is preferable that the aryl group is a aryl group.

[0073] In addition, when the substituted or unsubstituted aryl group having 6 to 25 carbon atoms has a substituent, The substituents include alkyl groups having 1 to 6 carbon atoms and cycloalkyl groups having 3 to 6 carbon atoms. Alternatively, an aryl group having 6 to 13 carbon atoms can be used. Specific examples of these include: Examples include methyl, ethyl, propyl, isopropyl, tert-butyl, and hexyl groups. Silyl group, cyclopropyl group, cyclohexyl group, phenyl group, tolyl group, naphthyl group, biphenyl group Examples include a phenyl group.

[0074] R 41 ~R 46 and R 51 ~R 56 are each independently hydrogen, a C1 to C6 an alkyl group, a cycloalkyl group having 3 to 6 carbon atoms, or a group having 6 or more carbon atoms forming a ring; The aryl group may be a substituted or unsubstituted aryl group having 1 to 13 carbon atoms, and specifically, an aryl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, and tert-butyl groups. t-butyl group, pentyl group, hexyl group, etc., as a cycloalkyl group having 3 to 6 carbon atoms; Examples of the cycloalkyl groups include cyclopropyl and cyclohexyl groups, which have 6 to 13 carbon atoms in the ring. The substituted or unsubstituted aryl group includes a phenyl group, a biphenyl group, a naphthyl group, a phenyl ... Examples include a phenanthryl group, an anthryl group, and a fluorenyl group.

[0075] In addition, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring may have a substituent. When the substituent is present, examples of the substituent include an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and the like. An alkyl group or an aryl group having 6 to 13 carbon atoms can be used. Specific examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, and a methyl group. ethyl group, hexyl group, cyclopropyl group, cyclohexyl group, phenyl group, tolyl group, Examples include a butyl group and a biphenyl group.

[0076] Also, Ar 1 and Ar 2 are each independently a substituted or unsubstituted ring having 6 to 13 carbon atoms forming a ring. or an unsubstituted aryl group, specifically a phenyl group, a naphthyl group, a biphenyl group, Fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, tert-butyl Examples of the alkyl group include a phenyl group, a tolyl group, and a trimethylphenyl group.

[0077] The third substance is 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl -9H-carbazole), or 3,3'-(naphthalene-1,5-diyl)bis(9- The light-emitting element made of phenyl-9H-carbazole can be an element with high luminous efficiency. This is preferable because it can be done easily.

[0078] In addition, the third substance, i.e., a naphthalene ring having a substituent with a carbazole ring, is Organic compounds with at least two bonded structures should be designed so that the HOMO level does not become too shallow. Preferably, the compound does not have a triarylamine skeleton.

[0079] The hole transport layer 112 may have a two-layer structure. In this case, the light-emitting layer At least two substituents having carbazole rings are bonded to the naphthalene ring in the layer adjacent to the layer. It is preferable to use an organic compound having the following structure. Since a small electron transport property can reduce the deterioration of the device, Preferably, the above polyacenes are not included.

[0080] In this case, the other layer on the hole injection layer side is a layer containing an organic compound having hole transport properties. The organic compound having hole transport properties has a HOMO level of -5.8 eV or more. Preferably, the organic compound has a molecular weight of 1000 eV or less. It is more preferable that the material is the same as that of the compound.

[0081] (Embodiment 2) Next, examples of the detailed structure and materials of the light-emitting element will be described. As described above, the optical element has a pair of electrodes, a first electrode 101 and a second electrode 102, and a plurality of layers between the electrodes. The EL layer 103 has, from at least the first electrode 101 side, It includes a hole injection layer 111 , a hole transport layer 112 and an emitting layer 113 .

[0082] The other layers included in the EL layer 103 are not particularly limited, and may include a hole injection layer, a hole transport layer, and the like. layer, electron transport layer, electron injection layer, carrier blocking layer, exciton blocking layer, charge generation layer, etc. , various layer structures can be applied.

[0083] The first electrode 101 is made of a metal, alloy, or conductive material having a large work function (specifically, 4.0 eV or more). It is preferable to form the film using a compound such as a carboxylic acid or a mixture thereof. For example, indium tin oxide (ITO), silicon Indium oxide-tin oxide and indium oxide-zinc oxide containing silicon or silicon oxide , indium oxide containing tungsten oxide and zinc oxide (IWZO), etc. These conductive metal oxide films are usually formed by sputtering, but they can also be formed by sol-gel deposition. It is also possible to fabricate it by applying a method such as a quartz crystal process. Zinc was produced using a target containing 1 to 20 wt% zinc oxide added to indium oxide. Also, tungsten oxide and zinc oxide are used. The indium oxide (IWZO) contains 0.5% tungsten oxide relative to the indium oxide. Sputtering was performed using a target containing 5-5 wt% of zinc oxide and 0.1-1 wt% of zinc oxide. It can also be formed by the method. In addition, gold (Au), platinum (Pt), nickel (Ni) , tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt ( Nitrides of metallic materials (e.g., titanium nitride), copper (Cu), palladium (Pd), or Graphene can also be used. Although typical materials for forming the anode have been listed above, in one embodiment of the present invention, hole injection The doping layer 111 contains an organic compound having hole transport properties and an electron acceptor for the organic compound. Since a composite material containing a substance exhibiting a high work function is used, the electrode material can be selected regardless of the work function. This can be done.

[0084] In this embodiment, the stacked structure of the EL layer 103 is as shown in FIG. In addition to the injection layer 111, the hole transport layer 112, and the light emitting layer 113, an electron transport layer 114 and an electron injection layer 1B, the hole injection layer 111 and the hole transport layer 115 are formed. 112, the light-emitting layer 113, the electron transport layer 114, the electron injection layer 115, the charge generation layer 1 Two types of structures having 16 will be explained. The materials constituting each layer are as follows: Let me show you in detail.

[0085] The hole injection layer 111 is made of an organic compound having a HOMO level of −5.8 eV or more and −5.4 eV or less. A first substance is a substance having electron acceptor properties with respect to the first substance. In one embodiment of the present invention, the second substance may be an inorganic compound or an organic compound. However, this is a more preferable configuration, particularly when the compound is an organic compound.

[0086] The first substance and the second substance have been described in detail in the first embodiment, so the description will be repeated. The details are omitted. Please refer to the relevant descriptions.

[0087] By forming the hole injection layer 111, the hole injection property is improved, and the driving voltage is small. Furthermore, organic compounds having electron acceptor properties can be easily vapor deposited. It is an easy-to-use material because it is easy to form a film.

[0088] The hole transport layer 112 is formed by containing a hole transport material. 0 -6 cm 2 In one embodiment of the present invention, the hole mobility is preferably 1 / Vs or more. As a material for the hole transport layer, there are few substituents having a carbazole ring on a naphthalene ring. The organic compound used has a structure in which two carbazole groups are bonded to the naphthalene ring. Regarding organic compounds having a structure in which at least two substituents having an alkyl ring are bonded, Since this has been described in detail in Form 1, repeated description will be omitted.

[0089] The hole transport layer 112 may have a two-layer structure. In this case, the light-emitting layer At least two substituents having carbazole rings are bonded to the naphthalene ring in the layer adjacent to the layer. It is preferable to use an organic compound having a structure similar to that described above. Since small transport properties can reduce the deterioration of devices, poly(ethylene glycol) compounds with three or more rings in the molecule are used. Preferably, no reassens are included.

[0090] The other layer is a layer containing an organic compound having a hole transporting property. The organic compounds that exhibit this property are those with a HOMO level of -5.8 eV or more and -5.4 eV or less. It is preferable that the organic compound is the same substance as the first substance. More preferable.

[0091] The light-emitting layer 113 is a layer containing a host material and a light-emitting material. Whether it is a phosphorescent material or a material that exhibits thermally activated delayed fluorescence (TADF), Furthermore, even if the layer is a single layer, different light-emitting materials may be included. Note that in one embodiment of the present invention, the light-emitting layer 113 may be a fluorescent layer. This is particularly suitable for use in a layer that emits blue fluorescent light. Cut.

[0092] In the light-emitting layer 113, materials that can be used as fluorescent materials include, for example: Examples include the following: Other fluorescent materials can also be used.

[0093] 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine PAP2BPy, 5,6-bis[4'-(10-phenyl-9-anthracene] N, N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl] )phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-biphenyl bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluorene 9-yl)phenyl]-pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPr n), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'- Diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carba 4'-(10-phenyl-9-anthryl)triphenylamine ( Abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-difluoromethyl) (phenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl Phenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazo Perylene, 2,5,8,11-tetra-tert- -butylperylene (TBP), 4-(10-phenyl-9-anthryl)-4'- (9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA PA), N,N''-(2-tert-butylanthracene-9,10-diyldi-4, 1-phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2 -anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: 2PCAPPA) , N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'- Triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), N,N,N', N',N'',N'',N''',N'''-Octaphenyldibenzo[g,p]chryse N-(9,10,15-tetraamine (abbreviation: DBC1), Coumarin 30, 10-Diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3- Amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)] [N,9-diphenyl-9H-carbazol-3-amine (abbreviated as 2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine] :2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N '-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,1 0-Bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-t Triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10-bis (1,1'-biphenyl-2-yl)-N-[4-(9H-carbazol-9-yl)phenyl] N,N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), ,9-triphenylanthracene-9-amine (abbreviation: DPhAPhA) Coumarin 545 T,N,N'-Diphenylquinacridone (abbreviation: DPQd), rubrene, 5,12-bi Bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BP T), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl- 4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-methyl 6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizidine] 4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5, 11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N' -Tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,1 0-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1, 1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij ]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitri (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7- Tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine -9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: D CJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]ethenyl} -4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2 ,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetramethyl- tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pi N,N'-diphenyl-4-ylidene}propanedinitrile (abbreviation: BisDCJTM), Phenyl-N,N'-(1,6-pyrene-diyl)bis[(6-phenylbenzo[b]naphthyl) 1,6BnfAPrn-03, etc. In particular, 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6Bn Condensed aromatic diamine compounds, such as pyrenediamine compounds like fAPrn-03 is preferable because it has a high hole trapping property, and is excellent in luminous efficiency and reliability.

[0094] In the light-emitting layer 113, materials that can be used as phosphorescent materials include, for example: The following are some examples:

[0095] Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H -1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III ) (abbreviation: [Ir(mpptz-dmp)3]), tris(5-methyl-3,4-diphenyl Iridium(III) (abbreviation: [Ir(Mpt z)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H -1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrptz-3 b) Organometallic iridium complexes with a 4H-triazole skeleton, such as 3), and tris [3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazol- Zolato]iridium(III) (abbreviation: [Ir(Mptz1-mp)3]), tris(1 -methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium (III) (abbreviation: [Ir(PrptZ1-Me)3]) Organometallic iridium complexes with fac-tris[(1-2,6-diisopropyl phenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir (iPrpmi)3]), tris[3-(2,6-dimethylphenyl)-7-methylimide Dazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmp and organometallic iridium complexes having an imidazole skeleton, such as impt-Me)3). Bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium( III) Tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4' ,6'-difluorophenyl)pyridinato-N,C 2’ ]Iridium(III) picolinate bis(2-[3',5'-bis(trifluoromethyl) fluoride] (abbreviation: FIrpic), Phenyl]pyridinato-N,C 2’}Iridium(III) picolinate (abbreviation: [Ir( CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyri[ Ginat-N,C 2’ ]Iridium(III) acetylacetonate (abbreviation: FIraca c) Organometallic iridates with phenylpyridine derivatives having electron-withdrawing groups as ligands These are compounds that exhibit blue phosphorescence, with wavelengths from 440 nm to It is a compound that has an emission peak at 520 nm.

[0096] Also, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)yl Ir(tBuppm)3), (acetylacetonato)bis(Ir(tBuppm)3) (6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mp pm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4- Phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(ac ac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenylpiperidinyl] [Ir(nbppm)2(acac)]), (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenyl [Pyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm)2(acac)] ), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(II I) (abbreviation: [Ir(dppm)2(acac)]) Organic metal iridium complexes and (acetylacetonato)bis(3,5-dimethyl-2-phenyl) Rupirazinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac) ]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyridine) Dinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]) Organometallic iridium complexes with pyrazine skeletons such as tris(2-phenylpyridinium) Nat-N,C 2’ ) Iridium(III) (abbreviation: [Ir(ppy)3]), bis(2- Phenylpyridinato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), bis(benzo[h]quinolinato)iridium (I II) Acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), tris(benzyl) Tribenzo[h]quinolinato)iridium(III) (abbreviation: [Ir(bzq)3]), tris (2-phenylquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(pq) 3]), bis(2-phenylquinolinato-N,C 2’ ) Iridium(III) acetylacetone Pyridine skeleton-containing compounds such as setonate (abbreviation: [Ir(pq)2(acac)]) In addition to organometallic iridium complexes, tris(acetylacetonato)(monophenanthroline)tetrahydrogen Rare earth metals such as rubium(III) (abbreviated as [Tb(acac)3(Phen)]) These are mainly compounds that exhibit green phosphorescence, with wavelengths ranging from 500 nm to 6 The emission peak is at 100 nm. The body is particularly preferred because it is remarkably excellent in reliability and luminous efficiency.

[0097] Also, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinyl] Nato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis [4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridine Ir(III) (abbreviation: [Ir(5mdppm)2(dpm)]), bis[4,6-di( Naphthalen-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) Organogold compounds with pyrimidine skeletons, such as [Ir(d1npm)2(dpm)] iridium complexes of the genus acetylacetonatobis(2,3,5-triphenylpyrazine) Iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2, 3,5-triphenylpyrazinate)(dipivaloylmethanato)iridium(III)(abbreviation Name: [Ir(tppr)2(dpm)]), (acetylacetonato)bis[2,3-bis (4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fd pq)2(acac)]), and organometallic iridium complexes with pyrazine skeletons such as Tris(1-phenylisoquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir (piq)3]), bis(1-phenylisoquinolinato-N,C 2’ ) Iridium (II I) Pyridyl acetylacetonate (abbreviation: [Ir(piq)2(acac)]) In addition to organometallic iridium complexes with iridium skeletons, 2,3,7,8,12,13,17,18 -octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP) Platinum complexes such as tris(1,3-diphenyl-1,3-propanedionato) (monophenyl Anthroline) europium(III) (abbreviation: [Eu(DBM)3(Phen)]), Tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthate) (Troline) europium(III) (abbreviation: [Eu(TTA)3(Phen)]) These are compounds that exhibit red phosphorescence and are The emission peak is between 0 nm and 700 nm. The rhodium complex emits red light with good chromaticity.

[0098] In addition to the phosphorescent compounds described above, known phosphorescent light-emitting materials may be selected and used. stomach.

[0099] TADF materials include fullerene and its derivatives, acridine and its derivatives, and eosin. Derivatives of magnesium (Mg), zinc (Zn), cadmium, etc. can also be used. (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (P d) and the like. Examples of the metal-containing porphyrin include: For example, the protoporphyrin-tin fluoride complex (SnF2(Pro to IX), mesoporphyrin-tin fluoride complex (SnF2(Meso IX)), Hematoporphyrin-tin fluoride complex (SnF2(Hemato IX)), Copropor Phyllin tetramethyl ester-tin fluoride complex (SnF2(Copro III-4M e)), octaethylporphyrin-tin fluoride complex (SnF2(OEP)), ethiop Porphyrin-tin fluoride complex (SnF2(Etio I)), octaethylporphyrin -platinum chloride complex (PtCl2OEP) and the like.

[0100] [ka]

[0101] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenyl)-4-phenyl-4-methyl-4-phenyl ... (phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine ( Abbreviation: PIC-TRZ) and 9-(4,6-diphenyl-1,3,5-triazine-2- yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzT zn), 9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl phenyl]-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzPT zn), 2-[4-(10H-phenoxazin-10-yl)phenyl]-4,6-difluoro Phenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4-(5-phenyl -5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1, 2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimethyl-9H-azabicyclo[4.2.1.2]phenyl) cridin-10-yl)-9H-xanthen-9-one (abbreviation: ACRXTN), bis[ 4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10'H-spiro[acridine-9,9 π-electron-rich heteroaromatic rings such as '-anthracene]-10'-one (abbreviation: ACRSA) A heterocyclic compound having both a π-electron-deficient heteroaromatic ring and a π-electron-deficient heteroaromatic ring can also be used. The compound has a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring, and therefore has electron transport properties. The π-electron rich heteroaromatic ring and the π-electron deficient heteroaromatic ring are preferable. The substance in which the heteroaromatic ring is directly bonded exhibits the donor property of the π-electron rich heteroaromatic ring and the π-electron deficient heteroaromatic ring. The acceptor properties of the heteroaromatic rings become stronger, and the energy difference between the S1 and T1 levels becomes smaller. Therefore, it is particularly preferable since thermally activated delayed fluorescence can be efficiently obtained. Instead of the toe-shaped heteroaromatic ring, an aromatic ring to which an electron-withdrawing group such as a cyano group is bonded may be used. stomach.

[0102] [ka]

[0103] The host material of the light-emitting layer may be a material having electron transport properties or a material having hole transport properties. A variety of carrier transport materials can be used.

[0104] As a material having hole transport properties, 4,4'-bis[N-(1-naphthyl)-N-phenyl] N,N'-bis(3-methylphenyl)-N, N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenyl]a 4-phenyl-4'-(9-phenylfluorene)biphenyl (abbreviation: BSPB), -9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9- (phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-fluoren-9-yl Phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine ( PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-chlor PCBBi1BP, 4-(1-naphtho-3-yl)triphenylamine (9-phenyl-9H-carbazol-3-yl)-4'-triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9 H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-di Methyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl] N-phenyl-N-[4-( 9-phenyl-9H-carbazol-3-yl)phenyl]-spiro-9,9'-bifluor Compounds with aromatic amine skeletons such as PCBASF (dichlorobenzofuran), 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)benzene 3,6-bis(3,5-diphenylphenyl)bis(3,6-diphenylbenzoyl)biphenyl (abbreviation: CBP) -9-phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl-9H -carbazole (abbreviated as PCCP), and ',4''-(Benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene phenyl-9-yl)dibenzothiophene (abbreviation: DBTFLP-III), 4-[ 4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzo Compounds with a thiophene skeleton, such as thiophene (abbreviated as DBTFLP-IV), and 4, 4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: D BF3P-II), 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)fluorene phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II) and other furan skeletons Among the above, compounds having an aromatic amine skeleton and Compounds having a rubazole skeleton have good reliability, high hole transport properties, and are easy to drive. This is preferable because it also contributes to voltage reduction.

