Organic compound

Abstract

To provide a novel organic compound.SOLUTION: An organic compound herein is a triarylamine derivative, wherein one aryl group in the organic compound is an aryl group including a skeleton in which a naphthyl group is bonded to a naphthylene group. The other two aryl groups are each independently a phenyl group, a biphenyl group, or a terphenyl group. These groups may each have a substituent. As the substituent, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms can be selected.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] Some display devices and light-emitting devices using organic EL elements have been put into practical use, and their applications are expanding. As the usage scenarios expand, it is expected to be used in harsh situations. As a result, there is an increasing demand for reliability.

[0003] On the other hand, the requirements for light-emitting and display properties are becoming more sophisticated, and the carrier transport In the case of a conductive material, its transport properties and energy levels are important as well as its reliability.

[0004] Patent Document 1 discloses a hole transport material having a triarylamine structure and excellent properties. are. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2010-202633 Summary of the Invention [Problem to be solved by the invention]

[0006] An object of one embodiment of the present invention is to provide a novel organic compound. In one aspect, an object of the present invention is to provide a novel carrier transport material. In another aspect of the present invention, a novel hole transport material is provided. The object of the present invention is to provide a hole transport material having a high glass transition temperature (Tg). In one embodiment of the present invention, an object is to provide a novel material for a light-emitting element. In one embodiment, the present invention provides a light-emitting element having a long service life when used in a light-emitting element. The purpose is to provide materials.

[0007] Another object of one embodiment of the present invention is to provide a novel light-emitting element. An object of the present invention is to provide a good light-emitting element.

[0008] 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 aspect of the present invention is to provide a light-emitting device with good display quality. The present invention aims to provide a device, an electronic device, and a display device.

[0009] The present invention is intended to solve any one of the above problems. [Means for solving the problem]

[0010] One embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0011] [ka]

[0012] However, in general formula (G1), R 1 ~R 10 are each independently hydrogen, a group having 1 to 10 carbon atoms, 6 alkyl groups, cycloalkyl groups having 3 to 6 carbon atoms, and the following general formulas (R-1) to (R -4), and R 11 ~R 14 are independently hydrogen, carbon It represents any one of an alkyl group having 1 to 6 carbon atoms and a cycloalkyl group having 3 to 6 carbon atoms. Furthermore, n represents a value of 0, 1, or 2, and when n is 2, two phenylene groups may each have a different substituent. Naph is represented by the following general formula (g1-1): or a group represented by the following general formula (g1-2).

[0013] [ka]

[0014] However, in the general formulae (R-1) to (R-4), R 60 ~R 91 are each independently a nitrogen atom, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 3 to 6 carbon atoms; is.

[0015] [ka]

[0016] However, in general formula (g1-1), R 22 ~R 28 One of them is the following general formula (g2 -1) or a group represented by the following general formula (g2-2), and the rest are independently selected from hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 3 to 6 carbon atoms; In addition, in the general formula (g1-2), R 31 ~R 37 One of them is below a group represented by the following general formula (g2-1) or a group represented by the following general formula (g2-2): the remainders are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cyclo group having 3 to 6 carbon atoms. represents any one of the alkyl groups.

[0017] [ka]

[0018] However, in general formula (g2-1), R 42 ~R 48 are independently hydrogen, carbon number 1 It represents any one of an alkyl group having from 1 to 6 carbon atoms and a cycloalkyl group having from 3 to 6 carbon atoms. In general formula (g2-2), R 51 ~R 57 are each independently hydrogen, a group having 1 to 10 carbon atoms, and a cycloalkyl group having 3 to 6 carbon atoms.

[0019] Another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0020] [ka]

[0021] However, in general formula (G1), R 1 ~R 10 are each independently hydrogen, a group having 1 to 10 carbon atoms, 6 alkyl groups, cycloalkyl groups having 3 to 6 carbon atoms, and the following general formulas (R-1) to (R -4), and R 11~R 14 are independently hydrogen, carbon It represents any one of an alkyl group having 1 to 6 carbon atoms and a cycloalkyl group having 3 to 6 carbon atoms. Furthermore, n represents a value of 0, 1, or 2, and when n is 2, two phenylene groups may each have a different substituent. Naph is represented by the following general formula (g1-2): It is a group that can be

[0022] [ka]

[0023] However, in the general formulae (R-1) to (R-4), R 60 ~R 91 are each independently a nitrogen atom, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 3 to 6 carbon atoms; is.

[0024] [ka]

[0025] However, in general formula (g1-2), R 31 ~R 37 One of them is the following general formula (g2- 1) or a group represented by the following general formula (g2-2), and the remainder is each independently and optionally hydrogen, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms. It represents one of them.

[0026] [ka]

[0027] However, in general formula (g2-1), R 42 ~R 48 are independently hydrogen, carbon number 1 It represents any one of an alkyl group having from 1 to 6 carbon atoms and a cycloalkyl group having from 3 to 6 carbon atoms. In general formula (g2-2), R 51 ~R 57 are each independently hydrogen, a group having 1 to 10 carbon atoms, and a cycloalkyl group having 3 to 6 carbon atoms.

[0028] Another embodiment of the present invention is an organic compound represented by the following general formula (G2).

[0029] [ka]

[0030] However, in general formula (G2), R 1 , R 2 , R 4 ~R 7 , R 9 ~R 14 and R 1 00 ~R 109 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, and a group having 3 carbon atoms. represents any one of the cycloalkyl groups of the groups listed in the above to 6, and n is a value of 0, 1, or 2. When n is 2, the two phenylene groups may each have a different substituent. Furthermore, naph is a group represented by the following general formula (g1-2).

[0031] [ka]

[0032] However, in general formula (g1-2), R 31 ~R 37 One of them is the following general formula (g2- 1) or a group represented by the following general formula (g2-2), and the remainder is each independently and optionally hydrogen, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms. It represents one of them.

[0033] [ka]

[0034] However, in general formula (g2-1), R 42 ~R 48 are independently hydrogen, carbon number 1 It represents any one of an alkyl group having from 1 to 6 carbon atoms and a cycloalkyl group having from 3 to 6 carbon atoms. In general formula (g2-2), R 51 ~R 57 are each independently hydrogen, a group having 1 to 10 carbon atoms, and a cycloalkyl group having 3 to 6 carbon atoms.

[0035] Another embodiment of the present invention is an organic compound represented by the following general formula (G3).

[0036] [ka]

[0037] However, in general formula (G3), R 1 , R 2 , R 4 ~R 7 , R 9 , R 10 , R 100 No To R 109 and R 111 ~R 114 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, naph represents one of the following alkyl groups and cycloalkyl groups having 3 to 6 carbon atoms: It is a group represented by the following general formula (g1-2).

[0038] [ka]

[0039] However, in general formula (g1-2), R 31 ~R 37 One of them is the following general formula (g2- 1) or a group represented by the following general formula (g2-2), and the remainder is each independently and optionally hydrogen, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms. It represents one of them.

[0040] [ka]

[0041] However, in general formula (g2-1), R 42 ~R 48 are independently hydrogen, carbon number 1 It represents any one of an alkyl group having from 1 to 6 carbon atoms and a cycloalkyl group having from 3 to 6 carbon atoms. In general formula (g2-2), R 51 ~R 57 are each independently hydrogen, a group having 1 to 10 carbon atoms, and a cycloalkyl group having 3 to 6 carbon atoms.

[0042] Another embodiment of the present invention is an organic compound represented by the following general formula (G4).

[0043] [ka]

[0044] However, in general formula (G4), R 1 , R 2 , R 4 ~R 7 , R 9 , R 10 , and R 1 00 ~R 109are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, and a group having 3 carbon atoms. Naph represents any one of the cycloalkyl groups represented by the following general formula (g1-2): It is a group represented by the formula:

[0045] [ka]

[0046] However, in general formula (g1-2), R 31 ~R 37 One of them is the following general formula (g2- 1) or a group represented by the following general formula (g2-2), and the remainder is each independently and optionally hydrogen, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms. It represents one of them.

[0047] [ka]

[0048] However, in general formula (g2-1), R 42 ~R 48 are independently hydrogen, carbon number 1 It represents any one of an alkyl group having from 1 to 6 carbon atoms and a cycloalkyl group having from 3 to 6 carbon atoms. In general formula (g2-2), R 51 ~R 57 are each independently hydrogen, a group having 1 to 10 carbon atoms, and a cycloalkyl group having 3 to 6 carbon atoms.

[0049] Another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0050] [ka]

[0051] However, in general formula (G1), R 1 ~R 10 are each independently hydrogen, a group having 1 to 10 carbon atoms, 6 alkyl groups, cycloalkyl groups having 3 to 6 carbon atoms, and the following general formulas (R-1) to (R -4), and R 11 ~R 14 are independently hydrogen, carbon It represents any one of an alkyl group having 1 to 6 carbon atoms and a cycloalkyl group having 3 to 6 carbon atoms. Furthermore, n represents a value of 0, 1, or 2, and when n is 2, two phenylene groups may each have a different substituent. Naph is represented by the following general formula (g1-1): or a group represented by the following general formula (g1-2).

[0052] [ka]

[0053] However, in the general formulae (R-1) to (R-4), R 60 ~R 91 are each independently a nitrogen atom, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 3 to 6 carbon atoms; is.

[0054] [ka]

[0055] However, in general formula (g1-1), R 22 ~R 28 One of them is the following general formula (g2 -2), and the remaining groups are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, and and a cycloalkyl group having 3 to 6 carbon atoms. In R 31~R 37 one of which is a group represented by the following general formula (g2-2): the remainders are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cyclo group having 3 to 6 carbon atoms. represents any one of the alkyl groups.

[0056] [ka]

[0057] However, in general formula (g2-2), R 51 ~R 57 are independently hydrogen, carbon number 1 and represents any one of an alkyl group having from 1 to 6 carbon atoms and a cycloalkyl group having from 3 to 6 carbon atoms.

[0058] Another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0059] [ka]

[0060] However, in general formula (G1), R 1 ~R 10 are each independently hydrogen, a group having 1 to 10 carbon atoms, 6 alkyl groups, cycloalkyl groups having 3 to 6 carbon atoms, and the following general formulas (R-1) to (R -4), and R 11 ~R 14 are independently hydrogen, carbon It represents any one of an alkyl group having 1 to 6 carbon atoms and a cycloalkyl group having 3 to 6 carbon atoms. Furthermore, n represents a value of 0, 1, or 2, and when n is 2, two phenylene groups may each have a different substituent. Naph is represented by the following general formula (g1-1): or a group represented by the following general formula (g1-2).

[0061] [ka]

[0062] However, in the general formulae (R-1) to (R-4), R 60 ~R 91 are each independently a nitrogen atom, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 3 to 6 carbon atoms; is.

[0063] [ka]

[0064] However, in general formula (g1-1), R 22 ~R 28 One of them is the following general formula (g2 -1), and the remaining groups are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, and and a cycloalkyl group having 3 to 6 carbon atoms. In R 31 ~R 37 one of which is a group represented by the following general formula (g2-1): the remainders are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cyclo group having 3 to 6 carbon atoms. represents any one of the alkyl groups.

[0065] [ka]

[0066] However, in general formula (g2-1), R 42 ~R 48 are independently hydrogen, carbon number 1 and represents any one of an alkyl group having from 1 to 6 carbon atoms and a cycloalkyl group having from 3 to 6 carbon atoms.

[0067] Another embodiment of the present invention is an organic compound having the above structure, wherein R 31 ~R 37 That one is a group represented by the following general formula (g2-2), and the rest are each independently hydrogen, an organic group selected from the group consisting of an alkyl group having 1 to 6 carbon atoms and a cycloalkyl group having 3 to 6 carbon atoms; It is a compound.

[0068] [ka]

[0069] However, in general formula (g2-2), R 51 ~R 57 are independently hydrogen, carbon number 1 and represents any one of an alkyl group having from 1 to 6 carbon atoms and a cycloalkyl group having from 3 to 6 carbon atoms.

[0070] Another embodiment of the present invention is an organic compound having the above structure, wherein R 31 ~R 37 is R 36 is a group represented by the general formula (g2-2), and the rest are each independently hydrogen, an organic group selected from the group consisting of an alkyl group having 1 to 6 carbon atoms and a cycloalkyl group having 3 to 6 carbon atoms; It is a compound.

[0071] Another embodiment of the present invention is an organic compound having the above structure, wherein R 31 ~R 37 That one is a group represented by the following general formula (g2-1), and the rest are each independently hydrogen, an organic group selected from the group consisting of an alkyl group having 1 to 6 carbon atoms and a cycloalkyl group having 3 to 6 carbon atoms; It is a compound.

[0072] [ka]

[0073] However, in general formula (g2-1), R 42 ~R 48 are independently hydrogen, carbon number 1 and represents any one of an alkyl group having from 1 to 6 carbon atoms and a cycloalkyl group having from 3 to 6 carbon atoms.

[0074] One embodiment of the present invention is a light-emitting element including an organic compound having any of the above structures.

[0075] One embodiment of the present invention is a light-emitting element including a light-emitting element having any of the above structures and a transistor or a substrate. It is a light-emitting device.

[0076] Another embodiment of the present invention is a light-emitting device having the above structure, a sensor, an operation button, a speaker, Or, it is an electronic device having a microphone.

[0077] Another embodiment of the present invention is a lighting device including a light-emitting device having the above structure and a housing. .

[0078] 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]

[0079] According to one embodiment of the present invention, a novel light-emitting element can be provided. Alternatively, a light-emitting element having good luminous efficiency can be provided. Alternatively, a light-emitting element with high heat resistance can be provided.

[0080] 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.

[0081] 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]

[0082] [Figure 1] Schematic diagram of a light-emitting element. [Figure 2] 1A to 1C illustrate an example of a method for manufacturing a light-emitting element. [Figure 3] 1A to 1C illustrate an example of a method for manufacturing a light-emitting element. [Figure 4] 1 is a conceptual diagram of an active matrix light-emitting device. [Figure 5] 1 is a conceptual diagram of an active matrix light-emitting device. [Figure 6] 1 is a conceptual diagram of an active matrix light-emitting device. [Figure 7] FIG. 1 is a conceptual diagram of a passive matrix light-emitting device. [Figure 8] FIG. [Figure 9] 1 is a diagram showing an electronic device. [Figure 10] FIG. [Figure 11] FIG. [Figure 12] FIG. [Figure 13] FIG. 2 is a diagram illustrating an in-vehicle display device and a lighting device. [Figure 14] 1 is a diagram showing an electronic device. [Figure 15] 1 is a diagram showing an electronic device. [Figure 16] 1H-NMR spectrum of BBA(βN2)B. [Figure 17] Absorption and emission spectra of solutions of BBA(βN2)B. [Figure 18] Absorption and emission spectra of thin films of BBA(βN2)B. [Figure 19] 1H-NMR spectrum of BBA(βN2). [Figure 20] Absorption and emission spectra of solutions of BBA(βN2). [Figure 21] Absorption and emission spectra of thin films of BBA(βN2). [Figure 22] 1H-NMR spectrum of BBA(βN2)B-02. [Figure 23] Absorption and emission spectra of thin films of BBA(βN2)B-02. [Figure 24] 1H-NMR spectrum of BBA(βN2)B-03. [Figure 25] 1H-NMR spectrum of BBAαNβNB. [Figure 26] 1H-NMR spectrum of BBAαNβNB-02. [Figure 27] 1H-NMR spectrum of BBAαNβNB-03. [Figure 28] Luminance-current density characteristics of light-emitting element 1 and light-emitting element 2. [Figure 29] Current efficiency-luminance characteristics of Light-emitting element 1 and Light-emitting element 2. [Figure 30] luminance-voltage characteristics of light-emitting element 1 and light-emitting element 2. [Figure 31] Current-voltage characteristics of light-emitting element 1 and light-emitting element 2. [Figure 32]External quantum efficiency-luminance characteristics of light-emitting element 1 and light-emitting element 2. [Figure 33] 1 shows the emission spectra of light-emitting element 1 and light-emitting element 2. [Figure 34] Normalized luminance vs. time change characteristics of light-emitting element 1 and light-emitting element 2. [Figure 35] luminance-current density characteristics of light-emitting elements 3 and 4. [Figure 36] Current efficiency-luminance characteristics of Light-emitting element 3 and Light-emitting element 4. [Figure 37] luminance-voltage characteristics of light-emitting element 3 and light-emitting element 4. [Figure 38] Current-voltage characteristics of light-emitting element 3 and light-emitting element 4. [Figure 39] External quantum efficiency-luminance characteristics of light-emitting element 3 and light-emitting element 4. [Figure 40] 1 shows the emission spectra of light-emitting elements 3 and 4. [Figure 41] Normalized luminance vs. time change characteristics of light-emitting element 3 and light-emitting element 4. [Figure 42] luminance-current density characteristics of light-emitting elements 5 and 6. [Figure 43] Current efficiency-luminance characteristics of light-emitting element 5 and light-emitting element 6. [Figure 44] luminance-voltage characteristics of light-emitting element 5 and light-emitting element 6. [Figure 45] Current-voltage characteristics of light-emitting element 5 and light-emitting element 6. [Figure 46] External quantum efficiency-luminance characteristics of light-emitting elements 5 and 6. [Figure 47] 1 shows the emission spectra of light-emitting elements 5 and 6. [Figure 48] Normalized luminance vs. time change characteristics of light-emitting element 5 and light-emitting element 6. [Figure 49] Luminance-current density characteristics of light-emitting elements 7 and 8. [Figure 50] Current efficiency-luminance characteristics of light-emitting element 7 and light-emitting element 8. [Figure 51] luminance-voltage characteristics of light-emitting element 7 and light-emitting element 8. [Figure 52]Current-voltage characteristics of light-emitting element 7 and light-emitting element 8. [Figure 53] External quantum efficiency-luminance characteristics of light-emitting elements 7 and 8. [Figure 54] 1 shows the emission spectra of light-emitting elements 7 and 8. [Figure 55] Luminance-current density characteristics of light-emitting elements 9 and 10. [Figure 56] Current efficiency-luminance characteristics of light-emitting element 9 and light-emitting element 10. [Figure 57] luminance-voltage characteristics of light-emitting element 9 and light-emitting element 10. [Figure 58] Current-voltage characteristics of light-emitting element 9 and light-emitting element 10. [Figure 59] External quantum efficiency-luminance characteristics of light-emitting elements 9 and 10. [Figure 60] 1 shows the emission spectra of light-emitting elements 9 and 10. [Figure 61] Luminance-current density characteristics of light-emitting element 11 and light-emitting element 12. [Figure 62] Current efficiency-luminance characteristics of light-emitting element 11 and light-emitting element 12. [Figure 63] luminance-voltage characteristics of light-emitting element 11 and light-emitting element 12. [Figure 64] Current-voltage characteristics of light-emitting element 11 and light-emitting element 12. [Figure 65] External quantum efficiency-luminance characteristics of light-emitting elements 11 and 12. [Figure 66] 1 shows the emission spectra of light-emitting element 11 and light-emitting element 12. [Figure 67] Luminance-current density characteristics of light-emitting elements 13 and 14. [Figure 68] Current efficiency-luminance characteristics of light-emitting element 13 and light-emitting element 14. [Figure 69] luminance-voltage characteristics of light-emitting element 13 and light-emitting element 14. [Figure 70] Current-voltage characteristics of light-emitting element 13 and light-emitting element 14. [Figure 71] External quantum efficiency-luminance characteristics of light-emitting elements 13 and 14. [Figure 72] 1 shows the emission spectra of light-emitting element 13 and light-emitting element 14. [Figure 73] 1H-NMR spectrum of 3-bromo-2,2'-binaphthyl. [Figure 74] 1H-NMR spectrum of 3-bromo-2,1'-binaphthyl. [Figure 75] 1H-NMR spectrum of BBAβNαNB. [Figure 76] 1H-NMR spectrum of BBAβNαNB-02. DETAILED DESCRIPTION OF THE INVENTION

[0083] 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 embodiments and details thereof may be modified 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 can be made to the above. The present invention should not be construed as being limited to the description of the embodiments.

[0084] (Embodiment 1) The organic compound of one embodiment of the present invention is a triarylamine derivative, It is an organic compound in which one aryl group is an aryl group containing a binaphthyl skeleton. The aryl group is an aryl group containing a naphthylene group skeleton having a naphthyl group. The remaining two aryl groups in the triarylamine derivative are are each independently a phenyl group, a biphenyl group, or a terphenyl group. These groups may have a substituent, and the substituent may be an alkyl group having 1 to 6 carbon atoms. A cycloalkyl group having 3 to 6 carbon atoms can be selected.

[0085] The aryl group containing the naphthylene group skeleton having the naphthyl group is an aryl group containing the naphthylene group and an aryl group containing the naphthylene group. An arylene group may further be present between the nitrogen atom and the alkyl group. The arylene group may be any of the following: A phenylene group or a biphenylene group can be selected. The arylene group can have a substituent The substituent may be an alkyl group having 1 to 6 carbon atoms, or Three to six cycloalkyl groups can be selected.

[0086] The naphthylene group has bonds at any two of the 2-, 3-, 6- and 7-positions. one of the bonds is bonded to the nitrogen of the amine or the arylene group, and the other is Considering the reactivity of the naphthalene skeleton, the structure of bonding with the naphthyl group is This is preferable because the synthesis becomes easy and the production cost of the target product is reduced. When the 2-position is bonded to the nitrogen of the amine or the arylene group, the 3-position, 6-position, The reactivity of the naphthalene skeleton is improved by bonding either one of the 1st and 7th positions to the naphthyl group. Considering this, it is preferable because it makes it easier to synthesize raw materials and reduces the manufacturing cost of the target product. Furthermore, it is possible to provide materials with high heat resistance, reliability, or carrier transport properties. Furthermore, the naphthylene group has bonds at the 2- and 6-positions, and the bonds one of which is bonded to the nitrogen of the amine or the arylene group, and the other is bonded to the naphthyl group This is preferable in order to obtain a light-emitting device having good heat resistance, reliability, or carrier transportability. It is a simple configuration.

[0087] Furthermore, the naphthyl group is preferably a 2-naphthyl group, which provides a highly reliable light-emitting element. Therefore, it is preferable.

[0088] The organic compound according to one embodiment of the present invention can be represented by the following general formula (G1). Cut.

[0089] [ka]

[0090] In general formula (G1), R 1 ~R 10 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, alkyl groups, cycloalkyl groups having 3 to 6 carbon atoms, and the following general formulas (R-1) to (R-4) ) represents any one of the groups represented by the formula (I). 1 ~R 5 , R 6 ~R 10 In each each of the groups represented by the general formulas (R-1) to (R-4) below, and the remaining groups each independently represent hydrogen. and an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms. It is preferable that R 1 ~R 5 , R 6 ~R 10 In each of the following general When the compound is represented by any one of formulas (R-1) to (R-4), the remainder is hydrogen. This is preferable in that it can be easily manufactured and inexpensively.

[0091] [ka]

[0092] However, in the groups represented by the general formulae (R-1) to (R-4), R 60 ~R 91 is that each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 3 to 6 carbon atoms; Represents one of the following: R 60 ~R91 From a cost perspective, all hydrogen is needed. This is a preferred configuration.

[0093] In addition, in general formula (G1), R 11 ~R 14 are independently hydrogen, carbon number 1 or more It represents any one of an alkyl group having from 1 to 6 carbon atoms and a cycloalkyl group having from 3 to 6 carbon atoms. n represents a value of 0, 1, or 2, and when n is 2, two phenylene groups are bonded. The substituents on each phenylene group and their positions are different. It is also possible to use n=1. The substance has high sublimation properties and high heat resistance. Therefore, it is preferable.

[0094] In the general formula (G1), naph is represented by the following general formula (g1-1) or general formula (g1 -2).

[0095] [ka]

[0096] However, in the above general formula (G1), when naph is the general formula (g1-1), In (g1‐1), R 22 ~R 28 One of them is represented by the following general formula (g2-1): or a group represented by the following general formula (g2-2), and the remainders are each independently hydrogen, any one of an alkyl group having 1 to 6 carbon atoms and a cycloalkyl group having 3 to 6 carbon atoms; do.

[0097] In the organic compound represented by the general formula (G1), naph is ) is preferable because it is easy to provide a highly reliable light-emitting element. It's nice.

[0098] In addition, in the above general formula (G1), when naph is the general formula (g1-2), In (g1‐2), R 31 ~R 37 One of them is represented by the following general formula (g2-1): or a group represented by the following general formula (g2-2), and the remaining groups are each independently hydrogen, carbon, or the like. represents one of an alkyl group having 1 to 6 prime numbers and a cycloalkyl group having 3 to 6 carbon atoms .

[0099] [ka]

[0100] However, the substituent of the general formula (g1-1) or (g1-2) is the general formula (g2-1) In the case where R 42 ~R 48 are each unique and optionally hydrogen, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms. It represents one of them.

[0101] In addition, the substituent of the general formula (g1-1) or (g1-2) is the general formula (g2-2) When R 51 ~R 57 are independently hydrogen, carbon represents one of an alkyl group having 1 to 6 prime numbers and a cycloalkyl group having 3 to 6 carbon atoms .

[0102] The groups represented by the general formula (g2-1) and the general formula (g2-2) are represented by the general formula (g2 Selecting the group represented by -2) is preferable from the viewpoint of providing a highly reliable light-emitting element. By selecting the group represented by general formula (g2-1), a light-emitting element with good heat resistance or carrier transport properties can be obtained. This is preferable from the perspective of providing children.

[0103] In addition, in the organic compound represented by the general formula (G1), R 1 ~R 5 , R 6 ~R 1 0 are each independently a group represented by the general formula (R-1), and the remaining groups are each independently a hydrogen atom, a carbon atom, a It is either an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms. In this case, the substituent represented by the general formula (R-1) is preferably R 3 and R 8 place That is, a preferred embodiment of the present invention is a compound represented by the following general formula: It is an organic compound represented by (G2).

