Compound and light-emitting device

Abstract

To provide a novel compound.SOLUTION: A novel compound represented by the general formula (G1) is provided. In the general formula (G1), A represents a substituted or unsubstituted condensed aromatic ring having 10 to 30 carbon atoms, or a substituted or unsubstituted condensed heteroaromatic ring having 10 to 30 carbon atoms; R1 represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms; and each of Y1 and Y2 independently represents a cycloalkyl group having a bridge structure and having 7 to 10 carbon atoms.SELECTED DRAWING: None

Description

[Technical Field]

[0001] One aspect of the present invention relates to a compound, a light-emitting device, a light-emitting apparatus, an electronic device, and a lighting apparatus. However, one aspect of the present invention is not limited thereto. Alternatively, one aspect of the present invention relates to a process, a manufacturing method, or a driving method. Composition of Matter. [Background technology]

[0002] In recent years, electroluminescence (EL) These light-emitting devices are made up of a pair of electrodes. The light-emitting device has a structure in which an EL layer (containing a light-emitting material) is sandwiched between a pair of electrodes. By applying a voltage to the EL layer, electrons and holes injected from each electrode The light-emitting material (organic compound) contained in the EL layer becomes excited, and the excited state It emits light when it returns to the ground state. There are two types of excited states: singlet excited state (S * ) and triplet excited states (T * ) and emission from the singlet excited state is fluorescence, and emission from the triplet excited state is The emission from these is called phosphorescence. The rate is S * :T * =1:3. Therefore, the energy of the triplet excited state Light-emitting devices using phosphorescent materials that can convert energy into light are thought to be highly efficient. has been actively developed in recent years.

[0003] As a material capable of converting part or all of the energy of the triplet excited state into luminescence, In addition to phosphorescent materials, thermally activated delayed fluorescence (TFA) Delayed Fluorescence (TADF) materials are known. F materials can generate singlet excited states from triplet excited states through reverse intersystem crossing. .

[0004] By combining TADF materials with fluorescent materials as light-emitting devices, The singlet excitation energy of the ADF material is transferred to the fluorescent material, and the fluorescent material is efficiently A method for making it emit light has been proposed (see Patent Document 1).

[0005] In addition, the excitation energy from the host material to the guest material in the light-emitting layer of the light-emitting device can be Regarding energy transfer, it is generally considered to increase the efficiency of energy transfer by the Förster mechanism (energy transfer). To improve the energy transfer rate, a guest material (fluorescent material) is added to the host material. ) is preferred to be increased in concentration ratio, but increasing the concentration ratio of the guest material leads to the Dexter mechanism. This trade-off results in a decrease in the luminous efficiency due to the increase in the energy transfer rate. Therefore, increasing the concentration ratio of the guest material This cannot be said to be an effective means for improving light efficiency. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Japanese Patent Application Laid-Open No. 2014-45179 Summary of the Invention [Problem to be solved by the invention]

[0007] In one aspect of the present invention, novel compounds are provided, or in the EL layer of a light-emitting device, , even if the concentration ratio is increased, the singlet excited state (S * ) energy from (hereinafter referred to as The triplet excited state (T * ) The energy transfer from the dextran (hereinafter referred to as triplet excitation energy) is difficult to occur (dextran). The present invention provides a novel compound capable of suppressing energy transfer by a mechanism.

[0008] Another aspect of the present invention provides a novel compound that can be used in a light-emitting device. In addition, in one embodiment of the present invention, a novel compound that can be used in an EL layer of a light-emitting device is disclosed. Furthermore, a novel compound having high luminous efficiency that is an embodiment of the present invention is provided. A light-emitting device is provided. Also, a novel light-emitting device, a novel electronic device, or a novel lighting device is provided. Provide a place.

[0009] The description of these problems does not preclude the existence of other problems. It is not necessary for the present invention to solve all of these problems. The above will be made clear from the description, drawings, claims, etc. It is possible to extract other issues from the descriptions in the patent, claims, etc. [Means for solving the problem]

[0010] One embodiment of the present invention is a fluorescent substance, which is a compound represented by the following general formula (G1).

[0011] [ka]

[0012] In the general formula (G1), A is a substituted or unsubstituted fused aromatic ring having 10 to 30 carbon atoms. R represents a ring, or a substituted or unsubstituted fused heteroaromatic ring having 10 to 30 carbon atoms; 1 Ha Y represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. 1 and Y 2 is that Each independently represents any one of cycloalkyl groups having 7 to 10 carbon atoms and having a bridged structure. .

[0013] Another aspect of the present invention is a compound represented by the general formula (G1), wherein R 1 is a group having 6 to 25 carbon atoms represents an aryl group, and the aryl group has two or more substituents, and the two or more substituents are each independently represents an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkyl group having 3 to 1 carbon atoms, a cycloalkyl group having 0 carbon atoms, or a trialkylsilyl group having 3 to 12 carbon atoms, and the cycloalkyl group is any one of the cycloalkyl groups having 7 to 10 carbon atoms.

[0014] Another embodiment of the present invention is a compound represented by the following general formula (G2):

[0015] [ka]

[0016] In the above general formula (G2), A is a substituted or unsubstituted condensed aromatic ring having 10 to 30 carbon atoms. R represents a ring, or a substituted or unsubstituted fused heteroaromatic ring having 10 to 30 carbon atoms; 1 ~R 3 each independently represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. 1 and Y2 are each independently a cycloalkyl group having a bridged structure and having 7 to 10 carbon atoms. Represents one of the following.

[0017] Another embodiment of the present invention is a compound represented by the following general formula (G3).

[0018] [ka]

[0019] In the general formula (G3), A is a substituted or unsubstituted fused aromatic ring having 10 to 30 carbon atoms. ring, or a substituted or unsubstituted fused heteroaromatic ring having 10 to 30 carbon atoms; Z 1 ~ Z 3 are each independently represented by general formula (Z-1), general formula (Z-2), and general formula (Z-3), In general formula (Z-1), X 1 and X 2 are respectively Independently, an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, Y represents either a trialkyl group or a trialkylsilyl group having 3 to 12 carbon atoms. 1 ~Y 4 are each independently a cycloalkyl group having a bridged structure and having 7 to 10 carbon atoms. In the general formula (Z-3), Ar 1 and Ar 2 are each independently substituted or represents an unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms, and Ar 1 and Ar 2 Few First of all, X 1 , X 2 , Y 1 , Y 2 , Y 3 , or Y 4 having the same substituent as one of do.

[0020] Another embodiment of the present invention is a compound represented by general formula (G4).

[0021] [ka]

[0022] In the above general formula (G4), A is a substituted or unsubstituted fused aromatic ring having 10 to 30 carbon atoms. ring, or a substituted or unsubstituted fused heteroaromatic ring having 10 to 30 carbon atoms; Z 1 Oh BiZ 2 are each independently represented by general formula (Z-4), general formula (Z-5), and general formula (Z-6 In general formula (Z-4), X 1 and X 2 Each independently, an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted silyl group having 3 to 10 carbon atoms, Y represents any one of a cycloalkyl group and a trialkylsilyl group having 3 to 12 carbon atoms. 1 ~ Y 6 are each independently any one of cycloalkyl groups having 7 to 10 carbon atoms and having a crosslinked structure. In the general formula (Z-6), Ar 1 and Ar 2 are each independently substituted or unsubstituted. represents a substituted aromatic hydrocarbon group having 6 to 13 carbon atoms, and Ar 1 and Ar 2 At least Another one is X 1 , X 2 , Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , or Y 6 The same place as one of It has a substituent.

[0023] Another embodiment of the present invention is a compound represented by general formula (G5).

[0024] [ka]

[0025] In the above general formula (G5), Z 1 ~Z 3 are each independently represented by general formula (Z-1), general formula The general formula (Z-2) and the general formula (Z-3) have a structure represented by either one of the following: -1) Medium, X 1 and X 2 are each independently an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkyl group, or unsubstituted cycloalkyl groups having 3 to 10 carbon atoms, trialkyl groups having 3 to 12 carbon atoms, Y represents one of the aryl groups. 1 ~Y 4 are each independently a crosslinked group having 7 or more carbon atoms In the general formula (Z-3), Ar represents any one of cycloalkyl groups of 1 to 10. 1 and Ar 2 each independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms, And Ar 1 and Ar 2 At least one of the X 1 , X 2 , Y 1 , Y 2 , Y 3 , or Y 4 In addition, R 4 ~R 11 are independently hydrogen, carbon an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms; a trialkylsilyl group having 3 to 12 carbon atoms, or a substituted or unsubstituted trialkylsilyl group having 6 or more carbon atoms; represents any one of aryl groups from 1 to 25.

[0026] Another embodiment of the present invention is a compound represented by general formula (G6).

[0027] [ka]

[0028] In the above general formula (G6), Z 1 and Z 2 are each independently represented by general formula (Z-4), It has a structure represented by either general formula (Z-5) or general formula (Z-6). (Z-4) Medium, X 1 and X 2 are each independently an alkyl group having 3 to 10 carbon atoms, a substituted or an unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a trialkyl group having 3 to 12 carbon atoms, Y represents one of the aryl and silyl groups. 1 ~Y 6 are each independently the number of carbon atoms having a crosslinked structure In the general formula (Z-6), Ar represents any one of 7 to 10 cycloalkyl groups. 1 and Ar 2 each independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms; And Ar 1 and Ar 2 At least one of the X 1 , X 2 , Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , or Y 6 In addition, R 4 ~R 11 are each unique In particular, hydrogen, an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkyl group having 3 to 10 carbon atoms, a cycloalkyl group, a trialkylsilyl group having 3 to 12 carbon atoms, or a substituted or unsubstituted It represents any one of substituted aryl groups having 6 to 25 carbon atoms.

[0029] Another embodiment of the present invention is a compound represented by structural formula (100).

[0030] [ka]

[0031] Another embodiment of the present invention is a light-emitting device using the compound according to any one of the above embodiments of the present invention. In addition, the EL layer between the pair of electrodes or the light-emitting layer included in the EL layer may be an embodiment of the present invention. The present invention also includes light-emitting devices formed using such compounds. In addition to the above light-emitting device, a layer (for example, a cap layer) having an organic compound in contact with the electrode is provided. Such cases are also included in the light-emitting device and are included in the present invention. In addition, light-emitting devices having transistors, substrates, etc. are also included in the scope of the invention. In addition to the light-emitting device, microphone, camera, operation buttons, external connection parts, housing, cover, support The invention also includes electronic devices or lighting devices having stands or speakers.

[0032] Another embodiment of the present invention includes a light-emitting device having a light-emitting device, and further includes a light-emitting device having a light-emitting device. Therefore, the light-emitting device in this specification includes an illumination device that emits an image. It refers to a display device or a light source (including lighting equipment). Also, a light-emitting device may be connected to, for example, an FPC ( Flexible printed circuit) or TCP (Tape Cable) Modules with connectors such as the EtherNet / IP Package, A module with a printed wiring board mounted on the light-emitting device, or a COG (Chip On Glass) All modules with IC (integrated circuit) directly mounted using the OLED Glass method are also luminous. This shall be included in the location. [Effects of the Invention]

[0033] According to one aspect of the present invention, a novel compound can be provided. In this case, a novel compound that can be used in a light-emitting device can be provided. In one aspect of the present invention, a novel compound is provided that can be used in an EL layer of a light-emitting device. According to one embodiment of the present invention, a light-emitting device with high emission efficiency can be provided. Alternatively, according to one embodiment of the present invention, a highly reliable light-emitting device can be provided. Alternatively, in one embodiment of the present invention, a novel light-emitting device can be provided. Alternatively, in one embodiment of the present invention, a novel light-emitting device, a novel electronic device, or a novel lighting device can be provided. A lighting device can be provided.

[0034] The description of these effects does not preclude the existence of other effects. It is not necessary to have all of these effects. Effects other than these may be described in the specification, It is obvious from the description in the specification, drawings, claims, etc. Therefore, it is possible to extract other effects. [Brief explanation of the drawings]

[0035] [Figure 1] Fig. 1(A) is a diagram showing the structure of a light-emitting device, and Fig. 1(B) is a diagram explaining a light-emitting layer. [Figure 2] 2A is a conceptual diagram of energy transfer between a general guest material and a host material, and FIG. 2B is a conceptual diagram of energy transfer between a compound (guest material) according to one embodiment of the present invention and a host material. [Figure 3] Figure 3(A) is a conceptual diagram of energy transfer between compounds in the light-emitting layer. Figure 3(B) is a conceptual diagram of energy transfer between compounds in the light-emitting layer. Figure 3(C) is a conceptual diagram of energy transfer between compounds in the light-emitting layer. [Figure 4] Figure 4(A) is a conceptual diagram of energy transfer between compounds in the light-emitting layer. Figure 4(B) is a conceptual diagram of energy transfer between compounds in the light-emitting layer. Figure 4(C) is a conceptual diagram of energy transfer between compounds in the light-emitting layer. [Figure 5] Figure 5(A) is a conceptual diagram of energy transfer between compounds in the light-emitting layer, and Figure 5(B) is a conceptual diagram of energy transfer between compounds in the light-emitting layer. [Figure 6] 6(A) and 6(B) are diagrams illustrating the structure of the light-emitting device. [Figure 7] 7(A), 7(B), and 7(C) are diagrams illustrating a light emitting device. [Figure 8] Fig. 8(A) is a top view illustrating the light emitting device, and Fig. 8(B) is a cross-sectional view illustrating the light emitting device. [Figure 9] Fig. 9(A) is a diagram illustrating a mobile computer. Fig. 9(B) is a diagram illustrating a portable image playback device. Fig. 9(C) is a diagram illustrating a digital camera. Fig. 9(D) is a diagram illustrating a portable information terminal. Fig. 9(E) is a diagram illustrating a portable information terminal. Fig. 9(F) is a diagram illustrating a television device. Fig. 9(G) is a diagram illustrating a portable information terminal. [Figure 10] 10(A), 10(B), and 10(C) are diagrams illustrating a foldable mobile information terminal. [Figure 11] 11(A) and 11(B) are diagrams illustrating an automobile. [Figure 12] FIG. 1 is a diagram illustrating a lighting device. [Figure 13] FIG. 1 is a diagram illustrating a lighting device. [Figure 14] FIG. 14 is a 1H-NMR chart of the organic compound represented by the structural formula (100). [Figure 15] FIG. 15 shows the ultraviolet-visible absorption spectrum and emission spectrum of the organic compound represented by the structural formula (100). [Figure 16] FIG. 16 is a diagram illustrating a light-emitting device. [Figure 17] FIG. 17 is a graph showing the current density-luminance characteristics of light-emitting devices 1-1 to 1-5. [Figure 18] FIG. 18 is a diagram showing the voltage-luminance characteristics of light-emitting devices 1-1 to 1-5. [Figure 19] FIG. 19 is a graph showing the luminance-current efficiency characteristics of light-emitting devices 1-1 to 1-5. [Figure 20] FIG. 20 is a graph showing the voltage-current density characteristics of light-emitting devices 1-1 to 1-5. [Figure 21] FIG. 21 is a graph showing electroluminescence spectra of light-emitting devices 1-1 to 1-5. [Figure 22] FIG. 22 is a graph showing the current density-luminance characteristics of the light-emitting devices 2-1 to 2-5. [Figure 23] FIG. 23 is a diagram showing the voltage-luminance characteristics of the light-emitting devices 2-1 to 2-5. [Figure 24] FIG. 24 is a graph showing the luminance-current efficiency characteristics of the light-emitting devices 2-1 to 2-5. [Figure 25] FIG. 25 is a diagram showing the voltage-current density characteristics of the light-emitting devices 2-1 to 2-5. [Figure 26] FIG. 26 is a graph showing electroluminescence spectra of light-emitting devices 2-1 to 2-5. [Figure 27] FIG. 27 is a 1H-NMR chart of the organic compound represented by the structural formula (102). [Figure 28]FIG. 28 shows the ultraviolet-visible absorption spectrum and emission spectrum of the organic compound represented by the structural formula (102). [Figure 29] FIG. 29 is a 1H-NMR chart of the organic compound represented by the structural formula (116). [Figure 30] FIG. 30 shows the ultraviolet-visible absorption spectrum and emission spectrum of the organic compound represented by the structural formula (116). [Figure 31] FIG. 31 is a 1H-NMR chart of the organic compound represented by the structural formula (120). [Figure 32] FIG. 32 shows the ultraviolet-visible absorption spectrum and emission spectrum of the organic compound represented by the structural formula (120). [Figure 33] FIG. 33 is a diagram illustrating the reliability measurement results of light-emitting devices 1-1 to 1-5. [Figure 34] FIG. 34 is a diagram illustrating the reliability measurement results of the light-emitting devices 2-1 to 2-5. [Figure 35] FIG. 35 is a graph showing the current density-luminance characteristics of light-emitting devices 3-1 to 3-5. [Figure 36] FIG. 36 is a diagram showing the voltage-luminance characteristics of the light-emitting devices 3-1 to 3-5. [Figure 37] FIG. 37 is a graph showing the luminance-current efficiency characteristics of light-emitting devices 3-1 to 3-5. [Figure 38] FIG. 38 is a diagram showing the voltage-current density characteristics of light-emitting devices 3-1 to 3-5. [Figure 39] FIG. 39 is a graph showing the luminance-external quantum efficiency characteristics of light-emitting devices 3-1 to 3-5. [Figure 40] FIG. 40 is a graph showing electroluminescence spectra of light-emitting devices 3-1 to 3-5. [Figure 41] FIG. 41 is a graph showing the current density-luminance characteristics of the light-emitting devices 4-1 to 4-5. [Figure 42]FIG. 42 is a diagram showing the voltage-luminance characteristics of the light-emitting devices 4-1 to 4-5. [Figure 43] FIG. 43 is a graph showing the luminance-current efficiency characteristics of light-emitting devices 4-1 to 4-5. [Figure 44] FIG. 44 is a diagram showing the voltage-current density characteristics of the light-emitting devices 4-1 to 4-5. [Figure 45] FIG. 45 is a graph showing the luminance-external quantum efficiency characteristics of the light-emitting devices 4-1 to 4-5. [Figure 46] FIG. 46 is a graph showing electroluminescence spectra of light-emitting devices 4-1 to 4-5. [Figure 47] FIG. 47 is a diagram illustrating the reliability measurement results of the light-emitting devices 4-1 to 4-5. [Figure 48] FIG. 48 is a graph showing the current density-luminance characteristics of light-emitting devices 5-1 to 5-5. [Figure 49] FIG. 49 is a diagram showing the voltage-luminance characteristics of the light-emitting devices 5-1 to 5-5. [Figure 50] FIG. 50 is a graph showing the luminance-current efficiency characteristics of light-emitting devices 5-1 to 5-5. [Figure 51] FIG. 51 is a diagram showing the voltage-current density characteristics of light-emitting devices 5-1 to 5-5. [Figure 52] FIG. 52 is a graph showing the luminance-external quantum efficiency characteristics of light-emitting devices 5-1 to 5-5. [Figure 53] FIG. 53 is a graph showing electroluminescence spectra of light-emitting devices 5-1 to 5-5. [Figure 54] FIG. 54 is a graph showing the current density-luminance characteristics of the light-emitting devices 6-1 to 6-5. [Figure 55] FIG. 55 is a diagram showing the voltage-luminance characteristics of the light-emitting devices 6-1 to 6-5. [Figure 56]FIG. 56 is a graph showing the luminance-current efficiency characteristics of the light-emitting devices 6-1 to 6-5. [Figure 57] FIG. 57 is a diagram showing the voltage-current density characteristics of the light-emitting devices 6-1 to 6-5. [Figure 58] FIG. 58 is a graph showing the luminance-external quantum efficiency characteristics of the light-emitting devices 6-1 to 6-5. [Figure 59] FIG. 59 is a diagram showing electroluminescence spectra of light-emitting devices 6-1 to 6-5. [Figure 60] FIG. 60 is a diagram illustrating the reliability measurement results of the light-emitting devices 6-1 to 6-5. [Figure 61] FIG. 61 is a graph showing the current density-luminance characteristics of the light-emitting devices 7-1 to 7-5. [Figure 62] FIG. 62 is a diagram showing the voltage-luminance characteristics of the light-emitting devices 7-1 to 7-5. [Figure 63] FIG. 63 is a graph showing the luminance-current efficiency characteristics of the light-emitting devices 7-1 to 7-5. [Figure 64] FIG. 64 is a diagram showing the voltage-current density characteristics of the light-emitting devices 7-1 to 7-5. [Figure 65] FIG. 65 is a graph showing the luminance-external quantum efficiency characteristics of the light-emitting devices 7-1 to 7-5. [Figure 66] FIG. 66 is a diagram showing electroluminescence spectra of light-emitting devices 7-1 to 7-5. [Figure 67] FIG. 67 is a diagram illustrating the reliability measurement results of the light-emitting devices 7-1 to 7-5. [Figure 68] FIG. 68 is a diagram showing the current density-luminance characteristics of light-emitting devices 8-1 to 8-5. [Figure 69] FIG. 69 is a diagram showing the voltage-luminance characteristics of the light-emitting devices 8-1 to 8-5. [Figure 70]FIG. 70 is a graph showing the luminance-current efficiency characteristics of light-emitting devices 8-1 to 8-5. [Figure 71] FIG. 71 is a diagram showing the voltage-current density characteristics of light-emitting devices 8-1 to 8-5. [Figure 72] FIG. 72 is a graph showing the luminance-external quantum efficiency characteristics of light-emitting devices 8-1 to 8-5. [Figure 73] FIG. 73 is a diagram showing electroluminescence spectra of light-emitting devices 8-1 to 8-5. [Figure 74] FIG. 74 is a diagram illustrating the reliability measurement results of light-emitting devices 8-1 to 8-5. DETAILED DESCRIPTION OF THE INVENTION

[0036] Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. The present invention is not limited to the above description, and the form and details thereof may be changed without departing from the spirit and scope of the present invention. Therefore, the present invention is not limited to the embodiments described below. It is not to be construed as being limited to the

[0037] In addition, the position, size, range, etc. of each component shown in the drawings are not necessarily the same as those in the actual embodiment for ease of understanding. Therefore, the disclosed invention may not necessarily represent the actual position, size, range, etc. The position, size, range, etc. are not necessarily limited to those disclosed in the drawings, etc.

[0038] In addition, in this specification and the like, when explaining the configuration of the invention using drawings, the same The reference numerals are commonly used even among different drawings.

[0039] In this specification and the like, the singlet excited state (S * ) is a singlet with excitation energy The S1 level is the lowest singlet excited energy level, The lowest excited energy level is the singlet excited state (S1 state). Excited state (T * ) is a triplet state with excitation energy. Also, the T1 level is the lowest triplet excited energy level, and the lowest triplet excited state (T1 state) In this specification, the term "singlet excited state" is used to refer to the excited energy level of the singlet excited state. Even when written as S1 state and S1 level, In addition, when written as triplet excited state and triplet excited energy level, Even in this case, it may represent a T1 state and T1 level.

[0040] In this specification and the like, the term "fluorescent substance" refers to a substance that emits light when it relaxes from a singlet excited state to a ground state. Phosphorescent materials are compounds that emit light in the visible or near-infrared region. When relaxing from the excited state to the ground state, it emits light in the visible or near-infrared region at room temperature. In other words, a phosphorescent material is a compound that converts triplet excitation energy into light. It is one of the exchangeable compounds.

[0041] (Embodiment 1) In this embodiment, a compound according to one embodiment of the present invention will be described. Such a compound is represented by the following general formula (G1).

[0042] [ka]

[0043] In the general formula (G1), A represents a substituted or unsubstituted fused aromatic ring having 10 to 30 carbon atoms. R represents a fused heteroaromatic ring or a substituted or unsubstituted heteroaromatic ring having 10 to 30 carbon atoms; 1 teeth represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. 1 and Y 2 Haso each independently represents any one of cycloalkyl groups having 7 to 10 carbon atoms and having a bridged structure. vinegar.

[0044] Another aspect of the present invention is a compound represented by the general formula (G1), wherein R 1 is a group having 6 to 25 carbon atoms represents an aryl group, and the aryl group has two or more substituents, and the two or more substituents are each independently represents an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkyl group having 3 to 1 carbon atoms, a cycloalkyl group having 0 carbon atoms, or a trialkylsilyl group having 3 to 12 carbon atoms, and the cycloalkyl group is any one of the cycloalkyl groups having 7 to 10 carbon atoms.

[0045] Another embodiment of the present invention is a compound represented by the following general formula (G2):

[0046] [ka]

[0047] In the general formula (G2), A is a substituted or unsubstituted fused aromatic ring having 10 to 30 carbon atoms. R represents a fused heteroaromatic ring or a substituted or unsubstituted heteroaromatic ring having 10 to 30 carbon atoms; 1 ~ R 3 each independently represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. 1 and Y 2 each independently represents a cycloalkyl group having a bridged structure and having 7 to 10 carbon atoms. It represents one of the following.

[0048] Another embodiment of the present invention is a compound represented by the following general formula (G3).

[0049] [ka]

[0050] In the general formula (G3), A is a substituted or unsubstituted fused aromatic ring having 10 to 30 carbon atoms. Z represents a fused heteroaromatic ring or a substituted or unsubstituted heteroaromatic ring having 10 to 30 carbon atoms; 1 ~ Z 3 are each independently represented by general formula (Z-1), general formula (Z-2), and general formula (Z-3), In general formula (Z-1), X 1 and X 2 are respectively Independently, an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, Y represents either a trialkyl group or a trialkylsilyl group having 3 to 12 carbon atoms. 1 ~Y 4 are each independently a cycloalkyl group having a bridged structure and having 7 to 10 carbon atoms. In the general formula (Z-3), Ar 1 and Ar 2 are each independently substituted or represents an unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms, and Ar 1 and Ar 2 Few First of all, X 1 , X 2 , Y 1 , Y 2 , Y 3 , or Y 4 having the same substituent as one of do.

[0051] Another embodiment of the present invention is a compound represented by general formula (G4).

[0052] [ka]

[0053] In the general formula (G4), A is a substituted or unsubstituted fused aromatic ring having 10 to 30 carbon atoms. Z represents a fused heteroaromatic ring or a substituted or unsubstituted heteroaromatic ring having 10 to 30 carbon atoms; 1 oh Yobi Z 2 are each independently represented by general formula (Z-4), general formula (Z-5), and general formula (Z- In general formula (Z-4), X has a structure represented by any one of 1 and X 2 is that each independently represents an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkyl group having 3 to 10 carbon atoms, Y represents any one of a cycloalkyl group and a trialkylsilyl group having 3 to 12 carbon atoms. 1 ~Y 6 are each independently a cycloalkyl group having a bridged structure and having 7 to 10 carbon atoms. In the general formula (Z-6), Ar 1 and Ar 2 are each independently substituted or represents an unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms, and Ar 1 and Ar 2 Less Tomoichi is X 1 , X 2 , Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , or Y 6 Same as one of It has a substituent.

[0054] Another embodiment of the present invention is a compound represented by general formula (G5).

[0055] [ka]

[0056] In general formula (G5), Z 1 ~Z 3 are each independently represented by general formula (Z-1), It has a structure represented by general formula (Z-2) and general formula (Z-3). , X 1 and X 2 each independently represents an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkyl group, substituted cycloalkyl groups having 3 to 10 carbon atoms, trialkylsilyl groups having 3 to 12 carbon atoms, Y 1 ~Y 4 each independently represents a crosslinked group having 7 to 10 carbon atoms In the general formula (Z-3), Ar represents any one of the cycloalkyl groups. 1 and Ar 2 is that each independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms, and Ar 1 and Ar 2 At least one of the X 1 , X 2 , Y 1 , Y 2 , Y 3 , or Y 4 Either It has the same substituent as R 4 ~R 11 are each independently hydrogen, a group having 3 to 4 carbon atoms, an alkyl group having 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted trialkylsilyl group having 3 to 12 carbon atoms, or a substituted or unsubstituted trialkylsilyl group having 6 to 25 carbon atoms; represents any one of the aryl groups.

[0057] Another embodiment of the present invention is a compound represented by general formula (G6).

[0058] [ka]

[0059] In general formula (G6), Z 1 and Z 2 each independently represents a general formula (Z-4), It has a structure represented by general formula (Z-5) and general formula (Z-6). Medium, X 1 and X 2 are each independently an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkyl group, Substituted cycloalkyl groups having 3 to 10 carbon atoms, trialkylsilyl groups having 3 to 12 carbon atoms Y 1 ~Y 6 each independently represents a crosslinked group having 7 to 10 carbon atoms In the general formula (Z-6), Ar represents any one of the cycloalkyl groups 1 and Ar 2 Haso each independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms, and A r 1 and Ar 2 At least one of the X 1 , X 2 , Y 1 , Y 2 , Y 3 , Y 4 , Y 5 ,Also is Y 6 In addition, R 4 ~R 11 are each independently hydrogen an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkyl group, a trialkylsilyl group having 3 to 12 carbon atoms, or a substituted or unsubstituted alkyl group having 3 to 12 carbon atoms; represents any one of aryl groups having 6 to 25 carbon atoms.

[0060] The compound according to one embodiment of the present invention is a material having a function of converting singlet excitation energy into luminescence. As a guest material, it can be used in the light-emitting layer of a light-emitting device. The compound according to one embodiment of the present invention can be used together with a light-emitting material that contributes to light emission. The photophore and triplet excitation energy transfer from the host material to the compound via the Dexter mechanism. The lumophore contained in the compound according to one embodiment of the present invention is a fused aromatic ring. The protecting group of the compound of one embodiment of the present invention is In the two or more diarylamino groups that the compound of one embodiment of the present invention has, Specifically, each of the alkyl groups has at least two carbon atoms having a crosslinked structure. Cycloalkyl groups having 7 to 10 prime numbers, alkyl groups having 3 to 10 carbon atoms, substituted or unsubstituted alkyl groups substituted cycloalkyl groups having 3 to 10 carbon atoms and trialkylsilyl groups having 3 to 12 carbon atoms; It is one of the groups.

[0061] The compound according to one embodiment of the present invention has two or more diamines having protecting groups attached to the luminophore. By creating a structure in which the aryl amino groups are bonded at symmetrical positions, it is possible to increase the quantum yield. In addition, in the compound of one embodiment of the present invention, a diarylamino group can be used. This makes it possible to suppress an increase in molecular weight and maintain sublimability.

[0062] In the compound according to one embodiment of the present invention, the protecting group is a diarylamine bonded to the luminophore. Since it has a structure that bonds with the aryl group of the amino group, a protecting group is placed to cover the luminophore. Energy transfer from the host material to the luminophore occurs based on the Dexter mechanism. This allows you to keep the two apart by creating a distance that is difficult to distinguish between them.

[0063] In addition, in the above general formula (G1), general formula (G2), general formula (G3), and general formula (G4), In the above, a fused aromatic ring having 10 to 30 carbon atoms or a fused heteroaromatic ring having 10 to 30 carbon atoms Examples of the compound include a phenanthrene skeleton, a stilbene skeleton, an acridone skeleton, and a phenoxazine skeleton. In addition, the fluorescent quantum yield can be further increased. Naphthalene skeleton, anthracene skeleton, fluorene skeleton, chrysene skeleton, triphenylene skeleton ene skeleton, tetracene skeleton, pyrene skeleton, perylene skeleton, coumarin skeleton, quinacridone skeleton and naphthobisbenzofuran skeletons.