[0105] Examples of materials having electron transport properties include bis(10-hydroxybenzo[h]quinolinol). Nat)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato) )(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8- Quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl) phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl) phenolato]zinc(II) (abbreviation: ZnBTZ) and other metal complexes, (4-tert-butylphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation :PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl) phenyl)-1,2,4-triazole (abbreviation: TAZ), 1,3-bis[5-(p-te rt-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl) phenyl]-9H-carbazole (abbreviation: CO11), 2,2',2''-(1,3,5 -benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TP BI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H -benzimidazole (abbreviation: mDBTBIm-II) Heterocyclic compounds and 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f ,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophene [f,h]quinoxaline (abbreviated as 2-phenyl-4-yl)biphenyl-3-yl)dibenzo[f,h]quinoxaline mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl)biphenyl 4,6-[(2-yl)-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq) -Bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPn P2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation Heterocyclic compounds with diazine skeletons such as 3,5 -Bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCz PPy), 1,3,5-tri[3-(3-pyridyl)-phenyl]benzene (abbreviation: Tm PyPB) and other heterocyclic compounds having a pyridine skeleton. Heterocyclic compounds with an azine skeleton and heterocyclic compounds with a pyridine skeleton have good reliability. In particular, heterocyclic compounds having a diazine (pyrimidine or pyrazine) skeleton are The electron transport property is high, and this contributes to reducing the driving voltage.

[0106] When a fluorescent substance is used as the light-emitting material, the host material is a compound having an anthracene skeleton. A material having an anthracene skeleton is preferably used as a host material for a fluorescent material. When used as a host material, it is possible to realize a light-emitting layer having good luminous efficiency and durability. The materials having an anthracene skeleton used as the material include a diphenylanthracene skeleton, In particular, a substance having a 9,10-diphenylanthracene skeleton is preferred because it is chemically stable. In addition, when the host material has a carbazole skeleton, the hole injection and transport properties are improved. However, a benzocarbazole skeleton in which a benzene ring is further condensed to a carbazole is preferred. When it contains carbazole, the HOMO becomes shallower by about 0.1 eV than that of carbazole, making it easier for holes to enter. In particular, when the host material contains a dibenzocarbazole skeleton, The HOMO is shallower than that of sol by about 0.1 eV, making it easier for holes to enter, and the hole transport Therefore, it is also preferable as a host material. Preferred are those having a 9,10-diphenylanthracene skeleton and a carbazole skeleton (or It is a substance that simultaneously has a benzocarbazole skeleton and a dibenzocarbazole skeleton. From the viewpoint of the hole injection and transport properties, a benzofluorene skeleton was used instead of a carbazole skeleton. A dibenzofluorene skeleton may also be used. Examples of such materials include 9-phenyl 3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole ( Abbreviation: PCzPA), 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H- Carbazole (abbreviation: PCPN), 9-[4-(10-phenyl-9-anthracenyl) phenyl]-9H-carbazole (abbreviation: CzPA), 7-[4-(10-phenyl-9 -anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBC zPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]-benzo[ b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-{ 4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4'-yl}anthracene In particular, CzPA, cgDBCzPA, 2mB nfPPA and PCzPA are the preferred choices because they exhibit very good properties.

[0107] The host material may be a mixture of a plurality of substances. When used, a material having an electron transporting property and a material having a hole transporting property may be mixed. It is preferable to mix a material having an electron transport property with a material having a hole transport property. Therefore, the transport property of the light-emitting layer 113 can be easily adjusted, and the recombination region can be easily controlled. The ratio of the content of the material having hole transport properties to the content of the material having electron transport properties can be The ratio of the material having electron transport properties to the material having electron transport properties may be 1:9 to 9:1.

[0108] Furthermore, these mixed materials may form an exciplex. The exciplex is formed to emit light that overlaps with the wavelength of the lowest energy absorption band of By selecting such a combination, energy transfer becomes smooth and light emission can be obtained efficiently. In addition, the use of this configuration is also preferable because the driving voltage is reduced.

[0109] The electron transport layer 114 is a layer containing a substance having an electron transport property. Examples of the electron-transporting material include those listed as the materials having electron-transporting properties that can be used as the host material. can be used.

[0110] Between the electron transport layer 114 and the second electrode 102, a lithium fluoride layer was formed as an electron injection layer 115. Lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), etc. A layer containing an alkali metal or alkaline earth metal or a compound thereof may be provided. The layer 115 is a layer made of a substance having an electron transporting property and containing an alkali metal or alkaline earth metal Alternatively, a material containing such a compound or an electride may be used. For example, a material in which a high concentration of electrons is added to a mixed oxide of calcium and aluminum is used. Quality, etc.

[0111] In addition, a charge generation layer 116 may be provided instead of the electron injection layer 115. By applying a potential, holes are generated in the layer in contact with the cathode side of the layer, and electrons are generated in the layer in contact with the anode side. The charge generation layer 116 is a layer into which electrons can be injected. The P-type layer 117 is made of a material that can form the hole injection layer 111 described above. It is preferable that the P-type layer 117 is formed using the composite material mentioned above. As the materials constituting the substrate, a film containing the above-mentioned acceptor material and a film containing a hole transport material are stacked. By applying a potential to the P-type layer 117, the electron transport layer 114 Electrons and holes are injected into the second electrode 102, which is the cathode, and the light-emitting element operates.

[0112] The charge generation layer 116 includes an electron relay layer 118 and an electron injection buffer layer 119 in addition to the P-type layer 117. Preferably, one or both of layers 119 are provided.

[0113] The electron relay layer 118 contains at least a substance having electron transport properties, and the electron injection buffer layer 1 The electrons are transferred smoothly by preventing the interaction between the P-type layer 117 and the P-type layer 119. The LUMO level of the substance having electron transport properties contained in the relay layer 118 is The LUMO level of the acceptor material in the electron transport layer 114 and the charge generation layer 116 It is preferable that the LUMO level of the electron relay layer 11 is between the LUMO level of the material contained in the adjacent layer. Specific energy levels of the LUMO level in the electron transporting materials used in 8 is set to -5.0 eV or more, preferably -5.0 eV or more and -3.0 eV or less. The electron-transporting material used in the electron relay layer 118 is a phthalocyanine-based material. It is preferred to use materials or metal complexes having metal-oxygen bonds and aromatic ligands.

[0114] The electron injection buffer layer 119 contains an alkali metal, an alkaline earth metal, a rare earth metal, and These compounds (alkali metal compounds (oxides such as lithium oxide, halides, lithium carbonate) Alkaline earth metal compounds (including carbonates such as titanium and cesium carbonate), alkaline earth metal compounds (oxides, halogens compounds of rare earth metals (including oxides, halides, carbonates) or compounds of rare earth metals (including oxides, halides, carbonates) It is possible to use a material with high electron injection properties, such as SiO 2 .

[0115] The electron injection buffer layer 119 is formed by containing a substance having an electron transporting property and a donor substance. When the donor material is an alkali metal, an alkaline earth metal, or a rare earth metal, and their compounds (alkali metal compounds (oxides such as lithium oxide, halides , including carbonates such as lithium carbonate and cesium carbonate), alkaline earth metal compounds (oxides, compounds of rare earth metals (including oxides, halides, carbonates) In addition to tetrathianaphthacene (abbreviated as TTN), nickelocene, decamethicone, An organic compound such as nickelocene can also be used. The electron transport layer 114 may be formed using the same material as that used for forming the electron transport layer 114 described above. This can be done.

[0116] The material forming the second electrode 102 is preferably one having a small work function (specifically, 3.8 eV or less). Bottom) Metals, alloys, electrically conductive compounds, and mixtures thereof can be used. Specific examples of such cathode materials include alkali metals such as lithium (Li) and cesium (Cs). Lithium metals, as well as magnesium (Mg), calcium (Ca), strontium (Sr), etc. Elements belonging to Group 1 or 2 of the Periodic Table of Elements, and alloys containing these elements (MgAg, Rare earth metals such as AlLi), europium (Eu), ytterbium (Yb) and the like, However, when the second electrode 102 and the electron transport layer are connected to each other, By providing an electron injection layer, it is possible to use Al, Ag, ITO, silicon, etc., regardless of the magnitude of the work function. Various conductive materials such as indium oxide-tin oxide containing silicon oxide or silicon oxide are used as the second These conductive materials can be used as the electrode 102. It is possible to form the film using dry methods such as inkjet printing, spin coating, etc. It may also be formed by a wet method using a sol-gel method, or by using a paste of a metal material. Alternatively, the layer may be formed by a wet method.

[0117] The EL layer 103 can be formed by various methods, including dry and wet methods. For example, vacuum deposition, gravure printing, offset printing, screen printing, etc. A printing method, an ink jet method, a spin coating method, or the like may also be used.

[0118] Furthermore, the above-mentioned electrodes or layers may be formed using different film formation methods.

[0119] The structure of the layer provided between the first electrode 101 and the second electrode 102 is the same as that described above. However, it is not limited to the above. The first electrode 101 and the second electrode 102 are arranged so as to suppress quenching caused by the A preferred configuration is one in which a light-emitting region where holes and electrons recombine is provided at a location away from O2.

[0120] Furthermore, recombination in the hole transport layer or electron transport layer in contact with the light-emitting layer 113, particularly in the light-emitting layer 113 The carrier transport layer close to the region suppresses energy transfer from excitons generated in the light-emitting layer. Therefore, the band gap is determined by the luminescent material that constitutes the luminescent layer or the luminescent material contained in the luminescent layer. It is preferable that the material be made of a substance having a band gap larger than the band gap of the material. Desirable.

[0121] Next, we will introduce light-emitting devices (such as stacked devices and tandem devices) that have a structure in which multiple light-emitting units are stacked. The embodiment of the light-emitting element (also referred to as a "light-emitting element") will be described with reference to FIG. 1(C). The light-emitting element has a plurality of light-emitting units between them. 1(C) has a structure similar to that of the EL layer 103 shown in FIG. The element is a light-emitting element having a plurality of light-emitting units, and is the light-emitting element shown in FIG. 1(A) or FIG. 1(B). An optical element can be said to be a light-emitting element having one light-emitting unit.

[0122] In FIG. 1C, a first light-emitting unit 511 and a second light-emitting unit 512 are disposed between the anode 501 and the cathode 502. The second light-emitting unit 512 is stacked, and the first light-emitting unit 511 and the second light-emitting unit A charge generating layer 513 is provided between the anode 501 and the cathode 502. These correspond to the first electrode 101 and the second electrode 102 in FIG. 1(A), respectively. The same as that described in the first light-emitting unit 51 can be applied. The first and second light-emitting units 512 may have the same or different configurations.

[0123] When a voltage is applied between the anode 501 and the cathode 502, the charge generating layer 513 generates a light emitting The electron-injecting unit has the function of injecting electrons into one light-emitting unit and holes into the other light-emitting unit. In 1(C), when a voltage is applied so that the anode potential is higher than the cathode potential, In this case, the charge generating layer 513 injects electrons into the first light-emitting unit 511 and Any material capable of injecting holes into the gate 512 may be used.

[0124] The charge generation layer 513 is formed to have the same structure as the charge generation layer 116 described in FIG. 1B. The composite material of an organic compound and a metal oxide has the properties of carrier injection, carrier transport, and the like. It has excellent electrical properties, making it possible to achieve low voltage and low current driving. When the anode side of the unit is in contact with the charge generating layer 513, the charge generating layer 513 is the light emitting unit. Since it can also function as a hole injection layer for the light-emitting unit, the light-emitting unit does not need to have a hole injection layer. Both are good.

[0125] In addition, when the electron injection buffer layer 119 is provided in the charge generation layer 513, the electron injection buffer Since the electron injection layer 119 plays the role of an electron injection layer in the light-emitting unit on the anode side, the light-emitting layer The unit does not necessarily need to have an electron injection layer.

[0126] Although the light-emitting element having two light-emitting units has been described in FIG. 1C, a light-emitting element having three or more light-emitting units may be used. The present invention can be similarly applied to a light-emitting element in which light-emitting units are stacked. As in the case of the light-emitting element according to the embodiment, a plurality of light-emitting units are disposed between a pair of electrodes, and a charge generating layer 513 By separating the layers, high brightness light emission is possible while keeping the current density low. It is possible to realize a long-life element. It is also possible to realize a light-emitting device that can be driven at a low voltage and consumes little power. It is possible.

[0127] In addition, by making the light-emitting color of each light-emitting unit different, the light-emitting element as a whole For example, a light-emitting element having two light-emitting units can be In this case, the first light-emitting unit emits red and green light, and the second light-emitting unit emits blue light. This makes it possible to obtain a light-emitting element that emits white light as a whole.

[0128] In addition, the EL layer 103, the first light-emitting unit 511, the second light-emitting unit 512, and Each layer such as the charge generating layer and the electrodes can be formed by, for example, a vapor deposition method (including a vacuum deposition method), a droplet discharge method (including an ink jet method), or the like. It can be formed by using methods such as ink jet printing, coating, and gravure printing. They can be used in a variety of applications, including low molecular weight materials, medium molecular weight materials (including oligomers and dendrimers), and or polymeric material.

[0129] (Embodiment 3) In this embodiment, a light-emitting device using the light-emitting element described in Embodiments 1 and 2 This article explains:

[0130] In this embodiment, a light-emitting element manufactured using the light-emitting element described in Embodiments 1 and 2 is The light-emitting device will be described with reference to FIG. 2. FIG. 2(A) is a top view showing the light-emitting device. 2(B) is a cross-sectional view taken along lines AB and CD in FIG. 2(A). The light emitting element is controlled by a driving circuit (source line driving circuit) shown by a dotted line. The display device includes a display circuit (gate line driver circuit) 601, a pixel section 602, and a driver circuit section (gate line driver circuit) 603. 604 is a sealing substrate, 605 is a sealing material, and the inside surrounded by the sealing material 605 is a space. It's now 607.

[0131] The lead wiring 608 is connected to the source line driver circuit 601 and the gate line driver circuit 603. The wiring is for transmitting signals, and the FPC (flexible printed circuit board) is the external input terminal. Video signal, clock signal, start signal, reset signal, etc. from the input circuit 609 Although only the FPC is shown here, this FPC has a printed wiring board. The light emitting device in this specification may be a light emitting device. This includes not only the device itself but also the state in which an FPC or PWB is attached to it. do.

[0132] Next, the cross-sectional structure will be described with reference to FIG. A source line driver circuit 601 and a pixel portion are formed. , one pixel in the pixel section 602 is shown.

[0133] The element substrate 610 may be a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, or the like. FRP (Fiber Reinforced Plastics), PVF (Polyvinyl It is made using a plastic substrate made of, for example, fluoride, polyester, or acrylic. That's fine.

[0134] The structure of the transistors used in the pixels and driver circuits is not particularly limited. The transistor may be a top-type transistor or a staggered type transistor. The transistor may be a gate type transistor or a bottom gate type transistor. The semiconductor material is not particularly limited, and examples thereof include silicon, germanium, silicon carbide, and nitride. Gallium or the like can be used. Alternatively, in-type metal oxides such as In-Ga-Zn-based metal oxides can be used. An oxide semiconductor containing at least one of tungsten, gallium, and zinc may be used.

[0135] The crystallinity of the semiconductor material used in the transistor is not particularly limited. A semiconductor having crystallinity (microcrystalline semiconductor, polycrystalline semiconductor, single crystal semiconductor, or a semiconductor having a partially crystalline region) When a semiconductor having crystallinity is used, the transistor This is preferable because it can suppress deterioration of the star characteristics.

[0136] Here, in addition to the transistors provided in the pixels and the driver circuits, It is preferable to use an oxide semiconductor for a semiconductor device such as a transistor. In particular, it is preferable to use an oxide semiconductor having a wider band gap than silicon. By using an oxide semiconductor with a wider band gap than silicon, the off-state of the transistor can be This can reduce the current in the

[0137] The oxide semiconductor preferably contains at least indium (In) or zinc (Zn). In addition, In-M-Zn oxides (where M is Al, Ti, Ga, Ge, Y, Zr, Sn, It is preferable that the oxide semiconductor contains an oxide represented by the formula (metal such as La, Ce or Hf). More preferable.

[0138] In particular, the semiconductor layer has a plurality of crystal portions, and the c-axes of the crystal portions are aligned with the surface on which the semiconductor layer is formed, Alternatively, the oxide is oriented perpendicular to the upper surface of the semiconductor layer and has no grain boundary between adjacent crystal portions. It is preferable to use a nitride semiconductor film.

[0139] By using such materials for the semiconductor layer, fluctuations in electrical characteristics are suppressed, resulting in high reliability. This makes it possible to realize a low-power transistor.

[0140] Furthermore, the transistor having the above-described semiconductor layer can be used as a transistor due to its low off-state current. It is possible to retain the charge stored in the capacitor for a long period of time through such a transistor. By applying a transistor to each pixel, the gradation of the image displayed in each display area can be maintained while driving It is also possible to shut down the circuit. As a result, electronic devices with extremely low power consumption can be realized. It can be realized.