[0104] [ka]

[0105] In the organic compound represented by the general formula (G2), R 1 , R 2 , R 4 ~R 7 , R 9 oh Yobi R 10 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, and a represents any one of cycloalkyl groups. 11 ~R 14 and R 100 ~R 1 09 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 3 to 6 carbon atoms. In addition, n represents a value of 0, 1, or 2, and when n is 2, In this case, it represents a structure in which two phenylene groups are bonded, but each phenylene group is The substituents and their positions may be different.

[0106] Also, R 1 , R 2 , R 4 ~R 7 , R 9 ~R 14 and R 100 ~R 109 is all water The basic structure is easy to synthesize and the materials are readily available, making it possible to manufacture it inexpensively. This is a desirable configuration.

[0107] In the organic compound represented by the general formula (G2), naph is Since the organic compound represented by the formula (I) is similar to that of the organic compound represented by the formula (I), the description thereof will be omitted.

[0108] In the organic compound represented by the general formula (G2), n is 1 as described above. is preferable because it is possible to provide a substance that has both high sublimability and high heat resistance. That is, it is preferable that the organic compound be an organic compound represented by the following general formula (G3).

[0109] [ka]

[0110] In the organic compound represented by the general formula (G3), naphtha, R 1 , R 2 , R 4 ~R 7 , R 9 , R 10 and R 100 ~R 109 is an organic compound represented by the above general formula (G1). Since it is the same as the organic compound represented by the general formula (G2) above, the description thereof is omitted. In the above general formula (G3), R 111 ~R 114 are independently hydrogen, carbon number It represents any one of an alkyl group having 1 to 6 carbon atoms and a cycloalkyl group having 3 to 6 carbon atoms.

[0111] In the organic compound represented by the general formula (G2), when n is 0, n is 1 or 2. In other words, the HOMO is shallower than that of the compound represented by the following general formula (G4). The organic compound is one embodiment of a preferred configuration when a substance with a shallower HOMO level is required.

[0112] [ka]

[0113] In the organic compound represented by the general formula (G4), naphtha, R 1 , R 2 , R 4 ~R 7 , R 9 , R 10 and R 100 ~R 109 is an organic compound represented by the above general formula (G1). Since it is the same as the organic compound represented by the general formula (G2) above, the description thereof is omitted. .

[0114] In the organic compounds represented by the general formulas (G1) to (G4), naphthyl is a group represented by the general formula (g1-2) in which a group represented by the general formula (g2-2) is added to a group represented by the general formula (g1-2). It is preferable that the group having the group bonded thereto is one having a high reliability, since it provides a highly reliable element. In the formula (g1-2), R 36 is represented by the above general formula (g2-2) It is more preferable that the group is a group represented by the formula:

[0115] Examples of specific structures of the organic compounds of the present invention as described above are shown below.

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[0117] [ka]

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[0125] [ka]

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[0130] [ka]

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[0133] Next, an example of a method for synthesizing the organic compound of the present invention as described above will be described. G1) will be used as an example to explain this.

[0134] The organic compound of one embodiment of the present invention represented by general formula (G1) can be synthesized by the following synthesis scheme (a-1): That is, the diarylamine compound (compound 1) and the vinyl group can be synthesized as follows. By coupling with a butyl compound (compound 2), the target compound (G1) can be obtained. The synthesis scheme (a-1) is shown below.

[0135] [ka]

[0136] In the synthesis scheme (a-1), X 1 represents a chlorine atom, a bromine atom, an iodine atom, or a triflate group.

[0137] Synthetic scheme (a-1) shows the palladium-catalyzed Buchwald-Hartwig reaction. When carrying out this reaction, the palladium catalyst is preferably a bis(dibenzyl) diphenylideneacetone)palladium(0), palladium(II) acetate, [1,1-bis(diphenyl (phenylphosphino)ferrocene]palladium(II) dichloride, tetrakis(triphenylphosphino)ferrocene (arylphosphine)palladium(0), allylpalladium(II) chloride (dimer), etc. The following palladium compounds can be used. tri(n-hexyl)phosphine, tricyclohexylphosphine, Di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphino-2 ',6'-Dimethoxybiphenyl, tri(ortho-tolyl)phosphine, di-tert- Butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (abbreviation: cBRI DP (registered trademark) can be used. organic bases such as thioxide, and inorganic bases such as potassium carbonate, cesium carbonate, and sodium carbonate In this reaction, toluene, xylene, benzene, tetrahydrofuran, etc. can be used as a solvent. Tetrahydrofuran, dioxane, etc. can be used in this reaction. The reagents are not limited to those mentioned above.

[0138] In addition, when the synthesis scheme (a-1) is carried out by the Ullmann reaction, it can be used The reagent may be copper or a copper compound, and the base may be an inorganic base such as potassium carbonate. The solvent that can be used in this reaction is 1,3-dimethyl-3,4,5,6-tetramethyl-2,4 ... tetrahydro-2(1H)pyrimidinone (DMPU), toluene, xylene, benzene, etc. In the Ullmann reaction, a reaction temperature of 100°C or higher results in a shorter reaction time and a higher yield. It is preferable to use DMPU or xylene, which have high boiling points, in order to obtain the target product. The reaction temperature is preferably higher than 150°C, and therefore DMPU is more preferably used. The reagents that can be used in this reaction are limited to those mentioned above. It's not something like that.

[0139] The organic compound represented by the general formula (G1) of the present invention can be synthesized as shown in the following synthesis scheme (a-2). It is also possible to synthesize a triarylamine compound (compound 3) and a binaphthylamine compound. By coupling with the aryl compound (compound 4), the target compound (G1) can be obtained. The synthesis scheme (a-2) is shown below.

[0140] [ka]

[0141] In the synthesis scheme (a-2), X 2 and X 3 are each independently a halogen, a boronic acid group, organoboron group, triflate group, organotin group, organozinc group, or magnesium halide group The halogen is preferably chlorine, bromine, or iodine, and is more preferably chlorine, bromine, or iodine in consideration of reactivity. Preferably, it is bromine or iodine, and in consideration of cost, it is more preferably chlorine or bromine. .

[0142] In synthetic scheme (a-2), the Suzuki-Miyaura coupling reaction using a palladium catalyst If you do, X 2 and X 3 is a halogen group, a boronic acid group, an organoboron group, or a triflate The halogen is preferably iodine, bromine or chlorine. Dibenzylideneacetone)palladium(0), palladium(II) acetate, [1,1-bis (Diphenylphosphino)ferrocene]palladium(II) dichloride, tetrakis(trimethylsilyl) Palladium compounds such as triphenylphosphine palladium(0) and tri(tert-butylphosphine)palladium(0) tri(n-hexyl)phosphine, tricyclohexylphosphine, Di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphino-2 Using ligands such as ',6'-dimethoxybiphenyl and tri(ortho-tolyl)phosphine, In this reaction, organic bases such as sodium tert-butoxide and carbonates are used. Inorganic bases such as potassium carbonate, cesium carbonate, sodium carbonate, etc. can be used.

[0143] In this reaction, the solvents used are toluene, xylene, benzene, tetrahydrofuran, dihydrofuran, Xanthan Gum, Ethanol, Methanol, Water, Diethylene Glycol Dimethyl Ether, Ethylene Glycol monomethyl ether and the like can be used in this reaction. The reagents that can be used are not limited to these.

[0144] The reaction shown in synthetic scheme (a-2) is a reaction using organotin compounds. Coupling reaction, Kumada-Tamao-Corleau coupling reaction using Grignard reagents, Negishi coupling reaction using organozinc compounds, reactions using copper or copper compounds, etc. It can be done.

[0145] When the reaction is carried out using the Migita-Kosugi-Stille coupling reaction, X 2 and X 3 are respectively One of them represents an organotin group and the other represents a halogen. That is, Compound 3 and One of the compounds 4 is an organotin compound and the other is a halide. When the reaction is carried out using the Kumada-Tamao-Corleau coupling reaction, X 2 and X 3 Hado One of them represents a magnesium halide group, and the other represents a halogen. Either Compound 3 or Compound 4 is a Grignard reagent, and the other is a halo When using the Negishi coupling reaction, X 2 and X 3 Either one is organic One represents a zinc group, and the other represents a halogen. That is, which of Compound 3 and Compound 4 One is an organozinc compound and the other is a halide.

[0146] The method for synthesizing the organic compound (G1) of the present invention is shown in the synthesis scheme (a-1) or is not limited to (a-2).

[0147] In the above reaction scheme, R 1 ~R 14 , n, naph, the general formula (G 1) and the organic compounds represented by the formula (I) are the same as those described above. The reply statement is omitted.

[0148] (Embodiment 2) An example of a light-emitting element according to one embodiment of the present invention will be described in detail below with reference to FIG.

[0149] The light-emitting element in this embodiment has a pair of electrodes consisting of an anode 101 and a cathode 102. The device is composed of an anode 101, a cathode 102 and an EL layer 103 disposed between them.

[0150] The anode 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 or a mixture thereof. , indium tin oxide (ITO), silicon dioxide or silicon oxide-containing indium oxide-tin oxide, indium oxide-zinc oxide, acid Examples include tungsten oxide and indium oxide containing zinc oxide (IWZO). These conductive metal oxide films are usually formed by sputtering, but they can also be formed by the sol-gel method. It is also possible to fabricate it by applying the method described above. An example of the fabrication method is indium oxide-zinc oxide. The target is made by adding 1 wt% to 20 wt% of zinc oxide to indium oxide. In addition, tungsten oxide and acid are used to form the film. Indium oxide containing zinc oxide (IWZO) is a tungsten oxide-containing indium oxide. Contains 0.5wt% to 5wt% of zinc and 0.1wt% to 1wt% of zinc oxide. It can also be formed by sputtering using a target. , Platinum (Pt), Nickel (Ni), Tungsten (W), Chromium (Cr), Molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), aluminum Examples of the material include aluminum (Al), and nitrides of metal materials (for example, titanium nitride). Graphene can also be used. When a composite material containing the above is used, an electrode material other than those mentioned above may also be selected regardless of the work function. It is also possible.

[0151] The hole injection layer 111 may be formed of a first substance having a relatively high acceptor property. A composite material in which a first substance having septa properties and a second substance having hole transport properties are mixed The first material is preferably formed of an acceptor material having a property to accept the second material. The first substance draws electrons from the second substance, and the first substance receives an electron. electrons are generated in the second material, and holes are generated in the second material from which the electrons were extracted. The generated holes are converted into electrons by an electric field and flow to the anode 101, and the holes are transported through the hole transport layer 112 to emit light. It is implanted into layer 113 .

[0152] The first substance is a transition metal oxide or a metal oxide belonging to Groups 4 to 8 of the periodic table. Oxides, organic compounds having electron-withdrawing groups (halogen groups or cyano groups), etc. are preferred.

[0153] The transition metal oxides include oxides of metals belonging to groups 4 to 8 of the periodic table. Vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide oxide, tungsten oxide, manganese oxide, rhenium oxide, titanium oxide, ruthenium Aluminum oxide, zirconium oxide, hafnium oxide, and silver oxide have high acceptor properties. Among these, molybdenum oxide is particularly preferred because it is stable in the air, has low hygroscopicity, and is easy to handle. It is preferable because it is easy to use.

[0154] Organic compounds having the above electron-withdrawing groups (halogen groups and cyano groups) include 7,7,8,8- Tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4TCNQ), Chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12- Hexaazatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8-hexaphenyl Examples include fluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ). In particular, electron-withdrawing groups are bonded to condensed aromatic rings with multiple heteroatoms, such as HAT-CN. The compound having the above structure is thermally stable and therefore preferred.

[0155] The second substance is a substance having hole transport properties, -6 cm 2 Hole mobility above / Vs It is preferable that the second substance has the following structure: -Di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDP) PA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino ]biphenyl (abbreviation: DPAB), N,N'-bis{4-[bis(3-methylphenyl) Amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-di Amine (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl aromatic amines such as 3-[N -(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazol carbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole- 3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2 ), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino ]-9-phenylcarbazole (abbreviation: PCzPCN1), 4,4'-di(N-carbazo 1,3,5-tris[4-(N-carbazolyl)phenyl]biphenyl (abbreviation: CBP), phenyl]benzene (abbreviation: TCPB), 9-[4-(10-phenyl-9-anthryl) phenyl]-9H-carbazole (abbreviation: CzPA), 1,4-bis[4-(N-carbazole) Carbazole derivatives such as [zolyl)phenyl]-2,3,5,6-tetraphenylbenzene , 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-Bu DNA), 2-tert-butyl-9,10-di(1-naphthyl)anthracene, 9,1 0-Bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 2-ter t-Butyl-9,10-bis(4-phenylphenyl)anthracene (abbreviation: t-BuD BA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diphenyl Phenylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: :t-BuAnth), 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation DMNA), 2-tert-butyl-9,10-bis[2-(1-naphthyl)phenyl] 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2 ,3,6,7-tetramethyl-9,10-di(1-naphthyl)anthracene, 2,3,6 ,7-tetramethyl-9,10-di(2-naphthyl)anthracene, 9,9'-bianthate 10,10'-diphenyl-9,9'-bianthryl, 10,10'-bis(2- 10,10'-bis[(2,3,4,5 ,6-pentaphenyl)phenyl]-9,9'-bianthryl, anthracene, tetracene pentacene, coronene, rubrene, perylene, 2,5,8,11-tetra(tert Aromatic hydrocarbons have a vinyl skeleton. Examples of aromatic hydrocarbons having a vinyl group include 4,4'-vinyl Bis(2,2-diphenylvinyl)biphenyl (abbreviation: DPVBi), 9,10-bis[4 -(2,2-diphenylvinyl)phenyl]anthracene (abbreviation: DPVPA) In addition, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl 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-phenylamino]biphenyl( abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triflate phenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluorene -9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4'-(9 -phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1B P), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl ) triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9 -phenyl-9H-carbazol-3-yl)-triphenylamine (abbreviation: PCBAN) B), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazole- 3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethyl-N-phenyl Fluoren-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-fluoren N-phenyl-N-[4-(9-phenyl-9H -carbazol-3-yl)phenyl]-spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF), compounds with aromatic amine skeletons, such as 1,3-bis(N-carboxymethyl) mCP, 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarba 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: CzTP) Compounds with a carbazole skeleton, such as PCCP, 4,4',4''-(benzene -1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2 ,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl ]dibenzothiophene (abbreviation: DBTFLP-III), 4-[4-(9-phenyl-9 H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DB TFLP-IV), 4,4',4''-(benzene -1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), 4-{ 3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibene Using compounds with a furan skeleton such as Zofran (abbreviation: mmDBFFLBi-II) Among the above, compounds having an aromatic amine skeleton and compounds having a carbazole skeleton are preferred. The compound has good reliability and high hole transport properties, which contributes to reducing the driving voltage. This is preferable.

[0156] The hole injection layer 111 can also be formed by a wet method. PEDOT / PSS (poly(oxythiophene) / poly(styrene sulfonic acid) aqueous solution), Aniline / camphorsulfonic acid aqueous solution (PANI / CSA), PTPDES, Et-P TPDEK, or PPBA, polyaniline / poly(styrene sulfonate) (PANI / A conductive polymer compound to which an acid such as PSS has been added can be used.

[0157] The hole transport layer 112 is made of the organic compound described in the first embodiment. The hole transport layer 112 is preferably made of a plurality of layers. In this case, in order to facilitate the injection of holes, a hole injection layer is preferably formed. The HOMO level becomes deeper in a stepwise manner from the layer on the input layer 111 side to the layer on the light-emitting layer 113 side. Such a structure is preferable. The HOMO level of the material is very suitable for a deep blue fluorescent light emitting device. The organic compound described above is particularly suitable for forming a hole injection layer 111 from the hole injection layer 111 side, which is not in direct contact with the hole injection layer 111. It is suitable for use as the second or subsequent layer, and more preferably, in addition to that, It is preferable that one or more layers exist between the layer and the light-emitting layer 113. When the transport layer 112 is formed of two layers, the organic compound described in the first embodiment is included. The layer to be covered is preferably the layer located on the light-emitting layer 113 side, and when the layer is formed of three layers, , preferably the middle layer.

[0158] The hole transport layer 112 has a HOMO level that is stepped and deepened toward the light emitting layer 113. The structure of forming a plurality of layers is such that the hole injection layer 111 is formed of an organic acceptor (the above-mentioned electron-withdrawing group). When used in an element formed from an organic compound (having a halogen group or a cyano group), carrier injection Therefore, an element having excellent characteristics of good input and low driving voltage can be obtained.

[0159] The hole transport layer 112 can also be formed by a wet method. When forming, poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyl triphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-di (phenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylate Poly[N,N'-bis(4-butylphenyl)-N,N Using polymer compounds such as '-bis(phenyl)benzidine' (abbreviation: Poly-TPD), It is possible.

[0160] The light-emitting layer 113 may be a layer containing a fluorescent material, a layer containing a phosphorescent material, or a layer containing a thermally activated delayed fluorescent material ( Layers containing TADF (transparent emitting materials), layers containing quantum dots, and metal halide perovskites The layer may be a single layer or a layer containing any light-emitting material, such as a layer containing a fluorine-containing compound. The light-emitting layer may be made up of a plurality of layers. When the light-emitting layer is made up of a plurality of layers, the phosphorescent material A layer containing a phosphorescent material and a layer containing a fluorescent material may be laminated. In the layer containing the optical substance, it is preferable to use an exciplex, which will be described later.

[0161] As the fluorescent material, for example, the following materials can be used. The following fluorescent materials can also be used: 5,6-bis[4-(10-phenyl-9-anthracene] tolyl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[ 4'-(10-phenyl-9-anthryl)biphenyl-4-yl]-2,2'-bipyridine PAPP2BPy, N,N'-diphenyl-N,N'-bis[4-(9- (phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine, N,N '-Bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoro (phenyl-9-yl)pyrene-1,6-diamine (abbreviation: 1,6mMemFLPA Prn), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N '-Diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H- (10-phenyl-9-anthryl)-4'-(10-phenyl-9-anthryl)triphenylamine YGAPA (abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10- Diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9- Diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carba PCAPA, perylene, 2,5,8,11-tetra(tetrahydrofuran) rt-butyl)perylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)- 4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: P CBAPA), N,N''-(2-tert-butylanthracene-9,10-diyldi -4,1-phenylene)bis[N,N',N'-triphenyl-1,4-phenylenedia amine] (abbreviation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl [(2-(triphenyl-2-anthryl)phenyl]-9H-carbazol-3-amine (abbreviated as 2PCAP) PA), 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] Chrysene-2,7,10,15-tetraamine (abbreviation: DBC1), Coumarin 30, N- (9,10-Diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole -3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl- 2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (Abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N ',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[ 9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N '-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10 -Bis(1,1'-biphenyl-2-yl)-N-[4-(9H-carbazole-9-yl)] phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA) coumarin 545T, N,N'-diphenylquinacridone (abbreviation: DPQd), rubrene, 5,12 -Bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BPT), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl (4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2- Methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoline] Lysin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation Name: 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 ,10-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}propanedini tolyl (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7, 7-Tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolin {4H-pyran-4-ylidene}propanedinitrile (abbreviated :DCJTB), 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 -tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H -pyran-4-ylidene}propanedinitrile (abbreviation: BisDCJ™) In particular, pyrenzias such as 1,6FLPAPrn and 1,6mMemFLPAPrn Condensed aromatic diamine compounds, such as amine compounds, have high hole trapping properties and high luminescence efficiency. It is preferred because it has excellent efficiency and reliability.

[0162] In the light-emitting layer 113, materials that can be used as phosphorescent materials include, for example: Examples include: tris{2-[5-(2-methylphenyl)-4-(2 ,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN2]phenyl {Ir(mpptz-dmp)}(III) Bis(5-methyl-3,4-diphenyl-4H-1,2,4-triazolato)iridium( III) (abbreviation: [Ir(Mptz)3]), tris[4-(3-biphenyl)-5-isothiazolinone] isopropyl-3-phenyl-4H-1,2,4-triazolato]iridium(III)( Abbreviation: [Ir(iPrptz-3b)3]) Organic metal iridium complexes and tris[3-methyl-1-(2-methylphenyl)-5-phenyl] [Ir(Mpt z1‐mp)3]), tris(1‐methyl‐5‐phenyl‐3‐propyl‐1H‐1,2 ,4-triazolato)iridium(III) (abbreviation: [Ir(Prtz1-Me)3] ) and fac-tris [1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole] Ir(iPrpmi)3), tris[3-(2,6-dimethyl- (ethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium( III) (abbreviation: [Ir(dmpimpt-Me)3]) Organometallic iridium complexes and bis[2-(4',6'-difluorophenyl)pyridinium] Nat-N,C 2’ ]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation :FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium(III) picolinate (abbreviation: FIrpic), bis{2-[3',5' -bis(trifluoromethyl)phenyl]pyridinato-N,C 2’} Iridium (III ) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), bis[2‐(4', 6'-Difluorophenyl)pyridinato-N,C 2’ ]Iridium(III) acetylacetone Phenylpyridine derivatives with electron-withdrawing groups such as setonate (abbreviated as FIracac) These exhibit blue phosphorescence and are organometallic iridium complexes with iridium as a ligand. It is a compound with an emission peak between 440 nm and 520 nm.

[0163] 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-phenylpyrrolidone) 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 between 500 nm and It has an emission peak at 600 nm. In addition, organometallic iridium with a pyrimidine skeleton Complexes are particularly preferred because they are remarkably excellent in reliability and luminous efficiency.

[0164] Also, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinyl] dinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)yl Ir(5mdppm)2(dpm)], bis[4,6-di (Naphthalen-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III ) (abbreviation: [Ir(d1npm)2(dpm)]) Metal iridium complexes and (acetylacetonato)bis(2,3,5-triphenylpyrazine) Nat(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2 ,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III)( Abbreviation: [Ir(tppr)2(dpm)]), (acetylacetonato)bis[2,3-bis(acetylacetonato)bis( ... [Ir(F Organometallic iridium complexes having a pyrazine skeleton, such as dpq)2(acac)]), Tris(1-phenylisoquinolinato-N,C) 2’ ) Iridium(III) (abbreviation: [I r(piq)3]), bis(1-phenylisoquinolinato-N,C 2’ ) Iridium (I II) Pyrithiol, such as acetylacetonate (abbreviation: [Ir(piq)2(acac)]) In addition to organometallic iridium complexes with an iridinium skeleton, 2,3,7,8,12,13,17,1 8-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP) Platinum complexes such as tris(1,3-diphenyl-1,3-propanedionato) (monof (Phenanthroline) europium(III) (abbreviation: [Eu(DBM)3(Phen)]) , tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monofena (Eu(TTA)3(Phen)]) These are compounds that exhibit red phosphorescence, and It has an emission peak between 00 nm and 700 nm. The iridium complex emits red light with good chromaticity.

[0165] In addition to the phosphorescent compounds described above, various phosphorescent light-emitting materials may be selected and used. good.

[0166] TADF materials include fullerene and its derivatives, acridine and its derivatives, and eosin In addition, magnesium (Mg), zinc (Zn), cadmium (Cd) and other derivatives can be used. Cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium ( Pd) or the like can be used. For example, protoporphyrin-tin fluoride complex (SnF) shown in the following structural formula is 2(Proto IX)), mesoporphyrin-tin fluoride complex (SnF2(Meso IX), hematoporphyrin-tin fluoride complex (SnF2(Hemato IX)), Coproporphyrin tetramethyl ester-tin fluoride complex (SnF2(Copro I) II-4Me), octaethylporphyrin-tin fluoride complex (SnF2(OEP)) , etioporphyrin-tin fluoride complex (SnF2(Etio I)), octaethylporphyrin Also included is rufirin-platinum chloride complex (PtCl2OEP).

[0167] [ka]

[0168] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenyl)-4,6-bis(biphenyl-4-yl ... 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), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-3-yl] 4,6-diphenyl-1,3,5-triazine (abbreviated as '4,6-diphenyl-1,3,5-triazine- ...') Name: PCCzPTzn), 2-[4-(10H-phenoxazin-10-yl)phenyl ]-4,6-diphenyl-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-di Methyl-9H-acridin-10-yl)-9H-xanthen-9-one (Acr XTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl] Sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10'H-spiro[a π electrons of clidin-9,9'-anthracen]-10'-one (abbreviation: ACRSA), etc. Heterocyclic compounds having both π-electron-rich and π-electron-deficient heteroaromatic rings can also be used. The heterocyclic compound has a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring. Therefore, both the electron transport property and the hole transport property are high, which is preferable. A substance in which a ring and a π-electron-deficient heteroaromatic ring are directly bonded is a donor for the π-electron-rich heteroaromatic ring. The acceptor property of the π-electron-deficient heteroaromatic ring is also strengthened, and the energies of the S1 and T1 levels are increased. This is particularly preferred because the energy difference between the two is small, allowing efficient thermally activated delayed fluorescence. In addition, electron-withdrawing groups such as cyano groups are bonded instead of the π-electron-deficient heteroaromatic ring. An aromatic ring may also be used.

[0169] [ka]

[0170] In addition, quantum dots include group 14 elements, group 15 elements, group 16 elements, and multiple group 14 elements. Compounds consisting of elements from groups 4 to 14 and elements from group 16, Compounds of Group 2 elements and Group 16 elements, compounds of Group 13 elements and Group 15 elements, compounds of Group 13 elements Compounds of Group 17 elements, Compounds of Group 14 elements and Group 15 elements, Compounds of Group 11 elements Compounds of group 17 elements, iron oxides, titanium oxides, chalcogenide spinels, various Examples include nano-sized particles such as semiconductor clusters and metal halide perovskites. can.