[0064] In addition, in the above general formula (G3), general formula (G4), general formula (G5), and general formula (G6), In the above, examples of the aromatic hydrocarbon group having 6 to 13 carbon atoms include a phenyl group, a biphenyl group, a naphthalene group, and the like. Examples include a butyl group and a fluorenyl group.

[0065] In addition, the general formula (G1), the general formula (G3), the general formula (G4), the general formula (G5), and In the general formula (G6), specific examples of the alkyl group having 3 to 10 carbon atoms include, for example, Examples of the alkyl group include a propyl group, a pentyl group, and a hexyl group.

[0066] In addition, the general formula (G1), the general formula (G3), the general formula (G4), the general formula (G5), and In the general formula (G6), specific examples of the cycloalkyl group having 3 to 10 carbon atoms include, for example, Examples include a cyclopropyl group, a cyclobutyl group, and a cyclohexyl group. When the cycloalkyl group has a substituent, specific examples of the substituent include a methyl group, an ethyl group, and an ethyl group. group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group alkyl groups having 1 to 7 carbon atoms, such as t-butyl, pentyl, and hexyl groups; butyl group, cyclohexyl group, cycloheptyl group, 8,9,10-trinorbornanyl group cycloalkyl groups having 5 to 7 carbon atoms, such as phenyl groups, naphthyl groups, and biphenyl groups Examples of such aryl groups include aryl groups having 6 to 12 carbon atoms.

[0067] In addition, the above general formula (G1), general formula (G2), general formula (G3), general formula (G4), general formula In the general formula (G5) and the general formula (G6), a cycloalkane having 7 to 10 carbon atoms and a bridged structure is Specific examples of alkyl groups include adamantyl group, bicyclo[2.2.1]heptyl group, Group, tricyclo[5.2.1.0 2,6 ]decanyl group, noradamantyl group, etc. do.

[0068] In addition, the general formula (G1), the general formula (G3), the general formula (G4), the general formula (G5), and In general formula (G6), specific examples of the trialkylsilyl group having 3 to 12 carbon atoms include , for example, a trimethylsilyl group, a triethylsilyl group, a tert-butyldimethylsilyl group groups, etc.

[0069] The above general formula (G1), general formula (G2), general formula (G3), general formula (G4), general formula (G5) ), and in the general formula (G6), a fused aromatic ring, a fused heteroaromatic ring, a C6 to C13 aromatic ring, Substituted with either an aromatic hydrocarbon group or a cycloalkyl group having 3 to 10 carbon atoms When the alkyl group has a substituent, the substituent may be a methyl group, an ethyl group, a propyl group, an isopropyl group, Butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group alkyl groups having 1 to 7 carbon atoms, such as a cyclopentyl group, a cyclohexyl group, ... a cycloalkyl group having 5 to 7 carbon atoms, such as a cycloheptyl group, a 8,9,10-trinorbornanyl group, an aryl group having 6 to 12 carbon atoms, such as an alkyl group, a phenyl group, a naphthyl group, or a biphenyl group; groups, etc.

[0070] In the above general formula (G1), general formula (G2), general formula (G5), or general formula (G6), Specific examples of the aryl group having 6 to 25 carbon atoms include a phenyl group, a naphthyl group, a biphenyl group, and a phenyl group. Examples of the aryl group include an aryl group, a fluorenyl group, and a spirofluorenyl group. When the group has a substituent, the substituent may be the above-mentioned alkyl group having 3 to 10 carbon atoms, substituted or unsubstituted alkyl group having 3 to 10 carbon atoms. is an unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, Examples of such groups include aryl groups.

[0071] Next, specific examples of the compounds represented by the above general formulae (G1) to (G6) are shown below. The structural formulas (100) to (136) are shown. Specific examples of the compound are not limited to these.

[0072] [ka]

[0073] [ka]

[0074] [ka]

[0075] [ka]

[0076] [ka]

[0077] [ka]

[0078] [ka]

[0079] <Method for synthesizing organic compound represented by general formula (G1)> Next, a method for synthesizing the compound represented by the following general formula (G1) will be described.

[0080] [ka]

[0081] In the general formula (G1), A is a substituted or unsubstituted fused aromatic ring having 10 to 30 carbon atoms, or or a substituted or unsubstituted fused heteroaromatic ring having 10 to 30 carbon atoms; R 1 If substitution or an unsubstituted aryl group having 6 to 25 carbon atoms. 1 and Y 2 are each unique In addition, it represents any one of cycloalkyl groups having 7 to 10 carbon atoms and having a crosslinked structure.

[0082] The compound represented by the general formula (G1) can be prepared, for example, by the following synthesis scheme (S-1) and synthesis scheme (S-2). It can be synthesized by the method shown in Synthesis Scheme (S-2).

[0083] First, compound 1 and compound 2 (arylamine) are coupled to form the compound Compound 3 (diamine compound) can be obtained (Synthetic Scheme (S-1)).

[0084] [ka]

[0085] Subsequently, compound 3 (diamine compound) and compound 4 (aryl halide) are coupled. By carrying out the reaction, a compound represented by general formula (G1) can be obtained (synthetic scheme). Room (S-2).

[0086] [ka]

[0087] The compound represented by the general formula (G1) can be synthesized by the following synthesis scheme (S-3) and synthesis scheme (S-4). It can also be synthesized by the method shown in Scheme (S-4).

[0088] First, compound 2 (arylamine) and compound 4 (aryl halide) are coupled. Compound 5 (amine compound) can be obtained by carrying out the synthesis scheme (S- 3)).

[0089] [ka]

[0090] Subsequently, Compound 1 and Compound 5 (amine compound) are coupled to form a A compound represented by general formula (G1) can be obtained (Synthetic Scheme (S-4)).

[0091] [ka]

[0092] In the above synthesis schemes (S-1) to (S-4), A is a substituted or unsubstituted A fused aromatic ring having 10 to 30 carbon atoms, or a substituted or unsubstituted fused aromatic ring having 10 to 30 carbon atoms represents a heteroaromatic ring, and R 1 represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms; Y 1 and Y 2 are each independently a cycloalkyl group having 7 to 10 carbon atoms and a bridged structure. The condensed aromatic ring or condensed heteroaromatic ring may be any one of chrysene, fluorene, fluorene-substituted ... Phenanthrene, stilbene, acridone, phenoxazine, phenothiazine, pyrene, Examples include marin, quinacridone, perylene, tetracene, naphthobisbenzofuran, etc. Anthracene is particularly preferred.

[0093] In the above synthesis schemes (S-1) to (S-4), When performing the Hubbard-Hartwig reaction, X 10 and X 11 is a halogen group or trifluoride The halogen is preferably iodine, bromine or chlorine. , bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, etc. dium compounds and tri(tert-butyl)phosphine, tri(n-hexyl)phosphine phosphine, tricyclohexylphosphine, di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, etc. In addition, organic bases such as sodium tert-butoxide, Inorganic bases such as potassium carbonate, cesium carbonate, or sodium carbonate can be used. In addition, the solvents used are toluene, xylene, mesitylene, benzene, tetrahydrofuran, Reagents that can be used in this reaction include hexane, dioxane, etc. However, the reagents are not limited to these.

[0094] The reactions carried out in the above synthesis schemes (S-1) to (S-4) are carried out by Buchwald reaction. The Hartwig reaction is not limited to this, but also involves the use of organotin compounds such as Migita, Kosugi, and Stiegler. Coupling reaction using Grignard reagents, copper or copper compounds The Ullmann reaction, which was used in the previous method, can be used.

[0095] <Method for synthesizing organic compound represented by general formula (G2)> Next, a method for synthesizing the compound represented by the following general formula (G2) will be described.

[0096] [ka]

[0097] In the general formula (G2), A is a substituted or unsubstituted fused aromatic ring having 10 to 30 carbon atoms, or or a substituted or unsubstituted fused heteroaromatic ring having 10 to 30 carbon atoms; R 1 ~R 3 Haso Each of Y independently represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. 1 and Y 2 are each independently any one of cycloalkyl groups having 7 to 10 carbon atoms and having a crosslinked structure. Represents one or two.

[0098] The compound represented by the general formula (G2) can be prepared, for example, by the method shown in the following synthesis scheme (S-5). It can be synthesized by the method.

[0099] Coupling of Compound 6, Compound 5 (amine compound), and Compound 7 (amine compound) By carrying out the above-mentioned reaction, a compound represented by general formula (G2) can be obtained (see the synthesis scheme below). (S-5)).

[0100] [ka]

[0101] In the above synthesis scheme (S-5), A is a substituted or unsubstituted aryl group having 10 to 15 carbon atoms. 30 fused aromatic rings or substituted or unsubstituted fused heteroaromatic rings having 10 to 30 carbon atoms represents R 1 ~R 3 each independently represents a substituted or unsubstituted aryl having 6 to 25 carbon atoms; represents the Y group. 1 and Y 2 each independently represents a cycloalkyl group having 7 to 10 carbon atoms and a crosslinked structure. The condensed aromatic ring or condensed heteroaromatic ring is a chrysene ring or a cycloalkyl group. phenanthrene, stilbene, acridone, phenoxazine, phenothiazine, pyrene Examples include benzofuran, coumarin, quinacridone, perylene, tetracene, and naphthobisbenzofuran. Anthracene is particularly preferred.

[0102] In the above synthesis scheme (S-5), the Buchwald-Haas reaction using a palladium catalyst When performing the Twigg reaction, X 12 and X 13 represents a halogen group or a triflate group. The halogen is preferably iodine, bromine, or chlorine. Palladium compounds such as diphenylideneacetone palladium(0) and palladium(II) acetate and tri(tert-butyl)phosphine, tri(n-hexyl)phosphine, tricyclyl Dihexylphosphine, Di(1-adamantyl)-n-butylphosphine, 2-dicyclo Using ligands such as hexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, In addition, organic bases such as sodium tert-butoxide, potassium carbonate, etc. Inorganic bases such as cesium carbonate, sodium carbonate, etc. can be used. The solvents used are toluene, xylene, mesitylene, benzene, tetrahydrofuran, dioxane, The reagents that can be used in this reaction are as follows: It is not limited to medicines.

[0103] The reaction carried out in the above synthesis scheme (S-5) is carried out by Buchwald-Hartwig The reaction is not limited to the Migita-Kosugi-Stille coupling using organotin compounds. reaction, coupling reaction using Grignard reagents, Ullmann reaction using copper or copper compounds reaction, etc. can be used.

[0104] In the above synthesis scheme (S-5), compound 6 and compound 5 are first reacted to couple It is preferable to obtain the coupling product and then react the obtained coupling product with Compound 7. It's nice.

[0105] Although the synthesis method of the compound according to one embodiment of the present invention has been described above, the present invention is not limited thereto. It is not necessary to synthesize the compound, and it may be synthesized by other synthesis methods.

[0106] (Embodiment 2) In this embodiment, a light-emitting device using a compound according to one embodiment of the present invention is preferably used. An example will be described. As shown in FIG. 1(A), the light-emitting device has a first electrode 1 1A shows the case of an anode), and a second electrode 102 (FIG. 1A shows the case of an anode). , and the cathode are shown), and the EL layer 103 is sandwiched between a pair of electrodes. The EL layer 103 includes at least a light-emitting layer 113 and a hole injection layer 111. , a hole transport layer 112, an electron transport layer 114, an electron injection layer 115, and other functional layers are provided. It can be done.

[0107] The light-emitting layer 113 contains a light-emitting material (guest material) and a host material. In this device, by applying a voltage between a pair of electrodes, electrons are emitted from the cathode and holes are emitted from the anode. (holes) are injected into the EL layer 103, causing a current to flow. The recombination of carriers (electrons and holes) at The light emitted from the light-emitting device is obtained by converting the electrons into light. The light-emitting layer 113 shown in FIG. 1(B) is an energy acceptor and a light-emitting material. Compound 132 acts as a guest material, and compound 133 acts as an energy donor and a host. Therefore, in this embodiment, one of the present invention The case where the compound according to the embodiment is used as a light-emitting substance (guest material) will be described. In the light-emitting layer 113, a plurality of compounds may function as host materials.

[0108] Of the excitons generated by carrier recombination, the rate of singlet excitons is 25%. The rate at which triplet excitons are generated is 75%, so triplet excitons are generated in addition to singlet excitons. It is preferable to make the electrons contribute to light emission in order to improve the light-emitting efficiency of the light-emitting device. Here, in the light-emitting layer 113, energy transfer occurs between the guest material and the host material. The concept of this movement will be explained using Figure 2. Note that Figure 2(A) shows a typical guest material ( The structure of the fluorescent material is shown, and the relationship between the guest material and the host material when this is used is shown. FIG. 2(B) shows the concept of energy transfer between compounds according to one embodiment of the present invention. The structure of 132 is shown, and when this is used as a guest material, the guest material and the host This illustrates the concept of energy transfer between materials.

[0109] FIG. 2(A) shows a compound 131 as a host material and a fluorescent material 124 as a guest material. The fluorescent material 124 is a general fluorescent material, It is a fluorescent substance that has a photophore 124a but does not have a protecting group.

[0110] FIG. 2B shows a compound 131 as a host material and a compound 132 as a guest material. The figure shows the state in which a compound (fluorescent substance) 132 is present. , a fluorescent emitting material that functions as an energy acceptor in a light emitting device; The compound (host material) has a luminophore 132a and a protecting group 132b. Energy transfer from the luminophore 131 to the luminophore 132a based on the Dexter mechanism is unlikely to occur. It has the function of keeping a certain distance between them.

[0111] As shown in FIGS. 2A and 2B, in the light-emitting layer 113, the compound 131, which is a host material, The guest material, fluorescent material 124 and compound (fluorescent material) 132, Therefore, as shown in FIG. 2(A), the fluorescent material 124 is retained. When the compound 131 does not have a protective group, the distance between the luminophore 124a and the compound 131 becomes short. The energy transfer from 131 to the fluorescent material 124 is via the Förster mechanism. Energy transfer (Route A6 in Figure 2(A)) and energy transfer via the Dexter mechanism (Figure 2 In (A), both route A7) can occur. The triplet excited energy is transferred to the guest material, and the triplet excited state of the guest material is Even if generated, if the guest material is a fluorescent material, the triplet excitation energy is lost non-radiatively. This is one of the reasons for the decrease in the luminous efficiency of the light-emitting device.

[0112] On the other hand, in FIG. 2B, a compound (fluorescent substance) 132 as a guest material is attached to a protecting group 13 The presence of 2b increases the distance between the luminophore 132a and the compound 131, which is the host material. This suppresses the energy transfer via the Dexter mechanism (route A7). It is possible.

[0113] Here, the luminophore 124a contained in the fluorescent substance 124 shown in FIG. 2(A) and the luminophore 124b contained in the fluorescent substance 124 shown in FIG. 2(B) The luminophore 132a contained in the compound (fluorescent material) 132 shown in The group (124a, 132a) is an atomic group (skeleton) that causes luminescence in a fluorescent substance. ) refers to the luminophores (124a, 132a) which generally have π bonds and contain aromatic rings. It is preferable that the compound has a condensed aromatic ring or a condensed heteroaromatic ring. Examples of the fused aromatic ring or fused heteroaromatic ring contained in the group (124a, 132a) include: Phenanthrene skeleton, stilbene skeleton, acridone skeleton, phenoxazine skeleton, phenothion In particular, naphthalene skeleton, anthracene skeleton, fluorene skeleton, Chrysene skeleton, triphenylene skeleton, tetracene skeleton, pyrene skeleton, perylene skeleton, coumarine skeleton Examples include a phosphorus skeleton, a quinacridone skeleton, and a naphthobisbenzofuran skeleton. The luminophore 132a possessed by the compound 132 according to one embodiment of the present invention is, in particular, an anthracene skeleton. The rank is preferred.

[0114] The protecting group 132b of the compound (fluorescent substance) 132 shown in FIG. 2(B) is , a T1 level higher than the T1 levels of the luminophore 132a and the host material, compound 131. It is preferable that the protecting group 13 of the compound 132 of one embodiment of the present invention is Specific examples of 2b are preferably cycloalkyl groups having a crosslinked structure and having 7 to 10 carbon atoms. In addition, alkyl groups having 3 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 carbon atoms, Examples of such protective groups include a trialkyl group having 3 to 12 carbon atoms and a trialkylsilyl group having 3 to 12 carbon atoms. By having the protective group 132b, a bulky structure can be obtained. Increasing the distance between the luminophore 132a of the compound 132 and the compound 131, which is the host material. can be done.

[0115] Next, a structure of a light-emitting layer of the light-emitting device according to one embodiment of the present invention will be described.

[0116] <Emitting layer configuration example 1> In this example, the light-emitting layer 113 in the light-emitting device is made of a compound that functions as a host material. The compound 131 functions as a light-emitting material (guest material), and the compound 132 functions as a light-emitting material (guest material). The TADF material is used as the compound 132 that functions as a light-emitting material (guest material). The case where a fluorescent substance is used will be described. It is preferable to use the compound 132 as a light-emitting substance. An example of the correlation of energy levels in the light-emitting layer 113 is shown in FIG. The notations and symbols shown in FIG. 3(A) are as follows: ·Host(131): Compound 131 ·Guest(132): Compound 132 T C1 :T1 level of compound 131 ·S C1 : S1 level of compound 131 ·S G : S1 level of compound 132 T G :T1 level of compound 132

[0117] In this example, compound 131 is a material having TADF, and therefore has triplet excitation energy It has the function of converting energy into singlet excitation energy by upconversion (Figure Route A1 in 3(A). The singlet excitation energy of compound 131 is rapidly converted to The compound 131 is transferred to compound 132 (Route A2 in Figure 3(A)). C1 and S of compound 132 G The relationship between C1 ≧S G However, S C1 is a compound Draw a tangent at the short wavelength side of the fluorescence spectrum of the substance 131, and calculate the energy of the wavelength of the extrapolated line. Also, S G is the energy of the wavelength at the absorption edge of the absorption spectrum of compound 132 -Let's do this.

[0118] In this way, the triplet excitation energy generated in compound 131 can be calculated by route A1 and route A2. The energy is transferred to the S1 level of the guest material, compound 132, via the The compound 132 can be made to emit light efficiently, thereby improving the luminous efficiency of the light-emitting device. In Route A2, compound 131 functions as an energy donor, and compound 132 functions as an energy donor. However, the light-emitting layer 11 of the light-emitting device shown in this configuration example In addition to the above, in 3, the triplet excitation energy generated in compound 131 is converted to the T This can also compete with the route to the first level (route A3 in Figure 3(A)). When the energy transfer (route A3) occurs, the fluorescent material, compound 132, is converted to triplet excited state. The luminous efficiency of the light-emitting device decreases because the energy cannot be used to emit light. .

[0119] Generally, the Förster mechanism (dipole-dipole interaction) is used as an intermolecular energy transfer mechanism. The Dexter mechanism (electron exchange interaction) is known. The distance between the energy donor compound and the energy acceptor compound is 1 nm. Therefore, the concentration of the energy acceptor compound is Therefore, as in this configuration example, Compound 132, which is a fluorescent material with a low triplet excitation energy level, has a concentration of When the triplet excitation energy of the energy donor compound 131 is higher, the triplet excitation energy of the The energy transfer via route A3 and subsequent non-radiative deactivation by the mechanism becomes dominant. Therefore, in order to suppress route A3, it is necessary to make it difficult for energy transfer via the Dexter mechanism to occur. It is important to increase the distance between compound 131 and compound 132 to a certain extent.

[0120] In addition, the T1 level (T G ) is compound 132 Therefore, the energy level of the light-emitting layer 113 is often derived from the luminophores contained in the light-emitting layer 113. In order to suppress route A3 in the luminophores, the distance between compound 131 and compound 132 was It is important to increase the distance.

[0121] To increase the distance between the energy donor and the luminophore of the energy acceptor, A common method is to reduce the concentration of the energy acceptor in the mixed film. However, when the concentration of the energy acceptor is reduced, Not only Dexter-based energy transfer to an energy acceptor, but also Fel The energy transfer based on the star mechanism is also suppressed. Because it is based on a star structure, there is a risk of a decrease in the luminous efficiency or reliability of the light-emitting device. On the other hand, the compound according to one embodiment of the present invention has a luminophore and a protecting group as part of its structure. and functions as an energy acceptor in the light-emitting layer 113. The protecting group has the function of increasing the distance between the luminophore and other energy donors. When the compound according to one embodiment of the present invention is used as compound 132 in this configuration, compound 1 The distance between 32 and compound 131 can be increased. When the distance between the acceptors and the bond is less than 1 nm, the Dexter mechanism predominates, and when the distance is more than 1 nm, the Dexter mechanism predominates. The Förster mechanism is dominant at 1 nm or less. Therefore, the protecting group should be placed at least 1 nm away from the luminophore. Bulky substituents extending over a range of 10 nm or less are preferred, and the compound of one embodiment of the present invention has The protecting group is preferably one of the protecting groups listed above. By using a compound similar to Compound 132, the concentration of Compound 132 was increased. While suppressing the energy transfer by the Dexter mechanism, the energy transfer by the Förster mechanism That is, the S1 level (S C1 ) to S1 level of compound 132 (S G ) to the singlet excitation energy (Route A2 ) is more likely to occur, while the T1 level (T G ) to Mie The transfer of excitation energy (Route A3: Energy transfer by the Dexter mechanism) occurs. This makes it possible to suppress the decrease in luminous efficiency due to the energy transfer of route A3. This can improve the luminous efficiency of the light-emitting device. By increasing the energy transfer rate, the excited lifetime of the energy acceptor in the light-emitting layer is shortened. Therefore, the reliability of the light-emitting device can be improved. The concentration of compound 132 in 3 is 2w relative to the energy donor compound 131. The content is preferably t% or more and 50wt% or less, more preferably 5wt% or more and 30wt% or less, and even more preferably 10wt% or more and 20wt% or less. The content is preferably 5 wt% or more and 20 wt% or less.

[0122] <Emitting layer configuration example 2> In this example, the light-emitting layer 113 in the light-emitting device contains Compound 131, Compound 132, and and Compound 133, and Compound 131 and Compound 133 form an exciplex. Compound 132 is a compound having a structure in which a fluorescent material is used. Therefore, in one aspect of the present invention, A certain compound is preferably used as the fluorescent substance, compound 132. An example of the correlation of energy levels in the light-emitting layer 113 in this configuration example is shown in FIG. The notations and symbols shown in FIG. 3(B) are as follows: ·Comp(131): Compound 131 ·Comp(133): Compound 133 ·Guest(132): Compound 132 ·S C1 : S1 level of compound 131 T C1 :T1 level of compound 131 ·S C3 : S1 level of compound 133 T C3 :T1 level of compound 133 ·S G : S1 level of compound 132 T G :T1 level of compound 132 ·S E : S1 level of the exciplex T E :T1 level of exciplex

[0123] The combination of Compound 131 and Compound 133 is capable of forming an exciplex. Any combination is acceptable, but one of them is a compound that has the function of transporting holes (hole transport property). It is more preferred that one of the compounds is a compound having a function of transporting electrons (electron transport property). In this case, it becomes easier to form a donor-acceptor type exciplex, and excitation is efficient. In addition, the combination of Compound 131 and Compound 133 can form a complex. In the case of a combination of a compound having hole transport properties and a compound having electron transport properties, the mixture The carrier balance can be easily controlled by the combination ratio. The ratio of the compound having electron transport properties to the compound having electron transport properties is in the range of 1:9 to 9:1 (weight ratio). Moreover, by having such a configuration, the carrier balance can be easily controlled. Therefore, the carrier recombination region can be easily controlled.

[0124] In addition, as a combination of host materials that efficiently form exciplexes, Compound 131 and In compound 133, one HOMO level is higher than the other, and one LUMO It is preferable that the HOMO level of the compound 131 is higher than the LUMO level of the other compound. is equal to the HOMO level of compound 133, or the LUMO level of compound 131 is equal to the LUMO level of compound 13 The LUMO level may be equivalent to that of 3.

[0125] The LUMO and HOMO levels of the compounds were determined by cyclic voltammetry (CV ) measurements are derived from the electrochemical properties (reduction and oxidation potentials) of compounds. It is possible.

[0126] As shown in Figure 3(B), the S of the exciplex formed by Compound 131 and Compound 133 1 level (S E ) and T1 level (T E ) are adjacent energy levels (Figure 3 (See route A6 in (B)).

[0127] Excitation energy levels of exciplexes (S E and T E ) is the compound that forms the exciplex. The S1 level (S C1 and S C3 ) is lower, so This allows the formation of excited states with lower excitation energies. The driving voltage of the sensor can be reduced.

[0128] In addition, the S1 level of the exciplex (S E ) and T1 level (T E ) are adjacent energy levels Because of this position, reverse intersystem crossing is easily observed and the exciplex has TADF properties. The function of converting excitation energy into singlet excitation energy by upconversion The singlet excitation energy of the exciplex is rapidly released (Route A7 in Figure 3(B)). It can be transferred to compound 132 (Route A8 in Figure 3(B)). E ≧S G In Route A8, the exciplex is the energy donor, Compound 132 acts as an energy acceptor. Specifically, the fluorescence of the exciplex is Draw a tangent line at the short wavelength side of the spectrum, and let the wavelength energy of the extrapolated line be S E year , where S is the energy of the wavelength at the absorption edge of the absorption spectrum of compound 132. G When this is done, S E ≧ S G It is preferable that:

[0129] To enhance the TADF properties, the T1 levels of both Compound 131 and Compound 133, Nawachi T C1 and T C3 But, T E It is preferable that the value is equal to or greater than 1. The emission peak wavelengths on the shortest wavelength side of the phosphorescence spectra of Compounds 131 and 133 are It is preferable that the wavelength of each of the exciplexes is equal to or shorter than the maximum emission peak wavelength. Draw a tangent line at the short wavelength side of the optical spectrum, and define the wavelength energy of the extrapolated line as S E The phosphorescence spectra of Compound 131 and Compound 133 are connected at the short wavelength side. The energy of the wavelength of the extrapolated lines is calculated as the T of each compound. C1 and T C3 When To, S E -T C1 ≦0.2 eV and S E -T C3 Preferably ≦0.2 eV .

[0130] The triplet excitation energy generated in the light-emitting layer 113 is transferred to the guest via Route A6 and Route A8. By transferring energy to the S1 level of the material compound 132, compound 132 Therefore, the light-emitting layer 113 is made of a combination of materials that form an exciplex. The use of the luminous layer 1 can improve the luminous efficiency of the fluorescent light-emitting device. The triplet excitation energy generated in 13 is transferred to the T1 level of compound 132. This energy transfer (route A9 in Figure 3(B)) can occur in competition with the other route. When the triplet excitation energy is released, the fluorescent compound 132 Since the electrons cannot contribute to light emission, the light emitting efficiency of the light emitting device decreases.

[0131] In order to suppress such energy transfer (route A9 in FIG. 3(B)), As explained in Example 1, the exciplex formed by Compound 131 and Compound 133 and the compound The distance between the compound 132 and the exciplex and the luminophore of the compound 132 is long. It is important to:

[0132] The compound according to one embodiment of the present invention has a luminophore and a protecting group as part of its structure, and In the case of 113, which functions as an energy acceptor, the protecting group may be a It has the function of increasing the distance between the donor and the luminophore. When a certain compound is used as compound 132 in this configuration, even if the concentration of compound 132 is increased, , the distance between the exciplex formed by Compound 131 and Compound 133 and Compound 132 This allows for a longer time, suppressing the energy transfer via the Dexter mechanism while allowing for the Forster mechanism. Therefore, in one aspect of the present invention, By using a certain compound as compound 132, S1 of compound 132 can be obtained from the exciplex. Level (S G ) (Route A6 and A7 in Figure 3(B)) Route A8) is more likely to occur, while the exciplex is more likely to evolve to the T1 level (T G ) Triplet excitation energy transfer to (Route A9: Energy transfer via the Dexter mechanism) This makes it difficult for this to occur, and suppresses the decrease in luminous efficiency that accompanies energy transfer along route A9. The light emitting efficiency of the light emitting device can be improved while suppressing the can be improved.

[0133] In this specification, the above-mentioned routes A6, A7, and A8 are ExSET (Exciplex-Singlet Energy Transfer) r) or ExEF (Exciplex-Enhanced Fluorescence That is, in the light-emitting layer 113 in this specification, the exciplex is converted into a fluorescent material. This shows that there is a donation of excitation energy.

[0134] <Emitting layer configuration example 3> In this example, the light-emitting layer 113 in the light-emitting device contains Compound 131, Compound 132, and and Compound 133, and Compound 131 and Compound 133 form an exciplex. Compound 132 is a compound having a structure in which a fluorescent material is used. The above configuration example 2 is a case where the compound The compound 133 is a phosphorescent material. It is preferable to use it as the compound 132, which is a light-emitting substance. An example of the correlation of the energy levels in the optical layer 113 is shown in FIG. The notations and symbols shown in FIG. 3(C) are the same as those in FIG. 3(B), and therefore will not be described again.

[0135] In this example, a compound having a heavy atom is used as one of the compounds forming the exciplex. Therefore, intersystem crossing between the singlet and triplet states is promoted. to form an exciplex that can transition from the nucleus to the singlet ground state (i.e., can exhibit phosphorescence). In this case, unlike ordinary exciplexes, the triplet excited energy of the exciplex is Energy level (T E ) is the energy donor level, so T E is a compound in which the compound is a light-emitting material The singlet excited energy level of 132 (S G ) or more. A tangent line is drawn at the short wavelength side of the emission spectrum of an exciplex using atoms, and the extrapolated line is The energy of the wavelength T E The energy of the wavelength of the absorption edge of the absorption spectrum of compound 132 is Ghee S G When this is done, T E ≧S G It is preferable that:

[0136] By using such a correlation of energy levels, the triplet excitation energy of the generated exciplex can be calculated. The triplet excited energy level (T E ) to the singlet excited energy of compound 132. Energy level (S G ) energy can be transferred to the S1 level (S E ) and T1 level (T E ) are adjacent energy levels, so the emission spectrum In some cases, it is difficult to clearly distinguish between fluorescence and phosphorescence. It may be possible to distinguish between fluorescence or phosphorescence by

[0137] The phosphorescent material used in the above configuration contains heavy atoms such as Ir, Pt, Os, Ru, and Pd. On the other hand, in this configuration example, the phosphorescent material acts as an energy donor. Therefore, the quantum yield can be either high or low. Allowed transitions are those in which energy transfer from the excited energy level to the singlet excited energy level of the guest material occurs. The above-mentioned exciplexes composed of phosphorescent materials or Energy transfer to the guest material occurs from the triplet excited energy level of the energy donor to the guest. Energy transfer to the singlet excited energy level of the substrate material (energy acceptor) This is a preferable configuration since it is an allowable transition.