[0141] For stabilizing the characteristics of the transistor, it is preferable to provide an underlayer film. Inorganic films such as silicon oxide film, silicon nitride film, silicon oxynitride film, and silicon nitride oxide film The insulating film can be formed as a single layer or a laminated layer. CVD (Chemical Vapor Deposition) method (Plasma CVD method) , thermal CVD method, MOCVD (Metal Organic CVD) method, etc.), ALD ( Formed using Atomic Layer Deposition (ALD), coating, printing, etc. It should be noted that the undercoat film need not be provided if it is not necessary.

[0142] The FET 623 indicates one of the transistors formed in the driving circuit section 601. The drive circuit is made up of various CMOS circuits, PMOS circuits, or NMOS circuits. In this embodiment, a driver integrated type in which a driving circuit is formed on a substrate is shown. However, this is not necessarily required, and the drive circuit can be formed externally rather than on the substrate. .

[0143] The pixel section 602 includes a switching FET 611, a current control FET 612 and its driver. The pixel is formed by a plurality of pixels including a first electrode 613 electrically connected to the drain. However, the present invention is not limited to this, and a pixel unit that combines three or more FETs and a capacitance element may also be used. good.

[0144] An insulator 614 is formed to cover the end of the first electrode 613. It can be formed by using a photosensitive acrylic resin film of a mold.

[0145] In order to improve the coverage of the EL layer and the like to be formed later, the insulating material 614 is For example, the material of the insulator 614 is When a positive photosensitive acrylic is used, the radius of curvature (0. It is preferable that the insulating material 614 has a curved surface with a thickness of 2 μm to 3 μm. Either a negative photosensitive resin or a positive photosensitive resin can be used.

[0146] An EL layer 616 and a second electrode 617 are formed on the first electrode 613. Here, the material used for the first electrode 613 functioning as an anode is a material having a work function of It is desirable to use a large material, for example, an ITO film or an indium-silicon-containing film. Indium tin oxide film, indium oxide film containing 2 to 20 wt% zinc oxide, titanium nitride film, In addition to single layer films such as ROM film, tungsten film, Zn film, and Pt film, titanium nitride film and aluminum film are also available. a titanium nitride film and an aluminum-based film; A three-layer structure with a silicon film can be used. The resistance is low, good ohmic contact can be achieved, and the electrode can also function as an anode. .

[0147] The EL layer 616 can be formed by a deposition method using a deposition mask, an inkjet method, or a spin coating method. The EL layer 616 is formed by various methods such as those described in the first and second embodiments. Other materials that make up the EL layer 616 include: It may be a low molecular weight compound or a high molecular weight compound (including an oligomer or dendrimer). .

[0148] Furthermore, a material used for the second electrode 617 formed on the EL layer 616 and functioning as a cathode As the material, materials with a small work function (Al, Mg, Li, Ca, or their alloys or compounds) It is preferable to use a material such as MgAg, MgIn, or AlLi. When the light generated in 6 is transmitted through the second electrode 617, the second electrode 617 is Thin metal films and transparent conductive films (ITO, indium tin oxide containing 2-20 wt% zinc oxide) It uses lamination of indium tin oxide containing indium and silicon, zinc oxide (ZnO, etc.) It's good to do that.

[0149] The first electrode 613, the EL layer 616, and the second electrode 617 form a light-emitting element. The light-emitting element is the light-emitting element described in Embodiment 1 and Embodiment 2. The pixel portion is formed with a plurality of light-emitting elements. Now, the light-emitting elements described in the first and second embodiments and light-emitting elements having other configurations will be described. Both the optical element and the optical element may be included.

[0150] Furthermore, the sealing substrate 604 is bonded to the element substrate 610 with a sealing material 605. A light emitting element is disposed in a space 607 surrounded by a sub-substrate 610, a sealing substrate 604, and a sealing material 605. 618 is provided. The space 607 is filled with a filler. In addition to being filled with inert gas (nitrogen, argon, etc.), it can also be filled with sealing material. A recess is formed in the sealing substrate, and a desiccant is placed there to prevent deterioration due to moisture. This is a preferable configuration because it can suppress the noise.

[0151] It is preferable to use epoxy resin or glass frit for the sealing material 605. It is desirable that these materials be as impermeable to moisture and oxygen as possible. Materials used for the sealing substrate 604 include glass substrates, quartz substrates, and FRP (Fiber Reinforced Plastics). reinforced plastics), PVF (polyvinyl fluoride), polyester A plastic substrate made of polyethylene or acrylic can be used.

[0152] Although not shown in Figure 2, a protective film may be provided on the second electrode. The protective film is an organic resin film. The exposed portion of the sealant 605 may be covered with a protective film. A protective film may be formed on the surfaces and sides of the pair of substrates, the sealing layer, the insulating layer, and the like. A rim layer, etc. may be provided over the exposed side surface.

[0153] The protective film can be made of a material that is difficult for impurities such as water to permeate. It is possible to effectively prevent impurities such as these from diffusing from the outside to the inside.

[0154] The materials that make up the protective film include oxides, nitrides, fluorides, sulfides, ternary compounds, and metals. Alternatively, polymers and the like can be used, for example, aluminum oxide, hafnium oxide, hafnium Lanthanum silicate, lanthanum oxide, silicon oxide, strontium titanate, tantalum oxide , titanium oxide, zinc oxide, niobium oxide, zirconium oxide, tin oxide, yttrium oxide , cerium oxide, scandium oxide, erbium oxide, vanadium oxide or indium oxide Materials containing hafnium, aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, titanium nitride, niobium nitride, molybdenum nitride, zirconium nitride, or gallium nitride, etc. Materials, nitrides containing titanium and aluminum, oxides containing titanium and aluminum , oxides containing aluminum and zinc, sulfides containing manganese and zinc, cerium and sulfides containing erbium and strontium, oxides containing erbium and aluminum, yttrium Materials containing oxides containing lithium and zirconium can be used.

[0155] The protective film can be formed using a film formation method that provides good step coverage. One such method is atomic layer deposition (ALD). The ALD method can be used to form protective materials. It is preferable to use it for films. By using the ALD method, it is possible to eliminate cracks, pinholes, etc. It is possible to form a protective film with reduced defects or with a uniform thickness. Damage to the processed member when forming the protective film can be reduced.

[0156] For example, by forming a protective film using the ALD method, it is possible to fabricate a surface with complex irregularities or a surface with a touch panel. A uniform protective film with few defects can be formed on the top, sides and back of the panel. .

[0157] As described above, the light-emitting element described in Embodiment 1 and Embodiment 2 was used to manufacture the semiconductor device. A light emitting device having such a structure can be obtained.

[0158] The light-emitting device in this embodiment includes the light-emitting element described in Embodiments 1 and 2. Since the organic EL element is used, a light emitting device having good characteristics can be obtained. The light-emitting elements described in Embodiments 1 and 2 have a long lifetime and are therefore highly reliable. In addition, the light emitting device according to the first and second embodiments can be provided with a good light emitting device. Since the light emitting device using the optical element has good light emitting efficiency, it is possible to make the light emitting device low in power consumption. is possible.

[0159] In FIG. 3, a light emitting element that emits white light is formed, and a colored layer (color filter) or the like is provided. 3A shows an example of a full-color light-emitting device. film 1002, gate insulating film 1003, gate electrodes 1006, 1007, 1008, first An interlayer insulating film 1020, a second interlayer insulating film 1021, a peripheral portion 1042, a pixel portion 1040, a driving The driving circuit section 1041, the first electrodes 1024W, 1024R, 1024G, 102 4B, a partition wall 1025, an EL layer 1028, a second electrode 1029 of the light-emitting element, and a sealing substrate 103 1, sealing material 1032, etc. are shown.

[0160] In addition, in FIG. 3(A), the colored layers (red colored layer 1034R, green colored layer 1034G, blue The colored layer 1034B is provided on a transparent substrate 1033. A transparent substrate 1 on which a colored layer and a black matrix are provided may be further provided. The colored layer and the black matrix are aligned and fixed to the substrate 1001. The dust 1035 is covered with an overcoat layer 1036. The light-emitting layer is where light does not pass through the colored layers and goes out, and the light passes through the colored layers of each color and goes out. The light that does not pass through the colored layer is white, and the light that passes through the colored layer is red, green, or blue. This allows images to be expressed using four color pixels.

[0161] In FIG. 3(B), the colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer An example in which a layer 1034B) is formed between the gate insulating film 1003 and the first interlayer insulating film 1020 As shown in the figure, the colored layer is provided between the substrate 1001 and the sealing substrate 1031. is also good.

[0162] In the light emitting device described above, light is taken in toward the substrate 1001 on which the FET is formed. The light emitting device has a bottom emission structure, but the light is taken in from the sealing substrate 1031 side. The light emitting device may have a top emission structure. A cross-sectional view of the light-emitting device is shown in FIG. 4. In this case, a substrate that does not transmit light is used as the substrate 1001. Until the connection electrode that connects the FET and the anode of the light-emitting element is fabricated, the bottom electrode is The third interlayer insulating film 1037 is then formed on the electrode 1. This insulating film may also serve as a planarizing layer. The insulating film 1037 may be formed using the same material as the second interlayer insulating film, or other known materials. This can be done.

[0163] The first electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting element are anodes. However, it may be a cathode. Also, a top-emission type light-emitting device as shown in Figure 4 In this case, it is preferable that the first electrode is a reflective electrode. The EL layer 103 has the same structure as that described in the first and second embodiments, In addition, the device structure is designed to obtain white light emission.

[0164] In the top emission structure shown in Figure 4, the colored layers (red colored layer 1034R, green colored layer The sealing is performed by a sealing substrate 1031 provided with a blue color layer 1034G and a blue color layer 1034B. The sealing substrate 1031 has a black matrix disposed between the pixels. A coloring layer (red coloring layer 1034R, green coloring layer 1034G, The blue colored layer 1034B and the black matrix 1035 are overcoat layers 1036 The sealing substrate 1031 may be covered with a light-transmitting substrate. In addition, although an example of full color display using four colors, red, green, blue, and white, has been shown here, There is no limitation, and full color display may be performed using four colors of red, yellow, green, and blue, or three colors of red, green, and blue. .

[0165] In a top-emission type light-emitting device, the microcavity structure can be suitably applied. The light-emitting device having a microcavity structure has a first electrode as a reflective electrode and a second electrode as a semi-transparent electrode. The transparent and semi-reflective electrodes are formed as a thin film. It has at least an EL layer, and at least a light-emitting layer that serves as a light-emitting region.

[0166] The reflectance of the reflective electrode for visible light is 40% to 100%, preferably 70% to 100%. %, and its resistivity is 1×10 -2 The film is assumed to be less than Ωcm. The semi-reflective electrode has a visible light reflectance of 20% to 80%, preferably 40% to 70%. , and its resistivity is 1×10 -2 It is assumed that the film has a resistance of Ωcm or less.

[0167] The light emitted from the light-emitting layer included in the EL layer is reflected by the reflective electrode and the semi-transparent and semi-reflective electrode. The sound is reflected and resonates.

[0168] The light-emitting element can be fabricated by changing the thickness of the transparent conductive film, the composite material, the carrier transport material, etc. This allows the optical distance between the reflective electrode and the semi-transmissive / semi-reflective electrode to be changed. Between the reflective electrode and the semi-transparent / semi-reflective electrode, the light of the resonating wavelength is strengthened and the light of the non-resonating wavelength is strengthened. It is possible to attenuate light of wavelengths.

[0169] The light reflected by the reflective electrode and returned (first reflected light) is semi-transmitted from the light emitting layer. The light that directly enters the semi-reflective electrode (first incident light) interferes greatly with the reflective electrode. The optical distance of the light-emitting layer is (2n-1)λ / 4 (where n is a natural number greater than or equal to 1, and λ is the amplified It is preferable to adjust the optical distance to a wavelength of the first light. By matching the phase of the reflected light with the phase of the first incident light, the light emitted from the light-emitting layer can be further amplified. do.

[0170] In the above configuration, even if the EL layer has a plurality of light-emitting layers, a single light-emitting For example, it may be combined with the configuration of the tandem light emitting device described above. In this case, a plurality of EL layers are provided on one light-emitting element with a charge generating layer sandwiched therebetween, and each EL layer is provided with a single Alternatively, a configuration in which a plurality of light-emitting layers are formed may be applied.

[0171] The microcavity structure makes it possible to enhance the front-direction emission intensity of specific wavelengths. This allows for lower power consumption. In the case of a light-emitting device that displays images using a single pixel, the yellow light emission not only improves brightness, but also Since a microcavity structure tailored to the wavelength of each color can be applied, it is possible to achieve light-emitting devices with excellent characteristics. It can be placed.

[0172] The light-emitting device in this embodiment includes the light-emitting element described in Embodiments 1 and 2. Since the organic EL element is used, a light emitting device having good characteristics can be obtained. The light-emitting elements described in Embodiments 1 and 2 have a long lifetime and are therefore highly reliable. In addition, the light emitting device according to the first and second embodiments can be provided with a good light emitting device. Since the light emitting device using the optical element has good light emitting efficiency, it is possible to make the light emitting device low in power consumption. is possible.

[0173] Up to this point, we have explained about active matrix light emitting devices, but from now on we will be talking about passive light emitting devices. A passive matrix light-emitting device will be described. 5A is a perspective view showing the light emitting device, and FIG. 5B) is a cross-sectional view of FIG. 5A cut along XY. In FIG. 5, on a substrate 951, An EL layer 955 is provided between the electrode 952 and the electrode 956. The ends of the electrode 952 are It is covered with an insulating layer 953. A partition wall layer 954 is provided on the insulating layer 953. The sidewalls of the partition layer 954 become thicker between one sidewall and the other sidewall as they approach the substrate surface. That is, the cross section of the partition wall layer 954 in the short side direction has a slope such that the gap between the partition walls becomes narrower. The bottom side (the side that faces the same direction as the surface direction of the insulating layer 953 and is in contact with the insulating layer 953) ) is the upper side (the side that faces in the same direction as the surface direction of the insulating layer 953 and does not come into contact with the insulating layer 953). In this way, by providing the partition layer 954, the length of the light-emitting element caused by static electricity or the like can be reduced. In addition, in the passive matrix type light emitting device, the present invention can be applied to the embodiment. a light-emitting device having high reliability using the light-emitting element described in Embodiment 1 or 2; A light-emitting device with low power consumption can be provided.

[0174] The light emitting device described above has a large number of minute light emitting elements arranged in a matrix. Since it is possible to control the light emission, it can be suitably used as a display device for displaying images. It is a device.

[0175] This embodiment mode can be freely combined with other embodiment modes.

[0176] (Fourth embodiment) In this embodiment, the light-emitting element described in Embodiment 1 and Embodiment 2 is used as a lighting device. An example of use will be described with reference to Fig. 6. Fig. 6(B) is a top view of the lighting device, and Fig. 6(A) is a This is a cross-sectional view taken along line ef in FIG. 6(B).

[0177] The lighting device of this embodiment is a light-transmitting substrate 400 serving as a support, on which a first The first electrode 401 is formed on the substrate 10. The first electrode 401 is the same as the first electrode 10 in the second embodiment. When light is extracted from the first electrode 401 side, the first electrode 401 is made of a transparent material. The material is formed from a material having the following properties.

[0178] A pad 412 for supplying a voltage to the second electrode 404 is formed on the substrate 400 .

[0179] An EL layer 403 is formed on the first electrode 401. The EL layer 403 is the same as that in the first embodiment. The configuration of the EL layer 103 in the second embodiment, or the light-emitting units 511 and 512 and the This corresponds to a configuration in which the charge generating layer 513 is combined. Please refer to.

[0180] The second electrode 404 is formed to cover the EL layer 403. When light is extracted from the first electrode 401 side, the second electrode 102 corresponds to the second electrode 102. The first electrode 404 is formed of a highly reflective material. The voltage is supplied by connecting

[0181] As described above, a light-emitting element having the first electrode 401, the EL layer 403, and the second electrode 404 is realized in this embodiment. The lighting device shown in the embodiment has the light emitting element having high luminous efficiency. Therefore, the lighting device in this embodiment can be a lighting device with low power consumption.

[0182] The substrate 400 on which the light emitting element having the above structure is formed and the sealing substrate 407 are sealed with a sealing material 4. The lighting device is completed by fixing and sealing using the sealant 40. Either one of the seal material 5 and 406 may be used. (not shown) can also be mixed with a desiccant, which can absorb moisture. This leads to improved reliability.

[0183] In addition, a part of the pad 412 and the first electrode 401 is extended outside the sealing materials 405 and 406. By providing this, it can be used as an external input terminal. An IC chip 420 equipped with the above may be provided.

[0184] As described above, the lighting device according to the present embodiment uses the EL element according to the first and second embodiments. The light emitting element described above is used, and a light emitting device with high reliability can be obtained. A light emitting device with low power consumption can be obtained.

[0185] (Embodiment 5) In this embodiment, the light-emitting element described in Embodiment 1 and Embodiment 2 is included as a part thereof. Examples of electronic devices will be described. The light-emitting elements described in Embodiments 1 and 2 have a long life. As a result, the light-emitting element described in this embodiment has a long life and is highly reliable. The device may be an electronic device having a reliable light emitting portion.

[0186] As an electronic device to which the light-emitting element is applied, for example, a television set (television or television) (also called revision receivers), monitors for computers, digital cameras, digital Video cameras, digital photo frames, mobile phones (also called mobile phones or mobile phone devices) ), portable game machines, personal digital assistants, audio playback devices, large game machines such as pachinko machines, etc. Specific examples of these electronic devices are listed below.

[0187] 7A shows an example of a television device. The television device includes a housing 710 A display unit 7103 is built into the housing 1. In this case, a stand 7105 is used to hold the housing The display unit 7103 can display images. The display portion 7103 is formed using the light-emitting element described in Embodiments 1 and 2. It is arranged in a risk-like pattern.