[0171] Specifically, cadmium selenide (CdSe), cadmium sulfide (CdS), and cadmium telluride Cadmium (CdTe), zinc selenide (ZnSe), zinc oxide (ZnO), zinc sulfide ( ZnS), zinc telluride (ZnTe), mercury sulfide (HgS), mercury selenide (HgSe) , mercury telluride (HgTe), indium arsenide (InAs), indium phosphide (InP ), gallium arsenide (GaAs), gallium phosphide (GaP), indium nitride (InN) , gallium nitride (GaN), indium antimonide (InSb), gallium antimonide GaSb, aluminum phosphide (AlP), aluminum arsenide (AlAs), Aluminum sulphide (AlSb), lead(II) selenide (PbSe), lead(II) telluride (I I) (PbTe), lead(II) sulfide (PbS), indium selenide (In2Se3), Indium telluride (In2Te3), indium sulfide (In2S3), gallium selenide Arsenic(III) sulfide (Ga2Se3), arsenic(III) selenide (As2S3), arsenic(III) selenide (A s2Se3), arsenic(III) telluride (As2Te3), antimony(III) sulfide ( Sb2S3), antimony selenide(III) (Sb2Se3), antimony telluride ( III) (Sb2Te3), bismuth(III) sulfide (Bi2S3), bismuth selenide (III) (Bi2Se3), bismuth telluride (III) (Bi2Te3), silicon ( Si), silicon carbide (SiC), germanium (Ge), tin (Sn), selenium (Se), Tellurium (Te), Boron (B), Carbon (C), Phosphorus (P), Boron Nitride (BN), Phosphide Boron (BP), boron arsenide (BAs), aluminum nitride (AlN), aluminum sulfide Al2S3, barium sulfide (BaS), barium selenide (BaSe), telluride Barium (BaTe), calcium sulfide (CaS), calcium selenide (CaSe), Calcium telluride (CaTe), beryllium sulfide (BeS), beryllium selenide (B eSe), beryllium telluride (BeTe), magnesium sulfide (MgS), magnesium selenide Magnesium (MgSe), Germanium sulfide (GeS), Germanium selenide (GeS e), germanium telluride (GeTe), tin(IV) sulfide (SnS2), tin(II) sulfide ) (SnS), tin(II) selenide (SnSe), tin(II) telluride (SnTe), acid Lead(II) chloride (PbO), copper(I) fluoride (CuF), copper(I) chloride (CuCl), copper bromide Copper(I) (CuBr), copper(I) iodide (CuI), copper(I) oxide (CuO), selenium Copper(I) oxide (CuSe), nickel(II) oxide (NiO), cobalt(II) oxide ( CoO), cobalt(II) sulfide (CoS), iron tetroxide (Fe3O4), iron sulfide (II ) (FeS), manganese(II) oxide (MnO), molybdenum(IV) sulfide (MoS2) , vanadium(II) oxide (VO), vanadium(IV) oxide (VO2), tungsten oxide Tantalum(IV) oxide (WO2), tantalum(V) oxide (Ta2O5), titanium oxide (TiO2, Ti2O5, Ti2O3, Ti5O9, etc.), zirconium oxide (ZrO2), silicon nitride Silicon (Si3N4), germanium nitride (Ge3N4), aluminum oxide (Al2O3) , barium titanate (BaTiO3), selenium, zinc and cadmium compounds (CdZnS e), compounds of indium, arsenic and phosphorus (InAsP), compounds of cadmium, selenium and sulfur Compounds of cadmium, selenium and tellurium (CdSeS), compounds of cadmium, selenium and tellurium (CdSeTe), indium Indium, gallium and arsenic compounds (InGaAs), indium, gallium and selenium compounds (InGaSe), indium selenium and sulfur compound (InSeS), copper and indium and sulfur compounds (e.g., CuInS2), and combinations thereof. However, the present invention is not limited to these. In addition, the composition may be expressed in any ratio, that is, the so-called alloy type quantum dots. For example, CdS x Se 1-x (x is any number between 0 and 1) The alloy quantum dots can change the emission wavelength by changing the ratio of x. This is one of the effective means for obtaining blue light emission.

[0172] Quantum dot structures include core type, core-shell type, and core-multishell type. Either of these can be used, but it is also possible to cover the core with another inorganic compound with a wider band gap. By forming a shell of material, defects and dangling bonds on the nanocrystal surface can be eliminated. This significantly improves the quantum efficiency of light emission, It is preferable to use core-shell or core-multishell quantum dots. Examples of the material include zinc sulfide (ZnS) and zinc oxide (ZnO).

[0173] In addition, quantum dots have a high proportion of surface atoms, making them highly reactive and prone to aggregation. Therefore, a protective agent or a protective group is attached to the surface of the quantum dots. It is preferable that the protecting agent is attached or the protecting group is provided. It can prevent aggregation and increase solubility in solvents. It can also reduce reactivity and improve electrical conductivity. It is also possible to improve stability. Examples of protecting agents (or protecting groups) include polio Polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene Polyoxyethylene alkyl ethers such as ethylene oleyl ether, tripropyl phosphite phosphine, tributylphosphine, trihexylphosphine, trioctylphosphine, etc. Trialkylphosphines, polyoxyethylene n-octylphenyl ether, polyoxyethylene Polyoxyethylene alkylphenyl ethers such as oxyethylene n-nonylphenyl ether esters, tri(n-hexyl)amine, tri(n-octyl)amine, tri(n-decyl)amine ) Tertiary amines such as amine, tripropylphosphine oxide, tributylphosphine oxide, trihexylphosphine oxide, trioctylphosphine oxide, tridecylphosphine oxide Organic phosphorus compounds such as silylphosphine oxide, polyethylene glycol dilaurate, polyethylene glycol diesters such as polyethylene glycol distearate, Organic nitrogen compounds such as nitrogen-containing aromatic compounds such as pyridine, lutidine, collidine, and quinolines , hexylamine, octylamine, decylamine, dodecylamine, tetradecylamine aminoalkanes such as dibutylsulfite, hexadecylamine, and octadecylamine; dialkyl sulfides such as dimethyl sulfoxide and dibutyl sulfoxide; organic sulfur compounds such as alkyl sulfoxides, sulfur-containing aromatic compounds such as thiophene, palmitoyl Higher fatty acids such as acetic acid, stearic acid, and oleic acid, alcohols, sorbitan fatty acid esters esters, fatty acid modified polyesters, tertiary amine modified polyurethanes, polyethylene terephthalate Examples include amines.

[0174] The quantum dot may be a rod-shaped quantum rod. By using quantum rods as a light-emitting material, it is possible to obtain light with a good directivity. As a result, a light emitting device with good external quantum efficiency can be obtained.

[0175] In addition, when forming a light-emitting layer in which the quantum dots are dispersed in a host as a light-emitting material, The quantum dots are dispersed in a host material, or the host material and quantum dots are dissolved in an appropriate liquid medium. It is dissolved or dispersed and then applied to wet processes (spin coating, casting, die coating, Blade coating method, roll coating method, inkjet method, printing method, spray coating method, car After forming a layer using a method such as the Tencoat method or the Langmuir-Blodgett method, the solvent is removed. Alternatively, the layer may be formed by baking.

[0176] Examples of liquid media used in wet processes include methyl ethyl ketone, cyclohexane, and the like. Ketones such as xanone, fatty acid esters such as ethyl acetate, halogens such as dichlorobenzene aromatic hydrocarbons, toluene, xylene, mesitylene, cyclohexylbenzene, etc. Hydrocarbons, aliphatic hydrocarbons such as cyclohexane, decalin, and dodecane, dimethylformamide Organic solvents such as dimethyl amide (DMF) and dimethyl sulfoxide (DMSO) can be used. Cut.

[0177] When a fluorescent substance is used as the host material for the light-emitting layer, 9-phenyl-3-[4 -(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCz PA), 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: cgDBCzPA), 6 -[3-(9,10-diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[ 1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-{4-(9-furan {phenyl-9H-fluoren-9-yl)-biphenyl-4'-yl}anthracene (abbreviation Materials having an anthracene skeleton, such as PEG-1000 (FLPPA), are suitable. When a substance that emits fluorescent light is used as a host material for the fluorescent material, it is possible to obtain a light emitting material that has good luminous efficiency and durability. In particular, CzPA, cgDBCzPA, 2mBnfPPA , PCzPA is a preferred choice as it exhibits very good properties.

[0178] When a material other than the above-mentioned materials is used as the host material, a material having an electron transporting property or a hole transporting property is used. Various carrier transport materials can be used, including materials having a carrier transporting property.

[0179] Examples of materials with electron transport properties include bis(10-hydroxybenzo[h]quinolinol). Nato)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, (aryl)-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-Cyclohexyl-3-yldibenzo[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: TmP Among the above, heterocyclic compounds having a pyridine skeleton such as diazonium phosphate (PPB) are also suitable. Heterocyclic compounds with an amine skeleton and heterocyclic compounds with a pyridine skeleton have good reliability. In particular, heterocyclic compounds having a diazine (pyrimidine or pyrazine) skeleton are preferred. It has high electron transport properties and also contributes to reducing the driving voltage.

[0180] As a material with hole transport properties, 4,4'-bis[N-(1-naphthyl)-N-phenylene] 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 amino]biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluorene) 4-phenyl-3'-(9-yl)triphenylamine (abbreviation: BPAFLP), -phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4- Phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-ca PCBBi1BP, 4-(1-naphthyl)triphenylamine (butyl)-4'-(9-phenyl-9H-carbazol-3-yl)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'-bifluorene Compounds with aromatic amine skeletons such as PCBASF (abbreviated as PCBASF) and 1, 3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)benzene 3,6-bis(3,5-diphenylphenyl)-9 -phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl-9H-carbazole) Compounds with a carbazole skeleton, such as PCCP (carbazole derivatives), and 4,4', 4''-(Benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DB T3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene- 9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), 4-[4- (9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothio phen (abbreviation: DBTFLP-IV) and other compounds with a thiophene skeleton, such as 4,4' ,4''-(Benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF 3P-II), 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl furan skeleton such as [phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II) Among the above, compounds having an aromatic amine skeleton and compounds having a carbamate skeleton are particularly preferred. Compounds having a zole skeleton have good reliability, high hole transport properties, and low driving voltage. In addition to the hole transport materials described above, Therefore, a hole transport material may be used.

[0181] When a fluorescent substance is used as the luminescent substance, 9-phenyl-3-[4-(10-phenyl 3-[(9-(anthryl)phenyl)phenyl]-9H-carbazole (abbreviation: PCzPA), 4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCP N), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazo CzPA, 7-[4-(10-phenyl-9-anthryl)phenyl]- 7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9, 10-diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan Ran (abbreviation: 2mBnfPPA), 9-phenyl-10-{4-(9-phenyl-9H- Fluoren-9-yl)-biphenyl-4'-yl}-anthracene (abbreviation: FLPPA A material having an anthracene skeleton such as When used as a host material for a light-emitting substance, it can realize an emitting layer with good luminous efficiency and durability. In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA is a preferred choice as it exhibits very good properties.

[0182] The host material may be a mixture of a plurality of substances. When using a material having electron transport properties, a material having hole transport properties is mixed. It is preferable to mix a material having an electron transporting property with a material having a hole transporting 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 transporting properties to the content of the material having electron transporting properties can be The ratio of the material having transport properties to the material having electron transport properties may be 1:9 to 9:1.

[0183] Furthermore, these mixed host materials may form an exciplex. , the wavelength of the lowest energy absorption band of fluorescent materials, phosphorescent materials, and TADF materials By selecting a combination that forms an exciplex that emits light that overlaps with the This allows for smooth energy transfer and efficient light emission. This is a preferable configuration because the driving voltage is also reduced.

[0184] The light-emitting layer 113 having the above-described structure can be formed by co-evaporation using a vacuum evaporation method or by forming a mixed solution. , gravure printing, offset printing, inkjet printing, spin coating and dip coating It can be prepared by using a coating method or the like.

[0185] The electron transport layer 114 is a layer containing a substance having an electron transport property. As the material, the materials having electron transport properties that can be used as the host material are listed. A material having an anthracene skeleton or a material having an anthracene skeleton can be used.

[0186] Furthermore, a layer for controlling the movement of electron carriers may be provided between the electron transport layer and the light emitting layer. This is achieved by adding a small amount of a substance with high electron trapping properties to a material with high electron transport properties as described above. It is a layer that adjusts the carrier balance by suppressing the movement of electron carriers. This type of structure prevents electrons from penetrating the light-emitting layer. This is highly effective in suppressing problems that arise (for example, a reduction in the device life).

[0187] In addition, an electron injection layer 115 is formed between the electron transport layer 114 and the cathode 102 and in contact with the cathode 102. The electron injection layer 115 may be formed using a material such as lithium fluoride (LiF), cesium fluoride, or the like. Alkali metals or alkaline earths such as calcium fluoride (CsF), calcium fluoride (CaF2), etc. For example, a metal or a compound thereof can be used. The layer containing alkali metals or alkaline earth metals or their compounds is used. Alternatively, the electron injection layer 115 may be made of an electride. For example, a mixed oxide of calcium and aluminum with high electron concentration is used as the oxide. The electron-injecting layer 115 may be formed of a substance having an electron-transporting property. By using a layer containing an alkali metal or alkaline earth metal, the cathode 1 This is more preferable because electron injection from O2 is carried out efficiently.

[0188] In addition, a charge generation layer 116 may be provided instead of the electron injection layer 115 (FIG. 1B). When a potential is applied to the charge generating layer 116, holes are generated in the layer in contact with the cathode side of the layer, and cations are generated in the layer in contact with the cathode side of the layer. The charge generation layer 116 is a layer that can inject electrons into the layer that is in contact with the electrode side. At least a P-type layer 117 is included. The P-type layer 117 constitutes the hole injection layer 111 described above. It is preferable to form the P-type layer using the composite material mentioned above as a material that can be used. 117 is a composite material comprising a film containing the above-mentioned acceptor material and a hole transport By applying a potential to the P-type layer 117, Electrons are injected into the electron transport layer 114 and holes are injected into the cathode 102, and the light-emitting device operates. The organic compound of one embodiment of the present invention is added to the electron-transporting layer 114 at a position in contact with the charge-generation layer 116. The presence of the layer containing the compound suppresses a decrease in luminance due to accumulation of driving time of the light-emitting element, A light emitting element with a long life can be obtained.

[0189] The charge generation layer 116 includes an electron relay layer 118 and an electron injection buffer layer in addition to the P-type layer 117. It is preferable that one or both of the layers 119 be provided.

[0190] 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 1 is between the LUMO level of the material contained in the layer adjacent to the electron-relay layer 1. Specific energy levels of the LUMO levels in electron transport materials used in 18 The potential is -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 of the formula (I) or metal complexes having a metal-oxygen bond and an aromatic ligand.

[0191] The electron injection buffer layer 119 contains an alkali metal, an alkaline earth metal, a rare earth metal, and and their compounds (alkali metal compounds (oxides such as lithium oxide, halides, carbonates) Alkaline earth metal compounds (including carbonates such as lithium and cesium carbonate), oxides, halides compounds of rare earth metals (including oxides, halides, carbonates) or rare earth metal compounds (including oxides, halides, carbonates) It is possible to use a substance with high electron injection properties, such as tetrahydrofuran (Tetrahydrofuran) and tetrahydrofuran (Tetrahydrofuran).

[0192] The electron injection buffer layer 119 contains a substance having an electron transporting property and a donor substance. When formed, the donor material is an alkali metal, an alkaline earth metal, or a rare earth metal. metals and their compounds (alkali metal compounds (oxides such as lithium oxide, halides compounds, carbonates such as lithium carbonate and cesium carbonate), alkaline earth metal compounds (oxides , halides, carbonates) or compounds of rare earth metals (oxides, halides, In addition to carbonates), tetrathianaphthacene (abbreviated as TTN), nickelocene, decametacene, An organic compound such as thirnickelocene can also be used. The electron transport layer 114 is formed using the same material as that of the electron transport layer 114 described above. It is possible.

[0193] The material forming the cathode 102 has a small work function (specifically, 3.8 eV or less). Metals, alloys, electrically conductive compounds, and mixtures thereof can be used. Specific examples of such cathode materials include alkaline metals such as lithium (Li) and cesium (Cs). element, such as magnesium (Mg), calcium (Ca), and strontium (Sr) Elements belonging to Group 1 or 2 of the periodic table, and alloys containing these elements (MgAg, Al rare earth metals such as Li, europium (Eu), ytterbium (Yb) and However, an electron injection layer may be provided between the cathode 102 and the electron transport layer. By providing the above, regardless of the magnitude of the work function, Al, Ag, ITO, silicon or Various conductive materials such as silicon oxide-containing indium oxide-tin oxide are used as the cathode 102. These conductive materials can be deposited by dry methods such as vacuum deposition and sputtering. The film can be formed by using an ink jet method, a spin coating method, or the like. - It may be formed by a wet method using a gel method, or by a wet method using a paste of a metal material. You may do so.

[0194] The EL layer 103 can be formed by various methods, including dry and wet methods. For example, vacuum deposition and wet process methods (spin coating, casting, die coating) can be used. Coating method, blade coating method, roll coating method, inkjet method, printing method (gravure printing) printing, offset printing, screen printing, etc.), spray coating, curtain coating , Langmuir-Blodgett method, etc.) may also be used.

[0195] Furthermore, the above-mentioned electrodes or layers may be formed using different film formation methods.

[0196] Here, a method for forming the layer 786 containing a light-emitting substance by a droplet discharge method will be described with reference to FIG. 2A to 2D illustrate a method for manufacturing the layer 786 containing a light-emitting material. FIG.

[0197] First, a conductive film 772 is formed over a planarization insulating film 770. The insulating film 730 is formed as shown in FIG. 2(A).

[0198] Next, a droplet is discharged from a droplet discharge device 783 to an exposed portion of the conductive film 772, which is an opening in the insulating film 730. Droplets 784 are ejected to form a layer 785 containing the composition. The droplets 784 contain the composition including the solvent. and is attached onto the conductive film 772 (see FIG. 2B).

[0199] The step of discharging the droplets 784 may be performed under reduced pressure.

[0200] Next, the solvent is removed from the layer 785 containing the composition, and the layer is solidified to form a layer containing a luminescent material. A layer 786 is formed (see FIG. 2C).

[0201] The solvent may be removed by a drying step or a heating step.

[0202] Next, a conductive film 788 is formed over the layer 786 containing a light-emitting material to form a light-emitting element 782. (See Figure 2(D)).

[0203] In this way, when the layer 786 containing the light-emitting material is formed by the droplet discharge method, the composition is selectively discharged. This reduces material loss. Since no lithography process is required, the process can be simplified and costs can be reduced. Cut.

[0204] The droplet discharge method described above is a method of discharging a composition using a nozzle having a discharge port, or one or more is a general term for anything that has a means for ejecting droplets, such as a head having multiple nozzles.

[0205] Next, a droplet discharge device used in the droplet discharge method will be described with reference to FIG. FIG. 14 is a conceptual diagram illustrating a droplet ejection device 1400.

[0206] The droplet discharge device 1400 has a droplet discharge means 1403. 3 has a head 1405, a head 1412, and a head 1416.

[0207] The head 1405 and the head 1412 are connected to a control means 1407, which controls the computer. By controlling the image forming apparatus 1410, it is possible to draw a pattern in a pre-programmed manner. can.

[0208] The timing of drawing may be, for example, the timing of the marker 1 formed on the substrate 1402. Alternatively, the reference point may be determined based on the outer edge of the substrate 1402. Here, the marker 1411 is detected by the imaging means 1404, and the image processing means 1 The signal converted into a digital signal by 409 is recognized by a computer 1410 and a control signal is generated. The generated signal is sent to the control means 1407.

[0209] The imaging means 1404 may be a charge coupled device (CCD) or a complementary metal oxide semiconductor ( An image sensor using a CMOS (Complementary Metal Oxide Semiconductor) can be used. The information of the pattern to be formed is stored in the storage medium 1408. Based on this, a control signal is sent to the control means 1407, and the individual heads 1 of the droplet discharging means 1403 are controlled. The heads 405, 1412, and 1416 can be controlled individually. The material is supplied from the material supply source 1413, the material supply source 1414, and the material supply source 1415 through piping. The heads 1405, 1412, and 1416 are supplied with the ink.

[0210] The inside of head 1405, head 1412, and head 1416 is as shown by the dotted line 1406. The structure has a space for filling the liquid material and a nozzle that is a discharge outlet. Although the head 1412 does not have the same internal structure as the head 1405, By providing nozzles of different sizes on the head 1412, different materials can be drawn at different widths simultaneously. It is possible to use one head to eject multiple types of luminescent materials and create images. When drawing on a wide area, multiple nozzles can be used to improve throughput. The same material can be ejected simultaneously to create a pattern. , head 1412 and head 1416 move on the substrate in the directions of the X, Y, and Z arrows shown in FIG. It is possible to freely scan and set the area to be drawn, and the same pattern can be printed on one board. Multiple drawings can be made.

[0211] The step of discharging the composition may be carried out under reduced pressure. After the composition is discharged, one or both of the steps of drying and baking are carried out. Both processes involve heat treatment, but the purpose, temperature and time are different. The drying and firing processes are carried out under normal or reduced pressure by laser light irradiation, instantaneous thermal annealing, or heating. The timing and number of times of this heat treatment are not particularly limited. In order to perform the drying and baking processes well, the temperature at that time should be adjusted depending on the material and composition of the substrate. It depends on the nature of the composition.

[0212] As described above, the layer 786 containing a light-emitting substance can be manufactured using a droplet discharge apparatus. .

[0213] When the layer 786 containing a light-emitting material is manufactured using a droplet discharge apparatus, various organic materials and Organic-inorganic halogen perovskites are dissolved or dispersed in a solvent and then used in a wet process. When forming the coating layer from the above, various organic solvents can be used to prepare a coating composition. The organic solvents that can be used for this purpose are benzene, toluene, xylene, and mesitylene. , tetrahydrofuran, dioxane, ethanol, methanol, n-propanol, isopropanol Propanol, n-butanol, t-butanol, acetonitrile, dimethyl sulfoxide dimethylformamide, chloroform, methylene chloride, carbon tetrachloride, ethyl acetate Various organic solvents such as benzene, hexane, and cyclohexane can be used. By using a low polarity benzene derivative such as toluene, xylene, or mesitylene, a suitable It is possible to create a solution of a certain concentration, and the materials contained in the ink will deteriorate due to oxidation, etc. In addition, it is preferable to prevent the uniformity of the film after fabrication and the uniformity of the film thickness. The boiling point of the solvent is preferably 100°C or higher, and toluene, xylene, and mesitylene are further preferred. preferable.

[0214] The above configuration may be appropriately combined with other embodiments or other configurations in this embodiment. It is possible to do this.

[0215] Next, the embodiment of a light-emitting element (also called a stacked element) having a configuration in which a plurality of light-emitting units are stacked This light-emitting element has a plurality of electrodes between an anode and a cathode. The light-emitting element has a light-emitting unit E shown in FIG. It has the same structure as the L layer 103. That is, it is the same as the light-emitting element shown in FIG. is a light-emitting element having one light-emitting unit, and the light-emitting element shown in FIG. 1(C) has a plurality of light-emitting elements. It can be said to be a light-emitting element having a light-emitting unit.

[0216] In FIG. 1C, a first light-emitting unit is disposed between the first electrode 501 and the second electrode 502. The knit 511 and the second light-emitting unit 512 are stacked, and the first light-emitting unit 511 A charge generating layer 513 is provided between the first electrode and the second light-emitting unit 512. The first electrode 501 and the second electrode 502 correspond to the anode 101 and the cathode 102 in FIG. 1(A), respectively. However, the same as that described in the explanation of FIG. 1(A) can be applied. The light unit 511 and the second light emitting unit 512 may have the same configuration or different configurations. Good too.

[0217] When a voltage is applied between the first electrode 501 and the second electrode 502, the charge generating layer 513 generates a It has the function of injecting electrons into one light-emitting unit and holes into the other light-emitting unit. That is, in FIG. 1C, the potential of the first electrode is higher than the potential of the second electrode. When a voltage is applied so that the charge generation layer 513 generates electrons in the first light-emitting unit 511, The light emitting element 512 may be any element that injects positive electrons into the first light emitting unit 512 and injects positive holes into the second light emitting unit 512.

[0218] The charge generation layer 513 is formed to have the same structure as the charge generation layer 116 described in FIG. 1(B). The composite material of an organic compound and a metal oxide has the properties of carrier injection and carrier transport. Because of its excellent transmission properties, it can be driven at low voltage and low current. When the anode side of the unit is in contact with the charge generating layer 513, the charge generating layer 513 becomes a light emitting unit. Since it can also function as a hole injection layer for the unit, the light-emitting unit does not need to have a hole injection layer. It's also good.

[0219] In addition, when the electron injection buffer layer 119 is provided in the charge generation layer 513, the layer Since it plays the role of an electron injection layer in the light-emitting unit, it is not necessarily superimposed on the light-emitting unit. There is no need to form an electron injection layer.

[0220] Although the light emitting element having two light emitting units has been described in FIG. 1C, the light emitting element having three or more light emitting units may be The present invention can be similarly applied to a light-emitting device in which the light-emitting units are stacked. As in the light-emitting device according to the embodiment, a plurality of light-emitting units are disposed between a pair of electrodes, and a charge generating layer 51 By separating the LEDs into three sections, high brightness light emission is possible while keeping the current density low. Furthermore, it is possible to realize a light-emitting device that can be driven at a low voltage and consumes little power. It is possible.