[0138] Therefore, as shown in FIG. 3(C), in the light-emitting layer 113 of the light-emitting device shown in this configuration example, The triplet excitation energy of the exciplex is transferred via route A8 (route A7 in Figure 3(C)). The S1 level (S G) i.e., Route A The triplet excitation energy and singlet excitation energy are transferred to the S1 level of the guest material via route 6 and route A8. In Route A8, the exciplex can transfer excitation energy. Compound 132 functions as an energy acceptor, with the proviso that: In the light-emitting layer 113 of the light-emitting device shown in this configuration example, in addition to the above, triplet excited electrons of the exciplex are The energy transfers to the T1 level of compound 132 (Route A9 in Figure 3(C)). When such energy transfer (Route A9) occurs, the fluorescent substance Compound 132 cannot contribute triplet excitation energy to emission, so The luminous efficiency of the device decreases.

[0139] In order to suppress such energy transfer (route A9), The distance between compound 131 and compound 132, and the distance between compound 131 and compound 132 A long distance to the luminophore is important.

[0140] The compound according to one embodiment of the present invention has a luminophore and a protecting group as part of its structure, and In the case of 113, which functions as an energy acceptor, the protecting group may be a It has the function of increasing the distance between the donor and the luminophore. When a certain compound is used as compound 132 in this configuration, even if the concentration of compound 132 is increased, , the distance between the exciplex formed by Compound 131 and Compound 133 and Compound 132 This allows for a longer time, suppressing the energy transfer via the Dexter mechanism while allowing for the Forster mechanism. Therefore, in one aspect of the present invention, By using a certain compound as compound 132, S1 of compound 132 can be obtained from the exciplex. Level (S G ) (Route A6 and Route A8) While the exciplex is more likely to evolve into the T1 level (T G ) triplet excitation Energy transfer (Route A9: Energy transfer by the Dexter mechanism) is less likely to occur. It is possible to suppress the decrease in luminous efficiency due to the energy transfer of route A9 while emitting light. The light-emitting efficiency of the device can be increased, and the reliability of the light-emitting device can be improved. This can be done.

[0141] <Emitting layer configuration example 4> In this example, the light-emitting layer 113 in the light-emitting device is made of three types of materials, namely, compounds Compound 131, Compound 132, and Compound 133. 133 is a combination that forms an exciplex and functions as a light-emitting substance (guest material) The case where a fluorescent substance is used as compound 132 (when ExEF is used) is shown below. Therefore, the compound according to one embodiment of the present invention is a fluorescent substance, Compound 132. In this configuration example, it is preferable that the compound 133 is a material having TADF properties. This example differs from the example 3 in that it is made of a material other than ZnO. An example of the correlation of the energy levels is shown in FIG. 4(A). The components and symbols are the same as those in FIG. 3(B), and therefore will not be described again.

[0142] In this example, compound 133 is a TADF material and does not form an exciplex. Compound 133 converts triplet excitation energy into singlet excitation energy by upconversion. It has the function of converting energy (Route A in Figure 4(A) 10 ). Therefore, compound 1 The singlet excitation energy of 33 is rapidly transferred to compound 132 (Fig. 4(A) Route A 11 ). At this time, S C3 ≧S G It is preferable that:

[0143] Therefore, in the light-emitting layer 113 of the light-emitting device shown in this configuration example, the same as in the above-mentioned configuration example 3 Similarly, the triplet excitation energy is transferred to the guest via routes A6 to A8 in FIG. The route to the material compound 132 and route A in Figure 4(A) 10 and Route A1 There is a pathway that transfers the triplet excitation energy to compound 132 via 1. However, there are multiple pathways for the molecules to move to the fluorescent compound 132, which increases the luminescence efficiency. In Route A8, the exciplex is the energy donor and the Compound 132 functions as an energy acceptor. Route A 11 In the compound 1 Compound 33 acts as the energy donor, and compound 132 acts as the energy acceptor. However, in the light-emitting layer 113 of the light-emitting device shown in this configuration example, in addition to the above, a triplet structure of an exciplex is also used. The excitation energy of compound 132 is transferred to the T1 level (Route A in Figure 4(A)). When such an energy transfer (Route A9) occurs, the fluorescence emission The compound 132 cannot contribute triplet excitation energy to luminescence. This reduces the luminous efficiency of the light-emitting device.

[0144] In order to suppress such energy transfer (route A9), As shown in the figure, the exciplex formed by Compound 131 and Compound 133 and the exciplex formed by Compound 132 The distance between the exciplex formed by Compound 131 and Compound 133 and Compound 1 It is important that the distance between 32 and the luminophore is long.

[0145] The compound according to one embodiment of the present invention has a luminophore and a protecting group as part of its structure, and In the case of 113, which functions as an energy acceptor, the protecting group may be a It has the function of increasing the distance between the donor and the luminophore. When a certain compound is used as compound 132 in this configuration, even if the concentration of compound 132 is increased, , the distance between the exciplex formed by Compound 131 and Compound 133 and Compound 132 This allows for a longer time, suppressing the energy transfer via the Dexter mechanism while allowing for the Forster mechanism. Therefore, in one aspect of the present invention, By using a certain compound as compound 132, S1 of compound 132 can be obtained from the exciplex. Level (S G ) (Route A6 and Route A8) and the S1 level (S G Triplet excitation energy transfer to Part A 10 and Route A 11 ) are more likely to occur, while the exciplex gives rise to compound 13. T1 level of 2 (T G ) (Route A9: Dexter mechanism) This makes it difficult for the energy transfer along route A9 to occur. The luminous efficiency of the light-emitting device can be improved while suppressing the decrease in the luminous efficiency. The reliability of the light emitting device can be improved.

[0146] <Emitting layer configuration example 5> In this example, the light-emitting layer 113 in the light-emitting device is made of four types of materials, namely, compounds Compound 131, Compound 132, Compound 133, and Compound 134. 3 is a phosphorescent material that has the function of converting triplet excitation energy into light. In addition, Compound 131 and Compound 134 form exciplexes. Compound 132, which functions as a light-emitting material (guest material), is The case where a fluorescent substance is used will be described. Therefore, the compound according to one embodiment of the present invention is It is preferable to use the compound 132, which is a fluorescent substance. An example of the correlation of the energy levels in the light-emitting layer 113 is shown in FIG. The notations and symbols in FIG. 4(B) are the same as those in FIG. 3(B), Other than that, it is as follows: ·S C4 : S1 level of compound 134 T C4 : T1 level of compound 134

[0147] In this example, the compound 131 and the compound 134 form an exciplex. The S1 level of the body (S E ) and the T1 level of the exciplex (T E ) are adjacent energy levels (Root A in Figure 4(B)) 12 However, the above pathway is produced by two substances. When the formed exciplex loses its excitation energy, the two substances return to their original, separate forms. do.

[0148] Excitation energy levels of exciplexes (S E and TE ) is the compound that forms the exciplex. The S1 level (S C1 and S C4 ) is lower, so This allows the formation of excited states with lower excitation energies. The driving voltage of the sensor can be reduced.

[0149] In addition, compound 133 is a phosphorescent material, and therefore exhibits intersystem crossing between the singlet and triplet states. Therefore, the singlet and triplet excited energies are obtained from the exciplex. Both of these rapidly migrate to compound 133 (Route A 13 ). At this time, T E ≧T C3 It is preferable that:

[0150] The triplet excitation energy of compound 133 is 1 / 100 the singlet excitation energy of compound 132. converted to ghee (root A 14 At this time, as shown in Figure 4(B), T E ≧T C3 ≧S G In this case, energy transfer from compound 133 to compound 132 is efficient. More specifically, in the short wavelength tail of the phosphorescence spectrum of Compound 133, Draw a tangent line and calculate the energy of the wavelength of the extrapolated line as T C3 The absorption spectrum of compound 132 The energy of the wavelength at the absorption edge of the G When this is done, T C3 ≧S G It is preferable that: In addition, Route A 14 In the formula, compound 133 is the energy donor and compound 132 is the energy It acts as a ghee acceptor.

[0151] In this example, the combination of Compound 131 and Compound 134 forms an exciplex. Any combination is acceptable as long as it is possible to achieve this, but it is preferable that one of the compounds has a hole transporting property and the other is a compound having a hole transporting property. A compound having electron transport properties is more preferred.

[0152] In addition, as a combination of materials that efficiently form an exciplex, Compound 131 and Compound One of the HOMO levels is higher than the other, and one of the LUMO levels is It is preferable that the LUMO level is higher than the other LUMO level.

[0153] The correlation between the energy levels of compounds 131 and 134 is limited to that shown in Figure 4(B). That is, the singlet excited energy level (S C1 ) is compound 134 The singlet excited energy level (S C4 ) may be higher or lower than Compound 131. The triplet excited energy level (T C1 ) is the triplet excited energy level of compound 134 ( T C4 ) may be higher or lower.

[0154] In the light-emitting device of this configuration, the compound 131 preferably has a π-electron deficient skeleton. This structure lowers the LUMO level of compound 131, favoring the formation of an exciplex. It becomes suitable.

[0155] In the light-emitting device of this configuration, the compound 131 preferably has a π-electron-rich skeleton. This structure increases the HOMO level of compound 131, favoring the formation of an exciplex. It becomes suitable.

[0156] The compound according to one embodiment of the present invention has a luminophore and a protecting group as part of its structure, and In the case of 113, which functions as an energy acceptor, the protecting group may be a It has the function of increasing the distance between the donor and the luminophore. When a certain compound is used as compound 132 in this configuration, compound 133 and compound 132 Therefore, the compound according to one embodiment of the present invention can be prepared by By using compound 132 as a compound, the S1 level (S G ) to Triplet excitation energy transfer (Route A) 14 ) is more likely to occur, while The T1 level (T G Triplet excitation energy transfer (route) A 15 : Energy transfer by the Dexter mechanism) can be made difficult, A 15 The luminous efficiency of the light-emitting device is improved while suppressing the decrease in luminous efficiency due to the energy transfer of the It can be increased.

[0157] In addition, in this configuration example, by increasing the concentration of the compound 132, which is an energy acceptor, This suppresses the energy transfer by the Dexter mechanism while promoting the energy transfer by the Förster mechanism. The energy transfer rate can be increased. Increasing the transfer rate shortens the excited lifetime of the energy acceptor in the emissive layer. Therefore, the reliability of the light-emitting device can be improved. The concentration of compound 132 in the reaction mixture is 2 wt% or more relative to the energy donor compound 133. The content is preferably from 5 wt% to 50 wt%, more preferably from 5 wt% to 30 wt%, and even more preferably Or, it should be 5 wt% or more and 20 wt% or less.

[0158] In this specification, the above-mentioned Route A 12 and Route A 13 Regarding the route of ExT Also known as ET (Exciplex-Triplet Energy Transfer) That is, in the light-emitting layer 113 in this specification, the excited electrons from the exciplex to the compound 133 are This indicates that energy is being provided.

[0159] <Emitting layer configuration example 6> In this example, the light-emitting layer 113 in the light-emitting device is made of four types of materials, namely, compounds Compound 131, Compound 132, Compound 133, and Compound 134. 3 is a phosphorescent material that has the function of converting triplet excitation energy into light. In addition, Compound 131 and Compound 134 form exciplexes. Compound 132, which functions as a light-emitting material (guest material), is The case where a fluorescent substance is used will be described. Therefore, the compound according to one embodiment of the present invention is It is preferable to use the compound 132, which is a fluorescent substance. This structure differs from the above-described structure example 5 in that the compound 134 is a material having TADF properties. An example of the correlation of energy levels in the light-emitting layer 113 in this configuration is shown in FIG. 4(C). The notations and symbols shown in FIG. 4(C) are the same as those in FIG. 3(B) and FIG. 4(B). Therefore, the description is omitted.

[0160] In this example, compound 134 is a TADF material and does not form an exciplex. Compound 134 converts triplet excitation energy to singlet excitation energy by upconversion. It has the function of converting energy (Route A in Figure 4(C) 16). Therefore, compound 1 The singlet excitation energy of 34 is rapidly transferred to compound 132 (Fig. 4(C) Route A 17 ). At this time, S C4 ≧S G More specifically, the compound Draw a tangent line at the short wavelength side of the fluorescence spectrum of 134, and calculate the energy of the wavelength of the extrapolated line. Ghee S C4 The energy of the wavelength at the absorption edge of the absorption spectrum of compound 132 is S G and When you do this, S C4 ≧S G It is preferable that:

[0161] Therefore, in the light-emitting layer 113 of the light-emitting device shown in this configuration example, the same as in the above-mentioned configuration example 5 Similarly, Route A in Figure 4(C) 12 , Route A 13 , and root A 14 Through the triplet The pathway through which the excitation energy transfers to the guest material, compound 132, is shown in Figure 4(C). ToA 16 and Route A 17 There is a pathway that leads to compound 132 via There are multiple pathways through which triplet excitation energy can be transferred to the fluorescent compound 132. By doing so, the luminous efficiency can be further improved. 14 In the compound 133 Compound 132 acts as an energy acceptor. Part A 17 In this case, compound 134 is the energy donor and compound 132 is the energy accessor. However, in the light-emitting layer 113 of the light-emitting device shown in this configuration example, In addition, the triplet excitation energy of compound 133 is transferred to the T1 level of compound 132. Route A in Figure 4(C)15 ) can also compete with this kind of energy transfer (route). A 15 ) occurs, the fluorescent material Compound 132 emits triplet excitation energy. Since the luminous efficiency of the light emitting device is reduced, the luminous efficiency of the light emitting device is reduced.

[0162] Such energy transfer (Route A) 15 ) is suppressed, As mentioned above, the distance between compound 133 and compound 132, that is, the distance between compound 133 and compound 132, It is important that the distance between the luminophore and the molecule is long.

[0163] The compound according to one embodiment of the present invention has a luminophore and a protecting group as part of its structure, and In the case of 113, which functions as an energy acceptor, the protecting group may be a It has the function of increasing the distance between the donor and the luminophore. When a certain compound is used as compound 132 in this configuration, even if the concentration of compound 132 is increased, The distance between compound 133 and compound 132 can be increased, and the Dexter mechanism It is possible to suppress energy transfer while increasing the energy transfer rate via the Förster mechanism. Therefore, by using the compound according to one embodiment of the present invention as compound 132, From the exciplex, the S1 level (S G ) triplet excitation energy Gee Movement (Route A 12 and Route A 13 and Root A 14 ) and the compound 132 S1 level (S G Triplet excitation energy transfer to (Route A) 16 and Route A 17) are more likely to occur, while the T1 level (T G Triplet excitation energy transfer to (Route A) 15 Energy transfer by the Dexter mechanism This makes it difficult for Route A to occur. 15 The decrease in luminescence efficiency due to the energy transfer The light emitting efficiency of the light emitting device can be improved while suppressing the deterioration of the light emitting device. Reliability can be improved.

[0164] <Emitting Layer Configuration Example 7> In this example, the light-emitting layer 113 in the light-emitting device contains Compound 131, Compound 132, and and Compound 133. Compound 133 converts triplet excitation energy into luminescence. In this example, a phosphorescent material is used as a material having the function of emitting light. When a fluorescent material is used as compound 132 functioning as a light-emitting material (guest material), Therefore, the compound according to one embodiment of the present invention is a fluorescent substance, Compound 1. It is preferable to use it as 32. In this example, the energy An example of the correlation between the levels is shown in FIG. 5(A). The symbols and symbols are as follows: ·Comp(131): Compound 131 ·Comp(133): Compound 133 ·Guest(132): Compound 132 ·S C1 : S1 level of compound 131 T C1 :T1 level of compound 131 T C3 :T1 level of compound 133 T G :T1 level of compound 132 ·S G : S1 level of compound 132

[0165] In this example, carrier recombination occurs mainly in compound 131, resulting in a single Compound 133 is T C3 ≦T C1 That By selecting a phosphorescent material with a high affinity, the singlet excitation energy generated in compound 131 can be The T of compound 133 was calculated by comparing both the singlet and triplet excitation energies. C3 can be moved to a higher level (Route A in Figure 5(A)) 18 ) Some carriers also recombine with Compound 133. possible.

[0166] The phosphorescent material used in the above configuration contains heavy atoms such as Ir, Pt, Os, Ru, and Pd. When a phosphorescent material is used as compound 133, the energy donor The triplet excited energy level of the guest material (energy acceptor) is converted to the singlet excited state. Energy transfer to the energy level is favorable because it is an allowed transition. The triplet excitation energy of 3 is expressed as Root A 19 The S1 level (S G ) Route A can be moved to 19 In the formula, compound 133 is an energy donor, Compound 132 acts as an energy acceptor. In this case, T C3 ≧S G is The excitation energy of compound 133 is efficiently transferred to the singlet excitation of the guest material, compound 132. Specifically, the phosphorescence spectrum of compound 133 is shifted to the short wavelength side. Draw a tangent at the tail of and define the wavelength energy of the extrapolated line as T C3 Compound 132 The energy of the wavelength at the absorption edge of the absorption spectrum is S G When this is done, T C3 ≧S G Being However, in the light-emitting layer 113 of the light-emitting device shown in this configuration example, in addition to the above, The triplet excitation energy of compound 133 is transferred to the T1 level of compound 132 (Figure 5(A)). ) Root A 20 ) can also compete with this energy transfer (Route A). 20 ) is born In this case, the fluorescent material, Compound 132, contributes triplet excitation energy to the emission. This reduces the light emitting efficiency of the light emitting device.

[0167] Such energy transfer (Route A) 20 ) is suppressed, As mentioned above, the distance between compound 133 and compound 132, that is, the distance between compound 133 and compound 132, It is important that the distance between the luminophore and the molecule is long.

[0168] The compound according to one embodiment of the present invention has a luminophore and a protecting group as part of its structure, and In the case of 113, which functions as an energy acceptor, the protecting group may be a It has the function of increasing the distance between the donor and the luminophore. When a certain compound is used as compound 132 in this configuration, even if the concentration of compound 132 is increased, The distance between compound 133 and compound 132 can be increased, and the Dexter mechanism To increase the rate of energy transfer via the Förster mechanism while suppressing energy transfer. Therefore, the compound according to one embodiment of the present invention can be used as compound 132. The S1 level (S G ) of triplet excitation energy Energy Transfer (Route A 19 ) is more likely to occur, while compound 133 to compound 13 T1 level of 2 (T G Triplet excitation energy transfer to (Route A) 20 :Dexter mechanism This makes it difficult for route A to occur. 20 Energy transfer The light-emitting efficiency of the light-emitting device can be improved while suppressing the decrease in light-emitting efficiency that accompanies the light-emitting device. In addition, the reliability of the light emitting device can be improved.

[0169] <Emitting Layer Configuration Example 8> In this example, the light-emitting layer 113 in the light-emitting device contains Compound 131, Compound 132, and and Compound 133. Compound 133 converts triplet excitation energy into luminescence. This section explains the case where a material with TADF properties is used as a substance with this function. In addition, a fluorescent material is used as the compound 132 that functions as a light-emitting material (guest material). Therefore, the compound of one embodiment of the present invention is a fluorescent substance. It is preferable to use the compound 132 as the light-emitting layer 113 in this example. An example of the correlation of the energy levels is shown in FIG. 5(B). The notations and symbols in the figure are the same as those in Figure 5(A), and the rest are as follows: As shown. ·S C3 : S1 level of compound 133

[0170] In this example, carrier recombination occurs mainly in compound 131, resulting in a single Compound 133 is S C3 ≦S C1 KatsuT C3 ≦TC1 By selecting a material with TADF properties that satisfy the following relationship, compound 13 Both the singlet and triplet excitation energies generated in 1 were converted to S of compound 133. C 3 and T C3 It is possible to move to the next level (Route A in Figure 5(B) 21 ). In addition, some The carrier can also be recombined with compound 133.

[0171] In addition, since compound 133 is a material with TADF properties, it can increase triplet excitation energy. It has the function of converting it into singlet excitation energy by photoconversion (Fig. 5(B) Route A 22 In addition, the singlet excitation energy of compound 133 rapidly dissociates into the compound. It is possible to move to the object 132 (Route A in FIG. 5(B) 23 ). At this time, S C3 ≧ S G More specifically, it is preferable that the fluorescence spectrum of Compound 133 is at the short wavelength side. Draw a tangent at and calculate the wavelength energy of the extrapolated line as S C3 and the absorption of compound 132 The energy of the wavelength at the absorption edge of the spectrum is S G When this is done, S C3 ≧S G It is preferable to be I wish.

[0172] Therefore, in the light-emitting layer 113 of the light-emitting device shown in this configuration example, ToA 21 , Route A 22 , and root A 23 By taking the following route, compound 133 The triplet excitation energy can be converted into the fluorescent emission of compound 132. In 3, compound 133 is the energy donor and compound 132 is the energy acceptor. However, in the light-emitting layer 113 of the light-emitting device shown in this configuration example, in addition to the above, The triplet excitation energy of compound 133 is transferred to the T1 level of compound 132 (Figure 5 (B) Route A 24 ) can also compete with this energy transfer (Route A). 24 ) When this occurs, the fluorescent substance Compound 132 contributes triplet excitation energy to light emission. This reduces the luminous efficiency of the light-emitting device.

[0173] Such energy transfer (Route A) 24 ) is suppressed, As mentioned above, the distance between compound 133 and compound 132, that is, the distance between compound 133 and compound 132, It is important that the distance between the luminophore and the molecule is long.

[0174] The compound according to one embodiment of the present invention has a luminophore and a protecting group as part of its structure, and In the case of 113, which functions as an energy acceptor, the protecting group may be a It has the function of increasing the distance between the donor and the luminophore. When a certain compound is used as compound 132 in this configuration, even if the concentration of compound 132 is increased, The distance between compound 133 and compound 132 can be increased, and the Dexter mechanism It is possible to suppress energy transfer while increasing the energy transfer rate via the Förster mechanism. Therefore, by using the compound according to one embodiment of the present invention as compound 132, From the above, the S1 level (S G ) to triplet excitation energy Energy Transfer (Route A 23 ) is more likely to occur, while compound 133 to compound 132 T1 level (TG Triplet excitation energy transfer to (Route A) 24 :Dexter mechanism This makes it difficult for the energy transfer due to the 24 of energy The light-emitting efficiency of the light-emitting device can be increased while suppressing the decrease in light-emitting efficiency due to movement. In addition, the reliability of the light-emitting device can be improved.

[0175] (Embodiment 3) In this embodiment, a light-emitting device according to one embodiment of the present invention will be described.

[0176] <Example of light-emitting device configuration> FIG. 6A shows an example of a light-emitting device having an EL layer including a light-emitting layer between a pair of electrodes. Specifically, the EL layer 103 is sandwiched between a first electrode 101 and a second electrode 102. In addition, when the first electrode 101 is used as an anode, the EL layer 103 has a structure in which holes (Hole) injection layer 111, hole transport layer 112, light emitting layer 113, electron transport layer 11 The light-emitting layer 11 has a structure in which the light-emitting layer 11 and the electron injection layer 115 are sequentially stacked as functional layers. The third organic compound 123 is a host material and a guest material. As a guest material, a material that converts singlet excitation energy into light emission (fluorescent a first organic compound 121, which is a photoluminescent material, and a compound that converts triplet excitation energy into light emission; A second organic compound 122, which is a functional material (phosphorescent material or TADF material), Use.

[0177] Another example of the structure of a light-emitting device is a device formed by sandwiching a charge generating layer between a pair of electrodes. By using a structure with multiple EL layers (tandem structure), low voltage operation is possible. Light-emitting devices or devices that form a micro-optical resonator (microcavity) structure between a pair of electrodes A light-emitting device or the like having improved optical properties by using the above-mentioned method is also included in one aspect of the present invention. When a voltage is applied between the first electrode 101 and the second electrode 102, the charge generating layer It has the function of injecting electrons into one adjacent EL layer and injecting holes into the other EL layer.

[0178] At least one of the first electrode 101 and the second electrode 102 of the light-emitting device is transparent. The electrode has optical properties (transparent electrode, semi-transparent / semi-reflective electrode, etc.). In the case of a transparent electrode, the visible light transmittance of the transparent electrode is 40% or more. In the case of a semi-transmissive / semi-reflective electrode, the reflectance of the semi-transmissive / semi-reflective electrode for visible light is preferably 20% or more and 80% or less. The resistivity of these electrodes is 1×10 -2 Ωcm It is preferable to have the following:

[0179] In the light-emitting device according to one embodiment of the present invention, the first electrode 101 and the second electrode When one of the electrodes 102 is a reflective electrode, the reflective electrode The reflectance of visible light is 40% or more and 100% or less, preferably 70% or more and 100% or less. In addition, the resistivity of this electrode is 1×10 -2 It is preferable to set it to Ωcm or less.

[0180] <First Electrode and Second Electrode> The materials for forming the first electrode 101 and the second electrode 102 are selected from those having the above-mentioned functions of both electrodes. If the requirements are met, the following materials can be used in combination. For example, metals, alloys, electrically conductive compounds, and mixtures thereof can be used appropriately. Specifically, In-Sn oxide (also called ITO), In-Si-Sn oxide (IT SO), In-Zn oxide, and In-W-Zn oxide. Aluminum (Al), Titanium (Ti), Chromium (Cr), Manganese (Mn), Iron (Fe), Cobalt (Co), Nickel (Ni), Copper (Cu), Gallium (Ga), Zinc (Zn), Indium (In), tin (Sn), molybdenum (Mo), tantalum (Ta), tungsten Tin (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium Metals such as yttrium (Y), neodymium (Nd), and alloys containing these in appropriate combinations are used. In addition, elements belonging to Group 1 or Group 2 of the periodic table that are not listed above can also be used. Elements (e.g., lithium (Li), cesium (Cs), calcium (Ca), strontium rare earth metals such as strontium (Sr), europium (Eu), ytterbium (Yb) and An alloy containing an appropriate combination of these, graphene, etc. may also be used.

[0181] These electrodes can be fabricated by sputtering or vacuum deposition.

[0182] <Hole injection layer> The hole injection layer 111 injects holes from the first electrode 101, which is an anode, into the EL layer 103. The layer is an injection layer, and contains an organic acceptor material or a material with high hole injection properties. .

[0183] The organic acceptor material is an organic compound whose LUMO level and HOMO level are close to each other. By separating charges between the organic compound and the material, holes are generated in the organic compound. Therefore, the organic acceptor material is a quinodimethane derivative, Electron-withdrawing groups (halogens) such as chloranil derivatives or hexaazatriphenylene derivatives Compounds having a 7,7,8,8-tetramethyl group or a cyano group can be used. tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ), 3,6-Difluoro-2,5,7,7,8,8-hexacyanoquinodimethane, chloranil , 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaaza Triphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8-hexafluorotetrafluoroethylene For example, cyclohexyl naphthoquinodimethane (abbreviation: F6-TCNNQ) can be used. Among organic acceptor materials, HAT-CN has particularly high acceptor properties and is resistant to heat. In addition, the [3] radialene derivative has an electron-accepting function. It is preferred because it has very high tolerance, specifically α,α',α''-1,2,3-cyclopropyl Pantriylidene tris[4-cyano-2,3,5,6-tetrafluorobenzeneacetate nitrile], α,α',α''-1,2,3-cyclopropanetriylidenetris[2, 6-Dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile α,α',α''-1,2,3-cyclopropanetriylidenetris[2,3,4 , 5,6-pentafluorobenzeneacetonitrile], etc. can be used.

[0184] Materials with high hole injection properties include molybdenum oxide, vanadium oxide, ruthenium oxide, and transition metal oxides such as aluminum oxide, tungsten oxide, or manganese oxide; In addition, phthalocyanine (abbreviated as HPc) or copper phthalocyanine (abbreviated as CuPc ) and other phthalocyanine compounds can be used.

[0185] In addition to the above materials, we also developed a low molecular weight compound, 4,4',4''-tris(N,N-diphenyl)propanol. (phenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[ N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTD ATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamine] N,N'-bis[4-[bis(3-methylphenyl )amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'- Diamine (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl) 3-[N-(9-phenyl)-N-phenylamino]benzene (abbreviation: DPA3B), [N-(4-amino-1-phenyl-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation :PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N -phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N- (1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenyl Aromatic amine compounds such as dicarbazole (abbreviated as PCzPCN1) can be used. Cut.

[0186] In addition, poly(N-vinyl alcohol), which is a polymer compound (oligomer, dendrimer, polymer, etc.), Poly(4-vinyltriphenylamine) (abbreviation: P VTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl]phenyl] (Nyl-N'-phenylamino)phenyl methacrylamide] (abbreviation: PTPDMA), Poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] ] (abbreviation: Poly-TPD), etc. can be used. PEDOT / PSS) / poly(styrenesulfonic acid) Acid-added polymers such as polyaniline / poly(styrene sulfonic acid) (PAni / PSS) It is also possible to use a diol-based compound, etc.

[0187] In addition, materials with high hole injection properties include hole transport materials and acceptor materials (electron acceptor materials). In this case, a composite material containing an acceptor material can be used. Electrons are extracted from the hole transport material, generating holes in the hole injection layer 111, and the holes are transported to the hole transport layer 11 Holes are injected into the light-emitting layer 113 through the hole-injecting layer 111. Alternatively, the layer may be formed of a single layer of a composite material containing a metal oxide and an acceptor material (electron-accepting material). However, the hole transport material and the acceptor material (electron acceptor material) are stacked in separate layers. It may be formed in layers.

[0188] The hole transport material is 1×10 -6 cm 2 / Vs or higher hole mobility In addition, other materials that have a higher hole transporting property than electron transporting property can be used. It can be used.

[0189] As the hole transport material, π-electron-rich heteroaromatic compounds (e.g., carbazole derivatives or or furan derivatives), or aromatic amines (compounds with an aromatic amine skeleton), etc. Materials with high transport properties are preferred.

[0190] The carbazole derivatives (compounds having a carbazole skeleton) include bicarbazole azole derivatives (e.g., 3,3'-bicarbazole derivatives), aromatic compounds having a carbazolyl group, aromatic amines and the like.

[0191] Furthermore, the bicarbazole derivative (for example, 3,3'-bicarbazole derivative) may be Specifically, 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP ), 9,9'-bis(1,1'-biphenyl-4-yl)-3,3'-bi-9H-carba 9,9'-bis(1,1'-biphenyl-3-yl)-3,3'-bi-9H-carbazol Rubazole, 9-(1,1'-biphenyl-3-yl)-9'-(1,1'-biphenyl -4-yl)-9H,9'H-3,3'-bicarbazole (abbreviation: mBPCCBP), -(2-naphthyl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation :βNCCP) and others.

