Organic compounds and light-emitting / receiving devices

Abstract

To provide a novel organic compound excellent in convenience, usefulness or reliability.SOLUTION: The invention provides an organic compound represented by general formula (G1). Here, A1 represents one of hydrogen, deuterium, a C1-13 alkyl group, a C3-10 cycloalkyl group, a C6-25 aryl group, a C2-25 heteroaryl group, and a diarylamino group; Ar1 to Ar4 each independently represent one of a C6-25 aryl group, a C2-25 heteroaryl group, and a diarylamino group; and R1 to R6 each independently represent one of hydrogen, deuterium, a C1-13 alkyl group, a C3-10 cycloalkyl group, a C6-25 aryl group, a C2-25 heteroaryl group, and a C1-13 alkoxy group.SELECTED DRAWING: None

Description

[Technical Field]

[0001] One aspect of the present invention relates to an organic compound, a light-receiving device, a light-receiving device, an electronic device, or a semiconductor device.

[0002] Furthermore, one aspect of the present invention is not limited to the above-mentioned technical field. The technical field of one aspect of the invention disclosed herein relates to a product, a method, or a method of manufacture. Alternatively, one aspect of the present invention relates to a process, a machine, a manufacture, or a composition of matter. More specifically, examples of the technical fields of one aspect of the present invention disclosed herein include organic compounds, semiconductor devices, display devices, light-emitting devices, energy storage devices, memory devices, methods for driving them, or methods for manufacturing them. [Background technology]

[0003] Practical applications of photodetectors using organic compounds as photoelectric conversion elements are progressing. The basic structure of these photoelectric conversion elements is an organic compound layer (active layer) containing a photoelectric conversion material sandwiched between a pair of electrodes. This element absorbs light energy and generates carriers, thereby obtaining electrons from the photoelectric conversion material.

[0004] For example, a functional panel is known in which pixels provided in a display area are equipped with light-emitting elements and photoelectric conversion elements (Patent Document 1). For example, a functional panel having a first drive circuit, a second drive circuit, and an area, wherein the first drive circuit supplies a first selection signal, the second drive circuit supplies a second selection signal and a third selection signal, and the area comprises pixels. Each pixel comprises a first pixel circuit, a light-emitting element, a second pixel circuit, and a photoelectric conversion element. The first pixel circuit is supplied with a first selection signal, the first pixel circuit acquires an image signal based on the first selection signal, the light-emitting element is electrically connected to the first pixel circuit, and the light-emitting element emits light based on the image signal. Furthermore, the second pixel circuit is supplied with a second selection signal and a third selection signal during periods when the first selection signal is not supplied, the second pixel circuit acquires an imaging signal based on the second selection signal, and supplies an imaging signal based on the third selection signal, the photoelectric conversion element is electrically connected to the second pixel circuit, and the photoelectric conversion element generates an imaging signal. [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] WO2020 / 152556 [Overview of the project] [Problems that the invention aims to solve]

[0006] One aspect of the present invention aims to provide a novel light-receiving device that is superior in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel light-emitting and light-receiving device that is superior in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel electronic device that is superior in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel light-receiving device, a novel light-emitting and light-receiving device, or a novel electronic device.

[0007] Furthermore, the description of these problems does not preclude the existence of other problems. Moreover, one aspect of the present invention does not need to solve all of these problems. Other problems will naturally become apparent from the description in the specification, drawings, and claims, and it is possible to extract other problems from the description in the specification, drawings, and claims. [Means for solving the problem]

[0008] (1) One aspect of the present invention is an organic compound represented by the following general formula (G1).

[0009] [ka]

[0010] In the above general formula (G1), A 1 This represents one of the following: hydrogen, deuterium, a substituted or unsubstituted C1 to C13 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C25 aryl group, a substituted or unsubstituted C2 to C25 heteroaryl group, or a substituted or unsubstituted diarylamino group. Also, Ar 1 ~Ar 4 Each of these independently represents one of the following: a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, or a substituted or unsubstituted diarylamino group. However, A 1 or Ar 1 ~Ar 4 The two aryl groups of the substituted or unsubstituted diarylamino group are each independently either a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms. Furthermore, the two aryl groups may be bonded to each other to form a ring. Also, R 1 ~R 6represents, independently of each other, any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 13 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, and a substituted or unsubstituted alkoxy group having 1 to 13 carbon atoms, and all hydrogens in the general formula (G1) may be deuterium.

[0011] (2) One aspect of the present invention is an organic compound represented by the general formula (G2).

[0012]

Chemical formula

[0013] In the general formula (G2) above, A 1 represents any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 13 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, or a substituted or unsubstituted diarylamino group. Also, Ar 1 to Ar 3 each independently represents any one of a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, or a substituted or unsubstituted diarylamino group. However, the two aryl groups of the substituted or unsubstituted diarylamino group of A 1 or Ar 1 to Ar 3 are each independently either a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms. Also, the two aryl groups may be bonded to each other to form a ring. Also, Ar 5 represents any one of a substituted or unsubstituted arylene group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 25 carbon atoms. Also, n represents an integer from 0 to 2. Also, Ar6 or Ar 7 Each of these independently represents either a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms. Also, Ar 6 and Ar 7 These may be joined together to form a ring. Also, if n is 1, Ar 5 and Ar 6 And, Ar 5 and Ar 7 These may be joined together to form a ring. Also, if n is 2, Ar 5 Among the groups contained in, Ar via N 6 and adjacent bases, or via N, Ar 7 The adjacent base and the Ar 6 or Ar 7 They may bond with each other to form a ring. Also, R 1 ~R 6 Each of these independently represents one of the following: hydrogen, deuterium, a substituted or unsubstituted C1 to C13 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C25 aryl group, a substituted or unsubstituted C2 to C25 heteroaryl group, or a substituted or unsubstituted C1 to C13 alkoxy group, and all hydrogens in general formula (G2) may be deuterium.

[0014] (3) One aspect of the present invention is an organic compound represented by the general formula (G3).

[0015] [ka]

[0016] In the above general formula (G3), Ar 1 ~Ar 3 Each of these independently represents one of the following: a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, or a substituted or unsubstituted diarylamino group. However, Ar 1 ~Ar 3The two aryl groups of the substituted or unsubstituted diarylamino group are each independently either a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms. Furthermore, the two aryl groups may be bonded to each other to form a ring. Also, Ar 5 represents either a substituted or unsubstituted arylene group with 6 to 25 carbon atoms, or a substituted or unsubstituted heteroarylene group with 2 to 25 carbon atoms. Also, n represents an integer from 0 to 2. Furthermore, Ar 6 or Ar 7 Each of these independently represents either a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms. Also, Ar 6 and Ar 7 These may be joined together to form a ring. Also, if n is 1, Ar 5 and Ar 6 And, Ar 5 and Ar 7 These may be joined together to form a ring. Also, if n is 2, Ar 5 Among the groups contained in, Ar via N 6 and adjacent bases, or via N, Ar 7 The adjacent base and the Ar 6 or Ar 7 They may bond with each other to form a ring. Also, R 1 ~R 6 and R 20 ~R 24 Each of these independently represents one of the following: hydrogen, deuterium, a substituted or unsubstituted C1 to C13 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C25 aryl group, a substituted or unsubstituted C2 to C25 heteroaryl group, or a substituted or unsubstituted C1 to C13 alkoxy group, and all hydrogens in general formula (G3) may be deuterium.

[0017] (4) One aspect of the present invention is an organic compound represented by the general formula (G4).

[0018] [ka]

[0019] In the above general formula (G4), Ar 1 ~Ar 3 Ar 8 , and Ar 9 Each of these independently represents one of the following: a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, or a substituted or unsubstituted diarylamino group. However, Ar 1 ~Ar 3 Ar 8 , and Ar 9 The two aryl groups of the substituted or unsubstituted diarylamino group are each independently either a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms. Furthermore, the two aryl groups may be bonded to each other to form a ring. Also, Ar 5 represents either a substituted or unsubstituted arylene group with 6 to 25 carbon atoms, or a substituted or unsubstituted heteroarylene group with 2 to 25 carbon atoms. Also, n represents an integer from 0 to 2. Furthermore, Ar 6 or Ar 7 Each of these independently represents either a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms. Also, Ar 6 and Ar 7 These may be joined together to form a ring. Also, if n is 1, Ar 5 and Ar 6 And, Ar 5 and Ar 7 These may be joined together to form a ring. Also, if n is 2, Ar 5 Among the groups contained in, Ar via N 6 and adjacent bases, or via N, Ar 7 The adjacent base and the Ar 6 or Ar 7They may bond with each other to form a ring. Also, R 1 ~R 6 and R 20 ~R 24 Each of these independently represents one of the following: hydrogen, deuterium, a substituted or unsubstituted C1 to C13 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C25 aryl group, a substituted or unsubstituted C2 to C25 heteroaryl group, or a substituted or unsubstituted C1 to C13 alkoxy group, and all hydrogens in general formula (G4) may be deuterium.

[0020] (5) One aspect of the present invention is an organic compound represented by the general formula (G5).

[0021] [ka]

[0022] In the above general formula (G5), A 1 This represents one of the following: hydrogen, deuterium, a substituted or unsubstituted C1 to C13 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C25 aryl group, a substituted or unsubstituted C2 to C25 heteroaryl group, or a substituted or unsubstituted diarylamino group. Also, Ar 1 ~Ar 3 Each of these independently represents one of the following: a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, or a substituted or unsubstituted diarylamino group. However, A 1 or Ar 1 ~Ar 3 The two aryl groups of the substituted or unsubstituted diarylamino group are each independently either a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms. Furthermore, the two aryl groups may be bonded to each other to form a ring. Also, Ar 10represents any one of a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 13 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms. Also, R 1 to R 14 each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 13 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 13 carbon atoms, and all hydrogens in general formula (G5) may be deuterium.

[0023] (6) One aspect of the present invention is an organic compound represented by general formula (G6).

[0024] <000057�>

Chemical formula

[0025] In the above general formula (G6), R 1 to R 14 , and R 20 to R 44 each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 13 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 13 carbon atoms.

[0026] In the drawings attached to this specification, the components are classified by function and shown as block diagrams with independent blocks for each. However, in actuality, it is difficult to completely separate the components by function, and one component may be related to multiple functions.

Advantages of the Invention

[0027] According to one aspect of the present invention, a novel organic compound with superior convenience, usefulness, or reliability can be provided. According to one aspect of the present invention, a novel light-receiving device with superior convenience, usefulness, or reliability can be provided. Alternatively, a novel light-emitting device with superior convenience, usefulness, or reliability can be provided. Alternatively, a novel electronic device with superior convenience, usefulness, or reliability can be provided. Alternatively, a novel light-receiving device, a novel light-emitting device, or a novel electronic device can be provided.

[0028] Furthermore, the description of these effects does not preclude the existence of other effects. Moreover, one aspect of the present invention does not necessarily have to possess all of these effects. Other effects will naturally become apparent from the description in the specification, drawings, and claims, and it is possible to extract other effects from the description in the specification, drawings, and claims. [Brief explanation of the drawing]

[0029] [Figure 1] Figures 1(A) to 1(C) illustrate a light-receiving device according to one embodiment of the present invention. [Figure 2] Figures 2(A) to 2(C) illustrate a light-receiving and light-emitting device according to one embodiment of the present invention. [Figure 3] Figures 3(A) and 3(B) illustrate a display device according to one embodiment of the present invention. [Figure 4] Figures 4(A) to 4(E) illustrate the configuration of a light-emitting device according to an embodiment. [Figure 5] Figures 5(A) to 5(D) illustrate an embodiment of a light-receiving and light-emitting device. [Figure 6] Figures 6(A) to 6(C) illustrate a method for manufacturing a light-receiving device according to an embodiment. [Figure 7] Figures 7(A) to 7(C) illustrate a method for manufacturing a light-receiving device according to an embodiment. [Figure 8]Figures 8(A) to 8(C) illustrate a method for manufacturing a light-receiving device according to an embodiment. [Figure 9] Figures 9(A) to 9(D) illustrate a method for manufacturing a light-receiving device according to an embodiment. [Figure 10] Figures 10(A) to 10(E) illustrate a method for manufacturing a light-receiving device according to an embodiment. [Figure 11] Figures 11(A) to 11(F) illustrate the light-receiving device and pixel arrangement according to the embodiment. [Figure 12] Figures 12(A) to 12(C) illustrate the pixel circuit according to the embodiment. [Figure 13] Figure 13 is a diagram illustrating a light-receiving device according to an embodiment. [Figure 14] Figures 14(A) to 14(E) illustrate the electronic device according to the embodiment. [Figure 15] Figures 15(A) to 15(E) illustrate the electronic device according to the embodiment. [Figure 16] Figures 16(A) and 16(B) illustrate the electronic device according to the embodiment. [Figure 17] Figures 17(A) and 17(B) show the 1H NMR spectra of the organic compounds in the examples. [Figure 18] Figure 18 shows the absorption and emission spectra of the organic compounds in toluene solutions according to the examples. [Figure 19] Figures 19(A) and (B) show the 1H NMR spectra of the organic compounds in the examples. [Figure 20] Figures 20(A) and (B) show the 1H NMR spectra of the organic compounds in the examples. [Figure 21] Figure 21 shows the absorption and emission spectra of the organic compounds in toluene solutions according to the examples. [Figure 22] Figure 22 is a diagram illustrating a device according to an embodiment. [Figure 23] Figures 23(A) and (B) illustrate the voltage-current characteristics of the photodetector according to the embodiment. [Figure 24] Figure 24 illustrates the incident light wavelength-external quantum efficiency characteristics of the light-receiving device according to the embodiment. [Modes for carrying out the invention]

[0030] Embodiments will be described in detail with reference to the drawings. However, it will be readily apparent to those skilled in the art that the present invention is not limited to the following description, and that its form and details can be modified in various ways without departing from the spirit and scope of the present invention. Accordingly, the present invention is not to be interpreted as being limited to the contents of the embodiments shown below. In the configuration of the invention described below, the same reference numerals are used in common across different drawings for the same parts or parts having similar functions, and repeated descriptions are omitted.

[0031] (Embodiment 1) This embodiment describes an organic compound according to one aspect of the present invention.

[0032] <Example 1 of an organic compound> The organic compound described in this embodiment is an organic compound represented by the following general formula (G1).

[0033] [ka]

[0034] However, in the above general formula (G1), A 1 This is one of the following: hydrogen, deuterium, a substituted or unsubstituted C1 to C13 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C25 aryl group, a substituted or unsubstituted C2 to C25 heteroaryl group, or a substituted or unsubstituted diarylamino group.

[0035] Furthermore, in the above general formula (G1), Ar1 up to Ar 4 is each independently either a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, or a substituted or unsubstituted diarylamino group.

[0036] In the above general formula (G1), A 1 or Ar 1 up to Ar 4 The two aryl groups of the substituted or unsubstituted diarylamino group of are each independently either a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms. Further, the two aryl groups may be bonded to each other to form a ring.

[0037] Also, in the above general formula (G1), R 1 up to R 6 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 13 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 13 carbon atoms.

[0038] All hydrogens in the above general formula (G1) may be deuterium.

[0039] Also, in the above general formula (G1), A 1 or Ar 1 up to Ar 4 Examples of the diarylamino group substituting A or Ar up to Ar include a diphenylamino group, a di(1-naphthyl)amino group, etc., and a substituted arylamino group such as a bis(m-tolyl)amino group may also be used.

[0040] In the above general formula (G1), A 1 or Ar 1 up to Ar 4Examples of the two aryl groups that a substituted or unsubstituted diarylamino group may have are a phenyl group, naphthyl group, acenaphthyrenyl group, anthryl group, phenanthryl group, biphenyl group, terphenyl group, triphenylenyl group, 9,9-dimethyl-9H-fluorenyl group, 9,9-diphenyl-9H-fluorenyl group, spirofluorenyl group, etc. Examples of heteroaryl groups include a carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, benzonaphthofuranyl group, benzonaphthothiophenyl group, indrocarbazolyl group, benzoflocarbazolyl group, benzothienocarbazolyl group, indenocarbazolyl group, dibenzocarbazolyl group, (9-phenyl-9H-carbazolyl)phenyl group, (9H-carbazole-9-yl)phenyl group, 9-phenyl-9H-carbazolyl group, etc.

[0041] Furthermore, in the above general formula (G1), A 1 Ar 1 ~Ar 4 , or R 1 ~R 6 Examples of heteroaryl groups that can be substituted include carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, indolocarbazolyl, benzoflocarbazolyl, benzothienocarbazolyl, indenocarbazolyl, dibenzocarbazolyl, (9-phenyl-9H-carbazolyl)phenyl, (9H-carbazole-9-yl)phenyl, and 9-phenyl-9H-carbazolyl. In particular, 3-(9-phenyl-9H-carbazolyl)phenyl, 4-(9H-carbazole-9-yl)phenyl, and 9-phenyl-9H-carbazole-3-yl groups are considered preferred substituents because the starting materials are readily available and the synthesis is simple.

[0042] Furthermore, in the above general formula (G1), A 1 Ar 1 ~Ar 4 , or R 1 ~R 6Examples of aryl groups that can be substituted include phenyl, naphthyl, acenaphthyrenyl, anthryl, phenanthryl, biphenyl, terphenyl, triphenylenyl, 9,9-dimethyl-9H-fluorenyl, 9,9-diphenyl-9H-fluorenyl, and spirofluorenyl groups. In particular, 1-naphthyl, 2-naphthyl, orthobiphenyl, metabiphenyl, and parabiphenyl groups are considered preferred substituents because the starting materials are readily available and the synthesis is simple.

[0043] Furthermore, in the above general formula (G1), A 1 , or R 1 ~R 6 Examples of alkyl groups that can be substituted include propyl group, isopropyl group, butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, octyl group, decyl group, 2-ethylhexyl group, pentan-3-yl group, heptan-4-yl group, and the like.

[0044] Furthermore, in the above general formula (G1), A 1 , or R 1 ~R 6 Examples of cycloalkyl groups to be substituted include cyclopropyl, cyclopentyl, cyclohexyl, adamantyl, bicyclo[2.2.1]heptyl, and tricyclo[5.2.1.0 2,6 Examples include decanyl groups and noadamantyl groups.

[0045] Furthermore, in the above general formula (G1), R 1 ~R 6 Examples of alkoxy groups that can be substituted include methoxy, ethoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, decyloxy, lauryloxy, 2-ethylhexyloxy, 3-methylbutoxy, and isopropyloxy groups.

[0046] In addition, in the above general formula (G1), A 1 Ar1 ~Ar 4 , or R 1 ~R 6 Any of the substituents described above that are substituted may have other substituents. Examples of other substituents include the alkyl groups, cycloalkyl groups, trialkylsilyl groups, aryl groups, or deuterium.

[0047] The organic compound of the present invention can be an organic compound that absorbs light in a broad wavelength range, including the visible light region. This makes it suitable for use, for example, in the active layer of a photodetector. Furthermore, it is suitable for use, for example, in a layer in contact with the active layer of a photodetector.

[0048] Furthermore, by using the above-mentioned organic compound in a photodetector, heat resistance can be increased without impairing the photodetector's characteristics. In addition, degradation of the organic compound can be suppressed during the manufacturing process of the photodetector, such as during heating processes like vacuum deposition. Degradation associated with the operation of the photodetector can also be suppressed. As a result, a novel organic compound with superior convenience, usefulness, and reliability can be provided. Furthermore, a highly efficient photoelectric conversion device can be provided. Additionally, a photoelectric conversion device capable of operating at low voltages can be provided.

[0049] Furthermore, the above-mentioned organic compound can provide a device capable of receiving light in a wide wavelength range, including the visible light region. It can also provide a photodetector that can operate even at low voltages. In addition, the organic compound of the present invention has excellent solubility, allowing for high purity and providing a highly reliable photodetector. Moreover, since the organic compound of the present invention can be synthesized by various methods, flexible molecular design is possible. Furthermore, the organic compound of the present invention has a shallow HOMO (Highest Occupied Molecular Orbital) level derived from the amine skeleton and simultaneously possesses the excellent carrier transport properties of anthracene, thus enabling the provision of a highly efficient device.

[0050] <Example of an organic compound 2> Furthermore, the organic compound described in this embodiment is an organic compound represented by the following general formula (G2).

[0051] [ka]

[0052] However, in the above general formula (G2), Ar 5 n is either a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 25 carbon atoms. n represents an integer from 0 to 2.

[0053] Furthermore, in the above general formula (G2), Ar 6 or Ar 7 Each of these is independently either a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms.

[0054] Furthermore, in the above general formula (G2), Ar 6 and Ar 7 These may be joined together to form a ring. Also, if n is 1, Ar 5 and Ar 6 And, Ar 5 and Ar 7 These may be joined together to form a ring. Also, if n is 2, Ar 5 Among the groups contained in, Ar via N 6 and adjacent bases, or via N, Ar 7 The adjacent base and the Ar 6 or Ar 7 They may also bond with each other to form a ring.

[0055] Note that all hydrogen atoms in the above general formula (G2) may be deuterium.

[0056] In addition, in the above general formula (G2), A 1 Ar 1 ~Ar4 , or R 1 ~R 6 The substituents to be substituted can refer to substituents that can be used for the same symbol in the general formula (G1) described in <Example 1 of Organic Compounds> above.

[0057] Furthermore, in the above general formula (G2), Ar 6 , or Ar 7 Examples of heteroaryl groups that can be substituted include carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, benzonaphthofuranyl group, benzonaphthothiophenyl group, indolocarbazolyl group, benzoflocarbazolyl group, benzothienocarbazolyl group, indenocarbazolyl group, dibenzocarbazolyl group, (9-phenyl-9H-carbazolyl)phenyl group, (9H-carbazole-9-yl)phenyl group, and 9-phenyl-9H-carbazolyl group.

[0058] Furthermore, in the above general formula (G2), Ar 6 , or Ar 7 Examples of aryl groups that can be substituted include phenyl, naphthyl, acenaphthyrenyl, anthryl, phenanthryl, biphenyl, terphenyl, triphenylenyl, 9,9-dimethyl-9H-fluorenyl, 9,9-diphenyl-9H-fluorenyl, and spirofluorenyl groups. In particular, 1-naphthyl, 2-naphthyl, orthobiphenyl, metabiphenyl, and parabiphenyl groups are considered preferred substituents because the starting materials are readily available and the synthesis is simple.

[0059] Furthermore, in the above general formula (G2), Ar 5Examples of arylene groups that can be substituted include phenylene group, toluene group, dimethylphenylene group, trimethylphenylene group, tetramethylphenylene group, biphenylene group, terphenylene group, quaterphenylene group, naphthylene group, fluorenylene group, 9,9-dimethylfluorenylene group, 9,9-diphenylfluorenylene group, spiro-9,9'-bifluorenylene group, 9,10-dihydrophenantrenylene group, phenantrenylene group, triphenylenylene group, benzo[a]phenantrenylene group, and benzo[c]phenantrenylene group.

[0060] Furthermore, in the above general formula (G2), Ar 5 Examples of heteroarylene groups to be substituted include substituted or unsubstituted thiophene-diyl groups and substituted or unsubstituted furan-diyl groups.

[0061] In addition, in the above general formula (G2), A 1 Ar 1 ~Ar 3 Ar 5 ~Ar 7 , R 1 ~R 6 Any of the substituents described above that are substituted may have other substituents. Examples of other substituents include the alkyl groups, cycloalkyl groups, trialkylsilyl groups, aryl groups, or deuterium.

[0062] This allows for the creation of organic compounds that absorb light across a wide wavelength range, including the visible light region, making them suitable for use, for example, in the active layer of a photodetector. Furthermore, they are suitable for use in layers in contact with the active layer of a photodetector.

[0063] Furthermore, by using the above-mentioned organic compound in a photodetector, heat resistance can be increased without impairing the photodetector's characteristics. In addition, degradation of the organic compound can be suppressed during the manufacturing process of the photodetector, such as during heating processes like vacuum deposition. Degradation associated with the operation of the photodetector can also be suppressed. As a result, a novel organic compound with superior convenience, usefulness, and reliability can be provided. Furthermore, a highly efficient photoelectric conversion device can be provided. Additionally, a photoelectric conversion device capable of operating at low voltages can be provided.

[0064] <Example 3 of organic compounds> Furthermore, the organic compound described in this embodiment is an organic compound represented by the following general formula (G3).

[0065] [ka]

[0066] However, in the above general formula (G3), R 20 ~R 24 Each of these is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C13 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C25 aryl group, a substituted or unsubstituted C2 to C25 heteroaryl group, or a substituted or unsubstituted C1 to C13 alkoxy group.

[0067] Furthermore, all hydrogen atoms in general formula (G3) may be deuterium.

[0068] In addition, in the above general formula (G3), Ar 1 ~Ar 3 Ar 5 ~Ar 7 , R 1 ~R 6The substituents to be substituted can refer to substituents that can be used for the same symbols in the general formula (G1) described in <Example 1 of Organic Compounds> and the general formula (G2) described in <Example 2 of Organic Compounds>.

[0069] Furthermore, in the above general formula (G3), R 20 ~R 24 Examples of alkyl groups that can be substituted include propyl group, butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, octyl group, decyl group, 2-ethylhexyl group, pentan-3-yl group, heptan-4-yl group, and the like.