[0188] The television device can be operated using the operation switches on the housing 7101 or a separate remote control. This can be done by the remote control device 7110. This allows you to control the channel and volume, and the image displayed on the display unit 7103 In addition, the remote control operation device 7110 can be operated. A display portion 7107 for displaying information output from the

[0189] The television device is assumed to be equipped with a receiver, modem, etc. It can receive television broadcasts and can also communicate by wire or wireless via a modem. By connecting to a network, you can send and receive data in one direction (sender to receiver) or two directions (sender to receiver). It is also possible to communicate information between the recipient and the receiver, or between receivers themselves.

[0190] FIG. 7(B1) shows a computer, which includes a main body 7201, a housing 7202, a display portion 7203, and a keyboard. keyboard 7204, external connection port 7205, pointing device 7206, etc. This computer uses the light emitting elements described in the first and second embodiments as a matrix. The display portion 7203 is fabricated by arranging the pixels in a pixel-like manner. The computer may have a form as shown in FIG. 7(B2). The computer in FIG. 7(B2) , a keyboard 7204, and a pointing device 7206 are replaced with a second display unit 721. The second display portion 7210 is a touch panel type. Input is performed by operating the input display displayed on the input unit 7210 with a finger or a special pen. The second display portion 7210 can display not only input images but also other images. The display unit 7203 may also be a touch panel. The screen is connected by a hinge, which can cause scratches or breakage when storing or transporting the device. This also helps prevent problems such as damage.

[0191] FIG. 7C shows an example of a mobile terminal. The mobile phone is built in a housing 7401. In addition to the display unit 7402, operation buttons 7403, an external connection port 7404, a speaker 740 5, a microphone 7406, etc. The mobile phone 7400 is the same as that of the first embodiment. and the light-emitting elements described in Embodiment 2 are arranged in matrix in the display portion 7402. It has.

[0192] The mobile terminal shown in FIG. 7C allows users to input information by touching the display portion 7402 with a finger or the like. In this case, it is possible to make a call or create an email. Operations such as turning on / off the camera can be performed by touching the display portion 7402 with a finger or the like.

[0193] The screen of the display unit 7402 has three main modes. The first is a display mode that mainly displays images. The first mode is a display mode, and the second mode is an input mode that mainly inputs information such as characters. This is a display + input mode that combines two modes: display mode and input mode.

[0194] For example, when making a call or creating an email, the display unit 7402 is used to input characters. This is the main character input mode, and you can input characters displayed on the screen. It is preferable to display a keyboard or number buttons on most of the screen of the display portion 7402. Desirable.

[0195] In addition, the mobile terminal may include a sensor for detecting tilt, such as a gyro or acceleration sensor. By providing a device, the orientation of the mobile terminal (portrait or landscape) can be determined and the screen display of the display portion 7402 can be displayed. The display can be switched automatically.

[0196] The screen mode can be switched by touching the display portion 7402 or by operating the housing 7401. This is done by operating the button 7403. Also, depending on the type of image displayed on the display unit 7402, For example, if the image signal to be displayed on the display unit is a video signal, If it is data, the display mode is switched to, and if it is text data, the input mode is switched to.

[0197] In the input mode, the optical sensor of the display unit 7402 detects a signal and displays it. If there is no input by touch operation on the part 7402 for a certain period of time, the screen mode is changed to the input mode. Alternatively, the display mode may be switched from the normal mode to the display mode.

[0198] The display portion 7402 can also function as an image sensor. By touching the device with your palm or fingers and capturing an image of your palm print or fingerprint, you can authenticate your identity. In addition, a backlight that emits near-infrared light to the display unit or a sensing light that emits near-infrared light By using a source, it is also possible to image finger veins, palm veins, etc.

[0199] Note that the structure described in this embodiment mode may be obtained by appropriately combining the structures described in any of Embodiment Modes 1 to 4. They can be used in combination.

[0200] As described above, the scope of application of the light emitting device including the light emitting element according to the first and second embodiments is as follows: The range of applications is extremely wide, and this light emitting device can be applied to electronic devices in all fields. By using the light-emitting element described in Embodiment 1 and Embodiment 2, highly reliable electrons can be obtained. You can get the equipment.

[0201] FIG. 8(A) is a schematic diagram showing an example of a cleaning robot.

[0202] The cleaning robot 5100 has a display 5101 on the top surface and multiple The camera 5102, the brush 5103, and the operation button 5104 are also shown. However, the underside of the cleaning robot 5100 is provided with tires, a suction port, etc. The robot 5100 also has an infrared sensor, an ultrasonic sensor, an acceleration sensor, a piezo sensor, It is equipped with various sensors such as a sensor, a light sensor, and a gyro sensor. 100 is equipped with wireless communication means.

[0203] The cleaning robot 5100 moves by itself, detects the dust 5120, and sucks it out from the suction port on the bottom. It can suck up dirt.

[0204] In addition, the cleaning robot 5100 analyzes the image captured by the camera 5102 and detects the wall, furniture, or It can detect obstacles such as steps. Image analysis can also detect obstacles such as wiring. If an object that may get tangled in the brush 5103 is detected, the rotation of the brush 5103 can be stopped. can.

[0205] The display 5101 can display the remaining battery level and the amount of dust sucked. The route traveled by the cleaning robot 5100 can be displayed on the display 5101. In addition, the display 5101 is a touch panel, and the operation button 5104 is It may be provided in the ray 5101.

[0206] The cleaning robot 5100 can communicate with a portable electronic device 5140 such as a smartphone. The images captured by the camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the Cleaning Robot 5100 can check the status of the room even when he is away from home. In addition, the display on the display 5101 can be displayed on a mobile electronic device such as a smartphone. You can also check it at 5140.

[0207] The light-emitting device according to one embodiment of the present invention can be used for the display 5101 .

[0208] The robot 2100 shown in FIG. 8(B) includes a computing device 2110, an illuminance sensor 2101, a microphone 2102, upper camera 2103, speaker 2104, display 2105, It is equipped with an internal camera 2106, an obstacle sensor 2107, and a movement mechanism 2108.

[0209] The microphone 2102 has a function of detecting the user's voice and environmental sounds. The speaker 2104 has a function of emitting sound. The device 2102 and the speaker 2104 can be used to communicate with the user. It is possible.

[0210] The display 2105 has the function of displaying various information. Any information desired by the user can be displayed on the display 2105. The display 2105 may be equipped with a touch panel. It may be an information terminal that can be charged by placing it in a fixed position on the robot 2100. and enables data transfer.

[0211] The upper camera 2103 and the lower camera 2106 are used to capture images of the surroundings of the robot 2100. The obstacle sensor 2107 detects the obstacles in the robot 210 by using the moving mechanism 2108. When moving forward, the robot can sense whether there are any obstacles in its path. 00 uses an upper camera 2103, a lower camera 2106, and an obstacle sensor 2107. The light-emitting device according to one embodiment of the present invention can recognize the surrounding environment and move safely. It can be used for the display 2105.

[0212] FIG. 8(C) is a diagram showing an example of a goggle-type display. For example, a housing 5000, a display unit 5001, a speaker 5003, an LED lamp 5004, Operation keys 5005 (including a power switch or an operation switch), a connection terminal 5006, a sensor Sa 5007 (force, displacement, position, velocity, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature Degree, chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient , vibration, odor, or infrared measurement functions), microphone 5008, The display device 5002 includes two display units 5002, a support unit 5012, earphones 5013, and the like.

[0213] The light-emitting device of one embodiment of the present invention can be used for the display portion 5001 and the second display portion 5002. can.

[0214] FIG. 9 shows the light-emitting element according to the first and second embodiments, which is an electric star that is a lighting device. The desk lamp shown in FIG. 9 has a housing 2001 and a light source 2002. The lighting device described in Embodiment 3 may be used as the light source 2002.

[0215] FIG. 10 shows the light emitting element according to the first and second embodiments as an indoor lighting device 300. The light-emitting elements described in the first and second embodiments are used as a light-emitting element having high reliability. Since the light emitting element has high light emission, a highly reliable lighting device can be provided. The light-emitting elements described in Embodiments 1 and 2 can be made large in area, and therefore can be used in large-area lighting devices. In addition, the light-emitting elements described in Embodiments 1 and 2 can be used as Because it is thin, it can be used as a thin lighting device.

[0216] The light emitting elements described in the first and second embodiments are used for the windshield and dashboard of an automobile. The device can also be mounted on a board. This shows an embodiment in which the light-emitting element is used in the windshield or dashboard of an automobile. The light-emitting elements described in Embodiments 1 and 2 are used in the display regions 200 to 5203. It is a display area provided.

[0217] In this embodiment, the display area 5200 and the display area 5201 are provided on the windshield of a car. The display device is equipped with the light-emitting device according to the first and second embodiments. In the light-emitting element described in Embodiment 2, the first electrode and the second electrode are formed using light-transmitting electrodes. By doing so, it is possible to make a so-called see-through display device, where the other side can be seen through. If the display is see-through, it can be installed on the windshield of a car. It can be installed without obstructing the view. When providing the above, organic transistors made of organic semiconductor materials or oxide semiconductors are used. A light-transmitting transistor such as a light-transmitting transistor may be used.

[0218] The display area 5202 is the display device described in Embodiments 1 and 2 provided in the pillar portion. The display device is equipped with a photoelectric element. The display area 5202 is provided with an image pickup means mounted on the vehicle body. By projecting these images, it is possible to complement the view obstructed by the pillars. Similarly, the display area 5203 provided on the dashboard is blocked by the vehicle body. By projecting images from an imaging device installed on the outside of the vehicle, blind spots are compensated for. This can increase safety. By projecting images to complement the invisible parts, This allows you to check for safety more naturally and without any discomfort.

[0219] The display area 5203 also displays navigation information, speedometer and tachometer, mileage, fuel, gear status, etc. By displaying the status of the car, air conditioner settings, etc., various information can be provided. The display items and layout can be changed as needed to suit the user's preferences. This information can also be provided in display areas 5200 to 5202. The display areas 5200 to 5203 can also be used as lighting devices.

[0220] 12(A) and (B) show a foldable mobile information terminal 5150. The foldable mobile information terminal 5150 includes a housing 5151, a display area 5152, and a bending portion 515 12(A) shows the mobile information terminal 5150 in an unfolded state. Fig. 5B) shows the portable information terminal 5150 in a folded state. Although it has a large display area 5152, it is compact and highly portable when folded.

[0221] The display area 5152 can be folded in half by the bend 5153. 3 is composed of an expandable member and multiple support members, and when folding, The member is stretched, and the bent portion 5153 has a radius of curvature of 2 mm or more, preferably 3 mm or more. It can be folded.

[0222] The display area 5152 is a touch panel (input / output) equipped with a touch sensor (input device). The light-emitting device of one embodiment of the present invention can be used in the display region 5152. Cut.

[0223] 13(A) to 13(C) show a foldable mobile information terminal 9310. 13(A) shows the mobile information terminal 9310 in an unfolded state. The mobile information terminal 9310 is shown in a state in which it is changing from one folded state to the other. FIG. 13C shows the portable information terminal 9310 in a folded state. The foldable design offers excellent portability and a seamless, large viewing area when unfolded. This provides excellent visibility of the display.

[0224] The display panel 9311 is supported by three housings 9315 connected by hinges 9313. The display panel 9311 is a touch panel equipped with a touch sensor (input device). The display panel 9311 may be a display panel (input / output device). The two housings 9315 are bent to open the mobile information terminal 9310. The light-emitting device of one embodiment of the present invention can be reversibly transformed from a folded state to a folded state. It can be used for a display panel 9311. A display area 931 in the display panel 9311 2 is a display area located on the side of the portable information terminal 9310 in the folded state. Area 9312 contains information icons and shortcuts to frequently used apps and programs. You can display the information and launch apps smoothly. do. [Example]

[0225] <Element Example 1> In this example, a light-emitting element 1 of one embodiment of the present invention and a comparative light-emitting element 1 will be described. The structural formulae of the organic compounds used in the element 1 and the comparative light-emitting element 1 are shown below.

[0226] [ka]

[0227] (Method for fabricating light-emitting element 1) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The first electrode 101 was formed by a film deposition method. The area was set to 2mm x 2mm.

[0228] Next, as a pretreatment for forming a light emitting element on the substrate, the substrate surface was washed with water and After baking at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0229] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0230] Next, the first electrode 101 is formed so that the surface on which the first electrode 101 is formed faces downward. The substrate was fixed to a substrate holder provided in a vacuum deposition apparatus, and the following was formed on the first electrode 101: N,N-bis(4-biphenyl) represented by the above structural formula (i) was obtained by a vapor deposition method using resistance heating. BB(II)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine ABnf) and NDP-9 (Bunseki Kobo Co., Ltd., material serial number: 1S2017012 4) and 10 nm in a weight ratio of 1:0.1 (= BBABnf: NDP-9). A hole injection layer 111 was formed by co-evaporation.

[0231] Next, BBABnf was deposited on the hole injection layer 111 to form a first hole transport layer 112-1. After that, a second hole transport layer 112-2 was formed by vapor deposition of a compound represented by the above structural formula (ii). 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbamoyl) PCzN2) was evaporated to a thickness of 10 nm to form a hole transport layer 112. Successful.

[0232] Next, 7-[4-(10-phenyl-9-anthryl)-2-(2-methyl-2-phenyl)-1,3-dimethyl-2,4-dimethyl-2,5-dimethyl-2,6 ... )phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), N,N'-(pyrene-1,6-diyl)bis[(6,N- Diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6B nfAPrn-03) in a weight ratio of 1:0.03 (=cgDBCzPA:1,6BnfA The light-emitting layer 113 was formed to a thickness of 25 nm by co-evaporation so that the film was Prn-03).

[0233] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 15 nm, and then 2,9-bis(naphthalen-2-yl)-4,7-diphenyl represented by the above structural formula (v) NBPhen was evaporated to a thickness of 10 nm. The electron transport layer 114 was formed by deposition.

[0234] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. The electron injection layer 115 is formed by depositing aluminum to a thickness of 200 nm. The second electrode 102 was formed by vapor deposition, and the light-emitting element 1 of this example was fabricated.

[0235] (Method for producing comparative light-emitting element 1) The comparative light-emitting element 1 has the same structure as the light-emitting element 1 except for the PCzN 2 is 3-[4-(9-phenanthryl)-phenyl]- The same as Light-emitting element 1 except that the organic compound was changed to 9-phenyl-9H-carbazole (abbreviation: PCPPn). It was made for you.

[0236] The device structures of the light-emitting element 1 and the comparative light-emitting element 1 are summarized in the table below.

[0237] [Table 1]

[0238] The light-emitting element 1 and the comparative light-emitting element 1 were placed in a glove box with a nitrogen atmosphere. The process of sealing the element with a glass substrate to prevent it from being exposed to the atmosphere (sealing material is applied around the element). After the initial stage of these light-emitting devices, The characteristics and reliability were measured at room temperature.

[0239] FIG. 14 shows the luminance-current density characteristics of the light-emitting element 1 and the comparative light-emitting element 1, and The luminance-voltage characteristics are shown in Fig. 15, the current-voltage characteristics are shown in Fig. 16, and the external quantum efficiency-luminance characteristics are shown in Fig. 17. The luminance characteristics are shown in Fig. 18 and the emission spectrum is shown in Fig. 19. m 2 The main characteristics of the area are shown in Table 2.

[0240] [Table 2]

[0241] 14 to 19 and Table 2, the light-emitting element 1 of one embodiment of the present invention has a low driving voltage. It was found that the blue light-emitting element had good characteristics such as luminous efficiency equivalent to that of comparative light-emitting element 1. .

[0242] In addition, the current density is 50mA / cm 2Figure 1 shows a graph showing the change in brightness over time. 20. As shown in FIG. 20, the light-emitting element 1, which is a light-emitting element of one embodiment of the present invention, It was found that the decrease in luminance due to accumulation of charge was small and that the light-emitting element had a long life.

[0243] <Element Example 2> In this example, a light-emitting element 2 of one embodiment of the present invention and a comparative light-emitting element 2 will be described. The structural formulae of the organic compounds used in the element 2 and the comparative light-emitting element 2 are shown below.

[0244] [ka]

[0245] (Method for manufacturing light-emitting element 2) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The first electrode 101 was formed by a film deposition method. The area was set to 2mm x 2mm.

[0246] Next, as a pretreatment for forming a light emitting element on the substrate, the substrate surface was washed with water and After baking at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0247] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0248] Next, the first electrode 101 is formed so that the surface on which the first electrode 101 is formed faces downward. The substrate was fixed to a substrate holder provided in a vacuum deposition apparatus, and the following was formed on the first electrode 101: N,N-bis(4-biphenyl) represented by the above structural formula (i) was obtained by a vapor deposition method using resistance heating. BB(II)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine ABnf) and NDP-9 (Bunseki Kobo Co., Ltd., material serial number: 1S2017012 4) and 10 nm in a weight ratio of 1:0.1 (= BBABnf: NDP-9). A hole injection layer 111 was formed by co-evaporation.

[0249] Next, on the hole injection layer 111, 3,3'-(naphthalene- 1,4-diyl)bis(9-phenyl-9H-carbazole) (abbreviation: PCzN2) The hole transport layer 112 was formed by vapor deposition so as to have a thickness of 0 nm.

[0250] Next, 7-[4-(10-phenyl-9-anthryl)-2-(2-methyl-2-phenyl)-1,3-dimethyl-2,4-dimethyl-2,5-dimethyl-2,6 ... )phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), N,N'-(pyrene-1,6-diyl)bis[(6,N- Diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6B nfAPrn-03) in a weight ratio of 1:0.03 (=cgDBCzPA:1,6BnfA The light-emitting layer 113 was formed to a thickness of 25 nm by co-evaporation so that the film was Prn-03).

[0251] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 15 nm, and then 2,9-bis(naphthalen-2-yl)-4,7-diphenyl represented by the above structural formula (v) NBPhen was evaporated to a thickness of 10 nm. The electron transport layer 114 was formed by deposition.