[0192] Specific examples of the aromatic amine having a carbazolyl group include 4-phenyl- 4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: P CBA1BP), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluorene -2-yl)-9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazo] [(3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation :PCBBiF), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole) PCBBi1BP), 4-(1-naphthyl-3-yl)triphenylamine -4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbamoyl) PCBNBB, 4-phenyldiphenyl Nyl-(9-phenyl-9H-carbazol-3-yl)amine (abbreviation: PCA1BP) , N,N'-bis(9-phenylcarbazol-3-yl)-N,N'-diphenylbenzene zene-1,3-diamine (abbreviation: PCA2B), N,N',N''-triphenyl-N, N',N''-tris(9-phenylcarbazol-3-yl)benzene-1,3,5- Triamine (abbreviation: PCA3B), 9,9-dimethyl-N-phenyl-N-[4-(9- Phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl] (phenyl)phenyl]spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenyl Nylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole)]

[0043] PCz PCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl )amino]-9-phenylcarbazole (abbreviation: PCzPCN1), 3-[N-(4-di phenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA1), 3,6-bis[N-(4-diphenylaminophenyl)-N-phenyl 3,6-bis[N- (4-diphenylaminophenyl)-N-(1-naphthyl)amino]-9-phenylcarbamoyl PCzTPN2, 2-[N-(9-phenylcarbazol-3-yl )-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: PCASF), N- [4-(9H-carbazol-9-yl)phenyl]-N-(4-phenyl)phenyl Niline (abbreviation: YGA1BP), N,N'-bis[4-(carbazol-9-yl)phenyl] N,N'-diphenyl-9,9-dimethylfluorene-2,7-diamine (abbreviation :YGA2F), 4,4',4''-tris(carbazol-9-yl)triphenyl Min (abbreviated as TCTA) and others.

[0193] In addition to the above, the carbazole derivatives include 3-[4-(9-phenanthryl) -phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn), 3-[4-( 1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)benzene 3,6-bis(3,5-diphenylphenyl)bis(3,6-diphenylbenzoyl)biphenyl (abbreviation: CBP) -9-phenylcarbazole (abbreviation: CzTP), 1,3,5-tris[4-(N-calcium phosphate] 9-[4-(10-phenyl-9-(4-(10-phenyl-4-phenyl)phenyl)benzene (abbreviation: TCPB) anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), and the like.

[0194] Specific examples of the furan derivatives (compounds having a furan skeleton) include 4,4' ,4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: D BT3P-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-phenyldibenzothiazolinone Compounds with a thiophene skeleton, such as thiophene (abbreviated as DBTFLP-IV), 4,4' ,4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF 3P-II), 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II), and the like.

[0195] Specific examples of the aromatic amine include 4,4'-bis[N-(1-naphthyl) -N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis (3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4' -diamine (abbreviation: TPD), 4,4'-bis[N-(spiro-9,9'-bifluorene -2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), 4-phenyl-4 '-(9-Phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP) , 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation Name: mBPAFLP), N-(9,9-dimethyl-9H-fluoren-2-yl)-N- {9,9-dimethyl-2-[N'-phenyl-N'-(9,9-dimethyl-9H-fluoro Fluoren-2-yl)amino]-9H-fluoren-7-yl}phenylamine (abbreviation: DF LADFL), N-(9,9-dimethyl-2-diphenylamino-9H-fluorene-7 -yl)diphenylamine (abbreviation: DPNF), 2-[N-(4-diphenylaminophenyl) N-phenylamino)spiro-9,9'-bifluorene (abbreviation: DPASF), 2,7-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]-spiro -9,9'-bifluorene (abbreviation: DPA2SF), 4,4',4''-tris[N-( 1-Naphthyl-N-phenylamino]triphenylamine (abbreviation: 1'-TNATA) , 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenyl Amino]triphenylamine (abbreviation: m-MTDATA), N,N'-di(p-tolyl) -N,N'-diphenyl-p-phenylenediamine (DTDPPA), 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'-diamine (abbreviation: DN TPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenyl amino]benzene (abbreviation: DPA3B), etc.

[0196] As hole transport materials, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4 -vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4- (4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)meth acrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl) -N,N'-bis(phenyl)benzidine (abbreviation: Poly-TPD) A mixture can also be used.

[0197] However, the hole transport material is not limited to the above, and one or more of various known materials may be used. A combination of these may be used as the hole transport material.

[0198] Acceptor materials used in the hole injection layer 111 include those of Group 4 to 5 in the periodic table. Oxides of metals belonging to Group 8 can be used. Specifically, molybdenum oxide, Vanadium, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide Among them, molybdenum oxide is particularly stable in the atmosphere and is easily absorbed. It is preferable because it has low moisture content and is easy to handle. In addition, the above-mentioned organic acceptor can be used. It is also possible.

[0199] The hole injection layer 111 can be formed by using various known film formation methods. For example, it can be formed by using a vacuum deposition method.

[0200] <Hole transport layer> The hole transport layer 112 transports holes injected from the first electrode 101 by the hole injection layer 111. The hole transport layer 112 is a layer that transports the electrons to the light emitting layer 113. The hole transport layer 112 contains a hole transport material. Therefore, the hole transport layer 112 is a layer containing holes that can be used in the hole injection layer 111. A transportable material can be used.

[0201] In the light-emitting device according to one embodiment of the present invention, the same organic compound as that of the hole-transport layer 112 It is preferable to use the same organic compound for the hole transport layer 112 and the light emitting layer 113. By using the compound, holes can be efficiently transported from the hole transport layer 112 to the light emitting layer 113. This is to ensure that

[0202] <Light-emitting layer> The light-emitting layer 113 is a layer containing a light-emitting substance. The light-emitting layer 113 has a host material and a guest material. Compound 123 was used as a guest material, which has the function of converting singlet excitation energy into luminescence. The first organic compound 121 is a material (fluorescent material) that emits triplet excitation energy. The second organometallic material is a material with the function of converting light (phosphorescent material or TADF material). The light-emitting material that can be used for the light-emitting layer 113 is the compound 122. As long as the above conditions are met, there are no particular limitations, and colors such as blue, purple, blue-purple, green, yellow-green, yellow, orange, and red are acceptable. Any substance that emits any luminescent color can be used as appropriate.

[0203] However, as the host material used in the light-emitting layer 113, multiple types of organic compounds may be used. Furthermore, the compound may be an exciplex formed by these compounds. The third organic compound 123 is a compound similar to the first organic compound 121 or the second organic compound 122 used as a guest material. A substance with an energy gap larger than that of organic compound 122 It is preferable to use the lowest singlet excited energy level of the third organic compound 123. (S1 level) is higher than the S1 level of the first organic compound 121, and The lowest triplet excited energy level (T1 level) of 3 is the T1 level of the first organic compound 121. The lowest triplet excitation energy of the third organic compound 123 is preferably higher than The level (T1 level) is preferably higher than the T1 level of the second organic compound 122.

[0204] The one or more organic compounds used as the host material may be the same as those used in the light-emitting layer. If the conditions as a host material are satisfied, the hole transport layer 112 can be used. transporting material, or an electron transporting material that can be used in the electron transport layer 114 described later, etc. The organic compounds may be exciplexes made up of a plurality of organic compounds. Excited complexes (exciplexes) that form excited states with multiple organic compounds The difference between the S1 and T1 levels is extremely small, As a TADF material capable of converting triplet excitation energy into singlet excitation energy, In addition, the combination of multiple organic compounds that form exciplexes is For example, one of the aromatic rings has a π-electron deficient heteroaromatic ring, and the other has a π-electron rich heteroaromatic ring. As a combination for forming an exciplex, it is preferable to use iridium and rhodium on one side. Alternatively, phosphorescent materials such as platinum-based organometallic complexes or metal complexes may be used.

[0205] The first organic compound 121 and the second organic compound 122 used as guest materials in the light-emitting layer 113 are It is preferable that the organic compounds 122 each emit a different light color. White light may be emitted by combining luminescent colors that are related in color.

[0206] The first guest material of the light-emitting layer 113 is a compound that converts singlet excitation energy into light. The first organic compound 121, which is a material having the function of forming a light-emitting layer, is used as a guest material in the light-emitting layer. The materials shown in Embodiment 2 can be used in combinations that satisfy all of the conditions. It is also the second guest material in the light-emitting layer 113, which converts triplet excitation energy into light emission. The second organic compound 122, which is a material having a function of emitting phosphorescence, may be, for example, a phosphorescent material. The thermally activated delayed fluorescence (TDF) is a material that exhibits thermally activated delayed fluorescence (TDF). y activated delayed fluorescence (TADF) material These are also combinations that satisfy the conditions for use as guest materials in the light-emitting layer. The lowest singlet excited energy of the first organic compound 121 can be The S1 level of the second organic compound 122 is higher than the T1 level of the second organic compound 122. The light emitted from the second organic compound 122 is stronger than the light emitted from the first organic compound 121. The peak wavelength of the emission spectrum is longer than that of the other two.

[0207] Phosphorescent materials are materials that emit light in the temperature range above low temperature (e.g., 77K) and below room temperature (i.e., above 77K). A compound that exhibits phosphorescence but does not exhibit fluorescence at either of the following temperatures: The phosphorescent material preferably contains a metal element with a large spin-orbit interaction. Examples of suitable complexes include organic metal complexes, metal complexes (platinum complexes), and rare earth metal complexes. Transition metal elements are preferred, particularly platinum group elements (ruthenium (Ru), rhodium (Rh), platinum radium (Pd), osmium (Os), iridium (Ir), or platinum (Pt) It is preferable that the compound has iridium, and in particular, the compound has iridium, which allows the compound to have a singlet ground state and a triplet excited state. This is preferable because it can increase the transition probability involved in direct transitions between states.

[0208] It has a blue or green color and the peak wavelength of the emission spectrum is between 450 nm and 570 nm. Some phosphorescent materials include the following:

[0209] For example, tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl )-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium (III) (abbreviation: [Ir(mpptz-dmp)3]), tris(5-methyl-3,4 -diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir (Mptz)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl [Ir(iPrp)] tz-3b)3]), tris[3-(5-biphenyl)-5-isopropyl-4-phenyl [Ir(iPr5 btz)3]), organometallic complexes with a 4H-triazole skeleton, such as tris[3- Methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato ]iridium(III) (abbreviation: [Ir(Mptz1-mp)3]), tris(1-methyl Iridium(II) I) (abbreviation: [Ir(Prtz1-Me)3]) Organometallic complexes containing fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl]propanol [phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpmi)3 ]), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f] [Ir(dmpimpt-Me)3 organometallic complexes with imidazole skeletons, such as bis[2-(4',6'-difluoromethyl] (O-phenyl)pyridinato-N,C 2’ ]iridium(III) tetrakis(1-pyrazoline) aryl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pi Lysinato-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) Acetylacetonate (abbreviation: FIr(acac)) Examples of suitable organometallic complexes include those having phenylpyridine derivatives as ligands.

[0210] It is green or yellow and the peak wavelength of the emission spectrum is between 495 nm and 590 nm. Some phosphorescent materials include the following:

[0211] For example, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation :[Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)i Lithium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bis(trimethylsilyl) Bis(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(m ppm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4 -phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(a cac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenyl [Pyrimidinato]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]) , (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenyl [Ir(mpmppm)2(acac) ]), (acetylacetonato)bis{4,6-dimethyl-2-[6-(2,6-dimethyl phenyl)-4-pyrimidinyl-κN3]phenyl-κC}iridium(III) (abbreviation :[Ir(dmppm-dmp)2(acac)]), (acetylacetonato)bis(4 ,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2( organometallic iridium complexes with pyrimidine skeletons, such as (acetyl acac)] cetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III)( Abbreviation: [Ir(mppr-Me)2(acac)]), (acetylacetonato)bis(5 -isopropyl-3-methyl-2-phenylpyrazinato)iridium(III) (abbreviation: Organometallic pyrazine skeletons such as [Ir(mppr-iPr)2(acac)] Iridium complex, tris(2-phenylpyridinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(ppy)3]), bis(2-phenylpyridinato-N,C 2’ ) Iriji Ir(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), (benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: [I r(bzq)2(acac)]), tris(benzo[h]quinolinato)iridium(II I) (abbreviation: [Ir(bzq)3]), tris(2-phenylquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(pq)3]), bis(2-phenylquinolinato- N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(pq)2(a cac)]), bis[2-(2-pyridinyl-κN)phenyl-κC][2-(4-phenyl [Ir( ppy)2(4dppy)]), bis[2-(2-pyridinyl-κN)phenyl-κC] [2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC] Organometallic iridium complexes with pyridine skeletons, bis(2,4-diphenyl-1,3-o Xazolato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir( dpo)2(acac)]), bis{2-[4'-(perfluorophenyl)phenyl] Pyridinato-N,C 2’}Iridium(III) acetylacetonate (abbreviation: [Ir( p-PF-ph)2(acac)]), bis(2-phenylbenzothiazolato-N,C 2 ’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(bt)2(acac) ]), as well as organometallic complexes such as tris(acetylacetonato)(monophenanthroline) Rare earth metals such as terbium(III) (abbreviated as [Tb(acac)3(Phen)]) Examples include complexes of the aryl group.

[0212] Yellow or red, with a peak wavelength of 570 nm or more and 750 nm or less in the emission spectrum. Some phosphorescent materials include the following:

[0213] For example, (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(III) (abbreviation: [Ir(5mdppm)2(dpm)]), (dipivaloylmethyl Thanato)bis[4,6-di(naphthalen-1-yl)pyrimidinato]iridium(III ) (abbreviation: [Ir(d1npm)2(dpm)]) Metal complex, (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridide Ir(tppr)2(acac)], bis(2,3,5-trimethylsilyl) (triphenylpyrazinate)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir (tppr)2(dpm)]), bis{4,6-dimethyl-2-[3-(3,5-dimethyl {(2,6-dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC} ... thyl-3,5-heptanedionate-κ 2 O,O')iridium(III) (abbreviation: [Ir (dmdppr-P)2(dibm)]), bis{4,6-dimethyl-2-[5-(4- Cyano-2,6-dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazine {(2,2,6,6-tetramethyl-3,5-heptanedioic acid)-N-phenyl-κC}(2,2,6,6-tetramethyl-3,5-heptanedioic acid) Nat-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmdppr-dmCP) 2(dpm)]), bis[2-(5-(2,6-dimethylphenyl)-3-(3,5-di methylphenyl)-2-pyrazinyl-κN)-4,6-dimethylphenyl-κC](2, 2',6,6'-Tetramethyl-3,5-heptanedionato-κ 2 O,O') Iridium (III) (abbreviation: [Ir(dmdppr-dmp)2(dpm)]), (acetylacetone) N,C quinoxalinato)bis[2-methyl-3-phenylquinoxalinato-N,C 2’ ]Iridium (I II) (abbreviation: [Ir(mpq)2(acac)]), (acetylacetonato)bis(2 ,3-Diphenylquinoxalinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir( dpq)2(acac)]), (acetylacetonato)bis[2,3-bis(4-fluoro [Ir(Fdpq)2(a organometallic complexes with a pyrazine skeleton, such as tris(1-phenylisoxazone) Norinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(piq)3]), bis( 1-Phenylisoquinolinato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(piq)2(acac)]), bis[4,6-dimethyl-2-(2-oxo- N-phenyl-κC](2,4-pentanedionato-κ) 2 O,O') Iriji Pyridine skeleton, such as Ir(III) (abbreviation: [Ir(dmpqn)2(acac)]) Organometallic complexes having 2,3,7,8,12,13,17,18-octaethyl-21 Platinum complexes such as H,23H-porphyrin platinum(II) (abbreviation: [PtOEP]), Tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)eu Eu(DBM)3(Phen) (2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline) Rare earth metal complexes such as boropium(III) (abbreviation: [Eu(TTA)3(Phen)]) The body is mentioned.

[0214] The following materials can be used as TADF materials: , the difference between the S1 level and the T1 level is small (preferably 0.2 eV or less), and the triplet excited state can be upconverted to a singlet excited state (reverse intersystem crossing) by a small amount of thermal energy. It is a material that efficiently emits light (fluorescence) from the singlet excited state. The conditions for efficient activation delayed fluorescence are that the triplet excited energy level and the singlet excited energy level are The energy difference between the excitation energy levels is 0 eV or more and 0.2 eV or less, preferably 0 eV or more and 0 0.1 eV or less. In addition, delayed fluorescence in TADF materials is usually It is a type of luminescence that has a spectrum similar to that of fluorescence, but has a significantly longer lifespan. x10 -6 seconds or more, preferably 1 x 10 -3 More than a second.

[0215] Examples of TADF materials include fullerenes or their derivatives, and acrylic compounds such as proflavine. In addition, magnesium (Mg), zinc (Zn), calcium Cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium Examples of metal-containing porphyrins include those containing palladium (Pd). For example, protoporphyrin-tin fluoride complex (abbreviated as SnF2 (Proto IX )), mesoporphyrin-tin fluoride complex (abbreviation: SnF2(Meso IX)), hema Hematoporphyrin-tin fluoride complex (abbreviation: SnF2(Hemato IX)), copropion Lupyrrin tetramethyl ester-tin fluoride complex (abbreviated as SnF2(Copro II) I-4Me), octaethylporphyrin-tin fluoride complex (abbreviated as SnF2(OEP )), etioporphyrin-tin fluoride complex (abbreviation: SnF2(Etio I)), octadecanoic acid Examples include tetraethylporphyrin-platinum chloride complex (abbreviation: PtCl2OEP).

[0216] [ka]

[0217] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[ 2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-T RZ), 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-diphenyl 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 4-(9'-cridin-9,9'-anthracen]-10'-one (abbreviation: ACRSA), -phenyl-3,3'-bi-9H-carbazol-9-yl)benzofuro[3,2-d] Pyrimidine (abbreviation: 4PCCzBfpm), 4-[4-(9'-phenyl-3,3'-biphenyl) -9H-carbazol-9-yl)phenyl]benzofuro[3,2-d]pyrimidine (abbreviation Name: 4PCCzPBfpm), 9-[3-(4,6-diphenyl-1,3,5-triazolidinedione] 9'-phenyl-2,3'-bi-9H-carbazole (abbreviation π-electron rich heteroaromatic rings and π-electron deficient heteroaromatic rings such as mPCCzPTzn-02 A heterocyclic compound having the following structure may also be used.

[0218] In addition, a substance in which a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring are directly bonded is The donor property of the π-electron-rich heteroaromatic ring and the acceptor property of the π-electron-deficient heteroaromatic ring are both strong. This is particularly preferable because the energy difference between the singlet excited state and the triplet excited state is small.

[0219] [ka]

[0220] In addition to the above, the second material, which is a material having a function of converting triplet excitation energy into luminescence, As the organic compound 122, a nanostructure of a transition metal compound having a perovskite structure is In particular, metal halide perovskites are preferred. The structure is preferably a nanoparticle or a nanorod.

[0221] In addition to the above, a compound that converts singlet excitation energy into light can be used in the light-emitting layer 113. Examples of luminescent substances include the following fluorescent substances (fluorescent substances). , pyrene derivatives, anthracene derivatives, triphenylene derivatives, fluorene derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, dibenzoquinoxa Phosphorus derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives, phenanthrene Pyrene derivatives in particular have a high luminescence quantum yield, Specific examples of pyrene derivatives include N,N'-bis(3-methylphenyl)- N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene -1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N,N'-diphenyl- N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene -1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bis(dibenzofuran) -2-yl)-N,N'-diphenylpyrene-1,6-diamine (abbreviation: 1,6FrAP rn), N,N'-bis(dibenzothiophen-2-yl)-N,N'-diphenylpyrene N,N'-(pyrene-1,6-diamine) yl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-6-amine] (abbreviation: 1,6BnfAPrn), N,N'-(pyren-1,6-diyl)bis[(N- Phenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6Bn fAPrn-02), N,N'-(pyren-1,6-diyl)bis[(6,N-diphenyl 1,6BnfAP rn-03) and others.

[0222] In addition, 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2, 2'-Bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl- 9-anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2B Py), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N' -Diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-calcium (bazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (Abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-di N,9-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA) Phenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazo PCAPA, 4-(10-phenyl-9-anthryl)-4 '-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PC BAPA), 4-[4-(10-phenyl-9-anthryl)phenyl]-4'-(9- Phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPBA ), Perylene, 2,5,8,11-tetra-tert-butylperylene (abbreviation: TBP) , N,N'-(2-tert-butylanthracene-9,10-diyldi-4,1-phenyl) N,N',N'-triphenyl-1,4-phenylenediamine)bis[N,N',N'-triphenyl-1,4-phenylenediamine](abbreviation :DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-an tolyl)phenyl]-9H-carbazol-3-amine (abbreviation: 2PCAPPA), N- [4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl phenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA) can be used. .

[0223] Next, as the third organic compound 123 which is the host material of the light-emitting layer 113, for example, Helical derivatives, tetracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives and condensed polycyclic aromatic compounds such as dibenzo[g,p]chrysene derivatives.

[0224] Specific examples of the above include 9-phenyl-3-[4-(10-phenyl-9-anthryl) phenyl]-9H-carbazole (abbreviation: PCzPA), 3,6-diphenyl-9-[4 -(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPC zPA), 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole PCPN, 9,10-diphenylanthracene (DPAnth), N ,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H- Carbazol-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthracene) (aryl)triphenylamine (abbreviation: DPhPA), YGAPA, PCAPA, N,9-di Phenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl} -9H-carbazol-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl (2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), 6,12-dimethoxy-5,11-diphenylchrysene, N,N,N' ,N',N'',N'',N''',N'''-Octaphenyldibenzo[g,p]chloride sen-2,7,10,15-tetraamine (abbreviation: DBC1), 9-[4-(10-phenyl) (9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), 7- [4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbamate BAZOLE (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthracene (aryl)phenyl)-benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA ), 9-phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)-biphenyl phenyl-4'-yl}-anthracene (abbreviation: FLPPA), 9,10-bis(3,5- Diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl) Anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl) Anthracene (abbreviation: t-BuDNA), 9,9'-bianthryl (abbreviation: BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviation: DPNS), 9 ,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 1 ,3,5-tri(1-pyrenyl)benzene (abbreviation: TPB3), 5,12-diphenyl terephthalate tetracene, 5,12-bis(biphenyl-2-yl)tetracene, and the like.

[0225] In addition, the third organic compound 123 serving as the host material of the light-emitting layer 113 may be, for example, Aromatic amines, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives , zinc or aluminum metal complexes, oxadiazole derivatives, triazole derivatives , benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, pyrimidine Imididine derivatives, pyrazine derivatives, triazine derivatives, pyridine derivatives, bipyridine derivatives , phenanthroline derivatives, etc. can be used.

[0226] Specific examples of these include 2-(4-biphenylyl)-5-(4-tert-butyl) phenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-( p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazole-2 -yl)phenyl]-9H-carbazole (abbreviation: CO11), 3-(4-biphenylyl) )-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (Abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl )-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), etc. The triazole derivative, 2,2',2''-(1,3,5-benzenetriyl)tris( 1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzo Thiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), 4,4'-bis(5-methylbenzoxazol-2-yl) Stilbene (abbreviation: BzOs), bathophenanthroline (abbreviation: Bphen), bathocu Proine (abbreviation: BCP), 2,9-bis(naphthalen-2-yl)-4,7-diphenyl 1,10-phenanthroline (abbreviation: NBphen), 2-[3-(dibenzothiophene) (4-phenyl)dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDB q-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]di Benzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-( 9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxalate 2mCzBPDBq, 2-[4-(3,6-diphenyl-9H-carbazol-1-yl)methyl] 2CzPDBq-I II), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]ky Noxaline (abbreviation: 7mDBTPDBq-II) and 6-[3-(dibenzothiophene -4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq- II) and other quinoxaline derivatives, or dibenzoquinoxaline derivatives.

[0227] Furthermore, 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviated :4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pi Pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 9,9'-(pyrimidine-4,6- Diyldi-3,1-phenylene)bis(9H-carbazole) (abbreviation: 4,6mCzP2 Pyrimidine derivatives such as 2-{4-[3-(N-phenyl-9H-carbazole- 3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3 ,5-triazine (abbreviation: PCCzPTzn), 9-[3-(4,6-diphenyl-1, 3,5-triazin-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-ca triazine derivatives such as rubazoline (abbreviation: mPCCzPTzn-02), 3,5-bis[ 3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy) , 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB) pyridine derivatives such as

[0228] In addition, poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexyl fluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF- Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2' -bipyridine-6,6'-diyl)] (abbreviation: PF-BPy) You can also be there.

[0229] <Electron transport layer> The electron transport layer 114 is formed by electron injection layer 115, which will be described later, and is injected from the second electrode 102. The electron transport layer 114 is a layer that transports the electrons to the light emitting layer 113. The electron transporting material used in the electron transport layer 114 is a layer containing 1×10 -6 cm 2 / V A substance having an electron mobility of s or higher is preferred. In addition, the electron transport layer (114, 114 a, 114b) can function as a single layer, but can be made into a laminated structure of two or more layers as needed. This can also improve the device characteristics.

[0230] The organic compound that can be used for the electron transport layer 114 is a furan compound having a furodiazine skeleton. Organic compounds with a structure in which an aromatic ring is condensed to a ring, metal complexes with a quinoline skeleton, benzo Metal complexes having a quinoline skeleton, metal complexes having an oxazole skeleton, and metal complexes having a thiazole skeleton In addition to metal complexes with oxadiazole derivatives, triazole derivatives, imidazole derivatives, Conductors, oxazole derivatives, thiazole derivatives, phenanthroline derivatives, quinoline coordination Quinoline derivatives, benzoquinoline derivatives, quinoxaline derivatives, dibenzoquinoline derivatives Xaline derivatives, pyridine derivatives, bipyridine derivatives, pyrimidine derivatives, and other nitrogen-containing compounds Highly electron-transporting materials such as π-electron-deficient heteroaromatic compounds (including heteroaromatic compounds) transportable materials) can be used.

[0231] Specific examples of electron transporting materials include 2-[3'-(dibenzothiophene-4-yl) )biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDB q-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]di Benzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 5-[3-(4 ,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-7,7-dimethyl- 5H,7H-Indeno[2,1-b]carbazole (abbreviation: mINc(II)PTzn) , 4-[3-(dibenzothiophen-4-yl)phenyl]-8-(naphthalene-2-yl)phenyl 8βN-4mDBtPBfp m), 3,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzofuro[2 ,3-b]pyrazine (abbreviation: 3,8mDBtP2Bfpr), 4,8-bis[3-(dibenzyl)pyrazine (benzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine ( Abbreviation: 4,8mDBtP2Bfpm), 9-[(3'-dibenzothiophen-4-yl) biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviation Name: 9mDBtBPNfpr), 8-[3'-(dibenzothiophen-4-yl)(1, 1'-biphenyl-3-yl)]naphtho[1',2':4,5]furo[3,2-d]pyri 8-[(2,2'-binaphthalene)-6-yl]-2,2'-binaphthalene (abbreviation: 8mDBtBPNfpm) yl]-4-[3-(dibenzothiophen-4-yl)phenyl-[1]benzofuro[3, 2-d]pyrimidine (abbreviation: 8(βN2)-4mDBtPBfpm), tris(8-quino linolato)aluminum(III) (abbreviation: Alq3), tris(4-methyl-8-quino Linolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]ky beryllium (abbreviated as BeBq2), bis(2-methyl-8-quinolinolato) ( 4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinol) linolato)zinc(II) (abbreviation: Znq) and other quinoline or benzoquinoline skeletons A metal complex having bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation Name: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation Examples include metal complexes having an oxazole skeleton or a thiazole skeleton, such as ZnBTZ. can be done.

[0232] In addition to metal complexes, oxadiazole derivatives such as PBD, OXD-7, and CO11, Triazole derivatives such as AZ and p-EtTAZ, and isopropyl alcohols such as TPBI and mDBTBIm-II Midazole derivatives (including benzimidazole derivatives), oxazole derivatives such as BzOs Conductors, phenanthroline derivatives such as Bphen, BCP, and NBphen, and 2mDBTP DBq-II, 2mDBTBPDBq-II, 2mCzBPDBq, 2CzPDBq-I II, 7mDBTPDBq-II, and 6mDBTPDBq-II. Conductors, dibenzoquinoxaline derivatives, pyridine derivatives such as 35DCzPPy and TmPyPB Body, 4,6mPnP2Pm, 4,6mDBTP2Pm-II, 4,6mCzP2Pm, etc. Pyrimidine derivatives or triazines such as PCCzPTzn, mPCCzPTzn-02 Derivatives can be used.

[0233] Furthermore, polymer compounds such as PPy, PF-Py, and PF-BPy can also be used.

[0234] <Electron injection layer> The electron injection layer 115 is a layer for increasing the efficiency of injection of electrons from the second electrode (cathode) 102. and the work function value of the material used for the second electrode (cathode) 102 and the electron injection layer 115 When compared with the LUMO level of the material being used, the difference is small (0.5 eV or less). Therefore, it is preferable to use lithium, cesium, fluoride, etc. for the electron injection layer 115. Lithium (LiF), Cesium Fluoride (CsF), Calcium Fluoride (CaF2), 8- (Quinolinolato)lithium (abbreviation: Liq), 2-(2-pyridyl)phenolatolithium (abbreviation: LiPP), 2-(2-pyridyl)-3-pyridinolatolithium (abbreviation: LiP Py), 4-phenyl-2-(2-pyridyl)phenolatolithium (abbreviation: LiPPP) , lithium oxide (LiO x ), alkali metals such as cesium carbonate, alkaline earth metals The group or compounds thereof can be used. Also, erbium fluoride (ErF3) The following rare earth metal compounds can be used:

[0235] In addition, as shown in FIG. 6(B), the two EL layers (103a, 103b) By providing a charge generating layer 104 between the electrodes, a structure in which multiple EL layers are stacked between a pair of electrodes is obtained. In this embodiment, the structure shown in FIG. ) described in the above, the hole injection layer (111), the hole transport layer (112), the light emitting layer (113), the electron The transport layer (114) and the electron injection layer (115) are formed by the hole injection layer described in FIG. 6(B). Entry layers (111a, 111b), hole transport layers (112a, 112b), light emitting layers (113a, 113b), electron transport layer (114a, 114b), electron injection layer (115a, 115b) The functions and materials used are common to both.

[0236] <Charge generation layer> The charge generating layer 104 in the light emitting device of FIG. 6(B) is formed on the first electrode (anode) 10. When a voltage is applied between the EL layer 103a and the second electrode (cathode) 102, electrons are injected into the EL layer 103a. The charge generation layer 104 has a function of injecting holes into the EL layer 103b. Even if an electron acceptor is added to a hole transporting material, The material may have a structure in which an electron donor (donor) is added to the material. The charge generation layer 104 may be formed using the above-mentioned materials. This makes it possible to suppress an increase in driving voltage when an EL layer is stacked.

[0237] In the charge generation layer 104, when an electron acceptor is added to a hole transport material, As the hole transporting material, the materials shown in this embodiment mode can be used. The acceptor is 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinoline. Examples include dimethane (abbreviation: F4-TCNQ), chloranil, etc. Examples of the oxides of metals belonging to Groups 4 to 8 in the table include: Vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide Examples include tin oxide, manganese oxide, and rhenium oxide.

[0238] In addition, the charge generating layer 104 is configured such that an electron donor is added to an electron transporting material. In this case, the materials shown in this embodiment mode can be used as the electron transporting material. As the electron donor, an alkali metal, an alkaline earth metal, a rare earth metal, or an element Metals belonging to Groups 2 and 13 of the periodic table and their oxides and carbonates can be used. Specifically, lithium (Li), cesium (Cs), magnesium (Mg), Calcium (Ca), ytterbium (Yb), indium (In), lithium oxide, carbonate It is preferable to use cesium, etc. Also, organic compounds such as tetrathianaphthacene may be used as the electron donor.

[0239] In addition, FIG. 6(B) shows a configuration in which two EL layers (103a, 103b) are stacked. However, by providing a charge generating layer between different EL layers, a laminated structure of three or more EL layers can be obtained. That's fine.