[0070] Furthermore, in the above general formula (G3), R 20 ~R 24 Examples of cycloalkyl groups to be substituted include cyclopropyl, cyclopentyl, cyclohexyl, adamantyl, bicyclo[2.2.1]heptyl, and tricyclo[5.2.1.0 2,6 Examples include decanyl groups and noadamantyl groups.

[0071] Furthermore, in the above general formula (G3), R 20 ~R 24 Examples of aryl groups that can be substituted include phenyl, naphthyl, acenaphthyrenyl, anthryl, phenanthryl, biphenyl, triphenylenyl, fluorenyl, and spirofluorenyl groups. In particular, 1-naphthyl, 2-naphthyl, orthobiphenyl, metabiphenyl, and parabiphenyl groups are considered preferred substituents because the starting materials are readily available and the synthesis is simple.

[0072] Furthermore, in the above general formula (G3), R 20 ~R 24Examples of heteroaryl groups that can be substituted include carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, benzonaphthofuranyl group, benzonaphthothiophenyl group, indolocarbazolyl group, benzoflocarbazolyl group, benzothienocarbazolyl group, indenocarbazolyl group, dibenzocarbazolyl group, and 9-phenyl-9H-carbazolyl group.

[0073] Furthermore, in the above general formula (G3), R 20 ~R 24 Examples of alkoxy groups that can be substituted include methoxy, ethoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, decyloxy, lauryloxy, 2-ethylhexyloxy, 3-methylbutoxy, and isopropyloxy groups.

[0074] In addition, in the above general formula (G3), A 1 Ar 1 ~Ar 3 Ar 5 ~Ar 7 , R 1 ~R 6 or R 20 ~R 24 The substituents to be substituted may each have other substituents. Examples of other substituents include the alkyl groups, cycloalkyl groups, trialkylsilyl groups, aryl groups, or deuterium.

[0075] This allows for the creation of organic compounds that absorb light, particularly in the green region of the visible light spectrum, making them suitable for use, for example, in the active layer of a photodetector that receives green light. They are also suitable for use in layers in contact with the active layer of a photodetector.

[0076] Furthermore, by using the above-mentioned organic compound in a photodetector, heat resistance can be increased without impairing the photodetector's characteristics. In addition, degradation of the organic compound can be suppressed during the manufacturing process of the photodetector, such as during heating processes like vacuum deposition. Degradation associated with the operation of the photodetector can also be suppressed. As a result, a novel organic compound with superior convenience, usefulness, and reliability can be provided. Furthermore, a highly efficient photoelectric conversion device can be provided. Additionally, a photoelectric conversion device capable of operating at low voltages can be provided.

[0077] <Example 4 of organic compounds> Furthermore, the organic compound described in this embodiment is an organic compound represented by the following general formula (G4).

[0078] [ka]

[0079] However, in the above general formula (G4), Ar 8 , and Ar 9 Each of these is independently one of the following: a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, or a substituted or unsubstituted diarylamino group.

[0080] In addition, in the above general formula (G4), Ar 8 , and Ar 9 The two aryl groups of the substituted or unsubstituted diarylamino group are, independently, either substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 25 carbon atoms. Furthermore, the two aryl groups may be bonded to each other to form a ring.

[0081] In addition, in the above general formula (G4), Ar 1 ~Ar 3 Ar 5 ~Ar 7 , R 1~R 6 The substituents to be substituted can refer to substituents that can be used for the same symbols in the general formula (G1) described in <Example 1 of Organic Compounds> and the general formula (G2) described in <Example 2 of Organic Compounds>.

[0082] Furthermore, in the above general formula (G4), Ar 8 , and Ar 9 Examples of aryl groups that can be substituted include phenyl, naphthyl, acenaphthyrenyl, anthryl, phenanthryl, biphenyl, triphenylenyl, fluorenyl, and spirofluorenyl groups. In particular, 1-naphthyl, 2-naphthyl, orthobiphenyl, metabiphenyl, and parabiphenyl groups are considered preferred substituents because the starting materials are readily available and the synthesis is simple.

[0083] Furthermore, in the above general formula (G4), Ar 8 , and Ar 9 Examples of heteroaryl groups that can be substituted include carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, indolocarbazolyl, benzoflocarbazolyl, benzothienocarbazolyl, indenocarbazolyl, dibenzocarbazolyl, (9-phenyl-9H-carbazolyl)phenyl, (9H-carbazole-9-yl)phenyl, and 9-phenyl-9H-carbazolyl. In particular, 3-(9-phenyl-9H-carbazolyl)phenyl, 4-(9H-carbazole-9-yl)phenyl, and 9-phenyl-9H-carbazole-3-yl groups are considered preferred substituents because the starting materials are readily available and the synthesis is simple.

[0084] Furthermore, in the above general formula (G4), Ar 8 , and Ar 9 Examples of diarylamino groups that can be substituted include diphenylamino group, di(1-naphthyl)amino group, and other substituted arylamino groups such as bis(methatryl)amino group.

[0085] In addition, in the above general formula (G4), Ar 8 , and Ar 9 Examples of the two aryl groups that a substituted or unsubstituted diarylamino group may have are a phenyl group, naphthyl group, acenaphthyrenyl group, anthryl group, phenanthryl group, biphenyl group, terphenyl group, triphenylenyl group, 9,9-dimethyl-9H-fluorenyl group, 9,9-diphenyl-9H-fluorenyl group, spirofluorenyl group, etc. Examples of heteroaryl groups include a carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, benzonaphthofuranyl group, benzonaphthothiophenyl group, indrocarbazolyl group, benzoflocarbazolyl group, benzothienocarbazolyl group, indenocarbazolyl group, dibenzocarbazolyl group, (9-phenyl-9H-carbazolyl)phenyl group, (9H-carbazole-9-yl)phenyl group, 9-phenyl-9H-carbazolyl group, etc.

[0086] In addition, in the above general formula (G4), Ar 1 ~Ar 3 Ar 5 ~Ar 7 , R 1 ~R 6 The substituents to be substituted may each have other substituents. Examples of other substituents include the alkyl groups, cycloalkyl groups, trialkylsilyl groups, aryl groups, or deuterium.

[0087] This allows for the creation of organic compounds that absorb light, particularly in the green to red region of visible light, making them suitable for use, for example, in the active layer of a photodetector that receives green to red light. They are also suitable for use in layers in contact with the active layer of a photodetector.

[0088] Furthermore, by using the above-mentioned organic compound in a photodetector, heat resistance can be increased without impairing the photodetector's characteristics. In addition, degradation of the organic compound can be suppressed during the manufacturing process of the photodetector, such as during heating processes like vacuum deposition. Degradation associated with the operation of the photodetector can also be suppressed. As a result, a novel organic compound with superior convenience, usefulness, and reliability can be provided. Furthermore, a highly efficient photoelectric conversion device can be provided. Additionally, a photoelectric conversion device capable of operating at low voltages can be provided.

[0089] <Example 5 of organic compounds> Furthermore, the organic compound described in this embodiment is an organic compound represented by the following general formula (G5).

[0090] [ka]

[0091] However, in the above general formula (G5), Ar 10 This is one of the following: a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 13 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms.

[0092] Furthermore, in the above general formula (G5), R 7 ~R 14 Each of these is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C13 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C25 aryl group, a substituted or unsubstituted C2 to C25 heteroaryl group, or a substituted or unsubstituted C1 to C13 alkoxy group.

[0093] Furthermore, all hydrogen atoms in the above general formula (G5) may be deuterium.

[0094] In addition, in the above general formula (G5), A 1 Ar 1 ~Ar 3 , or R 1 ~R 6 The substituents to be substituted can refer to substituents that can be used for the same symbol in general formulas (G1) to (G4) described in <Example 1 of Organic Compounds> to <Example 4 of Organic Compounds> above.

[0095] Furthermore, in the above general formula (G5), Ar 10 , or R 9 ~R 14 Examples of heteroaryl groups that can be substituted include carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, indolocarbazolyl, benzoflocarbazolyl, benzothienocarbazolyl, indenocarbazolyl, dibenzocarbazolyl, (9-phenyl-9H-carbazolyl)phenyl, (9H-carbazole-9-yl)phenyl, and 9-phenyl-9H-carbazolyl. In particular, 3-(9-phenyl-9H-carbazolyl)phenyl, 4-(9H-carbazole-9-yl)phenyl, and 9-phenyl-9H-carbazole-3-yl groups are considered preferred substituents because the starting materials are readily available and the synthesis is simple.

[0096] Furthermore, in the above general formula (G5), Ar 10 , or R 9 ~R 14 Examples of aryl groups that can be substituted include phenyl, naphthyl, acenaphthyrenyl, anthryl, phenanthryl, biphenyl, triphenylenyl, fluorenyl, and spirofluorenyl groups.

[0097] Furthermore, in the above general formula (G5), Ar 10 , or R 9 ~R 14Examples of alkyl groups that can be substituted include propyl group, butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, octyl group, decyl group, 2-ethylhexyl group, pentan-3-yl group, heptan-4-yl group, and the like.

[0098] Furthermore, in the above general formula (G5), Ar 10 , or R 9 ~R 14 Examples of cycloalkyl groups to be substituted include cyclopropyl, cyclopentyl, cyclohexyl, adamantyl, bicyclo[2.2.1]heptyl, and tricyclo[5.2.1.0 2,6 Examples include decanyl groups and noadamantyl groups.

[0099] Furthermore, in the above general formula (G5), R 9 ~R 14 Examples of alkoxy groups that can be substituted include methoxy, ethoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, decyloxy, lauryloxy, 2-ethylhexyloxy, 3-methylbutoxy, and isopropyloxy groups.

[0100] In addition, in the above general formula (G5), A 1 Ar 1 ~Ar 3 Ar 10 , or R 1 ~R 14 Any of the substituents described above that are substituted may have other substituents. Examples of other substituents include the alkyl groups, cycloalkyl groups, trialkylsilyl groups, aryl groups, or deuterium.

[0101] As a result, it is possible to use an organic compound that has absorption particularly for light in the green region among visible light, and for example, it can be suitably used for the active layer of a light receiving device that receives green light. Further, for example, it can be suitably used for a layer in contact with the active layer of a light receiving device. Further, it is possible to provide a highly efficient photoelectric conversion device. Further, it is possible to provide a photoelectric conversion device that can operate even at a low voltage.

[0102] Note that by using the above organic compound in a light receiving device, the heat resistance can be increased without impairing the light receiving characteristics. Further, in the manufacturing process of a light receiving device, for example, in a manufacturing process involving heating such as a vacuum evaporation process, deterioration of the organic compound can be suppressed. Further, deterioration accompanying the driving of the light receiving device can be suppressed. As a result, it is possible to provide a novel organic compound excellent in convenience, usefulness, or reliability.

[0103] <Example 6 of organic compound> Further, the organic compound described in this embodiment is an organic compound represented by the following general formula (G6).

[0104] [Chemical formula]

[0105] However, in the above general formula (G6), R 1 to R 14 , and R 20 to R 44 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 13 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 13 carbon atoms.

[0106] Note that in the above general formula (G6), R 1 to R 14The substituents to be substituted can refer to substituents that can be used in the same symbol of general formula (G1) described in <Example 1 of Organic Compounds> to general formula (G5) described in <Example 5 of Organic Compounds> above.

[0107] Furthermore, in the above general formula (G6), R 20 ~R 44 Examples of heteroaryl groups that can be substituted include carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, benzonaphthofuranyl group, benzonaphthothiophenyl group, indolocarbazolyl group, benzoflocarbazolyl group, benzothienocarbazolyl group, indenocarbazolyl group, dibenzocarbazolyl group, and 9-phenyl-9H-carbazolyl group.

[0108] Furthermore, in the above general formula (G6), R 20 ~R 44 Examples of aryl groups that can be substituted include phenyl, naphthyl, acenaphthyrenyl, anthryl, phenanthryl, biphenyl, triphenylenyl, fluorenyl, and spirofluorenyl groups.

[0109] Furthermore, in the above general formula (G6), R 20 ~R 44 Examples of alkyl groups that can be substituted include propyl group, butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, octyl group, decyl group, 2-ethylhexyl group, pentan-3-yl group, heptan-4-yl group, and the like.

[0110] Furthermore, in the above general formula (G6), R 20 ~R 44 Examples of cycloalkyl groups to be substituted include cyclopropyl, cyclopentyl, cyclohexyl, adamantyl, bicyclo[2.2.1]heptyl, and tricyclo[5.2.1.0 2,6 Examples include decanyl groups and noadamantyl groups.

[0111] Furthermore, in the above general formula (G6), R 20 ~R 44 Examples of alkoxy groups that can be substituted include methoxy, ethoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, decyloxy, lauryloxy, 2-ethylhexyloxy, 3-methylbutoxy, and isopropyloxy groups.

[0112] In addition, in the above general formula (G6), R 1 ~R 14 , or R 20 ~R 44 Any of the substituents described above that are substituted may have other substituents. Examples of other substituents include the alkyl groups, cycloalkyl groups, trialkylsilyl groups, aryl groups, or deuterium.

[0113] This allows for the creation of organic compounds that absorb light, particularly in the green region of visible light, making them suitable for use, for example, in the active layer of a photodetector that receives green light. Furthermore, they are suitable for use in layers in contact with the active layer of a photodetector. Additionally, they enable the creation of highly efficient photoelectric conversion devices. Moreover, they enable the creation of photoelectric conversion devices that can operate even at low voltages.

[0114] Furthermore, by using the above-mentioned organic compound in a photodetector, heat resistance can be increased without impairing the photodetector's characteristics. Additionally, degradation of the organic compound can be suppressed during the manufacturing process of the photodetector, such as during heating processes like vacuum deposition. Degradation associated with the operation of the photodetector can also be suppressed. As a result, a novel organic compound with superior convenience, usefulness, and reliability can be provided.

[0115] Specific examples of organic compounds The specific structural formula of the organic compound according to one aspect of the present invention described above is shown below.

[0116]

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[0117]

change

[0118]

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[0119]

change

[0120]

change

[0121]

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[0122]

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[0123]

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[0124]

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[0125]

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[0126] <Synthesis method of organic compounds> A method for synthesizing an organic compound according to one aspect of the present invention will be explained below using the synthesis scheme shown.

[0127] Here, we will explain the synthesis method for the organic compound represented by the following general formula (G1). This synthesis example is R 1 ~R 6 Other organic compounds according to one aspect of the present invention having various substituents can also be synthesized by the same method by using a starting material having substituents corresponding to the relevant substitution positions.

[0128] [ka]

[0129] Note that substituent A in the above general formula (G1) and synthesis schemes (a-1) to (a-8) 1 , substituent R 1 ~R 6 , substituent Ar 1 ~Ar 4 For further information, please refer to the explanation provided in <Example 1 of Organic Compounds>.

[0130] Various reactions can be applied to synthesize the organic compound represented by general formula (G1). For example, the organic compound represented by general formula (G1) can be synthesized by carrying out the following synthesis reactions.

[0131] <Method for synthesizing organic compounds represented by general formula (G1)> The organic compound represented by the general formula (G1) of the present invention can be synthesized by the following synthesis schemes (a-1) to (a-8).

[0132] First, let's explain the synthesis scheme (a-1). That is, an anthracene compound (compound 3) can be obtained by coupling an anthracene compound (compound 1) with an aryl compound (compound 2). The synthesis scheme (a-1) is shown below.

[0133] [ka]

[0134] Next, we will explain the synthesis scheme (a-2). Specifically, an anthracene compound (compound 5) can be obtained by coupling an anthracene compound (compound 3) with an aryl compound (compound 4). The synthesis scheme (a-2) is shown below.

[0135] [ka]

[0136] Note that Ar 1 and Ar 2 If the two compounds have the same structure, compound 5 can be obtained from compound 1 in one step by coupling an anthracene compound (compound 1) and an aryl compound (compound 2) in equal amounts.

[0137] Next, we will explain the synthesis scheme (a-3). Specifically, by performing a functional group introduction reaction on the anthracene compound (compound 5), we can obtain the anthracene compound (compound 6). The synthesis scheme (a-3) is shown below.

[0138] [ka]

[0139] Next, we will explain the synthesis scheme (a-4). Specifically, an anthracene compound (compound 8) can be obtained by coupling an anthracene compound (compound 6) with an aryl compound (compound 7). The synthesis scheme (a-4) is shown below.

[0140] [ka]

[0141] Next, we will explain the synthesis scheme (a-5). Specifically, by performing a functional group introduction reaction on the anthracene compound (compound 8), we can obtain an anthracene compound with a substituted functional group (compound 9). The synthesis scheme (a-5) is shown below.

[0142] [ka]

[0143] Next, synthesis schemes (a-6) and (a-7) will be described. Specifically, by coupling an anthracene compound (compound 9) with an aryl compound (compound 10), an anthracenylamino compound (compound 11) can be obtained, and then by coupling compound 11 with an aryl compound (compound 12), the target anthracenylamino compound (G1) can be obtained. Synthesis schemes (a-6) and (a-7) are shown below.

[0144] [ka]

[0145] Furthermore, as shown in synthesis scheme (a-8), the target anthracenylamino compound (G1) can be obtained more easily than in the synthesis methods of synthesis schemes (a-6) and (a-7) by coupling an anthracene compound (compound 9) with a diarylamino compound (compound 13). Synthesis scheme (a-8) is shown below.

[0146] [ka]

[0147] In the above synthesis schemes (a-1) to (a-8), X 1 ~X 8Each of these independently represents hydrogen, halogen, boronic acid group, organoboron group, triflate group, organotin group, organozinc group, amino group, magnesium halide group, etc. 9 X represents a halogen or triflate group. 10 R represents hydrogen, organotin group, etc. 25 and R 26 represents a hydrogen group. For compound 9 or compound 10, X 7 or X 8 Compounds in which the group is an amino group are X 7 or X 8 It can be synthesized from compounds in which X is a halogen. Specifically, X 7 or X 8 By coupling a compound in which is a halogen with an amine reagent such as t-butyl carbamate, a compound with a protected amino group is synthesized, and then the amino group-protected compound is deprotected using an acidic reagent, so that in compound 9 or compound 10, X 7 or X 8 A compound in which is an amino group can be obtained. Also, in compound 9 or compound 10, X 7 or X 8 This does not apply to the synthesis method of compounds in which the group is an amino group. The specific method of the above synthesis is shown in the synthesis method of 9-phenyl-9H-carbazole-3-t-butoxycarbonylamine in step 1 of Example 2.

[0148] X 1 and X 3 Either one of them represents a boronic acid group, an organoboron group, an organotin group, an organozinc group, an amino group, or a magnesium halide group, X 1 and X 3 The other side represents hydrogen, chlorine, bromine, iodine, and a triflate group, and the aforementioned item is X 2 and X 4 , X 5 and X 6 , X 7 and X 8 The same reasoning can be applied to each combination.

[0149] The halogen is preferably chlorine, bromine, or iodine, more preferably bromine or iodine considering reactivity, and more preferably chlorine or bromine considering cost.

[0150] In synthesis schemes (a-1), (a-2), and (a-4), when performing the Suzuki-Miyaura coupling reaction using a palladium catalyst, X 1 ~X 6 The group represents a halogen group, a boronic acid group, an organoboron group, or a triflate group, with iodine, bromine, or chlorine being preferred halogens. In this reaction, palladium compounds such as bis(dibenzylideneacetone)palladium(O), palladium(II) acetate, [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, and tetrakis(triphenylphosphine)palladium(O) can be used, along with ligands such as tri(t-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine, di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, and tri(orthothyl)phosphine. In this reaction, organic bases such as sodium t-butoxide, inorganic bases such as potassium carbonate, cesium carbonate, or sodium carbonate can be used.

[0151] In this reaction, toluene, xylene, benzene, tetrahydrofuran, dioxane, ethanol, methanol, water, diethylene glycol dimethyl ether, ethylene glycol monomethyl ether, etc., can be used as solvents. However, the reagents that can be used in this reaction are not limited to these.

[0152] The reactions represented by synthesis scheme (a-1), synthesis scheme (a-2), and synthesis scheme (a-4) can be carried out using the Migita-Kosugi-Still coupling reaction with organotin compounds, the Kumada-Tamao-Coliu coupling reaction with Grignard reagents, the Negishi coupling reaction with organozinc compounds, and reactions using copper or copper compounds, etc.

[0153] In synthesis schemes (a-3) and (a-5), halogenation reactions can be used as functional group introduction reactions. Examples of such reactions include chloromination, bromination, and iodation reactions.

[0154] In chlorination reactions, N-chlorosuccinimide, oxalyl chloride, and the like can be used as reaction reagents.

[0155] In the bromination reaction, N-bromosuccinimide, N-bromophthalimide, bromine, etc., can be used as reaction reagents.

[0156] In the iodination reaction, N-iodosuccinimide, N-iodophthalimide, iodine, etc., can be used as reaction reagents.

[0157] In this halogenation reaction, chloroform, dichloroethane, dichloromethane, N,N-dimethylformamide, toluene, xylene, N-methyl-2-pyrrolidone, acetonitrile, acetic acid, ethyl acetate, etc. can be used as solvents.

[0158] Furthermore, halogens substituted into compounds through halogenation reactions can be converted into boronic acid groups, organoboron groups, organotin groups, organozinc groups, amino groups, magnesium halide groups, triflate groups, and the like. In other words, halogen-substituted compounds can be used in reactions such as the Suzuki-Miyaura coupling reaction using organoboron compounds, the Migita-Kosugi-Still coupling reaction using organotin compounds, the Kumada-Tamao-Coliu coupling reaction using Grignard reagents, the Negishi coupling reaction using organozinc compounds, and reactions using copper or copper compounds.

[0159] In synthesis schemes (a-6) to (a-8), when performing the Buchwald-Hartwig reaction using a palladium catalyst, palladium compounds such as bis(dibenzylideneacetone)palladium(O), palladium(II) acetate, [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(O), and allylpalladium(II) chloride (dimer) can be used, along with ligands such as tri(t-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine, di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, tri(ortho-tolyl)phosphine, and di-t-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (abbreviation: cBRIDP®). In this reaction, organic bases such as sodium tert-butoxide, inorganic bases such as potassium carbonate, cesium carbonate, or sodium carbonate can be used. In this reaction, toluene, xylene, benzene, tetrahydrofuran, dioxane, etc. can be used as solvents.

[0160] In synthesis schemes (a-6) to (a-8), an Ullmann reaction using copper or a copper compound can be employed. Examples of suitable bases include inorganic bases such as potassium carbonate. Suitable solvents for this reaction include 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone (DMPU), toluene, xylene, and benzene. In the Ullmann reaction, a reaction temperature of 100°C or higher yields the target product in a shorter time and with higher yield; therefore, it is preferable to use DMPU or xylene, which have high boiling points. Furthermore, a reaction temperature of 150°C or higher is even more preferable, and therefore, DMPU is more preferably used.

[0161] Furthermore, the method for synthesizing the organic compound (G1) of the present invention is not limited to synthesis scheme (a-1) to synthesis scheme (a-8).

[0162] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0163] (Embodiment 2) This embodiment describes a light-receiving device according to one aspect of the present invention.

[0164] A light-receiving device according to one aspect of the present invention has a function for detecting light (hereinafter also referred to as the light-receiving function).

[0165] Figure 1 shows a schematic cross-sectional view of a light-receiving device 200 according to one embodiment of the present invention.

[0166] ≪Basic structure of a light-receiving device≫ The basic structure of a photodetector will be described. Figure 1(A) shows a photodetector 200 having a photodetector layer 203, which includes at least an active layer and a carrier transport layer, between a pair of electrodes. Specifically, it has a structure in which the photodetector layer 203 is sandwiched between a first electrode 201 and a second electrode 202.

[0167] Furthermore, the organic compound described in <Embodiment 1> can be used in the light-receiving layer 203. In particular, the organic compound according to one embodiment of the present invention is preferably used in the active layer.

[0168] Figure 1(B) also shows the laminated structure of the light-receiving layer 203 of a light-receiving device 200, which is one embodiment of the present invention. The light-receiving layer 203 has a structure in which a first carrier transport layer 212, an active layer 213, and a second carrier transport layer 214 are sequentially laminated on a first electrode 201.

[0169] Figure 1(C) also shows the laminated structure of the light-receiving layer 203 of a light-receiving device 200 according to one embodiment of the present invention. The light-receiving layer 203 has a structure in which a first carrier injection layer 211, a first carrier transport layer 212, an active layer 213, a second carrier transport layer 214, and a second carrier injection layer 215 are sequentially laminated on a first electrode 201.

[0170] ≪Specific structure of the light-receiving device≫ Next, a specific structure of a light-receiving device 200, which is one embodiment of the present invention, will be described. This will be explained using Figure 1(C).

[0171] <First electrode and second electrode> The first electrode 201 and the second electrode 202 can be formed using materials that can be used for the first electrode 101 and the second electrode 102, as described later in Embodiment 3.

[0172] For example, by using a reflective electrode as the first electrode 201 and a semi-transparent / semi-reflective electrode as the second electrode 202, a microcavity structure can be created. This allows for the amplification of light of a specific wavelength to be detected, resulting in a highly sensitive photodetector.