[0252] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. The electron injection layer 115 is formed by depositing aluminum to a thickness of 200 nm. The second electrode 102 was formed by vapor deposition, and the light-emitting element 2 of this example was fabricated.

[0253] (Method for producing comparative light-emitting element 2) The comparative light-emitting element 2 was fabricated by replacing the PCzN2 used in the hole transport layer 112 of the light-emitting element 2 with the above 3-[4-(9-phenanthryl)-phenyl]-9-phenyl represented by structural formula (vi) The light-emitting element was fabricated in the same manner as light-emitting element 2, except that the fluorine-9H-carbazole (abbreviation: PCPPn) was used instead. Ta.

[0254] The device structures of the light-emitting element 2 and the comparative light-emitting element 2 are summarized in the table below.

[0255] [Table 3]

[0256] The light-emitting element 2 and the comparative light-emitting element 2 were placed in a glove box with a nitrogen atmosphere. The process of sealing the element with a glass substrate to prevent it from being exposed to the atmosphere (sealing material is applied around the element). After the initial stage of these light-emitting devices, The characteristics and reliability were measured at room temperature.

[0257] FIG. 21 shows the luminance-current density characteristics of the light-emitting element 2 and the comparative light-emitting element 2, and FIG. 22 shows the current efficiency-luminance characteristics The luminance-voltage characteristics are shown in Fig. 22, the current-voltage characteristics are shown in Fig. 23, and the external quantum efficiency-luminance characteristics are shown in Fig. 24. The luminance characteristics are shown in Fig. 25 and the emission spectrum is shown in Fig. 26. m 2 The main characteristics of the area are shown in Table 4.

[0258] [Table 4]

[0259] 21 to 25 and Table 4, the light-emitting element 2 of one embodiment of the present invention has a low driving voltage. It was found that the characteristics such as luminous efficiency were equivalent to those of comparative light-emitting element 2, making it a good blue light-emitting element. .

[0260] In addition, the current density is 50mA / cm 2 Figure 1 shows a graph showing the change in brightness over time. 27. As shown in FIG. 27, the light-emitting element 2, which is a light-emitting element of one embodiment of the present invention, It was found that the decrease in luminance due to accumulation of charge was small and that the light-emitting element had a long life.

[0261] <Element Example 3> In this example, a light-emitting element 3 of one embodiment of the present invention and a comparative light-emitting element 3 will be described. The structural formulae of the organic compounds used in the element 3 and the comparative light-emitting element 3 are shown below.

[0262] [ka]

[0263] (Method for manufacturing light-emitting element 3) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The first electrode 101 was formed by a film deposition method. The area was set to 2mm x 2mm.

[0264] Next, as a pretreatment for forming a light emitting element on the substrate, the substrate surface was washed with water and After baking at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0265] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0266] Next, the first electrode 101 is formed so that the surface on which the first electrode 101 is formed faces downward. The substrate was fixed to a substrate holder provided in a vacuum deposition apparatus, and the following was formed on the first electrode 101: N,N-bis(4-biphenyl) represented by the above structural formula (i) was obtained by a vapor deposition method using resistance heating. BB(II)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine ABnf) and NDP-9 (Bunseki Kobo Co., Ltd., material serial number: 1S2017012 4) and 10 nm in a weight ratio of 1:0.1 (= BBABnf: NDP-9). A hole injection layer 111 was formed by co-evaporation.

[0267] Next, BBABnf was deposited on the hole injection layer 111 to form a first hole transport layer 112-1. After that, a second hole transport layer 112-2 was formed by vapor deposition of a compound represented by the above structural formula (ii). 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbamoyl) PCzN2) was evaporated to a thickness of 10 nm to form a hole transport layer 112. Successful.

[0268] Next, 7-[4-(10-phenyl-9-anthryl)-2-(2-methyl-2-phenyl)-1,3-dimethyl-2,4-dimethyl-2,5-dimethyl-2,6 ... )phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), N,N'-(pyrene-1,6-diyl)bis[(6,N- Diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6B nfAPrn-03) in a weight ratio of 1:0.03 (=cgDBCzPA:1,6BnfA The light-emitting layer 113 was formed to a thickness of 25 nm by co-evaporation so that the film was Prn-03).

[0269] Then, on the light-emitting layer 113, 2-{4-[9,10-diphenyl ether}- (Naphthalen-2-yl)-2-anthryl]-1-phenyl-1H-benzimidazo (abbreviation: ZADN) and 8-hydroxyquinolinol represented by the above structural formula (viii). Tritium (abbreviation: Liq) in a weight ratio of 1:1 (= ZADN:Liq) An electron transport layer 114 was formed by vapor deposition to a thickness of 25 nm.

[0270] After forming the electron transport layer 114, Liq was evaporated to a thickness of 1 nm to form the electron injection layer 1 15, and then aluminum is evaporated to a thickness of 200 nm to form the second The electrode 102 was formed to fabricate the light-emitting element 3 of this example.

[0271] (Method for producing comparative light-emitting element 3) The comparative light-emitting element 3 was fabricated by replacing the PCzN2 used in the hole transport layer 112 of the light-emitting element 3 with the above 3-[4-(9-phenanthryl)-phenyl]-9-phenyl represented by structural formula (vi) The light-emitting device was fabricated in the same manner as light-emitting device 3, except that the fluorine-9H-carbazole (abbreviation: PCPPn) was used instead. Ta.

[0272] The device structures of the light-emitting element 3 and the comparative light-emitting element 3 are summarized in the table below.

[0273] [Table 5]

[0274] The light-emitting element 3 and the comparative light-emitting element 3 were placed in a glove box with a nitrogen atmosphere. The process of sealing the element with a glass substrate to prevent it from being exposed to the atmosphere (sealing material is applied around the element). After the initial stage of these light-emitting devices, The characteristics and reliability were measured at room temperature.

[0275] FIG. 28 shows the luminance-current density characteristics of the light-emitting element 3 and the comparative light-emitting element 3, and FIG. 29 shows the current efficiency-luminance characteristics The luminance-voltage characteristics are shown in Fig. 29, the current-voltage characteristics are shown in Fig. 30, and the external quantum efficiency-luminance characteristics are shown in Fig. 31. The luminance characteristics are shown in FIG. 32 and the emission spectrum is shown in FIG. 33. m 2 The main characteristics of the area are shown in Table 6.

[0276] [Table 6]

[0277] 28 to 32 and Table 6, the light-emitting element 3 of one embodiment of the present invention exhibited excellent characteristics such as a driving voltage and a light-emitting efficiency. It was found that the blue light-emitting element had excellent characteristics such as efficiency equivalent to those of the comparative light-emitting element 3.

[0278] In addition, the current density is 50mA / cm 2 Figure 1 shows a graph showing the change in brightness over time. 34. As shown in FIG. 34, the light-emitting element 3, which is a light-emitting element of one embodiment of the present invention, is Even after the lapse of time, the brightness remains at 97% or more of the initial brightness, and the brightness does not decrease with the accumulation of driving time. The drop was very small, and it was found to be a light-emitting element with a good lifespan.

[0279] <Element Example 4> In this example, a light-emitting element 4 of one embodiment of the present invention and a comparative light-emitting element 4 will be described. The structural formulae of the organic compounds used in the element 4 and the comparative light-emitting element 4 are shown below.

[0280] [ka]

[0281] (Method for manufacturing light-emitting element 4) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The first electrode 101 was formed by a film deposition method. The area was set to 2mm x 2mm.

[0282] Next, as a pretreatment for forming a light emitting element on the substrate, the substrate surface was washed with water and After baking at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0283] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0284] Next, the first electrode 101 is formed so that the surface on which the first electrode 101 is formed faces downward. The substrate was fixed to a substrate holder provided in a vacuum deposition apparatus, and the following was formed on the first electrode 101: N,N-bis(4-biphenyl) represented by the above structural formula (i) was obtained by a vapor deposition method using resistance heating. BB(II)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine ABnf) and NDP-9 (Bunseki Kobo Co., Ltd., material serial number: 1S2017012 4) and 10 nm in a weight ratio of 1:0.1 (= BBABnf: NDP-9). A hole injection layer 111 was formed by co-evaporation.

[0285] Next, BBABnf was deposited on the hole injection layer 111 to form a first hole transport layer 112-1. After that, a second hole transport layer 112-2 was formed by vapor deposition of a compound represented by the above structural formula (ii). 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbamoyl) PCzN2) was evaporated to a thickness of 10 nm to form a hole transport layer 112. Successful.

[0286] Next, 7-[4-(10-phenyl-9-anthryl)-2-(2-methyl-2-phenyl)-1,3-dimethyl-2,4-dimethyl-2,5-dimethyl-2,6 ... )phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), N,N'-(pyrene-1,6-diyl)bis[(6,N- Diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6B nfAPrn-03) in a weight ratio of 1:0.03 (=cgDBCzPA:1,6BnfA The light-emitting layer 113 was formed to a thickness of 25 nm by co-evaporation so that the film was Prn-03).

[0287] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 15 nm, and then 2,9-bis(naphthalen-2-yl)-4,7-diphenyl represented by the above structural formula (v) NBPhen was evaporated to a thickness of 10 nm. The electron transport layer 114 was formed by deposition.

[0288] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. The electron injection layer 115 is formed by depositing aluminum to a thickness of 200 nm. The second electrode 102 was formed by vapor deposition, and the light-emitting element 4 of this example was fabricated.

[0289] (Method for producing comparative light-emitting element 4) The comparative light-emitting element 4 has the same structure as the light-emitting element 4 except that the hole injection layer 111 and the first hole transport layer 112 are different from the light-emitting element 4. BBABnf used in -1 was converted into N-(1,1'-biphenyl) represented by the above structural formula (ix). 4-(9-phenyl-9H-carbazole- 3-yl)phenyl]-9H-fluoren-2-amine (abbreviation: PCBBiF) The other steps were the same as those for the light-emitting element 4.

[0290] The device structures of the light-emitting element 4 and the comparative light-emitting element 4 are summarized in the table below.

[0291] [Table 7]

[0292] The light-emitting element 4 and the comparative light-emitting element 4 were placed in a glove box with a nitrogen atmosphere. The process of sealing the element with a glass substrate to prevent it from being exposed to the atmosphere (sealing material is applied around the element). After the initial stage of these light-emitting devices, The characteristics and reliability were measured at room temperature.

[0293] FIG. 35 shows the luminance-current density characteristics of the light-emitting element 4 and the comparative light-emitting element 4, and FIG. 36 shows the current efficiency-luminance characteristics of the light-emitting element 4 and the comparative light-emitting element 4. The luminance-voltage characteristics are shown in Figure 36, the current-voltage characteristics are shown in Figure 37, and the external quantum efficiency-luminance characteristics are shown in Figure 38. The luminance characteristics are shown in Figure 39, and the emission spectrum is shown in Figure 40. m 2 The main characteristics of the area are shown in Table 8.

[0294] [Table 8]

[0295] 35 to 39 and Table 8, the light-emitting element 4 of one embodiment of the present invention is Since it uses a hole transport material with a deeper HOMO level than PCzN2, Holes can be injected without any barriers into hole transport materials with MO levels. It was found that the blue light-emitting element had low luminance and good luminous efficiency.

[0296] In addition, the current density is 50mA / cm 2 Figure 1 shows a graph showing the change in brightness over time. As shown in FIG. 41, the light-emitting element 4, which is a light-emitting element of one embodiment of the present invention, It was found that the decrease in luminance due to accumulation of charge was small and that the light-emitting element had a long life.

[0297] <Element Example 5> In this example, a light-emitting element according to one embodiment of the present invention will be described. The structural formula of the organic compound is shown below.

[0298] [ka]

[0299] (Method for manufacturing the light-emitting element 30) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The first electrode 101 was formed by a film deposition method. The area was 2 mm x 2 mm.

[0300] Next, as a pretreatment for forming a light emitting element on the substrate, the substrate surface was washed with water and After baking at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0301] Then, 10 -4The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0302] Next, the first electrode 101 is formed so that the surface on which the first electrode 101 is formed faces downward. The substrate was fixed to a substrate holder provided in a vacuum deposition apparatus, and the following was formed on the first electrode 101: N,N-bis(4-biphenyl) represented by the above structural formula (i) was obtained by a vapor deposition method using resistance heating. BB(II)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine ABnf) and NDP-9 (Bunseki Kobo Co., Ltd., material serial number: 1S2017012 4) and 10 nm in a weight ratio of 1:0.1 (= BBABnf: NDP-9). A hole injection layer 111 was formed by co-evaporation.

[0303] Next, BBABnf was deposited on the hole injection layer 111 to form a first hole transport layer 112-1. After that, a second hole transport layer 112-2 was formed by vapor deposition of a compound represented by the above structural formula (ii). 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbamoyl) PCzN2) was evaporated to a thickness of 30 nm to form a hole transport layer 112. Successful.

[0304] Next, 7-[4-(10-phenyl-9-anthryl)-2-(2-methyl-2-phenyl)-1,3-dimethyl-2,4-dimethyl-2,5-dimethyl-2,6 ... )phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), N,N'-(pyrene-1,6-diyl)bis[(6,N- Diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6B nfAPrn-03) in a weight ratio of 1:0.03 (=cgDBCzPA:1,6BnfA The light-emitting layer 113 was formed to a thickness of 25 nm by co-evaporation so that the film was Prn-03).

[0305] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 15 nm, and then 2,9-bis(naphthalen-2-yl)-4,7-diphenyl represented by the above structural formula (v) NBPhen was evaporated to a thickness of 10 nm. The electron transport layer 114 was formed by deposition.

[0306] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. The electron injection layer 115 is formed by depositing aluminum to a thickness of 200 nm. The second electrode 102 was formed by vapor deposition, and the light emitting device 30 of this example was fabricated.

[0307] (Method of manufacturing the light-emitting element 50) The light-emitting element 50 has a second hole transport layer 112-2 with a thickness of 50 nm in the light-emitting element 30. Other than that, the light emitting element was fabricated in the same manner as the light emitting element 30 .

[0308] (Method for manufacturing the light-emitting element 70) The light-emitting element 70 has a second hole transport layer 112-2 with a thickness of 70 nm in the light-emitting element 30. Other than that, the light emitting element was fabricated in the same manner as the light emitting element 30 .

[0309] (Method of manufacturing the light-emitting element 80) The light-emitting element 80 has a second hole transport layer 112-2 with a thickness of 80 nm in the light-emitting element 30. Other than that, the light emitting element was fabricated in the same manner as the light emitting element 30 .

[0310] (Method for manufacturing light-emitting element 90) The light-emitting element 90 has a second hole transport layer 112-2 with a thickness of 90 nm in the light-emitting element 30. Other than that, the light emitting element was fabricated in the same manner as the light emitting element 30 .

[0311] (Method of manufacturing the light-emitting element 100) The light emitting element 100 has a second hole transport layer 112-2 having a thickness of 100 nm. The other components were fabricated in the same manner as the light-emitting device 30.

[0312] (Method for manufacturing the light-emitting element 110) The light emitting element 110 has a second hole transport layer 112-2 having a thickness of 110 nm. The other components were fabricated in the same manner as the light-emitting device 30.

[0313] (Method of manufacturing the light-emitting element 130) The thickness of the second hole transport layer 112-2 in the light emitting element 130 is 130 nm. The other components were fabricated in the same manner as the light-emitting device 30.

[0314] The light emitting elements 30 to 130 are placed in a glove box with a nitrogen atmosphere. The process of sealing the element with a glass substrate to prevent it from being exposed to the atmosphere (sealing material is applied around the element). After the LEDs were sealed and subjected to UV treatment and heat treatment at 80°C for 1 hour, the reliability of these LEDs was The measurement was carried out at room temperature.

[0315] Current density of light emitting elements 30 to 130: 50 mA / cm 2 for drive time in A graph showing changes in luminance is shown in Figure 42. As shown in Figure 42, The second hole transport layer 112-2 is a light-emitting element whose lifetime is not affected even if the thickness of the second hole transport layer 112-2 is increased. Therefore, the light-emitting device of the present invention has a second hole transport layer 112- By changing the film thickness of 2, the optical path length inside the light-emitting element can be easily adjusted. It turned out to be an element.

[0316] <Synthesis Example 1> In this synthesis example, the organic compound for the hole-injection layer 111 in the light-emitting element of one embodiment of the present invention was The substance that can be used is 4-[4'-(carbazol-9-yl)biphenyl-4 -yl]-4',4''-diphenyltriphenylamine (abbreviation: YGTBi1BP) The synthesis method is explained in detail below. The structural formula of YGTBi1BP is shown below.

[0317] [ka]

[0318] N,N-di(4-biphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-di 10g (20mmol) oxaborolan-2-ylaniline and 9-(4'-bromobiphenyl) 8.0 g (20 mmol) of (phenyl-4-yl)carbazole, tri(ortho-tolyl) 0.12 g (0.40 mmol) of phosphine and 30 mL of potassium carbonate solution ( Add 5.5 g of ethanol (40 mmol), 120 mL of toluene, and 40 mL of ethanol to a reflux condenser. The mixture was degassed under reduced pressure, and then the system was filled with nitrogen. The mixture was heated at 60°C, and 44 mg of palladium (II) acetate was added to the mixture. (0.20 mmol) was added, and the mixture was stirred at 90° C. for 6 hours. Water was added to the obtained filtrate, and the aqueous layer was separated from the organic layer. The resulting extract and the organic layer were combined and washed with water and saturated saline, and then extracted with magnesium sulfate. The mixture was gravity filtered, and the filtrate was concentrated to give a light brown solid. This solid was subjected to high performance liquid chromatography (HPLC) (mobile phase: chloroform). Further purification gave 10 g of a pale yellow solid, the target product, in a yield of 70%.

[0319] The resulting 10 g of solid was purified by train sublimation. The solid was heated at 365°C under a pressure of 3.4 Pa for 15 minutes while argon was flowing at a rate of 15 mL / min. After sublimation purification, 8.7 g of the target pale yellow solid was obtained with a recovery rate of 87%. The synthesis scheme for this synthesis is shown below.