[0240] <Substrate> The light-emitting device shown in this embodiment mode can be formed over various substrates. The type of the substrate is not limited to a specific one. An example of the substrate is a semiconductor substrate (e.g., For example, single crystal substrate or silicon substrate), SOI substrate, glass substrate, quartz substrate, plastic Substrates, metal substrates, stainless steel substrates, substrates with stainless steel foil, Tungsten substrate, substrate with tungsten foil, flexible substrate, lamination film Examples of the substrate include paper, paper containing fibrous materials, and base films.

[0241] Examples of the glass substrate include barium borosilicate glass and aluminoborosilicate glass. Glass or soda lime glass, etc. Flexible substrates, lamination films, etc. Examples of base films include polyethylene terephthalate (PET), polyethylene terephthalate (PE ... Plastics such as polyethylene naphthalate (PEN) and polyethersulfone (PES) Synthetic resins such as acrylic resin, polypropylene, polyester, polyvinyl fluoride, Or polyvinyl chloride, polyamide, polyimide, aramid resin, epoxy resin, inorganic vapor deposition Examples of the material include film and paper.

[0242] Note that the light-emitting device shown in this embodiment mode can be manufactured by a vacuum process such as evaporation, a spin A solution process such as a coating method or an inkjet method can be used. If so, sputtering, ion plating, ion beam deposition, molecular beam deposition Physical vapor deposition (PVD) methods such as vacuum deposition, or chemical vapor deposition (CVD) methods are used. In particular, the functional layer (hole injection layer (111, 1 11a, 111b), hole transport layer (112, 112a, 112b), light emitting layer (113, 1 13a, 113b), electron transport layer (114, 114a, 114b), electron injection layer (115 , 115a, 115b)), and the charge generating layer (104, 104a, 104b) are deposition methods (vacuum deposition, etc.), coating methods (dip coating, die coating, bar coating) , spin coating method, spray coating method, etc.), printing method (inkjet method, screen (hole Plate printing), offset (lithographic printing), flexography (relief printing), gravure, The insulating layer can be formed by a method such as a contact method or a nanoimprint method.

[0243] The EL layers (103, 103a, 103b) of the light-emitting device shown in this embodiment are The functional layers (hole injection layers (111, 111a, 111b), hole transport layers (112, 113)) 2a, 112b), light emitting layer (113, 113a, 113b), electron transport layer (114, 11 4a, 114b), electron injection layer (115, 115a, 115b)), or charge generation layer ( 104, 104a, 104b) are not limited to the above-mentioned materials, and may be other materials. However, they can be used in combination as long as they fulfill the functions of each layer. Examples include high molecular weight compounds (oligomers, dendrimers, polymers, etc.), medium molecular weight compounds (low molecular weight compounds), Compounds in the intermediate range between molecules and polymers: molecular weight 400 to 4000), inorganic compounds (quantum dots As the quantum dot material, colloidal quantum dots can be used. alloy-type quantum dot materials, core-shell-type quantum dot materials, core-type quantum dot materials etc. can be used.

[0244] The structure described in this embodiment mode can be used in appropriate combination with structures described in other embodiments. It shall be possible.

[0245] (Fourth embodiment) In this embodiment, a light-emitting device according to one embodiment of the present invention will be described. The light emitting device shown in FIG. 2 comprises a transistor (FET) 202 and a light emitting device on a first substrate 201. (203R, 203G, 203B, 203W) are electrically connected to each other. A light-emitting device of the type having a plurality of light-emitting devices (203R, 203G, 203B, 20 3W) have a common EL layer 204 and are arranged such that the light emitted by each light-emitting device is of a desired color. As shown, the light-emitting device has a microcavity structure in which the optical distance between the electrodes is adjusted. Furthermore, light emitted from the EL layer 204 is reflected by a color filter ( 206R, 206G, 206B) is a top-emission type light-emitting device be.

[0246] In the light-emitting device shown in FIG. 7(A), the first electrode 207 is formed to function as a reflective electrode. The second electrode 208 is formed to have transparency to light (visible light or near-infrared light) and The electrode is formed to have both a transparent and reflective function and to function as a semi-transparent and semi-reflective electrode. In other embodiments, the electrode material for forming the first electrode 207 and the second electrode 208 may be can be used appropriately by referring to the description of

[0247] In addition, in FIG. 7(A), for example, the light emitting device 203R is a red light emitting device, The light emitting device 203G is a green light emitting device, the light emitting device 203B is a blue light emitting device, and the light emitting device When the light emitting device 203W is a white light emitting device, as shown in FIG. 03R is set so that the optical distance between the first electrode 207 and the second electrode 208 is 200R. The light emitting device 203G is adjusted so that the optical distance between the first electrode 207 and the second electrode 208 is The distance between the first electrode 207 and the second electrode 208 is adjusted to 200G. The optical distance between the pole 208 and the optical axis 200B is adjusted. Then, in the light-emitting device 203R, a conductive layer 210R is laminated on the first electrode 207, and the light-emitting device By laminating a conductive layer 210G in the device 203G, optical adjustment can be performed. Cut.

[0248] Color filters (206R, 206G, 206B) are formed on the second substrate 205. Color filters allow specific wavelength ranges of visible light to pass through and block specific wavelength ranges. Therefore, as shown in FIG. 7(A), the filter overlaps with the light-emitting device 203R. By providing a color filter 206R that passes only the red wavelength region at a position corresponding to the Red light can be emitted from the optical device 203R. By providing a color filter 206G that passes only the green wavelength region at a position corresponding to the wavelength of the light, Green light can be obtained from the optical device 203G. By providing a color filter 206B that transmits only the blue wavelength region at a position Blue light can be obtained from the optical device 203B. However, the light-emitting device 203W has the following characteristics: White light can be obtained without using a color filter. A black layer (black matrix) 209 may be provided on the edge of the filter. In addition, the color filters (206R, 206G, 206B) or the black layer 209 are made of a transparent material. The photosensitive layer may be covered with an overcoat layer using a photosensitive material.

[0249] In FIG. 7(A), a structure (top emission type) in which light is extracted to the second substrate 205 side is used. The light emitting device is shown, but as shown in FIG. 7(C), the first substrate on which the FET 202 is formed is The light emitting device may have a structure in which light is extracted from the 201 side (bottom emission type). In the case of a bottom emission type light emitting device, the first electrode 207 is a semi-transmissive and semi-reflective electrode. The first electrode 206 is formed to function as a reflecting electrode, and the second electrode 208 is formed to function as a reflecting electrode. The first substrate 201 is at least a light-transmitting substrate. (206R', 206G', 206B') are light-emitting devices (2 It is sufficient to provide them closer to the first substrate 201 than the other electrodes 203R, 203G, and 203B.

[0250] In addition, in FIG. 7(A), the light-emitting devices are a red light-emitting device, a green light-emitting device, and a blue light-emitting device. Although the cases of a color light-emitting device and a white light-emitting device have been described, The device is not limited to this configuration and may be a yellow light emitting device or an orange light emitting device. In order to manufacture these light-emitting devices, an EL layer may be used. (light-emitting layer, hole injection layer, hole transport layer, electron transport layer, electron injection layer, charge generation layer, etc.) The materials to be used may be selected appropriately by referring to the descriptions of other embodiments. In addition, it is necessary to select a color filter appropriately according to the color of light emitted by the light-emitting device.

[0251] By adopting the above-described configuration, a light emitting device having light emitting devices that emit light of a plurality of colors can be obtained. You can get a position.

[0252] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. It shall be possible to do so.

[0253] (Embodiment 5) In this embodiment, a light-emitting device which is one embodiment of the present invention will be described.

[0254] By applying the device configuration of the light-emitting device according to one embodiment of the present invention, A light-emitting device of a glass transition type or a passive matrix type can be manufactured. An active matrix light emitting device is a device that combines a light emitting device and a transistor (FET). Therefore, it is possible to use a passive matrix light emitting device, an active matrix light emitting device, Any of the above-described light-emitting devices is included in one embodiment of the present invention. The light emitting device described in the other embodiments can be applied to the light emitting apparatus.

[0255] In this embodiment mode, an active matrix light-emitting device will be described with reference to FIG.

[0256] 8A is a top view showing the light emitting device, and FIG. 8B is a top view showing the light emitting device along the dashed line AA in FIG. 8A. The active matrix light emitting device is A pixel portion 302, a driver circuit portion (source line driver circuit) 303, and a driver circuit portion (gate The pixel section 302 and the driver circuit section (304a, 304b) are connected to the pixel section 302. The first substrate 301 and the second substrate 302 are connected by a sealing material 305. It is sealed between the plate 306 .

[0257] Furthermore, lead wiring 307 is provided on the first substrate 301. is electrically connected to the FPC 308, which is an external input terminal. An external signal (for example, a video signal, a clock signal) is input to the driving circuit unit (303, 304a, 304b). signal, start signal, reset signal, etc.) or electric potential. A printed wiring board (PWB) may be attached to 8. The state in which the PWB is attached is included in the light emitting device.

[0258] Next, a cross-sectional structure is shown in FIG.

[0259] The pixel section 302 includes a FET (switching FET) 311, a FET (current control FET) 312, and a plurality of pixels having a first electrode 313 electrically connected to the FET 312. The number of FETs that each pixel has is not particularly limited, and It can be provided as needed.

[0260] The FETs 309, 310, 311, and 312 are not particularly limited, and may be, for example, staggered. A top gate type or an inverted staggered type transistor can be used. Alternatively, a transistor structure such as a bottom gate type may be used.

[0261] The semiconductor crystals that can be used for these FETs 309, 310, 311, and 312 are The crystallinity is not particularly limited, and may be an amorphous semiconductor, a crystalline semiconductor (microcrystalline semiconductor, Any of polycrystalline semiconductors, single-crystalline semiconductors, and semiconductors having crystalline regions in part may be used. Note that the use of a crystalline semiconductor can suppress the deterioration of transistor characteristics. This is preferable because it is possible to

[0262] In addition, these semiconductors include, for example, elements of Group 14, compound semiconductors, and oxide semiconductors. , organic semiconductors, etc. can be used. Typically, semiconductors containing silicon, gallium, A semiconductor containing arsenic, an oxide semiconductor containing indium, or the like can be used.

[0263] The driving circuit section 303 includes an FET 309 and an FET 310. is formed by a circuit containing transistors of one polarity (either N-type or P-type only). Alternatively, it may be formed by a CMOS circuit including N-type and P-type transistors. Alternatively, a configuration having an external driving circuit may be used.

[0264] The end of the first electrode 313 is covered with an insulator 314. Organic compounds such as negative photosensitive resins, positive photosensitive resins (acrylic resins), oxide Inorganic compounds such as silicon, silicon oxynitride, and silicon nitride can be used. It is preferable that the upper or lower end of 314 has a curved surface with a curvature. This allows the coating properties of the film formed on the upper layer of the insulator 314 to be improved.

[0265] An EL layer 315 and a second electrode 316 are stacked on the first electrode 313. 315 is a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, etc. Has.

[0266] The configuration of the light-emitting device 317 shown in this embodiment is the same as that described in the other embodiments. Although not shown here, the second electrode 316 is electrically connected to the FPC 308, which is an external input terminal.

[0267] In addition, although only one light-emitting device 317 is shown in the cross-sectional view of FIG. 8(B), In the unit 302, a plurality of light emitting devices are arranged in a matrix. The element 302 has three light emitting devices that can emit light of three kinds (R, G, B). In addition, three types of light emitting devices (R, In addition to light-emitting devices that can emit light in the colors white (W), yellow (Y), A light-emitting device that emits light of blue, magenta (M), cyan (C), or the like may be formed. For example, a light-emitting device that emits three types of light (R, G, B) can emit several of the above types of light. By adding a light-emitting device that can be used in a variety of applications, it is possible to improve color purity and reduce power consumption. In addition, full color display is possible when combined with a color filter. The light emitting device may be a light emitting device. Blue (B), cyan (C), magenta (M), yellow (Y), etc. can be used.

[0268] FETs (309, 310, 311, 312) and light-emitting devices on a first substrate 301 317 is a sealant 305 that bonds the second substrate 306 and the first substrate 301 together. As a result, the space surrounded by the first substrate 301, the second substrate 306, and the sealing material 305 is The space 318 is filled with an inert gas (nitrogen or argon). The insulating layer 304 may be filled with a material such as argon, or an organic material (including a sealant 305).

[0269] The sealing material 305 can be made of epoxy resin or glass frit. It is preferable to use a material for the sealant 305 that is as impermeable to moisture and oxygen as possible. The second substrate 306 may be made of the same material as the first substrate 301. Therefore, various substrates described in other embodiments can be used as appropriate. The substrate may be a glass substrate, a quartz substrate, or an FRP (Fiber-Reinforced Plastic) substrate. Inforced Plastics), PVF (Polyvinyl Fluoride), Polyester A plastic substrate made of aluminium or acrylic resin can be used as the sealing material. When glass frit is used, the first substrate 301 and the second substrate 302 are bonded to each other from the viewpoint of adhesiveness. 306 is preferably a glass substrate.

[0270] In this manner, an active matrix light emitting device can be obtained.

[0271] In addition, when an active matrix light emitting device is formed on a flexible substrate, The FET and the light emitting device may be formed directly, or the FET and the light emitting device may be formed on a separate substrate having a release layer. After forming the optical device, the FET and the light-emitting device are separated by applying heat, force, laser irradiation, etc. The substrate may be peeled off at a peeling layer and then transferred onto a flexible substrate. For example, a laminate of inorganic films such as a tungsten film and a silicon oxide film, or a polyimide film, etc. The flexible substrate may be a film of an organic resin, for example, a film on which a transistor is formed. In addition to the substrates that can be used, paper substrates, cellophane substrates, aramid film substrates, polyimide substrates, Film substrate, cloth substrate (natural fibers (silk, cotton, linen), synthetic fibers (nylon, polyurethane) , polyester) or regenerated fiber (acetate, cupra, rayon, regenerated polyester Examples of the substrate include a leather substrate, a rubber substrate, etc. This allows for excellent durability or heat resistance, and allows for lighter weight and thinner construction.

[0272] The light-emitting devices in the active matrix light-emitting device are driven by the light-emitting devices. A structure that emits light in pulses (for example, using frequencies such as kHz or MHz) and is used for display. The light-emitting device formed using the organic compound has excellent frequency characteristics. Therefore, the driving time of the light emitting device can be shortened, and power consumption can be reduced. In addition, heat generation is suppressed as the driving time is shortened, which reduces the deterioration of the light-emitting device. It is also possible.

[0273] Note that the structure shown in this embodiment mode may be used in appropriate combination with structures shown in other embodiment modes. It is possible.

[0274] (Embodiment 6) In this embodiment, a light-emitting device according to one embodiment of the present invention, Examples of various electronic devices and automobiles that have been completed using a light-emitting device with a chair are as follows. Note that the light-emitting device is mainly used for display in the electronic devices described in this embodiment mode. This can be applied to the part.

[0275] The electronic device shown in FIGS. 9A to 9E includes a housing 7000, a display portion 7001, a speaker, and a 7003, LED lamp 7004, operation key 7005 (power switch or operation switch ), connection terminal 7006, sensor 7007 (force, displacement, position, velocity, acceleration, angular velocity , rotation speed, distance, light, liquid, magnetism, temperature, chemicals, sound, time, hardness, electric field, current, voltage , including the ability to measure power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays. ), a microphone 7008, etc.

[0276] FIG. 9(A) shows a mobile computer, which includes the above-mentioned components, a switch 7009, a red It may have an outside line port 7010, etc.

[0277] FIG. 9(B) shows a portable image reproducing device (for example, a DVD reproducing device) equipped with a recording medium. In addition to the above, it may have a second display unit 7002, a recording medium reading unit 7011, etc. This can be done.

[0278] Figure 9(C) shows a digital camera with a TV receiving function, which, in addition to the above, also has an antenna. 7014, a shutter button 7015, an image receiving unit 7016, etc.

[0279] 9D shows a portable information terminal. The portable information terminal displays information on three or more screens of a display portion 7001. Here, information 7052, information 7053, and information 7054 are respectively For example, the user may have a mobile information terminal in his / her breast pocket. When the terminal is stored, information 7053 is displayed in a position that can be observed from above the mobile information terminal. Users can check the display without taking the mobile information terminal out of their pocket. and can decide, for example, whether to answer the call or not.

[0280] FIG. 9E shows a portable information terminal (including a smartphone), in which a display unit 7 is mounted in a housing 7000. 001, operation keys 7005, etc. The portable information terminal may have a speaker, 7003, a connection terminal 7006, a sensor 7007, etc. may be provided. It can display text, text, or image information on its multiple sides. 7 shows an example in which information 7051 shown in a dashed rectangle is displayed on the display unit 7 001. Examples of information 7051 include email, S NS, notification of incoming calls, etc., subject of email or SNS, sender name, date and time, etc. The time, remaining battery power, antenna reception strength, etc. Or, information 7051 is displayed. An icon 7050 or the like may be displayed at the position where the icon is displayed.

[0281] Figure 9(F) shows a large television set (also called a television or television receiver). The device may have a housing 7000, a display unit 7001, and the like. The housing 7000 is supported by a support 7018. The operation of the display unit 7111 can be performed by a separate remote control unit 7111. The display unit 7001 may be provided with a touch sensor, and the operation can be performed by touching the display unit 7001 with a finger or the like. The remote control device 7111 may output information The remote control 7111 may have a display unit that displays the operation keys or buttons. The channel and volume can be controlled by the touch panel, and the display unit 7001 The image displayed can be manipulated.

[0282] The electronic devices shown in FIGS. 9A to 9F can have various functions. For example, , the function to display various information (still images, videos, text images, etc.) on the display, Functions such as calendar, date and time display, various software (programs) It has the functions of controlling processing by wireless communication, and various computers using wireless communication functions. It has the function of connecting to a data network, and the function of transmitting or receiving various data using wireless communication. The function of reading out the program or data recorded on the recording medium and displaying it on the display unit. Furthermore, in an electronic device having multiple display units, One display mainly displays image information, and the other mainly displays text information. or the ability to display images that take parallax into account on multiple displays to create a three-dimensional image. Furthermore, in an electronic device having an image receiving unit, Functions for taking still images, shooting videos, and automatically or manually correcting captured images Function, function to save the captured image to a recording medium (external or built-in to the camera), 9(A) to 9(F) can be displayed on the display unit. The functions that the electronic device shown in the figure can have are not limited to these, and it may have various functions. can be done.

[0283] FIG. 9(G) shows a wristwatch-type portable information terminal, which is used as, for example, a wristwatch-type electronic device. This wristwatch-type portable information terminal is made up of a housing 7000, a display unit 7001, and an operation unit. Buttons 7022, 7023, connection terminal 7024, band 7025, microphone 702 6, a sensor 7029, a speaker 7030, etc. The display unit 7001 has a curved display surface. The display is curved, allowing the display to be displayed along the curved display surface. For example, hands-free calling is possible by communicating with a wireless headset. In addition, the connection terminal 7024 allows mutual data transmission with other information terminals. Alternatively, charging can be performed. Charging can also be performed by wireless power supply.

[0284] The display unit 7001 mounted on the housing 7000, which also serves as a bezel, has a non-rectangular display area. The display unit 7001 can display an icon representing the time, other icons, etc. The display unit 7001 is a touch panel equipped with a touch sensor (input device). It may also be an input / output device.

[0285] The wristwatch-type electronic device shown in FIG. 9(G) can have various functions. For example, functions to display various information (still images, videos, text images, etc.) on the display, Panel function, calendar, date or time display function, various software (program It has the functions of controlling processing by RAM, wireless communication functions, and various computers using wireless communication functions. Functions for connecting to computer networks, sending or receiving various data using wireless communication functions The function of reading out the program or data recorded on the recording medium and displaying it on the display unit. It may have the function of:

[0286] In addition, a speaker, a sensor (force, displacement, position, velocity, acceleration, angular velocity) Degrees, rotation speed, distance, light, liquid, magnetism, temperature, chemical substances, sound, time, hardness, electric field, current, electricity Includes functions to measure pressure, power, radiation, flow rate, humidity, gradient, vibration, odor or infrared. ), a microphone, etc.

[0287] Note that the light-emitting device which is one embodiment of the present invention can be used for each display portion of the electronic devices described in this embodiment. This makes it possible to realize electronic devices with long life.

[0288] In addition, as an electronic device to which a light-emitting device is applied, a folding type electronic device as shown in FIGS. A foldable mobile information terminal is an example. Figure 10(A) shows a mobile information terminal in an unfolded state. 9310. Also, in FIG. 10(B), the 10C shows the mobile information terminal 9310 in a state in which the state is changing from one to the other. 1 shows the portable information terminal 9310 in a folded state. When folded, it is highly portable, and when unfolded, it has a seamless, wide display area for easy viewing. Excellent overview.

[0289] The display unit 9311 is supported by three housings 9315 connected by hinges 9313. The display unit 9311 is a touch panel (input / output) equipped with a touch sensor (input device). The display unit 9311 may be connected to two housings via a hinge 9313. By bending the space between the terminals 9315, the portable information terminal 9310 can be folded from the unfolded state. The light-emitting device of one embodiment of the present invention can be reversibly transformed into a display state. The display portion 931 can be used for the display unit 9311. In addition, a long-life electronic device can be realized. The display area 9312 in FIG. 1 is located on the side of the portable information terminal 9310 in the folded state. The display area 9312 displays information icons, frequently used apps, and can display program shortcuts, check information, or run applications. It is possible to smoothly start up the following:

[0290] Also, an automobile to which a light emitting device is applied is shown in Fig. 11(A)(B). The device can be provided integrally with a vehicle. External lights 5101 (including the rear of the car), tire wheels 5102, doors 510 3 can be applied to a part or the whole of the car shown in FIG. A side display unit 5104, a steering wheel 5105, a shift lever 5106, a seat 5107, It can be applied to inner rearview mirror 5108, windshield 5109, etc. It may also be applied to other glass window parts.

[0291] As described above, an electronic device or an automobile to which the light-emitting device of one embodiment of the present invention is applied can be manufactured. In this case, it is possible to realize a long-life electronic device. The electronic devices and automobiles that can be used are not limited to those shown in the present embodiment, but can be used in a variety of fields. It can be applied to

[0292] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiment modes. It is possible.

[0293] (Embodiment 7) In this embodiment, a light-emitting device according to one embodiment of the present invention or a light-emitting device which is a part thereof will be described. The structure of a lighting device manufactured by applying the above will be described with reference to FIGS.

[0294] 12 and 13 show examples of cross-sectional views of a lighting device. Note that FIG. 12 shows a case where light is taken in from the substrate side. The bottom emission type lighting device is a bottom emission type lighting device that extracts light from the encapsulation substrate side. It is a top emission type lighting device.

[0295] The lighting device 4000 shown in FIG. 12 has a light-emitting device 4002 on a substrate 4001. The light-emitting device 4002 further includes a substrate 4003 having an uneven surface on the outer side of the substrate 4001. , a first electrode 4004 , an EL layer 4005 , and a second electrode 4006 .

[0296] The first electrode 4004 is electrically connected to the electrode 4007, and the second electrode 4006 is electrically connected to the electrode 4008. 008. An auxiliary wiring electrically connected to the first electrode 4004. An insulating layer 4010 may be formed on the auxiliary wiring 4009. There are.

[0297] The substrate 4001 and the sealing substrate 4011 are bonded together with a sealant 4012. A desiccant 4013 is provided between the sealing substrate 4011 and the light-emitting device 4002. It is preferable that the substrate 4003 has the unevenness shown in FIG. The extraction efficiency of the light generated in 4002 can be improved.

[0298] The lighting device 4200 of FIG. 13 has a light-emitting device 4202 on a substrate 4201. The device 4202 has a first electrode 4204, an EL layer 4205, and a second electrode 4206. do.

[0299] The first electrode 4204 is electrically connected to the electrode 4207, and the second electrode 4206 is electrically connected to the electrode 4208. 208. The auxiliary wiring 4206 is electrically connected to the second electrode 4206. An insulating layer 4210 may be provided under the auxiliary wiring 4209. stomach.

[0300] The substrate 4201 and the sealing substrate 4211 having projections and recesses are bonded with a sealant 4212. In addition, a barrier film 4213 and a planarization film 4214 are formed between the sealing substrate 4211 and the light-emitting device 4202. 214 may be provided. Note that since the sealing substrate 4211 has the unevenness as shown in FIG. The extraction efficiency of light generated in the light emitting device 4202 can be improved.

[0301] An example of the application of these lighting devices is a ceiling light for indoor lighting. There are two types of ceiling lights: direct ceiling mounted and recessed ceiling lights. Such a lighting device is constructed by combining a light-emitting device with a housing or a cover. do.

[0302] Other applications include footlights that can illuminate the floor and increase safety underfoot. Footlights are useful in bedrooms, staircases, or corridors, for example. In this case, the size or shape can be changed appropriately depending on the size or structure of the room. In addition, a stationary lighting device can be formed by combining a light emitting device with a support base. It is also possible to

[0303] It can also be used as a sheet-type lighting device (sheet-type lighting). The lighting is attached to the wall, so it doesn't take up much space and can be used for a wide range of purposes. It is also easy to make it larger. It can also be used on curved walls or enclosures. Cut.

[0304] In addition to the above, a light-emitting device according to one embodiment of the present invention may be attached to a part of furniture installed in a room. By applying a light-emitting device, which is a part of the design, we aim to create a lighting device that also functions as furniture. can be done.

[0305] As described above, various lighting devices using the light-emitting device can be obtained. is included in one aspect of the present invention.

[0306] The structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. It is possible. [Example]

[0307] <Synthesis Example 1> In this example, a compound represented by structural formula (100) in Embodiment 1, which is one embodiment of the present invention, , N,N'-bis[3,5-bis(2-adamantyl)phenyl]-N,N'-bis(3 ,5-di-tert-butylphenyl)-2-phenylanthracene-9,10-diamine This section explains how to synthesize the compound (abbreviation: 2Ph-mmAdtBuDPhA2Anth). The structure of 2Ph-mmAdtBuDPhA2Anth is shown below.

[0308] [ka]

[0309] <Step 1: Synthesis of 3-(2-adamantyl)-5-bromoanisole> 5.3 g (20 mmol) of 3,5-dibromoanisole was placed in a 500 mL three-neck flask. The atmosphere in the flask was replaced with nitrogen. 200 mL of tetrahydrofuran was added to the flask, and the temperature was adjusted to -80 The solution was stirred at 100°C. 14 mL (22 mmol) of n-butyllithium (1.6 mo 1 / L n-hexane solution) was added dropwise and stirred under a nitrogen stream for 2 hours. Add 3.7 g (25 mmol) of 2-adamantanone and gradually return the temperature to room temperature. The mixture was stirred for 15 hours.

[0310] After stirring, water was added to the mixture, and the aqueous layer was extracted with ethyl acetate. The mixture was combined, washed with water and saturated brine, and then dried over magnesium sulfate. The precipitate was filtered off, and the filtrate was concentrated to give a pale yellow oil.

[0311] The obtained oil was placed in a 500 mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen. 0.00 mL of dichloromethane was added and stirred at 0° C. To this solution was added 9.6 mL (60 mmol) of dichloromethane. 1) Add 15 mL (120 mmol) of triethylsilane and add 15 mL (120 mmol) of boron trifluoride ether. The mixture was stirred for 15 hours while the temperature was returned to room temperature.

[0312] After stirring, the mixture was added dropwise to a saturated aqueous solution of sodium bicarbonate, and the aqueous layer was extracted with dichloromethane. The resulting extract and the organic layer were combined, washed with water and saturated brine, and then extracted with magnesium sulfate. The mixture was separated by gravity filtration, and the filtrate was concentrated to give a pale yellow oil. .

[0313] The resulting oil was purified by silica gel column chromatography (eluent: hexane / toluene) The resulting solid was purified by HPLC (elution ratio: 4:1) to obtain the target white solid. The desired white solid was obtained in an amount of 3.1 g in a yield of 48%. The synthesis scheme of step 1 is shown below in (a-1).

[0314] [ka]

[0315] In addition, the white solid obtained in step 1 above 1The results of the H NMR measurements are shown below. From this result, it was found that 3-(2-adamantyl)-5-bromoanisole was obtained. It was.

[0316] 1 H NMR(CDCl3,300MHz):σ=7.09-7.08(m,1H),6 .88-6.82(m,2H),3.79(s,3H),2.93(m,1H),2.3 9(m,2H),2.01-1.77(m,11H),1.58(m,1H).

[0317] <Step 2: Synthesis of 3,5-bis(2-adamantyl)anisole> 3.1 g (9.6 mmol) of 3-(2-adamantyl)-5-bromoanisole was added to 50 The flask was then filled with nitrogen. The solution was added with 2.0 mL (11 mmol) of n-butyl ether and stirred at -80°C. Add 1.6 mol / L of ethyllithium (n-hexane solution) dropwise and stir under a nitrogen stream for 2 hours. Then, 1.9 g (13 mmol) of 2-adamantanone was added to the mixture, and the temperature was The mixture was stirred for 15 hours while gradually returning to room temperature.

[0318] After stirring, water was added to the mixture, and the aqueous layer was extracted with ethyl acetate. The mixture was combined, washed with water and saturated brine, and then dried over magnesium sulfate. The precipitate was filtered off, and the filtrate was concentrated to give a pale yellow oil.

[0319] The obtained oil was placed in a 500 mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen. 00 mL of dichloromethane was added and stirred at 0° C. To this solution, 4.6 mL (29 mmol) l) triethylsilane was added, and 7.2 mL (57 mmol) of boron trifluoride ether was added. The mixture was stirred for 15 hours while the temperature was returned to room temperature.

[0320] After stirring, the mixture was added dropwise to a saturated aqueous solution of sodium bicarbonate, and the aqueous layer was extracted with dichloromethane. The resulting extract and the organic layer were combined, washed with water and saturated brine, and then extracted with magnesium sulfate. The mixture was separated by gravity filtration, and the filtrate was concentrated to give a pale yellow solid.

[0321] Toluene was added to the obtained solid, and the residue was collected by suction filtration, and the target white solid was obtained. The obtained solid was purified by HPLC (developing solvent: chloroform), and the desired product was obtained. The synthesis scheme of step 2 is shown below (a-2). Shown below.

[0322] [ka]

[0323] In addition, the white solid obtained in step 2 above 1 The results of the H NMR measurements are shown below. This result indicates that 3,5-bis(2-adamantyl)anisole was obtained. .

[0324] 1 H NMR(CDCl3,300MHz):σ=6.96(m,1H),6.74(m ,2H),3.81(s,3H),2.98(m,2H),2.44(m,4H),2. 02-1.77(m,22H),1.57(m,2H).

[0325] <Step 3: Synthesis of 3,5-bis(2-adamantyl)phenol> 1.6 g (4.4 mmol) of 3,5-bis(2-adamantyl)anisole was dissolved in 500 ml of The flask was then filled with nitrogen. 120 mL of dichloromethane was added. The solution was stirred at 0° C. 75 mL of boron tribromide (1.0 mol 1 / L dichloromethane solution, 75 mmol) was added dropwise, and after the addition, the solution was allowed to return to room temperature while The mixture was stirred for 5 hours.