[0221] In addition, by making the light-emitting color of each light-emitting unit different, the light-emitting element as a whole Thus, light of a desired color can be obtained.

[0222] (Embodiment 3) In this embodiment, a light-emitting device using the light-emitting element described in Embodiment 1 will be described. .

[0223] A light-emitting device according to one embodiment of the present invention will be described with reference to FIG. 4. Note that FIG. 4A shows a light-emitting device. 4(B) is a cross-sectional view of FIG. 4(A) taken along lines A-B and C-D. This light emitting device includes a driving circuit section shown by the dotted line that controls the light emission of the light emitting elements. (source line driving circuit) 601, pixel section 602, driving circuit section (gate line driving circuit) 603 Also, 604 is a sealing substrate, and 605 is a sealing material. The inside of the hole is a space 607.

[0224] 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 the input signal, and the FPC (flexible printed circuit board) is the external input terminal. Video signal, clock signal, start signal, reset signal from Lint Circuit 609 Although only the FPC is shown here, this FPC has a printed circuit board. A printed wiring board (PWB) may be attached. This includes not only the device itself but also the state in which an FPC or PWB is attached to it. do.

[0225] Next, the cross-sectional structure will be described with reference to FIG. A source line driver circuit 601, which is a driver circuit portion, is formed in this example. , one pixel in the pixel section 602 is shown.

[0226] The source line driver circuit 601 includes an n-channel FET 623 and a p-channel FET 62 4 is combined to form a CMOS circuit. In addition, the drive circuit is a CMOS circuit Alternatively, the substrate may be formed of a PMOS circuit or an NMOS circuit. Although the driver integrated type with the drive circuit formed on the top is shown, this is not necessarily required. It may also be formed externally rather than on the substrate.

[0227] The pixel section 602 includes a switching FET 611, a current control FET 612, and 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 be used. Good too.

[0228] There are no particular restrictions on the type and crystallinity of the semiconductor used in the FET, and amorphous semiconductors are used. Examples of semiconductors used in FETs include the first Group 3 semiconductors, Group 14 semiconductors, compound semiconductors, oxide semiconductors, and organic semiconductor materials are used. However, it is particularly preferable to use an oxide semiconductor. For example, In-Ga oxide, In-M-Zn oxide (M is Al, Ga, Y, Zr, La, C e, or Nd). In addition, the energy gap is 2 eV or more, and preferably By using an oxide semiconductor material with a conductivity of 2.5 eV or more, more preferably 3 eV or more, This is a preferable configuration because it can reduce the off-state current of the transistor.

[0229] An insulator 614 is formed to cover the end of the first electrode 613. It can be formed by using a di-type photosensitive acrylic resin film.

[0230] In order to improve the covering property, the upper end or the lower end of the insulator 614 is provided with a curvature. For example, the material of the insulator 614 is a positive photosensitive adhesive. When using krill, the radius of curvature (0.2 μm to 3 μm) is set only at the top end of the insulator 614. It is preferable to provide a curved surface having a curved surface. Alternatively, a positive photosensitive resin can be used.

[0231] An EL layer 616 and a second electrode 617 are formed on the first electrode 613. These correspond to the anode 101, the EL layer 103, and the cathode 104 described with reference to FIGS. 1(A) and 1(B), respectively. 1(C) or the first electrode 501, the EL layer 503, and the second electrode 502 Equivalent.

[0232] The EL layer 616 preferably includes an organometallic complex. It is preferably used as a luminescent center substance in the layer.

[0233] Furthermore, by bonding the sealing substrate 604 to the element substrate 610 with a sealing material 605, A space 607 surrounded by an element substrate 610, a sealing substrate 604, and a sealing material 605 contains a light-emitting element. The space 607 is filled with a filler. In addition to being filled with an inert gas (nitrogen, argon, etc.), it is also possible to fill it with a sealing material 605. If a recess is formed in the sealing substrate and a desiccant is placed there, deterioration due to the influence of moisture can be prevented. This is a preferable configuration because it can suppress the degradation.

[0234] 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 substrate 610 and the sealing substrate 604 include glass substrates, quartz substrates, and FRP ( Fiber Reinforced Plastics), PVF (Polyvinyl Fluoride) A plastic substrate made of, for example, polyester or acrylic can be used.

[0235] For example, in this specification and the like, transistors and light-emitting elements are formed using various substrates. The type of substrate is not limited to a specific one. An example of the substrate is as follows: Examples include semiconductor substrates (such as single crystal substrates or silicon substrates), SOI substrates, glass substrates, Quartz substrate, plastic substrate, metal substrate, stainless steel substrate, stainless steel Substrate with foil, tungsten substrate, substrate with tungsten foil, flexible These include substrates, laminated films, papers containing fibrous materials, or base films. Examples of the glass substrate include barium borosilicate glass, aluminoborosilicate glass, or silicon dioxide. Examples include glass-lime glass. Flexible substrates, laminated films, and base films. Examples include: polyethylene terephthalate (PET) , polyethylene naphthalate (PEN), and polyethersulfone (PES). For example, there are plastics such as acrylic resins. Examples of such materials include polytetrafluoroethylene (PTFE), polypropylene, and polyethylene. Examples include sterol, polyvinyl fluoride, or polyvinyl chloride. Examples of the material include polyamide, polyimide, aramid, epoxy, inorganic vapor deposition film, and paper. In particular, transistors are manufactured using semiconductor substrates, single crystal substrates, SOI substrates, etc. This results in less variation in characteristics, size, or shape, a high current capacity, and a small size. It is possible to manufacture transistors with small capacitance. This configuration makes it possible to reduce the power consumption of the circuit or to increase the integration density of the circuit.

[0236] In addition, a flexible substrate is used as the substrate, and transistors and light-emitting elements are directly formed on the flexible substrate. Alternatively, a peeling layer may be formed between the substrate and the transistor or between the substrate and the light-emitting element. The release layer may be provided to separate the semiconductor device from the substrate after the semiconductor device is partially or entirely completed thereon. The transistor can be separated and transferred to another substrate. The transfer can be performed on a substrate having poor mechanical strength or a flexible substrate. The laminated structure of inorganic films such as stainless steel and silicon oxide films, and the organic film such as polyimide on the substrate A configuration in which a resin film is formed, etc., can be used.

[0237] That is, a transistor or a light-emitting element is formed on a certain substrate, and then the transistor or light-emitting element is formed on another substrate. The transistors and light-emitting elements may be transposed and disposed on different substrates. An example of a substrate onto which a transistor or a light emitting element is transferred is a substrate on which the above-mentioned transistor is formed. In addition to the substrates that can be used, paper substrates, cellophane substrates, aramid film substrates, polyimide substrates, Hard film substrate, stone substrate, wood substrate, fabric substrate (natural fiber (silk, cotton, linen), synthetic fiber (nano) Iron, polyurethane, polyester) or regenerated fiber (acetate, cupro, These include recycled polyester, leather substrates, and rubber substrates. By using a substrate, it is possible to form transistors with good characteristics and low power consumption. It is possible to form a thin film, to make a device that is durable, heat resistant, lightweight, or thin. do.

[0238] In FIG. 5, a light emitting element that emits white light is formed, and a colored layer (color filter) or the like is provided. FIG. 5(A) shows an example of a full-color light-emitting device. an insulating film 1002, a gate insulating film 1003, gate electrodes 1006, 1007, 1008, a first the first interlayer insulating film 1020, the second interlayer insulating film 1021, the peripheral portion 1042, the pixel portion 1040, The driving circuit unit 1041, the first electrodes 1024W, 1024R, 1024G, 10 24B, a partition wall 1025, an EL layer 1028, a cathode 1029 of the light-emitting element, a sealing substrate 1031, A seal material 1032 and the like are shown.

[0239] In addition, in FIG. 5(A), the colored layers (red colored layer 1034R, green colored layer 1034G, blue The colored layer 1034B is provided on the transparent substrate 1033. A transparent substrate on which a colored layer and a black layer are provided may be further provided. 1033 is aligned and fixed to the substrate 1001. The colored layer and the black layer are In FIG. 5(A), the colored layer is covered with an overcoat layer 1036. There are light-emitting layers that emit light to the outside without passing through the color layers of each color, and light-emitting layers that emit light to the outside. The light that does not pass through the colored layer is white, and the light that passes through the colored layer is red, blue, and green. Images can be expressed using pixels.

[0240] In FIG. 5(B), the colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer A color layer 1034B) is formed between the gate insulating film 1003 and the first interlayer insulating film 1020. In this way, the colored layer is provided between the substrate 1001 and the sealing substrate 1031. That's fine.

[0241] In the light emitting device described above, light is taken in from the substrate 1001 side on which the FET is formed. The light emitting device has a bottom emission structure, but the light is emitted from the sealing substrate 1031 side. It may also be a light emitting device with a structure where light is extracted (top emission type). A cross-sectional view of the light-emitting device is shown in FIG. 6. In this case, a substrate 1001 that does not transmit light is used. Until the connection electrode that connects the FET and the anode of the light-emitting element is fabricated, The third interlayer insulating film 1037 is then formed in the same manner as in the case of an emission type light emitting device. The insulating film 1022 is formed to cover the insulating film 1022. This insulating film may also have a role of planarization. The insulating film 1037 is formed using the same material as the second interlayer insulating film, as well as various other materials. It is possible.

[0242] The first electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting element are positive electrodes. The cathode is also used as the top-emission type light-emitting diode, as shown in Figure 6. In the case of a device, it is preferable that the first electrode is a reflective electrode. As explained as the EL layer 103 in FIG. 1(A) and (B) or the EL layer 503 in FIG. 1(C), The device has a structure that allows white light emission.

[0243] In the top emission structure shown in Figure 6, the colored layers (red colored layer 1034R, green The sealing is performed using a sealing substrate 1031 provided with a colored layer 1034G and a blue colored layer 1034B. The sealing substrate 1031 has a black layer (black A coloring layer (a red coloring layer 1034R, a green coloring layer 1035R) may be provided. The blue colored layer 1034G and the black layer 1034B are covered with an overcoat layer. Note that the sealing substrate 1031 is a light-transmitting substrate.

[0244] Although an example of full-color display using four colors, red, green, blue, and white, is shown here, the present invention is not particularly limited to this. Alternatively, a full color display may be performed using three colors of red, green, and blue, or four colors of red, green, blue, and yellow.

[0245] FIG. 7 shows a passive matrix light-emitting device according to one embodiment of the present invention. FIG. 7(A) is a perspective view showing a light emitting device, and FIG. 7(B) is a cross-sectional view taken along XY in FIG. 7(A). In FIG. 7, an EL layer 955 is disposed between an electrode 952 and an electrode 956 on a substrate 951. The end of the electrode 952 is covered with an insulating layer 953. A partition layer 954 is provided on the substrate 53. The sidewalls of the partition layer 954 are Accordingly, the distance between one side wall and the other side wall is inclined to become narrower. The cross section of the partition layer 954 in the short side direction is trapezoidal, and the bottom side (similar to the surface direction of the insulating layer 953) The side in contact with the insulating layer 953 is oriented in the same direction as the surface direction of the insulating layer 953. The side of the partition wall layer 954 facing in the direction of the insulating layer 953 is shorter than the side of the partition wall layer 954 that is not in contact with the insulating layer 953. This makes it possible to prevent defects in the light emitting element due to static electricity or the like.

[0246] The light emitting device described above has a large number of minute light emitting elements arranged in a matrix, which are called pixels. Since each can be controlled by the FET formed in the This light emitting device can be suitably used as a device.

[0247] <Lighting equipment> A lighting device according to one embodiment of the present invention will be described with reference to FIG. 8. FIG. 8(B) shows a lighting device 8(A) is a cross-sectional view taken along the line e-f in FIG. 8(B).

[0248] The lighting device has a first electrode 401 formed on a light-transmitting substrate 400 serving as a support. The first electrode 401 corresponds to the anode 101 in FIGS. 1(A) and 1(B). When light is extracted from the electrode 401 side, the first electrode 401 is made of a light-transmitting material. Complete.

[0249] A pad 412 for supplying a voltage to the second electrode 404 is formed on the substrate 400 .

[0250] An EL layer 403 is formed on the first electrode 401. The EL layer 403 is shown in FIG. These correspond to the EL layer 103 in (B). I want to be.

[0251] The second electrode 404 is formed to cover the EL layer 403. The second electrode 404 is This corresponds to the cathode 102. When light is extracted from the first electrode 401 side, the second electrode 404 The second electrode 404 is formed by connecting to the pad 412. The voltage is supplied by

[0252] The first electrode 401, the EL layer 403, and the second electrode 404 form a light-emitting element. The light emitting element is sealed by fixing a sealing substrate 407 using sealing materials 405 and 406. The lighting device is completed by this. Either one of the sealing materials 405 and 406 can be used. In addition, a desiccant can be mixed into the inner sealing material 406, which will absorb moisture. This allows the device to be worn, leading to improved reliability.

[0253] In addition, a part of the pad 412 and the first electrode 401 is extended outside the sealing materials 405 and 406. By providing a terminal on the board, it can be used as an external input terminal. An IC chip 420 equipped with the above may be provided.

[0254] ≪Electronic equipment≫ Examples of electronic devices according to one embodiment of the present invention will be described. video equipment (also called televisions or television receivers), computers, etc. Digital cameras, digital video cameras, digital photo frames, mobile phones ( Mobile phones, also known as mobile phone devices, portable game machines, portable information terminals, sound reproducing devices, Examples include large game machines such as dick machines. Specific examples of these electronic devices are shown below. .

[0255] 9A 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 configured by arranging light-emitting elements in a matrix.

[0256] 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

[0257] 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.

[0258] FIG. 9(B1) shows a computer, which includes a main body 7201, a housing 7202, a display unit 7203, and a keyboard. keyboard 7204, external connection port 7205, pointing device 7206, etc. In addition, this computer uses light emitting elements arranged in a matrix for the display portion 7203. The computer shown in FIG. 9(B1) is manufactured in the form shown in FIG. 9(B2). The computer in FIG. 9(B2) may have a keyboard 7204, a pointing device, A second display unit 7210 is provided instead of the device 7206. The second display unit 7210 is a touch panel, and the input display is displayed on the second display unit 7210. Input can be made by operating the second display unit 72 or a dedicated pen. The display unit 10 is not only for input but also for displaying other images. The 203 may also be a touch panel. The two screens are connected by a hinge. This also prevents problems such as scratches or breakage of the screen when storing or transporting it. This can be done.

[0259] 9C and 9D show an example of a portable information terminal. In addition to the display unit 7402 incorporated in the The portable information terminal is equipped with a speaker 7405, a microphone 7406, and the like. The display portion 7402 is fabricated and arranged in a matrix.

[0260] The portable information terminals shown in FIGS. 9C and 9D have a function to display a screen by touching the display portion 7402 with a finger or the like. It may also be possible to input information. In this case, the information may be input by making a call or Operations such as creating an email can be performed by touching the display portion 7402 with a finger or the like. can.

[0261] 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.

[0262] For example, when making a call or creating an email, the display unit 7402 is used to input characters. This is the main character input mode, and you can input characters displayed on the screen. It is preferable to display a keyboard or number buttons on most of the screen of the display portion 7402. I wish.

[0263] The mobile information terminal also has a sensor for detecting tilt, such as a gyro or acceleration sensor. By providing a detection device, the orientation (portrait or landscape) of the portable information terminal can be determined. The screen display can be automatically switched.

[0264] 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.

[0265] 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.

[0266] 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.

[0267] The electronic device can be used by appropriately combining the configurations shown in this specification. .

[0268] In addition, it is preferable to use the light-emitting element of one embodiment of the present invention in a display portion. It is possible to provide a light-emitting element with high efficiency. Therefore, an electronic device including a light-emitting element according to one embodiment of the present invention can consume less power. It can be a small electronic device.

[0269] FIG. 10 shows an example of a liquid crystal display device in which a light-emitting element is used as a backlight. The liquid crystal display device includes a housing 901, a liquid crystal layer 902, a backlight unit 903, and a housing 904. 04, and the liquid crystal layer 902 is connected to a driver IC 905. A light emitting element is used in the terminal 903 , and a current is supplied to the terminal 906 .

[0270] The light-emitting element of one embodiment of the present invention is preferably used as the light-emitting element, and the light-emitting element is preferably used as the liquid crystal display element. By applying this to the backlight of a display device, it is possible to obtain a backlight with reduced power consumption. can be done.

[0271] Fig. 11 shows an example of a desk lamp according to one embodiment of the present invention. The lighting device has a housing 2001 and a light source 2002, and uses a light emitting element as the light source 2002. The position is used.

[0272] FIG. 12 shows an example of an indoor lighting device 3001. The lighting device 3001 includes one of the following features of the present invention. It is preferable to use a light-emitting element according to the embodiment.

[0273] An automobile according to one embodiment of the present invention is shown in Figure 13. The automobile has a windshield and a dash panel. The display area 5000 to the display area 5005 are light-emitting elements. The display region is preferably formed using the light-emitting element of one embodiment of the present invention. This reduces the power consumption of the display areas 5000 to 5005, making it possible to It is suitable for.

[0274] The display area 5000 and the display area 5001 are light-emitting devices provided on the windshield of the automobile. The light-emitting element is a display device using a first electrode and a second electrode. By using electrodes that can be seen through to the other side, a so-called see-through display can be achieved. If the display is see-through, it can be installed on the windshield of a car. Even if the device is placed in a location, it can be installed without obstructing the view. When a transistor is provided, an organic transistor made of an organic semiconductor material or an oxide A light-transmitting transistor, such as a transistor using a semiconductor, is preferably used.

[0275] The display area 5002 is a display device that uses light-emitting elements provided in the pillar portion. In the area 5002, an image from an imaging means provided on the vehicle body is projected, and the pillar Similarly, it can complement the view obstructed by the The display area 5003 is a view blocked by the vehicle body, and is captured by an imaging means provided on the outside of the vehicle. By projecting images from the surrounding area, blind spots can be filled and safety can be improved. By projecting images that complement the unseen parts, safety checks can be performed more naturally and without discomfort. It is possible.

[0276] The display area 5004 and the display area 5005 display navigation information, a speedometer, RPM, and mileage. It can provide a variety of information, including distance, fuel level, gear status, and air conditioning settings. The display items and layout can be changed as needed to suit the user's preferences. This information can also be provided in the display areas 5000 to 5003. The display areas 5000 to 5005 can also be used as lighting devices.

[0277] Figures 14(A) and 14(B) show an example of a foldable tablet terminal. 4(A) shows the tablet terminal in an open state, and the tablet terminal includes a housing 9630, a display unit 9631a, and a , display unit 9631b, display mode changeover switch 9034, power switch 9035, The tablet has a power mode changeover switch 9036 and a fastener 9033. The terminal includes a light-emitting device including a light-emitting element of one embodiment of the present invention in a display portion 9631a and a display portion 96 31b or both.

[0278] A part of the display unit 9631a can be used as a touch panel area 9632a. By touching the operation keys 9637, data can be input. In 1a, for example, half of the area has a display function only, and the other half The display unit 963 has a touch panel function, but is not limited to this. The entire area of ​​the display unit 96 may have a touch panel function. The entire surface of 31a is displayed as a keyboard button to serve as a touch panel, and the display part 9631b is displayed. It can be used as a screen.

[0279] In addition, in the display unit 9631b, as in the display unit 9631a, The part can be used as a touch panel area 9632b. By touching the area where the display switch button 9639 is displayed with your finger or a stylus, Keyboard buttons can be displayed on the display portion 9631b.

[0280] In addition, when touching the touch panel area 9632a and the touch panel area 9632b at the same time, You can also input the character.

[0281] A display mode changeover switch 9034 is used to change the display orientation, such as portrait or landscape. You can switch between black and white and color display. The switch 9036 is an external switch that is detected by a light sensor built into the tablet terminal. The display brightness can be optimized according to the amount of light. In addition to sensors, other detection devices such as gyros and acceleration sensors that detect tilt are also available. may be incorporated.

[0282] FIG. 14A shows an example in which the display area of ​​the display portion 9631b is the same as that of the display portion 9631a. However, there is no particular limitation, and one size may be different from the other size. The display quality may also differ. For example, one display panel may be able to display a higher resolution image than the other. It may also be used as a rule.

[0283] FIG. 14(B) shows the tablet terminal in the closed state. Body 9630, solar cell 9633, charge / discharge control circuit 9634, battery 9635, DCD 14B shows an example in which a charge / discharge control circuit 9636 is provided. As an example of 4, a configuration having a battery 9635 and a DC-DC converter 9636 It shows.

[0284] In addition, since the tablet device can be folded in half, when not in use, the case 9630 is closed. Therefore, the display portions 9631a and 9631b can be protected. This makes it possible to provide a tablet device that is highly durable and reliable even for long-term use.

[0285] In addition, the tablet terminals shown in Figs. 14(A) and 14(B) can be used in various Functions that display information (still images, videos, text images, etc.), calendars, dates, or times The function to display information on the display unit, and the function to input or edit the information displayed on the display unit. It has input functions, functions to control processing using various software (programs), etc. It is possible.

[0286] The solar cell 9633 attached to the surface of the tablet terminal supplies power to the touch panel. The solar cell 9633 can be supplied to a display unit, a video signal processor, or the like. The battery 9635 can be efficiently charged by installing it on one or both sides of the housing 9630. This is preferable because it is possible to configure the device to perform the above.

[0287] The configuration and operation of the charge / discharge control circuit 9634 shown in FIG. 14(B) are shown in FIG. A block diagram is shown in Fig. 14(C) and will be explained. 635, DC-DC converter 9636, converter 9638, switches SW1 to SW3 , the display unit 9631, the battery 9635, the DC-DC converter 963 6. The converter 9638 and the switches SW1 to SW3 are configured to perform the charge / discharge control shown in FIG. 14(B). This corresponds to the circuit 9634.

[0288] First, an example of operation when power is generated by the solar cell 9633 using external light will be described. The power generated by the solar cell is converted to DC voltage to charge the battery 9635. The voltage is increased or decreased by the DC converter 9636. When the power charged by the solar cell 9633 is used, switch SW1 is turned on and the The inverter 9638 increases or decreases the voltage to the voltage required for the display unit 9631. When not displaying on the display unit 9631, turn SW1 off and SW2 on. The configuration may be such that the battery 9635 is charged.

[0289] Although the solar cell 9633 is shown as an example of a power generating means, the power generating means is not particularly Other power generating devices such as, but not limited to, piezoelectric elements (piezo elements) and thermoelectric conversion elements (Peltier elements) may also be used. The battery 9635 may be charged by wireless (contactless) means. It can be combined with a non-contact power transmission module that transmits and receives power to charge, or other charging methods. The power generating means may be omitted.

[0290] Furthermore, if the display unit 9631 is provided, the tablet terminal shown in FIG. Not limited.

[0291] 15(A) to 15(C) show a foldable mobile information terminal 9310. 15(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. 15C 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.

[0292] 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]

[0293] (Synthesis Example 1) In this synthesis example, the organic compound of one embodiment of the present invention shown in Embodiment 1 as structural formula (101) was synthesized. The compound 4-(6;2'-binaphthyl-2-yl)-4',4''-diphenyltriphenyl This paper describes a method for synthesizing BBA(βN2)B. The structural formula of )B is shown below.

[0294] [ka]

[0295] <Step 1: Synthesis of 6-bromo-2,2'-binaphthyl> In a 200 mL three-neck flask, 5.7 g (20 mmol) of 2,6-dibromonaphthalene 3.4 g (20 mmol) of 2-naphthylboronic acid and 0.30 g (1.0 mmol) ) tri(ortho-tolyl)phosphine, 80 mL of toluene, and 20 mL of ethanol. The mixture was mixed with 40 mL of an aqueous solution of potassium carbonate (2.0 mol / L), and the mixture was heated under reduced pressure. After degassing, the system was placed under a nitrogen stream. The mixture was heated to 60°C, and 0.12 g (0.5 mmol) of palladium(II) acetate was added and stirred at 80°C for 2 hours. The mixture was cooled to room temperature, and the precipitated solid was collected by suction filtration. The resulting solid was washed with 2.1 g of a light brown solid. The filtrate was washed with water and saturated saline, and the organic layer was dried over magnesium sulfate. The solid obtained by gravity filtration and concentrating the filtrate was analyzed by high performance liquid chromatography (HPLC) The product was purified using a mobile phase of chloroform to obtain 2.8 g of a white solid. The white solid obtained by C purification and the light brown solid recovered after the reaction were combined to give 4.9 g of the target product. The synthesis scheme for Step 1 is shown below.

[0296] [ka]

[0297] Step 2: 4,4'-diphenyl-4''-(4,4,5,5-tetramethyl-1, Synthesis of 3,2-dioxaborolan-2-yltriphenylamine In a 200 mL three-neck flask, add 2.3 g (5.0 mmol) of 4-bromo-4',4'' -diphenyltriphenylamine and 1.3 g (5.0 mmol) of bis(pinacolato) Diboron and 0.11 g (0.40 mmol) of 2-di-tert-butylphosphino- 2',4',6'-triisopropylbiphenyl (abbreviation: tBuXphos) and 0.9 Add 7 g of potassium acetate and 25 mL of xylene, mix, and degas the mixture under reduced pressure. After this, the system was purged with nitrogen. After heating the mixture to 60°C, 92 mg (0.10 mmol) of [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (abbreviation: Pd(dppf)Cl2) was added and stirred at 120°C for 5 hours. After confirming by thin layer chromatography (TLC) that the raw materials had disappeared, The synthesis scheme for step 2 is shown below.