[0320] [ka]

[0321] The obtained solid 1 The numerical data of H-NMR is as follows: 1 The H NMR chart is shown in Figure 43(A )(B). Note that FIG. 43(B) shows the difference between 7.1 ppm and 8.3 ppm in FIG. 43(A). This chart shows the YGTBi It was found that 1BP was obtained.

[0322] 1 H NMR (chloroform-d, 500 MHz): δ = 8.17 (d, J = 7.5 Hz ,2H),7.88(d,J=8.5Hz,2H),7.78(d,J=,8.0Hz, 2H),7.74(d,J=8.0Hz,2H),7.66(d,J=8.0Hz,2H ),7.62-7.61(m,6H),7.55(d,J=8.5Hz,4H),7.5 0(d,J=8.0Hz,2H),7.46-7.43(m,6H),7.35-7.2 8(m,10H)

[0323] Next, the UV-visible absorption spectra of the toluene solution and solid thin film of YGTBi1BP (hereafter referred to as The solid thin film was mounted on a quartz substrate. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (solution: JASCO Corporation, V-550; Thin film: Hitachi High-Technologies Corporation, U-410 The absorption spectrum of the solution was measured by placing only toluene in a quartz cell. The absorption spectrum of the thin film is calculated by subtracting the transmittance and reflection of the substrate. Absorbance calculated from reflectance (-log 10 It was calculated from [%T / (100-%R)]. %T represents transmittance and %R represents reflectance. The emission spectrum was measured using a fluorometer (( A Hamamatsu Photonics FS920 was used.

[0324] The absorption spectrum and emission spectrum of the obtained toluene solution are shown in Figure 44. The absorption and emission spectra of the solid thin film are shown in Figure 45.

[0325] From the results in Figure 44, the toluene solution of YGTBi1BP has an absorption peak around 351 nm. The emission wavelength peak was observed at 417 nm (excitation wavelength 350 nm). From the results of 45, the solid thin film of YGTBi1BP exhibited the following wavelengths: 356 nm, 296 nm, and 245 nm. An absorption peak is observed around m, and an emission wavelength peak is observed around 437 nm (excitation wavelength 360 nm). A ku was seen.

[0326] The HOMO and LUMO levels of YGTBi1BP were measured by cyclic voltammetry (C V) was calculated based on the measurements. The calculation method is shown below.

[0327] The measurement device used was an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model). The solution used in the CV measurements was dehydrated dimethyl ether. Dimethylformamide (DMF) (Aldrich Corporation, 99.8%, Catalog No. 227 05-6) was used, and the supporting electrolyte was tetra-n-butylammonium perchlorate (nB u4NClO4) (Tokyo Chemical Industry Co., Ltd., Catalog No.: T0836) at 100 mmol / The measurement target is dissolved in a solution to a concentration of 2 mmol / L. It was prepared by dissolving.

[0328] The working electrode was a platinum electrode (PTE platinum electrode, manufactured by BAS Co., Ltd.). The auxiliary electrode was a platinum electrode (manufactured by BAS Co., Ltd., a Pt counter electrode for VC-3 ( 5cm)) and Ag / Ag as the reference electrode. + Electrode (manufactured by BAS Co., Ltd., RE7 The measurements were carried out at room temperature (20 to 25°C). It was.

[0329] The scan rate during CV measurement was standardized to 0.1 V / sec, and the oxidation rate was measured against the reference electrode. The potential Ea [V] and reduction potential Ec [V] were measured. Ea is the midpoint potential of the oxidation-reduction wave and The potential Ec was the midpoint potential of the reduction-oxidation wave. The potential energy for the position is known to be -4.94 eV. Therefore, the HOMO level [eV] = -4.94-Ea, and the LUMO level [eV] = -4.94-E From the formula c, the HOMO level and LUMO level can be calculated.

[0330] As a result, the HOMO level of YGTBi1BP was found to be -5.47 eV. The LUMO level was also found to be -2.34 eV.

[0331] In addition, CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th cycle measurement was When comparing the peak intensity of the oxidation-reduction wave in the first cycle, the Ea measurement showed 83% The Ec measurement showed that YGTBi1BP was oxidized and reduced to 83%. It was confirmed that this organic compound has very good resistance to

[0332] YGTBi1BP was synthesized under the same conditions as in the above synthesis scheme, as shown in the following synthesis scheme. The borane compound was converted to 4'-bromotri(4-biphenylyl)amine, and the halide was converted to 4 It can also be synthesized by converting it into -(9H-carbazol-9-yl)phenylboronic acid. It is possible.

[0333] [ka]

[0334] <Synthesis Example 2> In this synthesis example, the organic compound for the hole-injection layer 111 in the light-emitting element of one embodiment of the present invention was The substance that can be used is 4-[4'-(carbazol-9-yl)biphenyl- 4-yl]-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: Y The synthesis method of YGTBiβNB is explained below. The structural formula of YGTBiβNB is shown below. .

[0335] [ka]

[0336] Step 1: N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaboro] Synthesis of [(1,1'-biphenyl)-2-ylphenyl]-(1,1'-biphenyl)-4-amine 6.4 g (20 mmol) of N-(4-bromophenyl)-4-biphenylamine and 5 0.1g (20mmol) of bis(pinacolato)diboron and 3.9g (40mmol) of potassium acetate and 100 mL of 1,4-dioxane in a 200 mL three-neck flask equipped with a reflux condenser. The mixture was placed in a flask, degassed under reduced pressure, and then the atmosphere in the system was replaced with nitrogen. 0.16 g (0.20 mmol) of [1,1'-bis(diphenylphosphino)ferrocene [N]palladium(II) dichloride dichloromethane adduct was added and refluxed for 7 hours. Water was added to the resulting mixture, and the aqueous layer was separated from the organic layer, after which the aqueous layer was extracted with toluene. The extracted solution and the organic layer were combined, washed with water and saturated brine, and dried over magnesium sulfate. This mixture was gravity filtered, and the resulting filtrate was concentrated to give a brown solid. Recrystallization from ethanol gave 3.2 g of a light brown solid in 43% yield. The synthesis scheme of Peptide 1 is shown below.

[0337] [ka]

[0338] The obtained solid 1 The numerical data of H NMR are shown below. In this study, the target compound, N-[4-(4,4,5,5-tetramethyl-1,3,2-diisopropyl]- [(1,1'-biphenyl)-4-amine]-(2-oxaborolan-2-yl)phenyl I found out that... 1H NMR (chloroform-d, 500 MHz): δ = 7.72 (d, J = 9.0 Hz ,2H),7.57(d,J=8.0Hz,2H),7.53(d,J=8.5Hz,2 H),7.42(t,J=7.5Hz,2H),7.31(t,J=7.5Hz,1H) ,7.20(d,J=8.5Hz,2H),7.06(d,J=8.5Hz,2H),5 .93(s,1H), 1.34(s,12H)

[0339] Step 2: 4-[4'-(carbazol-9-yl)biphenyl-4-yl]-4' -Synthesis of biphenylamine> 3.2 g (8.6 mmol) of N-[4-(4,4,5,5-tetramethyl-2- ... 1,1'-biphenyl]-(1,3,2-dioxaborolan-2-yl)phenyl)- 3.4 g (8.6 mmol) of 9-(4'-bromo-4-biphenyl)-4-amine (ortho-tolyl)carbazole and 52 mg (0.17 mmol) of tri(ortho-tolyl)phos Fin, 10 mL of potassium carbonate aqueous solution (2.0 mol / L), and 60 mL of toluene and 25 mL of ethanol were placed in a 200 mL three-neck flask equipped with a reflux condenser. The mixture was degassed under reduced pressure, and then the system was replaced with nitrogen. After refluxing, the precipitated solid The solid was collected by suction filtration and washed with toluene, ethanol, and water. The synthesis scheme for Step 2 is shown below.

[0340] [ka]

[0341] The obtained solid 1 The numerical data of H NMR is as follows: 1 The H NMR chart is shown in Figure 46(A )(B). Note that FIG. 46(B) shows the difference between 5.8 ppm and 8.3 ppm in FIG. 46(A). This chart shows the enlarged range of pm. The target compound 4-[4'-(carbazol-9-yl)biphenyl-4-yl]-4' -biphenylamine was obtained. 1 H NMR (chloroform-d, 500 MHz): δ = 8.17 (d, J = 7.5 Hz ,2H),7.87(d,J=8.5Hz,2H),7.75(dd,J=9.5,8. 0Hz,4H),7.66(d,J=8.0Hz,2H),7.63(d,J=8.5H z,2H),7.59(d,J=7.0Hz,2H),7.56(d,J=8.0Hz, 4H),7.50(d,J=8.5Hz,2H),7.45-7.42(m,4H),7 .33-7.29(m,3H),7.24-7.21(m,4H),5.91(s,1H )

[0342] Step 3: 4-[4'-(carbazol-9-yl)biphenyl-4-yl]-4' -(2-Naphthyl)-4''-phenyltriphenylamine (abbreviation: YGTBiβNB) Synthesis of> 0.85 g (1.5 mmol) of 4-[4'-(carbazole-9 -yl)biphenyl-4-yl]-4'-biphenylamine and 0.43 g (1.5 mm ol) 2-(4-bromophenyl)naphthalene and 11 mg (30 μmol) di-t ert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (trade name) :cBRIDP (registered trademark)) and 0.29 g (3.0 mmol) of sodium ter t-butoxide and 100 mL of toluene were placed in a 200 mL three-neck flask equipped with a reflux condenser. The mixture was degassed under reduced pressure and then the system was purged with nitrogen. g (15 μmol) of bis(dibenzylideneacetone)palladium(0) was added to the mixture. The mixture was refluxed for 8 hours. Water was added to the resulting mixture, and the aqueous layer was separated from the organic layer. The extract and the organic layer were combined and washed with water and saturated saline. The mixture was filtered by gravity, and the filtrate was concentrated to give 0.83 g The synthesis scheme for Step 3 is shown below.

[0343] [ka]

[0344] The resulting solid (0.83 g) was purified by train sublimation. The solid was heated at 345°C under a pressure of 3.8 Pa for 15 minutes while argon was flowing at a rate of 15 mL / min. After sublimation purification, 0.49 g of the target pale yellow solid was obtained with a recovery rate of 59%. Ta.

[0345] The obtained solid 1 The numerical data of H NMR is as follows: 1 The H NMR chart is shown in Figure 47(A )(B). Note that FIG. 47(B) shows the difference between 7.2 ppm and 8.3 ppm in FIG. 47(A). This chart shows the range of pm in an enlarged scale. It was found that the product YGTBiβNB was obtained. 1H NMR (chloroform-d, 500 MHz): δ = 8.17 (d, J = 8.0 Hz ,2H),8.05(d,J=1.0Hz,1H),7.93-7.86(m,5H), 7.79-7.75(m,5H),7.67(t,J=8.0Hz,4H),7.63- 7.61(m,4H),7.56(d,J=8.5Hz,2H),7.52-7.42( m,8H),7.35-7.28(m,9H).

[0346] Next, the absorption and emission spectra of the toluene solution and solid thin film of YGTBiβNB were measured. The measurement method, equipment, and conditions were the same as those in Synthesis Example 1, so they were repeated. The description is omitted.

[0347] The absorption spectrum and emission spectrum of the obtained toluene solution are shown in Figure 48. The absorption and emission spectra of the solid thin film are shown in Figure 49.

[0348] From the results in Figure 48, the toluene solution of YGTBiβNB has an absorption peak around 359 nm. The emission wavelength peak was observed at 419 nm (excitation wavelength 350 nm). From the results of 49, the solid thin film of YGTBiβNB exhibited the following wavelengths: 365nm, 295nm, and 245nm. An absorption peak is observed around m, and an emission wavelength peak is observed around 437 nm (excitation wavelength 360 nm). A ku was seen.

[0349] The HOMO and LUMO levels of YGTBiβNB were measured by cyclic voltammetry (CV) The calculation was based on the measurements and was carried out in the same manner as in Synthesis Example 1.

[0350] As a result, the HOMO level of YGTBiβNB was found to be -5.47 eV. The LUMO level was also found to be -2.35 eV.

[0351] In addition, CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th cycle measurement was When comparing the peak intensity of the oxidation-reduction wave in the first cycle, the Ea measurement showed 85% In the Ec measurement, 95% of the peak intensity was maintained, indicating that YGTBiβNB is an acid. It was confirmed that the resistance to oxidation and reduction was very good.

[0352] <Synthesis Example 3> In this synthesis example, the organic compound for the hole-injection layer 111 in the light-emitting element of one embodiment of the present invention was The substance that can be used is 4,4'-diphenyl-4''-(9-phenyl-9H Regarding the synthesis of (-fluoren-9-yl)triphenylamine (abbreviation: BBAFLP) The structure of BBAFLP is shown below.

[0353] [ka]

[0354] In a 100 mL three-neck flask, add 1.62 g (5.03 mmol) of bis(4-biphenyl) 2.00 g (5.03 mmol) of 9-(4-bromophenyl)-9- Phenylfluorene and 0.97 g (10.1 mmol) of sodium tert-butanoate oxide and 29 mg (0.050 mmol) of bis(dibenzylideneacetone)palladium (0) and 31 mg (0.10 mmol) of tris(o-tolyl)phosphine and 25 mL of Toluene was added. The mixture was degassed by stirring under reduced pressure, and the flask was filled with nitrogen. The mixture was stirred at 110°C for 5.5 hours under a nitrogen atmosphere. After cooling to room temperature, 25 ml of toluene was added and the mixture was reheated to dissolve the precipitated solid. The resulting filtrate was concentrated and purified with Celite / alumina / Florisil / Celite. After that, recrystallization was carried out with ethyl acetate to obtain 2.61 g of the desired white solid in 81% yield. The synthesis scheme of the above synthesis method is shown below.

[0355] [ka]

[0356] The resulting white solid (2.53 g) was purified by train sublimation. The product was heated at 275°C under the conditions of a pressure of 2.4 Pa and an argon flow rate of 10 mL / min. After purification by sublimation, 1.29 g of white solid BBAFLP was obtained with a recovery rate of 51%. .

[0357] Nuclear magnetic resonance spectroscopy ( 1 The results of the analysis by 1 H NMR are shown below. Ta, 1 The H NMR charts are shown in Figures 50(A) and 50(B). This is a chart showing an enlarged range of 6.9 ppm to 7.9 ppm in (A). From the results, it was found that BBAFLP was obtained in this synthesis example.

[0358] 1 H NMR(CDCl3,500MHz):δ=7.00(d,J=8.6Hz,2H ),δ=7.11(d,J=9.2Hz,2H),δ=7.16(d,J=8.6Hz, 4H),δ=7.20-7.24(m,5H),δ=7.29(q,J=13.2Hz, 7.5Hz,4H),δ=7.37(ddd,J=7.5Hz,1.1Hz,2H),δ =7.41-7.49(m,10H),δ=7.56(d,J=8.1Hz,4H),δ =7.77(d,J=7.5Hz,2H).

[0359] <Synthesis Example 4> In this synthesis example, the organic compound for the hole-injection layer 111 in the light-emitting element of one embodiment of the present invention was The substance that can be used is 4-[4-(9-phenyl-9H-fluorene-9-yl] phenyl]-4',4''-diphenyltriphenylamine (abbreviation: BBAFLBi The synthesis method of BBAFLBi is shown below.

[0360] [ka]

[0361] Step 1: 4-(9-phenyl-9H-fluoren-9-yl)phenylboronic acid Synthesis> In a 500 mL three-neck flask, 15.89 g (40 mmol) of 9-(4-bromo-2-methyl-2-propanol) After adding (phenyl)-9-phenyl-9H-fluorene, degas the mixture by reducing the pressure. The inside of the vessel was replaced with nitrogen. 200 ml of dehydrated tetrahydrofuran (abbreviation: THF) was added to the vessel. The mixture was cooled to about -78°C with stirring, and then 1.59 mol / Add 30 mL (48 mmol) of n-butyllithium hexane solution dropwise and keep the temperature at -40°C. After the temperature was raised, the mixture was stirred for 1 hour. After that, 50 ml of dehydrated THF was added, and the temperature was again adjusted to about -78 After cooling to ° C., 6.4 ml (57 mmol) of trimethyl borate was added dropwise. The mixture was allowed to warm to room temperature and then stirred for 16 hours. After adding 30 ml of hydrochloric acid and stirring, the aqueous layer and organic layer were separated, and the resulting organic layer was diluted with saturated sodium bicarbonate water. The mixture was washed once with 100 ml of saturated saline solution and once with 100 ml of magnesium sulfate. After drying over sodium and concentrating, the mixture was recrystallized from toluene to give 10.1 g of a white solid. The yield was 70%. The synthesis scheme for Step 1 is shown below.

[0362] [ka]

[0363] <Step 2: Synthesis of BBAFLBi> In a 200 mL three-neck flask, 2.53 g (7 mmol) of 4-(9-phenyl-9 H-fluoren-9-yl)phenylboronic acid and 3.34 g (7 mmol) of 4-bromo mo-4',4''-diphenyltriphenylamine and 2.90 g (7 mmol) of carbonate Potassium, 70 mL of toluene, 12.5 mL of ethanol, and 10.5 mL of water were added. This mixture was degassed by stirring under reduced pressure, and the atmosphere in the flask was replaced with nitrogen. The mixture contained 15.7 mg (0.07 mmol) of palladium acetate and 42.2 mg (0.07 mmol) of palladium acetate. mol) tris(o-tolyl)phosphine was added, and the mixture was stirred at 85°C for 6 hours under a nitrogen stream. After the mixture was allowed to cool to room temperature, the precipitated solid was filtered off, and the resulting solution (filtrate) After washing twice with 100 ml of water and once with 50 ml of saturated saline, The water was removed, and this was combined with the solid that had been filtered out after the reaction, and 300 ml of toluene was added. After adding the cellulose, heat it to dissolve the solid, then add the celite / alumina / florisil / celite The obtained filtrate was concentrated, and then recrystallized by adding ethanol. The synthesis scheme for Step 2 is shown below.