[0326] After stirring, the mixture was added dropwise to a saturated aqueous solution of sodium bicarbonate at 0°C. The aqueous layer was extracted with dichloromethane. The resulting extract and the organic layer were combined, and the mixture was washed with water and saturated brine. After washing with water, the mixture was dried over magnesium sulfate. Upon condensation, 1.6 g of the target white solid was obtained. The synthesis scheme of Step 3 is shown below (a- 3) is shown.

[0327] [ka]

[0328] In addition, the white solid obtained in step 3 above 1 The results of the H NMR measurements are shown below. From these results, it was found that 3,5-bis(2-adamantyl)phenol was obtained. .

[0329] 1 H NMR(CDCl3,300MHz):σ=6.93(m,1H),6.66(m ,2H),4.51(s,1H),2.95(m,2H),2.42(m,4H),2. 02-1.77(m,20H),1.57-1.53(m,4H).

[0330] Step 4: 3,5-bis(2-adamantyl)phenyl trifluoromethanesulfone Acid Synthesis> 1.6 g (4.4 mmol) of 3,5-bis(2-adamantyl)phenol was dissolved in 100 ml of The flask was then filled with nitrogen. 40 mL of dichloromethane and Then, 2.0 mL (14 mmol) of triethylamine was added and stirred at 0°C. 5 mL of dichloromethanesulfonic acid containing 1 mL (6.6 mmol) of trifluoromethanesulfonic anhydride The fluoromethane solution was added dropwise, and the mixture was stirred for 15 hours while the temperature was returned to room temperature.

[0331] After stirring, 1N hydrochloric acid was added to the mixture, and the aqueous layer was extracted with dichloromethane. The aqueous solution and the organic layer were combined, washed with water and saturated brine, and then dried over magnesium sulfate. The mixture was separated by gravity filtration, and the filtrate was concentrated to give a brown oil.

[0332] This solid was purified by silica gel column chromatography (developing solvent: hexane). As a result, 2.0 g of the target colorless oil was obtained in a yield of 92%. is shown in (a-4) below.

[0333] [ka]

[0334] In addition, the white solid obtained in step 4 above 1 The results of the H NMR measurements are shown below. From these results, 3,5-bis(2-adamantyl)phenyl trifluoromethanesulfone It was found that the acid was obtained.

[0335] 1 H NMR(CDCl3,300MHz):σ=7.35(m,1H),7.05(m ,2H),3.01(m,2H),2.43(m,4H),2.04-1.91(m,1 0H), 1.78-1.74(m, 10H), 1.60-1.56(m, 4H).

[0336] Step 5: 3,5-bis(2-adamantyl)-3',5'-di-tert-butyl Synthesis of diphenylamine> 2.0 g (4.0 mmol) of 3,5-bis(2-adamantyl)phenyltrifluoro Methanesulfonic acid was placed in a 200 mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen. 10 mL of tetrahydrofuran and 1.0 g (4.9 mmol) of 3,5-di-tert -butylaniline and 1.9 g (5.8 mmol) of cesium carbonate and 0.13 g (0.2 1mmol) of (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene (±)-BINAP was added to the mixture, and the mixture was degassed under reduced pressure. g (0.13 mmol) of palladium(II) acetate was added, and the mixture was heated under a nitrogen atmosphere for 7 The mixture was stirred at 0°C for 21 hours.

[0337] After stirring, 500 mL of toluene was added to the resulting mixture, and then Florisil (Wako Pure Chemical Industries, Ltd.) was added. Co., Ltd., Catalog No.: 066-05265), Celite (Wako Pure Chemical Industries, Ltd., Catalog number: 537-02305), and suction-filtered through aluminum oxide to obtain the filtrate. The obtained filtrate was concentrated to give a reddish brown solid.

[0338] This solid was purified by silica gel column chromatography (developing solvent: hexane:toluene=4: The product was purified by the method described in step 1) to give 2.2 g of a white solid in 98% yield. The synthesis scheme of 5 is shown in (a-5) below.

[0339] [ka]

[0340] In addition, the white solid obtained in step 5 above 1 The results of the H NMR measurements are shown below. From these results, 3,5-bis(2-adamantyl)-3',5'-di-tert-butyl It was found that diphenylamine was obtained.

[0341] 1 H NMR(CD2Cl2,300MHz):σ=6.98-6.97(m,1H), 6.93-6.92(m,5H),5.77(bs,1H),2.97(m,2H),2 .42(m,4H),2.02-1.88(m,14H),1.78(m,6H),1. 59-1.55(m,4H),1.30(s,18H).

[0342] <Step 6: Synthesis of 2Ph-mmAdtBuDPhA2Anth> 0.82 g (2.0 mmol) of 9,10-dibromo-2-phenylanthracene and 2 0.2g (3.9mmol) of 3,5-bis(2-adamantyl)-3',5'-di-te rt-butyldiphenylamine and 0.75 g (7.8 mmol) of sodium tert-butyldiphenylamine t-butoxide and 30 mg (73 μmol) of 2-dicyclohexylphosphino-2' ,6'-Dimethoxy-1,1'-biphenyl (abbreviation: SPhos) was added to a 200mL three-neck flask. The mixture was placed in a flask and the atmosphere inside the flask was replaced with nitrogen. 20 mL of xylene was added to this mixture, and After degassing the mixture under reduced pressure, 20 mg (35 μmol) of bis(dibenzylidene amine) was added to the mixture. Palladium(0)acetone was added, and the mixture was stirred at 150°C for 6 hours under a nitrogen atmosphere. .

[0343] After stirring, 500 mL of toluene was added to the resulting mixture, and then Florisil (Wako Pure Chemical Industries, Ltd.) was added. Co., Ltd., Catalog No.: 066-05265), Celite (Wako Pure Chemical Industries, Ltd., The resulting solution was filtered through alumina under suction to obtain a filtrate. The filtrate was concentrated to give a brown solid.

[0344] This solid was purified by silica gel column chromatography (developing solvent: hexane:toluene=9: The yellow solid was purified by 1) to obtain the target product. The target yellow solid was obtained by recrystallization from ethanol. When purified by high-performance liquid chromatography (HPLC), the target yellow solid was obtained. The synthesis scheme for Step 6 is shown below in (a-6).

[0345] [ka]

[0346] The resulting yellow solid (0.29 g) was purified by train sublimation. The yellow solid was heated at 300°C for 15 hours under a pressure of 3.3 Pa. After the purification, the target yellow solid was obtained in a yield of 0.22 g and a recovery rate of 76%.

[0347] In addition, the yellow solid obtained in step 6 above 1 The results of the H NMR measurements are shown below. Also, 1 The H NMR chart is shown in Figure 14. From this result, it is clear that 2Ph-mmAdtBuD It was found that PhA2Anth (structural formula (100)) was obtained.

[0348] 1 H NMR(CD2Cl2,300MHz):σ=8.39-8.37(m,1H), 8.26-8.11(m,3H),7.62-7.54(m,1H),7.43-7.2 5(m,7H),7.04-6.92(m,12H),2.89-2.86(m,4H) ,2.21-2.16(m,8H),1.87-1.57(m,40H),1.46-1 .27(m,8H),1.15-1.13(m,36H).

[0349] Next, the absorption spectrum of 2Ph-mmAdtBuDPhA2Anth in toluene and The ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum were measured. The absorption spectrum was measured using ultraviolet-visible spectrophotometry. A spectrometer (V550 model, manufactured by JASCO Corporation) was used to measure the emission spectrum. A fluorometer (FP-8600DS, manufactured by JASCO Corporation) was used. Absorption and emission spectra of AdtBuDPhA2Anth in toluene solution The measurement results are shown in Figure 15. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity.

[0350] As shown in Figure 15, the toluene solution of 2Ph-mmAdtBuDPhA2Anth exhibits a peak at 492 nm An absorption peak is observed around 539 nm (excitation wavelength 460 nm). It was. [Example]

[0351] In this example, a light-emitting device was manufactured using a compound according to one embodiment of the present invention, and its operating characteristics were evaluated. The light-emitting devices shown in this example are Light-emitting Device 1-1 and Light-emitting Device 1 -2, light-emitting device 1-3, light-emitting device 1-4, and light-emitting device 1-5, These light-emitting devices have the element structure shown in FIG. 16 and are the same as the fifth example of the light-emitting layer configuration of the second embodiment. Specifically, the light-emitting device has the configuration shown in Table 1. The compound of one embodiment of the present invention, N,N'-bis[3,5-bis( 2-adamantyl)phenyl]-N,N'-bis(3,5-di-tert-butylphenyl) 2Ph-mmAdtBu The content of DPhA2Anth) is different, but the other components are the same. As a comparative example of a light-emitting device, a compound according to one embodiment of the present invention contained in a light-emitting layer of a light-emitting device was used. Comparison of luminescence using TTPA instead of the compound 2Ph-mmAdtBuDPhA2Anth Device 1-a is shown. The chemical formulas of the materials used in this example are shown below.

[0352] [Table 1]

[0353] [ka]

[0354] <Light-emitting device configuration> The light emitting device shown in this example is a first electrode formed on a substrate 900 as shown in FIG. On the electrode 901, a hole injection layer 911, a hole transport layer 912, and a light emitting layer 9 13, an electron transport layer 914 and an electron injection layer 915 are sequentially stacked, and a second The electrode 903 has a laminated structure.

[0355] A glass substrate was used as the substrate 900. The first electrode 901 contained silicon oxide. The first electrode was an indium tin oxide (ITSO) film with a thickness of 70 nm. The electrode area of ​​901 is 4mm 2 (2mm x 2mm).

[0356] The hole injection layer 911 is made of 4,4',4''-(benzene-1,3,5-triyl)tri( Dibenzothiophene) (abbreviation: DBT3P-II) and molybdenum oxide co-evaporation film (DB T3P-II: molybdenum oxide = 1:0.5 (mass ratio) was used, and the film thickness was set to 40 nm. .

[0357] The hole transport layer 912 is made of 4,4'-diphenyl-4''-(9-phenyl-9H-carbamoyl) PCBBi1BP was used to form a 20 nm.

[0358] The light-emitting layer 913 of each of the light-emitting devices 1-1 to 1-4 contains 9-[3-(4,6- Diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-2,3 '-Bi-9H-carbazole (abbreviation: mPCCzPTzn-02), 3,3'-bis(9 -phenyl-9H-carbazole) (abbreviation: PCCP), [2-(4-methyl-5-phenyl bis[2-(2-pyridinyl-κN)phenyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κC] [phenyl-κC]iridium (abbreviation: [Ir(ppy)2(mdppy)]), and 2P A film having h-mmAdtBuDPhA2Anth was used, and the film thickness was set to 40 nm. The light-emitting layer 913 of the light-emitting device 1-5 contains mPCCzPTzn-02, PCCP, and and [Ir(ppy)2(mdppy)], and The film having no th was used, and the film thickness was set to 40 nm. Layer 913 contains mPCCzPTzn-02, PCCP, [Ir(ppy)2(mdppy )] and a film containing TTPA, with a film thickness of 40 nm. The weight ratios of the different compounds in the light-emitting layer 913 are as shown in Table 1.

[0359] The electron transport layer 914 is made of mPCCzPTzn-02 having a film thickness of 20 nm and mPCCzPTzn-02 having a film thickness of 10 nm. 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthate A laminated film with NBphen was used.

[0360] The electron injection layer 915 was made of lithium fluoride (LiF) and had a film thickness of 1 nm.

[0361] The second electrode 903 was made of aluminum and had a film thickness of 200 nm. In an embodiment, the second electrode 903 functions as a cathode.

[0362] <Operation characteristics of light-emitting devices> The operating characteristics of the fabricated light-emitting device were measured. The luminance, chromaticity (CIE chromaticity), and A spectroradiometer (Topcon, SR-UL1R) was used to measure electroluminescence (EL) spectra. The measurements were carried out at room temperature (an atmosphere maintained at 23°C).

[0363] The light-emitting devices 1-1, 1-2, and 1-3 produced in this example were: As a result of the operating characteristics of the light-emitting devices 1-4 and 1-5, the current density-luminance The luminance vs. current efficiency characteristics are shown in Fig. 17, the voltage vs. luminance characteristics in Fig. 18, the luminance vs. current efficiency characteristics in Fig. 19, and the voltage vs. current density characteristics in Fig. 20. The respective intensity characteristics are shown in FIG.

[0364] In addition, each light-emitting device is supplied with 2.5mA / cm 2The electroluminescence spectrum when a current is passed through the The EL spectrum is shown in FIG.

[0365] Next, 1000 cd / m 2 The main initial characteristics of each light-emitting device in the vicinity are shown in Table 2 below. show.

[0366] [Table 2]

[0367] The light emitting devices 1-1 to 1-4 are light emitting devices 1-5, each of which is a light emitting device according to one embodiment of the present invention. This is a device that contains the compound 2Ph-mmAdtBuDPhA2Anth. As shown, the EL spectrum of light-emitting device 1-5 has a peak wavelength of 522 nm. The green light emitted from [Ir(ppy)2(mdppy)] was also observed. The EL spectra of light-emitting devices 1-1 to 1-4 have a peak wavelength of around 545 nm. The green luminescence was derived from 2Ph-mmAdtBuDPhA2Anth. In the light-emitting devices 1-1 to 1-4, the fluorescent material 2Ph -mmAdtBuDPhA2Anth receives excitation energy and emits light. Furthermore, from the above results, it can be seen that all of the light-emitting devices 1-1 to 1-5 It shows that the external quantum efficiency is high, exceeding 21%. The probability of generating singlet excitons by recombination of electrons (holes and electrons) is 25% at most. Therefore, if the light extraction efficiency to the outside is 30%, the external quantum efficiency of the fluorescent light-emitting device is However, in light-emitting devices 1-1 to 1-4, In this case, the external quantum efficiency was higher than 7.5%. The emission is due to singlet excitons generated by the recombination of injected carriers (holes and electrons). In addition to light, fluorescent materials emit light due to energy transfer from triplet excitons. This is because

[0368] In addition, the luminescence of the 2P-mmAdtBuDPhA2Anth contained in the luminescent layer varies depending on the concentration. In comparing Device 1-1 to Device 1-5, all of them have similar external quantum efficiencies. Therefore, the compound 2Ph-mmAdtBu, which is one embodiment of the present invention, DPhA2Anth is particularly problematic at high concentrations in the emissive layer of light-emitting devices. It was shown that the deactivation of triplet excitation energy could be suppressed, resulting in efficient light emission. In comparison between the light-emitting device 1-3 and the comparative light-emitting device 1-a, the light-emitting device 1-3 The ratio of 2Ph-mmAdtBuDPhA2Anth contained in the emitting layer to the same concentration of TTPA The external quantum efficiency of the comparative light-emitting device 1-a was less than half that of the light-emitting device 1-3. This is because the 2Ph-mmAdtBuDPhA2Ant h has a protecting group, which is different from the TTPA having no protecting group used in the comparative light-emitting device 1-a. Rather than suppressing the transfer of triplet excitation energy from the host due to the Dexter mechanism, This allows both singlet and triplet excitation energy to be efficiently converted into light. This means that it has been shown to have a significant impact on the external quantum efficiency. do.

[0369] Furthermore, for light-emitting devices 1-1 to 1-5, 50 mA / cm 2 In A current density driving test was carried out. The results are shown in Figure 33. From these results, it is clear that the guest, 2P It was found that increasing the concentration of h-mmAdtBuDPhA2Anth improved reliability. This is because increasing the concentration of the guest in the emitting layer increases the excitation energy in the emitting layer. This shows that the guest concentration can be efficiently converted into guest emission. By increasing the Dexter mechanism, the energy transfer from the host to the guest can be suppressed. The triplet excitation energy from the host to the guest via the Förster mechanism is This suggests that the migration speed can be increased. A light-emitting device using the compound can be said to have good luminous efficiency and reliability. . [Example]

[0370] In this example, a light-emitting device was manufactured using a compound according to one embodiment of the present invention, and its operating characteristics were evaluated. The light-emitting devices shown in this example are light-emitting device 2-1, light-emitting device 2-2, light-emitting device 2-3, light-emitting device 2-4, and light-emitting device 2-5; These light-emitting devices have the element structure shown in FIG. 16, and the configuration example of the light-emitting layer of the second embodiment 3, and specifically, the configuration shown in Table 3. The compound of the present invention, N,N'-bis[3,5-bis(2-methyl-2-phenylene-1-yl)-2-propanediol], contained in the light-emitting layer is (2-adamantyl)phenyl]-N,N'-bis(3,5-di-tert-butylphenyl)- 2-phenylanthracene-9,10-diamine (abbreviation: 2Ph-mmAdtB Although the content of uDPhA2Anth) is different, the other components are the same. As a comparative example of the light-emitting device, Comparative development using TTPA instead of compound 2Ph-mmAdtBuDPhA2Anth The optical device 2-a is shown. The chemical formulas of the materials used in this example are shown below.

[0371] [Table 3]

[0372] [ka]

[0373] <Light-emitting device configuration> The light-emitting device shown in this example has the same structure as in Example 2, as shown in FIG. The configuration different from 2 is a light emitting device 2-1, a light emitting device 2-2, a light emitting device 2-3, a light emitting device 2-4, a light emitting device 2-5, a light emitting device 2-6, a light emitting device 2-7, a light emitting device 2-8, a light emitting device 2-9, a light emitting device 2-10, a light emitting device 2-21, a light emitting device 2- The 3,3'- used in the hole transport layer 912 of the optical device 2-4 and the light-emitting device 2-5 Bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), tris(tris(triphenylphosphine)) used in the light-emitting layer [2-(1H-pyrazol-1-yl-κN 2 )phenyl-κC]iridium(III) (abbreviation: [Ir(ppz)3]), and 9,9'-(pyrimidine-4,6-diyldi- 3,1-phenylene)bis(9H-carbazole) (abbreviation: 4,6mCzP2Pm), The compound used for the electron transport layer 914 is 4,6mCzP2Pm.

[0374] <Operation characteristics of light-emitting devices> The operating characteristics of the fabricated light-emitting device were measured using the same method as in Example 2. Therefore, the explanation will be omitted.

[0375] The light-emitting devices 2-1, 2-2, and 2-3 produced in this example were As a result of the operating characteristics of the light-emitting devices 2-4 and 2-5, the current density-luminance The luminance vs. current efficiency characteristics are shown in Fig. 22, the voltage vs. luminance characteristics in Fig. 23, the luminance vs. current efficiency characteristics in Fig. 24, and the voltage vs. current density characteristics in Fig. 25. The respective intensity characteristics are shown in FIG.

[0376] In addition, each light-emitting device is supplied with 2.5mA / cm 2 The electroluminescence spectrum when a current is passed through the The EL spectrum is shown in FIG.

[0377] Next, 1000 cd / m 2 The main initial characteristics of each light-emitting device in the vicinity are shown in Table 4 below. show.

[0378] [Table 4]

[0379] The light emitting devices 2-1 to 2-4 are light emitting devices 2-5, each of which is a light emitting device according to one embodiment of the present invention. This is a device that contains the compound 2Ph-mmAdtBuDPhA2Anth. As shown, the EL spectrum of light-emitting device 2-5 has a peak wavelength of 531 nm. The emission spectra of 4,6mCzP2Pm and [Ir(ppz)3] are different from each other. , which showed green emission originating from the exciplex of 4,6mCzP2Pm and [Ir(ppz)3] The EL spectra of the light-emitting devices 2-1 to 2-4 have peak wavelengths of Green emission from 2Ph-mmAdtBuDPhA2Anth at around 545 nm From this, it can be seen that in the light-emitting devices 2-1 to 2-4, The luminescent material 2Ph-mmAdtBuDPhA2Anth receives the excitation energy. From the above results, it can be seen that light is emitted from light-emitting device 2-1. It can be seen that all of the samples 2-5 exhibit high external quantum efficiencies of 19% or more. The probability of singlet excitons being generated by recombination of injected carriers (holes and electrons) Therefore, if the light extraction efficiency to the outside is 30%, the The external quantum efficiency of the device is 7.5% at maximum. In Devices 2-4, the external quantum efficiency is higher than 7.5%. is a single charge generated by the recombination of carriers (holes and electrons) injected from a pair of electrodes. In addition to the emission from single excitons, the emission from energy transfer from triplet excitons or due to singlet excitons generated from triplet excitons by reverse intersystem crossing in exciplexes. This is because the emitted light is obtained from a fluorescent material.

[0380] In addition, the luminescence of the 2P-mmAdtBuDPhA2Anth contained in the luminescent layer varies depending on the concentration. In comparing Device 2-1 to Device 2-5, all of them have similar external quantum efficiencies. Therefore, the compound 2Ph-mmAdtBu, which is one embodiment of the present invention, DPhA2Anth is particularly problematic at high concentrations in the emissive layer of light-emitting devices. It was shown that the deactivation of triplet excitation energy could be suppressed, resulting in efficient light emission. In comparison between the light-emitting device 2-3 and the comparative light-emitting device 2-a, the light-emitting device 2-3 The ratio of 2Ph-mmAdtBuDPhA2Anth contained in the emitting layer to the same concentration of TTPA The external quantum efficiency of the comparative light-emitting device 2-a was less than half that of the light-emitting device 2-3. This is because the 2Ph-mmAdtBuDPhA2Ant h has a protecting group, which is different from the TTPA having no protecting group used in the comparative light-emitting device 2-a. Rather than suppressing the transfer of triplet excitation energy from the host due to the Dexter mechanism, This allows both singlet and triplet excitation energy to be efficiently converted into light. This means that it has been shown to have a significant impact on the external quantum efficiency. do.

[0381] ≪CV measurement results≫ Next, the 4,6mCzP2Pm and [Ir(ppz)3 The electrochemical properties (oxidation and reduction properties) of The measurement was carried out by CV measurement as follows.

[0382] The measurement device used was an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model). The solution used in the CV measurements was dehydrated dimethyl ether. Dimethylformamide (DMF) (Aldrich Corporation, 99.8%, Catalog No. 227 05-6) was used, and the supporting electrolyte was tetra-n-butylammonium perchlorate (nB u4NClO4) (Tokyo Chemical Industry Co., Ltd., Catalog No.: T0836) at 100 mmol / The measurement target is dissolved in a solution to a concentration of 2 mmol / L. The working electrode was a platinum electrode (PT, manufactured by BAS Co., Ltd.). E platinum electrode), and as an auxiliary electrode, a platinum electrode (B.A.S. Co., Ltd., VC-3 P 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°C). The scan rate during CV measurement was standardized to 0.1 V / sec. The oxidation potential Ea [V] and reduction potential Ec [V] relative to the reference electrode were measured. The potential of the α-reduction wave is defined as the midpoint potential of the α-reduction wave, and Ec is defined as the midpoint potential of the α-reduction wave. The potential energy of the reference electrode relative to the vacuum level is -4.94 eV. Therefore, the HOMO level [eV] = -4.94-Ea, the LUMO level [e V]=-4.94-Ec, calculate the HOMO and LUMO levels, respectively. It is possible.

[0383] The CV measurement showed that the oxidation potential of 4,6mCzP2Pm was 0.95 V and the reduction potential was -2.06 V. The HOMO level of 4,6mCzP2Pm calculated from CV measurements was -5. The LUMO level was 89 eV and -2.88 eV. The potential was 0.45 V and the reduction potential was -3.17 V. In addition, [I The HOMO level of [r(ppz)3] is -5.39 eV, and the LUMO level is -1.77 eV. It was.

[0384] As mentioned above, the LUMO level of 4,6mCzP2Pm is the same as that of [Ir(ppz)3]. The HOMO level of [Ir(ppz)3] is lower than the O level, and the HO level of 4,6mCzP2Pm Therefore, when this compound is used in the light-emitting layer, electrons and holes are efficiently transported. It is often injected into 4,6mCzP2Pm and [Ir(ppz)3], respectively, and 4,6mCzP 2Pm and [Ir(ppz)3] can form an exciplex. The emission energy of the EL spectrum of the light-emitting device 2-5 is 4,6mCzP2Pm The energy is close to the difference between the HOMO level and the LUMO level of [Ir(ppz)3]. It was also found that the emission was due to the exciplex formed between 4,6mCzP2Pm and [Ir(ppz)3]. It can be said that this is a coming light.

[0385] Furthermore, for the light-emitting devices 2-1 to 2-5, 50 mA / cm 2 In A current density driving test was carried out. The results are shown in Figure 34. From these results, it can be seen that the guest, 2P It was found that increasing the concentration of h-mmAdtBuDPhA2Anth improved reliability. This is because increasing the concentration of the guest in the emitting layer increases the excitation energy in the emitting layer. This shows that the guest concentration can be efficiently converted into guest emission. By increasing the Dexter mechanism, the energy transfer from the host to the guest can be suppressed. The triplet excitation energy from the host to the guest via the Förster mechanism is This suggests that the migration speed can be increased. A light-emitting device using the compound can be said to have good luminous efficiency and reliability. . [Example]

[0386] <Synthesis Example 2> In this example, a compound represented by structural formula (102) in Embodiment 1, which is one embodiment of the present invention, , N,N'-bis[3,5-bis(2-adamantyl)phenyl]-N,N'-bis[3 ,5-bis(3,5-di-tert-butylphenyl)phenyl]-2-phenylanthrene Helical-9,10-diamine (abbreviation: 2Ph-mmAdtBuDPhA2Anth-02 ) synthesis method will be explained. The structure of 2 is shown below.

[0387] [ka]

[0388] Step 1: 3,5-bis(2-adamantyl)-3',5'-bis(3,5-di-t Synthesis of (ert-butylphenyl)diphenylamine 3.6 g (7.2 mmol) of 3,5-bis(2-adamantyl)phenyltrifluoro Methanesulfonic acid was placed in a 200 mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen. 20 mL of tetrahydrofuran and 3.7 g (4.9 mmol) of bis(3,5-di-t ert-butylphenyl)aniline and 3.3 g (10 mmol) of cesium carbonate and 0. 40 g (0.64 mmol) of (±)-2,2'-bis(diphenylphosphino)-1, 1'-Binaphthyl (abbreviation: (±)-BINAP) was added, and the mixture was degassed under reduced pressure. To the mixture was added 0.10 g (0.45 mmol) of palladium(II) acetate, and the mixture was The mixture was stirred under a nitrogen stream at 70°C for 37 hours.

[0389] After stirring, 500 mL of toluene was added to the resulting mixture, and then Florisil (Wako Pure Chemical Industries, Ltd.) was added. Co., Ltd., Catalog No.: 066-05265), Celite (Wako Pure Chemical Industries, Ltd., Catalog number: 537-02305), and suction-filtered through aluminum oxide to obtain the filtrate. The obtained filtrate was concentrated to give a reddish brown solid.

[0390] This solid was purified by silica gel column chromatography (developing solvent: hexane:toluene=4: The resulting yellow-white solid was recrystallized with toluene. Upon crystallization, 3.5 g of the desired white solid was obtained in 59% yield. The system is shown in (b-1) below.

[0391] [ka]

[0392] In addition, the white solid obtained in step 1 above 1 The results of the H NMR measurements are shown below. From these results, 3,5-bis(2-adamantyl)-3',5'-bis(3,5-di-t It was found that (ert-butylphenyl)diphenylamine was obtained.

[0393] 1 H NMR(CD2Cl2,300MHz):σ=7.46-7.44(m,6H), 7.27-7.26(m,1H),7.22-7.21(m,2H),7.05(s,2) H),7.02(s,1H),6.00(bs,1H),3.01(m,2H),2.4 5(m,4H),2.03-1.76(m,20H),1.57-1.52(m,4H) ,1.37(s,36H).

[0394] <Step 2: Synthesis of 2Ph-mmAdtBuDPhA2Anth-02> 0.87 g (2.1 mmol) of 9,10-dibromo-2-phenylanthracene and 3 0.5g (4.2mmol) of 3,5-bis(2-adamantyl)-3',5'-bis(3 ,5-di-tert-butylphenyl)diphenylamine and 0.81 g (8.4 mmo l) sodium tert-butoxide and 60 mg (0.15 mmol) of 2-dichloroisothiazolinone. Cyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl (abbreviation: SP hos) was placed in a 200 mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen. 5 mL of xylene was added, and the mixture was degassed under reduced pressure. Then, 40 mg (70 μmol) of l) Bis(dibenzylideneacetone)palladium(0) was added and the mixture was subjected to a nitrogen gas flow. The mixture was stirred at 150°C for 6 hours.

[0395] After stirring, 500 mL of toluene was added to the resulting mixture, and then Florisil (Wako Pure Chemical Industries, Ltd.) was added. Co., Ltd., Catalog No.: 066-05265), Celite (Wako Pure Chemical Industries, Ltd., The resulting solution was filtered through alumina under suction to obtain a filtrate. The filtrate was concentrated to give a brown solid.

[0396] This solid was purified by silica gel column chromatography (developing solvent: hexane:toluene=9: The target yellow solid was obtained by purifying it using HPLC. The product was purified by HPLC to obtain a yellow solid in an amount of 0.57 The synthesis scheme of step 2 is shown below in (b-2).

[0397] [ka]

[0398] The resulting yellow solid (0.39 g) was purified by train sublimation. The pressure is 4.0 x 10 -2 The yellow solid was heated at 360°C for 15 hours under the conditions of 0.1 Pa. After purification by sublimation, the target yellow solid was obtained in an amount of 0.34 g with a recovery rate of 87%.

[0399] In addition, the yellow solid obtained in Step 2 above 1 The results of the H NMR measurements are shown below. Also, 1 The H NMR chart is shown in Figure 27. From this result, it is clear that 2Ph-mmAdtBuD It was found that PhA2Anth-02 (structural formula (102)) was obtained.

[0400] 1 H NMR(CD2Cl2,300MHz):σ=8.56-8.52(m,1H), 8.44-8.29(m,3H),7.69-7.62(m,1H),7.48-7.1 2(m,28H),7.05(m,2H),6.90(m,1H),2.94-2.82 (m,4H),2.24-2.02(m,8H),1.88-1.05(m,120H) .

[0401] Next, the absorption spectrum of the toluene solution of 2Ph-mmAdtBuDPhA2Anth-02 The results of measuring the emission spectrum are shown in Figure 28. The measurement method was the same as in Example 1. is the same as:

[0402] As shown in Figure 28, the toluene solution of 2Ph-mmAdtBuDPhA2Anth-02 is 48 An absorption peak is observed around 5 nm, and the emission wavelength peak is 537 nm (excitation wavelength 460 nm). ) was. [Example]

[0403] <Synthesis Example 3> In this example, a compound represented by structural formula (116) in Embodiment 1, which is one embodiment of the present invention, , N,N'-bis{3,5-bis(2-bicyclo[2.2.1]heptyl)phenyl}- N,N'-bis(3,5-di-tert-butylphenyl)-2-phenylanthracene Synthesis of 2-9,10-diamine (abbreviation: 2Ph-mmnbtBuDPhA2Anth) The structure of 2Ph-mmnbtBuDPhA2Anth is shown below. vinegar.