[0173] <First carrier injection layer> The first carrier implantation layer 211 is a layer that implants holes from the light-receiving layer 203 into the first electrode 201, and is a layer containing a material with high hole implantation capabilities. Examples of materials with high hole implantation capabilities include aromatic amine compounds and composite materials containing hole transporting materials and acceptor materials (electron-accepting materials).

[0174] Furthermore, the first carrier injection layer 211 can be formed using a material that can be used for the hole injection layer 111, as described later in Embodiment 3.

[0175] <First carrier transport layer> The first carrier transport layer 212 is a layer that transports holes generated in the active layer 213 based on incident light to the first electrode 201, and is a layer containing a hole transport material (also called the first organic compound). The hole transport material is 10 -6 cm 2 A material having a hole mobility of / Vs or higher is preferred. However, other materials can also be used as long as they have higher hole transport capabilities than electron transport.

[0176] As the hole-transporting material (first organic compound), a π-electron-rich heteroaromatic compound or an aromatic amine (a compound having an aromatic amine skeleton) can be used.

[0177] Furthermore, carbazole derivatives, thiophene derivatives, or furan derivatives can be used as the hole transporting material (first organic compound).

[0178] Alternatively, the hole-transporting material (first organic compound) is an aromatic monoamine compound or a heteroaromatic monoamine compound and comprises at least one of the following skeletons: biphenylamine, carbazolylamine, dibenzofuranylamine, dibenzothiophenylamine, fluorenylamine, or spirofluorenylamine.

[0179] Alternatively, the hole-transporting material (first organic compound) is an aromatic monoamine compound or a heteroaromatic monoamine compound and has two or more skeletons selected from biphenylamine, carbazolylamine, dibenzofuranylamine, dibenzothiophenylamine, fluorenylamine, and spirofluorenylamine.

[0180] Furthermore, if the hole-transporting material (the first organic compound) is an aromatic monoamine compound or a heteroaromatic monoamine compound and has two or more skeletons selected from biphenylamine, carbazolylamine, dibenzofuranylamine, dibenzothiophenylamine, fluorenylamine, and spirofluorenylamine, then one nitrogen atom may be contained within two or more skeletons. For example, in an aromatic monoamine compound, if fluorene and biphenyl are bonded to the nitrogen of the monoamine, then the compound can be said to be an aromatic monoamine compound having a fluorenylamine skeleton and a biphenylamine skeleton.

[0181] Furthermore, the biphenylamine, carbazolylamine, dibenzofuranylamine, dibenzothiophenylamine, fluorenylamine, and spirofluorenylamine mentioned above may have substituents as the skeleton of the hole transport material (first organic compound). For example, substituents include substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 1 to 20 carbon atoms, or substituted or unsubstituted heteroaryl groups having 4 to 30 carbon atoms.

[0182] Alternatively, the hole transport material (first organic compound) is preferably a monoamine compound having a triarylamine skeleton (the aryl group in the triarylamine compound shall also include heteroaryl groups). For example, it is an organic compound represented by the following general formula (Gh-1).

[0183] [ka]

[0184] In the above general formula (Gh-1), Ar 11 ~Ar 13 Each of these independently represents hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 4 to 30 carbon atoms.

[0185] Alternatively, the hole-transporting material (first organic compound) is an organic compound represented by the following general formula (Gh-2).

[0186] [ka]

[0187] In the above general formula (Gh-2), Ar 12 and Ar 13Each of these independently represents hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 4 to 30 carbon atoms, and R 511 ~R 520 Each independently represents hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 4 to 30 carbon atoms, R 519 and R 520 They may be joined to each other to form a ring.

[0188] Alternatively, the hole-transporting material (first organic compound) is an organic compound represented by the following general formula (Gh-3).

[0189] [ka]

[0190] In the above general formula (Gh-3), Ar 12 and Ar 13 Each of these independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 4 to 30 carbon atoms, R 521 ~R 536 Each of these independently represents hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 4 to 30 carbon atoms.

[0191] Alternatively, the hole-transporting material (first organic compound) is an organic compound represented by the following general formula (Gh-4).

[0192] [ka]

[0193] In the above general formula (Gh-4), Ar 13 R represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 4 to 30 carbon atoms. 511 ~R 520 and R 540 ~R 549 Each independently represents hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 4 to 30 carbon atoms, R 519 and R 520 They may be bonded to each other to form a ring, R 548 and R 549 They may be joined to each other to form a ring.

[0194] Alternatively, the hole-transporting material (first organic compound) is an organic compound represented by the following general formula (Gh-5).

[0195] [ka]

[0196] In the above general formula (Gh-5), Ar 13 R represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 4 to 30 carbon atoms. 511 ~R 520 and R 550 ~R 559 Each independently represents hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 4 to 30 carbon atoms, R 519 and R 520 They may be joined to each other to form a ring.

[0197] Alternatively, the hole-transporting material (first organic compound) is an organic compound represented by the following general formula (Gh-6).

[0198] [ka]

[0199] In the above general formula (Gh-6), R 560 ~R 574 Each of these independently represents hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 4 to 30 carbon atoms.

[0200] In the above general formula (Gh-2), R 511 ~R 520 , R in the above general formula (Gh-3) 521 ~R 536 , R in the above general formula (Gh-4) 511 ~R 520 and R 540 ~R 549 , R in the above general formula (Gh-5) 511 ~R 520 and R 550 ~R 559 , and R in the above general formula (Gh-6) 560 ~R 574 In addition to the substituents described above, each of these independently represents a halogen, a substituted or unsubstituted C1 to C13 halogenated alkyl group, a cyano group, or a substituted or unsubstituted C1 to C13 alkoxy group.

[0201] In the above general formula (Gh-2), R 511 ~R 520 , R in the above general formula (Gh-3) 521 ~R 536 , R in the above general formula (Gh-4) 511 ~R 520 and R 540 ~R 549 , R in the above general formula (Gh-5) 511~R 520 and R 550 ~R 559 , and R in the above general formula (Gh-6) 560 ~R 574 Specifically, the substituents are preferably those represented by the following formulas (R-1) to (R-38) and (R-41) to (R-117). Note that * in the formulas represents a bond.

[0202] Also, Ar in the above general formula (Gh-1) 11 ~Ar 13 , Ar in the above general formulas (Gh-2) and (Gh-3) 12 and Ar 13 , and Ar in the above general formulas (Gh-4) and (Gh-5) 13 Specifically, the substituent is preferably represented by the following formulas (R-41) to (R-117). Note that * in the formula represents a bond.

[0203] [ka]

[0204] [ka]

[0205] [ka]

[0206] [ka]

[0207] [ka]

[0208] Next, specific examples of organic compounds (hole transport materials) represented by the above general formulas (Gh-1) to (Gh-6) are shown below.

[0209]

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[0210]

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[0211]

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[0212]

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[0213]

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[0214]

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[0215]

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[0216]

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[0217]

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[0218]

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[0219] The organic compounds represented by the above structural formulas (1201) to (1302) are examples of organic compounds (hole transport materials) represented by the above general formulas (Gh-1) to (Gh-6), and specific examples are not limited to these.

[0220] Furthermore, the first carrier transport layer 212 can also be formed using a material that can be used for the hole transport layer 112, as described later in Embodiment 3.

[0221] Furthermore, the first carrier transport layer 212 may be a single layer, or it may be a structure in which two or more layers made of the above material are stacked.

[0222] In the light-receiving device shown in this embodiment, the same organic compound as the first carrier transport layer 212 can be used in the active layer 213. Using the same organic compound in both the first carrier transport layer 212 and the active layer 213 is preferable because it allows for more efficient transport of carriers from the first carrier transport layer 212 to the active layer 213.

[0223] <Active layer> The active layer 213 is a layer that generates carriers based on incident light and contains a semiconductor. Examples of such semiconductors include inorganic semiconductors such as silicon and organic semiconductors containing organic compounds. In this embodiment, an example is shown in which an organic semiconductor is used as the semiconductor of the active layer. Using an organic semiconductor is preferable because the light-emitting layer and the active layer can be formed using the same method (for example, vacuum deposition), and the manufacturing equipment can be shared.

[0224] Furthermore, the active layer 213 comprises at least a p-type semiconductor material (also called a third organic compound) and an n-type semiconductor material (also called a fourth organic compound).

[0225] Examples of p-type semiconductor materials (third organic compounds) include electron-donating organic semiconductor materials such as copper(II) phthalocyanine (CuPc), tetraphenyldibenzoperiflanthene (DBP), zinc phthalocyanine (ZnPc), tin phthalocyanine (SnPc), and quinacridone.

[0226] Furthermore, examples of p-type semiconductor materials (third organic compounds) include carbazole derivatives, thiophene derivatives, furan derivatives, and compounds having an aromatic amine skeleton. In addition, examples of p-type semiconductor materials include naphthalene derivatives, anthracene derivatives, pyrene derivatives, triphenylene derivatives, fluorene derivatives, pyrrole derivatives, benzofuran derivatives, benzothiophene derivatives, indole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, indolocarbazole derivatives, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, quinacridone derivatives, polyphenylenevinylene derivatives, polyparaphenylene derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives, and polythiophene derivatives.

[0227] Furthermore, the p-type semiconductor material (third organic compound) is preferably an organic compound represented by the following general formula (Ga-1).

[0228] [ka]

[0229] In the above general formula (Ga-1), R 21 ~R 30Each of these independently represents hydrogen, deuterium, a substituted or unsubstituted C1-C13 alkyl group, a C3-C13 cycloalkyl group, a halogen, a substituted or unsubstituted C1-C13 halogenated alkyl group, a cyano group, a substituted or unsubstituted C1-C13 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group, where m represents an integer from 2 to 5, and R 21 ~R 24 and R 25 ~R 28 These elements may be bonded to each other to form a ring (including a fused ring).

[0230] In the above general formula (Ga-1), R 21 ~R 30 The substituent is preferably represented by the following formulas (Ra-1) to (Ra-77). Note that * in the formulas represents a bond.

[0231] [ka]

[0232] [ka]

[0233] [ka]

[0234] Next, specific examples of p-type semiconductor materials represented by the above general formula (Ga-1) are shown below. Note that R 21 ~R 24 and R 25 ~R 28 A specific example of a case where these elements may bond to each other to form a ring (including a fused ring) is the following compound (1110).

[0235] [ka]

[0236] [ka]

[0237] The organic compounds represented by the above structural formulas (1100) to (1116) are examples of organic compounds represented by the above general formula (Ga-1), but specific examples of p-type semiconductor materials (third organic compounds) are not limited to these.

[0238] n-type semiconductor materials (fourth organic compound) include fullerenes (e.g., C 60 , C 70 Examples include electron-accepting organic semiconductor materials such as fullerene derivatives. Fullerenes have a shape like a soccer ball, and this shape is energetically stable. Fullerenes have deep (low) levels in both the HOMO level and the LUMO (Lowest Unoccupied Molecular Orbital) level. Because the LUMO level is deep, fullerenes have extremely high electron-accepting properties. Normally, when π-electron conjugation (resonance) spreads out in a plane, as in benzene, electron-donating properties increase, but because fullerenes have a spherical shape, they have high electron-accepting properties despite the large spread of π-electron conjugation. High electron-accepting properties allow for fast and efficient charge separation, making them useful as photodetectors. 60 , C 70 Both have a broad absorption band in the visible light region, and especially C 70 is C 60Compared to [another compound], it is preferable because it has a larger π-electron conjugation system and a broad absorption band in the long-wavelength region. Other examples of fullerene derivatives include [6,6]-Phenyl-C71-butyric acid methyl ester (abbreviated as PC70BM), [6,6]-Phenyl-C61-butyric acid methyl ester (abbreviated as PC60BM), and 1',1'',4',4''-Tetrahydro-di[1,4]methanonaphthaleno[1,2:2',3',56,60:2'',3''][5,6]fullerene-C60 (abbreviated as ICBA).

[0239] Furthermore, examples of n-type semiconductor materials (fourth organic compounds) include metal complexes having a quinoline skeleton, metal complexes having a benzoquinoline skeleton, metal complexes having an oxazole skeleton, metal complexes having a thiazole skeleton, oxadiazole derivatives, triazole derivatives, imidazole derivatives, oxazole derivatives, thiazole derivatives, phenanthroline derivatives, quinoline derivatives, benzoquinoline derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, pyridine derivatives, bipyridine derivatives, pyrimidine derivatives, naphthalene derivatives, anthracene derivatives, coumarin derivatives, rhodamine derivatives, triazine derivatives, quinone derivatives, and the like.

[0240] Furthermore, the n-type semiconductor material (the fourth organic compound) is preferably an organic compound represented by any one of the following general formulas (Gb-1) to (Gb-3).

[0241] [ka]

[0242] In the above general formulas (Gb-1) to (Gb-3), X 30 ~X 45 Each of these independently represents oxygen or sulfur, and n 10 and n 11 Each of these independently represents an integer from 0 to 4, and n 20 〜n 26Each of these independently represents an integer from 0 to 3, and n 24 〜n 26 At least one of them represents an integer between 1 and 3, R 100 ~R 117 Each of these independently represents hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C13 alkyl group, a C3 to C13 cycloalkyl group, a substituted or unsubstituted C1 to C13 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C13 halogenated alkyl group, or a halogen, R 300 ~R 317 Each of these independently represents hydrogen, deuterium, a cyano group, fluorine, chlorine, a substituted or unsubstituted C1 to C13 halogenated alkyl group, or a substituted or unsubstituted C1 to C13 alkoxy group.

[0243] In the above general formulas (Gb-1) to (Gb-3), R 100 ~R 117 The substituents are preferably those represented by the following formulas (Rb-1) to (Rb-79) and (R-41) to (R-117). Note that * in the formulas represents a bond.

[0244] Furthermore, in the above general formulas (Gb-1) to (Gb-3), R 300 ~R 317 The substituent is preferably represented by the following formulas (Rb-1) to (Rb-4), (Rb-7), and (R-33) to (R-72). In the formulas, * represents a bond.

[0245] [ka]

[0246] [ka]

[0247] [ka]

[0248]

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[0249]

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[0250]

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[0251]

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[0252]

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[0253]

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[0254]

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[0255]

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[0256]

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[0257]

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[0258] Next, specific examples of n-type semiconductor materials represented by the above general formula (Gb-1) are shown below.

[0259] [ka]

[0260] The organic compounds represented by the above structural formulas (1300) to (1312) are examples of organic compounds (n-type semiconductor materials) represented by the above general formulas (Gb-1) to (Gb-3), but specific examples are not limited to these.

[0261] Furthermore, an organic compound represented by the following general formula (Gc-1) may be used as the n-type semiconductor material (fourth organic compound).

[0262] [ka]

[0263] In the above general formula (Gc-1), R 40 and R 41 Each independently represents hydrogen, a substituted or unsubstituted chain alkyl group having 1 to 13 carbon atoms, a branched alkyl group having 3 to 13 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted aromatic alkyl group having 6 to 13 carbon atoms, R 42 ~R 49 Each of these independently represents hydrogen, a substituted or unsubstituted C1-C13 alkyl group, a substituted or unsubstituted C1-C13 halogenated alkyl group, a substituted or unsubstituted C3-C13 cycloalkyl group, or a halogen.

[0264] In the above general formula (Gc-1), R 40 and R 41 Each of these is preferably a chain-like alkyl group having 2 to 12 carbon atoms. Furthermore, each of these is more preferably a branched alkyl group. This can improve solubility.

[0265] Next, specific examples of n-type semiconductor materials (fourth organic compound) represented by the above general formula (Gc-1) are shown below.

[0266] [ka]

[0267] The organic compounds represented by the above structural formulas (1400) to (1403) are examples of organic compounds represented by the above general formula (Gc-1) (n-type semiconductor materials (fourth organic compound)), and specific examples are not limited to these.

[0268] Furthermore, the active layer 213 is preferably a multilayer film consisting of a first layer having a p-type semiconductor material (third organic compound) and a second layer having an n-type semiconductor material (fourth organic compound).

[0269] Furthermore, in the photodetector devices of the above configurations, the active layer 213 is preferably a mixed film having a p-type semiconductor material (third organic compound) and an n-type semiconductor material (fourth organic compound).

[0270] Furthermore, it is preferable that the HOMO level of electron-donating organic semiconductor materials be shallower (higher) than that of electron-accepting organic semiconductor materials. Similarly, it is preferable that the LUMO level of electron-donating organic semiconductor materials be shallower (higher) than that of electron-accepting organic semiconductor materials.

[0271] Furthermore, spherical fullerenes may be used as electron-accepting organic semiconductor materials, and organic semiconductor materials with a near-planar shape may be used as electron-donating organic semiconductor materials. Molecules with similar shapes tend to aggregate easily, and when molecules of the same type aggregate, their molecular orbital energy levels are close, which can enhance carrier transport.

[0272] <Second carrier transport layer> The second carrier transport layer 214 is a layer that transports electrons generated in the active layer 213 based on incident light to the second electrode 202, and is a layer containing an electron transport material (also called a second organic compound). The electron transport material is 1 × 10 -6 cm 2 A material having an electron mobility of / Vs or higher is preferred. However, other materials can also be used as long as they have higher electron transport capabilities than holes.

[0273] As the electron-transporting material (second organic compound), a π-electron-deficient heteroaromatic compound can be used.

[0274] Furthermore, as electron transport materials (second organic compounds), metal complexes having a quinoline skeleton, metal complexes having a benzoquinoline skeleton, metal complexes having an oxazole skeleton, metal complexes having a thiazole skeleton, etc., as well as oxadiazole derivatives, triazole derivatives, imidazole derivatives, oxazole derivatives, thiazole derivatives, phenanthroline derivatives, quinoline derivatives having a quinoline ligand, benzoquinoline derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, pyridine derivatives, bipyridine derivatives, pyrimidine derivatives, and other π-electron-deficient heteroaromatic compounds containing nitrogen-containing heteroaromatic compounds can be used.

[0275] Alternatively, the electron-transporting material (the second organic compound) is a compound having a triazine ring.

[0276] Alternatively, the electron-transporting material (second organic compound) is an organic compound represented by the following general formula (Ge-1).

[0277] [ka]

[0278] In the above general formula (Ge-1), Ar 1 ~Ar 3Each of these independently represents hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and X 1 and X 2 Each of these independently represents carbon or nitrogen, and X 1 and X 2 If either or both of the atoms are carbon, the carbon is bonded to hydrogen, or to a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms.

[0279] Alternatively, the electron-transporting material (second organic compound) is an organic compound represented by the following general formula (Ge-2).

[0280] [ka]

[0281] In the above general formula (Ge-2), Ar 1 ~Ar 3 Each of these independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, X 2 X represents carbon or nitrogen. 2 If carbon is present, carbon is bonded to hydrogen, or to a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms.

[0282] Alternatively, the electron-transporting material (second organic compound) is an organic compound represented by the following general formula (Ge-3).

[0283] [ka]

[0284] In the above general formula (Ge-3), Ar 1 ~Ar 3 These terms independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0285] Alternatively, the electron-transporting material (second organic compound) is an organic compound represented by the following general formula (Ge-4).

[0286] [ka]

[0287] In the above general formula (Ge-4), Ar 3 R represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. 1 ~R 10 Each of these independently represents hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0288] In the above general formula (Ge-4), R 1 ~R 10 In addition to the substituents mentioned above, this represents halogens, substituted or unsubstituted C1 to C13 halogenated alkyl groups, cyano groups, and substituted or unsubstituted C1 to C13 alkoxy groups.

[0289] In the above general formula (Ge-4), R 1 ~R 10 Preferably, the substituent is represented by the following formulas (R-1) to (R-38), the substituent represented by the following formulas (R-41) to (R-116), and the substituent represented by the following formulas (R-118) to (R-131).

[0290] Furthermore, Ar in the above general formulas (Ge-1) to (Ge-3)1 ~Ar 3 and Ar in the above general formula (Ge-4) 3 Preferably, the substituents are those represented by formulas (R-41) to (R-116) and those represented by formulas (R-118) to (R-131).

[0291] [ka]

[0292] [ka]

[0293] [ka]

[0294] [ka]

[0295] [ka]

[0296] [ka]

[0297] Next, specific examples of a second organic compound having the above-described components are shown below.

[0298] [ka]

[0299] [ka]

[0300] The organic compounds represented by the above structural formulas (1500) to (1524) are examples of organic compounds represented by the above general formulas (Ge-1) to (Ge-4), but the specific examples of the second organic compound are not limited to these.

[0301] Furthermore, as the second organic compound, organic compounds represented by the following structural formulas (1600) to (1622) can be used.

[0302] [ka]

[0303] [ka]

[0304] Furthermore, the second carrier transport layer 214 can also be formed using a material that can be used for the electron transport layer 114, as described later in Embodiment 3.

[0305] Furthermore, the second carrier transport layer 214 may be a single layer, or it may have a structure in which two or more layers made of the above material are stacked.

[0306] <Second carrier injection layer> The second carrier injection layer 215 is a layer for increasing the efficiency of electron injection from the photodetector layer 203 to the second electrode 202, and is a layer containing a material with high electron injection properties. Alkali metals, alkaline earth metals, or compounds thereof can be used as the material with high electron injection properties. A composite material containing an electron transport material and a donor material (electron-donating material) can also be used as the material with high electron injection properties.

[0307] The second carrier injection layer 215 can be formed using a material that can be used for the electron injection layer 115, as described later in Embodiment 3.

[0308] Furthermore, by providing a charge generation layer between the two light-receiving layers 203, a structure in which multiple light-receiving layers are stacked between a pair of electrodes (also called a tandem structure) can be created. Additionally, by providing a charge generation layer between different light-receiving layers, a stacked structure of three or more light-receiving layers can be created. The charge generation layer can be formed using a material that can be used for the charge generation layer 106, as described later in Embodiment 3.

[0309] The layers constituting the light-receiving layer 203 of the light-receiving device shown in this embodiment (first carrier injection layer 211, first carrier transport layer 212, active layer 213, second carrier transport layer 214, second carrier injection layer 215) are not limited to the materials shown in this embodiment, and other materials can be used in combination as long as they can satisfy the function of each layer.

[0310] In this specification, the terms "layer" and "film" may be used interchangeably as appropriate.

[0311] Furthermore, a light-receiving device according to one embodiment of the present invention has the function of detecting visible light. Also, a light-receiving device according to one embodiment of the present invention is sensitive to visible light. Furthermore, it is preferable that a light-receiving device according to one embodiment of the present invention has the function of detecting both visible light and infrared light. Furthermore, it is preferable that a light-receiving device according to one embodiment of the present invention is sensitive to both visible light and infrared light.

[0312] In this specification, the wavelength range for blue (B) is defined as 400 nm to less than 490 nm, and blue (B) light is defined as having at least one emission spectral peak in this wavelength range. The wavelength range for green (G) is defined as 490 nm to less than 580 nm, and green (G) light is defined as having at least one emission spectral peak in this wavelength range. The wavelength range for red (R) is defined as 580 nm to less than 700 nm, and red (R) light is defined as having at least one emission spectral peak in this wavelength range. In this specification, the wavelength range for visible light is defined as 400 nm to less than 700 nm, and visible light is defined as having at least one emission spectral peak in this wavelength range. The wavelength range for infrared (IR) is defined as 700 nm to less than 900 nm, and infrared (IR) light is defined as having at least one emission spectral peak in this wavelength range.

[0313] The light-receiving device according to one aspect of the present invention described above can be used in a display device using an organic EL device. In other words, the light-receiving device according to one aspect of the present invention can be incorporated into a display device using an organic EL device. As an example, Figure 2(A) shows a schematic cross-sectional view of a display device 810 in which a light-emitting device 805a and a light-receiving device 805b are formed on the same substrate.

[0314] Since the display device 810 has a light-emitting device 805a and a light-receiving device 805b, in addition to the function of displaying images, it also has one or both of the functions of imaging and sensing.

[0315] The light-emitting device 805a has a function of emitting light (hereinafter also referred to as the light-emitting function). The light-emitting device 805a has an electrode 801a, an EL layer 803a, and an electrode 802. The EL layer 803a, sandwiched between the electrode 801a and the electrode 802, has at least a light-emitting layer. The light-emitting layer has a light-emitting material. By applying a voltage between the electrode 801a and the electrode 802, light is emitted from the EL layer 803a. In addition to the light-emitting layer, the EL layer 803a may have various layers such as a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a carrier (hole or electron) blocking layer, and a charge generation layer. The configuration of the light-emitting device, which is an organic EL device described later in Embodiment 3, can be applied to the light-emitting device 805a.

[0316] The light-receiving device 805b has a function to detect light (hereinafter also referred to as the light-receiving function). The light-receiving device 805b has an electrode 801b, a light-receiving layer 803b, and an electrode 802. The light-receiving layer 803b, which is sandwiched between electrodes 801b and 802, has at least an active layer. The light-receiving device 805b functions as a photoelectric conversion device and can generate an electric charge from light incident on the light-receiving layer 803b, which can be extracted as an electric current. At this time, a voltage may be applied between electrodes 801b and 802. The amount of charge generated is determined based on the amount of light incident on the light-receiving layer 803b. The configuration of the light-receiving device 200 described above can be applied to the light-receiving device 805b.