[0364] [ka]

[0365] The resulting white solid (4.39 g) was purified by train sublimation. The product was heated at 320°C under the conditions of a pressure of 3.5 Pa and an argon flow rate of 15 mL / min. After purification by sublimation, 2.73 g of white solid BBAFLBi was obtained with a recovery rate of 62%. Ta.

[0366] Nuclear magnetic resonance spectroscopy ( 1 The results of the analysis by 1 H NMR are shown below. Ta, 1 The H NMR charts are shown in Figures 51(A) and 51(B). This is a chart showing an enlarged range of 6.9 ppm to 7.9 ppm in (A). From the results, it was found that BBAFLBi was obtained in this synthesis example.

[0367] 1 H NMR(CDCl3,500MHz):δ=7.17-7.28(m,13H), δ=7.31(dd,J=12.6Hz,7.4Hz,4H),δ=7.37(dd,J =7.5Hz,1.1Hz,4H),δ=7.40-7.47(m,10H),δ=7. 51(d,J=8.6Hz,4H)δ=7.58(d,J=8.1Hz,4H)δ=7. 78(d,J=7.4Hz,2H).

[0368] <Synthesis Example 5> In this synthesis example, the organic compound for the hole-injection layer 111 in the light-emitting element of one embodiment of the present invention was The substance that can be used is 4,4'-diphenyl-3''-(9-phenylfluoromethyl). This article explains how to synthesize mBBAFLP (mBBAFLP) The structure of mBBAFLP is shown below.

[0369] [ka]

[0370] In a 300 mL three-neck flask, add 2.67 g (8.31 mmol) of bis(4-biphenyl) 3.00 g (7.55 mmol) of 9-(3-bromophenyl)-9 -phenylfluorene and 1.88 g (16.8 mmol) of sodium tert-butyl ether The mixture was degassed by stirring under reduced pressure. The atmosphere in the flask was replaced with nitrogen. fin (10 wt% hexane solution) and 45 mg (0.078 mmol) of bis(dibenzoyl) (Iryleneacetone)palladium(0) was added, and the mixture was stirred at 110°C for 3 hours under a nitrogen stream. After stirring, the mixture was cooled to room temperature and the solid matter was filtered off. The filtrate was passed through Celite, Floris The filtrate was concentrated, and ethanol was added to the concentrate to cause recrystallization. The resulting white crystals were purified by silica gel column chromatography (developing solvent: toluene). The desired white solid was obtained in 4.58 g with a yield of 95%. The synthesis scheme of the above synthesis method is shown below. Shown below.

[0371] [ka]

[0372] The resulting white solid (2.00 g) was purified by train sublimation. The product was heated at 270°C under conditions of a pressure of 2.9 Pa and an argon flow rate of 5 mL / min. After sublimation purification, 1.87 g of white solid mBBAFLP was obtained with a recovery rate of 94%. .

[0373] Nuclear magnetic resonance spectroscopy ( 1 The results of the analysis by 1 H NMR are shown below. Ta, 1 The H NMR charts are shown in Figures 52(A) and 52(B). This is an enlarged chart showing the range of 6.5 ppm to 8.0 ppm in (A). The results showed that mBBAFLP was obtained by this synthesis example.

[0374] 1 H NMR(CDCl3,500MHz):δ=6.75(d,J=8.0Hz,1H ),δ=6.99(d,J=7.0Hz,1H),δ=7.07(q,J=7.7Hz, 1H),δ=7.13-7.20(m,11H),δ=7.23(d,J=7.5Hz, 1H)δ=7.34(t,J=8.0Hz,6H),δ=7.42(s,1H),δ=7 .45(t,J=8.3Hz,7H),δ=7.57(d,J=7.5,4H),δ=7 .74(d,J=7.5,2H).

[0375] <Synthesis Example 6> In this synthesis example, the organic compound for the hole-injection layer 111 in the light-emitting element of one embodiment of the present invention was The substance that can be used is 4-[3-(9-phenyl-9H-fluorene-9-yl] phenyl]-4',4''-diphenyltriphenylamine (abbreviation: mpBBAFL The synthesis method of mpBBAFLBi is explained below. The structural formula of mpBBAFLBi is shown below.

[0376] [ka]

[0377] In a 200 mL three-neck flask, add 9-(3-bromophenyl)-9-phenyl-9H-fluoro 2.0 g (5.0 mmol), 2-{4-[di(4-biphenylyl)amino]phenyl 2.6 g (5. 0mmol), tri(ortho-tolyl)phosphine 30mg (0.10mmol), carbonate 2.8 g (20 mmol) of potassium was added, and the atmosphere in the flask was replaced with nitrogen. Add 15 mL of toluene, 10 mL of ethanol, and 10 mL of water, and degas by stirring under reduced pressure. To this mixture was added 11 mg (0.050 mmol) of palladium (II) acetate, and the mixture was heated under nitrogen. The mixture was stirred under airflow at 80°C for 2 hours.

[0378] After stirring, the mixture was filtered under suction to recover the solid, which was dissolved in hot toluene and The filtrate was concentrated and the resulting solid was filtered through Celite, alumina, and Florisil. The product was recrystallized from toluene to give 2.7 g of the desired white solid in 74% yield. The synthesis scheme of the above synthesis method is shown below.

[0379] [ka]

[0380] The resulting white solid (2.6 g) was purified by train sublimation. The white solid was heated to 280°C under the conditions of a pressure of 3.5 Pa and an argon flow rate of 5.0 mL / min. After purification by sublimation, 2.3 g of a pale yellow solid was obtained with a recovery rate of 88%.

[0381] Nuclear magnetic resonance spectroscopy ( 1 The results of analysis by 1 H NMR are shown below. Also, 1 The H NMR charts are shown in Figures 53(A) and 53(B). 3(A) is an enlarged chart showing the range of 7.0 ppm to 8.0 ppm. From this result, it was found that mpBBAFLBi was obtained in this synthesis example.

[0382] 1 H NMR(DMSO,300MHz):δ=7.06-7.49(m, 29H),7 .59-7.64(m,8H),7.90(d,J=7.8Hz,2H).

[0383] Next, the absorption and emission spectra of mpBBAFLBi in toluene solution and solid thin film were measured. The measurement method, equipment, and conditions were the same as those in Synthesis Example 1, so they were not repeated. The description of "shi" is omitted.

[0384] The absorption spectrum and emission spectrum of the obtained toluene solution are shown in Figure 54. The absorption and emission spectra of the solid thin film are shown in Figure 55.

[0385] From the results in Figure 54, the toluene solution of mpBBAFLBi has an absorption peak at around 348 nm. A peak in the emission wavelength was observed at 394 nm (excitation wavelength 353 nm). From the results in Figure 55, in the solid thin film of mpBBAFLBi, the An absorption peak is observed, and an emission wavelength peak is observed around 414 nm (excitation wavelength 355 nm). It was.

[0386] The HOMO and LUMO levels of mpBBAFLBi were measured by cyclic voltammetry (CV The calculation method was the same as in Synthesis Example 1.

[0387] As a result, the HOMO level of mpBBAFLBi was found to be -5.49 eV. The LUMO level was also found to be -2.12 eV.

[0388] In addition, CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th cycle measurement was When comparing the peak intensity of the oxidation-reduction wave in the first cycle, the Ea measurement showed 85% The Ec measurement showed that 93% was maintained, indicating that mpBBAFLBi was oxidized and reduced. It was confirmed that it is an organic compound with very good resistance to

[0389] <Synthesis Example 7> In this synthesis example, the organic compound for the hole-injection layer 111 in the light-emitting element of one embodiment of the present invention was The substance that can be used is 4-(4-biphenylyl)-4'-(2-naphthyl)- This article explains the synthesis method of 4''-phenyltriphenylamine (abbreviation: TPBiAβNB). The structural formula of TPBiAβNB is shown below.

[0390] [ka]

[0391] <Step 1: N-(1,1'-biphenyl)-4-yl-(1,1':4',1''- Synthesis of 4-terphenyl-4-amine 3.2 g (10 mmol) of N-(4-bromophenyl)-4-biphenylamine and 2 0.5g (10mmol) of 4-biphenylboronic acid and 61mg (0.20mmol) of Tri(ortho-tolyl)phosphine and 10 mL of aqueous potassium carbonate (2.0 mol / L), 70 mL of toluene, and 30 mL of ethanol were added to a 200 mL flask equipped with a reflux condenser. The mixture was placed in a three-neck flask, degassed under reduced pressure, and then the atmosphere in the system was replaced with nitrogen. To the mixture, 22 mg (0.10 mol) of palladium (II) acetate was added and the mixture was refluxed for 3 hours. After stirring, the precipitated solid was collected by suction filtration, and the obtained solid was dissolved in toluene, ethanol, and water. After washing, 2.69 g of a brown solid was obtained in 86% yield. The team is shown below.

[0392] [ka]

[0393] Step 2: 4-(4-biphenylyl)-4'-(2-naphthyl)-4''-phenyl Synthesis of triphenylamine (abbreviation: TPBiAβNB) 1.5 g (2.7 mmol) of N-(1,1'-biphenyl)-4 obtained in step 1 -yl-(1,1':4',1''-terphenyl)-4-4-amine, and 0.75 g ( 2.7 mmol) of 2-(4-bromophenyl)naphthalene and 18 mg (0.053 m mol) di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl) phosphatase Sulfonyl ether, 0.51 g (5.3 mmol) sodium tert-butoxide, and toluene. 100 mL of benzene was placed in a 200 mL three-neck flask equipped with a reflux condenser, and the mixture was degassed under reduced pressure. After that, the system was purged with nitrogen. Bis(dibenzylideneacetone)palladium(0) was added and the mixture was refluxed for 8 hours. Water was added to the resulting mixture, the aqueous layer was separated from the organic layer, and the aqueous layer was extracted with toluene. The resulting extract and organic layer were combined, washed with water and saturated brine, and dried over magnesium sulfate. This mixture was gravity filtered and the resulting filtrate was concentrated to give 1.1 g of a brown solid. The synthesis scheme of Peptide 2 is shown below.

[0394] [ka]

[0395] The resulting solid (1.1 g) was purified by train sublimation. The solid was heated at 300°C for 15 hours under a pressure of 3.7 Pa while argon was flowing at 15 mL / min. After sublimation purification, 620 mg of the target pale yellow solid was obtained with a recovery rate of 56%. .

[0396] The numerical data of the solid obtained is as follows: 1 The H NMR charts are shown in Figures 56(A) and 56(B). Note that Figure 56(B) expands the range of 7.2 ppm to 8.3 ppm in Figure 56(A). This chart shows the results of the synthesis of the target compound, TPB, in this synthesis example. It was found that iAβNB was obtained. 1 H NMR (chloroform-d, 500 MHz): δ = 8.04 (d, J = 1.5 Hz ,1H),7.91(d,J=8.5Hz,1H),7.89(d,J=9.5Hz,1 H),7.86(d,J=8.0Hz,1H),7.77(dd,J=4.0Hz,1. 5Hz,1H),7.70-7.65(m,8H),7.62-7.58(m,4H), 7.55(d,J=9.0Hz,2H),7.52-7.43(m,6H),7.38- 7.27(m,8H)

[0397] Next, the absorption and emission spectra of TPBiAβNB in ​​toluene solution and solid thin film were measured. The measurement method, equipment, and conditions were the same as those in Synthesis Example 1, so they were repeated. The description is omitted.

[0398] The absorption spectrum and emission spectrum of the resulting toluene solution are shown in Figure 57. The absorption and emission spectra of the solid thin film are shown in Figure 58.

[0399] From the results in Figure 57, the toluene solution of TPBiAβNB has an absorption peak around 357 nm. The emission wavelength peak was observed at 409 nm (excitation wavelength 357 nm). From the results of 58, the solid thin film of TPBiAβNB exhibited the following peaks: 364 nm, 280 nm, and 253 nm. An absorption peak is observed around m, and an emission wavelength peak is observed around 430 nm (excitation wavelength 370 nm). A ku was seen.

[0400] The HOMO and LUMO levels of TPBiAβNB were measured by cyclic voltammetry (CV). The calculation was based on the measurements and was carried out in the same manner as in Synthesis Example 1.

[0401] As a result, the HOMO level of TPBiAβNB was −5.47 eV and the LUMO level was −2.2 It was found to be 9 eV.

[0402] In addition, CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th cycle measurement was When comparing the peak intensity of the oxidation-reduction wave in the first cycle, the Ea measurement showed 89% In the Ec measurement, 98% of the peak intensity was maintained, indicating that TPBiAβNB is an acid. It was confirmed that the resistance to oxidation and reduction was very good.

[0403] <Synthesis Example 8> In this synthesis example, the organic compound for the hole-injection layer 111 in the light-emitting element of one embodiment of the present invention was The substance that can be used is 4-(4-biphenylyl)-4'-{4-(2-naphthyl) {4'-phenyl)phenyl}-4''-phenyltriphenylamine (abbreviation: TPBiAβNBi) The synthesis method is explained below. The structural formula of TPBiAβNBi is shown below.

[0404] [ka]

[0405] Step 1: N-(1,1'-biphenyl)-4-yl-(1,1':4',1'-titanium dioxide) Synthesis of (phenyl)-4-(4-aminomethyl)amine 2.4 g (7.4 mmol) of N-(4-bromophenyl)-4-biphenylamine, 1.5 g (7.4 mmol) of 4-biphenylboronic acid and 47 mg (0.15 mmol) ) tri(ortho-tolyl)phosphine and 7 mL of aqueous potassium carbonate (2.0 mol / L), 60 mL of toluene, and 20 mL of ethanol were added to a 200 mL The mixture was placed in a three-neck flask, degassed under reduced pressure, and then the atmosphere in the system was replaced with nitrogen. To the mixture was added 16 mg (74 μmol) of palladium(II) acetate, and the mixture was refluxed for 3 hours. The precipitated solid was then collected by suction filtration, and the resulting solid was dissolved in toluene, ethanol, and water. After washing, 2.94 g of the desired gray solid was obtained in a yield of over 99%. The synthesis scheme is shown below.

[0406] [ka]

[0407] <Step 2: Synthesis of 2-(4-chloro-biphenyl-4-yl)naphthalene> 2.4 g (10 mmol) of 1-chloro-4-iodobenzene and 2.5 g (10 mmol) l) 4-(2-naphthyl)phenylboronic acid and 61 mg (0.20 mmol) of trimethylsilyl (ortho-tolyl)phosphine and 20 mL of aqueous potassium carbonate (2.0 mol / L) 70 mL of toluene and 30 mL of ethanol were placed in a 200 mL three-neck flask equipped with a reflux condenser. The solvent was degassed under reduced pressure and the inside of the container was replaced with nitrogen. Palladium (22 mg, 0.10 mmol) was added and the mixture was stirred at 50°C for 3 hours to complete the reaction. After stirring, the precipitated solid was collected by suction filtration and washed with toluene, water, and ethanol. After purification, 2.7 g of a brown solid was obtained in 86% yield. The synthesis scheme for Step 2 is as follows: Shown below.

[0408] [ka]

[0409] The numerical data of the obtained brown solid is shown below. It was found that (4-chloro-biphenyl-4-yl)naphthalene was obtained. 1 H NMR (dichloromethane-d2, 500 MHz): δ = 8.13 (s, 1H), 7 .96(d,J=9.5Hz,1H),7.94(d,J=9.5Hz,1H),7.8 9(d,J=7.0Hz,1H),7.85-7.81(m,3H),7.72(d,J =8.0Hz,2H),7.64(d,J=8.5Hz,2H),7.55-7.49( m, 2H), 7.46(d, J=8.0Hz, 2H)

[0410] Step 3: 4-(4-biphenylyl)-4'-{4-(2-naphthyl)phenyl}- Synthesis of 4''-phenyltriphenylamine (TPBiAβNBi) 2.94 g (7.4 mmol) of N-(1,1'-biphenyl)- obtained in Step 1 Step 2: 4-yl-(1,1':4',1''-terphenyl)-4-4-amine 2.32 g (7.4 mmol) of 2-(4-chloro-biphenyl-4-yl) Naphthalene and 52 mg (0.15 mmol) of di-tert-butyl(1-methyl-2 ,2-diphenylcyclopropyl)phosphine (trade name: cBRIDP (registered trademark)) , 1.4g (15mmol) sodium tert-butoxide and 140mL xylene The mixture was degassed under reduced pressure and then cooled to 100°C. The resulting mixture was purged with nitrogen. Palladium(0) in acetone was added and the mixture was refluxed for 5 hours. The solid was collected by suction filtration and washed with toluene, water, and ethanol to give a gray solid. The synthesis scheme for Step 3 is shown below.

[0411] [ka]

[0412] The resulting solid (3.8 g) was purified by train sublimation. The solid was heated at 335°C under a pressure of 3.8 Pa for 15 hours while argon was flowing at 15 mL / min. After purification by sublimation, 2.8 g of the target pale yellow solid was obtained with a recovery rate of 74%.

[0413] The numerical data of the solid obtained is as follows:1 The H NMR charts are shown in Figures 59(A) and 59(B). Note that Figure 59(B) expands the range of 7.2 ppm to 8.3 ppm in Figure 59(A). This chart shows the results of the synthesis of the target compound, TPB, in this synthesis example. It was found that iAβNBi was obtained. 1 H NMR (chloroform-d, 500 MHz): δ = 8.10 (d, J = 1.5 Hz ,1H),7.94(d,J=9.0Hz,1H),7.92(d,J=7.5Hz,1 H),7.88(d,J=7.5Hz,1H),7.82-7.80(m,3H),7. 73(d,J=8.5Hz,2H),7.68(s,4H),7.66(d,J=7.0 Hz,2H),7.62-7.58(m,6H),7.55(d,J=8.5Hz,2H ),7.52-7.43(m,6H),7.36(t,J=7.0Hz,1H),7.3 3(t,J=7.0Hz,1H),7.29-7.27(m,6H).