[0404] [ka]

[0405] The above 2Ph-mmnbtBuDPhA2Anth is Step 1 and Step 2 of Example 1. Instead of 2-adamantanone used in Step 2, 2-norbornanone was used in the synthesis. Scheme (c-1), synthesis scheme (c-2), synthesis scheme (c-3), synthesis scheme (c-4), synthetic scheme (c-5), and synthetic scheme (c-6) are used. The compound can be synthesized in the same manner as in Example 1.

[0406] Step 1: 3-(2-bicyclo[2.2.1]heptyl)-5-bromoanisole Synthesis> 6.7 g (25 mmol) of 3,5-dibromoanisole was placed in a 500 mL three-neck flask. The atmosphere in the flask was replaced with nitrogen, and 240 mL of tetrahydrofuran was added thereto, and the mixture was heated to -80°C. The solution was stirred at rt. 17 mL (27 mmol) of n-butyllithium (1.6 mol A 1 / L n-hexane solution was added dropwise and the mixture was stirred under a nitrogen atmosphere for 2 hours. Add 0.4g (31mmol) of 2-norbornanone and gradually return the temperature to room temperature. The mixture was stirred for 5 hours.

[0407] After stirring, water was added to the mixture, and the aqueous layer was extracted with ethyl acetate. The mixture was combined, washed with water and saturated brine, and then dried over magnesium sulfate. The precipitate was filtered off, and the filtrate was concentrated to give a yellow oil.

[0408] The obtained oil was placed in a 500 mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen. 100 mL of dichloromethane was added and stirred at 0° C. To this solution, 12 mL (75 mmol ) triethylsilane was added, and 19 mL (0.15 mol) of boron trifluoride etherate was added. The mixture was stirred for 15 hours while the temperature was returned to room temperature.

[0409] After stirring, the mixture was added dropwise to a saturated aqueous solution of sodium bicarbonate, and the aqueous layer was extracted with dichloromethane. The resulting extract and the organic layer were combined, washed with water and saturated brine, and then extracted with magnesium sulfate. The mixture was separated by gravity filtration, and the filtrate was concentrated to give a pale yellow oil. .

[0410] The resulting oil was purified by silica gel column chromatography (eluent: hexane / toluene) The solid was purified by HPLC ( The target colorless oil was obtained as a result of purification using a developing solvent (chloroform) in an amount of 4.7 g (yield: 6%). The synthesis scheme of step 1 is shown below in (c-1).

[0411] [ka]

[0412] In addition, the white solid obtained in step 1 above 1 The results of the H NMR measurements are shown below. From these results, 3-(2-bicyclo[2.2.1]heptyl)-5-bromoanisole It was found that it was obtained.

[0413] 1 H NMR(CDCl3,300MHz):σ=6.96(s,1H),6.87(m ,1H),6.70(s,1H),3.78(s,3H),3.18-3.11(m,1 H),2.40-2.32(m,2H),2.00-1.89(m,1H),1.57- 1.18(m,7H).

[0414] Step 2: Synthesis of 3,5-bis(2-bicyclo[2.2.1]heptyl)anisole > 4.7 g (17 mmol) of 3-(2-bicyclo[2.2.1]heptyl)-5-bromo Anisole was placed in a 500 mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen. 11 mL (18 mm) of tetrahydrofuran was added and stirred at -80°C. 1.6 mol / L n-hexane solution) was added dropwise, and the mixture was then heated under nitrogen. The mixture was stirred under reflux for 3 hours. Then, 2.2 g (20 mmol) of 2-norbornane was added to the mixture. The mixture was stirred for 15 hours while the temperature was gradually returned to room temperature.

[0415] After stirring, water was added to the mixture, and the aqueous layer was extracted with ethyl acetate. The mixture was combined, washed with water and saturated brine, and then dried over magnesium sulfate. The precipitate was filtered off, and the filtrate was concentrated to give a pale yellow oil.

[0416] The obtained oil was placed in a 500 mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen. 50 mL of dichloromethane was added and stirred at 0° C. To this solution, 8.0 mL (50 mmol) l) Add 12 mL (96 mmol) of triethylsilane and add 12 mL (96 mmol) of boron trifluoride etherate. The mixture was stirred for 15 hours while the temperature was returned to room temperature.

[0417] After stirring, the mixture was added dropwise to a saturated aqueous solution of sodium bicarbonate, and the aqueous layer was extracted with dichloromethane. The resulting extract and the organic layer were combined, washed with water and saturated brine, and then extracted with magnesium sulfate. The mixture was separated by gravity filtration, and the filtrate was concentrated to give a pale yellow oil. .

[0418] The resulting oil was purified by silica gel column chromatography (eluent: hexane / toluene) The resulting oil was purified by HPLC (development The target colorless oil was obtained in an amount of 3.4 g in a yield of 69%. The synthesis scheme of step 2 is shown below in (c-2).

[0419] [ka]

[0420] In addition, the white solid obtained in step 2 above 1 The results of the H NMR measurements are shown below. From this result, 3,5-bis(2-bicyclo[2.2.1]heptyl)anisole was obtained. It was found that

[0421] 1 H NMR(CDCl3,300MHz):σ=6.69(m,1H),6.59(m ,2H),3.80(s,3H),3.22-3.16(m,2H),2.40-2.3 0(m,4H),2.00-1.90(m,2H),1.59-1.19(m,14H) .

[0422] Step 3: Synthesis of 3,5-bis(2-bicyclo[2.2.1]heptyl)phenol > 3.4 g (11 mmol) of 3,5-bis(2-bicyclo[2.2.1]heptyl)aniline The sole was placed in a 300 mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen. of dichloromethane was added and the solution was stirred at 0° C. To this solution was added 23 mL of boron tribromide After the dropwise addition, the solution was The mixture was allowed to warm and stirred for 15 hours.

[0423] After stirring, the mixture was added dropwise to a saturated aqueous solution of sodium bicarbonate, and the aqueous layer of the resulting mixture was The extract was combined with the organic layer and washed with water and saturated brine. After that, it was dried over magnesium sulfate. The mixture was separated by gravity filtration, and the filtrate was concentrated. As a result, 3.1 g of the target white solid was obtained. The synthesis scheme of Step 3 is shown below in (c-3). show.

[0424] [ka]

[0425] In addition, the white solid obtained in step 3 above 1 The results of the H NMR measurements are shown below. From this result, 3,5-bis(2-bicyclo[2.2.1]heptyl)phenol was obtained. It was found that

[0426] 1 H NMR(CDCl3,300MHz):σ=6.67(m,1H),6.52(m ,2H),4.56(bs,1H),3.20-3.13(m,2H),2.38-2. 31(m,4H),1.99-1.89(m,2H),1.74-1.18(m,14H ).

[0427] Step 4: 3,5-bis(2-bicyclo[2.2.1]heptyl)phenyltriflate Synthesis of methylmethanesulfonic acid 3.1 g of 3,5-bis(2-bicyclo[2.2.1]heptyl)phenol was added to 300 ml The flask was then filled with nitrogen. 100 mL of dichloromethane was added. 5.0 mL (36 mmol) of triethylamine was added and stirred at 0°C. 10 mL of 18 mmol of trifluoromethanesulfonic anhydride in a 10 mL flask. The chloromethane solution was added dropwise, and the mixture was stirred for 15 hours while the temperature was returned to room temperature.

[0428] After stirring, 1N hydrochloric acid was added to the mixture, and the aqueous layer was extracted with dichloromethane. The aqueous solution and the organic layer were combined, washed with water and saturated brine, and then dried over magnesium sulfate. The mixture was separated by gravity filtration, and the filtrate was concentrated to give a brown oil.

[0429] This oil was purified by silica gel column chromatography (developing solvent: hexane). As a result, 3.8 g of the target colorless oil was obtained, with a total yield of 80% for Steps 3 and 4. The synthesis scheme of step 4 is shown below in (c-4).

[0430] [ka]

[0431] In addition, the white solid obtained in step 4 above 1 The results of the H NMR measurements are shown below. From these results, 3,5-bis(2-bicyclo[2.2.1]heptyl)phenyltriflate It was found that methylmethanesulfonic acid was obtained.

[0432] 1 H NMR(CDCl3,300MHz):σ=7.06(m,1H),6.91(m ,2H),3.26-3.19(m,2H),2.41-2.33(m,4H),2.0 5-1.95(m,2H),1.60-1.17(m,14H).

[0433] Step 5: 3,5-bis(2-bicyclo[2.2.1]heptyl)-3',5'-di Synthesis of tert-butyldiphenylamine 3.8 g (9.0 mmol) of 3,5-bis(2-bicyclo[2.2.1]heptyl)fluoride Phenyltrifluoromethanesulfonic acid was placed in a 200 mL three-neck flask and the flask was filled with nitrogen. 20 mL of tetrahydrofuran and 2.2 g (11 mmol) of 3, 5-Di-tert-butylaniline and 4.1 g (13 mmol) of cesium carbonate and 0. 75g (1.2mmol) of (±)-2,2'-bis(diphenylphosphino)-1,1 (±)-Binaphthyl (abbreviation: (±)-BINAP) was added, and the mixture was degassed under reduced pressure. To the mixture was added 0.18 g (0.80 mmol) of palladium(II) acetate, and the mixture was The mixture was stirred under a nitrogen stream at 70°C for 18 hours.

[0434] After stirring, 400 mL of toluene was added to the resulting mixture, and then Florisil (Wako Pure Chemical Industries, Ltd.) was added. Co., Ltd., Catalog No.: 066-05265), Celite (Wako Pure Chemical Industries, Ltd., Catalog number: 537-02305), and suction-filtered through aluminum oxide to obtain the filtrate. The obtained filtrate was concentrated to give a reddish brown solid.

[0435] This solid was purified by silica gel column chromatography (developing solvent: hexane:toluene=4: Purification by 1) gave the desired white solid (1.7 g, 39% yield). The synthesis scheme of is shown in (c-5) below.

[0436] [ka]

[0437] In addition, the white solid obtained in step 5 above 1 The results of the H NMR measurements are shown below. From these results, 3,5-bis(2-bicyclo[2.2.1]heptyl)-3',5'-bi It was found that bis(3,5-ditert-butylphenyl)diphenylamine was obtained. Ta.

[0438] 1 H NMR(CD2Cl2,300MHz):σ=6.99(m,1H),6.94( m,2H),6.76(m,2H),6.66(m,1H),5.76(bs,1H), 3.20-3.13(m,2H),2.39-2.30(m,4H),1.99-1.8 8(m,2H),1.59-1.44(m,4H),1.45-1.19(m,28H) .

[0439] <Step 6: Synthesis of 2Ph-mmnbtBuDPhA2Anth> 0.72 g (1.7 mmol) of 9,10-dibromo-2-phenylanthracene and 1 0.7g (3.5mmol) of 3,5-bis(2-bicyclo[2.2.1]heptyl)-3 ',5'-di-tert-butyldiphenylamine and 0.67 g (7.0 mmol) of Sodium tert-butoxide and 60 mg (0.15 mmol) of 2-dicyclohexane Xylphosphino-2',6'-dimethoxy-1,1'-biphenyl (abbreviation: SPhos ) was placed in a 200 mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen. of xylene was added, and the mixture was degassed under reduced pressure. Bis(dibenzylideneacetone)palladium(0) was added, and the mixture was heated under a nitrogen atmosphere for 1 The mixture was stirred at 50°C for 3 hours.

[0440] After stirring, 500 mL of toluene was added to the resulting mixture, and then Florisil (Wako Pure Chemical Industries, Ltd.) was added. Co., Ltd., Catalog No.: 066-05265), Celite (Wako Pure Chemical Industries, Ltd., The resulting solution was filtered through alumina under suction to obtain a filtrate. The filtrate was concentrated to give a brown solid.

[0441] This solid was purified by silica gel column chromatography (developing solvent: hexane:toluene=9: The target yellow solid was obtained by purifying it using HPLC. The product was purified by HPLC to obtain a yellow solid in an amount of 0.51 g. The synthesis scheme of Step 6 is shown below in (c-6).

[0442] [ka]

[0443] The resulting yellow solid (0.45 g) was purified by train sublimation. The purification was carried out by heating the yellow solid at 275°C for 15 hours under a pressure of 3.5 Pa. After the purification, the target yellow solid was obtained in a yield of 0.30 g and a recovery rate of 67%.

[0444] In addition, the yellow solid obtained in step 6 above 1 The results of the H NMR measurements are shown below. Also, 1 The H NMR chart is shown in Figure 29. From this result, it is clear that 2Ph-mmnbtBuD It was found that PhA2Anth (structural formula (116)) was obtained.

[0445] 1 H NMR(CD2Cl2,300MHz):σ=8.39(m,1H),8.25- 8.18(m,3H),7.65(m,1H),7.44-7.29(m,7H),7. 05-7.00(m,6H),6.76-6.63(m,6H),3.01(m,4H) ,2.19(m,8H),1.78(m,4H),1.44-0.95(m,64H).

[0446] Next, the absorption spectrum of 2Ph-mmnbtBuDPhA2Anth in toluene and The results of measuring the emission spectrum are shown in Figure 30. The measurement method was the same as that shown in Example 1. is.

[0447] As shown in Figure 30, the toluene solution of 2Ph-mmnbtBuDPhA2Anth exhibits a peak at 485 nm An absorption peak is observed around 535 nm (excitation wavelength 460 nm). It was. [Example]

[0448] <Synthesis Example 4> In this example, a compound represented by structural formula (108) in Embodiment 1, which is one embodiment of the present invention, , N,N'-bis[3,5-bis(1-adamantyl)phenyl]-N,N'-bis(3 ,5-di-tert-butylphenyl)-2-phenylanthracene-9,10-diamine This explains the synthesis method of 2Ph-mmAdtBuDPhA2Anth-03 The structure of 2Ph-mmAdtBuDPhA2Anth-03 is shown below.

[0449] [ka]

[0450] The above 2Ph-mmAdtBuDPhA2Anth-03 is used in step 5 of Example 1. The 3,5-bis(2-adamantyl)phenyltrifluoromethanesulfonic acid used in Instead, 3,5-bis(1-adamantyl)phenyl trifluoromethanesulfonic acid By using the methods shown in synthetic scheme (d-1) and synthetic scheme (d-2), It can be synthesized in the same manner as in Example 1.

[0451] [ka]

[0452] [ka] [Example]

[0453] <Synthesis Example 5> In this example, a compound represented by structural formula (120) in Embodiment 1, which is one embodiment of the present invention, , N,N'-bis{3,5-bis(tricyclo[5.2.1.0 2,6 ]Decan-8-I {N,N'-bis(3,5-di-tert-butylphenyl)-2-phenyl}-N,N'-bis(3,5-di-tert-butylphenyl)-2-phenyl Nylanthracene-9,10-diamine (abbreviation: 2Ph-mmTCDtBuDPhA2A The synthesis method of 2Ph-mmTCDtBuDPhA2An will be explained. The structure of th is shown below.

[0454] [ka]

[0455] Step 1: 3-Bromo-5-(tricyclo[[(5.2.1.0 2,6 ]Decan-8-I Synthesis of anisole 6.7 g (25 mmol) of 3,5-dibromoanisole was placed in a 500 mL three-neck flask. The atmosphere in the flask was replaced with nitrogen. 200 mL of tetrahydrofuran was added thereto, and the mixture was heated to -80°C. The solution was stirred at rt. 17 mL (27 mmol) of n-butyllithium (1.6 mol A 1 / L n-hexane solution was added dropwise and the mixture was stirred under a nitrogen stream for 2 hours. 0.3mL (30mmol) of tricyclo[5.2.1.0 2,6 ] Add decan-8-one The mixture was stirred for 15 hours while the temperature was gradually returned to room temperature.

[0456] After stirring, water was added to the mixture, and the aqueous layer was extracted with ethyl acetate. The mixture was combined, washed with water and saturated brine, and then dried over magnesium sulfate. The precipitate was filtered off, and the filtrate was concentrated to give a yellow oil.

[0457] The obtained oil was placed in a 500 mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen. 100 mL of dichloromethane was added and stirred at 0° C. To this solution, 12 mL (75 mmol ) triethylsilane was added, and 19 mL (0.15 mol) of boron trifluoride etherate was added. The mixture was stirred for 15 hours while the temperature was returned to room temperature.

[0458] After stirring, the mixture was added dropwise to a saturated aqueous solution of sodium bicarbonate, and the aqueous layer was extracted with dichloromethane. The resulting extract and the organic layer were combined, washed with water and saturated brine, and then extracted with magnesium sulfate. The mixture was separated by gravity filtration, and the filtrate was concentrated to give a pale yellow oil. .

[0459] The resulting oil was purified by silica gel column chromatography (eluent: hexane / toluene) The resulting solid was purified by HPLC ( The target colorless oil was obtained as a result of purification using a developing solvent (chloroform) in an amount of 6.6 g (yield: 8%). The synthesis scheme for step 1 is shown below in (e-1).

[0460] [ka]

[0461] In addition, the white solid obtained in step 1 above 1 The results of the H NMR measurements are shown below. From these results, 3-bromo-5-(tricyclo[5.2.1.0 2,6 ]Decan-8-I It was found that 1,3-diaminoanisole was obtained.

[0462] 1 H NMR(CDCl3,300MHz):σ=6.95(s,1H),6.86(m ,1H),6.69(s,1H),3.78(s,3H),3.15-3.08(m,1 H),2.17-2.06(m,2H),1.99-1.52(m,7H),1.33- 1.22(m,2H),1.14-0.85(m,3H).

[0463] Step 2: 3,5-bis(tricyclo[5.2.1.0 2,6 ]decane-8-yl) Synthesis of Anisole> 6.6g (20mmol) 3-bromo-5-(tricyclo[5.2.1.0 2,6 ]Deca (Benzene-8-yl)anisole was placed in a 500 mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen. 200 mL of tetrahydrofuran was added to the solution, and the mixture was stirred at -80°C. mL (22 mmol) of n-butyllithium (1.6 mol / L n-hexane solution) The mixture was stirred under a nitrogen atmosphere for 3 hours. Tricyclo[5.2.1.0 2,6 ] Add decan-8-one and gradually return the temperature to room temperature. The mixture was stirred for 15 hours.

[0464] After stirring, water was added to the mixture, and the aqueous layer was extracted with ethyl acetate. The mixture was combined, washed with water and saturated brine, and then dried over magnesium sulfate. The precipitate was filtered off, and the filtrate was concentrated to give a pale yellow oil.

[0465] The obtained oil was placed in a 500 mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen. 70 mL of dichloromethane was added and stirred at 0° C. To this solution was added 9.7 mL (61 mmol) of l) Add triethylsilane and 15 mL (0.12 mol) of boron trifluoride etherate. The mixture was stirred for 15 hours while the temperature was returned to room temperature.

[0466] After stirring, the mixture was added dropwise to a saturated aqueous solution of sodium bicarbonate, and the aqueous layer was extracted with dichloromethane. The resulting extract and the organic layer were combined, washed with water and saturated brine, and then extracted with magnesium sulfate. The mixture was separated by gravity filtration, and the filtrate was concentrated to give a pale yellow solid.

[0467] The resulting oil was purified by silica gel column chromatography (eluent: hexane / toluene) 4:1), and 6.2 g of the target colorless oil was obtained. The oily substance was purified by HPLC (eluent: chloroform) to give the desired colorless oily substance. The synthesis scheme of Step 2 is shown in (e-2) below.

[0468] [ka]

[0469] In addition, the colorless oil obtained in step 2 above 1 The results of H NMR measurements are shown below. From these results, it is clear that 3,5-bis(tricyclo[5.2.1.0 2,6 ]Decan-8-yl ) It was found that anisole was obtained.

[0470] 1 H NMR(CDCl3,300MHz):σ=6.69(s,1H),6.59(s ,2H),3.80(s,3H),3.19-3.12(m,2H),2.17-2.0 6(m,4H),2.01-1.51(m,14H),1.40-1.32(m,2H) ,1.26-1.23(m,2H),1.11-0.85(m,6H).

[0471] Step 3: 3,5-bis(tricyclo[5.2.1.0 2,6 ]decane-8-yl) Synthesis of phenol> 4.0 g (11 mmol) of 3,5-bis(tricyclo[5.2.1.0 2,6 ] Deccan (-8-yl)anisole was placed in a 300 mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen. 100 mL of dichloromethane was added thereto, and the solution was stirred at 0°C. mL of boron tribromide (1.0 mol / L dichloromethane solution, 22 mmol) was added dropwise. After the dropwise addition, the solution was stirred for 15 hours while being returned to room temperature.

[0472] After stirring, the mixture was added dropwise to a saturated aqueous solution of sodium bicarbonate, and the aqueous layer of the resulting mixture was The extract was combined with the organic layer and washed with water and saturated brine. After that, it was dried over magnesium sulfate. The mixture was separated by gravity filtration, and the filtrate was concentrated. As a result, 4.2 g of the target gray solid was obtained. The synthesis scheme of Step 3 is shown below in (e-3). show.

[0473] [ka]

[0474] In addition, the white solid obtained in step 3 above 1 The results of the H NMR measurements are shown below. From these results, 3,5-bis(tricyclo[5.2.1.0 2,6 ]decane-8-yl) It was found that phenol was obtained.

[0475] 1 H NMR(CDCl3,300MHz):σ=6.67(s,1H),6.51(s ,2H),4.55(bs,1H),3.16-3.09(m,2H),2.16-2. 06(m,4H),2.00-1.51(m,14H),1.37-1.29(m,2H ),1.25-1.22(m,2H),1.12-0.85(m,6H).

[0476] Step 4: 3,5-bis(tricyclo[5.2.1.0 2,6 ]decane-8-yl) Synthesis of phenyltrifluoromethanesulfonic acid> 4.2 g of 3,5-bis(tricyclo[5.2.1.0 2,6 ]Decan-8-yl)phen The alcohol was placed in a 300 mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen. of dichloromethane and 5.0 mL (36 mmol) of triethylamine were added and stirred at 0°C. The mixture was stirred. 3.0 mL (18 mmol) of trifluoromethanesulfonic anhydride was added to the mixture. 10 mL of dichloromethane solution was added dropwise, and the mixture was stirred for 15 hours while the temperature was returned to room temperature.

[0477] After stirring, 1N hydrochloric acid was added to the mixture, and the aqueous layer was extracted with dichloromethane. The aqueous solution and the organic layer were combined, washed with water and saturated brine, and then dried over magnesium sulfate. The mixture was separated by gravity filtration, and the filtrate was concentrated to give a brown oil.

[0478] This oil was purified by silica gel column chromatography (developing solvent: hexane). As a result, 3.6 g of the target colorless oil was obtained, with a total yield of 65% for Steps 3 and 4. The synthesis scheme of Step 4 is shown below in (e-4).

[0479] [ka]

[0480] In addition, the colorless oil obtained in step 4 above 1 The results of H NMR measurements are shown below. From these results, it is clear that 3,5-bis(tricyclo[5.2.1.0 2,6 ]Decan-8-yl ) It was found that phenyltrifluoromethanesulfonic acid was obtained.

[0481] 1 H NMR(CDCl3,300MHz):σ=7.07(s,1H),6.90(s ,2H),3.23-3.16(m,2H),2.19-2.09(m,4H),2.0 7-1.97(m,2H),1.89-1.57(m,12H),1.34-1.25( m,4H), 1.13-0.86(m,6H).

[0482] Step 5: 3,5-bis(tricyclo[5.2.1.0 2,6 ]decane-8-yl) Synthesis of 3',5'-di-tert-butyldiphenylamine 3.6 g (7.2 mmol) of 3,5-bis(tricyclo[5.2.1.0 2,6 ]Deca (phenyl-8-yl)phenyl trifluoromethanesulfonic acid in a 200 mL three-neck flask. The atmosphere in the flask was replaced with nitrogen. 20 mL of tetrahydrofuran and 1.7 g (8. 3 mmol) of 3,5-di-tert-butylaniline and 3.5 g (11 mmol) of charcoal Cesium phosphate and 1.1 g (1.7 mmol) of (±)-2,2'-bis(diphenylphosphine) (±)-1,1'-binaphthyl (abbreviation: (±)-BINAP) was added, and the mixture was reduced. After degassing under pressure, 0.20 g (0.89 mmol) of palladium(II) acetate was added to the mixture. The mixture was then stirred at 70°C under a nitrogen stream for 24 hours.

[0483] After stirring, 500 mL of toluene was added to the resulting mixture, and then Florisil (Wako Pure Chemical Industries, Ltd.) was added. Co., Ltd., Catalog No.: 066-05265), Celite (Wako Pure Chemical Industries, Ltd., Catalog number: 537-02305), and suction-filtered through aluminum oxide to obtain the filtrate. The obtained filtrate was concentrated to give a reddish brown solid.

[0484] This solid was purified by silica gel column chromatography (developing solvent: hexane:toluene=4: Purification by 1) gave the desired white solid, 3.3 g, in 83% yield. The synthesis scheme of is shown in (e-5) below.

[0485] [ka]

[0486] In addition, the white solid obtained in step 5 above 1 The results of the H NMR measurements are shown below. From these results, 3,5-bis(tricyclo[5.2.1.0 2,6 ]decane-8-yl) It was found that 3',5'-di-tert-butyldiphenylamine was obtained.

[0487] 1 H NMR(CD2Cl2,300MHz):σ=7.00(m,1H),6.94( m,2H),6.75(m,2H),6.66(m,1H),5.75(bs,1H), 3.17-3.10(m,2H),2.16-2.05(m,4H),1.98-1.8 3(m,8H),1.75-1.56(m,6H),1.37-0.87(m,28H) .

[0488] <Step 6: Synthesis of 2Ph-mmTCDtBuDPhA2Anth> 0.41 g (0.99 mmol) of 9,10-dibromo-2-phenylanthracene, 1.1 g (2.0 mmol) of 3,5-bis(tricyclo[5.2.1.0 2,6 ]Deca 0.29 g (phenyl-8-yl)-3',5'-di-tert-butyldiphenylamine 3.0 mmol) sodium tert-butoxide and 80 mg (0.19 mmol) ) 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl (abbreviation: SPhos) was placed in a 200 mL three-neck flask, and the atmosphere inside the flask was replaced with nitrogen. 10 mL of xylene was added to the mixture, and the mixture was degassed under reduced pressure. (0.10 mmol) of bis(dibenzylideneacetone)palladium(0) was added, and this The mixture was stirred under a nitrogen stream at 150° C. for 5 hours.

[0489] After stirring, 500 mL of toluene was added to the resulting mixture, and then Florisil (Wako Pure Chemical Industries, Ltd.) was added. Co., Ltd., Catalog No.: 066-05265), Celite (Wako Pure Chemical Industries, Ltd., The resulting solution was filtered through alumina under suction to obtain a filtrate. The filtrate was concentrated to give a brown solid.

[0490] This solid was purified by silica gel column chromatography (developing solvent: hexane:toluene=9: The concentration ratio was gradually changed from 1 to 17:3, and the target yellow solid was obtained. The obtained yellow solid was recrystallized with ethyl acetate and methanol, and the desired yellow compound was obtained. 0.17 g of a colored solid was obtained in a yield of 13%. The synthesis scheme for Step 6 is shown below in (e-6). show.

[0491] [ka]

[0492] The resulting yellow solid (0.94 g) was purified by train sublimation. The purification was carried out by heating the yellow solid at 305°C for 15 hours under a pressure of 5.7 Pa. After the purification, the target yellow solid was obtained in a yield of 0.79 g and a recovery rate of 84%.

[0493] In addition, the yellow solid obtained in step 6 above 1The results of the H NMR measurements are shown below. Also, 1 The H NMR chart is shown in Figure 31. From this result, it is clear that 2Ph-mmTCDtBu It was found that DPhA2Anth (structural formula (120)) was obtained.

[0494] 1 H NMR(CD2Cl2,300MHz):σ=8.40-8.39(m,1H), 8.25-8.16(m,3H),7.67-7.61(m,1H),7.43-7.2 7(m,7H),7.09-7.01(m,6H),6.79-6.63(m,6H), 3.00(m,4H),1.95-1.43(m,36H),1.18-0.82(m, 56H).

[0495] Next, the absorption spectrum of 2Ph-mmTCDtBuDPhA2Anth in toluene and The results of measuring the emission spectrum are shown in Figure 32. The measurement method was the same as that shown in Example 1. It seems that

[0496] As shown in Figure 32, the toluene solution of 2Ph-mmTCDtBuDPhA2Anth is 488n An absorption peak is observed around m, and the emission wavelength peak is 537 nm (excitation wavelength 460 nm). there were. [Example]

[0497] In this example, a light-emitting device was manufactured using a compound according to one embodiment of the present invention, and its operating characteristics were evaluated. The light-emitting devices shown in this example are Light-emitting Device 3-1 and Light-emitting Device 3 -2, light-emitting device 3-3, light-emitting device 3-4, and light-emitting device 3-5, These light-emitting devices have the element structure shown in FIG. 16 and are the same as the fifth example of the light-emitting layer configuration of the second embodiment. Specifically, the light-emitting device has the configuration shown in Table 5. The compound of one embodiment of the present invention, N,N'-bis[3,5-bis( 2-adamantyl)phenyl]-N,N'-bis[3,5-bis(3,5-di-tert -butylphenyl)phenyl]-2-phenylanthracene-9,10-diamine (abbreviated :2Ph-mmAdtBuDPhA2Anth-02) (Structural formula 102) content is different The chemical formulas of the materials used in this example are shown below.

[0498] [Table 5]

[0499] [ka]

[0500] <Light-emitting device configuration> The light-emitting device shown in this example has the same structure as in Example 2, as shown in FIG. The configuration different from that of 2 is that of the light emitting device 3-1, the light emitting device 3-2, the light emitting device 3-3, and and the 2Ph-mmAdtBuDPhA2Anth used in the light-emitting layer of light-emitting device 3-4. -02.

[0501] <Operation characteristics of light-emitting devices> The operating characteristics of the fabricated light-emitting device were measured. The luminance, chromaticity (CIE chromaticity), and A spectroradiometer (Topcon, SR-UL1R) was used to measure electroluminescence (EL) spectra. The measurements were carried out at room temperature (an atmosphere maintained at 23°C).

[0502] The light-emitting devices 3-1, 3-2, and 3-3 produced in this example were: As a result of the operating characteristics of the light-emitting devices 3-4 and 3-5, the current density-luminance The luminance vs. current efficiency characteristics are shown in Figure 35, the voltage vs. luminance characteristics in Figure 36, the luminance vs. current efficiency characteristics in Figure 37, and the voltage vs. current density characteristics in Figure 38. The luminance characteristics are shown in FIG. 38, and the luminance-external quantum efficiency characteristics are shown in FIG.

[0503] In addition, each light-emitting device is supplied with 2.5mA / cm 2 The electroluminescence spectrum when a current is passed through the The EL spectrum is shown in Figure 40.

[0504] Next, 1000 cd / m 2 The main initial characteristics of each light-emitting device in the vicinity are shown in Table 6 below. show.