[0298] [ka]

[0299] Step 3: 4-(6;2'-binaphthyl-2-yl)-4',4''-diphenyl Synthesis of triphenylamine (abbreviation: BBA(βN2)B) To the mixture obtained in step 2, 1.7 g (5.0 mmol) of 6-bromo-2,2'- binaphthyl and 0.88 g (0.20 mmol) of 2-di-tert-butylphosphino -2',4',6'-triisopropylbiphenyl (abbreviation: tBuXphos) and 3. 2 g (10 mmol) of cesium carbonate was added, and the mixture was degassed under reduced pressure. The mixture was heated to 60°C under a stream of pure air. 1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (abbreviation After adding Pd(dppf)Cl2, the mixture was stirred at 120°C for 8.5 hours. The solid was collected by suction filtration and washed with toluene, water, and ethanol, and the target compound was identified. The brown solid was obtained in 3.3 g with a yield of over 99%. The synthesis scheme for Step 3 is shown below. .

[0300] [ka]

[0301] of the obtained material 1 The 1 H NMR data is shown in FIG. 16 and the numerical data is shown below. In this synthesis example, BBA(βN2)B, an organic compound according to one embodiment of the present invention, was obtained. I found out that... 1 H NMR (chloroform-d, 500 MHz): δ = 7.26-7.35 (m, 8H ), 7.45(t, J=7.5Hz, 4H), 7.49‐7.57(m, 6H), 7.6 1(d, J=7.5Hz, 4H), 7.70(d, J=8.5Hz, 2H), 7.81( dd, J1=8.5Hz, J2=1.5Hz, 1H), 7.89-7.93(m, 3H) , 7.95(d, J=7.5Hz, 1H), 7.98(d, J=8.5Hz, 1H), 8 .0(dd, J1=8.5Hz, J2=3.5Hz, 2H), 8.09(s, 1H), 8 .20(s, 2H)

[0302] The resulting solid (3.3 g) was purified by train sublimation. The solid was heated at 320°C under a pressure of 2.5 Pa for 15 hours while argon was flowing at 15 mL / min. After purification by sublimation, 2.1 g of a pale yellow solid was obtained, with a recovery rate of 64%.

[0303] Next, the absorption and emission spectra of the toluene solution of BBA(βN2)B were measured. The results are shown in Figure 17. The absorption spectrum and emission spectrum of the thin film are shown in Figure 18. The solid thin film was prepared on a quartz substrate by vacuum deposition. The measurement was carried out using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation) and The absorption spectrum of the thin film was subtracted from the spectrum measured by placing only the sample in a quartz cell. A spectrophotometer (Hitachi High-Technologies Corporation, spectrophotometer U4100) was used for the measurement. The emission spectrum was measured using a fluorometer (FS9 manufactured by Hamamatsu Photonics Co., Ltd.). 20) was used.

[0304] As can be seen from Figure 17, the toluene solution of BBA(βN2)B has absorption peaks around 358 nm and 305 nm. A peak was observed in the emission wavelength at 425 nm (excitation wavelength 360 nm). From Figure 18, the BBA(βN2)B thin film has the following wavelengths: 365 nm, 309 nm, 258 nm, and 210 nm. The absorption peak is observed around 452 nm (excitation wavelength 380 nm). From this result, it was confirmed that BBA(βN2)B emits blue light. It was found that it can also be used as a host for photo-sensitive materials and visible fluorescent materials.

[0305] In addition, thin films of BBA(βN2)B are less likely to aggregate even in the atmosphere, and their morphology changes little. It was found that the film quality was good.

[0306] Next, the HOMO and LUMO levels of BBA(βN2)B were measured by cyclic voltammetry. The results are calculated based on CV measurements. The calculation method is shown below.

[0307] 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 (n-B u4NClO4) (Tokyo Chemical Industry Co., Ltd., Catalog No.: T0836) at 100 mmol / The measurement target is dissolved in a solution to a concentration of 2 mmol / L. The working electrode was a platinum electrode (PT, manufactured by BAS Co., Ltd.). E platinum electrode), and a platinum electrode (B.A.S. Co., Ltd., VC-3 P) was used as the auxiliary electrode. The counter electrode (5 cm) was used as the reference electrode, and Ag / Ag + Electrode (B.A.E. The measurements were carried out at room temperature (20 to 32°C). The scan rate during CV measurement was standardized to 0.1 V / sec. The oxidation potential Ea [V] and reduction potential Ec [V] were measured. The potential of the reduction wave is defined as the midpoint potential of the reduction wave, and Ec is defined as the midpoint potential of the reduction-oxidation wave. The potential energy of the reference electrode relative to the vacuum level is -4.94 eV. Since it is known that the HOMO level [eV] = -4.94-Ea, the LUMO level [eV ]=-4.94-Ec, calculate the HOMO and LUMO levels. It is possible.

[0308] The CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th cycle and the 1st cycle were measured. The electrical stability of the compounds was investigated by comparing the oxidation-reduction waves of the first group.

[0309] As a result, the HOMO level of BBA(βN2)B is -5.47 eV and the LUMO level is -2. In addition, in repeated measurements of the oxidation-reduction wave, When comparing the waveform after 100 cycles with the first, the oxidation potential Ea [V] was 85%. The peak intensity of BBA(βN2)B was maintained, which indicates that BBA(βN2)B has excellent resistance to oxidation. It was confirmed to be good.

[0310] In addition, differential scanning calorimetry (DSC) of BBA(βN2)B was performed. DSC (Differential Scanning Calorimetry) was performed using a PerkinElmer Pyris 1D The differential scanning calorimetry was performed at a temperature rise rate of 40°C / min, from -10°C to After heating to 280°C, the temperature was maintained for 1 minute, and then the temperature was decreased at a rate of 100°C / min. The sample was cooled to -10°C and then held at -10°C for 3 minutes. This process was repeated twice. From the results of the first DSC measurement, the glass transition temperature of BBA(βN2)B was 110°C, and the crystallization temperature It was revealed that the temperature is 161°C and the melting point is 266°C, making it a material with extremely high heat resistance. It was shown to be of quality.

[0311] Furthermore, thermogravimetry and differential thermal analysis of BBA(βN2)B were performed. Differential Thermal Analysis (TG-DTA) was performed. The measurements were carried out using a high-vacuum differential thermobalance (manufactured by Bruker AXS, TG- The measurement was carried out at atmospheric pressure, with a temperature rise rate of 10°C / min, and nitrogen. The analysis was carried out under the condition of air flow (flow rate 200 mL / min). A(βN2)B is the temperature at which the weight determined by thermogravimetry becomes -5% of the weight at the start of the measurement (decomposition temperature). The temperature (degrees) was found to be over 500°C, indicating that it is a highly heat-resistant material. . [Example]

[0312] (Synthesis Example 2) In this synthesis example, the organic compound of one embodiment of the present invention shown in Embodiment 1 as structural formula (122) was synthesized. The compound N,N-bis(4-biphenylyl)-2,2'-binaphthyl-6-amine (abbreviated The synthesis method of BBA(βN2) is explained below. The structural formula of BBA(βN2) is as follows: show.

[0313] [ka]

[0314] <Step 1: Synthesis of 6-bromo-2,2'-binaphthyl> 6-Bromo-2,2'-binaphthyl was synthesized in the same manner as in Step 1 of Example 1.

[0315] <Step 2: N,N-bis(4-biphenylyl)-2,2'-binaphthyl-6-amine Synthesis of (abbreviation: BBA(βN2)) In a 200 mL three-neck flask, add 1.7 g (5.1 mmol) of 6-bromo-2,2'-binazone. butyl, 1.6 g (5.1 mmol) bis(4-biphenylyl)amine, and 96 mg (0.20mmol) 2-dicyclohexylphosphino-2',4',6'-triiso Propylbiphenyl (abbreviation: XPhos) and 1.5 g (15 mmol) of t-butoxy Sodium was added and the system was purged with nitrogen. 26 mL of xylene was added to the mixture, and the After degassing under pressure, the system was purged with nitrogen. The mixture was heated to 80°C, and 62 mg of (0.10 mmol) bis(dibenzylideneacetone)palladium(0) (abbreviation: Pd (dba)2) was added, and the mixture was stirred at 120°C for 5 hours. After stirring, the mixture was cooled to room temperature. The resulting mixture was washed with water and saturated saline, and the organic and inorganic layers were separated. The mixture was dried over magnesium sulfate, and the filtrate was concentrated to give a solid. The solid was purified by high performance liquid chromatography (HPLC) (mobile phase: chloroform). After purification, 2.5 g of the desired white solid was obtained in 87% yield. The team is shown below.

[0316] [ka]

[0317] of the obtained material 1 The H-NMR data is shown in Figure 19, and the numerical data is shown below. This synthesis example yielded BBA(βN2), an organic compound according to one embodiment of the present invention. I found out that... 1 H NMR (chloroform-d, 500 MHz): δ = 7.27 (d, J = 8.5 Hz , 4H), 7.33(t, J=7.5Hz, 2H), 7.41‐7.46(m, 5H), 7.48‐7.58(m, 7H), 7.62(d, J=7.5Hz, 4H), 7.76( d, J=8.5Hz, 1H), 7.83‐7.89(m, 4H), 7.94(d, J=7 .5Hz, 1H), 7.96(d, J=9.0Hz, 1H), 8.12(s, 1H), 8 .16(s, 1H)

[0318] The resulting 2.5 g solid was purified by train sublimation. The solid was heated at 310°C under a pressure of 3.5 Pa for 15 hours while argon was flowing at 15 mL / min. After purification by sublimation, 2.0 g of a pale yellow solid was obtained, with a recovery rate of 80%.

[0319] Next, the absorption and emission spectra of the toluene solution of BBA(βN2) were measured. The results are shown in Figure 20. The absorption spectrum and emission spectrum of the thin film are shown in Figure 21. The solid thin film was prepared on a quartz substrate by vacuum deposition. For the measurement, an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation) was used. The absorption spectrum of the thin film was measured by subtracting the spectrum measured by placing the sample in a quartz cell. A spectrophotometer (Hitachi High-Technologies Corporation, spectrophotometer U4100) was used for the measurement. The emission spectrum was measured using a fluorometer (FS92 manufactured by Hamamatsu Photonics Co., Ltd.). 0) was used.

[0320] As shown in Figure 20, the toluene solution of BBA(βN2) has absorption peaks around 350 nm and 290 nm. The peak of the emission wavelength was 426 nm (excitation wavelength 360 nm). From 21, the BBA(βN2) thin film is around 400, 354, 295, 258, and 208 nm. The absorption peak is seen at 444 nm (excitation wavelength 370 nm), and the emission wavelength peak is seen at 444 nm (excitation wavelength 370 nm). From these results, it was confirmed that BBA(βN2) emits blue light. The compound of the present invention can also be used as a host for luminescent materials and fluorescent materials emitting light in the visible range. I found out that...

[0321] In addition, thin films of BBA(βN2) are resistant to aggregation even in the atmosphere and show little change in shape. The film quality was found to be good.

[0322] The HOMO and LUMO levels of BBA(βN2) were determined by cyclic voltammetry (C V) was calculated based on the measurements. The calculation method is the same as that described in Example 1, so it is omitted here.

[0323] As a result, the HOMO level of BBA(βN2) is −5.45 eV and the LUMO level is −2.4 0 eV. In addition, in the repeated measurement of the oxidation-reduction wave, When comparing the waveform after 100 cycles with that after 100 cycles, the oxidation potential Ea maintained 87% of the peak intensity. Furthermore, the reduction potential Ec maintained a peak intensity of 86%, which indicates that BBA(βN 2) was confirmed to have very good resistance to oxidation and reduction.

[0324] In addition, differential scanning calorimetry (DSC) of BBA(βN2) DSC (Differential Scanning Calorimetry) was performed using a PerkinElmer Pyris 1DS The differential scanning calorimetry was performed at a heating rate of 40°C / min from -10°C to After heating to 250°C, hold at that temperature for 1 minute, then cool at a rate of 50°C / min. The sample was cooled to 0°C and then held at -10°C for 3 minutes. This cycle was repeated twice. From the DSC measurement results, the glass transition point of BBA(βN2) is 95℃ and the melting point is 210℃. Something became clear.

[0325] Furthermore, thermogravimetry-differential thermal analysis (TDS) of BBA(βN2) was performed. The measurement was carried out using a high-precision thermal analysis (Takamatsu Thermal Analysis). Empty differential thermobalance (Bruker AXS, TG-DTA2410S) The measurement was carried out at atmospheric pressure, with a temperature rise rate of 10°C / min, under a nitrogen gas flow (flow rate 2 The thermogravimetric and differential thermal analysis was carried out under the conditions of 00 mL / min. It was found that the temperature at which the weight of the sample decreased by 5% from the initial value (decomposition temperature) was 453°C or higher. It was shown that the material has high heat resistance. [Example]

[0326] (Synthesis Example 3) In this synthesis example, the organic compound of one embodiment of the present invention shown in Embodiment 1 as structural formula (116) was synthesized. The compound 4-(3;2'-binaphthyl-2-yl)-4',4''-diphenyltriphenyl This article explains the synthesis method of BBA(βN2)B-02. The structural formula of βN2)B-02 is shown below.

[0327] [ka]

[0328] <Step 1: Synthesis of 3-bromo-2,2'-binaphthyl> 3.0 g (11 mmol) of 2,3-dibromonaphthalene and 1.8 g (11 mmol) of 2-naphthylboronic acid g (11 mmol), tri(ortho-tolyl)phosphine 96 mg (0.031 mmol ), toluene 50 mL, ethanol 15 mL, potassium carbonate aqueous solution (potassium carbonate 2.9 g / 11 mL of water) 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. Then, 24 mg ( 0.011 mmol) was added and stirred at room temperature for 4 hours. Water was added to the resulting mixture, and the aqueous 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 a solid. The obtained solid was subjected to high performance liquid chromatography (HPLC) (mobile phase: chloroform). The target compound, 3-bromo-2,2'-binaphthyl, was obtained as a white solid (yield 1.8 g, 52% yield. The synthesis scheme for Step 1 is shown below.

[0329] [ka]

[0330] The obtained solid 1 The 1 H NMR chart is shown in Figure 73, and the numerical data is shown below. It was found that 3-bromo-2,2'-binaphthyl was obtained.

[0331] 1 H NMR (chloroform-d, 500 MHz): δ = 8.22 (s, 1H), 7.9 3‐7.88(m, 5H), 7.85‐7.80(m, 2H), 7.63(dd, J=9 .0, 2.0Hz, 1H), 7.54‐7.46(m, 4H)

[0332] Step 2: 4,4'-diphenyl-4''-(4,4,5,5-tetramethyl-1, Synthesis of 3,2-dioxaborolan-2-yltriphenylamine 4,4'-Diphenyl-4''-(4,4,5,5-tetramethyl-1,3,2-dioxa (Saborolan-2-yl)triphenylamine was synthesized in the same manner as in Step 2 of Example 1.

[0333] Step 3: 4-(3;2'-binaphthyl-2-yl)-4',4''-diphenyl Synthesis of triphenylamine (abbreviation: BBA(βN2)B-02) 4,4'-Diphenyl-4''-(4,4,5,5-tetramethyl-1,3,2-dioxa 3.0 g (5.5 mmol) of saborolan-2-yltriphenylamine and 3-bromo- 2,2'-binaphthyl 1.8g (5.5mmol), tri(ortho-tolyl)phosphine 50 mg (0.17 mmol), potassium carbonate aqueous solution 1.5 g / 6 mL (11 mmol) , 50 mL of toluene, and 15 mL of ethanol were placed in a 1 L three-neck flask equipped with a reflux condenser. The mixture was degassed under reduced pressure, and then the atmosphere in the system was replaced with nitrogen. The mixture was heated at 80°C. To the mixture was added 12 mg (0.055 mmol) of palladium(II) acetate. The mixture was stirred at 0°C for 10 hours. Water was added to the resulting mixture, and 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 obtain a solid. This solid was analyzed by HPLC ( The target pale yellow solid was obtained in an amount of 1.1 g in a yield of 31%. %. 1.1 g of the resulting solid was purified by train sublimation. Sublimation purification was carried out by flowing argon at 15 mL / min, and solidifying the solution at 310°C under a pressure of 4.2 Pa. The mixture was heated for 16 hours. After purification by sublimation, 660 mg of a pale yellow solid was obtained with a recovery rate of 60%. The synthetic scheme for step 3 is shown below.

[0334] [ka]

[0335] of the obtained material 1 The H-NMR data is shown in Figure 22, and the numerical data is shown below. It was found that BBA(βN2)B-02 was obtained through this synthesis example.

[0336] 1 H NMR (dichloromethane-d2, 500 MHz): δ = 8.03 (s, 1H), 7 .99(s, 1H), 7.94(dd, J=5.5, 4.0Hz, 2H), 7.87‐7 .82(m, 3H), 7.77(d, J=8.0Hz, 1H), 7.57(d, 4H), 7.55‐7.47(m, 8H), 7.43(t, J=7.5Hz, 4H), 7.38( dd, J=8.5, 1.5Hz, 1H), 7.31(t, J=7.5Hz, 2H), 7. 18(d, J=8.5Hz, 2H), 7.12(d, J=8.5Hz, 4H), 7.00 (d, J=8.5Hz, 2H)

[0337] Next, the absorption and emission spectra of the thin film of BBA(βN2)B-02 were measured. The results are shown in Figure 23. The solid thin film was prepared on a quartz substrate by vacuum deposition. The spectra were measured using a spectrophotometer (Hitachi High-Technologies Corporation U4 spectrophotometer). 100) was used. The emission spectrum was measured using a fluorometer (Hamamatsu Photonik Co., Ltd. The FS920 manufactured by FUJITSU was used.

[0338] From Figure 23, the BBA(βN2)B-02 thin film has 351 nm, 310 nm, 255 nm, The absorption peak is observed around 210 nm, and the emission wavelength peak is around 422 nm (excitation wavelength 3 60 nm). Also, BBA(βN2)B-02 is blue. It was confirmed that the compound of one embodiment of the present invention emits light in the visible region. It turns out that it can also be used as a host.

[0339] In addition, thin films of BBA(βN2)B-02 are resistant to aggregation even in the atmosphere and do not change in shape. It was found that the film quality was good.

[0340] The HOMO and LUMO levels of BBA(βN2)B-02 were investigated by cyclic voltammetry. The calculation method was the same as that in Example 1, so Abbreviated.

[0341] As a result, the HOMO level of BBA(βN2)B‐02 is −5.48 eV, and the LUMO level is In addition, the redox wave was measured repeatedly and found to be 1. When comparing the waveforms after the first and 100th cycles, the oxidation potential Ea was 92% of the peak strength. BBA(βN2)B‐02 has excellent resistance to oxidation. was confirmed.

[0342] In addition, differential scanning calorimetry (DSC) of BBA(βN2)B-02 was performed by PerkinElmer. The differential scanning calorimetry was performed using a Pyris1 DSC manufactured by FUJITSU ELECTRONICS CO., LTD. The temperature was increased at a rate of 40°C / After heating from -10°C to 335°C in min, the temperature was kept at the same temperature for 1 minute, and then the temperature was lowered at a The temperature was cooled to -10°C at 100°C / min, and then the temperature was held at -10°C for 3 minutes. The results of the second measurement were used. The glass transition temperature of is 116°C, which indicates that it is a compound with good heat resistance. It became clear that:

[0343] Furthermore, thermogravimetry and differential thermal analysis (TTA) of BBA(βN2)B-02 were performed. ry-Differential Thermal Analysis) was performed. The thermometer was equipped with a high-vacuum differential thermobalance (Bruker AXS, TG-DTA2 The measurement was carried out at atmospheric pressure, with a temperature rise rate of 10°C / min, under a nitrogen gas flow. (Flow rate 200 mL / min). The temperature at which the weight calculated from the above becomes -5% of the weight at the start of measurement (decomposition temperature) is around 430°C. This indicates that the material has high heat resistance. [Example]

[0344] (Synthesis Example 4) In this synthesis example, the organic compound of one embodiment of the present invention shown in Embodiment 1 as structural formula (110) was synthesized. The compound 4-(2;2'-binaphthyl-7-yl)-4',4''-diphenyltriphenyl This article explains the synthesis method of BBA(βN2)B-03. The structural formula of βN2)B-03 is shown below.

[0345] [ka]

[0346] Step 1: 4,4'-diphenyl-4''-(4,4,5,5-tetramethyl-1, Synthesis of 3,2-dioxaborolan-2-yltriphenylamine 4,4'-Diphenyl-4''-(4,4,5,5-tetramethyl-1,3,2-dioxa (Saborolan-2-yl)triphenylamine was synthesized in the same manner as in Step 2 of Synthesis Example 1.

[0347] Step 2: 4-(2;2'-binaphthyl-7-yl)-4',4''-diphenyl Synthesis of triphenylamine (abbreviation: BBA(βN2)B-03) 4,4'-Diphenyl-4''-(4,4,5,5-tetramethyl-1,3,2-dioxa 3.7 g (6.8 mmol) of saborolan-2-yltriphenylamine and 7-bromo- 2,2'-binaphthyl 2.3g (6.8mmol), tri(ortho-tolyl)phosphine 42 mg (0.13 mmol), potassium carbonate aqueous solution 1.9 g / 15 mL (14 mmol ), 70 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 atmosphere in the system was replaced with nitrogen. To this mixture was added 15 mg (0.068 mmol) of palladium(II) acetate. The mixture was stirred at 100°C for 7 hours. Water was added to the resulting mixture, and the aqueous layer was extracted with toluene. The resulting extract and organic layer were combined, washed with water and saturated saline, and dried over magnesium sulfate. The mixture was gravity filtered and the filtrate was concentrated to give a white solid. Purification by LC (mobile phase: chloroform) gave 3.5 g of the target pale yellow solid. The yield was 79%. The resulting 3.5 g of solid was purified by sublimation using the train sublimation method. The sublimation purification was carried out under a pressure of 4.1 Pa and 32 The solid was heated at 0°C for 16 hours. After sublimation purification, 3.0 g of a pale yellow solid was obtained, with a recovery rate of 85%. The synthesis scheme for Step 2 is shown below.

[0348] [ka]

[0349] of the obtained material1 The H-NMR data is shown in Figure 24, and the numerical data is shown below. It was found that BBA(βN2)B-03 was obtained through this synthesis example.

[0350] 1 H-NMR (dichloromethane-d2, 500MHz): δ = 8.26 (s, 1H), 8 .24(s, 1H), 8.17(s, 1H), 8.01-7.90(m, 7H), 7.8 1(dd, J=8.5, 1.5Hz, 1H), 7.73(d, J=9.5Hz, 2H), 7.62(d, J=8.5Hz, 4H), 7.59-7.50(m, 6H), 7.44( t, J=7.5Hz, 4H), 7.34‐7.26(m, 8H)

[0351] Next, the absorption and emission spectra of the toluene solution of BBA(βN2)B-03 The results of measuring the absorption spectrum and emission spectrum of the thin film are shown below. The sample preparation method, measurement method, and measurement device are the same as those shown in the examples. The explanation will be omitted.

[0352] From the measurement results, the toluene solution of BBA(βN2)B-03 has an absorption peak around 351 nm. The peak emission wavelength was 411 nm (excitation wavelength 351 nm). The thin film of A(βN2)B-03 has absorption peaks at around 356 nm, 266 nm, and 210 nm. The peak of the emission wavelength was observed around 435 nm (excitation wavelength 360 nm). From the results, it was confirmed that BBA(βN2)B-03 emits blue light. The compound of one embodiment can also be used as a host for a luminescent material or a fluorescent material emitting light in the visible range. I found out that...

[0353] In addition, thin films of BBA(βN2)B-03 are resistant to aggregation even in the atmosphere and do not change in shape. It was found that the film quality was good.

[0354] The HOMO and LUMO levels of BBA(βN2)B-03 were investigated by cyclic voltammetry. The calculation method was the same as that in Example 1, so Abbreviated.

[0355] As a result, the HOMO level of BBA(βN2)B‐03 is −5.47 eV, and the LUMO level is In addition, the redox wave was measured repeatedly and found to be 1. When comparing the waveforms after the first and 100th cycle, the oxidation potential Ea was 89% of the peak strength. BBA(βN2)B‐03 has excellent resistance to oxidation. was confirmed.

[0356] Furthermore, thermogravimetry and differential thermal analysis (TTA) of BBA(βN2)B-03 were performed. ry-Differential Thermal Analysis) was performed. The thermometer was equipped with a high-vacuum differential thermobalance (Bruker AXS, TG-DTA2 The measurement was carried out at atmospheric pressure, with a temperature rise rate of 10°C / min, under a nitrogen gas flow. (Flow rate 200 mL / min). The temperature at which the weight calculated from the above becomes -5% of the weight at the start of measurement (decomposition temperature) is around 474°C. This indicates that the material has high heat resistance.

[0357] In addition, differential scanning calorimetry (DSC) of BBA(βN2)B-03 was performed by PerkinElmer. The differential scanning calorimetry was performed using a Pyris1 DSC manufactured by FUJITSU ELECTRONICS CO., LTD. The temperature was increased at a rate of 40°C / After heating from -10°C to 355°C in min, the temperature was kept at the same temperature for 1 minute, and then the temperature was lowered at a The temperature was cooled to -10°C at 100°C / min, and then the temperature was held at -10°C for 3 minutes. The DSC measurement was performed twice in a row, and the second measurement result was used. The glass transition temperature of is 116°C, which indicates that it is a compound with good heat resistance. It became clear that: [Example]

[0358] (Synthesis Example 5) In this synthesis example, the compound of the present invention shown in the structural formula (114) in Embodiment 1 was synthesized. The organic compound 4-(2;1'-binaphthyl-6-yl)-4',4''-diphenyl This section explains the synthesis method of triphenylamine (abbreviated as BBAαNβNB). The structural formula of βNB is shown below.