[0317] The light-receiving device 805b can be easily made thinner, lighter, and larger in area, and its shape and design offer a high degree of freedom, making it applicable to various display devices. Furthermore, the EL layer 803a of the light-emitting device 805a and the light-receiving layer 803b of the light-receiving device 805b can be formed using the same method (e.g., vacuum deposition), and it is preferable that common manufacturing equipment can be used.

[0318] Electrodes 801a and 801b are provided on the same plane. Figure 2(A) shows a configuration in which electrodes 801a and 801b are provided on the substrate 800. Electrodes 801a and 801b can be formed, for example, by processing a conductive film formed on the substrate 800 into island shapes. In other words, electrodes 801a and 801b can be formed through the same process.

[0319] The substrate 800 can be a heat-resistant substrate capable of withstanding the formation of the light-emitting device 805a and the light-receiving device 805b. When an insulating substrate is used as the substrate 800, glass substrates, quartz substrates, sapphire substrates, ceramic substrates, organic resin substrates, etc., can be used. In addition, semiconductor substrates such as single-crystal semiconductor substrates made of silicon or silicon carbide, polycrystalline semiconductor substrates, compound semiconductor substrates such as silicon germanium, and SOI substrates can be used.

[0320] In particular, it is preferable to use a substrate 800 on which a semiconductor circuit including semiconductor elements such as transistors is formed on the aforementioned insulating substrate or semiconductor substrate. It is preferable that the semiconductor circuit constitutes, for example, a pixel circuit, a gate line driving circuit (gate driver), a source line driving circuit (source driver), etc. In addition to the above, an arithmetic circuit, a memory circuit, etc. may also be configured.

[0321] Furthermore, electrode 802 is an electrode made of a layer common to both the light-emitting device 805a and the light-receiving device 805b. Of these electrodes, the electrode that emits light or receives light as an incident electrode preferably uses a conductive film that transmits visible light and infrared light. The electrode that does not emit light or receives light as an incident electrode preferably uses a conductive film that reflects visible light and infrared light.

[0322] In one embodiment of the present invention, the electrode 802 in the display device functions as one of the electrodes of the light-emitting device 805a and the light-receiving device 805b.

[0323] Figure 2(B) shows the case where electrode 801a of the light-emitting device 805a has a higher potential than electrode 802. In this case, electrode 801a functions as the anode of the light-emitting device 805a, and electrode 802 functions as the cathode. Also, electrode 801b of the light-receiving device 805b has a lower potential than electrode 802. In Figure 2(B), to make the direction of current flow clearer, the circuit symbol for the light-emitting diode is shown to the left of the light-emitting device 805a, and the circuit symbol for the photodiode is shown to the right of the light-receiving device 805b. Furthermore, the direction of carrier (electron and hole) flow is schematically indicated by arrows within each device.

[0324] In the configuration shown in Figure 2(B), when a first potential is supplied to electrode 801a via the first wiring, a second potential is supplied to electrode 802 via the second wiring, and a third potential is supplied to electrode 801b via the third wiring, the relationship between the magnitudes of each potential is: first potential > second potential > third potential.

[0325] Figure 2(C) shows the case where electrode 801a of the light-emitting device 805a has a lower potential than electrode 802. In this case, electrode 801a functions as the cathode of the light-emitting device 805a, and electrode 802 functions as the anode. Also, electrode 801b of the light-receiving device 805b has a lower potential than electrode 802 and a higher potential than electrode 801a. In Figure 2(C), to make the direction of current flow clearer, the circuit symbol for the light-emitting diode is shown to the left of the light-emitting device 805a, and the circuit symbol for the photodiode is shown to the right of the light-receiving device 805b. The direction of carrier (electron and hole) flow is schematically indicated by arrows within each device.

[0326] In the configuration shown in Figure 2(C), when a first potential is supplied to electrode 801a via the first wiring, a second potential is supplied to electrode 802 via the second wiring, and a third potential is supplied to electrode 801b via the third wiring, the relationship between the magnitudes of each potential is second potential > third potential > first potential.

[0327] Figure 3(A) shows a modified display device 810A, which is a modified version of the display device 810. The display device 810A differs from the display device 810 in that it has common layers 806 and 807. In the light-emitting device 805a, common layers 806 and 807 function as part of the EL layer 803a. The common layer 806 includes, for example, a hole injection layer and a hole transport layer. The common layer 807 includes, for example, an electron transport layer and an electron injection layer.

[0328] By having a common layer 806 and a common layer 807, a light-receiving element can be incorporated without significantly increasing the number of paint layers, and the display device 810A can be manufactured with high throughput.

[0329] Figure 3(B) shows a modified display device 810, called display device 810B. Display device 810B differs from display device 810 in that the EL layer 803a has layers 806a and 807a, and the light-receiving layer 803b has layers 806b and 807b. Layers 806a and 806b are made of different materials, for example, a hole injection layer and a hole transport layer. Layers 806a and 806b may be made of a common material. Layers 807a and 807b are made of different materials, for example, an electron transport layer and an electron injection layer. Layers 807a and 807b may be made of a common material.

[0330] By selecting the optimal materials for constructing the light-emitting device 805a for layers 806a and 807a, and the optimal materials for constructing the light-receiving device 805b for layers 806b and 807b, the performance of the light-emitting device 805a and the light-receiving device 805b can be enhanced in the display device 810B.

[0331] The resolution of the light-receiving device 805b is 100 ppi or more, preferably 200 ppi or more, more preferably 300 ppi or more, more preferably 400 ppi or more, and even more preferably 500 ppi or more, and can be 2000 ppi or less, 1000 ppi or less, or 600 ppi or less. In particular, by arranging the light-receiving device 805b with a resolution of 200 ppi or more and 600 ppi or less, preferably 300 ppi or more and 600 ppi or less, it can be suitably used for fingerprint imaging. When performing fingerprint authentication using the display device 810, increasing the resolution of the light-receiving device 805b allows for the extraction of fingerprint feature points (Minutia) with high accuracy, for example, thereby improving the accuracy of fingerprint authentication. Furthermore, a resolution of 500 ppi or more is preferable because it allows compliance with standards such as those of the National Institute of Standards and Technology (NIST). Assuming the resolution of the light-receiving device is 500 ppi, each pixel would be 50.8 μm in size, which is sufficient resolution to capture the width of a fingerprint (typically between 300 μm and 500 μm).

[0332] Furthermore, the configuration shown in this embodiment can be used in appropriate combination with the configurations shown in other embodiments.

[0333] (Embodiment 3) In this embodiment, other configurations of the light-emitting device shown in Embodiment 2 will be explained using Figures 4(A) to 4(E).

[0334] ≪Basic Structure of Light-Emitting Devices≫ The basic structure of a light-emitting device will be described. Figure 4(A) shows a light-emitting device having an EL layer containing a light-emitting layer between a pair of electrodes. Specifically, it has a structure in which an EL layer 103 is sandwiched between a first electrode 101 and a second electrode 102.

[0335] Furthermore, Figure 4(B) shows a light-emitting device with a stacked structure (tandem structure) having multiple (two layers in Figure 4(B)) EL layers (103a, 103b) between a pair of electrodes, and a charge generation layer 106 between the EL layers. A light-emitting device with a tandem structure can realize a light-emitting device that can be driven at low voltage and consumes low power.

[0336] The charge generation layer 106 has the function of injecting electrons into one EL layer (103a or 103b) and holes into the other EL layer (103b or 103a) when a potential difference is created between the first electrode 101 and the second electrode 102. Therefore, in Figure 4(B), when a voltage is applied to the first electrode 101 such that the potential is higher than that of the second electrode 102, electrons are injected from the charge generation layer 106 into the EL layer 103a and holes are injected into the EL layer 103b.

[0337] Furthermore, from the viewpoint of light extraction efficiency, it is preferable that the charge generation layer 106 is transparent to visible light (specifically, the transmittance of visible light to the charge generation layer 106 is 40% or more). In addition, the charge generation layer 106 can function even if its conductivity is lower than that of the first electrode 101 or the second electrode 102.

[0338] Figure 4(C) shows the laminated structure of the EL layer 103 of a light-emitting device according to one embodiment of the present invention. In this case, the first electrode 101 functions as an anode and the second electrode 102 functions as a cathode. The EL layer 103 has a structure in which a hole injection layer 111, a hole transport layer 112, a light-emitting layer 113, an electron transport layer 114, and an electron injection layer 115 are sequentially laminated on the first electrode 101. The light-emitting layer 113 may be a configuration in which multiple light-emitting layers with different emission colors are laminated. For example, a light-emitting layer containing a red light-emitting material, a light-emitting layer containing a green light-emitting material, and a light-emitting layer containing a blue light-emitting material may be laminated, or laminated via a layer having a carrier transport material. Alternatively, a combination of a light-emitting layer containing a yellow light-emitting material and a light-emitting layer containing a blue light-emitting material may be used. However, the laminated structure of the light-emitting layer 113 is not limited to the above. For example, the light-emitting layer 113 may be a structure in which multiple light-emitting layers of the same emission color are stacked. For example, a first light-emitting layer containing a blue light-emitting material and a second light-emitting layer containing a blue light-emitting material may be stacked, or a structure in which they are stacked via a layer having a carrier transport material. In the case of a structure in which multiple light-emitting layers of the same emission color are stacked, reliability can be increased compared to a single-layer structure. Also, even when there are multiple EL layers as in the tandem structure shown in Figure 4(B), each EL layer is stacked sequentially from the anode side as described above. Furthermore, if the first electrode 101 is the cathode and the second electrode 102 is the anode, the stacking order of the EL layer 103 is reversed. Specifically, on the first electrode 101, which is the cathode, 111 is an electron injection layer, 112 is an electron transport layer, 113 is a light-emitting layer, 114 is a hole transport layer, and 115 is a hole injection layer.

[0339] The light-emitting layers 113 contained in the EL layers (103, 103a, 103b) each contain a light-emitting material or a combination of multiple materials as appropriate, and can be configured to produce fluorescence emission or phosphorescence emission exhibiting a desired emission color. Alternatively, the light-emitting layers 113 may be arranged in a laminated structure with different emission colors. In this case, the light-emitting material or other material used in each laminated light-emitting layer may be made of different materials. Furthermore, a configuration in which different emission colors can be obtained from multiple EL layers (103a, 103b) as shown in Figure 4(B) is also possible. In this case as well, the light-emitting material or other material used in each light-emitting layer may be made of different materials.

[0340] Furthermore, in a light-emitting device according to one aspect of the present invention, for example, by using a reflective electrode as the first electrode 101 shown in Figure 4(C) and a semi-transparent / semi-reflective electrode as the second electrode 102, and by using a micro-cavity structure, the light emitted from the light-emitting layer 113 contained in the EL layer 103 can be made to resonate between the two electrodes, thereby strengthening the light emitted from the second electrode 102.

[0341] Furthermore, if the first electrode 101 of the light-emitting device is a reflective electrode consisting of a laminated structure of a reflective conductive material and a translucent conductive material (transparent conductive film), optical adjustment can be performed by controlling the film thickness of the transparent conductive film. Specifically, it is preferable to adjust the optical distance (product of film thickness and refractive index) between the first electrode 101 and the second electrode 102 to be mλ / 2 (where m is a natural number) or close to it, with respect to the wavelength λ of light obtained from the light-emitting layer 113.

[0342] Furthermore, in order to amplify the desired light (wavelength: λ) obtained from the light-emitting layer 113, it is preferable to adjust the optical distance from the first electrode 101 to the region of the light-emitting layer 113 where the desired light is obtained (light-emitting region), and the optical distance from the second electrode 102 to the region of the light-emitting layer 113 where the desired light is obtained (light-emitting region), so that they are (2m'+1)λ / 4 (where m' is a natural number) or close to it. The light-emitting region referred to here is the region in the light-emitting layer 113 where holes and electrons recombine.

[0343] By performing such optical adjustments, the spectrum of specific monochromatic light obtained from the light-emitting layer 113 can be narrowed, resulting in emission with good color purity.

[0344] However, in the above case, the optical distance between the first electrode 101 and the second electrode 102 can be precisely defined as the total thickness from the reflective region of the first electrode 101 to the reflective region of the second electrode 102. However, since it is difficult to precisely determine the reflective region of the first electrode 101 or the second electrode 102, the above effects can be sufficiently obtained by assuming that any position on the first electrode 101 and the second electrode 102 are reflective regions. Furthermore, the optical distance between the first electrode 101 and the light-emitting layer from which the desired light is obtained can be precisely defined as the optical distance between the reflective region of the first electrode 101 and the light-emitting region of the light-emitting layer from which the desired light is obtained. However, since it is difficult to precisely determine the reflective region of the first electrode 101 or the light-emitting region of the light-emitting layer from which the desired light is obtained, the above effects can be sufficiently obtained by assuming that any position on the first electrode 101 is a reflective region and any position on the light-emitting layer from which the desired light is obtained is a light-emitting region.

[0345] The light-emitting device shown in Figure 4(D) is a light-emitting device having a tandem structure and a microcavity structure, which allows for the extraction of light of different wavelengths (monochromatic light) from each EL layer (103a, 103b). Therefore, color separation (e.g., RGB) to obtain different emission colors is unnecessary. Consequently, high resolution can be easily achieved. It can also be combined with a colored layer (color filter). Furthermore, it is possible to strengthen the emission intensity in the front direction at a specific wavelength, thereby reducing power consumption.

[0346] The light-emitting device shown in Figure 4(E) is an example of a tandem-structured light-emitting device shown in Figure 4(B). As shown in the figure, it has a structure in which three EL layers (103a, 103b, 103c) are stacked with charge generation layers (106a, 106b) in between. Each of the three EL layers (103a, 103b, 103c) has a light-emitting layer (113a, 113b, 113c), and the light-emitting colors of each light-emitting layer can be freely combined. For example, light-emitting layer 113a can be blue, light-emitting layer 113b can be red, green, or yellow, and light-emitting layer 113c can be blue. Alternatively, light-emitting layer 113a can be red, light-emitting layer 113b can be blue, green, or yellow, and light-emitting layer 113c can be red.

[0347] In the light-emitting device according to one aspect of the present invention described above, at least one of the first electrode 101 and the second electrode 102 is a light-transmitting electrode (such as a transparent electrode or a semi-transparent / semi-reflective electrode). If the light-transmitting electrode is a transparent electrode, the transmittance of visible light of the transparent electrode shall be 40% or more. If it is a semi-transparent / semi-reflective electrode, the reflectance of visible light of the semi-transparent / semi-reflective electrode shall be 20% or more and 80% or less, preferably 40% or more and 70% or less. Furthermore, the resistivity of these electrodes shall be 1 × 10⁻⁶. -2 It is preferable to keep it below Ωcm.

[0348] Furthermore, in the light-emitting device according to one aspect of the present invention described above, if one of the first electrode 101 and the second electrode 102 is a reflective electrode (reflective electrode), the visible light reflectance of the reflective electrode is 40% or more and 100% or less, preferably 70% or more and 100% or less. In addition, the resistivity of this electrode is 1 × 10⁻⁶. -2 It is preferable to keep it below Ωcm.

[0349] ≪Specific structure of a light-emitting device≫ Next, a specific structure of a light-emitting device according to one aspect of the present invention will be described. Here, we will use Figure 4(D), which has a tandem structure, for explanation. The same applies to the EL layer configuration for the single-structure light-emitting devices shown in Figures 4(A) and 4(C). Furthermore, if the light-emitting device shown in Figure 4(D) has a microcavity structure, the first electrode 101 is formed as a reflective electrode, and the second electrode 102 is formed as a semi-transparent / semi-reflective electrode. Thus, one or more desired electrode materials can be used and formed in a single layer or in a stacked manner. The second electrode 102 is formed after the EL layer 103b is formed, by selecting a material in the same manner as described above.

[0350] <First electrode and second electrode> As materials for forming the first electrode 101 and the second electrode 102, any combination of the following materials can be used as long as the functions of both electrodes described above are met. For example, metals, alloys, electrically conductive compounds, and mixtures thereof can be used as appropriate. Specifically, these include In-Sn oxide (also called ITO), In-Si-Sn oxide (also called ITSO), In-Zn oxide, and In-W-Zn oxide. In addition, metals such as aluminum (Al), titanium (Ti), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), gallium (Ga), zinc (Zn), indium (In), tin (Sn), molybdenum (Mo), tantalum (Ta), tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium (Y), neodymium (Nd), and alloys containing these in appropriate combinations can also be used. In addition, elements belonging to Group 1 or Group 2 of the periodic table not exemplified above (for example, lithium (Li), cesium (Cs), calcium (Ca), strontium (Sr)), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these in appropriate combinations, as well as graphene and other materials can be used.

[0351] In the light-emitting device shown in Figure 4(D), when the first electrode 101 is the anode, the hole injection layer 111a and hole transport layer 112a of the EL layer 103a are sequentially laminated on the first electrode 101 by vacuum deposition. After the EL layer 103a and charge generation layer 106 are formed, the hole injection layer 111b and hole transport layer 112b of the EL layer 103b are similarly sequentially laminated on the charge generation layer 106.

[0352] <Hole injection layer> The hole injection layers (111, 111a, 111b) are layers that inject holes from the first electrode 101, which is the anode, or from the charge generation layers (106, 106a, 106b) into the EL layers (103, 103a, 103b), and are layers containing organic acceptor material or a material with high hole injection potential.

[0353] Organic acceptor materials are materials that can generate holes in an organic compound by separating its charge from other organic compounds whose LUMO level and HOMO level are close in value. Therefore, compounds having electron-withdrawing groups (halogen groups or cyano groups), such as quinodimethane derivatives, chloranil derivatives, or hexaazatriphenylene derivatives, can be used as organic acceptor materials. For example, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviated as 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-hexazatriphenylene (abbreviated as HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviated as F6-TCNNQ), 2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyrene-2-ylidene)malononitrile, etc. can be used. Furthermore, among organic acceptor materials, compounds in which an electron-withdrawing group is bonded to a condensed aromatic ring having multiple heteroatoms, such as HAT-CN, are particularly suitable because they have high acceptability and stable film properties with respect to heat. In addition, radialene derivatives having an electron-withdrawing group (especially a halogen group such as a fluoro group, or a cyano group) [3] are also preferred because they have very high electron-accepting properties. Specifically, α,α',α''-1,2,3-cyclopropanetriylidenates[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidenates[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], and α,α',α''-1,2,3-cyclopropanetriylidenates[2,3,4,5,6-pentafluorobenzeneacetonitrile] can be used.

[0354] Furthermore, as materials with high hole injection potential, oxides of metals belonging to groups 4 through 8 of the periodic table (such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, and other transition metal oxides) can be used. Specifically, examples include molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, and rhenium oxide. Among these, molybdenum oxide is preferred because it is stable in the atmosphere, has low hygroscopicity, and is easy to handle. In addition, phthalocyanine compounds such as phthalocyanine (abbreviated as H2Pc) or copper phthalocyanine (abbreviated as CuPc) can be used.

[0355] In addition to the above materials, the low molecular weight compounds 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 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: DNTPD), 1,3,5- Aromatic amine compounds such as tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) can be used.

[0356] Furthermore, polymer compounds (oligomers, dendrimers, polymers, etc.) such as poly(N-vinylcarbazole) (abbreviated as PVK), poly(4-vinyltriphenylamine) (abbreviated as PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD) can be used. Alternatively, polymer compounds to which acids such as poly(3,4-ethylenedioxythiophene) / polystyrene sulfonic acid (abbreviated as PEDOT / PSS) and polyaniline / polystyrene sulfonic acid (PAni / PSS) have been added can also be used.

[0357] Furthermore, as a material with high hole injection capabilities, a mixed material containing a hole transport material and the aforementioned organic acceptor material (electron-accepting material) can also be used. In this case, electrons are extracted from the hole transport material by the organic acceptor material, generating holes in the hole injection layer 111, and these holes are injected into the light-emitting layer 113 via the hole transport layer 112. The hole injection layer 111 may be formed as a single layer of a mixed material containing a hole transport material and an organic acceptor material (electron-accepting material), or it may be formed by laminating the hole transport material and the organic acceptor material (electron-accepting material) in separate layers.

[0358] Furthermore, for hole-transporting materials, the hole mobility at which the square root of the electric field strength [V / cm] is 600 is 1 × 10⁻⁶. -6 cm 2 A material having a hole mobility of / Vs or higher is preferred. However, any material that has higher hole transport than electron transport can be used.

[0359] Furthermore, as hole-transporting materials, materials with high hole-transporting properties such as compounds having a π-electron-rich heteroaromatic ring (e.g., carbazole derivatives, furan derivatives, or thiophene derivatives) or aromatic amines (organic compounds having an aromatic amine skeleton) are preferred.

[0360] Examples of the above-mentioned carbazole derivatives (organic compounds having a carbazole ring) include bicarbazole derivatives (for example, 3,3'-bicarbazole derivatives) and aromatic amines having a carbazolyl group.

[0361] Furthermore, specific examples of the above-mentioned bicarbazole derivatives (for example, 3,3'-bicarbazole derivatives) include 3,3'-bis(9-phenyl-9H-carbazole) (abbreviated as PCCP), 9,9'-bis(biphenyl-4-yl)-3,3'-bi-9H-carbazole (abbreviated as BisBPCz), 9,9'-bis(1,1'-biphenyl-3-yl)-3,3'-bi-9H-carbazole (abbreviated as BismBPCz), 9-(1,1'-biphenyl-3-yl)-9'-(1,1'-biphenyl-4-yl)-9H,9'H-3,3'-bicarbazole (abbreviated as mBPCCBP), and 9-(2-naphthyl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviated as βNCCP).

[0362] Furthermore, examples of aromatic amines having the above-mentioned carbazolyl group include 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCBA1BP), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazole-3-amine (abbreviated as PCBiF), and N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3- [9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazole-3-yl) Diphenylamine (abbreviation: PCBNBB), 4-phenyldiphenyl-(9-phenyl-9H-carbazole-3-yl)amine (abbreviation: PCA1BP), N,N'-bis(9-phenylcarbazole-3-yl)-N,N'-diphenylbenzene-1,3-diamine (abbreviation: PCA2B), N,N',N''-triphenyl-N,N',N''-tris(9-phenylcarbazole-3-yl)benzene-1,3,5-triamine (abbreviation: PCA3B), 9 ,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-Bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), 3,[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA1), 3,6-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA2), 3,6-Bis[N-(4-diphenylaminophenyl)-N-(1 Examples include -naphthyl)amino]-9-phenylcarbazole (abbreviation: PCzTPN2), 2-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: PCASF), N-[4-(9H-carbazole-9-yl)phenyl]-N-(4-phenyl)phenylaniline (abbreviation: YGA1BP), N,N'-bis[4-(carbazole-9-yl)phenyl]-N,N'-diphenyl-9,9-dimethylfluorene-2,7-diamine (abbreviation: YGA2F), and 4,4',4''-tris(carbazole-9-yl)triphenylamine (abbreviation: TCTA).

[0363] In addition to the above, other examples of carbazole derivatives include 3-[4-(9-phenanthryl)-phenyl]-9-phenyl-9H-carbazole (abbreviated as PCPPn), 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviated as PCPN), 1,3-bis(N-carbazolyl)benzene (abbreviated as mCP), 4,4'-di(N-carbazolyl)biphenyl (abbreviated as CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviated as CzTP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviated as TCPB), and 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as CzPA).

[0364] Furthermore, specific examples of the above-mentioned furan derivatives (organic compounds having a furan ring) include 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II) and 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II).

[0365] Furthermore, specific examples of the above-mentioned thiophene derivatives (organic compounds having a thiophene ring) include 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviated as DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviated as DBTFLP-III), and 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviated as DBTFLP-IV).