[0505] [Table 6]

[0506] The light emitting devices 3-1 to 3-4 are light emitting devices 3-5, each of which is a light emitting device according to one embodiment of the present invention. This is a device that contains the compound 2Ph-mmAdtBuDPhA2Anth-02. As shown in Figure 40, the EL spectrum of the light-emitting device 3-5 has a peak wavelength of 522 nm. The green light emitted from [Ir(ppy)2(mdppy)] was also observed. The EL spectra of devices 3-1 to 3-4 have a peak wavelength of around 540 nm. The green luminescence from 2Ph-mmAdtBuDPhA2Anth-02 was observed. Therefore, in the light-emitting devices 3-1 to 3-4, the fluorescent material 2Ph-mmAdtBuDPhA2Anth-02 receives the excitation energy and emits From the above results, it can be seen that the light-emitting device 3-1 is 3-5 all show high external quantum efficiencies of 18% or more. Probability of singlet excitons produced by recombination of injected carriers (holes and electrons) Therefore, if the light extraction efficiency to the outside is set to 30%, the The external quantum efficiency of the device is 7.5% at maximum. In Device 3-4, the external quantum efficiency was higher than 7.5%. , a singlet generated by the recombination of carriers (holes and electrons) injected from a pair of electrodes In addition to the emission from excitons, the emission from the energy transfer from triplet excitons is called fluorescence. This is because it is obtained from a photoluminescent material.

[0507] In addition, the concentration of 2Ph-mmAdtBuDPhA2Anth-02 in the light-emitting layer was different. In comparing the light-emitting devices 3-1 to 3-5, all of them have the same external quantum efficiency. Therefore, the compound 2Ph-mmAd, which is one embodiment of the present invention, tBuDPhA2Anth-02 is particularly effective in the light-emitting layer of light-emitting devices at high concentrations. It was shown that the deactivation of triplet excitation energy, which is a major problem in photoluminescence, can be suppressed, resulting in efficient light emission. It was. [Example]

[0508] In this example, a light-emitting device was manufactured using a compound according to one embodiment of the present invention, and its operating characteristics were evaluated. The light-emitting devices shown in this example are light-emitting device 4-1, light-emitting device 4-2, and light-emitting device 4-3. 4-2, light-emitting device 4-3, light-emitting device 4-4, and light-emitting device 4-5; These light-emitting devices have the element structure shown in FIG. 16, and the configuration example of the light-emitting layer of the second embodiment 3, and specifically, the configuration shown in Table 7. The compound of the present invention, N,N'-bis[3,5-bis(2-methyl-2-phenylene-1-yl)-2-propanediol], contained in the light-emitting layer is (2-adamantyl)phenyl]-N,N'-bis[3,5-bis(3,5-di-tert- t-butylphenyl)phenyl]-2-phenylanthracene-9,10-diamine (abbreviation The content of 2Ph-mmAdtBuDPhA2Anth-02) (structural formula 102) is different. However, the other configurations are the same. The chemical formulas of the materials used in this example are shown below. .

[0509] [Table 7]

[0510] [ka]

[0511] <Light-emitting device configuration> The light-emitting device shown in this example has the same structure as in Example 8, as shown in FIG. The configuration different from that of the light emitting device 8 is a light emitting device 4-1, a light emitting device 4-2, a light emitting device 4-3, a light emitting device 4-4, a light emitting device 4-5, a light emitting device 4-6, a light emitting device 4-7, a light emitting device 4-8, a light emitting device 4-9, a light emitting device 4-1, a light emitting device 4-2, a light The 3,3'- used in the hole transport layer 912 of the optical device 4-4 and the light-emitting device 4-5 Bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), tris(tris(triphenylphosphine)) used in the light-emitting layer [2-(1H-pyrazol-1-yl-κN2)phenyl-κC]iridium(III) (abbreviation: [Ir(ppz)3]), and 9,9'-(pyrimidine-4,6-diyldi- 3,1-phenylene)bis(9H-carbazole) (abbreviation: 4,6mCzP2Pm), The compound used for the electron transport layer 914 is 4,6mCzP2Pm.

[0512] <Operation characteristics of light-emitting devices> The operating characteristics of the fabricated light-emitting device were measured using the same method as in Example 8. Therefore, the explanation will be omitted.

[0513] The light-emitting devices 4-1, 4-2, and 4-3 produced in this example were: As a result of the operating characteristics of the light-emitting device 4-4 and the light-emitting device 4-5, the current density-luminance The luminance vs. current efficiency characteristics are shown in Figure 41, the voltage vs. luminance characteristics in Figure 42, the luminance vs. current efficiency characteristics in Figure 43, and the voltage vs. current density characteristics in Figure 44. The luminance characteristics are shown in FIG. 44, and the luminance-external quantum efficiency characteristics are shown in FIG.

[0514] In addition, each light-emitting device is supplied with 2.5mA / cm 2 The electroluminescence spectrum when a current is passed through the The EL spectrum is shown in Figure 46.

[0515] Next, 1000 cd / m 2 The main initial characteristics of each light-emitting device in the vicinity are shown in Table 8 below. show.

[0516] [Table 8]

[0517] The light emitting devices 4-1 to 4-4 are light emitting devices 4-5, each of which is a light emitting device according to one embodiment of the present invention. This is a device that contains the compound 2Ph-mmAdtBuDPhA2Anth-02. As shown in Figure 46, the EL spectrum of the light-emitting device 4-5 has a peak wavelength of 531 nm. The emission spectra of 4,6mCzP2Pm and [Ir(ppz)3] are Green emission originates from the exciplex of 4,6mCzP2Pm and [Ir(ppz)3]. The EL spectra of the light-emitting devices 4-1 to 4-4 show peaks The wavelength is around 540 nm, derived from 2Ph-mmAdtBuDPhA2Anth-02 This indicates that the light-emitting devices 4-1 to 4-4 emit green light. In this case, the fluorescent substance 2Ph-mmAdtBuDPhA2Anth-02 is used as the excitation emitter. It can be seen that the light-emitting device receives energy and emits light. It was found that all of the light-emitting devices 1 to 4-5 exhibited high external quantum efficiencies of 19% or more. The electrons generated by the recombination of carriers (holes and electrons) injected from a pair of electrodes Since the probability of generating doublet excitons is 25% at most, the light extraction efficiency to the outside is set to 30%. In this case, the external quantum efficiency of the fluorescent light-emitting device is at most 7.5%. In the light-emitting devices 4-1 to 4-4, the external quantum efficiency was higher than 7.5%. This is due to the recombination of carriers (holes and electrons) injected from a pair of electrodes. In addition to the emission from singlet excitons generated by the Emission from the electron transport or from triplet excitons generated by reverse intersystem crossing in exciplexes This is because the light emitted from the fluorescent material originates from singlet excitons.

[0518] In addition, the concentration of 2Ph-mmAdtBuDPhA2Anth-02 in the light-emitting layer was different. In comparing the light-emitting devices 4-1 to 4-5, the external quantum efficiency was similar. Therefore, the compound 2Ph-mmAd, which is one embodiment of the present invention, tBuDPhA2Anth-02 is particularly effective in the light-emitting layer of light-emitting devices at high concentrations. It was shown that the deactivation of triplet excitation energy, which is a major problem in photoluminescence, can be suppressed, resulting in efficient light emission. It was.

[0519] Furthermore, for the light-emitting devices 4-1 to 4-5, 50 mA / cm 2 In A current density driving test was carried out. The results are shown in Figure 47. From these results, the guest, 2P Increasing the concentration of h-mmAdtBuDPhA2Anth-02 improved reliability. This is because increasing the concentration of the guest in the emitting layer increases the excited energy in the emitting layer. This shows that the energy can be efficiently converted into the light emission of the guest. By increasing the concentration of , the energy transfer from the host to the guest due to the Dexter mechanism is suppressed. The triplet excitation energy is also suppressed by the Förster mechanism from the host to the guest. This suggests that the energy transfer rate can be increased. A light-emitting device using a certain compound is said to have good luminous efficiency and reliability. I can say. [Example]

[0520] In this example, a light-emitting device was manufactured using a compound according to one embodiment of the present invention, and its operating characteristics were evaluated. The light-emitting devices shown in this example are light-emitting device 5-1 and light-emitting device 5- -2, light emitting device 5-3, light emitting device 5-4, and light emitting device 5-5, These light-emitting devices have the element structure shown in FIG. 16 and are the same as the fifth example of the light-emitting layer configuration of the second embodiment. Specifically, it has the configuration shown in Table 9. The compound of one embodiment of the present invention, N,N'-bis{3,5-bis( 2-bicyclo[2.2.1]heptyl)phenyl}-N,N'-bis(3,5-di-tert-butyl) rt-butylphenyl)-2-phenylanthracene-9,10-diamine (abbreviation: 2P h-mmnbtBuDPhA2Anth) (Structural formula 116) content is different, but other The chemical formulas of the materials used in this example are shown below.

[0521] [Table 9]

[0522] [ka]

[0523] <Light-emitting device configuration> The light-emitting device shown in this example has the same structure as in Example 2, as shown in FIG. The configuration different from that of the light emitting device 2 is the light emitting device 5-1, the light emitting device 5-2, the light emitting device 5-3, and the light emitting device 5-4. and 2Ph-mmnbtBuDPhA2Anth used in the light-emitting layer of light-emitting device 5-4. is.

[0524] <Operation characteristics of light-emitting devices> The operating characteristics of the fabricated light-emitting device were measured. The luminance, chromaticity (CIE chromaticity), and A spectroradiometer (Topcon, SR-UL1R) was used to measure electroluminescence (EL) spectra. The measurements were carried out at room temperature (an atmosphere maintained at 23°C).

[0525] The light-emitting devices 5-1, 5-2, 5-3, and 5-4 prepared in this example were As a result of the operating characteristics of the light-emitting device 5-4 and the light-emitting device 5-5, the current density-luminance The luminance vs. current efficiency characteristics are shown in Figure 48, the voltage vs. luminance characteristics in Figure 49, the luminance vs. current efficiency characteristics in Figure 50, and the voltage vs. current density characteristics in Figure 51. The luminance characteristics are shown in FIG. 51, and the luminance-external quantum efficiency characteristics are shown in FIG.

[0526] In addition, each light-emitting device is supplied with 2.5mA / cm 2 The electroluminescence spectrum when a current is passed through the The EL spectrum is shown in Figure 53.

[0527] Next, 1000 cd / m 2 The main initial characteristics of each light-emitting device in the vicinity are shown in Table 10 below. Shown below.

[0528] [Table 10]

[0529] The light emitting devices 5-1 to 5-4 are light emitting devices 5-5 and 5-6, respectively. This is a device that contains the compound 2Ph-mmnbtBuDPhA2Anth. As shown, the EL spectrum of the light-emitting device 5-5 has a peak wavelength of 522 nm. The green light emitted from [Ir(ppy)2(mdppy)] was also observed. The EL spectra of the light-emitting devices 5-1 to 5-4 have a peak wavelength of around 540 nm. The green luminescence was derived from 2Ph-mmnbtBuDPhA2Anth. Therefore, in the light-emitting devices 5-1 to 5-4, the fluorescent material 2Ph It was found that -mmnbtBuDPhA2Anth receives excitation energy and emits light. Furthermore, from the above results, it can be seen that the light-emitting devices 5-1 to 5-5 are all It shows that the device exhibits a high external quantum efficiency of over 16%. The probability of generating singlet excitons by recombination of electrons (holes and electrons) is 25% at most. Therefore, if the light extraction efficiency to the outside is 30%, the external quantum efficiency of the fluorescent light-emitting device is However, in the light-emitting devices 5-1 to 5-4, In this case, the external quantum efficiency was higher than 7.5%. The emission is due to singlet excitons generated by the recombination of injected carriers (holes and electrons). In addition to light, fluorescent materials emit light due to energy transfer from triplet excitons. This is because

[0530] In addition, the luminescence of the 2P-mmnbtBuDPhA2Anth contained in the luminescent layer differs depending on its concentration. In comparing Device 5-1 to Device 5-5, all of them have similar external quantum efficiency. Therefore, the compound 2Ph-mmnbtBu, which is one embodiment of the present invention, DPhA2Anth is particularly problematic at high concentrations in the emissive layer of light-emitting devices. It was shown that the deactivation of triplet excitation energy could be suppressed, resulting in efficient light emission. [Example]

[0531] In this example, a light-emitting device was manufactured using a compound according to one embodiment of the present invention, and its operating characteristics were evaluated. The light-emitting devices shown in this example are light-emitting device 6-1, light-emitting device 6-2, light-emitting device 6-3, light-emitting device 6-4, and light-emitting device 6-5; These light-emitting devices have the element structure shown in FIG. 16, and the configuration example of the light-emitting layer of the second embodiment 3, and specifically, the configuration shown in Table 11. The compound of one embodiment of the present invention, N,N'-bis{3,5-bis(3,5-bis)- {N,N'-bis(2-bicyclo[2.2.1]heptyl)phenyl}-N,N'-bis(3,5-di tert-butylphenyl)-2-phenylanthracene-9,10-diamine (abbreviation: The content of 2Ph-mmnbtBuDPhA2Anth) (structural formula 116) is different, but The other structures are the same as those of the first embodiment. The chemical formulas of the materials used in this embodiment are shown below.

[0532] [Table 11]

[0533] [ka]

[0534] <Light-emitting device configuration> The light-emitting device shown in this example has the same structure as in Example 10, as shown in FIG. The configuration different from Example 10 is that of the light-emitting device 6-1, the light-emitting device 6-2, and the light-emitting device 6-3. , 3,3 used in the hole transport layer 912 of the light-emitting device 6-4 and the light-emitting device 6-5. '-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), the Tris[2-(1H-pyrazol-1-yl-κN2)phenyl-κC]iridium(II I) (abbreviation: [Ir(ppz)3]), and 9,9'-(pyrimidine-4,6-diyl Di-3,1-phenylene)bis(9H-carbazole) (abbreviation: 4,6mCzP2Pm) The compound used in the electron transport layer 914 is 4,6mCzP2Pm.

[0535] <Operation characteristics of light-emitting devices> The operating characteristics of the fabricated light-emitting device were measured. The measurement method was the same as in Example 10. Therefore, the explanation will be omitted.

[0536] The light-emitting devices 6-1, 6-2, 6-3, and 6-4 prepared in this example are shown below. As a result of the operating characteristics of the light-emitting device 6-4 and the light-emitting device 6-5, the current density-luminance The luminance vs. current efficiency characteristics are shown in Figure 54, the voltage vs. luminance characteristics in Figure 55, the luminance vs. current efficiency characteristics in Figure 56, and the voltage vs. current density characteristics in Figure 57. The luminance characteristics are shown in FIG. 57, and the luminance-external quantum efficiency characteristics are shown in FIG.

[0537] In addition, each light-emitting device is supplied with 2.5mA / cm 2 The electroluminescence spectrum when a current is passed through the The EL spectrum is shown in Figure 59.

[0538] Next, 1000 cd / m 2 The main initial characteristics of each light-emitting device in the vicinity are shown in Table 12 below. Shown below.

[0539] [Table 12]

[0540] The light emitting devices 6-1 to 6-4 are light emitting devices 6-5 and 6-6. This is a device that contains the compound 2Ph-mmnbtBuDPhA2Anth. As shown, the EL spectrum of the light-emitting device 6-5 has a peak wavelength of 531 nm. The emission spectra of 4,6mCzP2Pm and [Ir(ppz)3] are different from each other. , which showed green emission originating from the exciplex of 4,6mCzP2Pm and [Ir(ppz)3] The EL spectra of the light-emitting devices 6-1 to 6-4 have peak wavelengths of Green emission from 2Ph-mmnbtBuDPhA2Anth at around 540 nm From this, it can be seen that in the light-emitting devices 6-1 to 6-4, The luminescent material 2Ph-mmnbtBuDPhA2Anth receives the excitation energy. From the above results, it can be seen that light is emitted from light-emitting device 6-1. It can be seen that all of the samples 6-5 exhibit high external quantum efficiencies of 19% or more. The probability of singlet excitons being generated by recombination of injected carriers (holes and electrons) Therefore, if the light extraction efficiency to the outside is 30%, the The external quantum efficiency of the device is 7.5% at maximum. In Device 6-4, the external quantum efficiency was higher than 7.5%. is a single charge generated by the recombination of carriers (holes and electrons) injected from a pair of electrodes. In addition to the emission from single excitons, the emission from energy transfer from triplet excitons or due to singlet excitons generated from triplet excitons by reverse intersystem crossing in exciplexes. This is because the emitted light is obtained from a fluorescent material.

[0541] In addition, the luminescence of the 2P-mmnbtBuDPhA2Anth contained in the luminescent layer differs depending on its concentration. In comparing Device 6-1 to Device 6-5, all of them have similar external quantum efficiency. Therefore, the compound 2Ph-mmnbtBu, which is one embodiment of the present invention, DPhA2Anth is particularly problematic at high concentrations in the emissive layer of light-emitting devices. It was shown that the deactivation of triplet excitation energy could be suppressed, resulting in efficient light emission.

[0542] Furthermore, for the light-emitting devices 6-1 to 6-5, 50 mA / cm 2 In A current density driving test was carried out. The results are shown in Figure 60. From these results, the guest, 2P It was found that increasing the concentration of h-mmnbtBuDPhA2Anth improved reliability. This is because increasing the concentration of the guest in the emitting layer increases the excitation energy in the emitting layer. This shows that the guest concentration can be efficiently converted into guest emission. By increasing the Dexter mechanism, the energy transfer from the host to the guest can be suppressed. The triplet excitation energy from the host to the guest via the Förster mechanism is This suggests that the migration speed can be increased. A light-emitting device using the compound can be said to have good luminous efficiency and reliability. . [Example]

[0543] In this example, a light-emitting device was manufactured using a compound according to one embodiment of the present invention, and its operating characteristics were evaluated. The light-emitting devices shown in this example are light-emitting device 7-1 and light-emitting device 7-2. -2, light-emitting device 7-3, light-emitting device 7-4, and light-emitting device 7-5, These light-emitting devices have the element structure shown in FIG. 16 and are the same as the fifth example of the light-emitting layer configuration of the second embodiment. Specifically, it has the configuration shown in Table 13. The compound of the present invention, N,N'-bis{3,5-bis(2-methyl-2-phenylene-1-yl)-2-propanol, contained in the light-emitting layer is (Tricyclo[5.2.1.0 2,6 ]decan-8-yl)phenyl}-N,N'-bis (3,5-di-tert-butylphenyl)-2-phenylanthracene-9,10-di Contains amine (abbreviation: 2Ph-mmTCDtBuDPhA2Anth) (structural formula 120) Although the amounts are different, the other components are the same. The chemical formulas of the materials used in this example are as follows: Shown below.

[0544] [Table 13]

[0545] [ka]

[0546] <Light-emitting device configuration> The light-emitting device shown in this example has the same structure as in Example 10, as shown in FIG. The configuration different from Example 10 is that of the light-emitting device 7-1, the light-emitting device 7-2, and the light-emitting device 7-3. , and 2Ph-mmTCDtBuDPhA2An used in the light-emitting layer of light-emitting device 7-4 th.

[0547] <Operation characteristics of light-emitting devices> The operating characteristics of the fabricated light-emitting device were measured. The luminance, chromaticity (CIE chromaticity), and A spectroradiometer (Topcon, SR-UL1R) was used to measure electroluminescence (EL) spectra. The measurements were carried out at room temperature (an atmosphere maintained at 23°C).

[0548] The light-emitting devices 7-1, 7-2, 7-3, and 7-4 prepared in this example are shown below. As a result of the operating characteristics of the light-emitting device 7-4 and the light-emitting device 7-5, the current density-luminance The luminance vs. current efficiency characteristics are shown in Figure 61, the voltage vs. luminance characteristics in Figure 62, the luminance vs. current efficiency characteristics in Figure 63, and the voltage vs. current density characteristics in Figure 64. The luminance characteristics are shown in FIG. 64, and the luminance-external quantum efficiency characteristics are shown in FIG. 65.

[0549] In addition, each light-emitting device is supplied with 2.5mA / cm 2 The electroluminescence spectrum when a current is passed through the The EL spectrum is shown in Figure 66.

[0550] Next, 1000 cd / m 2 The main initial characteristics of each light-emitting device in the vicinity are shown in Table 14 below. Shown below.

[0551] [Table 14]

[0552] The light emitting devices 7-1 to 7-4 are light emitting devices 7-5 and 7-6, respectively. This is a device that contains the compound 2Ph-mmTCDtBuDPhA2Anth. Figure 66 As shown in Figure 1, the EL spectrum of the light-emitting device 7-5 has a peak wavelength of 522 nm. The green light emitted from the light-emitting device was derived from [Ir(ppy)2(mdppy)]. The EL spectra of the light-emitting devices 7-1 to 7-4 have a peak wavelength around 540 nm. The green luminescence was derived from 2Ph-mmTCDtBuDPhA2Anth. Therefore, in the light-emitting devices 7-1 to 7-4, the fluorescent material 2 Ph-mmTCDtBuDPhA2Anth receives excitation energy and emits light. Furthermore, from the above results, it can be seen that the light-emitting devices 7-1 to 7-5 are It can be seen that all of them exhibit a high external quantum efficiency of 18% or more. The probability of generating singlet excitons generated by recombination of carriers (holes and electrons) is 25% at most. %, so if the light extraction efficiency to the outside is 30%, the external amount of the fluorescent light-emitting device The maximum efficiency is 7.5%. However, the efficiency of the light-emitting devices 7-1 to 7-4 is In this case, the external quantum efficiency is higher than 7.5%. originates from singlet excitons generated by the recombination of injected carriers (holes and electrons) from In addition to the emission from the triplet excitons, the emission from the triplet excitons is more pronounced than that from fluorescent materials. This is because it is possible to

[0553] In addition, the emission layers contained 2P-mmTCDtBuDPhA2Anth at different concentrations. In comparing optical devices 7-1 to 7-5, the external quantum efficiency is similar. Therefore, the compound of one embodiment of the present invention, 2Ph-mmTCDt BuDPhA2Anth is particularly problematic at high concentrations in the emissive layer of light-emitting devices. It was shown that the deactivation of triplet excitation energy can be suppressed, resulting in efficient light emission.

[0554] Furthermore, for the light-emitting devices 7-1 to 7-5, 50 mA / cm 2 In A current density driving test was carried out. The results are shown in Figure 67. From these results, the guest, 2P Increasing the concentration of h-mmTCDtBuDPhA2Anth resulted in better reliability. This is because increasing the concentration of the guest in the emitting layer increases the excitation energy in the emitting layer. This shows that the luminescence of the guest can be efficiently converted into the luminescence of the guest. By increasing the concentration, the energy transfer from the host to the guest due to the Dexter mechanism is suppressed. At the same time, the triplet excitation energy is increased by the Förster mechanism from the host to the guest. Therefore, it is possible to increase the movement speed. Light-emitting devices using compounds can be said to have good luminous efficiency and reliability. do. [Example]

[0555] In this example, a light-emitting device was manufactured using a compound according to one embodiment of the present invention, and its operating characteristics were evaluated. The light-emitting devices shown in this example are light-emitting device 8-1, light-emitting device 8-2, and light-emitting device 8-3. 8-2, light-emitting device 8-3, light-emitting device 8-4, and light-emitting device 8-5; These light-emitting devices have the element structure shown in FIG. 16, and the configuration example of the light-emitting layer of the second embodiment 3, and specifically, the configuration shown in Table 15. The compound of one embodiment of the present invention, N,N'-bis{3,5-bis(3,5-bis)- S(Tricyclo[5.2.1.0 2,6 ]decan-8-yl)phenyl}-N,N'-biphenyl bis(3,5-di-tert-butylphenyl)-2-phenylanthracene-9,10- Diamine (abbreviation: 2Ph-mmTCDtBuDPhA2Anth) (Structural formula 120) The chemical formulas of the materials used in this example are as follows: Shown below.

[0556] [Table 15]

[0557] [ka]

[0558] <Light-emitting device configuration> The light-emitting device shown in this example has the same structure as in Example 12, as shown in FIG. The configuration different from Example 12 is that of the light-emitting device 8-1, the light-emitting device 8-2, and the light-emitting device 8-3. , 3,3 used in the hole transport layer 912 of the light-emitting device 8-4 and the light-emitting device 8-5. '-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), the Tris[2-(1H-pyrazol-1-yl-κN2)phenyl-κC]iridium(II I) (abbreviation: [Ir(ppz)3]), and 9,9'-(pyrimidine-4,6-diyl Di-3,1-phenylene)bis(9H-carbazole) (abbreviation: 4,6mCzP2Pm) The compound used in the electron transport layer 914 is 4,6mCzP2Pm.

[0559] <Operation characteristics of light-emitting devices> The operating characteristics of the fabricated light-emitting device were measured using the same method as in Example 12. Therefore, the explanation will be omitted.

[0560] The light-emitting devices 8-1, 8-2, and 8-3 produced in this example were: As a result of the operating characteristics of the light-emitting device 8-4 and the light-emitting device 8-5, the current density-luminance The luminance vs. current efficiency characteristics are shown in Figure 68, the voltage vs. luminance characteristics in Figure 69, the luminance vs. current efficiency characteristics in Figure 70, and the voltage vs. current density characteristics in Figure 71. The luminance characteristics are shown in FIG. 71, and the luminance-external quantum efficiency characteristics are shown in FIG.

[0561] In addition, each light-emitting device is supplied with 2.5mA / cm 2 The electroluminescence spectrum when a current is passed through the The EL spectrum is shown in Figure 73.

[0562] Next, 1000 cd / m 2 The main initial characteristics of each light-emitting device in the vicinity are shown in Table 16 below. Shown below.

[0563] [Table 16]

[0564] The light emitting devices 8-1 to 8-4 are light emitting devices 8-5 and 8-6, respectively. This is a device that contains the compound 2Ph-mmTCDtBuDPhA2Anth. Figure 73 As shown in Figure 1, the EL spectrum of the light-emitting device 8-5 has a peak wavelength of 531 nm. , 4,6mCzP2Pm and [Ir(ppz)3] exhibit different emission spectra. The green emission is due to the exciplex of 4,6mCzP2Pm and [Ir(ppz)3]. The EL spectra of the light-emitting devices 8-1 to 8-4 have a peak wavelength The green light from 2Ph-mmTCDtBuDPhA2Anth is around 540 nm. From this, it can be seen that in the light-emitting devices 8-1 to 8-4, The fluorescent substance 2Ph-mmTCDtBuDPhA2Anth receives the excitation energy. Furthermore, from the above results, it can be seen that light is emitted from the light-emitting device 8-1. It can be seen that Device 8-5 exhibits a high external quantum efficiency of 19% or more. Singlet excitons generated by recombination of carriers (holes and electrons) injected from electrodes Since the generation probability is at most 25%, if the light extraction efficiency to the outside is 30%, The external quantum efficiency of the light-emitting device is 7.5% at maximum. Therefore, in the light-emitting device 8-4, the external quantum efficiency was higher than 7.5%. This is generated by the recombination of carriers (holes and electrons) injected from a pair of electrodes. In addition to the emission from singlet excitons, the emission from triplet excitons Emission or singlet excitation generated from triplet excitons by reverse intersystem crossing in exciplexes This is because the light emitted from the molecule is obtained from a fluorescent substance.

[0565] In addition, the emission layers contained 2P-mmTCDtBuDPhA2Anth at different concentrations. In comparing optical devices 8-1 to 8-5, they all have similar external quantum efficiencies. Therefore, the compound of one embodiment of the present invention, 2Ph-mmTCDt BuDPhA2Anth is particularly problematic at high concentrations in the emissive layer of light-emitting devices. It was shown that the deactivation of triplet excitation energy can be suppressed, resulting in efficient light emission.

[0566] Furthermore, for the light-emitting devices 8-1 to 8-5, 50 mA / cm 2 In A current density driving test was carried out. The results are shown in Figure 74. From these results, the guest, 2P Increasing the concentration of h-mmTCDtBuDPhA2Anth resulted in better reliability. This is because increasing the concentration of the guest in the emitting layer increases the excitation energy in the emitting layer. This shows that the luminescence of the guest can be efficiently converted into the luminescence of the guest. By increasing the concentration, the energy transfer from the host to the guest due to the Dexter mechanism is suppressed. At the same time, the triplet excitation energy is increased by the Förster mechanism from the host to the guest. Therefore, it is possible to increase the movement speed. Light-emitting devices using compounds can be said to have good luminous efficiency and reliability. do. [Explanation of symbols]

[0567] 101 first electrode 102 second electrode 103 EL layer 103a, 103b EL layer 104 Charge generation layer 111, 111a, 111b hole injection layer 112, 112a, 112b hole transport layer 113, 113a, 113b Light-emitting layer 114, 114a, 114b electron transport layer 115, 115a, 115b electron injection layer 121 The first organic compound 122 Second organic compound 123 The third organic compound 124 Fluorescent Materials 130a, 130b luminophores 131 Protecting groups 200R, 200G, 200B optical distance 201 First substrate 202 Transistor (FET) 203R, 203G, 203B, 203W Light-Emitting Devices 204 EL layer 205 Second substrate 206R, 206G, 206B color filters 206R', 206G', 206B' color filters 207 First electrode 208 Second electrode 209 Black layer (black matrix) 210R, 210G conductive layer 301 First substrate 302 Pixel section 303 Driver circuit section (source line driver circuit) 304a, 304b Drive circuit section (gate line drive circuit) 305 Sealing material 306 Second substrate 307 Wiring 308 FPC 309 FET 310 FET 311 FET 312 FET 313 First electrode 314 Insulators 315 EL layer 316 Second electrode 317 Light-emitting devices 318 Space 900 boards 901 First electrode 902 EL layer 903 Second electrode 911 Hole injection layer 912 Hole transport layer 913 Light-emitting layer 914 Electron transport layer 915 Electron injection layer 4000 lighting equipment 4001 board 4002 Light-emitting devices 4003 board 4004 First electrode 4005 EL layer 4006 Second electrode 4007 Electrode 4008 Electrode 4009 Auxiliary wiring 4010 Insulation layer 4011 Sealing substrate 4012 Sealing material 4013 Desiccant 4015 Diffuser 4200 Lighting Equipment 4201 Circuit Board 4202 Light-emitting devices 4204 First electrode 4205 EL layer 4206 Second electrode 4207 Electrode 4208 Electrode 4209 Auxiliary wiring 4210 Insulation layer 4211 Sealing substrate 4212 Sealing material 4213 Barrier film 4214 Planarization film 4215 Diffuser 5101 Light 5102 Wheels 5103 Door 5104 Display section 5105 Handle 5106 Shift lever 5107 Seat 5108 Inner rearview mirror 5109 Windshield 7000 chassis 7001 Display section 7002 2nd display section 7003 Speaker 7004 LED lamp 7005 Operation key 7006 Connection terminal 7007 Sensor 7008 Microphone 7009 Switch 7010 Infrared port 7011 Recording medium reading unit 7012 Support part 7013 Earphones 7014 Antenna 7015 Shutter button 7016 Image receiving unit 7018 Stand 7020 Camera 7021 External connection part 7022, 7023 Operation buttons 7024 Connection terminal 7025 band 7026 Microphone 7029 Sensor 7030 Speaker 7052, 7053, 7054 Information 9310 Mobile Information Terminal 9311 Display section 9312 Display area 9313 Hinge 9315 chassis

Claims

1. A compound represented by any one of structural formula (100), structural formula (102), structural formula (108), structural formula (116), and structural formula (120). 【Chemistry 1】 【Chemistry 2】

2. A light-emitting device using the compound according to claim 1.

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