[0359] [ka]

[0360] Step 1: 4,4'-diphenyl-4''-(4,4,5,5-tetramethyl-1, Synthesis of 3,2-dioxaborolan-2-yltriphenylamine 4,4'-Diphenyl-4''-(4,4,5,5-tetramethyl-1,3,2-dioxa (Saborolan-2-yl)triphenylamine was synthesized in the same manner as in Step 2 of Synthesis Example 1.

[0361] Step 2: 4-(2;1'-binaphthyl-6-yl)-4',4''-diphenyl Synthesis of triphenylamine (abbreviation: BBAαNβNB) 4,4'-Diphenyl-4''-(4,4,5,5-tetramethyl-1,3,2-dioxa 3.5 g (6.7 mmol) of saborolan-2-yltriphenylamine and 6-bromo- 2,1'-binaphthyl 2.2g (6.7mmol), tri(ortho-tolyl)phosphine 40 mg (0.13 mmol), potassium carbonate aqueous solution 1.85 g / 6.5 mL (13 mm ol), 50 mL of toluene, and 15 mL of ethanol were added to 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. To this mixture was added 15.0 mg (0.067 mmol) of palladium(II) acetate. The mixture was stirred for 3 hours at 100° C. Water was added to the resulting mixture, 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. The reaction solution was concentrated to obtain 3.5 g of a yellow solid, the target product, in a yield of 82%. The resulting 3.55 g of solid was purified by train sublimation. The solid was heated at 310°C for 15 hours under a pressure of 4.1 Pa while flowing argon at 15 mL / min. After sublimation purification, 2.5 g of the target pale yellow solid was obtained with a recovery rate of 72%. The synthesis scheme for Step 2 is shown below.

[0362] [ka]

[0363] of the obtained material 1 The H-NMR data is shown in Figure 25, and the numerical data is shown below. It was found that BBAαNβNB was obtained by this synthesis example.

[0364] 1 H-NMR (dichloromethane-d2, 500MHz): δ = 8.16 (s, 1H), 8 .29(d, J=8.5Hz, 1H), 7.99‐7.95(m, 4H), 7.92(d , J=8.0Hz, 1H), 7.85(dd, J=8.0, 1.5Hz, 1H), 7.7 4(d, J=8.5Hz, 2H), 7.67(dd, J=9.0, 1.5Hz, 1H), 7.63‐7.51(m, 11H), 7.47‐7.43(m, 5H), 7.34‐7. 26(m, 8H)

[0365] Next, the absorption and emission spectra of the toluene solution of BBAαNβNB were measured. The results of the measurement of the absorption spectrum and emission spectrum of the thin film are shown below. The sample preparation method, measurement method, and measurement device are the same as those shown in the examples, so the explanation is omitted. Abbreviated.

[0366] From the measurement results, the toluene solution of BBAαNβNB showed an absorption peak around 354 nm. The peak emission wavelength was 419 nm (excitation wavelength 354 nm). The NB thin film has absorption peaks around 358 nm, 299 nm, 251 nm, and 212 nm. The emission wavelength peaks were observed at around 432 nm and 449 nm (excitation wavelength 375 nm). From these results, it was confirmed that BBAαNβNB emits blue light. The compound according to one embodiment of the present invention can also be used as a host for a luminescent material or a fluorescent material that emits light in the visible range. It was found that...

[0367] In addition, thin films of BBAαNβNB are resistant to aggregation even in the atmosphere and show little change in their morphology. The film quality was found to be good.

[0368] The HOMO and LUMO levels of BBAαNβNB were measured by cyclic voltammetry (C V) was calculated based on the measurements. The calculation method is the same as that described in Example 1, so it is omitted here.

[0369] As a result, the HOMO level of BBAαNβNB is −5.47 eV and the LUMO level is −2.4 0 eV. In addition, in the repeated measurement of the oxidation-reduction wave, When comparing the waveform after 100 cycles with that after 100 cycles, the oxidation potential Ea maintained 89% of the peak intensity. This confirmed that BBAαNβNB has excellent resistance to oxidation. It was.

[0370] Furthermore, thermogravimetry-differential thermal analysis (TDS) of BBAαNβNB was performed. The measurement was carried out using a high-precision thermal analysis (Takamatsu Thermal Analysis). Empty differential thermobalance (Bruker AXS, TG-DTA2410S) The measurement was carried out at atmospheric pressure, with a temperature rise rate of 10°C / min, under a nitrogen gas flow (flow rate 2 The thermogravimetric and differential thermal analysis was carried out under the conditions of 00 mL / min. The temperature at which the weight of the sample decreased by 5% from the initial value was found to be 470°C (decomposition temperature). It was shown that this material has excellent heat resistance.

[0371] Differential scanning calorimetry (DSC) of BBAαNβNB was performed using a PerkinElmer The differential scanning calorimetry was performed using a Pyris1DSC at a heating rate of 40°C / min. After heating from -10°C to 290°C, the sample was kept at the same temperature for 1 minute and then cooled at a rate of 100°C. Cool to -10°C at ℃ / min, then hold at -10°C for 3 minutes. Repeat this process twice. The glass transition temperature of BBAαNβNB was It was found that the temperature was 113℃, which revealed that the compound has good heat resistance. . [Example]

[0372] (Synthesis Example 6) In this synthesis example, 4-(2;1'-binaphthalene)-4-(2-methyl-1-pyridinyl)-2-(2-pyridinyl)-1-pyridinyl-2-pyridinyl ... (3-yl)-4',4''-diphenyltriphenylamine (abbreviation: BBAαNβN The synthesis method of BBAαNβNB-02 is explained below. The structural formula of BBAαNβNB-02 is shown below. .

[0373] [ka]

[0374] <Step 1: Synthesis of 3-bromo-2,1'-binaphthyl> 2,3-dibromonaphthalene 3.0 g (11 mmol) and 1-naphthylboronic acid 1.8 g (11 mmol), tri(ortho-tolyl)phosphine 96 mg (0.031 mmol) , 50 mL of toluene, 15 mL of ethanol, 2 M aqueous potassium carbonate solution (potassium carbonate 2 0.9g / 11mL of water) was placed in a 200mL three-neck flask equipped with a reflux condenser, and the mixture was decompressed. After degassing, the system was replaced with nitrogen. Then, 24 mg (0.011 m) of palladium acetate was added. mol) was added and stirred at room temperature for 7 hours. Water was added to the resulting mixture, and the aqueous layer was dissolved in toluene. 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 resulting filtrate was concentrated to give a pale yellow solid. The solid was purified by HPLC (mobile phase: chloroform), and the target white solid was obtained. The synthesis scheme for Step 1 is shown below.

[0375] [ka]

[0376] The obtained solid 1 The H-NMR chart is shown in Figure 74, and the numerical data is shown below. It was found that 3-bromo-2,1'-binaphthyl was obtained.

[0377] 1 H-NMR (chloroform-d, 500MHz): δ = 8.26 (s, 1H), 7.9 4(t, J=7.0Hz, 2H), 7.87‐7.80(m, 3H), 7.59‐7.3 8 (m, 7H)

[0378] Step 2: 4,4'-diphenyl-4''-(4,4,5,5-tetramethyl-1, Synthesis of 3,2-dioxaborolan-2-yltriphenylamine 4,4'-Diphenyl-4''-(4,4,5,5-tetramethyl-1,3,2-dioxa (Saborolan-2-yl)triphenylamine was synthesized in the same manner as in Step 2 of Synthesis Example 1.

[0379] Step 3: 4-(2;1'-binaphthyl-3-yl)-4',4''-diphenyl Synthesis of triphenylamine (abbreviation: BBAαNβNB-02) 4,4'-Diphenyl-4''-(4,4,5,5-tetramethyl-1,3,2-dioxa 3.0 g (5.5 mmol) of saborolan-2-yltriphenylamine and 3-bromo- 2,1'-binaphthyl 1.8g (5.5mmol), tri(ortho-tolyl)phosphine 50 mg (0.17 mmol), potassium carbonate aqueous solution 1.5 g / 6 mL (11 mmol) , 50 mL of toluene, and 15 mL of ethanol were placed in a 1 L three-neck flask equipped with a reflux condenser. After degassing the mixture under reduced pressure, the system was replaced with nitrogen. To the mixture was added 12 mg (0.055 mmol) of palladium(II) acetate. The mixture was stirred for 4 hours at 100° C. Water was added to the resulting mixture, 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 a pale brown solid. Purification by PLC (mobile phase: chloroform) yielded the target pale yellow solid at 910 m The resulting solid (910 mg) was subjected to train sublimation. The sublimation purification was carried out under a pressure of 4.1 Pa while flowing argon at 15 mL / min. The solid was heated at 290°C for 15 hours. After purification by sublimation, 640 mg of a pale yellow solid was recovered. The synthesis scheme for Step 3 is shown below.

[0380] [ka]

[0381] of the obtained material 1 The H-NMR data is shown in Figure 26, and the numerical data is shown below. It was found that BBAαNβNB-02 was obtained through this synthesis example.

[0382] 1 H-NMR (dichloromethane-d2, 500MHz): δ = 8.05 (s, 1H), 7 .99(d, J=7.5Hz, 1H), 7.97(s, 1H), 7.92(d, J=7. 0Hz, 1H), 7.87(d, J=8.0Hz, 1H), 7.39(d, J=8.0H z, 1H), 7.58‐7.41(m, 18H), 7.33‐7.26(m, 3H), 7 .50(d, J=8.5Hz, 2H), 6.92(d, J=8.5Hz, 4H), 6.7 8(d, J=8.5Hz, 2H)

[0383] Next, the absorption and emission spectra of the toluene solution of BBAαNβNB‐02 were measured. The results of the measurements and the absorption and emission spectra of the thin films are shown. The sample preparation method, measurement method, and measurement equipment are the same as those shown in the examples, so explanations are omitted here. The details are omitted.

[0384] From the measurement results, the toluene solution of BBAαNβNB‐02 has an absorption peak around 349 nm. The peak emission wavelength was 405 nm (excitation wavelength 350 nm). The αNβNB‐02 thin films were measured at 352 nm, 294 nm, 253 nm, 224 nm and 21 The absorption peak is observed around 3 nm, and the emission wavelength peak is around 423 nm (excitation wavelength 364 From this result, it was confirmed that BBAαNβNB‐02 emits blue light. Furthermore, the compound of one embodiment of the present invention can be used as a host for a light-emitting substance or a fluorescent substance that emits light in the visible region. was also found to be available.

[0385] In addition, thin films of BBAαNβNB‐02 are resistant to aggregation even in the atmosphere and do not change in shape. It was found that the particles were small and the film quality was good.

[0386] The HOMO and LUMO levels of BBAαNβNB-02 were investigated by cyclic voltammetry. The calculation method is the same as that described in Example 1, so it is omitted here. do.

[0387] As a result, the HOMO level of BBAαNβNB‐02 is −5.48 eV and the LUMO level is − In addition, the value was found to be 2.25 eV. Comparing the waveforms after the first and 100th cycle, the oxidation potential Ea was 90% of the peak intensity. This indicates that BBAαNβNB‐02 has excellent resistance to oxidation. It was confirmed that...

[0388] In addition, differential scanning calorimetry (DSC) of BBAαNβNB‐02 was performed using PerkinElmer The differential scanning calorimetry was performed using a Pyris1 DSC manufactured by the company. The temperature was increased at a rate of 40°C / m After heating from -10°C to 290°C, the temperature was maintained for 1 minute, and then the temperature was lowered at a Cool to -10°C at 100°C / min, then hold at -10°C for 3 minutes, repeating this cycle twice The results of the second measurement were used. The glass transition temperature of the compound was found to be 125°C and the crystallization temperature was found to be 226°C. It was shown that this material has excellent heat resistance.

[0389] Furthermore, thermogravimetry and differential thermal analysis (TTA) of BBAαNβNB-02 The measurement was carried out using differential thermal analysis (DTA). The thermometer is a high-vacuum differential thermobalance (Bruker AXS, TG-DTA24 The measurement was carried out at atmospheric pressure, with a temperature rise rate of 10°C / min, under a nitrogen gas flow ( The thermogravimetric and differential thermal analysis was carried out under the condition of a flow rate of 200 mL / min. The temperature at which the weight calculated from the above becomes -5% of the weight at the start of measurement (decomposition temperature) is 430°C. This indicates that the material has high heat resistance. [Example]

[0390] (Synthesis Example 7) In this synthesis example, 4,4'-diphenyl-4,4'-diphenyl-4,4'-dione shown in the structural formula (115) in the first embodiment is used. ''-(7;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβN The synthesis method of BBAαNβNB-03 is explained below. The structural formula of BBAαNβNB-03 is shown below. .

[0391] [ka]

[0392] Step 1: 4,4'-diphenyl-4''-(4,4,5,5-tetramethyl-1, Synthesis of 3,2-dioxaborolan-2-yltriphenylamine 4,4'-Diphenyl-4''-(4,4,5,5-tetramethyl-1,3,2-dioxa (Saborolan-2-yl)triphenylamine was synthesized in the same manner as in Step 2 of Synthesis Example 1.

[0393] Step 2: 4,4'-diphenyl-4''-(7;1'-binaphthyl-2-yl) Synthesis method of triphenylamine (abbreviation: BBAαNβNB-03) 4,4'-Diphenyl-4''-(4,4,5,5-tetramethyl-1,3,2-dioxa 3.6 g (6.7 mmol) of saborolan-2-yltriphenylamine and 7-bromo- 2,1'-binaphthyl 2.2g (6.7mmol), tri(ortho-tolyl)phosphine 41 mg (0.13 mmol), potassium carbonate aqueous solution 1.8 g / 6 mL (13 mmol) , 50 mL of toluene, and 15 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 atmosphere in the system was replaced with nitrogen. The mixture was heated to 70°C. To the mixture was added 15 mg (0.067 mmol) of palladium(II) acetate. The mixture was stirred at 00°C for 7 hours. Water was added to the resulting mixture, and 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 3.4 g of a yellow solid in a yield of 7. The resulting solid (3.4 g) was purified by train sublimation. The sublimation purification was carried out at 295°C under a pressure of 3.4 Pa while flowing argon at 15 mL / min. The solid was heated for 15 hours. After purification by sublimation, 1.4 g of a pale yellow solid was obtained with a recovery rate of 42%. The synthesis scheme for Step 2 is shown below.

[0394] [ka]

[0395] of the obtained material 1 The H NMR data is shown in FIG. 27 and the numerical data is shown below. It was found that BBAαNβNB-03 was obtained through this synthesis example.

[0396] 1 H-NMR (dichloromethane-d2, 500MHz): δ = 8.12 (s, 1H), 8 .03‐8.01(m, 2H), 7.94(d, J=8.5Hz, 1H), 7.97‐7 .94(m, 2H), 7.92(d, J=8.0Hz, 1H), 7.84(dd, J=8 .5, 1.5Hz, 1H), 7.72(d, J=8.5Hz, 2H), 7.64-7.5 5(m, 11H), 7.52(t, J=7.0Hz, 1H), 7.47-7.42(m, 5H), 7.34‐7.25(m, 8H)

[0397] Next, the absorption and emission spectra of the toluene solution of BBAαNβNB‐03 were measured. The results of the measurements and the absorption and emission spectra of the thin films are shown. The sample preparation method, measurement method, and measurement equipment are the same as those shown in the examples, so explanations are omitted here. The details are omitted.

[0398] From the measurement results, the toluene solution of BBAαNβNB‐03 has an absorption peak around 352 nm. The peak emission wavelength was 427 nm (excitation wavelength 360 nm). The αNβNB‐03 thin film exhibits peaks at around 355 nm, 295 nm, 254 nm and 210 nm. An absorption peak is observed, and an emission wavelength peak is observed around 427 nm (excitation wavelength 360 nm). From these results, it was confirmed that BBAαNβNB‐03 emits blue light. The compound of one embodiment of the present invention can also be used as a host for a light-emitting substance or a fluorescent substance that emits light in the visible range. I discovered something.

[0399] In addition, thin films of BBAαNβNB‐03 are resistant to aggregation even in the atmosphere and do not change in shape. It was found that the particles were small and the film quality was good.

[0400] The HOMO and LUMO levels of BBAαNβNB-03 were investigated by cyclic voltammetry. The calculation method is the same as that described in Example 1, so it is omitted here. do.

[0401] As a result, the HOMO level of BBAαNβNB‐03 is −5.47 eV and the LUMO level is − In addition, the value was found to be 2.35 eV. Comparing the waveforms after the first and 100th cycle, the oxidation potential Ea was 89% of the peak intensity. This indicates that BBAαNβNB‐03 has excellent resistance to oxidation. It was confirmed that...

[0402] Furthermore, thermogravimetry and differential thermal analysis (TTA) of BBAαNβNB-03 The measurement was carried out using differential thermal analysis (DTA). The thermometer is a high-vacuum differential thermobalance (Bruker AXS, TG-DTA24 The measurement was carried out at atmospheric pressure, with a temperature rise rate of 10°C / min, under a nitrogen gas flow ( The thermogravimetric and differential thermal analysis was carried out under the condition of a flow rate of 200 mL / min. The temperature at which the weight calculated from the above becomes -5% of the weight at the start of measurement (decomposition temperature) is 490°C. This indicates that the material has high heat resistance.

[0403] In addition, differential scanning calorimetry (DSC) of BBAαNβNB‐03 was performed using PerkinElmer The differential scanning calorimetry was performed using a Pyris1 DSC manufactured by the company. The temperature was increased at a rate of 40°C / m After heating from -10°C to 290°C, the temperature was maintained for 1 minute, and then the temperature was lowered at a Cool to -10°C at 100°C / min, then hold at -10°C for 3 minutes, repeating this cycle twice The results of the second measurement were used. The glass transition temperature was found to be 122°C, demonstrating that the compound has good heat resistance. It became clear. [Example]

[0404] In this example, the light-emitting element 1 and the light-emitting element 2 according to one embodiment of the present invention described in the embodiment will be described. The structural formulae of the organic compounds used in the light-emitting elements 1 and 2 are shown below.

[0405] [ka]

[0406] (Method for fabricating light-emitting element 1) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The anode 101 was formed by a film deposition method. The film thickness was 70 nm and the electrode area was 4 mm 2 (2mm x 2mm).

[0407] 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.

[0408] 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.

[0409] Next, the substrate on which the anode 101 is formed is placed in a vacuum chamber so that the surface on which the anode 101 is formed faces downward. The substrate was fixed to a substrate holder installed in the vacuum evaporation device, and evaporation was performed on the anode 101 using resistance heating. The 2,3,6,7,10,11-hexacyano-1-methyl-1-methyl-2-methyl-1 ... ,4,5,8,9,12-Hexaazatriphenylene (abbreviation: HAT-CN) was evaporated to a thickness of 5 nm. The hole injection layer 111 was formed by deposition.

[0410] Next, on the hole injection layer 111, 4,4'-bis[N-(1 -naphthyl-N-phenylamino]biphenyl (abbreviation: NPB) to a thickness of 20 nm. After vapor deposition as shown in the above structural formula (101), 4-(6;2'-binaphthyl-2 -yl)-4',4''-diphenyltriphenylamine (abbreviation: BBA(βN2)B) was evaporated to a thickness of 10 nm to form a hole transport layer 112.

[0411] Next, 7-[4-(10-phenyl-9-anthracene)-2-methyl-2-(2-methyl-1,2-diphenyl- ... (phenyl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) N,N'-bis(3-methylphenyl)-N ... [3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diazo 1,6mMemFLPAPrn) in a weight ratio of 1:0.03 (=cgDBCz The light-emitting layer 113 was formed by co-evaporation of 25 nm of PA: 1,6mMemFLPAPrn). Formed.

[0412] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 10 nm, and then Bathophenanthroline (abbreviation: BPhen) represented by the above structural formula (v) was The electron transport layer 114 was formed by vapor deposition so as to form the electron transport layer 114.

[0413] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. Then, aluminum is evaporated to a thickness of 200 nm. The cathode 102 was formed by deposition, and the light-emitting device 1 of this example was fabricated.

[0414] (How to create light-emitting element 2) The light-emitting element 2 is the light-emitting element 1 in which cgDBCzPA in the electron transport layer 114 is replaced with cgDBCzPA having the above structural formula (v i) 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl] Dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II) 2,9-bis(naphthalene-2-yl)-4,7-diamine represented by the above structural formula (vii) The light-emitting element was changed to phenyl-1,10-phenanthroline (abbreviation: NBPhen). It was prepared in the same manner as 1.

[0415] The device structures of the light-emitting elements 1 and 2 are summarized in the table below.

[0416] [Table 1]

[0417] The light-emitting element 1 and the light-emitting element 2 were placed in a glove box with a nitrogen atmosphere. The process of sealing with a glass substrate to prevent exposure to the atmosphere (applying a sealant around the element) After the UV treatment during sealing and heat treatment at 80°C for 1 hour, the initial characteristics of these light-emitting devices were The measurements were carried out at room temperature (in an atmosphere maintained at 25°C).

[0418] FIG. 28 shows the luminance-current density characteristics of Light-emitting Elements 1 and 2, and FIG. 29 shows the current efficiency-luminance characteristics of Light-emitting Elements 1 and 2. 29, the brightness-voltage characteristics are shown in Fig. 30, the current-voltage characteristics are shown in Fig. 31, and the external quantum efficiency-brightness characteristics are shown in Fig. 32. The properties are shown in FIG. 32 and the emission spectrum in FIG.

[0419] [Table 2]

[0420] 28 to 33 and Table 2, the light-emitting element 1 has a luminance of 1000 cd / m 2 External quantum effects in The luminance of light-emitting element 2 is 1000 cd / m 2 The external quantum efficiency at The results showed positive results.

[0421] In addition, the current value was set to 2 mA, and the change in brightness with respect to the driving time under the condition of a constant current density was 34 shows a graph representing the above. As shown in FIG. 34, the light-emitting element 1 and the light-emitting element 2 were Even after 0 hours of operation, the brightness remains at 90% or more of the initial brightness, and there is no sign of brightness decreasing with the accumulated operating time. The drop was very small, and it was found to be a light-emitting element with a good lifespan. [Example]

[0422] In this example, the light-emitting elements 3 and 4 according to one embodiment of the present invention described in the embodiment will be described. The structural formulae of the organic compounds used in the light-emitting elements 3 and 4 are shown below.

[0423] [ka]

[0424] (Method for manufacturing light-emitting element 3) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The anode 101 was formed by a film deposition method. The film thickness was 70 nm and the electrode area was 4 mm 2 (2mm x 2mm).

[0425] 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.

[0426] 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.

[0427] Next, the substrate on which the anode 101 is formed is placed in a vacuum chamber so that the surface on which the anode 101 is formed faces downward. The substrate was fixed to a substrate holder installed in the vacuum evaporation device, and evaporation was performed on the anode 101 using resistance heating. The 2,3,6,7,10,11-hexacyano-1-methyl-1-methyl-2-methyl-1 ... ,4,5,8,9,12-Hexaazatriphenylene (abbreviation: HAT-CN) was evaporated to a thickness of 5 nm. The hole injection layer 111 was formed by deposition.

[0428] Next, on the hole injection layer 111, 4,4'-bis[N-(1 -naphthyl-N-phenylamino]biphenyl (abbreviation: NPB) to a thickness of 10 nm. After vapor deposition as shown in the above structural formula (101), 4-(6;2'-binaphthyl-2 -yl)-4',4''-diphenyltriphenylamine (abbreviation: BBA(βN2)B) Then, 3,6-bis[4-(2- naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviation: βNP2PC) A hole transport layer 112 was formed by vapor deposition to a thickness of 0 nm.

[0429] Next, 7-[4-(10-phenyl-9-anthracene)-2-methyl-2-(2-methyl-1,2-diphenyl- ... (phenyl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) N,N'-bis(3-methylphenyl)-N ... [3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diazo 1,6mMemFLPAPrn) in a weight ratio of 1:0.03 (=cgDBCz The light-emitting layer 113 was formed by co-evaporation of 25 nm of PA: 1,6mMemFLPAPrn). Formed.

[0430] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 10 nm, and then Bathophenanthroline (abbreviation: BPhen) represented by the above structural formula (v) was The electron transport layer 114 was formed by vapor deposition so as to form the electron transport layer 114.

[0431] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. Then, aluminum is evaporated to a thickness of 200 nm. The cathode 102 was formed by deposition, and the light-emitting device 3 of this example was fabricated.

[0432] (How to make light-emitting element 4) The light-emitting element 4 is the light-emitting element 3 in which cgDBCzPA in the electron transport layer 114 is replaced with a compound represented by the above structural formula (v i) 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl] Dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II) 2,9-bis(naphthalene-2-yl)-4,7-diamine represented by the above structural formula (vii) The light-emitting element was changed to phenyl-1,10-phenanthroline (abbreviation: NBPhen). It was prepared in the same manner as in 3.

[0433] The device structures of the light-emitting elements 3 and 4 are summarized in the table below.

[0434] [Table 3]

[0435] The light emitting element 3 and the light emitting element 4 were placed in a glove box with a nitrogen atmosphere. The process of sealing with a glass substrate to prevent exposure to the atmosphere (applying a sealant around the element) After the UV treatment during sealing and heat treatment at 80°C for 1 hour, the initial characteristics of these light-emitting devices were The measurements were carried out at room temperature (in an atmosphere maintained at 25°C).

[0436] FIG. 35 shows the luminance-current density characteristics of the light-emitting elements 3 and 4, and FIG. 36 shows the current efficiency-luminance characteristics of the light-emitting elements 3 and 4. 36, brightness-voltage characteristics are shown in Fig. 37, current-voltage characteristics are shown in Fig. 38, and external quantum efficiency-brightness characteristics are shown in Fig. 39. The properties are shown in FIG. 39 and the emission spectrum in FIG.