[0366] Furthermore, the above aromatic amines specifically include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as BPAFLP), 4 -phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), N-(4-biphenyl)-N-{4-[(9-phenyl)-9H-fluoren-9-yl]-phenyl}-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: FBiFLP), N,N,N',N'-tetrakis(4-biphenyl)-1,1-biphenyl-4,4'-diamine (abbreviation: BBA2BP), N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio[9H-fluoren]-4-amine N (abbreviation: SF4FAF), N-(9,9-dimethyl-9H-fluoren-2-yl)-N-{9,9-dimethyl-2-[N'-phenyl-N'-(9,9-dimethyl-9H-fluoren-2-yl)amino]-9H-fluoren-7-yl}phenylamine (abbreviation: DFLADFL), N-(9,9-dimethyl-2-diphenylamino-9H-fluoren-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-phenylamino]triphenylamine (abbreviation: m-MTDATA), N,N'-Di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), DNTPD, 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), N-(4-biphenyl)-6,N-diphenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BnfABP), N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (Abbreviation: BBABnf), 4,4'-bis(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)-4''-phenyltriphenylamine (Abbreviation: BnfBB1BP), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-6-amine (Abbreviation: BBABnf(6)), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8-amine (Abbreviation: BBABnf(8)), N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (Abbreviation: BBABnf(II)(4)) ), N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP), N-[4-(dibenzothiophen-4-yl)phenyl]-N-phenyl-4-biphenylamine (abbreviation: ThBA1BP), 4-(2-naphthyl)-4',4''-diphenyltriphenylamine (abbreviation: BBAβNB), 4-[4-(2-naphthyl)phenyl]-4',4''-diphenyltriphenylamine (abbreviation: BBAβNBi), 4,4'-diphenyl-4''-(6;1'-binaphthyl-2-yl)triphenyl Luamine (abbreviation: BBAαNβNB), 4,4'-diphenyl-4''-(7;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB-03), 4,4'-diphenyl-4''-(7-phenyl)naphthyl-2-yltriphenylamine (abbreviation: BBAPβNB-03), 4,4'-diphenyl-4''-(6;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B), 4,4'-diphenyl-4''-(7;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B-03), 4,4'-Diphenyl-4''-(4;2'-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB), 4,4'-Diphenyl-4''-(5;2'-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB-02), 4-(4-biphenylyl)-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: TPBiAβNB), 4-(3-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: mTPBiAβNBi), 4-(4- Biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: TPBiAβNBi), 4-phenyl-4'-(1-naphthyl)triphenylamine (abbreviation: αNBA1BP), 4,4'-bis(1-naphthyl)triphenylamine (abbreviation: αNBB1BP), 4,4'-diphenyl-4''-[4'-(carbazole-9-yl)biphenyl-4-yl]triphenylamine (abbreviation: YGTBi1BP), 4'-[4-(3-phenyl-9H-carbazole-9-yl)phenyl]tri Su(1,1'-biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02), 4-[4'-(carbazole-9-yl)biphenyl-4-yl]-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: YGTBiβNB), bis-biphenyl-4'-(carbazole-9-yl)biphenylamine (abbreviation: YGBBi1BP), N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation) Name: PCBNBSF), N,N-bis([1,1'-biphenyl]-4-yl)-9,9'-spirobio[9H-fluorene]-2-amine (abbreviation: BBASF), N,N-bis([1,1'-biphenyl]-4-yl)-9,9'-spirobio[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobio[9H-fluorene]-4-amine (abbreviation: oFBiSF), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzofuran-4-amine (abbreviation: FrBiF), N-[4-(1-naphthyl)phenyl]-N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthylamine (abbreviation: mPDBfBNBN), 4-phenyl-4'-[4-(9-phenylfluoren-9-yl)phenyl]triphenylamine (abbreviation: BPAFLBi), N,N-bis(9,9-dimethyl-9H-fluoren-2- Examples include N,N-bis(9,9-dimethyl-9H-fluoren-4-amine), N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-3-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-2-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-1-amine, etc.

[0367] In addition, polymer compounds (oligomers, dendrimers, polymers, etc.) such as poly(N-vinylcarbazole) (abbreviated as PVK), poly(4-vinyltriphenylamine) (abbreviated as PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD) can be used as hole transport materials. Alternatively, polymer compounds to which acids such as poly(3,4-ethylenedioxythiophene) / polystyrene sulfonic acid (abbreviated as PEDOT / PSS) and polyaniline / polystyrene sulfonic acid (PAni / PSS) have been added can also be used.

[0368] However, the hole transport material is not limited to the above, and various known materials may be used as a hole transport material by combining one or more of them.

[0369] The hole injection layers (111, 111a, 111b) can be formed using various known film deposition methods, for example, by vacuum deposition.

[0370] <Hole transport layer> The hole transport layers (112, 112a, 112b) are layers that transport holes injected from the first electrode 101 by the hole injection layers (111, 111a, 111b) to the light-emitting layers (113, 113a, 113b). The hole transport layers (112, 112a, 112b) are layers containing a hole-transporting material. Therefore, the hole transport layers (112, 112a, 112b) can use the same hole-transporting material that can be used in the hole injection layers (111, 111a, 111b).

[0371] In one embodiment of the present invention, the same organic compound used in the hole transport layer (112, 112a, 112b) can be used in the light-emitting layer (113, 113a, 113b). Using the same organic compound in both the hole transport layer (112, 112a, 112b) and the light-emitting layer (113, 113a, 113b) is preferable because it allows for more efficient transport of holes from the hole transport layer (112, 112a, 112b) to the light-emitting layer (113, 113a, 113b).

[0372] <Luminous layer> The light-emitting layers (113, 113a, 113b) are layers containing a light-emitting material. The light-emitting material that can be used in the light-emitting layers (113, 113a, 113b) can be any material that exhibits a light-emitting color such as blue, purple, blue-violet, green, yellow-green, yellow, orange, or red. Furthermore, if there are multiple light-emitting layers, a configuration exhibiting different light-emitting colors can be achieved by using different light-emitting materials in each layer (for example, white light emission obtained by combining complementary light-emitting colors). Additionally, a laminated structure in which each light-emitting layer contains a different light-emitting material is also possible.

[0373] Furthermore, the light-emitting layers (113, 113a, 113b) may contain one or more types of organic compounds (host materials, etc.) in addition to the light-emitting substance (guest material).

[0374] Furthermore, when multiple host materials are used in the light-emitting layers (113, 113a, 113b), it is preferable to use a material with a larger energy gap than the energy gaps of the existing guest material and the first host material as the newly added second host material. It is also preferable that the lowest singlet excitation energy level (S1 level) of the second host material is higher than the S1 level of the first host material, and that the lowest triplet excitation energy level (T1 level) of the second host material is higher than the T1 level of the guest material. Furthermore, it is preferable that the lowest triplet excitation energy level (T1 level) of the second host material is higher than the T1 level of the first host material. With this configuration, an excitation complex can be formed using two types of host materials. In order to efficiently form the excitation complex, it is particularly preferable to combine a compound that readily accepts holes (hole transport material) with a compound that readily accepts electrons (electron transport material). This configuration also enables the simultaneous achievement of high efficiency, low voltage, and long lifespan.

[0375] The organic compounds used as the host material (including the first and second host materials) can be hole-transporting materials that can be used in the aforementioned hole-transporting layers (112, 112a, 112b), or electron-transporting materials that can be used in the electron-transporting layers (114, 114a, 114b) described later, as long as they satisfy the conditions for being a host material used in the light-emitting layer. An excited complex composed of multiple types of organic compounds (the first and second host materials) may also be used. An excited complex (also called an exciplex) that forms an excited state with multiple types of organic compounds has an extremely small difference between the S1 and T1 levels and functions as a TADF material that can convert triplet excitation energy into singlet excitation energy. Furthermore, as a combination of multiple types of organic compounds that form an excited complex, for example, it is preferable that one has a π-electron-deficient heteroaromatic ring and the other has a π-electron-rich heteroaromatic ring. Furthermore, as a combination for forming the excitation complex, one of the components may be a phosphorescent material such as an iridium, rhodium, or platinum-based organometallic complex, or a metal complex.

[0376] There are no particular limitations on the luminescent material that can be used in the luminescent layers (113, 113a, 113b). A luminescent material that converts singlet excitation energy into visible light emission, or a luminescent material that converts triplet excitation energy into visible light emission, can be used.

[0377] <<Luminescent material that converts singlet excitation energy into light emission>> Examples of luminescent materials that can be used in the light-emitting layers (113, 113a, 113b) to convert singlet excitation energy into light include the following fluorescent materials (fluorescent materials). For example, pyrene derivatives, anthracene derivatives, triphenylene derivatives, fluorene derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, dibenzoquinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives, phenanthrene derivatives, and naphthalene derivatives are examples. Pyrene derivatives are particularly preferred because they 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: 1,6FrAPrn), N,N'-bis(dibenzothiophen-2-yl)-N, Examples include N'-diphenylpyrene-1,6-diamine (abbreviation: 1,6ThAPrn), N,N'-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-6-amine] (abbreviation: 1,6BnfAPrn), N,N'-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-02), and N,N'-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03).

[0378] Also, 5,6-bis[4-(10-phenyl-9-antryl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-antryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazole (9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazole-9-yl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), 4-(10-phenyl-9-anthryl)-4'- (9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBAPA), 4-[4-(10-phenyl-9-antryl)phenyl]-4'-(9-phenyl-9H-carbazole-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) Nilen)bis[N,N',N'-triphenyl-1,4-phenylenediamine] (abbreviated as DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazole-3-amine (abbreviated as 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPAPPA), etc. can be used.

[0379] Also, N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10-bis(1,1'-biphenyl -2-yl)-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracene-9-amine (abbreviation: DPhAPhA), coumarin 545T, N,N'-diphenylquinacridone (abbreviation: DPQd), rubren, 5,12-bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BPT), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl-4H-pyran-4-yl DCM1)propanedinitrile, 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoridine-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (DCM2), N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluorantene-3,10-diamine (p -mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoridine-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoridine-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTB), 2-(2,6-Bis{2-[4-(dimethylamino)phenyl]ethenyl}-4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2,6-Bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoridine-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: BisDCJTM), 1,6BnfAP Examples include rn-03, 3,10-bis[N-(9-phenyl-9H-carbazole-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV)-02), and 3,10-bis[N-(dibenzofuran-3-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10FrA2Nbf(IV)-02). In particular, pyrenediamine compounds such as 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03 can be used.

[0380] <<Luminescent material that converts triplet excitation energy into light emission>> Next, examples of luminescent materials that can be used in the luminescent layers (113, 113a, 113b) to convert triplet excitation energy into luminescence include phosphorescent materials (phosphorescent materials) or thermally activated delayed fluorescence (TADF) materials that exhibit thermally activated delayed fluorescence.

[0381] A phosphorescent material is a compound that exhibits phosphorescence and does not fluoresce at any temperature range above low temperatures (e.g., 77K) and below room temperature (i.e., between 77K and 313K). The phosphorescent material preferably contains a metal element with strong spin-orbit interaction, and examples include organometallic complexes, metal complexes (platinum complexes), and rare earth metal complexes. Specifically, transition metal elements are preferred, and particularly platinum group elements (ruthenium (Ru), rhodium (Rh), palladium (Pd), osmium (Os), iridium (Ir), or platinum (Pt)) are preferred. The presence of iridium is especially preferable because it increases the transition probability involved in the direct transition between the singlet ground state and the triplet excited state.

[0382] ≪Phosphorescent materials (450nm to 570nm: blue or green)≫ Examples of phosphorescent materials that exhibit blue or green light and have a peak wavelength of emission spectrum between 450 nm and 570 nm include the following:

[0383] 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-4H-1,2,4-triazolato] iridium(III) (abbreviation: [Ir(iPrptz-3b)3]), tris[3-(5-biphenyl)-5-isopropyl-4-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPr5btz)3]), organometallic complexes having a 4H-triazole ring, such as tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz1-mp)3]), tris(1- Organometallic complexes having a 1H-triazole ring, such as methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me)3]), fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpmi)3]), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenantridinato]iridium(II) Organometallic complexes having an imidazole ring, such as I) (abbreviation: [Ir(dmpimpt-Me)3]), bis[2-(4',6'-difluorophenyl)pyridinate-N,C2']iridium(III)tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinate-N,C2']iridium(III)picolinate (abbreviation: FIrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinate-N,C 2’ Iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyridinate-N,C 2’Examples include organometallic complexes that use phenylpyridine derivatives having electron-withdrawing groups as ligands, such as iridium(III) acetylacetonate (abbreviated as Fir(acac)).

[0384] ≪Phosphorescent materials (495nm to 590nm: green or yellow)≫ Examples of phosphorescent materials that exhibit a green or yellow color and have a peak wavelength of emission spectrum between 495 nm and 590 nm include the following:

[0385] For example, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bis(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)2(acac)]), (acetylacetonato)bis(6-tert- (Ir(tBuppm)2(acac)), (acetylacetonato)bis[6-(2-norbornyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]), (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm Organometallic iridium(III) having a pyrimidine ring, such as (acetylacetonato)bis{4,6-dimethyl-2-[6-(2,6-dimethylphenyl)-4-pyrimidinyl-κN3]phenyl-κC}iridium(III) (abbreviation: [Ir(dmppm-dmp)2(acac)]), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2(acac)]), iridium complexes having a pyrazine ring, such as (acetylacetonato)bis(3,5-dimethyl-2-phenylpyradinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac)]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyradinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]), and tris(2-phenylpyridinato-N,C) 2’ Iridium(III) (abbreviation: [Ir(ppy)3]), bis(2-phenylpyridinate-N,C) 2’Iridium(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), bis(benzo[h]quinolinate)iridium(III) acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), tris(benzo[h]quinolinate)iridium(III) (abbreviation: [Ir(bzq)3]), tris(2-phenylquinolinate-N,C) 2’ Iridium(III) (abbreviation: [Ir(pq)3]), bis(2-phenylquinolinato-N,C) 2’ Iridium(III) acetylacetonate (abbreviation: [Ir(pq)2(acac)]), bis[2-(2-pyridinyl-κN)phenyl-κC][2-(4-phenyl-2-pyridinyl-κN)phenyl-κC] Iridium(III) (abbreviation: [Ir(ppy)2(4dppy)]), bis[2-(2-pyridinyl-κN)phenyl-κC][2-(4-methyl-5-phenyl-2-pyridinyl {2-(methyl-d3)-8-[4-(1-methylethyl-1-d)-2-pyridinyl-κN]benzofloxacin [2,3-b]pyridinyl-κC]bis[2-(5-d3)-2-pyridinyl-κN2)phenyl-κC]iridium(III) (abbreviation: Ir(5mppy-d3)2(mbfpypy-d3)), {2-(methyl-d3)-8-[4-(1-methylethyl-1-d)-2-pyridinyl-κN]benzofloxacin [2,3-b]pyridinyl-7-yl-κC}bis{5-(methyl-d3)-2-[5-(methyl-d3)-2-pyridinyl-κN]phenyl-κC}iridium(III) (abbreviation: Ir(5mtpy-d6)2(mbfpypy-iPr-d4)), [2-d3-methyl-(2-pyridinyl-κN)benzoflofro[2,3-b]pyridinyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κC Organometallic iridium complexes having a pyridine ring, such as iridium(III) (abbreviation: Ir(ppy)2(mbfpypy-d3)), [2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(ppy)2(mdppy)), and bis(2,4-diphenyl-1,3-oxazolato-N,C 2’Iridium(III) acetylacetonate (abbreviation: [Ir(dpo)2(acac)]), bis{2-[4'-(perfluorophenyl)phenyl]pyridinate-N,C 2’ Iridium(III) acetylacetonate (abbreviation: [Ir(p-PF-ph)2(acac)]), bis(2-phenylbenzothiazolat-N,C) 2’ Examples include organometallic complexes such as iridium(III) acetylacetonate (abbreviated as [Ir(bt)2(acac)]), as well as rare earth metal complexes such as tris(acetylacetonate)(monophenanthroline)terbium(III) (abbreviated as [Tb(acac)3(Phen)]).

[0386] ≪Phosphorescent materials (570nm to 750nm: yellow or red)≫ Examples of phosphorescent materials that exhibit a yellow or red color and have a peak wavelength of emission spectrum between 570 nm and 750 nm include the following:

[0387] For example, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), (dipivaloylmethanato)bis[4,6-di(naphthalene-1-yl)pyrimidinato]iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]), and other pyramidal compounds. Organometallic complexes having a limidine ring: (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr)2(dpm)]), bis{4,6-dimethyl-2-[3-(3,5-dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-heptanedionato-κ 2O,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-pyradinyl-κN]phenyl-κC}(2,2,6,6-tetramethyl-3,5-heptanedionato-κ 2 O,O') Iridium(III) (abbreviation: [Ir(dmdppr-dmCP)2(dpm)]), bis{2-[5-(2,6-dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]-4,6-dimethylphenyl-κC}(2,2',6,6'-tetramethyl-3,5-heptanedionato-κ2O,O') Iridium(III) (abbreviation: [Ir(dmdppr-dmp)2(dpm)]), (acetylacetonato)bis[2-methyl-3-phenylquinoxalinato-N,C 2’ Iridium(III) (abbreviation: [Ir(mpq)2(acac)]), (acetylacetonato)bis(2,3-diphenylquinoxalinato-N,C) 2’ Organometallic complexes having a pyrazine ring, such as iridium(III) (abbreviation: [Ir(dpq)2(acac)]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]), and tris(1-phenylisoquinolinato-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-quinolinyl-κN)phenyl-κC](2,4-pentanedionato-κ 2Examples include organometallic complexes having a pyridine ring, such as O,O')iridium(III) (abbreviation: [Ir(dmpqn)2(acac)]), platinum complexes such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: [PtOEP]), or rare earth metal complexes such as tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: [Eu(DBM)3(Phen)]) and tris[1-(2-tenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: [Eu(TTA)3(Phen)]).

[0388] ≪TADF material≫ Furthermore, the following materials can be used as TADF materials. A TADF material is a material in which the difference between the S1 level and the T1 level is small (preferably 0.2 eV or less), the triplet excited state can be upconverted to the singlet excited state with a small amount of thermal energy (reverse intersystem crossing), and the emission (fluorescence) from the singlet excited state is efficiently exhibited. Furthermore, conditions for efficiently obtaining thermally activated delayed fluorescence include an energy difference between the triplet excited energy level and the singlet excited energy level being 0 eV or more and 0.2 eV or less, preferably 0 eV or more and 0.1 eV or less. In addition, delayed fluorescence in TADF materials refers to emission that has a spectrum similar to normal fluorescence but with a remarkably long lifetime. Its lifetime is 1 × 10⁻⁶ -6 For more than a second, preferably 1 × 10⁻⁶ seconds. -3 It is more than a second.

[0389] Examples of TADF materials include fullerenes or their derivatives, acridine derivatives such as proflavin, and eosin. Also, metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd) are also examples. Examples of metal-containing porphyrins include protoporphyrin-tin fluoride complexes (abbreviated as SnF2(Proto IX)), mesoporphyrin-tin fluoride complexes (abbreviated as SnF2(Meso IX)), hematoporphyrin-tin fluoride complexes (abbreviated as SnF2(Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complexes (abbreviated as SnF2(Copro III-4Me)), octaethylporphyrin-tin fluoride complexes (abbreviated as SnF2(OEP)), etioporphyrin-tin fluoride complexes (abbreviated as SnF2(Etio I)), and octaethylporphyrin-platinum chloride complexes (abbreviated as PtCl2OEP).

[0390] [ka]

[0391] Other examples include 2-(biphenyl-4-yl)-4,6-bis(12-phenylindoro[2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviated as PIC-TRZ), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviated as PCCzPTzn), and 2-[4-(10H-phenoxy [Sadin-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4-(5-phenyl-5,10-dihydrophenazine-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimethyl-9H-acridine-10-yl)-9H-xanthene-9-one (abbreviation: ACRXTN), bis[4-(9, 9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10'H-spiro[acridine-9,9'-anthracene]-10'-one (abbreviation: ACRSA), 4-(9'-phenyl-3,3'-bi-9H-carbazole-9-yl)benzoflo[3,2-d]pyrimidine (abbreviation: 4PCCzBfpm), 4-[4-(9'-phenyl-3,3'- Hetero-aromatic compounds having π-electron-rich hetero-aromatic compounds and π-electron-deficient hetero-aromatic compounds such as bi-9H-carbazole-9-yl)phenyl]benzofl[3,2-d]pyrimidine (abbreviation: 4PCCzPBfpm) and 9-[3-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02) may also be used.

[0392] Furthermore, a material in which a π-electron-rich heteroaromatic compound and a π-electron-deficient heteroaromatic compound are directly bonded is particularly preferable because both the donor properties of the π-electron-rich heteroaromatic compound and the acceptor properties of the π-electron-deficient heteroaromatic compound become stronger, and the energy difference between the singlet excited state and the triplet excited state becomes smaller. In addition, a TADF material (TADF100) in which the singlet excited state and the triplet excited state are in thermal equilibrium may be used as the TADF material. Since such a TADF material has a shorter luminescence lifetime (excitation lifetime), it is possible to suppress the decrease in efficiency in the high-brightness region of the light-emitting element.

[0393] [ka]

[0394] In addition to the above, other materials that have the function of converting triplet excitation energy into light emission include nanostructures of transition metal compounds having a perovskite structure. Nanostructures of metal halogen perovskites are particularly desirable. Nanoparticles and nanorods are preferred as such nanostructures.

[0395] In the light-emitting layers (113, 113a, 113b, 113c), the organic compounds (host materials, etc.) used in combination with the light-emitting material (guest material) described above may be one or more materials having an energy gap larger than the energy gap of the light-emitting material (guest material).

[0396] ≪Host materials for fluorescence emission≫ When the light-emitting material used in the light-emitting layer (113, 113a, 113b, 113c) is a fluorescent light-emitting material, it is preferable to use an organic compound (host material) that has a large singlet excited state energy level and a small triplet excited state energy level, or an organic compound with a high fluorescence quantum yield. Therefore, any organic compound that satisfies these conditions can be used, such as the hole transport material (described above) or electron transport material (described below) shown in this embodiment.

[0397] Although some of these overlap with the specific examples mentioned above, from the perspective of preferred combinations with luminescent substances (fluorescent substances), examples of organic compounds (host materials) include condensed polycyclic aromatic compounds such as anthracene derivatives, tetracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, and dibenzo[g,p]chrysene derivatives.

[0398] Specific examples of organic compounds (host materials) that are preferable to use in combination with fluorescent luminescent substances include 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviated as PCzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviated as DPCzPA), 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviated as PCPN), 9,10-diphenylanthracene (abbreviated as DPAnth), and N,N-diphenyl Nyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), YGAPA, PCAPA, N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), 6,12-Dimethoxy-5,11-Diphenylchrysene, N,N,N',N',N'',N'',N''',N'''-Octaphenyldibenzo[g,p]chrysene-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]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]- Nzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-[4-(9-phenyl-9H-fluoren-9-yl)-biphenyl-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-(1-naphthyl)-10-(2-naphthyl)anthracene (abbreviation: α,βADN), 2-(10-phenylanthracene-9-yl)dibenzofuran, 2-(10-phenyl-9-anthracenyl)-benzo[b]naphtho[2,3-d]furan (abbreviation: Bnf(II)PhA), 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth), 9-(2-naphthyl)-10-[3-(2-naphthyl)phenyl]anthracene (abbreviation: βN-mβNPAnth), 1-[4-(10-[1,1'-biphenyl]-4-yl-9- Examples include anthracenyl)phenyl]-2-ethyl-1H-benzimidazole (abbreviation: EtBImPBPhA), 9,9'-biantryl (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-diphenyltetracene, and 5,12-bis(biphenyl-2-yl)tetracene.

[0399] ≪Host materials for phosphorescence≫ Furthermore, when the luminescent material used in the luminescent layers (113, 113a, 113b, 113c) is a phosphorescent material, it is sufficient to select an organic compound (host material) to combine with it that has a triplet excitation energy greater than the triplet excitation energy of the luminescent material (the energy difference between the ground state and the triplet excited state). When using multiple organic compounds (for example, a first host material and a second host material (or assist material), etc.) in combination with the luminescent material to form an excited complex, it is preferable to mix these multiple organic compounds with the phosphorescent material.

[0400] This configuration allows for efficient emission using ExTET (Exciplex-Triplet Energy Transfer), which is energy transfer from the excited complex to the luminescent material. The combination of organic compounds should ideally be one that readily forms an excited complex, and a combination of a compound that readily accepts holes (hole transport material) and a compound that readily accepts electrons (electron transport material) is particularly preferable.

[0401] In addition, although some of these examples overlap with those mentioned above, from the perspective of preferred combinations with luminescent substances (phosphorescent substances), suitable organic compounds (host materials, assist materials) include aromatic amines (organic compounds having an aromatic amine skeleton), carbazole derivatives (organic compounds having a carbazole ring), dibenzothiophene derivatives (organic compounds having a dibenzothiophene ring), dibenzofuran derivatives (organic compounds having a dibenzofuran ring), oxadiazole derivatives (organic compounds having an oxadiazole ring), triazole derivatives (organic compounds having a triazole ring), and benzimidazole derivatives (benzimi Examples include organic compounds having a dazole ring, quinoxaline derivatives (organic compounds having a quinoxaline ring), dibenzoquinoxaline derivatives (organic compounds having a dibenzoquinoxaline ring), pyrimidine derivatives (organic compounds having a pyrimidine ring), triazine derivatives (organic compounds having a triazine ring), pyridine derivatives (organic compounds having a pyridine ring), bipyridine derivatives (organic compounds having a bipyridine ring), phenanthroline derivatives (organic compounds having a phenanthroline ring), phlodiazine derivatives (organic compounds having a phlodiazine ring), zinc-based or aluminum-based metal complexes, etc.

[0402] Furthermore, among the above-mentioned organic compounds, specific examples of aromatic amines and carbazole derivatives, which are organic compounds with high hole transport properties, are the same as the specific examples of hole transport materials described above, and all of these are preferred as host materials.

[0403] Furthermore, among the above organic compounds, specific examples of dibenzothiophene derivatives and dibenzofuran derivatives, which are organic compounds with high hole transport properties, include 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II), 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), DBT3P-II, and 2,8-diphenyl Examples include nyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviated as DBTFLP-III), 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviated as DBTFLP-IV), and 4-[3-(triphenylene-2-yl)phenyl]dibenzothiophene (abbreviated as mDBTPTp-II), all of which are preferred as host materials.

[0404] Other preferred host materials include metal complexes having oxazole-based or thiazole ligands such as bis[2-(2-benzoxazolyl)phenolate]zinc(II) (abbreviated as ZnPBO) and bis[2-(2-benzothiazolyl)phenolate]zinc(II) (abbreviated as ZnBTZ).