[0414] Next, the absorption and emission spectra of TPBiAβNBi in toluene solution and solid thin film were measured. The measurement method, equipment, and conditions were the same as those in Synthesis Example 1, so they were not repeated. The description of "shi" is omitted.

[0415] The absorption and emission spectra of the resulting toluene solution are shown in Figure 60. The absorption and emission spectra of the solid thin film are shown in Figure 61.

[0416] From the results in Figure 60, the toluene solution of TPBiAβNBi has an absorption peak at around 359 nm. A peak in the emission wavelength was observed at 420 nm (excitation wavelength 410 nm). From the results in Figure 61, the solid thin film of TPBiAβNBi exhibited the following wavelengths: 368 nm, 295 nm, and 27 An absorption peak is observed around 2 nm, and an emission peak is observed around 439 nm (excitation wavelength 370 nm). A peak was observed.

[0417] The HOMO and LUMO levels of TPBiAβNBi were measured by cyclic voltammetry (CV The calculation method was the same as in Synthesis Example 1.

[0418] As a result, the HOMO level of TPBiAβNBi is -5.47 eV and the LUMO level is -2. It was found to be 38 eV.

[0419] In addition, CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th cycle measurement was When comparing the peak intensity of the oxidation-reduction wave in the first cycle, the Ea measurement showed 83% , TPBiAβNBi maintained 95% of the peak intensity in the Ec measurement. It was confirmed that the resistance to oxidation and reduction was very good.

[0420] <Synthesis Example 9> In this synthesis example, the organic compound for the hole-injection layer 111 in the light-emitting element of one embodiment of the present invention was The substance that can be used is 4,4'-diphenyl-4''-(7-phenyl) naphthyl. Synthesis of 2-ethyltriphenylamine (BBAPβNB-03) The structural formula of BBAPβNB-03 is shown below.

[0421] [ka]

[0422] <Step 1: Synthesis of 7-bromo-2-phenylnaphthalene> 3.8 g (13 mmol) of 2,7-dibromonaphthalene and 2.3 g (13 mmol) of phenylboronic acid and 81 mg (27 μmol) of tri(ortho-tolyl)phosphine 65 mL of toluene, 30 mL of ethanol, and 15 mL of 2 M potassium carbonate solution The solution (2.0 mmol / L) was placed in a 200 mL three-neck flask and the mixture was degassed under reduced pressure. After that, the system was purged with nitrogen. Then, 30 mg (0.13 mmol) of palladium acetate was added. The resulting reaction mixture was stirred at room temperature for 3 hours. The precipitated solid was removed by suction filtration. Water was added to the obtained filtrate, and the aqueous layer was separated from the organic layer. The aqueous layer was then extracted with toluene. The resulting extract and organic layer were combined, washed with water and saturated saline, and then extracted with magnesium sulfate. The resulting mixture was gravity filtered and then concentrated, and the resulting residue was analyzed by high performance liquid chromatography. The target compound was purified by chromatography (mobile phase: chloroform) in a yield of 2.3 ml. The synthesis scheme for Step 1 is shown below.

[0423] [ka]

[0424] Step 2: 4,4'-diphenyl-4''-(7-phenyl)naphthyl-2-yl Synthesis of phenylamine (abbreviation: BBAPβNB-03) 1.8 g (6.5 mmol) of 7-bromo-2-phenylnaphthalene obtained in Step 1 and 3.5 g (6.5 mmol) of N,N-di(4-biphenyl)-4-(4,4,5 ,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline and 40mg (0.13 mmol) of tri(ortho-tolyl)phosphine and 6.5 mL of potassium carbonate. Aqueous solution of ethanol (2.0 mol / L), 60 mL of toluene, and 35 mL of ethanol were mixed in a reduced The mixture was placed in a 200 mL three-neck flask equipped with a flow tube, and after degassing under reduced pressure, the system was purged with nitrogen. To the resulting mixture, 14 mg (65 μmol) of palladium(II) acetate was added. The mixture was refluxed for 4 hours. After stirring, the precipitated solid was removed by suction filtration. Water was added to the obtained filtrate. After separating the aqueous layer from the organic layer, the aqueous layer was extracted with toluene. The mixture was washed with water and saturated brine, and then dried over magnesium sulfate. The filtrate obtained after filtration was concentrated to give 2.1 g of a brown solid. Shown below.

[0425] [ka]

[0426] The resulting brown solid (1.9 g) was purified by train sublimation. The solid was heated to 280°C under a pressure of 4.1 Pa while flowing argon at 15 mL / min. After sublimation purification, 1.1 g of the target pale yellow solid was obtained with a recovery rate of 51%. Ta.

[0427] The numerical data of the solid obtained is as follows: 1 The H NMR charts are shown in Figures 62(A) and 62(B). Note that Figure 62(B) expands the range of 7.2 ppm to 8.3 ppm in Figure 62(A). This chart shows the overall structure of the target compound, BBA, in this synthesis example. It was found that PβNB-03 was obtained. 1 H NMR (dichloromethane-d2, 500 MHz): δ = 8.13 (d, J = 2.0 Hz,2H),7.95(d,J=8.5Hz,2H),7.80-7.76(m,4H ),7.72(d,J=9.0Hz,2H),7.62(d,J=8.0Hz,4H), 7.57(d,J=8.5Hz,4H),7.50(t,J=8.0Hz,2H),7. 44(t,J=8.0Hz,4H),7.40(t,J=7.5Hz,1H),7.33 (t,J=7.5Hz,2H),7.29(d,J=8.5Hz,2H),7.26(d ,J=8.5Hz,4H)

[0428] Next, the absorption and emission spectra of BBAPβNB-03 in toluene solution and solid thin film were measured. The measurement method, equipment, and conditions were the same as those in Synthesis Example 1, so they were repeated. Omit the reply.

[0429] The absorption and emission spectra of the resulting toluene solution are shown in Figure 63. The absorption and emission spectra of the solid thin film are shown in Figure 64.

[0430] From the results in Figure 63, the toluene solution of BBAPβNB-03 has an absorption peak at around 352 nm. A peak was observed in the emission wavelength at 409 nm (excitation wavelength 352 nm). ,From the results of Figure 64, for the solid thin film of BBAPβNB-03, 359nm, 259nm, An absorption peak is observed around 211 nm, and an emission peak is observed around 430 nm (excitation wavelength 360 nm). A long peak was observed.

[0431] The HOMO and LUMO levels of BBAPβNB-03 were measured by cyclic voltammetry (C V) was measured. The calculation method was the same as in Synthesis Example 1.

[0432] As a result, the HOMO level of BBAPβNB-03 is -5.47 eV and the LUMO level is -2 It was found to be 0.33 eV.

[0433] In addition, CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th cycle measurement was When comparing the peak intensity of the oxidation-reduction wave in the first cycle, the Ea measurement showed 91% In the Ec measurement, 85% of the peak intensity was maintained, indicating that BBAPβNB-03 It was confirmed that the compound has very good resistance to oxidation and reduction.

[0434] <Synthesis Example 10> In this synthesis example, the organic compound for the hole-injection layer 111 in the light-emitting element of one embodiment of the present invention was The substance that can be used is 4'-[4-(3-phenyl-9H-carbazole-9 -yl)phenyl]tris(1,1'-biphenyl-4-yl)amine (abbreviation: YGTB The synthesis method of YGTBi1BP-02 is explained below. The structural formula of YGTBi1BP-02 is as follows: Shown below.

[0435] [ka]

[0436] Step 1: 4'-(4-chlorophenyl)tris(1,1'-biphenyl-4-yl) )Amine synthesis> Add 8.8 g (17 mmol) of 2-{4-[di(4-biphenyl)] (aryl)amino]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaboro Ran, 4.5 g (17 mmol) of 4-bromo-4'-chlorobiphenyl, and 0.15 g (0.50 mmol) of tri(ortho-tolyl)phosphine and 25 mL of potassium carbonate. Add 128 mL of toluene and 32 mL of ethanol. After degassing the mixture under reduced pressure, the atmosphere in the flask was replaced with nitrogen. 0.17 mmol) of palladium(II) acetate was added and the mixture was stirred at 60°C for 9.5 hours. The precipitated solid was then collected by suction filtration, and the resulting solid was dissolved in toluene, ethanol, and water. The washed solid was dissolved in hot toluene, and the resulting solution was washed with alumina, Florisy (Wako Pure Chemical Industries, Ltd., Catalog No.: 066-05265), Celite (Wako Pure Chemical Industries, Ltd. The mixture was filtered through a filter (Koyo Co., Ltd., Catalog No.: 537-02305), and the filtrate was allowed to cool. When this white solid was collected by suction filtration, the target compound was found to be 6. The filtrate was concentrated to give a pale yellow solid, which was recrystallized from toluene to give a white solid. 3.4 g of the compound was obtained. In total, 9.5 g of a white solid was obtained in 95% yield. The team is shown below.

[0437] [ka]

[0438] Step 2: 4'-[4-(3-phenyl-9H-carbazol-9-yl)phenyl ]Tris(1,1'-biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02) Synthesis of> In a 200 mL three-neck flask, add 2.0 g (3.4 mmol) of 4'- (4-chlorophenyl)tris(1,1'-biphenyl-4-yl)amine, 0.83 g (3.4 mmol) of 3-phenyl-9H-carbazole and 36 mg (0.10 mm ol) di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl ) phosphine (abbreviation: cBRIDP) and 0.99 g (10 mmol) of sodium t Add 35 mL of ethyl butoxide and mesitylene, degas the mixture under reduced pressure, and then The atmosphere was replaced with nitrogen. 21 mg (34 μmol) of bis(dibenzylidene acetate) was added to this mixture. (Ion)Palladium(II) was added and the mixture was stirred at 120°C for 8.5 hours. The reaction was confirmed by thin layer chromatography and the raw material remained, so 37 mg (0.10 mmol) of cBRIDP and 20 mg (33 μmol) of bis(di After adding (benzylideneacetone)palladium(II), the mixture was heated and stirred at 150°C for 6 hours. After heating, toluene and water were added to the resulting mixture, and the mixture was stirred. The organic layer of the mixture was then saturated with water. The organic layer was washed with saturated saline, and dried over anhydrous magnesium sulfate. This mixture was subjected to gravity filtration, and the filtrate was concentrated to give a brown solid. The solution was dissolved in ethylene and mixed with alumina, Florisil (Wako Pure Chemical Industries, Ltd., catalog no. No.: 066-05265), Celite (Wako Pure Chemical Industries, Ltd., Catalog No.: 537- The resulting filtrate was concentrated to give a yellowish brown solid. The solid was recrystallized from toluene to obtain 1.9 g of a yellow solid, which was the target substance, in a yield of 69%. The synthesis scheme for Step 2 is shown below.

[0439] [ka]

[0440] The obtained solid 1 The H NMR data is shown in Figure 65, and the numerical data is shown below. 4'-[4-(3-phenyl-9H-carbazol-9-yl)phenyl]tris(1, 1'-biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02) was obtained. I found out.

[0441] 1 H NMR (dichloromethane-d2, 500 MHz): δ = 7.24 (d, J = 7.0 Hz,3H),7.26(d,J=7.0Hz,3H),7.30-7.35(m,4H ),7.41-7.52(m,8H),7.56(dt,J1=8.5Hz,J2=1. 5Hz,5H),7.63(d,J=8.5Hz,4H),7.63(d,J=8.5H z,2H),7.69-7.71(m,3H),7.73-7.76(m,4H),7. 80(d,J=8.5Hz,2H),7.92(dt,J1=8.0Hz,J2=1.5 Hz,2H),8.21(d,J=7.5Hz,1H),8.39(sd,J=1.0H z,1H)

[0442] The resulting solid (1.9 g) was purified by sublimation under a pressure of 1.9 × 10 -3 Pa The solid was heated to 370°C under the conditions. After purification by sublimation, a yellow solid of the target compound was obtained in a yield of 0. 0.74g was obtained with a recovery rate of 40%.

[0443] Next, the absorption and emission spectra of the toluene solution and solid thin film of YGTBi1BP-02 were measured. The measurement method, equipment, and conditions were the same as those in Synthesis Example 1, so the same procedures were repeated. Repeated entries are omitted.

[0444] The absorption and emission spectra of the resulting toluene solution are shown in Figure 66. The absorption and emission spectra of the solid thin film are shown in Figure 67.

[0445] From the results in Figure 66, the toluene solution of YGTBi1BP-02 has an absorption peak around 353 nm. The peak of the emission wavelength was 419 nm (excitation wavelength 353 nm). 67, the solid thin film of YGTBi1BP-02 is 356nm, 290nm, 251nm, An absorption peak is observed around 207 nm, and emission wavelength peaks are observed around 439 nm and 453 nm. This result indicates that YGTBi1BP-02 emits blue light. It has been confirmed that the compound emits light, and can be used as a host for luminescent materials and visible fluorescent materials. I found out that...

[0446] The HOMO and LUMO levels of YGTBi1BP-02 were measured by cyclic voltammetry ( The calculation method was the same as in Synthesis Example 1.

[0447] As a result, the HOMO level of YGTBi1BP-02 is -5.47 eV and the LUMO level is - It was found to be 2.35 eV.

[0448] In addition, CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th cycle measurement was When comparing the peak intensity of the oxidation-reduction wave in the first cycle, the Ea measurement showed 88% , and the Ec measurement maintained 96% of the peak intensity, indicating that YGTBi1BP-0 2 was confirmed to have very good resistance to oxidation and reduction.

[0449] In addition, differential scanning calorimetry (DSC) of YGTBi1BP-02 was performed. DSC (Dyscalometry) was performed using a PerkinElmer Pyris The differential scanning calorimetry was performed at a temperature rise rate of 40°C / min, and After heating from ℃ to 360℃, the temperature was kept at the same temperature for 3 minutes, and then the temperature was decreased at a rate of 100℃ / min. The sample was cooled to -10°C using a 2000W centrifuge and then held at -10°C for 3 minutes. This cycle was repeated twice. From the results of the first DSC measurement, it was found that the glass transition temperature of YGTBi1BP-02 was 142°C. It was revealed that this material has extremely high heat resistance.

[0450] In addition, thermogravimetry and differential thermal analysis (TTA) of YGTBi1BP-02 try-Differential Thermal Analysis:TG-DTA The measurements were carried out using a high vacuum differential thermobalance (manufactured by Bruker AXS Co., Ltd.). The measurement was carried out at atmospheric pressure with a temperature rise rate of 10°C / m The measurements were carried out under nitrogen flow (flow rate 200 mL / min). In this case, the weight of YGTBi1BP-02 obtained by thermogravimetry was -5% of the weight at the start of the measurement. It was found that the temperature at which it becomes decomposed (decomposition temperature) is 500°C or higher, making it a highly heat-resistant substance. It was shown that [Explanation of symbols]

[0451] 101: first electrode, 102: second electrode, 103: EL layer, 111: hole injection layer, 11 2: hole transport layer, 112-1: first hole transport layer, 112-2: second hole transport layer, 11 3: 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: seal material, 407: sealing substrate, 412: pad, 420: IC chip, 501: anode, 502: Cathode, 511: first light-emitting unit, 512: second light-emitting unit, 513: charge generation layer 601: driver circuit section (source line driver circuit), 602: pixel section, 603: driver circuit section (gate 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 Electrode, 953: insulating layer, 954: partition wall layer, 955: EL layer, 956: electrode, 1001 substrate , 1002 Underlying insulating film, 1003 Gate insulating film, 1006 Gate electrode, 1007 Gate electrode, 1008 gate electrode, 1020 first interlayer insulating film, 1021 second layer Interlayer insulating film, 1022 Electrode, 1024W First electrode, 1024R First electrode, 102 4G first electrode, 1024B first electrode, 1025 partition wall, 1028 EL layer, 10 29 second electrode, 1031 sealing substrate, 1032 sealing material, 1033 transparent base material, 1034R Red color layer, 1034G Green color layer, 1034B Blue color layer, 1 035 black matrix, 1036 overcoat layer, 1037 third interlayer insulation Film, 1040 pixel unit, 1041 drive circuit unit, 1042 peripheral unit, 2001 housing, 2 002: Light source, 2100: Robot, 2110: Computing device, 2101: Illuminance sensor, 21 02: Microphone, 2103: Upper camera, 2104: Speaker, 2105: Display Play, 2106: Lower camera, 2107: Obstacle sensor, 2108: Moving mechanism, 300 1: lighting device, 5000: housing, 5001: display unit, 5002: second display unit, 5003 :Speaker, 5004:LED lamp, 5005:Operation keys, 5006:Connection terminal, 50 07: Sensor, 5008: Microphone, 5012: Support, 5013: Earphone, 5 100: Cleaning robot, 5101: Display, 5102: Camera, 5103: Brush 5104: Operation buttons, 5150: Mobile information terminal, 5151: Housing, 5152: Display area area, 5153: bend, 5120: dust, 5200: display area, 5201: display area, 5 202: Display area, 5203: Display area, 7101: Housing, 7103: Display section, 7105 : Stand, 7107: Display unit, 7109: Operation keys, 7110: Remote control unit, 72 01: Main unit, 7202: Housing, 7203: Display unit, 7204: Keyboard, 7205: External a display connection port, 7206: pointing device, 7210: second display unit, 7401 : Housing, 7402: Display unit, 7403: Operation buttons, 7404: External connection port, 740 5: Speaker, 7406: Microphone, 7400: Mobile phone, 9310: Mobile information terminal, 9 311: Display panel, 9312: Display area, 9313: Hinge, 9315: Housing

Claims

1. An organic compound having a HOMO level of -5.7 eV or more and -5.4 eV, The organic compound is an organic compound represented by any one of the following formulas: 【Chemistry 1】

2. An electronic device comprising a hole injection layer having the organic compound according to claim 1.

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