[0437] [Table 4]

[0438] 35 to 40 and Table 4, the light-emitting element 3 has a luminance of 1000 cd / m 2 External quantum effects in The efficiency is 12%, and light-emitting element 4 is 1000 cd / m 2 The external quantum efficiency at The results showed positive results.

[0439] In addition, the current value was set to 2 mA, and the change in brightness with respect to the driving time under the condition of a constant current density was 41 shows a graph representing the above. As shown in FIG. 41, the light-emitting element 3 and the light-emitting element 4 are Even after 0 hours of operation, the brightness remains at 90% or more of the initial brightness, and there is no sign of brightness decreasing with the accumulated operating time. The drop was very small, and it was found to be a light-emitting element with a good lifespan. [Example]

[0440] In this example, the light-emitting elements 5 and 6 according to one embodiment of the present invention described in the embodiment will be described. The structural formulae of the organic compounds used in the light-emitting elements 5 and 6 are shown below.

[0441] [ka]

[0442] (Method for manufacturing light-emitting element 5) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The anode 101 was formed by a film deposition method. The film thickness was 70 nm and the electrode area was 4 mm 2 (2mm x 2mm).

[0443] 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.

[0444] 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.

[0445] Next, the substrate on which the anode 101 is formed is placed in a vacuum chamber so that the surface on which the anode 101 is formed faces downward. The substrate was fixed to a substrate holder installed in the vacuum evaporation device, and evaporation was performed on the anode 101 using resistance heating. The 2,3,6,7,10,11-hexacyano-1-methyl-1-methyl-2-methyl-1 ... ,4,5,8,9,12-Hexaazatriphenylene (abbreviation: HAT-CN) was evaporated to a thickness of 5 nm. The hole injection layer 111 was formed by deposition.

[0446] Next, on the hole injection layer 111, 4,4'-bis[N-(1 -naphthyl-N-phenylamino]biphenyl (abbreviation: NPB) to a thickness of 10 nm. After vapor deposition as shown above, N,N-bis(4-biphenylyl) )-2,2'-binaphthyl-6-amine (abbreviation: BBA(βN2)) was evaporated to a thickness of 10 nm, Furthermore, 3,6-bis[4-(2-naphthyl)phenyl]-2-methyl-2-naphthyl-2-phenyl-2-methyl ... ]-9-phenyl-9H-carbazole (abbreviation: βNP2PC) was evaporated to 10 nm. A transport layer 112 was formed.

[0447] Next, 7-[4-(10-phenyl-9-anthracene)-2-methyl-2-(2-methyl-1,2-diphenyl- ... (phenyl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) N,N'-bis(3-methylphenyl)-N ... [3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diazo 1,6mMemFLPAPrn) in a weight ratio of 1:0.03 (=cgDBCz The light-emitting layer 113 was formed by co-evaporation of 25 nm of PA: 1,6mMemFLPAPrn). Formed.

[0448] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 10 nm, and then Bathophenanthroline (abbreviation: BPhen) represented by the above structural formula (v) was The electron transport layer 114 was formed by vapor deposition so as to form the electron transport layer 114.

[0449] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. Then, aluminum is evaporated to a thickness of 200 nm. The cathode 102 was formed by deposition, and the light-emitting device 5 of this example was fabricated.

[0450] (How to create light-emitting element 6) The light-emitting element 6 is the light-emitting element 5 in which cgDBCzPA in the electron transport layer 114 is replaced with a compound represented by the above structural formula (v i) 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl] Dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II) 2,9-bis(naphthalene-2-yl)-4,7-diamine represented by the above structural formula (vii) The light-emitting element was changed to phenyl-1,10-phenanthroline (abbreviation: NBPhen). It was prepared in the same manner as 5.

[0451] The device structures of the light-emitting elements 5 and 6 are summarized in the table below.

[0452] [Table 5]

[0453] The light emitting element 5 and the light emitting element 6 are placed in a glove box with a nitrogen atmosphere. The process of sealing with a glass substrate to prevent exposure to the atmosphere (applying a sealant around the element) After the UV treatment during sealing and heat treatment at 80°C for 1 hour, the initial characteristics of these light-emitting devices were The measurements were carried out at room temperature (in an atmosphere maintained at 25°C).

[0454] FIG. 42 shows the luminance-current density characteristics of the light-emitting elements 5 and 6, and FIG. 43 shows the current efficiency-luminance characteristics of the light-emitting elements 5 and 6. 43, the luminance-voltage characteristics are shown in Fig. 44, the current-voltage characteristics are shown in Fig. 45, and the external quantum efficiency-luminance characteristics are shown in Fig. 46. The properties are shown in FIG. 46 and the emission spectrum in FIG.

[0455] [Table 6]

[0456] 42 to 47 and Table 6, the light-emitting element 5 has a luminance of 1000 cd / m 2 External quantum effects in The luminance of light-emitting element 6 is 1000 cd / m 2 The external quantum efficiency at 12% showed good results.

[0457] In addition, the current value was set to 2 mA, and the change in brightness with respect to the driving time under the condition of a constant current density was 48 shows a graph representing the above. As shown in FIG. 48, the light-emitting element 5 and the light-emitting element 6 are Even after 0 hours of operation, the brightness remains at 90% or more of the initial brightness, and there is no sign of brightness decreasing with the accumulated operating time. The drop was very small, and it was found to be a light-emitting element with a good lifespan. [Example]

[0458] In this example, the light-emitting elements 7 and 8 according to one embodiment of the present invention described in the embodiment will be described. The structural formulae of the organic compounds used in the light-emitting elements 7 and 8 are shown below.

[0459] [ka]

[0460] (Method for manufacturing light-emitting element 7) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The anode 101 was formed by a film deposition method. The film thickness was 70 nm and the electrode area was 4 mm 2 (2mm x 2mm).

[0461] 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.

[0462] 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.

[0463] Next, the substrate on which the anode 101 is formed is placed in a vacuum chamber so that the surface on which the anode 101 is formed faces downward. The substrate was fixed to a substrate holder installed in the vacuum evaporation device, and evaporation was performed on the anode 101 using resistance heating. The 2,3,6,7,10,11-hexacyano-1-methyl-1-methyl-2-methyl-1 ... ,4,5,8,9,12-Hexaazatriphenylene (abbreviation: HAT-CN) was evaporated to a thickness of 5 nm. The hole injection layer 111 was formed by deposition.

[0464] Next, on the hole injection layer 111, 4,4'-bis[N-(1 -naphthyl-N-phenylamino]biphenyl (abbreviation: NPB) to a thickness of 20 nm. After vapor deposition as shown in the above structural formula (116), 4-(3;2'-binaphthyl-2 -yl)-4',4''-diphenyltriphenylamine (abbreviation: BBA(βN2)B- 02) was evaporated to a thickness of 10 nm to form a hole transport layer 112.

[0465] Next, 7-[4-(10-phenyl-9-anthracene)-2-methyl-2-(2-methyl-1,2-diphenyl- ... (phenyl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) N,N'-bis(3-methylphenyl)-N ... [3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diazo 1,6mMemFLPAPrn) in a weight ratio of 1:0.03 (=cgDBCz The light-emitting layer 113 was formed by co-evaporation of 25 nm of PA: 1,6mMemFLPAPrn). Formed.

[0466] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 15 nm, and then Bathophenanthroline (abbreviation: BPhen) represented by the above structural formula (v) was The electron transport layer 114 was formed by vapor deposition so as to form the electron transport layer 114.

[0467] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. Then, aluminum is evaporated to a thickness of 200 nm. The cathode 102 was formed by deposition, and the light-emitting device 7 of this example was fabricated.

[0468] (How to make light-emitting element 8) The light-emitting element 8 is the light-emitting element 7, in which the cgDBCzPA in the electron transport layer 114 is replaced with the compound represented by the above structural formula (v i) 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl] Dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II) was used, and the film thickness was BPhen was replaced with 2,9-bis(naphthalene) represented by the above structural formula (vii). phthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NB The film thickness was 15 nm. .

[0469] The device structures of the light-emitting elements 7 and 8 are summarized in the table below.

[0470] [Table 7]

[0471] The light emitting element 7 and the light emitting element 8 are placed in a glove box with a nitrogen atmosphere. The process of sealing with a glass substrate to prevent exposure to the atmosphere (applying a sealant around the element) After the UV treatment during sealing and heat treatment at 80°C for 1 hour, the initial characteristics of these light-emitting devices were The measurements were carried out at room temperature (in an atmosphere maintained at 25°C).

[0472] The luminance-current density characteristics of the light-emitting elements 7 and 8 are shown in FIG. 49, and the current efficiency-luminance characteristics are shown in FIG. 50, the brightness-voltage characteristics are shown in Fig. 51, the current-voltage characteristics are shown in Fig. 52, and the external quantum efficiency-brightness characteristics are shown in Fig. 53. The properties are shown in FIG. 53 and the emission spectrum in FIG.

[0473] [Table 8]

[0474] 49 to 54 and Table 8, the light-emitting element 7 has a luminance of 1000 cd / m 2 External quantum effects in The luminance of light-emitting element 8 is 1000 cd / m 2 The external quantum efficiency at showed good results. [Example]

[0475] In this example, the light-emitting elements 9 and 10 according to one embodiment of the present invention described in the embodiment The structural formulas of the organic compounds used in the light-emitting elements 9 and 10 are shown below. vinegar.

[0476] [ka]

[0477] (Method for manufacturing light-emitting element 9) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The anode 101 was formed by a film deposition method. The film thickness was 70 nm and the electrode area was 4 mm 2 (2mm x 2mm).

[0478] 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.

[0479] 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.

[0480] Next, the substrate on which the anode 101 is formed is placed in a vacuum chamber so that the surface on which the anode 101 is formed faces downward. The substrate was fixed to a substrate holder installed in the vacuum evaporation device, and evaporation was performed on the anode 101 using resistance heating. The 2,3,6,7,10,11-hexacyano-1-methyl-1-methyl-2-methyl-1 ... ,4,5,8,9,12-Hexaazatriphenylene (abbreviation: HAT-CN) was evaporated to a thickness of 5 nm. The hole injection layer 111 was formed by deposition.

[0481] Next, on the hole injection layer 111, 4,4'-bis[N-(1 -naphthyl-N-phenylamino]biphenyl (abbreviation: NPB) to a thickness of 10 nm. After vapor deposition as shown in the above structural formula (116), 4-(3;2'-binaphthyl-2 -yl)-4',4''-diphenyltriphenylamine (abbreviation: BBA(βN2)B- 02) was evaporated to 10 nm, and then 3,6-bis[4- (2-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviation: βNP2PC ) was evaporated to a thickness of 10 nm to form a hole transport layer 112.

[0482] Next, 7-[4-(10-phenyl-9-anthracene)-2-methyl-2-(2-methyl-1,2-diphenyl- ... (phenyl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) N,N'-bis(3-methylphenyl)-N ... [3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diazo 1,6mMemFLPAPrn) in a weight ratio of 1:0.03 (=cgDBCz The light-emitting layer 113 was formed by co-evaporation of 25 nm of PA: 1,6mMemFLPAPrn). Formed.

[0483] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 15 nm, and then Bathophenanthroline (abbreviation: BPhen) represented by the above structural formula (v) was The electron transport layer 114 was formed by vapor deposition so as to form the electron transport layer 114.

[0484] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. Then, aluminum is evaporated to a thickness of 200 nm. The cathode 102 was formed by deposition, and the light-emitting device 9 of this example was fabricated.

[0485] (Method of making light-emitting element 10) The light-emitting element 10 is the light-emitting element 9, in which the cgDBCzPA in the electron transport layer 114 is a compound represented by the above structural formula ( 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl] represented by vi) ]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq‐II) The diameter was set to 10 nm. BPhen was replaced with 2,9-bis( Naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: N The film thickness was changed to 15 nm. Ta.

[0486] The device structures of the light-emitting elements 9 and 10 are summarized in the table below.

[0487] [Table 9]

[0488] The light emitting elements 9 and 10 were placed in a glove box with a nitrogen atmosphere. The process of sealing the device with a glass substrate to prevent it from being exposed to the atmosphere (sealing material is applied around the device After UV treatment during sealing and heat treatment at 80°C for 1 hour, the initial characteristics of these light-emitting devices were The measurements were carried out at room temperature (in an atmosphere maintained at 25°C).

[0489] The luminance-current density characteristics of the light-emitting elements 9 and 10 are shown in FIG. 55, and the current efficiency-luminance characteristics are shown in FIG. Figure 56 shows the brightness-voltage characteristics, Figure 57 shows the current-voltage characteristics, and Figure 58 shows the external quantum efficiency-brightness The characteristics are shown in FIG. 59, and the emission spectrum is shown in FIG.

[0490] [Table 10]

[0491] 55 to 60 and Table 10, the light-emitting element 9 has a luminance of 1000 cd / m 2 External quantum in Efficiency is 12%, and light emitting element 10 is 1000 cd / m 2 The external quantum efficiency at The results were very good. [Example]

[0492] In this example, the light-emitting elements 11 and 12 according to one embodiment of the present invention described in the embodiment The structural formulas of the organic compounds used in the light-emitting elements 11 and 12 are as follows: Shown below.

[0493] [ka]

[0494] (Method for manufacturing light-emitting element 11) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The anode 101 was formed by a film deposition method. The film thickness was 70 nm and the electrode area was 4 mm 2 (2mm x 2mm).

[0495] 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.

[0496] 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.

[0497] Next, the substrate on which the anode 101 is formed is placed in a vacuum chamber so that the surface on which the anode 101 is formed faces downward. The substrate was fixed to a substrate holder installed in the vacuum evaporation device, and evaporation was performed on the anode 101 using resistance heating. The 2,3,6,7,10,11-hexacyano-1-methyl-1-methyl-2-methyl-1 ... ,4,5,8,9,12-Hexaazatriphenylene (abbreviation: HAT-CN) was evaporated to a thickness of 5 nm. The hole injection layer 111 was formed by deposition.

[0498] Next, on the hole injection layer 111, 4,4'-bis[N-(1 -naphthyl-N-phenylamino]biphenyl (abbreviation: NPB) to a thickness of 20 nm. After vapor deposition as shown in the above structural formula (117), 4-(2;1'-binaphthyl-3 -yl)-4',4''-diphenyltriphenylamine (abbreviation: BBAαNβNB-0 2) was evaporated to a thickness of 10 nm to form a hole transport layer 112.

[0499] Next, 7-[4-(10-phenyl-9-anthracene)-2-methyl-2-(2-methyl-1,2-diphenyl- ... (phenyl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) N,N'-bis(3-methylphenyl)-N ... [3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diazo 1,6mMemFLPAPrn) in a weight ratio of 1:0.03 (=cgDBCz The light-emitting layer 113 was formed by co-evaporation of 25 nm of PA: 1,6mMemFLPAPrn). Formed.

[0500] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 15 nm, and then Bathophenanthroline (abbreviation: BPhen) represented by the above structural formula (v) was The electron transport layer 114 was formed by vapor deposition so as to form the electron transport layer 114.

[0501] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. Then, aluminum is evaporated to a thickness of 200 nm. The cathode 102 was formed by deposition, and the light emitting device 11 of this example was fabricated.

[0502] (Method of making light-emitting element 12) The light-emitting element 12 is obtained by replacing the cgDBCzPA in the electron transport layer 114 of the light-emitting element 11 with the compound represented by the above structural formula: 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]biphenyl-3-yl 2mDBTBPDBq‐II) The thickness was set to 10 nm. BPhen was replaced with 2,9-bis(2,9-diphenyl ether) represented by the above structural formula (vii). (Naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: The film thickness was changed to 15 nm. Other than these, the light-emitting element was fabricated in the same manner as light-emitting element 11. did.

[0503] The device structures of the light-emitting elements 11 and 12 are summarized in the table below.

[0504] [Table 11]

[0505] The light emitting elements 11 and 12 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 initial stage of these light-emitting devices, The characteristics were measured at room temperature (in an atmosphere maintained at 25°C).

[0506] The luminance-current density characteristics of the light-emitting elements 11 and 12 are shown in FIG. 61, and the current efficiency-luminance characteristics are shown in FIG. The brightness-voltage characteristics are shown in Figure 62, the current-voltage characteristics are shown in Figure 64, and the external quantum efficiency-brightness The optical characteristics are shown in FIG. 65, and the emission spectrum is shown in FIG.

[0507] [Table 12]

[0508] 61 to 66 and Table 12, the light emitting element 11 has a luminance of 1000 cd / m 2 External quantity in The light emitting efficiency is 12%, and the light emitting element 12 is 1000 cd / m 2 The external quantum efficiency is 13% The results showed that: [Example]

[0509] In this example, the light-emitting elements 13 and 14 according to one embodiment of the present invention described in the embodiment The structural formulas of the organic compounds used in the light-emitting elements 13 and 14 are as follows: Shown below.

[0510] [ka]

[0511] (Method for manufacturing light-emitting element 13) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The anode 101 was formed by a film deposition method. The film thickness was 70 nm and the electrode area was 4 mm 2 (2mm x 2mm).

[0512] 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.

[0513] 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.

[0514] Next, the substrate on which the anode 101 is formed is placed in a vacuum chamber so that the surface on which the anode 101 is formed faces downward. The substrate was fixed to a substrate holder installed in the vacuum evaporation device, and evaporation was performed on the anode 101 using resistance heating. The 2,3,6,7,10,11-hexacyano-1-methyl-1-methyl-2-methyl-1 ... ,4,5,8,9,12-Hexaazatriphenylene (abbreviation: HAT-CN) was evaporated to a thickness of 5 nm. The hole injection layer 111 was formed by deposition.

[0515] Next, on the hole injection layer 111, 4,4'-bis[N-(1 -naphthyl-N-phenylamino]biphenyl (abbreviation: NPB) to a thickness of 10 nm. After vapor deposition as shown in the above structural formula (117), 4-(2;1'-binaphthyl-3 -yl)-4',4''-diphenyltriphenylamine (abbreviation: BBAαNβNB-0 2) was evaporated to a thickness of 10 nm, and then 3,6-bis[4-( 2-Naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviation: βNP2PC) was evaporated to a thickness of 10 nm to form a hole transport layer 112.

[0516] Next, 7-[4-(10-phenyl-9-anthracene)-2-methyl-2-(2-methyl-1,2-diphenyl- ... (phenyl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) N,N'-bis(3-methylphenyl)-N ... [3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diazo 1,6mMemFLPAPrn) in a weight ratio of 1:0.03 (=cgDBCz The light-emitting layer 113 was formed by co-evaporation of 25 nm of PA: 1,6mMemFLPAPrn). Formed.

[0517] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 15 nm, and then Bathophenanthroline (abbreviation: BPhen) represented by the above structural formula (v) was The electron transport layer 114 was formed by vapor deposition so as to form the electron transport layer 114.

[0518] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. Then, aluminum is evaporated to a thickness of 200 nm. The cathode 102 was formed by deposition, and the light emitting device 13 of this example was fabricated.

[0519] (Method of making light-emitting element 14) The light-emitting element 14 is obtained by replacing the cgDBCzPA in the electron transport layer 114 of the light-emitting element 13 with the compound represented by the above structural formula: 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]biphenyl-3-yl 2mDBTBPDBq‐II) The thickness was set to 10 nm. BPhen was replaced with 2,9-bis(2,9-diphenyl ether) represented by the above structural formula (vii). (Naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: The film thickness was changed to 15 nm. Other than these, the light-emitting device was fabricated in the same manner as light-emitting device 13. did.

[0520] The device structures of the light-emitting devices 13 and 14 are summarized in the table below.

[0521] [Table 13]

[0522] The light emitting elements 13 and 14 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 were measured at room temperature (in an atmosphere maintained at 25°C).

[0523] The luminance-current density characteristics of the light-emitting elements 13 and 14 are shown in FIG. 67, and the current efficiency-luminance characteristics are shown in FIG. The luminance-voltage characteristics are shown in Figure 68, the current-voltage characteristics are shown in Figure 70, and the external quantum efficiency-luminance characteristics are shown in Figure 71. The optical characteristics are shown in FIG. 71, and the emission spectrum is shown in FIG.

[0524] [Table 14]

[0525] 67 to 72 and Table 14, the light emitting element 13 has a luminance of 1000 cd / m 2 External quantity in The light emitting efficiency is 12%, and the light emitting element 14 is 1000 cd / m 2 The external quantum efficiency is 13% The results were very good. [Example]

[0526] (Synthesis Example 8) In this synthesis example, the organic compound of the present invention shown in the structural formula (118) in the first embodiment 4-(1;2'-binaphthyl-4-yl)-4',4''-diphenyltriphenyl ether The synthesis method of BBAβNαNB is explained in detail. The structural formula of αNB is shown below.

[0527] [ka]

[0528] Step 1: 4,4'-diphenyl-4''-(4,4,5,5-tetramethyl-1, Synthesis of 3,2-dioxaborolan-2-yltriphenylamine 4,4'-Diphenyl-4''-(4,4,5,5-tetramethyl-1,3,2-dioxa (Saborolan-2-yl)triphenylamine was synthesized in the same manner as in Step 2 of Synthesis Example 1.

[0529] Step 2: 4-(1;2'-binaphthyl-4-yl)-4',4''-diphenyl Synthesis of triphenylamine (abbreviation: BBAβNαNB) 2.5 g (4.6 mmol) of 4,4'-diphenyl-4''-(4,4,5,5-tetramethyl- (tetramethyl-1,3,2-dioxaborolan-2-yl)triphenylamine, 1.5 g (4.6 mmol) of 1-bromo-4,2'-binaphthyl and 28 mg (92 μmol) of tri(ortho-tolyl)phosphine and 20 mL of (2.0 mol / L) potassium carbonate. The ethanol solution, 50 mL of toluene, and 10 mL of ethanol were added to a 200 mL flask equipped with a reflux condenser. The mixture was placed in a three-necked flask, degassed under reduced pressure, and then the atmosphere in the flask was replaced with nitrogen. After heating at 100°C, 10 mg (46 μmol) of palladium (II) acetate was added. The mixture was stirred for 3 hours. After stirring, the precipitated solid was collected by suction filtration. Water was added to the obtained filtrate. After separating the aqueous and organic layers, the aqueous layer was extracted with toluene. The mixture was washed with saturated saline and dried over magnesium sulfate. The filtrate was concentrated to give 1.5 g of a pale black solid, the target product, in a yield of 50%. The synthesis scheme of TOP2 is shown below.

[0530] [ka]

[0531] The obtained solid 1 The 1 H NMR chart is shown in Figure 75, and the numerical data is shown below. 1 H NMR (chloroform-d, 500 MHz): δ = 8.12 (d, J = 8.0 Hz , 1H), 7.99-7.91(m, 5H), 7.66(dd, J1=8.0Hz, J2 =1.5Hz, 1H), 7.62-7.52(m, 12H), 7.50-7.48(m, 3H), 7.46-7.41(m, 5H), 7.33-7.28(m, 8H)

[0532] The resulting 1.5 g of solid was purified by train sublimation. The conditions were argon flow rate 15 mL / min, pressure 3.6 Pa, and heating at 310°C for 15 hours. After purification by sublimation, 1.1 g of the target pale yellow solid was obtained with a recovery rate of 73%.

[0533] Next, the absorption and emission spectra of the toluene solution of BBAβNαNB were measured. The results of the measurement of the absorption spectrum and emission spectrum of the thin film are shown below. The sample preparation method, measurement method, and measurement device are the same as those shown in the examples, so the explanation is omitted. Abbreviated.

[0534] From the measurement results, the toluene solution of BBAβNαNB showed an absorption peak around 348 nm. The peak emission wavelength was 430 nm (excitation wavelength 348 nm). The NB thin film exhibits absorption peaks around 351 nm, 300 nm, 245 nm, and 215 nm. The peak emission wavelength was observed at 439 nm (excitation wavelength 353 nm). It was confirmed that B emitted blue light. The compound of one embodiment of the present invention is a luminescent material or a fluorescent material in the visible region. It can also be used as a host for luminescent materials.

[0535] Furthermore, thin films of BBAβNαNB are resistant to aggregation even in the atmosphere and show little change in their morphology. The film quality was found to be good.

[0536] The HOMO and LUMO levels of BBAβNαNB were measured by cyclic voltammetry (C The CV measurement was repeated 100 times, and the value at the 100th cycle was calculated. The oxidation-reduction wave in the measurement was compared with the oxidation-reduction wave in the first cycle to determine the electrical stability of the compound. The methods used for these were the same as in Example 1, so the description will be omitted.

[0537] As a result, in the measurement of the oxidation potential Ea [V] of BBAβNαNB, the HOMO level was -5 The LUMO level was found to be -2.40 eV. In addition, in repeated measurements of the oxidation-reduction wave, the wave after the first cycle and the 100th cycle When compared with the shape, the peak intensity remained at 91% in the Ea measurement. It was confirmed that BAβNαNB has very good resistance to oxidation.

[0538] Furthermore, thermogravimetry-differential thermal analysis (TDMA) of BBAβNαNB was performed. The measurement was carried out using a high-precision thermal analysis (Takamatsu Thermal Analysis). Empty differential thermobalance (Bruker AXS, TG-DTA2410S) The measurement was carried out at atmospheric pressure, with a temperature rise rate of 10°C / min, under a nitrogen gas flow (flow rate 2 The thermogravimetric and differential thermal analysis was carried out under the condition of 0.00 mL / min. The temperature at which the weight of the sample becomes -5% of the weight at the start of measurement (decomposition temperature) is 462°C. It was shown that this material has excellent heat resistance.