[0405] Furthermore, among the above organic compounds, specific examples of organic compounds with high electron transport properties, such as oxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, quinazoline derivatives, and phenanthroline derivatives, include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), and 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), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), 4,4'-bis(5- Organic compounds containing heteroaromatic rings with polyazole rings, such as tylbenzoxazole-2-yl)stilbene (abbreviation: BzOs), vasophenanthroline (abbreviation: Bphen), vasocuproin (abbreviation: BCP), 2,9-di(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen), 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] (abbreviation: mPPhen2P), 2,2'-(1,1'-biphenyl)-3,3'-diylbis(9-phenyl-1,1 Organic compounds containing a heteroaromatic ring with a pyridine ring, such as 0-phenanthroline (abbreviation: PPhen2BP), 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3-(3'-dibenzothiophen-4-yl)biphenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazole-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4-(3,6-Diphenyl-9H-carbazole-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II), and 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDB Examples include q-II), 2-{4-[9,10-di(2-naphthyl)-2-anthryl]phenyl}-1-phenyl-1H-benzimidazole (abbreviated as ZADN), 2-[4'-(9-phenyl-9H-carbazole-3-yl)-3,1'-biphenyl-1-yl]dibenzo[f,h]quinoxaline (abbreviated as 2mpPCBPDBq), and others, all of which are preferred as host materials.

[0406] Furthermore, among the above organic compounds, specific examples of organic compounds with high electron transport capabilities include pyridine derivatives, diazine derivatives (including pyrimidine derivatives, pyrazine derivatives, and pyridazine derivatives), triazine derivatives, and phlodiazine derivatives, such as 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), and 4,6-bis[3-(9H-carbazole-9-yl)phenyl]pyrimidine (abbreviation: (Abbreviation: 4,6mCzP2Pm), 2-{4-[3-(N-phenyl-9H-carbazol-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-carbazol (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), 9,9'-[pyrimidine-4,6-diylbis(biphenyl-3,3'-diyl)]bis(9H-carbazole) (abbreviation: 4,6mCzBP2Pm), 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)-1,1'-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn), 8-(1,1'-biphenyl-4-yl)-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofloxacin[3,2-d ]pyrimidine (abbreviation: 8BP-4mDBtPBfpm), 9-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]flo[2,3-b]pyrazine (abbreviation: 9mDBtBPNfpr), 9-[(3'-dibenzothiophen-4-yl)biphenyl-4-yl]naphtho[1',2':4,5]flo[2,3-b]pyrazine (abbreviation: 9pmDBtBPNfpr), 5-[3-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl]-7,7-dimethyl-5H,7H-indeno[2,1-b]carbazole (abbreviation: mINc(II)PTzn), 2-[3'-(triphenylene-2-yl)-1,1'-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mTpBPTzn), 2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-[9,9'-spirobio(9H-fluoren)-2-yl]- 1,3,5-triazine (abbreviation: BP-SFTzn), 2,6-bis(4-naphthalene-1-ylphenyl)-4-[4-(3-pyridyl)phenyl]pyrimidine (abbreviation: 2,4NP-6PyPPm), 3-[9-(4,6-diphenyl-1,3,5-triazine-2-yl)-2-dibenzofuranyl]-9-phenyl-9H-carbazole (abbreviation: PCD) Examples include organic compounds containing heteroaromatic rings having a diazine ring, such as BfTzn, 2-[1,1'-biphenyl]-3-yl-4-phenyl-6-(8-[1,1':4',1''-terphenyl]-4-yl-1-dibenzofuranyl)-1,3,5-triazine (abbreviated as mBP-TPDBfTzn), 6-(1,1'-biphenyl-3-yl)-4-[3,5-bis(9H-carbazole-9-yl)phenyl]-2-phenylpyrimidine (abbreviated as 6mBP-4Cz2PPm), and 4-[3,5-bis(9H-carbazole-9-yl)phenyl]-2-phenyl-6-(1,1'-biphenyl-4-yl)pyrimidine (abbreviated as 6BP-4Cz2PPm), all of which are preferred as host materials.

[0407] Furthermore, among the above organic compounds, specific examples of metal complexes that are organic compounds with high electron transport properties include zinc-based or aluminum-based metal complexes such as tris(8-quinolinolato)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviated as BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviated as BAlq), bis(8-quinolinolato)zinc(II) (abbreviated as Znq), and metal complexes having a quinoline ring or a benzoquinoline ring, all of which are preferred as host materials.

[0408] Other polymer compounds such as poly(2,5-pyridinediyl) (abbreviated as PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py), and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy) are also preferred as host materials.

[0409] Furthermore, there are bipolar organic compounds that are highly hole-transporting and highly electron-transporting, such as 9-phenyl-9'-(4-phenyl-2-quinazolinyl)-3,3'-bi-9H-carbazole (abbreviation: PCCzQz), 2-[4'-(9-phenyl-9H-carbazole-3-yl)-3,1'-biphenyl-1-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mpPCBPDBq), and 5-[3-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl]-7,7-dimethyl-5H,7H-indeno[ Organic compounds having a diazine ring, such as 2,1-b]carbazole (abbreviation: mINc(II)PTzn), 11-[4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine-2-yl]-11,12-dihydro-12-phenylindoro[2,3-a]carbazole (abbreviation: BP-Icz(II)Tzn), and 7-[4-(9-phenyl-9H-carbazole-2-yl)quinazoline-2-yl]-7H-dibenzo[c,g]carbazole (abbreviation: PC-cgDBCzQz), can also be used as host materials.

[0410] <Electron transport layer> The electron transport layers (114, 114a, 114b) are layers that transport electrons injected from the second electrode 102 or the charge generation layer (106, 106a, 106b) by the electron injection layer (115, 115a, 115b), described later, to the light-emitting layer (113, 113a, 113b, 113c). Furthermore, the electron-transporting material used in the electron transport layers (114, 114a, 114b) has an electron mobility of 1 × 10⁻¹⁰ at an electric field strength [V / cm] square root of 600. -6 cm2 A material having an electron mobility of / Vs or higher is preferred. However, any material with higher electron transport capabilities than hole transport can be used. Furthermore, the electron transport layer (114, 114a, 114b) can function as a single layer, but it may also be a laminated structure of two or more layers. Since the above mixed material has heat resistance, performing the photolithography process on an electron transport layer using this material can suppress the influence of the thermal process on the device characteristics.

[0411] ≪Electron transport material≫ As electron-transporting materials that can be used in the electron transport layers (114, 114a, 114b), organic compounds with high electron transport properties can be used, for example, heteroaromatic compounds can be used. A heteroaromatic compound is a cyclic compound that contains at least two different elements in its ring. The ring structure can include 3-membered rings, 4-membered rings, 5-membered rings, 6-membered rings, etc., but 5-membered rings or 6-membered rings are particularly preferred, and heteroaromatic compounds that contain one or more of the elements carbon, nitrogen, oxygen, or sulfur are preferred. Nitrogen-containing heteroaromatic compounds (nitrogen-containing heteroaromatic compounds) are particularly preferred, and it is preferable to use materials with high electron transport properties (electron-transporting materials) such as nitrogen-containing heteroaromatic compounds or π-electron-deficient heteroaromatic compounds containing them.

[0412] Heteroaromatic compounds are organic compounds that have at least one heteroaromatic ring.

[0413] Furthermore, heteroaromatic rings contain one of the following: a pyridine ring, a diazine ring, a triazine ring, or a polyazole ring, an oxazole ring, or a thiazole ring. Heteroaromatic rings containing a diazine ring include heteroaromatic rings containing a pyrimidine ring, a pyrazine ring, or a pyridazine ring. Heteroaromatic rings containing a polyazole ring include heteroaromatic rings containing an imidazole ring, a triazole ring, or an oxadiazole ring.

[0414] Furthermore, heteroaromatic rings include fused heteroaromatic rings having a fused ring structure. Examples of fused heteroaromatic rings include quinoline rings, benzoquinoline rings, quinoxaline rings, dibenzoquinoxaline rings, quinazoline rings, benzoquinazoline rings, dibenzoquinazoline rings, phenanthroline rings, phlodiazine rings, and benzimidazole rings.

[0415] Examples of heteroaromatic compounds include, among heteroaromatic compounds containing one or more of nitrogen, oxygen, or sulfur in addition to carbon, heteroaromatic compounds having a five-membered ring structure such as heteroaromatic compounds having an imidazole ring, heteroaromatic compounds having a triazole ring, heteroaromatic compounds having an oxazole ring, heteroaromatic compounds having an oxadiazole ring, heteroaromatic compounds having a thiazole ring, and heteroaromatic compounds having a benzimidazole ring.

[0416] Furthermore, among heteroaromatic compounds that contain one or more elements other than carbon, such as nitrogen, oxygen, or sulfur, examples of heteroaromatic compounds having a six-membered ring structure include heteroaromatic compounds having heteroaromatic rings such as pyridine rings, diazine rings (including pyrimidine rings, pyrazine rings, pyridazine rings, etc.), triazine rings, and polyazole rings. Note that while heteroaromatic compounds with a structure in which pyridine rings are linked, examples include heteroaromatic compounds having a bipyridine structure and heteroaromatic compounds having a terpyridine structure.

[0417] Furthermore, examples of heteroaromatic compounds having a fused ring structure that partially includes the above-mentioned six-membered ring structure include heteroaromatic compounds having fused heteroaromatic rings such as quinoline rings, benzoquinoline rings, quinoxaline rings, dibenzoquinoxaline rings, phenanthroline rings, phlodiazine rings (including structures in which an aromatic ring is fused to the furan ring of a phlodiazine ring), and benzimidazole rings.

[0418] Specific examples of heteroaromatic compounds having the above-mentioned five-membered ring structure (polyazole ring (including imidazole ring, triazole ring, oxadiazole ring), oxazole ring, thiazole ring, benzimidazole ring, etc.) include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazole-2-yl)phenyl]-9H-carbazole (abbreviated as CO11), and 3-(4-biphenylyl)-4-phenyl Examples include phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviated as TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviated as mDBTBIm-II), and 4,4'-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviated as BzOs).

[0419] Specific examples of heteroaromatic compounds having the above-mentioned six-membered ring structure (including heteroaromatic rings having pyridine rings, diazine rings, triazine rings, etc.) include heteroaromatic compounds containing a pyridine ring, such as 3,5-bis[3-(9H-carbazole-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy) and 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), and 2-{4-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}-4,6-diphenyl-1,3,5 - Triazine (abbreviation: PCCzPTzn), 9-[3-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), 5-[3-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl]-7,7-dimethyl-5H,7H-indeno[2,1-b]carbazole (abbreviation: mINc(II)PTzn), 2-[3'-(triphenylene-2-yl)-1,1'-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (Abbreviation: mTpBPTzn), 2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-[9,9'-spirobi(9H-fluorene)-2-yl]-1,3,5-triazine (Abbreviation: BP-SFTzn), 2,6-bis(4-naphthalene-1-ylphenyl)-4-[4-(3-pyridyl)phenyl]pyrimidine (Abbreviation: 2,4NP-6PyPPm), 3-[9-(4,6-diphenyl-1,3,5-triazine-2-yl)-2-dibenzofuranyl]-9-phenyl-9H-carbazole (Abbreviation: PCDBfTzn), 2-[1,1'-bi Heteroaromatic compounds containing heteroaromatic rings having a triazine ring, such as phenyl]-3-yl-4-phenyl-6-(8-[1,1':4',1''-terphenyl]-4-yl-1-dibenzofuranyl)-1,3,5-triazine (abbreviation: mBP-TPDBfTzn), 2-{3-[3-(dibenzothiophen-4-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mDBtBPTzn), mFBPTzn, 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-Bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-Bis[3-(9H-carbazole-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), 4,6mCzBP2Pm, 6-(1,1'-biphenyl-3-yl)-4-[3,5-bis(9H-carbazole-9-yl)phenyl]-2-phenylpyrimidine (abbreviation: 6mBP-4Cz2 PPm), 4-[3,5-bis(9H-carbazole-9-yl)phenyl]-2-phenyl-6-(1,1'-biphenyl-4-yl)pyrimidine (abbreviation: 6BP-4Cz2PPm), 4-[3-(dibenzothiophen-4-yl)phenyl]-8-(naphthalene-2-yl)-[1]benzoflo[3,2-d]pyrimidine (abbreviation: 8βN-4mDBtPBfpm), 8BP-4mDBtPBfpm, 9mDBtBP Nfpr, 9pmDBtBPNfpr, 3,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzoflo[2,3-b]pyrazine (abbreviation: 3,8mDBtP2Bfpr), 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]-[1]benzoflo[3,2-d]pyrimidine (abbreviation: 4,8mDBtP2Bfpm), 8-[3'-(dibenzothiophen-4-yl)(1,1'-biphenyl- Examples include heteroaromatic compounds containing a heteroaromatic ring having a diazine (pyrimidine) ring, such as 3-yl)naphtho[1',2':4,5]flo[3,2-d]pyrimidine (abbreviation: 8mDBtBPNfpm) and 8-[(2,2'-binaphthalene)-6-yl]-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzoflo[3,2-d]pyrimidine (abbreviation: 8(βN2)-4mDBtPBfpm). Note that the above aromatic compounds containing heteroaromatic rings include heteroaromatic compounds having condensed heteroaromatic rings.

[0420] Other examples include 2,2'-(pyridine-2,6-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 2,6(P-Bqn)2Py), 2,2'-(2,2'-bipyridine-6,6'-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 6,6'(P-Bqn)2BPy), 2,2'-(pyridine-2,6-diyl)bis{4-[4-(2-naphthyl)phenyl]-6-phenylpyrimidine} (abbreviation: 2,6(NP-PPm)2Py), 6-(1,1'-biphenyl-3-yl)-4-[3,5-bis(9H-carbazole-9-yl)phenyl]-2-phenylpyrimidine (abbreviation: Examples include heteroaromatic compounds containing heteroaromatic rings having a diazine (pyrimidine) ring, such as 6mBP-4Cz2PPm, and heteroaromatic compounds containing heteroaromatic rings having a triazine ring, such as 2,4,6-tris[3'-(pyridin-3-yl)biphenyl-3-yl]-1,3,5-triazine (abbreviation: TmPPPyTz), 2,4,6-tris(2-pyridyl)-1,3,5-triazine (abbreviation: 2Py3Tz), and 2-[3-(2,6-dimethyl-3-pyridyl)-5-(9-phenanthryl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mPn-mDMePyPTzn).

[0421] Specific examples of heteroaromatic compounds having a fused ring structure that partially includes a 6-membered ring structure (heteroaromatic compounds having a fused ring structure) include bathophenanthroline (abbreviation: Bphen), vasocuproin (abbreviation: BCP), 2,9-di(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen), and 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] Phosphorus] (abbreviation: mPPhen2P), 2,2'-(1,1'-biphenyl)-3,3'-diylbis(9-phenyl-1,10-phenanthroline) (abbreviation: PPhen2BP), 2,2'-(pyridine-2,6-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 2,6(P-Bqn)2Py), 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3-(3'-dibenzothiophen-4-yl)biphenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazole-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4-(3,6-diphenyl-9H-carbazole-9-yl)phenyl]dibenzo[f,h Examples include heteroaromatic compounds having a quinoxaline ring, such as quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II), and 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II), 2mpPCBPDBq, etc.

[0422] In addition to the heteroaromatic compounds shown above, the following metal complexes can be used in the electron transport layers (114, 114a, 114b). Examples include metal complexes having a quinoline ring or benzoquinoline ring, such as tris(8-quinolinolato)aluminum(III) (abbreviated as Alq3), Almq3, 8-quinolinolato-lithium (abbreviated as Liq), BeBq2, bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviated as BAlq), and bis(8-quinolinolato)zinc(II) (abbreviated as Znq); and metal complexes having an oxazole ring or thiazole ring, such as bis[2-(2-benzoxazollyl)phenolato]zinc(II) (abbreviated as ZnPBO) and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviated as ZnBTZ).

[0423] Furthermore, polymer compounds such as poly(2,5-pyridinediyl) (abbreviated as PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py), and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy) can also be used as electron transport materials.

[0424] Furthermore, the electron transport layers (114, 114a, 114b) may be not only single layers, but also have a structure in which two or more layers made of the above material are stacked.

[0425] <Electron injection layer> The electron injection layers (115, 115a, 115b) are layers containing a material with high electron injection capabilities. Furthermore, the electron injection layers (115, 115a, 115b) are layers for increasing the electron injection efficiency from the second electrode 102, and it is preferable to use a material in which the difference between the work function value of the material used for the second electrode 102 and the LUMO level value of the material used for the electron injection layers (115, 115a, 115b) is small (0.5 eV or less). Therefore, the electron injection layer 115 contains lithium, cesium, lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), 8-quinolinolatrium (abbreviated as Liq), 2-(2-pyridyl)phenolate (abbreviated as LiPP), 2-(2-pyridyl)-3-pyridinolatrium (abbreviated as LiPPy), and 4-phenyl-2-(2-pyridyl)phenolate (abbreviated as LiPPP) lithium oxide (LiO2). x Alkali metals such as cesium carbonate, alkaline earth metals, or compounds thereof can be used. Rare earth metal compounds such as erbium fluoride (ErF3) and ytterbium (Yb) can also be used. The electron injection layers (115, 115a, 115b) may be formed by mixing multiple types of the above materials, or by stacking multiple types of the above materials. Electrides may also be used in the electron injection layers (115, 115a, 115b). Examples of electrides include substances obtained by adding a high concentration of electrons to a mixed oxide of calcium and aluminum. The materials that constitute the electron transport layers (114, 114a, 114b) described above can also be used.

[0426] Furthermore, a mixed material comprising an organic compound and an electron donor may be used in the electron injection layers (115, 115a, 115b). Such a mixed material exhibits excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material with excellent electron transport properties. Specifically, for example, an electron transport material (metal complex, or heteroaromatic compound, etc.) used in the electron transport layers (114, 114a, 114b) described above can be used. The electron donor can be any substance that exhibits electron-donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, or rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides or alkaline earth metal oxides are also preferred, such as lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (abbreviated as TTF) can also be used. Furthermore, multiple layers of these materials may be used.

[0427] In addition, a mixed material consisting of an organic compound and a metal may be used for the electron injection layers (115, 115a, 115b). The organic compound used here preferably has a LUMO level of -3.6 eV or higher and -2.3 eV or lower. Furthermore, a material having lone pairs of electrons is preferred.

[0428] Therefore, as the organic compound used in the above-mentioned mixed material, a mixed material obtained by mixing a heteroaromatic compound with a metal, as described above for use in an electron transport layer, may be used. Preferred heteroaromatic compounds include materials having lone pairs of electrons, such as heteroaromatic compounds having a 5-membered ring structure (imidazole ring, triazole ring, oxazole ring, oxadiazole ring, thiazole ring, benzimidazole ring, etc.), heteroaromatic compounds having a 6-membered ring structure (pyridine ring, diazine ring (including pyrimidine ring, pyrazine ring, pyridazine ring, etc.), triazine ring, bipyridine ring, terpyridine ring, etc.), and heteroaromatic compounds having a fused ring structure that partially includes a 6-membered ring structure (quinoline ring, benzoquinoline ring, quinoxaline ring, dibenzoquinoxaline ring, phenanthroline ring, etc.). Specific materials have been described above, so further explanation is omitted here.

[0429] Furthermore, it is preferable to use transition metals belonging to Group 5, Group 7, Group 9, or Group 11 of the periodic table, or materials belonging to Group 13, as the metals used in the above-mentioned mixed material. Examples include Ag, Cu, Al, or In. In this case, the organic compound forms a half-occupied orbital (SOMO) with the transition metal.

[0430] For example, when amplifying the light obtained from the light-emitting layer 113b, it is preferable to form the optical distance between the second electrode 102 and the light-emitting layer 113b to be less than 1 / 4 of the wavelength λ of the light emitted by the light-emitting layer 113b. In this case, this can be adjusted by changing the film thickness of the electron transport layer 114b or the electron injection layer 115b.

[0431] Furthermore, as shown in the light-emitting device in Figure 4(D), by providing a charge generation layer 106 between two EL layers (103a, 103b), a structure in which multiple EL layers are stacked between a pair of electrodes (also called a tandem structure) can be created.

[0432] <Charge generation layer> The charge generation layer 106 has the function of injecting electrons into the EL layer 103a and holes into the EL layer 103b when a voltage is applied between the first electrode (anode) 101 and the second electrode (cathode) 102. The charge generation layer 106 may be configured with electron acceptors added to a hole transport material, or with electron donors added to an electron transport material. Alternatively, both of these configurations may be laminated. By forming the charge generation layer 106 using the materials described above, the increase in driving voltage when the EL layers are laminated can be suppressed.

[0433] In the charge generation layer 106, if an electron acceptor is added to a hole-transporting material which is an organic compound, the material shown in this embodiment can be used as the hole-transporting material. Examples of electron acceptors include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviated as F4-TCNQ), chloranil, etc. Other examples include oxides of metals belonging to groups 4 through 8 of the periodic table. Specifically, examples include vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide.

[0434] Furthermore, in the charge generation layer 106, if an electron donor is added to the electron transport material, the material shown in this embodiment can be used as the electron transport material. As the electron donor, alkali metals, alkaline earth metals, rare earth metals, or metals belonging to groups 2 and 13 of the periodic table, as well as their oxides and carbonates, can be used. Specifically, lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide, cesium carbonate, etc., are preferred. Organic compounds such as tetrathianaphthalene may also be used as electron donors.

[0435] Although Figure 4(D) shows a configuration in which two EL layers 103 are stacked, a stacked structure of three or more EL layers may be used by providing a charge generation layer between different EL layers.

[0436] <Circuit board> The light-emitting device shown in this embodiment can be formed on various substrates. The type of substrate is not limited to any particular type. Examples of substrates include semiconductor substrates (e.g., single crystal substrates or silicon substrates), SOI substrates, glass substrates, quartz substrates, plastic substrates, metal substrates, stainless steel substrates, substrates with stainless steel foil, tungsten substrates, substrates with tungsten foil, flexible substrates, laminated films, paper containing fibrous materials, or base films.

[0437] Examples of glass substrates include barium borosilicate glass, aluminobrosilicate glass, or soda-lime glass. Examples of flexible substrates, laminated films, and base films include plastics such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polyethersulfone (PES), synthetic resins such as acrylic resins, polypropylene, polyester, polyvinyl fluoride, or polyvinyl chloride, polyamide, polyimide, aramid, epoxy resins, inorganic vapor-deposited films, or paper.

[0438] In this embodiment, the light-emitting device can be fabricated using vapor-phase methods such as vapor deposition, spin coating, or liquid-phase methods such as inkjet. When using vapor deposition, physical vapor deposition methods (PVD) such as sputtering, ion plating, ion beam deposition, molecular beam deposition, and vacuum deposition, or chemical vapor deposition (CVD) can be used. In particular, the various functional layers included in the EL layer of the light-emitting device (hole injection layer 111, hole transport layer 112, light-emitting layer 113, electron transport layer 114, electron injection layer 115) can be formed by methods such as vapor deposition (vacuum deposition, etc.), coating (dip coating, die coating, bar coating, spin coating, spray coating, etc.), and printing (inkjet, screen printing, offset printing, flexographic printing, gravure printing, microcontact printing, etc.).

[0439] Furthermore, when applying the above-mentioned coating method, printing method, or other film formation method, polymer compounds (oligomers, dendrimers, polymers, etc.), medium-molecular-weight compounds (compounds in the intermediate region between low-molecular-weight and high-molecular-weight compounds: molecular weight 400 to 4000), inorganic compounds (quantum dot materials, etc.) can be used. As for quantum dot materials, colloidal quantum dot materials, alloy-type quantum dot materials, core-shell type quantum dot materials, core-type quantum dot materials, etc., can be used.

[0440] The layers constituting the EL layer 103 of the light-emitting device shown in this embodiment (hole injection layer 111, hole transport layer 112, light-emitting layer 113, electron transport layer 114, electron injection layer 115) are not limited to the materials shown in this embodiment, and other materials can be used in combination as long as they can satisfy the function of each layer.

[0441] In this specification, the terms "layer" and "film" may be used interchangeably as appropriate.

[0442] The configuration shown in this embodiment can be used in appropriate combination with the configurations shown in other embodiments.

[0443] (Embodiment 4) This embodiment describes a specific configuration example of a light-receiving device, which is one aspect of the present invention, and an example of a manufacturing method.

[0444] <Example configuration of the light-receiving and light-emitting device 700> The light-receiving and light-emitting device 700 shown in Figure 5(A) includes light-emitting devices 550B, 550G, 550R, and a light-receiving device 550PS. The light-emitting devices 550B, 550G, 550R, and 550PS are formed on a functional layer 520 provided on a first substrate 510. The functional layer 520 includes circuits such as a drive circuit GD composed of multiple transistors, as well as wiring to electrically connect them. These drive circuits are, for example, electrically connected to the light-emitting devices 550B, 550G, 550R, and 550PS, respectively, and can drive them. Furthermore, the light-receiving and light-emitting device 700 includes an insulating layer 705 on the functional layer 520 and on each device (light-emitting device and light-receiving device), and the insulating layer 705 has the function of bonding the functional layer 520 to the second substrate 770.

[0445] The light-emitting devices 550B, 550G, 550R, and 550PS have the device structures shown in Embodiments 2 and 3. Specifically, each light-emitting device has one of the structures shown in Figure 4, and the light-receiving device has the structure shown in Figure 1(B). The structure of the light-receiving and receiving device shown in Figure 1(B) shows a structure in which a part of the EL layer of the light-emitting device (hole injection layer, hole transport layer, and electron transport layer) and a part of the active layer of the light-receiving device (first transport layer and second transport layer) are formed simultaneously from the same material during the manufacturing process. However, in this embodiment, we will describe a case in which not only the light-emitting and light-receiving devices, but also each device (multiple light-emitting devices and light-receiving devices) can be formed separately.

[0446] In this specification, a structure in which the light-emitting layers of each color light-emitting device (e.g., blue (B), green (G), and red (R)) and the light-receiving layer of the light-receiving device are made separately or painted separately may be referred to as an SBS (Side By Side) structure. In the light-emitting and light-receiving device 700 shown in Figure 5(A), the light-emitting device 550B, light-emitting device 550G, light-emitting device 550R, and light-receiving device 550PS are arranged in this order, but one aspect of the present invention is not limited to this configuration. For example, in the light-emitting and light-receiving device 700, these devices may be arranged in the order of light-emitting device 550R, light-emitting device 550G, light-emitting device 550B, and light-receiving device 550PS.

[0447] In Figure 5(A), the light-emitting device 550B has an electrode 551B, an electrode 552, and an EL layer 103B. The light-emitting device 550G has an electrode 551G, an electrode 552, and an EL layer 103G. The light-emitting device 550R has an electrode 551R, an electrode 552, and an EL layer 103R. The light-receiving device 550PS has an electrode 551PS, an electrode 552, and a light-receiving layer 103PS. The specific configuration of each layer of the light-receiving device is as shown in Embodiment 2. The specific configuration of each layer of the light-emitting device is as shown in Embodiment 3. The EL layers 103B, 103G, and 103R have a laminated structure consisting of multiple layers with different functions, including light-emitting layers (105B, 105G, 105R). The light-receiving layer 103PS has a laminated structure consisting of multiple layers with different functions, including an active layer 105PS. Figure 5(A) illustrates the case where the EL layer 103B has a hole injection / transport layer 104B, an emissive layer 105B, an electron transport layer 108B, and an electron injection layer 109; the case where the EL layer 103G has a hole injection / transport layer 104G, an emissive layer 105G, an electron transport layer 108G, and an electron injection layer 109; the case where the EL layer 103R has a hole injection / transport layer 104R, an emissive layer 105R, an electron transport layer 108R, and an electron injection layer 109; and the case where the light-receiving layer 103PS has a first transport layer 104PS, an active layer 105PS, a second transport layer 108PS, and an electron injection layer 109, but the present invention is not limited thereto. The hole injection / transport layers (104B, 104G, 104R) refer to layers having the functions of the hole injection layer and hole transport layer as shown in Embodiment 3, and may have a laminated structure.

[0448] Furthermore, the electron transport layers (108B, 108G, 108R) and the second transport layer 108PS may have a function to block holes moving from the anode side through the EL layer (103B, 103G, 103R) and the photodetector layer 103PS to the cathode side. In addition, the electron injection layer 109 may have a laminated structure formed using some or all different materials.

[0449] Furthermore, as shown in Figure 5(A), insulating layers 107 may be formed on the sides (or edges) of the hole injection / transport layers (104B, 104G, 104R), light-emitting layers (105B, 105G, 105R), and electron transport layers (108B, 108G, 108R) of the EL layers (103B, 103G, 103R), and on the sides (or edges) of the first transport layer 104PS, active layer 105PS, and second transport layer 108PS of the light-receiving layer 103PS. The insulating layer 107 is formed in contact with the sides (or edges) of the EL layers (103B, 103G, 103R) and the light-receiving layer 103PS. This prevents the intrusion of oxygen, moisture, or their constituent elements into the interior from the sides of the EL layers (103B, 103G, 103R) and the light-receiving layer 103PS. For example, aluminum oxide, magnesium oxide, hafnium oxide, gallium oxide, indium gallium zinc oxide, silicon nitride, or silicon oxide nitride can be used for the insulating layer 107. The insulating layer 107 may also be formed by laminating the aforementioned materials. Sputtering, CVD, MBE, PLD, ALD, etc. can be used to form the insulating layer 107, but the ALD method, which has good coverage, is more preferable. The insulating layer 107 has a structure that continuously covers the sides (or edges) of the EL layers (103B, 103G, 103R) of adjacent light-emitting devices or the light-receiving layer 103PS of the light-receiving device. For example, in Figure 5(A), the EL layer 103B of the light-emitting device 550B and the EL layer 103G of the light-emitting device 550G are covered with an insulating layer 107BG. Furthermore, it is preferable that a partition wall 528 made of an insulating material is formed in the region covered by the insulating layer 107BG, as shown in Figure 5(A).

[0450] Furthermore, an electron injection layer 109 is formed on the electron transport layer (108B, 108G, 108R), which is part of the EL layer (103B, 103G, 103R), the second transport layer 108PS, which is part of the light-receiving layer 103PS, and the insulating layer 107. The electron injection layer 109 may also be a stacked structure of two or more layers (for example, a stack of layers with different electrical resistances).

[0451] Furthermore, electrode 552 is formed on the electron injection layer 109. Note that electrodes (551B, 551G, 551R) and electrode 552 have overlapping regions. Additionally, there is an emissive layer 105B between electrode 551B and electrode 552, an emissive layer 105G between electrode 551G and electrode 552, an emissive layer 105R between electrode 551R and electrode 552, and a light-receiving layer 103PS between electrode 551PS and electrode 552.

[0452] Furthermore, the EL layers (103B, 103G, 103R) shown in Figure 5(A) have the same configuration as the EL layer 103 described in Embodiment 3. Also, the light-receiving layer 103PS has the same configuration as the light-receiving layer 203 described in Embodiment 2. In addition, for example, the light-emitting layer 105B can emit blue light, the light-emitting layer 105G can emit green light, and the light-emitting layer 105R can emit red light.

[0453] A partition wall 528 and an insulating layer 107 are provided between a portion of the light-emitting device 550B, a portion of the light-emitting device 550G, a portion of the light-emitting device 550R, and a portion of the light-receiving device 550PS, respectively. As shown in Figure 5(A), the electrodes (551B, 551G, 551R, 551PS) of each light-emitting device, a portion of the EL layer (103B, 103G, 103R), and a portion of the light-receiving layer 103PS are in contact with the partition wall 528 at their sides (or ends) via the insulating layer 107.

[0454] In each EL layer and photodetector layer, the hole injection layer, particularly the hole transport region located between the anode and the light-emitting layer, and between the anode and the active layer, often has high conductivity. Therefore, if it is formed as a layer common to adjacent light-emitting devices or photodetectors, it may cause crosstalk. Accordingly, by providing a partition wall 528 made of insulating material between each EL layer and the photodetector layer, as shown in this example configuration, it is possible to suppress the occurrence of crosstalk between adjacent devices (between a photodetector and a light-emitting device, between light-emitting devices, or between photodetectors).

[0455] Furthermore, in the manufacturing method described in this embodiment, the sides (or edges) of the EL layer and the light-receiving layer are exposed during the patterning process. As a result, the EL layer and the light-receiving layer are more susceptible to deterioration due to the intrusion of oxygen or water from the sides (or edges) of the EL layer and the light-receiving layer. Therefore, by providing the partition wall 528, it is possible to suppress the deterioration of the EL layer and the light-receiving layer during the manufacturing process.

[0456] Furthermore, by providing the partition wall 528, it is possible to flatten the recesses formed between adjacent devices (between a light-receiving device and a light-emitting device, between light-emitting devices and light-emitting devices, or between light-receiving devices and light-receiving devices). By flattening the recesses, it is possible to suppress disconnection of the electrodes 552 formed on each EL layer and light-receiving layer. As the insulating material used to form the partition wall 528, organic materials such as acrylic resin, polyimide resin, epoxy resin, imide resin, polyamide resin, polyimidoamide resin, silicone resin, siloxane resin, benzocyclobutene resin, phenol resin, and precursors of these resins can be applied. Alternatively, organic materials such as polyvinyl alcohol (PVA), polyvinyl butyral, polyvinylpyrrolidone, polyethylene glycol, polyglycerin, pullulan, water-soluble cellulose, or alcohol-soluble polyamide resin may be used. In addition, photosensitive resins such as photoresists can be used. The photosensitive resin can be a positive-type material or a negative-type material.

[0457] By using a photosensitive resin, the partition wall 528 can be fabricated using only the exposure and development processes. Alternatively, the partition wall 528 may be formed using a negative-type photosensitive resin (e.g., a resist material). Furthermore, when an insulating layer having an organic material is used as the partition wall 528, it is preferable to use a material that absorbs visible light. By using a material that absorbs visible light for the partition wall 528, the light emitted from the EL layer can be absorbed by the partition wall 528, thereby suppressing light (stray light) that may leak into the adjacent EL layer and light-receiving layer. Therefore, a display panel with high display quality can be provided.

[0458] Furthermore, the difference between the height of the upper surface of the partition wall 528 and the height of the upper surface of any of the EL layer 103B, EL layer 103G, EL layer 103R, and light-receiving layer 103PS is preferably 0.5 times or less the thickness of the partition wall 528, and more preferably 0.3 times or less. Also, for example, the partition wall 528 may be provided such that the upper surface of any of the EL layer 103B, EL layer 103G, EL layer 103R, and light-receiving layer 103PS is higher than the upper surface of the partition wall 528. Also, for example, the partition wall 528 may be provided such that the upper surface of the partition wall 528 is higher than the upper surface of the EL layer 103B, EL layer 103G, EL layer 103R, and light-receiving layer 103PS.

[0459] In a high-resolution light-emitting and receiving device (display panel) with a resolution exceeding 1000 ppi, if electrical conductivity is detected between the EL layer 103B, EL layer 103G, EL layer 103R, and the light-receiving layer 103PS, a crosstalk phenomenon occurs, narrowing the displayable color gamut of the light-emitting and receiving device. By providing a partition wall 528 in a high-resolution display panel exceeding 1000 ppi, preferably a high-resolution display panel exceeding 2000 ppi, and more preferably an ultra-high-resolution display panel exceeding 5000 ppi, a display panel capable of displaying vivid colors can be provided.

[0460] Furthermore, Figures 5(B) and 5(C) show schematic top views of the light-receiving device 700 corresponding to the dashed line Ya-Yb in the cross-sectional view of Figure 5(A). That is, light-emitting devices 550B, 550G, and 550R are arranged in a matrix. Figure 5(B) shows a so-called stripe arrangement in which light-emitting devices of the same color are arranged in the X direction. Figure 5(C) shows a configuration in which light-emitting devices of the same color are arranged in the X direction, but a pattern is formed for each pixel. Note that the arrangement method of the light-emitting devices is not limited to these, and arrangement methods such as delta arrangement and zigzag arrangement may be applied, or pentile arrangement and diamond arrangement may be used.

[0461] Furthermore, since the separation process of each EL layer (EL layer 103B, EL layer 103G, and EL layer 103R) and the light-receiving layer 103PS is performed using photolithography, a high-definition light-receiving device (display panel) can be manufactured. In addition, the edges (sides) of the EL layers and light-receiving layer 103PS processed by photolithography have a shape that is substantially the same surface (or substantially located on the same plane). At this time, the width (SE) of the gap 580 between each EL layer and light-receiving layer is preferably 5 μm or less, and more preferably 1 μm or less.

[0462] In EL layers, the hole injection layer, particularly the hole transport region located between the anode and the light-emitting layer, often has high conductivity. Therefore, if it is formed as a common layer for adjacent light-emitting devices, it can cause crosstalk. Consequently, by separating the EL layer using photolithography, as shown in this example configuration, it is possible to suppress the occurrence of crosstalk between adjacent light-emitting devices.

[0463] Furthermore, Figure 5(D) is a schematic cross-sectional view corresponding to the dashed line C1-C2 in Figures 5(B) and 5(C). Figure 5(D) shows the connection portion 130 where the connecting electrode 551C and electrode 552 are electrically connected. At the connection portion 130, electrode 552 is provided in contact with the connecting electrode 551C. In addition, a partition wall 528 is provided covering the end of the connecting electrode 551C.

[0464] <Example of a manufacturing method for a light-receiving device> As shown in Figure 6(A), electrodes 551B, 551G, 551R, and 551PS are formed. For example, a conductive film is formed on a functional layer 520 formed on a first substrate 510, and then processed into a predetermined shape using photolithography.

[0465] Conductive films can be formed using methods such as sputtering, chemical vapor deposition (CVD), molecular beam epitaxy (MBE), vacuum deposition, pulsed laser deposition (PLD), and atomic layer deposition (ALD). CVD methods include plasma-enhanced CVD (PECVD) and thermal CVD. One type of thermal CVD is metal-organic CVD (MOCVD).

[0466] In addition to the photolithography method described above, conductive films may also be processed using nanoimprint lithography, sandblasting, lift-off methods, etc. Island-like thin films may also be directly formed using a film deposition method that utilizes a shielding mask such as a metal mask.

[0467] There are two main methods of photolithography. One method involves forming a resist mask on a thin film to be processed, processing the thin film by etching or other means, and then removing the resist mask. The other method involves forming a photosensitive thin film, then exposing and developing it to process the thin film into a desired shape. The former method involves heat treatment steps such as heating after resist coating (PAB: Pre-Applied Bake) and heating after exposure (PEB: Post-Exposure Bake). In one aspect of the present invention, lithography is used not only for processing conductive films but also for processing thin films (films made of organic compounds, or films containing organic compounds in part) used to form an EL layer.

[0468] In photolithography, the light used for exposure can be, for example, i-line (wavelength 365 nm), g-line (wavelength 436 nm), h-line (wavelength 405 nm), or a mixture thereof. Other options include ultraviolet light, KrF laser light, or ArF laser light. Exposure may also be performed using immersion lithography. Furthermore, extreme ultraviolet (EUV) light or X-rays may be used as the light source for exposure. An electron beam can also be used instead of light for exposure. Using extreme ultraviolet light, X-rays, or an electron beam is preferable because it allows for extremely fine processing. Note that a photomask is not required when exposure is performed by scanning a beam such as an electron beam.

[0469] For etching thin films using a resist mask, methods such as dry etching, wet etching, and sandblasting can be used.

[0470] Next, as shown in Figure 6(B), a hole injection / transport layer 104B, an emissive layer 105B, and an electron transport layer 108B are formed on electrodes 551B, 551G, 551R, and 551PS, respectively. For example, vacuum deposition can be used to form the hole injection / transport layer 104B, the emissive layer 105B, and the electron transport layer 108B. Furthermore, a sacrificial layer 110B is formed on the electron transport layer 108B. In forming the hole injection / transport layer 104B, the emissive layer 105B, and the electron transport layer 108B, the material shown in Embodiment 3 can be used.

[0471] Furthermore, it is preferable to use a film for the sacrificial layer 110B that has high resistance to etching of the hole injection / transport layer 104B, the light-emitting layer 105B, and the electron transport layer 108B, i.e., a film with a high etching selectivity ratio. It is also preferable that the sacrificial layer 110B has a laminated structure of a first sacrificial layer and a second sacrificial layer with different etching selectivity ratios. Additionally, the sacrificial layer 110B can be a film that can be removed by a wet etching method that causes minimal damage to the EL layer 103B. Oxalic acid can be used as the etching material for wet etching.

[0472] As the sacrificial layer 110B, for example, an inorganic film such as a metal film, alloy film, metal oxide film, semiconductor film, or inorganic insulating film can be used. Furthermore, the sacrificial layer 110B can be formed by various film deposition methods such as sputtering, vapor deposition, CVD, and ALD.

[0473] As the sacrificial layer 110B, metal materials such as gold, silver, platinum, magnesium, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, titanium, aluminum, yttrium, zirconium, and tantalum, or alloy materials containing such metal materials, can be used. In particular, it is preferable to use low-melting-point materials such as aluminum or silver.

[0474] Furthermore, metal oxides such as indium gallium zinc oxide (In-Ga-Zn oxide, also written as IGZO) can be used as the sacrificial layer 110B. In addition, indium oxide, indium zinc oxide (In-Zn oxide), indium tin oxide (In-Sn oxide), indium titanium oxide (In-Ti oxide), indium tin zinc oxide (In-Sn-Zn oxide), indium titanium zinc oxide (In-Ti-Zn oxide), indium gallium tin zinc oxide (In-Ga-Sn-Zn oxide), etc. can be used. Alternatively, indium tin oxide containing silicon can also be used.

[0475] Furthermore, the above-mentioned method can also be applied when element M (where M is one or more selected from aluminum, silicon, boron, yttrium, copper, vanadium, beryllium, titanium, iron, nickel, germanium, zirconium, molybdenum, lanthanum, cerium, neodymium, hafnium, tantalum, tungsten, or magnesium) is used instead of gallium. In particular, it is preferable that M be one or more selected from gallium, aluminum, or yttrium.

[0476] Furthermore, inorganic insulating materials such as aluminum oxide, hafnium oxide, and silicon oxide can be used as the sacrificial layer 110B.

[0477] Furthermore, it is preferable to use a material that is soluble in a chemically stable solvent for at least the uppermost electron transport layer 108B as the sacrificial layer 110B. In particular, a material soluble in water or alcohol can be suitably used for the sacrificial layer 110B. When forming the sacrificial layer 110B, it is preferable to coat it using a wet deposition method while dissolved in a solvent such as water or alcohol, and then perform a heat treatment to evaporate the solvent. At this time, performing the heat treatment under a reduced pressure atmosphere is preferable because it allows the solvent to be removed at a low temperature and in a short time, thereby reducing thermal damage to the hole injection / transport layer 104B, the light-emitting layer 105B, and the electron transport layer 108B.

[0478] Furthermore, when the sacrificial layer 110B is to be made into a laminated structure, the layer formed from the above-mentioned material can be designated as the first sacrificial layer, and a second sacrificial layer can be formed on top of it to create a laminated structure.

[0479] In this case, the second sacrificial layer is a film used as a hard mask when etching the first sacrificial layer. Furthermore, the first sacrificial layer is exposed during processing of the second sacrificial layer. Therefore, the first and second sacrificial layers are selected based on a combination of films that have a high etching selectivity ratio for each other. Thus, the film that can be used for the second sacrificial layer can be selected according to the etching conditions for both the first and second sacrificial layers.

[0480] For example, when dry etching using a fluorine-containing gas (also called a fluorine-based gas) is used for etching the second sacrificial layer, silicon, silicon nitride, silicon oxide, tungsten, titanium, molybdenum, tantalum, tantalum nitride, alloys containing molybdenum and niobium, or alloys containing molybdenum and tungsten can be used for the second sacrificial layer. Here, metal oxide films such as IGZO and ITO can be used for the first sacrificial layer as films that allow for a higher selectivity ratio for etching (i.e., a slower etching rate) compared to dry etching using the above-mentioned fluorine-based gas.

[0481] However, the second sacrificial layer can be selected from a variety of materials, depending on the etching conditions of the first sacrificial layer and the etching conditions of the second sacrificial layer. For example, it can be selected from among the films that can be used for the first sacrificial layer.

[0482] Furthermore, a nitride film can be used as the second sacrificial layer. Specifically, nitrides such as silicon nitride, aluminum nitride, hafnium nitride, titanium nitride, tantalum nitride, tungsten nitride, gallium nitride, and germanium nitride can be used.

[0483] Alternatively, an oxide film can be used as the second sacrificial layer. Typically, oxide films or oxynitride films such as silicon oxide, silicon oxynitride, aluminum oxide, aluminum oxynitride, hafnium oxide, and hafnium oxynitride can be used.

[0484] Next, as shown in Figure 6(C), a resist is applied to the sacrificial layer 110B, and the resist is formed into the desired shape (resist mask: REG) using photolithography. Note that this method involves heat treatment steps such as heating after resist application (PAB: Pre-Applied Bake) and heating after exposure (PEB: Post-Exposure Bake). For example, the PAB temperature is around 100°C, and the PEB temperature is around 120°C. Therefore, the light-emitting device must be able to withstand these processing temperatures.

[0485] Next, using the obtained resist mask REG, a portion of the sacrificial layer 110B not covered by the resist mask REG is removed by etching. After removing the resist mask REG, the hole injection / transport layer 104B, light-emitting layer 105B, and electron transport layer 108B not covered by the sacrificial layer are removed by etching, and the hole injection / transport layer 104B, light-emitting layer 105B, and electron transport layer 108B are processed into a shape having sides on the electrode 551B (or with exposed sides), or into a strip shape extending in a direction intersecting the paper plane. Dry etching is preferred for etching. If the sacrificial layer 110B has a laminated structure of the first sacrificial layer and the second sacrificial layer, a portion of the second sacrificial layer may be etched with the resist mask REG, then the resist mask REG is removed, and the second sacrificial layer is used as a mask to etch a portion of the first sacrificial layer, and the hole injection / transport layer 104B, light-emitting layer 105B, and electron transport layer 108B may be processed into a predetermined shape. These etching processes yield the shape shown in Figure 7(A).

[0486] Next, as shown in Figure 7(B), a hole injection / transport layer 104G, an emissive layer 105G, and an electron transport layer 108G are formed on the sacrificial layer 110B, electrode 551G, electrode 551R, and electrode 551PS. For the formation of the hole injection / transport layer 104G, emissive layer 105G, and electron transport layer 108G, the materials shown in Embodiment 3 can be used. For example, vacuum deposition can be used to form the hole injection / transport layer 104G, emissive layer 105G, and electron transport layer 108G.

[0487] Next, as shown in Figure 7(C), a sacrificial layer 110G is formed on the electron transport layer 108G, a resist is applied on the sacrificial layer 110G, and the resist is formed into a desired shape (resist mask: REG) using photolithography. A portion of the sacrificial layer 110G not covered by the obtained resist mask is removed by etching. After removing the resist mask, the hole injection / transport layer 104G, light-emitting layer 105G, and electron transport layer 108G not covered by the sacrificial layer are removed by etching, and the hole injection / transport layer 104G, light-emitting layer 105G, and electron transport layer 108G are processed into a shape with sides on the electrode 551G (or with exposed sides), or into a strip shape extending in a direction intersecting the paper plane. Dry etching is preferred for etching. Furthermore, the sacrificial layer 110G can be made of the same material as the sacrificial layer 110B. If the sacrificial layer 110G has a laminated structure with the first and second sacrificial layers, a portion of the second sacrificial layer may be etched using a resist mask, then the resist mask may be removed, and the second sacrificial layer may be used as a mask to etch a portion of the first sacrificial layer, thereby processing the hole injection / transport layer 104G, the light-emitting layer 105G, and the electron transport layer 108G into a predetermined shape. These etching processes result in the shape shown in Figure 8(A).

[0488] Next, as shown in Figure 8(B), a hole injection / transport layer 104R, an emissive layer 105R, and an electron transport layer 108R are formed on the sacrificial layer 110B, sacrificial layer 110G, electrode 551R, and electrode 551PS. For the formation of the hole injection / transport layer 104R, emissive layer 105R, and electron transport layer 108R, the material shown in Embodiment 3 can be used. For example, a vacuum deposition method can be used to form the hole injection / transport layer 104R, emissive layer 105R, and electron transport layer 108R.

[0489] Next, as shown in Figure 8(C), a sacrificial layer 110R is formed on the electron transport layer 108R, a resist is applied on the sacrificial layer 110R, and the resist is formed into a desired shape (resist mask: REG) using photolithography. A portion of the sacrificial layer 110R not covered by the obtained resist mask REG is removed by etching. After removing the resist mask REG, the hole injection / transport layer 104R, light-emitting layer 105R, and electron transport layer 108R not covered by the sacrificial layer are removed by etching, and the hole injection / transport layer 104R, light-emitting layer 105R, and electron transport layer 108R are processed into a shape with sides on the electrode 551R (or with exposed sides), or into a strip shape extending in a direction intersecting the paper plane. Dry etching is preferred for etching. Furthermore, the sacrificial layer 110R can be made of the same material as the sacrificial layer 110B. If the sacrificial layer 110R has a laminated structure with the first sacrificial layer and the second sacrificial layer, a portion of the second sacrificial layer may be etched with a resist mask REG, then the resist mask REG is removed, and the second sacrificial layer is used as a mask to etch a portion of the first sacrificial layer, thereby processing the hole injection / transport layer 104R, the light-emitting layer 105R, and the electron transport layer 108R into a predetermined shape. These etching processes result in the shape shown in Figure 9(A).

[0490] Next, as shown in Figure 9(B), a first transport layer 104PS, an active layer 105PS, and a second transport layer 108PS are formed on the sacrificial layer 110B, sacrificial layer 110G, sacrificial layer 110R, and electrode 551PS. In forming the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS, the material shown in Embodiment 2 can be used. For example, a vacuum deposition method can be used to form the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS.