[0539] Differential scanning calorimetry (DSC) of BBAβNαNB was performed using a PerkinElmer The differential scanning calorimetry was performed using a Pyris1DSC at a heating rate of 40°C / min. After heating from -10°C to 320°C, the sample was kept at the same temperature for 1 minute and then cooled at a rate of 100°C. Cool to -10°C at ℃ / min, then hold at -10°C for 3 minutes. Repeat this process twice. The glass transition temperature of BBAβNαNB was It was found that the compound had a high heat resistance of 123°C. . [Example]

[0540] (Synthesis Example 9) In this synthesis example, 4-(1;2'-binaphthalene)-4-(1, ... (5-yl)-4',4''-diphenyltriphenylamine (abbreviation: BBAβNαN The synthesis method of BBAβNαNB-02 is explained below. The structural formula of BBAβNαNB-02 is shown below. .

[0541] [ka]

[0542] Step 1: 4,4'-diphenyl-4''-(4,4,5,5-tetramethyl-1, Synthesis of 3,2-dioxaborolan-2-yltriphenylamine 4,4'-Diphenyl-4''-(4,4,5,5-tetramethyl-1,3,2-dioxa (Saborolan-2-yl)triphenylamine was synthesized in the same manner as in Step 2 of Synthesis Example 1.

[0543] Step 2: 4-(1,2'-binaphthyl-5-yl)-4',4''-diphenyl Synthesis of triphenylamine (abbreviation: BBAβNαNB-02) 2.5 g (4.6 mmol) of 4,4'-diphenyl-4''-(4,4,5,5-tetramethyl- (tetramethyl-1,3,2-dioxaborolan-2-yl)triphenylamine, 1.5 g (4.6 mmol) of 5-bromo-1,2'-binaphthyl and 28 mg (92 μmol) of tri(ortho-tolyl)phosphine and 20 mL of (2.0 mol / L) potassium carbonate. The ethanol solution, 50 mL of toluene, and 10 mL of ethanol were added to a 200 mL flask equipped with a reflux condenser. The mixture was placed in a three-necked flask, degassed under reduced pressure, and then the atmosphere in the flask was replaced with nitrogen. After heating at 100°C, 10 mg (46 μmol) of palladium (II) acetate was added. The mixture was stirred for 9 hours. After stirring, the precipitated solid was collected by suction filtration. Water was added to the obtained filtrate. The organic layer and the aqueous layer were separated, and the aqueous layer was extracted with toluene. The combined layers were washed with water and saturated brine, and then dried over magnesium sulfate. The filtrate was concentrated to give 1.6 g of a white solid in a yield of 53%. The synthesis scheme for Step 2 is shown below.

[0544] [ka]

[0545] The obtained solid 1 The 1 H NMR chart is shown in Figure 76, and the numerical data is shown below. 1 H NMR (chloroform-d, 500 MHz): δ = 8.10 (dd, J = 7.0 Hz, J2=2.5Hz, 1H), 8.00-7.92(m, 5H), 7.67(dd, J1=8.0Hz, J2=1.5Hz, 1H), 7.64-7.62(m, 4H), 7. 59(d, J=8.5Hz, 4H), 7.57-7.55(m, 4H), 7.51-7. 43(m, 8H), 7.35-7.31(m, 8H)

[0546] The resulting solid (1.6 g) was purified by train sublimation. The conditions were argon flow rate 15 mL / min, pressure 3.6 Pa, and heating at 310°C for 15 hours. After purification by sublimation, 1.3 g of the target pale yellow solid was obtained with a recovery rate of 81%.

[0547] Next, the absorption and emission spectra of the toluene solution of BBAβNαNB-02 were measured. The measurement results and the absorption and emission spectra of the thin film are shown below. The sample preparation method, measurement method, and measurement device are the same as those shown in the examples, so the explanation will be omitted. is omitted.

[0548] From the measurement results, the toluene solution of BBAβNαNB-02 has an absorption peak around 346 nm. The peak emission wavelength was 419 nm (excitation wavelength 348 nm). βNαNB-02 thin film absorbs light around 350nm, 300nm, 243nm, and 215nm A peak was observed at an emission wavelength of 427 nm (excitation wavelength 350 nm). It was confirmed that BBAβNαNB-02 emitted blue light. The compound can also be used as a host for luminescent materials and fluorescent materials that emit light in the visible range.

[0549] In addition, thin films of BBAβNαNB-02 are resistant to aggregation even in the atmosphere and do not change in shape. It was found that the particles were small and the film quality was good.

[0550] The HOMO and LUMO levels of BBAβNαNB-02 were measured by cyclic voltammetry. The calculation was based on the CV measurement. The CV measurement was repeated 100 times and the The oxidation-reduction wave in the first measurement is compared with the oxidation-reduction wave in the first cycle to determine the electrical conductivity of the compound. The methods for these were explained in Example 1, so the description is omitted here. .

[0551] As a result, in the measurement of the oxidation potential Ea [V] of BBAβNαNB-02, the HOMO level The LUMO level was found to be -5.49 eV, while the LUMO level was found to be -2.35 eV. In addition, in the repeated measurement of the oxidation-reduction wave, the first cycle and the 100th cycle When compared with the waveform after the Ea measurement, it was found that 91% of the peak intensity was maintained. It was confirmed that BBAβNαNB-02 has very good resistance to oxidation.

[0552] In addition, thermogravimetry and differential thermal analysis (TTA) of BBAβNαNB-02 The measurement was carried out using differential thermal analysis (Y-Differential Thermal Analysis). The differential thermobalance was a high vacuum type (manufactured by Bruker AXS, TG-DTA24 The measurement was carried out at atmospheric pressure, with a temperature rise rate of 10°C / min, under a nitrogen gas flow ( The thermogravimetric and differential thermal analysis was carried out under the condition of a flow rate of 200 mL / min. The temperature at which the weight calculated from the above becomes -5% of the weight at the start of measurement (decomposition temperature) is 477°C. This indicates that the material has high heat resistance.

[0553] Differential scanning calorimetry (DSC) of BBAβNαNB-02 was performed using a PerkinElmer The differential scanning calorimetry was performed using a Pyris1 DSC manufactured by the company. The temperature was increased at a rate of 40°C / m After heating from -10°C to 330°C, the temperature was kept at the same temperature for 1 minute, and then the temperature was lowered at a Cool to -10°C at 100°C / min, then hold at -10°C for 3 minutes, repeating this cycle twice The results of the second measurement were used. The glass transition temperature was found to be 111°C, demonstrating that the compound has good heat resistance. It became clear. [Example]

[0554] In this example, the light-emitting elements 15 to 24 of one embodiment of the present invention described in the embodiment The structural formulas of the organic compounds used in the light-emitting elements 15 to 24 are shown below. vinegar.

[0555] [ka]

[0556] [ka]

[0557] (Method for manufacturing light-emitting element 15) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The anode 101 was formed by a film deposition method. The film thickness was 70 nm and the electrode area was 4 mm 2 (2mm x 2mm).

[0558] 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.

[0559] 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.

[0560] Next, the substrate on which the anode 101 is formed is placed in a vacuum chamber so that the surface on which the anode 101 is formed faces downward. The substrate was fixed to a substrate holder installed in the vacuum evaporation device, and evaporation was performed on the anode 101 using resistance heating. The 2,3,6,7,10,11-hexacyano-1-methyl-1-methyl-2-methyl-1 ... ,4,5,8,9,12-Hexaazatriphenylene (abbreviation: HAT-CN) was evaporated to a thickness of 5 nm. The hole injection layer 111 was formed by deposition.

[0561] Next, on the hole injection layer 111, 4,4'-bis[N-(1 -naphthyl-N-phenylamino]biphenyl (abbreviation: NPB) to a thickness of 10 nm. After vapor deposition as shown in the above structural formula (110), 4-(2;2'-binaphthyl-7 -yl)-4',4''-diphenyltriphenylamine (abbreviation: BBA(βN2)B- 03) was evaporated to 10 nm, and then 3,6-bis[4- (2-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviation: βNP2PC ) was evaporated to a thickness of 10 nm to form a hole transport layer 112.

[0562] Next, 7-[4-(10-phenyl-9-anthracene)-2-methyl-2-(2-methyl-1,2-diphenyl- ... (phenyl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) N,N'-bis(3-methylphenyl)-N ... [3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diazo 1,6mMemFLPAPrn) in a weight ratio of 1:0.03 (=cgDBCz The light-emitting layer 113 was formed by co-evaporation of 25 nm of PA: 1,6mMemFLPAPrn). Formed.

[0563] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 15 nm, and then Bathophenanthroline (abbreviation: BPhen) represented by the above structural formula (v) was The electron transport layer 114 was formed by vapor deposition so as to form the electron transport layer 114.

[0564] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. Then, aluminum is evaporated to a thickness of 200 nm. The cathode 102 was formed by deposition, and the light emitting device 15 of this example was fabricated.

[0565] (Method of making light-emitting element 16) The light-emitting element 16 is the light-emitting element 15, in which the electron transport layer 114 is a 2-[ 3'-(Dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]ky After forming 10 nm of noxaline (abbreviation: 2mDBTBPDBq-II), 2,9-bis (Naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: The light-emitting device was fabricated in the same manner as in Light-emitting device 15, except that NBPhen was vapor-deposited to a thickness of 15 nm.

[0566] (Method for manufacturing light-emitting element 17) The light-emitting element 17 has the same structure as the light-emitting element 15 except that the hole transport layer 112 is made of BBA(βN2)B-03. 4,4'-diphenyl-4''-(7;1'-binaphthalene) represented by the above structural formula (115) βNP 2PC is treated with 3,3'-(naphthalene-1,4-diyl)bis(2-methyl-1,4-diyl)benzoate represented by the above structural formula (ix). The electron transport The light-emitting device was fabricated in the same manner as the light-emitting device 15, except that BPhen in the transmission layer 114 was changed to NBPhen. Ta.

[0567] (Method for manufacturing light-emitting element 18) The light-emitting element 18 was fabricated by replacing the cgDBCzPA in the electron transport layer of the light-emitting element 17 with 2mDBTBP. The light-emitting device was fabricated in the same manner as Light-emitting Device 17, except that DBq-II was used.

[0568] (Method for manufacturing light-emitting element 19) The light-emitting element 19 is the same as the light-emitting element 17 except that the BBAαNβNB-03 in the hole transport layer has the above structure. 4-(2;1'-binaphthyl-6-yl)-4',4''-diphenyl ether represented by formula (114) The same as light-emitting element 17 except that the phenyltriphenylamine (abbreviation: BBAαNβNB) was used. It was made in.

[0569] (Method for manufacturing light-emitting element 20) The light-emitting element 20 has a structure similar to that of the light-emitting element 19, except that the electron transport layer 114 contains 2mDB of cgDBCzPA. The light-emitting device was fabricated in the same manner as in Light-emitting Device 19, except that TBPDBq-II was used instead.

[0570] (Method for manufacturing light-emitting element 21) The light-emitting element 21 is the same as the light-emitting element 17 except that the BBAαNβNB-03 in the hole transport layer 112 is 4-(1;2'-binaphthyl-4-yl)-4',4'' represented by the following structural formula (118): -Diphenyltriphenylamine (abbreviation: BBAβNαNB) was used, and the other light-emitting element 17 was prepared in the same manner as above.

[0571] (Method for manufacturing light-emitting element 22) The light-emitting element 22 is the same as the light-emitting element 21 except that the cgDBCzPA in the electron transport layer is replaced with 2mDBTBP The light-emitting device was fabricated in the same manner as the light-emitting device 21, except that DBq-II was used.

[0572] (Method for manufacturing light-emitting element 23) The light-emitting element 23 is the same as the light-emitting element 17 except that the BBAαNβNB-03 in the hole transport layer 112 is 4-(1;2'-binaphthyl-5-yl)-4',4'' represented by the following structural formula (120) -Diphenyltriphenylamine (abbreviation: BBAβNαNB-02) was used as the luminescent material. It was prepared in the same manner as child 17.

[0573] (Method for manufacturing light-emitting element 24) The light-emitting element 24 is the same as the light-emitting element 23 except that the electron transport layer 114 is made of cgDBCzPA and 2mDBT. The light-emitting device was fabricated in the same manner as in Light-emitting Device 23, except that BPDBq-II was used.

[0574] The device structures of the light-emitting devices 15 to 24 are summarized in the table below.

[0575] [Table 15]

[0576] [Table 16]

[0577] The light emitting elements 15 to 24 are placed in a glove box with a nitrogen atmosphere. The process of sealing the device with a glass substrate to prevent it from being exposed to the atmosphere (sealing material is applied around the device After UV treatment during sealing and heat treatment at 80°C for 1 hour, the initial characteristics of these light-emitting devices were The measurements were carried out at room temperature (in an atmosphere maintained at 25°C).

[0578] 1000 cd / m of light-emitting elements 15 to 24 2 The main characteristics of the area are listed in the table below. Shown below.

[0579] [Table 17]

[0580] From Table 17, light-emitting elements 15 to 24 have a luminance of 1000 cd / m 2 External quantities in the vicinity The photonic efficiency was 12% to 14%, which was a very good result. It is clear that the light-emitting elements 15 to 24 are light-emitting elements with excellent luminous efficiency.

[0581] In addition, the current value was set to 2mA, and the change in brightness with respect to the driving time under the condition of a constant current density was measured. The ratio (%) of the luminance after 100 hours to the initial luminance of each element is shown in the table below. vinegar.

[0582] [Table 18]

[0583] The light emitting elements 17 to 24 maintained 90% or more of the initial brightness even after 100 hours of operation. The light-emitting element 15 and the light-emitting element 16 maintained 85% or more of their initial luminance. The decrease in brightness due to the accumulation of driving time is very small, and it is clear that this is a light-emitting element with a long life. It was. [Example]

[0584] In this example, the light-emitting elements 25 to 34 of one embodiment of the present invention described in the embodiment The structural formulas of the organic compounds used in the light-emitting elements 25 to 34 are shown below. vinegar.

[0585] [ka]

[0586] [ka]

[0587] (Method for manufacturing light-emitting element 25) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The anode 101 was formed by a film deposition method. The film thickness was 70 nm and the electrode area was 4 mm 2 (2mm x 2mm).

[0588] 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.

[0589] 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.

[0590] Next, the substrate on which the anode 101 is formed is placed in a vacuum chamber so that the surface on which the anode 101 is formed faces downward. The substrate was fixed to a substrate holder installed in the vacuum evaporation device, and evaporation was performed on the anode 101 using resistance heating. The 2,3,6,7,10,11-hexacyano-1-methyl-1-methyl-2-methyl-1 ... ,4,5,8,9,12-Hexaazatriphenylene (abbreviation: HAT-CN) was evaporated to a thickness of 5 nm. The hole injection layer 111 was formed by deposition.

[0591] Next, on the hole injection layer 111, 4,4'-bis[N-(1 -naphthyl-N-phenylamino]biphenyl (abbreviation: NPB) to a thickness of 20 nm. After vapor deposition as shown in the above structural formula (110), 4-(2;2'-binaphthyl-7 -yl)-4',4''-diphenyltriphenylamine (abbreviation: BBA(βN2)B- 03) was evaporated to a thickness of 10 nm to form a hole transport layer 112.

[0592] Next, 7-[4-(10-phenyl-9-anthracene)-2-methyl-2-(2-methyl-1,2-diphenyl- ... (phenyl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) N,N'-bis(3-methylphenyl)-N ... [3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diazo 1,6mMemFLPAPrn) in a weight ratio of 1:0.03 (=cgDBCz The light-emitting layer 113 was formed by co-evaporation of 25 nm of PA: 1,6mMemFLPAPrn). Formed.

[0593] Then, cgDBCzPA was deposited on the light-emitting layer 113 to a thickness of 15 nm, and then Bathophenanthroline (abbreviation: BPhen) represented by the above structural formula (v) was The electron transport layer 114 was formed by vapor deposition so as to form the electron transport layer 114.

[0594] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. Then, aluminum is evaporated to a thickness of 200 nm. The cathode 102 was formed by deposition, and the light emitting device 25 of this example was fabricated.

[0595] (Method of making light-emitting element 26) The light-emitting element 26 is the light-emitting element 25, in which the electron transport layer 114 is a 2-[ 3'-(Dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]ky After forming 10 nm of noxaline (abbreviation: 2mDBTBPDBq-II), 2,9-bis (Naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: The light-emitting element was fabricated in the same manner as in Light-emitting element 25, except that NBPhen was deposited to a thickness of 15 nm.

[0596] (Method for manufacturing light-emitting element 27) The light-emitting element 27 has the same structure as the light-emitting element 25 except that the hole transport layer 112 is made of BBA(βN2)B-03. 4,4'-diphenyl-4''-(7;1'-binaphthalene) represented by the above structural formula (115) (2-ethyl-2-yl)triphenylamine (abbreviation: BBAαNβNB-03), and The light-emitting device was fabricated in the same manner as the light-emitting device 25, except that Bphen in the transmission layer 114 was changed to NBPhen.

[0597] (Method for manufacturing light-emitting element 28) The light-emitting element 28 has a structure in which the electron transport layer 114 of the light-emitting element 27 is made of cgDBCzPA at 2mDB. The light-emitting device was fabricated in the same manner as in Light-emitting Device 27, except that TBPDBq-II was used.

[0598] (Method for manufacturing light-emitting element 29) The light-emitting element 29 is obtained by replacing BBAαNβNB-03 in the light-emitting element 27 with the above structural formula (114) 4-(2;1'-binaphthyl-6-yl)-4',4''-diphenyltriphenyl ether represented by The light-emitting device was fabricated in the same manner as in Light-emitting Device 27, except that the organic solvent was changed to phenylamine (abbreviation: BBAαNβNB).

[0599] (Method for manufacturing the light-emitting element 30) The light-emitting device 30 is obtained by replacing BBAαNβNB-03 in the light-emitting device 28 with the compound represented by the above structural formula (114). 4-(2;1'-binaphthyl-6-yl)-4',4''-diphenyltriphenyl ether represented by The light-emitting device was fabricated in the same manner as in Light-emitting Device 28, except that the organic solvent was changed to butylamine (abbreviation: BBAαNβNB).

[0600] (Method for manufacturing light-emitting element 31) The light-emitting element 31 is obtained by replacing BBAαNβNB-03 in the light-emitting element 27 with the compound represented by the above structural formula (118). 4-(1;2'-binaphthyl-4-yl)-4',4''-diphenyltriphenyl ether The light-emitting device was fabricated in the same manner as in Light-emitting Device 27, except that the organic solvent was changed to butylamine (abbreviation: BBAβNαNB).

[0601] (Method for manufacturing light-emitting element 32) The light-emitting element 32 is obtained by replacing BBAαNβNB-03 in the light-emitting element 28 with the above structural formula (118). 4-(1;2'-binaphthyl-4-yl)-4',4''-diphenyltriphenyl ether The light-emitting device was fabricated in the same manner as in Light-emitting Device 28, except that the organic solvent was changed to butylamine (abbreviation: BBAβNαNB).

[0602] (Method for manufacturing light-emitting element 33) The light-emitting element 33 is obtained by replacing BBAαNβNB-03 in the light-emitting element 27 with the above structural formula (120). 4-(1,2'-binaphthyl-5-yl)-4',4''-diphenyltriphenyl ether The light-emitting device was fabricated in the same manner as light-emitting device 27, except that the fluorine-containing compound (BBAβNαNB-02) was used instead. Ta.

[0603] (Method for manufacturing light-emitting element 34) The light-emitting element 34 is obtained by replacing BBAαNβNB-03 in the light-emitting element 28 with the compound represented by the above structural formula (120). 4-(1,2'-binaphthyl-5-yl)-4',4''-diphenyltriphenyl ether The light-emitting device was fabricated in the same manner as light-emitting device 28, except that the fluorine-containing compound (BBAβNαNB-02) was used instead. Ta.

[0604] The device structures of the light-emitting devices 25 to 34 are summarized in the table below.

[0605] [Table 19]

[0606] The light emitting elements 25 to 34 are placed in a glove box with a nitrogen atmosphere. The process of sealing the device with a glass substrate to prevent it from being exposed to the atmosphere (sealing material is applied around the device After UV treatment during sealing and heat treatment at 80°C for 1 hour, the initial characteristics of these light-emitting devices were The measurements were carried out at room temperature (in an atmosphere maintained at 25°C).

[0607] 1000 cd / m of light-emitting elements 25 to 34 2 The main characteristics of the area are listed in the table below. Shown below.

[0608] [Table 20]

[0609] From Table 20, light-emitting elements 25 to 34 have a luminance of 1000 cd / m 2 External quantities in the vicinity The photonic efficiency was 11% to 13%, which was very good. The driving voltage was also uniformly low. It is clear that the light-emitting elements 25 to 34 are light-emitting elements with excellent luminous efficiency.

[0610] In addition, the current value was set to 2mA, and the change in brightness with respect to the driving time under the condition of a constant current density was measured. The ratio (%) of the luminance after 100 hours to the initial luminance of each element is shown in the table below. vinegar.

[0611] [Table 21]

[0612] The light-emitting elements 25 to 34 maintained 85% or more of their initial brightness even after 100 hours of operation. The brightness of each light-emitting element is maintained at a low level due to the accumulation of driving time, and the life span is long. It was found to be a light-emitting element. [Explanation of symbols]

[0613] 101 Anode 102 Cathode 103 EL layer 111 Hole injection layer 112 Hole transport layer 113 Light-emitting layer 114 Electron transport layer 115 Electron injection layer 116 Charge generation layer 117 P type layer 118 Electronic Relay Layer 119 Electron injection buffer layer 400 boards 401 First electrode 403 EL layer 404 Second electrode 405 Sealing material 406 Sealing material 407 Sealing substrate 412 Pad 420 IC chip 501 first electrode 502 Second electrode 503 EL layer 511 First Light Emitting Unit 512 Second Light Emitting Unit 513 Charge generation layer 601 Driver circuit section (source line driver circuit) 602 Pixel section 603 Drive circuit section (gate line drive circuit) 604 Sealing substrate 605 Sealing material 607 Space 608 Wiring 609 FPC (Flexible Printed Circuit) 610 Element substrate 611 Switching FET 612 Current control FET 613 First electrode 614 Insulators 616 EL layer 617 Second electrode 618 Light-emitting element 623 n-channel FET 624 p-channel FET 730 insulating film 770 Planarization insulating film 772 Conductive film 782 Light-emitting element 783 Droplet discharge device 784 Droplet 785 layers 786 Layer containing luminescent material 788 Conductive Film 901 Case 902 Liquid crystal layer 903 Backlight Unit 904 Case 905 Driver IC 906 terminal 951 PCB 952 Electrode 953 Insulation Layer 954 Partition layer 955 EL layer 956 Electrode 1001 board 1002 Undercoat insulating film 1003 Gate insulating film 1006 Gate electrode 1007 Gate electrode 1008 gate electrode 1020 First interlayer insulating film 1021 Second interlayer insulating film 1022 Electrode First electrode of 1024W light emitting element 1024R First electrode of light-emitting element 1024G First electrode of light-emitting element 1024B First electrode of light-emitting element 1025 Bulkhead 1028 EL layer 1029 Cathode 1031 Sealing substrate 1032 Sealing material 1033 Transparent substrate 1034R Red color layer 1034G Green color layer 1034B Blue color layer 1035 Black layer (black matrix) 1037 Third interlayer insulating film 1040 pixel section 1041 Drive circuit section 1042 Periphery 1400 Droplet discharge device 1402 PCB 1403 Droplet discharge means 1404 Imaging means 1405 Head 1406 dotted line 1407 Control means 1408 Storage medium 1409 Image processing means 1410 Computer 1411 Marker 1412 head 1413 Material Source 1414 Material Source 1415 Material Source 1416 Head 2001 Case 2002 light source 3001 Lighting equipment 5000 display area 5001 Display area 5002 Display area 5003 Display area 5004 Display area 5005 Display area 7101 Housing 7103 Display section 7105 Stand 7107 Display section 7109 Operation key 7110 Remote control device 7201 Main unit 7202 Case 7203 Display section 7204 keyboard 7205 External connection port 7206 Pointing Device 7210 Second display unit 7401 Housing 7402 Display section 7403 Operation button 7404 External connection port 7405 Speaker 7406 Microphone 9033 Fasteners 9034 Switch 9035 Power Switch 9036 Switch 9038 Operation switch 9310 Mobile Information Terminal 9311 Display Panel 9312 Display area 9313 Hinge 9315 Housing 9630 chassis 9631 Display section 9631a Display section 9631b Display section 9632a Touch panel area 9632b Touch panel area 9633 Solar Cells 9634 Charge / Discharge Control Circuit 9635 Battery 9636 DC / DC Converter 9637 Operation Key 9638 Converter 9639 Button

Claims

[Claim 1] An organic compound represented by formula (G1): 【Chemistry 1】 (However, in formula (G1), R １ ~R １０ each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a group represented by formulas (R-1) to (R-4), and R １１ ~R １４ each independently represents one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 3 to 6 carbon atoms. n represents 0, 1, or 2, and when n is 2, the two phenylene groups may have different substituents. naph represents a group represented by formula (g1-1) or a group represented by formula (g1-2). 【Chemistry 2】 (However, in formulas (R-1) to (R-4), R ６０ ~R ９１ are each independently one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 3 to 6 carbon atoms. 【Transformation 3】 (However, in formula (g1-1), R ２２ ~R ２８ one of the groups represented by formula (g2-1) or (g2-2) is a group represented by formula (g2-1) or (g2-2), and the remaining groups are each independently any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 3 to 6 carbon atoms. ３１ ~R ３７ one of which is a group represented by formula (g2-1) or a group represented by formula (g2-2), and the rest each independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 3 to 6 carbon atoms. 【Chemistry 4】 (However, in formula (g2-1), R ４２ ~R ４８ each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 3 to 6 carbon atoms. ５１ ~R ５７ each independently represents one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 3 to 6 carbon atoms.

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