[0491] Next, as shown in Figure 9(C), a sacrificial layer 110PS is formed on the second transport layer 108PS, a resist is applied on the sacrificial layer 110PS, and the resist is formed into a desired shape (resist mask: REG) using photolithography. A portion of the sacrificial layer 110PS not covered by the obtained resist mask REG is removed by etching. After removing the resist mask REG, the first transport layer 104PS, active layer 105PS, and second transport layer 108PS not covered by the sacrificial layer 110PS are removed by etching, and the first transport layer 104PS, active layer 105PS, and second transport layer 108PS are processed into a shape having sides on the electrode 551PS (or with exposed sides), or into a strip shape extending in a direction intersecting the paper plane. Dry etching is preferred for etching. Furthermore, the sacrificial layer 110PS can be made of the same material as the sacrificial layer 110B. If the sacrificial layer 110PS has a laminated structure with the first sacrificial layer and the second sacrificial layer, a portion of the second sacrificial layer may be etched with a resist mask REG, then the resist mask REG is removed, and a portion of the first sacrificial layer is etched using the second sacrificial layer as a mask, thereby processing the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS into a predetermined shape. These etching processes result in the shape shown in Figure 9(D).

[0492] Next, as shown in Figure 10(A), an insulating layer 107 is formed on the sacrificial layer 110B, sacrificial layer 110G, sacrificial layer 110R, and sacrificial layer 110PS.

[0493] For example, the ALD method can be used to form the insulating layer 107. In this case, as shown in Figure 10(A), the insulating layer 107 is formed in contact with the hole injection / transport layers (104B, 104G, 104R), light-emitting layers (105R, 105G, 105B), and electron transport layers (108B, 108G, 108R) of each light-emitting device, as well as the sides (ends) of the first transport layer 104PS, active layer 105PS, and second transport layer 108PS of the light-receiving device. This suppresses the penetration of oxygen, moisture, or their constituent elements into the interior from each side. As for the material used for the insulating layer 107, for example, aluminum oxide, magnesium oxide, hafnium oxide, gallium oxide, indium gallium zinc oxide, silicon nitride, or silicon nitride oxide can be used.

[0494] Next, as shown in Figure 10(B), a portion of the insulating layer 107 is removed to expose the sacrificial layers 110B, G, R, and PS. After removing the sacrificial layers (110B, 110G, 110R, 110PS), an electron injection layer 109 is formed on the insulating layer (107B, 107G, 107R, 107PS), the electron transport layer (108B, 108G, 108R), and the second transport layer 108PS. In forming the electron injection layer 109, the material shown in Embodiment 3 can be used. The electron injection layer 109 is formed, for example, by vacuum deposition. Furthermore, the electron injection layer 109 has a structure in which it is in contact with the hole injection / transport layers (104B, 104G, 104R), light-emitting layers (105R, 105G, 105B), and electron transport layers (108B, 108G, 108R) of each light-emitting device, as well as with the first transport layer 104PS, active layer 105PS, and second transport layer 108PS of the photodetector, via insulating layers (107B, 107G, 107R, 107PS) on each side (each end).

[0495] Next, as shown in Figure 10(C), an electrode 552 is formed. The electrode 552 is formed, for example, by vacuum deposition. The electrode 552 is formed on the electron injection layer 109. The electrode 552 has a structure that contacts the hole injection / transport layers (104B, 104G, 104R), light-emitting layers (105R, 105G, 105B), and electron transport layers (108B, 108G, 108R) of each light-emitting device, as well as the sides (ends) of the first transport layer 104PS, active layer 105PS, and second transport layer 108PS of the photodetector, via the electron injection layer 109 and insulating layers (107B, 107G, 107R, 107PS). This prevents electrical short circuits between the hole injection / transport layers (104B, 104G, 104R), light-emitting layers (105R, 105G, 105B), and electron transport layers (108B, 108G, 108R) of each light-emitting device, as well as between the first transport layer 104PS, active layer 105PS, second transport layer 108PS of the photodetector and the electrode 552.

[0496] Through the above process, the EL layer 103B, EL layer 103G, EL layer 103R, and light-receiving layer 103PS of the light-emitting device 550B, light-emitting device 550G, light-emitting device 550R, and light-receiving device 550PS can be separated and processed, respectively.

[0497] Furthermore, since the separation process of these EL layers (EL layer 103B, EL layer 103G, EL layer 103R) and the light-receiving layer 103PS is performed using photolithography, a high-resolution light-receiving device (display panel) can be manufactured. In addition, the edges (sides) of the EL layers and light-receiving layer 103PS processed by photolithography have a shape that is substantially the same surface (or is substantially located on the same plane).

[0498] Furthermore, the hole injection / transport layers (104B, 104G, 104R) in these EL layers, and the first transport layer 104PS in the photodetector layer, often have high conductivity. Therefore, if they are formed as layers common to adjacent devices, they can cause crosstalk. Accordingly, by separating the EL layers through pattern formation using photolithography, as shown in this example configuration, it is possible to suppress the occurrence of crosstalk between adjacent light-emitting and light-receiving devices.

[0499] Furthermore, in each EL layer (EL layer 103B, EL layer 103G, and EL layer 103R) of this light-emitting device, the hole injection / transport layer (104B, 104G, 104R), light-emitting layer (105R, 105G, 105B), and electron transport layer (108B, 108G, 108R) contained within each EL layer, and the first transport layer 104PS, active layer 105PS, and second transport layer 108PS of the light-receiving layer 103PS of the light-receiving device are patterned using photolithography during the separation process. As a result, the edges (sides) of the processed EL layers and light-receiving layers have approximately the same surface (or are located on approximately the same plane).

[0500] Furthermore, the hole injection / transport layers (104B, 104G, 104R), light-emitting layers (105R, 105G, 105B), and electron transport layers (108B, 108G, 108R) contained in each EL layer (EL layer 103B, EL layer 103G, and EL layer 103R) of each light-emitting device, and the first transport layer 104PS, active layer 105PS, and second transport layer 108PS of the light-receiving layer 103PS of the light-receiving device, are patterned using photolithography during the separation process. As a result, each processed end (side) has a gap 580 between it and the adjacent device. In Figure 10(C), if the gap 580 is represented by SE as the distance between the EL layers or light-receiving layers of adjacent devices, a smaller distance SE allows for a higher aperture ratio and higher resolution. On the other hand, the larger the distance SE, the more tolerance is given to variations in the manufacturing process between adjacent devices, thereby increasing the manufacturing yield. Since the light-emitting devices and photodetectors manufactured according to this specification are suitable for miniaturization processes, the distance SE between the EL layer or photodetector layer of adjacent devices can be 0.5 μm or more and 5 μm or less, preferably 1 μm or more and 3 μm or less, more preferably 1 μm or more and 2.5 μm or less, and even more preferably 1 μm or more and 2 μm or less. Typically, the distance SE is preferably 1 μm or more and 2 μm or less (for example, 1.5 μm or nearby).

[0501] In this specification, devices fabricated using a metal mask or FMM (Fine Metal Mask, a high-resolution metal mask) may be referred to as MM (Metal Mask) structured devices. Furthermore, in this specification, devices fabricated without using a metal mask or FMM may be referred to as MML (Metal Maskless) structured devices. Because MML structured light-receiving devices are fabricated without a metal mask, they offer greater design flexibility in terms of pixel arrangement and pixel shape compared to FMM or MM structured light-receiving devices.

[0502] Furthermore, the island-shaped EL layers in MML structured light-emitting devices are not formed by the pattern on the metal mask, but rather by processing after the EL layer has been deposited. Therefore, it is possible to realize light-emitting devices with higher resolution or higher aperture ratios than before. In addition, since the EL layer can be manufactured separately for each color, it is possible to realize light-emitting devices with extremely vivid colors, high contrast, and high display quality. Moreover, by providing a sacrificial layer on the EL layer, the damage the EL layer receives during the manufacturing process can be reduced, thereby increasing the reliability of the light-emitting device.

[0503] In the light-emitting devices 550B, 550G, and 550R shown in Figures 5(A) and 10(C), the width of the EL layer (103B, 103G, 103R) is approximately equal to the width of the electrodes (551B, 551G, 551R), and in the light-receiving device 550PS, the width of the light-receiving layer 103PS is approximately equal to the width of the electrode 551PS; however, the present invention is not limited to these embodiments.

[0504] In the light-emitting devices 550B, 550G, and 550R, the width of the EL layer (103B, 103G, 103R) may be smaller than the width of the electrodes (551B, 551G, 551R). Also, in the light-receiving device 550PS, the width of the light-receiving layer 103PS may be smaller than the width of the electrode 551PS. Figure 10(D) shows an example in the light-emitting devices 550B and 550G where the width of the EL layer (103B, 103G) is smaller than the width of the electrodes (551B, 551G).

[0505] In the light-emitting devices 550B, 550G, and 550R, the width of the EL layer (103B, 103G, 103R) may be greater than the width of the electrodes (551B, 551G, 551R). Also, in the light-receiving device 550PS, the width of the light-receiving layer 103PS may be greater than the width of the electrode 551PS. Figure 10(E) shows an example in the light-emitting device 550R where the width of the EL layer 103R is greater than the width of the electrode 551R.

[0506] The configuration shown in this embodiment can be used in appropriate combination with the configurations shown in other embodiments.

[0507] (Embodiment 5) In this embodiment, the light-receiving and light-emitting device 720 will be described with reference to Figures 11 to 13. The light-receiving and light-emitting device 720 shown in Figures 11 to 13 is a light-receiving and light-emitting device having a light-receiving device and a light-emitting device as shown in Embodiments 2 and 3. However, the light-receiving and light-emitting device 720 described in this embodiment can also be called a display panel or display device because it is applicable to the display section of electronic equipment and the like. The above-described light-receiving and light-emitting device has a configuration in which the light-emitting device is used as a light source and the light from the light-emitting device is received by the light-receiving device.

[0508] Furthermore, the light-receiving device of this embodiment can be a high-resolution or large-screen light-receiving device. Therefore, the light-receiving device of this embodiment can be used in electronic devices with relatively large screens, such as television sets, desktop or notebook personal computers, computer monitors, digital signage, and large game machines such as pachinko machines, as well as in the display units of digital cameras, digital video cameras, digital photo frames, mobile phones, portable game consoles, smartphones, smartwatches, tablet devices, personal information terminals, and audio playback devices.

[0509] Figure 11(A) shows a top view of the light-receiving device 720.

[0510] In Figure 11(A), the light-receiving device 720 has a configuration in which substrates 710 and 711 are bonded together. The light-receiving device 720 also has a display area 701, a circuit 704, and wiring 706, etc. The display area 701 has multiple pixels, and as shown in Figure 11(A), pixel 703(i,j) has an adjacent pixel 703(i+1,j) as shown in Figure 11(B).

[0511] Furthermore, as shown in Figure 11(A), the light-receiving device 720 is shown as an example in which an IC (integrated circuit) 712 is provided on the substrate 710 using a COG (Chip On Glass) method or a COF (Chip On Film) method. For example, an IC having a scan line drive circuit or a signal line drive circuit can be used as IC 712. Figure 11(A) shows a configuration in which an IC having a signal line drive circuit is used as IC 712, and circuit 704 has a scan line drive circuit.

[0512] The wiring 706 has the function of supplying signals and power to the display area 701 and the circuit 704. These signals and power are input to the wiring 706 from an external source via the FPC (Flexible Printed Circuit) 713, or from the IC 712. The light-receiving device 720 may be configured without an IC. Alternatively, the IC may be mounted on the FPC using a COF (Cable Oscillator) method or the like.

[0513] Figure 11(B) shows pixels 703(i,j) and 703(i+1,j) of the display area 701. That is, pixel 703(i,j) can be configured to have multiple subpixels, each having a light-emitting device that emits a different color. Alternatively, in addition to the above, it can also be configured to include multiple subpixels having light-emitting devices that emit the same color. For example, a pixel can be configured to have three types of subpixels. Examples of these three subpixels include subpixels of three colors: red (R), green (G), and blue (B); or subpixels of three colors: yellow (Y), cyan (C), and magenta (M). Alternatively, a pixel can be configured to have four types of subpixels. Examples of these four subpixels include subpixels of four colors: R, G, B, and white (W); or subpixels of four colors: R, G, B, and Y. Specifically, it can be a pixel 703(i,j) composed of sub-pixels 702B(i,j) that display blue, sub-pixels 702G(i,j) that display green, and sub-pixels 702R(i,j) that display red.

[0514] Furthermore, the sub-pixel may be configured to include not only a light-emitting device but also a light-receiving device.

[0515] Figures 11(C) to 11(F) show pixel 703(i,j) which includes a sub-pixel 702PS(i,j) with a light-receiving device, illustrating various layout examples. The pixel arrangement shown in Figure 11(C) is a stripe arrangement, and the pixel arrangement shown in Figure 11(D) is a matrix arrangement. The pixel arrangement shown in Figure 11(E) has a configuration where three sub-pixels (sub-pixel R, sub-pixel G, and sub-pixel PS) are arranged vertically next to one sub-pixel (sub-pixel B). The pixel arrangement shown in Figure 11(F) has a configuration where three vertically elongated sub-pixels G, B, and R are arranged horizontally, with sub-pixel PS and a horizontally elongated sub-pixel IR arranged horizontally below them. The wavelength of light detected by sub-pixel 702PS(i,j) is not particularly limited, but it is preferable that the light-receiving device of sub-pixel 702PS(i,j) is sensitive to the light emitted by the light-emitting device of sub-pixel 702R(i,j), sub-pixel 702G(i,j), sub-pixel 702B(i,j), or sub-pixel 702IR(i,j). For example, it is preferable to detect one or more of the following wavelengths: blue, violet, blue-violet, green, yellow-green, yellow, orange, red, and infrared.

[0516] Furthermore, as shown in Figure 11(F), a sub-pixel 702IR(i,j) that emits infrared light may be added to the above pair and designated as pixel 703(i,j). Specifically, a sub-pixel that emits light including light with a wavelength of 650 nm to 1000 nm may be used as pixel 703(i,j).

[0517] Furthermore, the arrangement of subpixels is not limited to the configurations shown in Figures 11(B) to 11(F), and various methods can be applied. Examples of subpixel arrangements include stripe arrangements, S-stripe arrangements, matrix arrangements, delta arrangements, Bayer arrangements, and pentile arrangements.

[0518] Furthermore, the top surface shape of a sub-pixel can be, for example, a polygon such as a triangle, quadrilateral (including rectangles and squares), or pentagon, or a polygon with rounded corners, or an ellipse or a circle. The top surface shape of a sub-pixel referred to here corresponds to the top surface shape of the light-emitting area of ​​a light-emitting device.

[0519] Furthermore, if the pixel is configured to have both a light-emitting device and a light-receiving device, the pixel has a light-receiving function, allowing it to detect contact or proximity of an object while displaying an image. For example, instead of displaying an image with all of the subpixels of the light-emitting device, some of the subpixels can emit light as a light source, while the remaining subpixels display an image.

[0520] Furthermore, it is preferable that the light-receiving area of ​​the sub-pixel 702PS(i,j) is smaller than the light-emitting area of ​​the other sub-pixels. The smaller the light-receiving area, the narrower the imaging range, which allows for suppression of blur in the imaging result and improvement of resolution. Therefore, by using the sub-pixel 702PS(i,j), high-definition or high-resolution imaging can be performed. For example, the sub-pixel 702PS(i,j) can be used to perform imaging for personal authentication using fingerprints, palm prints, irises, pulse patterns (including vein patterns and arterial patterns), or faces.

[0521] Furthermore, the sub-pixel 702PS(i,j) can be used as a touch sensor (also called a direct touch sensor) or a near-touch sensor (also called a hover sensor, hover-touch sensor, non-contact sensor, or touchless sensor). For example, it is preferable that the sub-pixel 702PS(i,j) detect infrared light. This enables touch detection even in dark places.

[0522] Here, a touch sensor or near-touch sensor can detect the proximity or contact of an object (such as a finger, hand, or pen). A touch sensor can detect an object when the light-receiving device and the object are in direct contact. A near-touch sensor can detect an object even if the object does not come into contact with the light-receiving device. For example, it is preferable that the light-receiving device can detect an object when the distance between the light-receiving device and the object is in the range of 0.1 mm to 300 mm, preferably 3 mm to 50 mm. With this configuration, it becomes possible to operate the light-receiving device without the object directly touching it, in other words, it becomes possible to operate the light-receiving device without contact (touchless). With the above configuration, the risk of the light-receiving device becoming dirty or scratched can be reduced, or it becomes possible to operate the light-receiving device without the object directly touching any dirt (e.g., dust, bacteria, or viruses) attached to the light-receiving device.

[0523] Furthermore, in order to perform high-resolution imaging, it is preferable that sub-pixels 702PS(i,j) be provided on all pixels of the light-receiving device. On the other hand, when sub-pixels 702PS(i,j) are used in touch sensors or near-touch sensors, the accuracy required is not as high as when imaging fingerprints, so it is sufficient to provide them on some of the pixels of the light-receiving device. The detection speed can be increased by reducing the number of sub-pixels 702PS(i,j) in the light-receiving device to the number of sub-pixels 702R(i,j), etc.

[0524] Next, an example of a pixel circuit for a subpixel having a light-emitting device will be explained with reference to Figure 12(A). The pixel circuit 530 shown in Figure 12(A) has a light-emitting device (EL) 550, transistors M15, M16, M17, and a capacitive element C3. A light-emitting diode can be used as the light-emitting device 550. In particular, it is preferable to use the light-emitting device described in Embodiments 2 and 3 as the light-emitting device 550.

[0525] In Figure 12(A), transistor M15 has its gate electrically connected to wiring VG, one of its source or drain electrically connected to wiring VS, and the other of its source or drain electrically connected to one electrode of capacitive element C3 and the gate of transistor M16. One of the source or drain of transistor M16 is electrically connected to wiring V4, and the other is electrically connected to the anode of light-emitting device 550 and one of the source or drain of transistor M17. Transistor M17 has its gate electrically connected to wiring MS, and the other of its source or drain electrically connected to wiring OUT2. The cathode of light-emitting device 550 is electrically connected to wiring V5.

[0526] Constant potentials are supplied to wiring V4 and wiring V5, respectively. The anode side of the light-emitting device 550 can be set to a high potential, and the cathode side to a lower potential than the anode side. Transistor M15 is controlled by a signal supplied to wiring VG and functions as a selection transistor to control the selected state of the pixel circuit 530. Transistor M16 also functions as a drive transistor that controls the current flowing to the light-emitting device 550 according to the potential supplied to its gate. When transistor M15 is conducting, the potential supplied to wiring VS is supplied to the gate of transistor M16, and the luminescence brightness of the light-emitting device 550 can be controlled according to that potential. Transistor M17 is controlled by a signal supplied to wiring MS and has the function of outputting the potential between transistor M16 and the light-emitting device 550 to the outside via wiring OUT2.

[0527] Furthermore, it is preferable to use transistors in which the semiconductor layer on which the channel is formed is made of a metal oxide (oxide semiconductor) for transistors M15, M16, and M17 in the pixel circuit 530 of Figure 12(A), and transistors M11, M12, M13, and M14 in the pixel circuit 531 of Figure 12(B).

[0528] Transistors using metal oxides, which have a wider bandgap and lower carrier density than silicon, can achieve extremely low off-currents. Therefore, this low off-current allows the charge accumulated in the capacitive element connected in series with the transistor to be retained for extended periods. For this reason, it is preferable to use transistors made of oxide semiconductors, particularly for transistors M11, M12, and M15 connected in series with capacitive element C2 or C3. Similarly, using oxide semiconductor transistors for other transistors can reduce manufacturing costs.

[0529] Furthermore, transistors M11 to M17 can also be transistors in which silicon is applied as the semiconductor in which the channel is formed. In particular, using highly crystalline silicon such as single-crystal silicon or polycrystalline silicon is preferable because it can achieve high field-effect mobility, enabling faster operation.

[0530] Alternatively, a configuration may be used in which one or more transistors among transistors M11 to M17 have oxide semiconductors applied, and the others have silicon applied.

[0531] Next, an example of a pixel circuit for a subpixel having a light-receiving device will be explained with reference to Figure 12(B). The pixel circuit 531 shown in Figure 12(B) has a light-receiving device (PD) 560, transistors M11, M12, M13, M14, and a capacitive element C2. Here, an example using a photodiode as the light-receiving device (PD) 560 is shown.

[0532] In Figure 12(B), the photodetector (PD) 560 has its anode electrically connected to wiring V1 and its cathode electrically connected to either the source or drain of transistor M11. Transistor M11 has its gate electrically connected to wiring TX and its other source or drain electrically connected to one electrode of capacitive element C2, one source or drain of transistor M12, and the gate of transistor M13. Transistor M12 has its gate electrically connected to wiring RES and its other source or drain electrically connected to wiring V2. Transistor M13 has its source or drain electrically connected to wiring V3 and its other source or drain electrically connected to either the source or drain of transistor M14. Transistor M14 has its gate electrically connected to wiring SE and its other source or drain electrically connected to wiring OUT1.

[0533] Constant potentials are supplied to wirings V1, V2, and V3, respectively. When the photodetector (PD) 560 is driven in reverse bias, a higher potential is supplied to wiring V2 than to wiring V1. Transistor M12 is controlled by a signal supplied to wiring RES and has the function of resetting the potential of the node connected to the gate of transistor M13 to the potential supplied to wiring V2. Transistor M11 is controlled by a signal supplied to wiring TX and has the function of controlling the timing at which the potential of the above node changes according to the current flowing through the photodetector (PD) 560. Transistor M13 functions as an amplifying transistor that provides an output according to the potential of the above node. Transistor M14 is controlled by a signal supplied to wiring SE and functions as a selection transistor for reading the output according to the potential of the above node with an external circuit connected to wiring OUT1.

[0534] Note that in Figures 12(A) and 12(B), the transistors are shown as n-channel transistors, but p-channel transistors can also be used.

[0535] It is preferable that the transistors in pixel circuit 530 and pixel circuit 531 be formed side by side on the same substrate. In particular, it is preferable to configure the transistors in pixel circuit 530 and pixel circuit 531 to be mixed within a single region and arranged periodically.

[0536] Furthermore, it is preferable to provide one or more layers having either or both transistors and / or capacitive elements in a position that overlaps with the light-receiving device (PD) 560 or the light-emitting device (EL) 550. This reduces the effective area occupied by each pixel circuit, enabling the realization of a high-definition light-receiving or display unit.

[0537] Next, Figure 12(C) shows an example of a specific transistor structure that can be applied to the pixel circuit described in Figures 12(A) and 12(B). Note that bottom-gate transistors or top-gate transistors can be used as appropriate.

[0538] The transistor shown in Figure 12(C) has a semiconductor film 508, a conductive film 504, an insulating film 506, a conductive film 512A, and a conductive film 512B. The transistor is formed, for example, on an insulating film 501C. The transistor also has an insulating film 516 (insulating film 516A and insulating film 516B) and an insulating film 518.

[0539] The semiconductor film 508 has a region 508A that is electrically connected to the conductive film 512A, and a region 508B that is electrically connected to the conductive film 512B. The semiconductor film 508 has a region 508C between regions 508A and 508B.

[0540] The conductive film 504 has a region that overlaps with region 508C, and the conductive film 504 has the function of a gate electrode.

[0541] The insulating film 506 has a region sandwiched between the semiconductor film 508 and the conductive film 504. The insulating film 506 functions as a first gate insulating film.

[0542] The conductive film 512A has either the function of a source electrode or the function of a drain electrode, and the conductive film 512B has either the function of a source electrode or the function of a drain electrode.

[0543] Furthermore, the conductive film 524 can be used in a transistor. The conductive film 524 has a region in which the semiconductor film 508 is sandwiched between it and the conductive film 504. The conductive film 524 functions as a second gate electrode. The insulating film 501D is sandwiched between the semiconductor film 508 and the conductive film 524 and functions as a second gate insulating film.

[0544] The insulating film 516 functions, for example, as a protective film covering the semiconductor film 508. Specifically, the insulating film 516 can include films containing silicon oxide, silicon oxide nitride, silicon nitride, silicon nitride, aluminum oxide, hafnium oxide, yttrium oxide, zirconium oxide, gallium oxide, tantalum oxide, magnesium oxide, lanthanum oxide, cerium oxide, or neodymium oxide.

[0545] The insulating film 518 is preferably made of a material that has the function of suppressing the diffusion of, for example, oxygen, hydrogen, water, alkali metals, alkaline earth metals, etc. Specifically, as the insulating film 518, for example, silicon nitride, silicon oxynitride, aluminum nitride, aluminum oxynitride, etc. are available. Furthermore, it is preferable that the number of nitrogen atoms is greater than the number of oxygen atoms in silicon oxynitride and aluminum oxynitride, respectively.

[0546] Furthermore, in the process of forming the semiconductor film used for the transistors in the pixel circuit, the semiconductor film used for the transistors in the drive circuit can also be formed. For example, a semiconductor film with the same composition as the semiconductor film used for the transistors in the pixel circuit can be used in the drive circuit.

[0547] Furthermore, the semiconductor film 508 can be made of a semiconductor containing elements of Group 14. Specifically, a semiconductor containing silicon can be used for the semiconductor film 508.

[0548] Furthermore, hydrogenated amorphous silicon can be used for the semiconductor film 508. Alternatively, microcrystalline silicon or the like can be used for the semiconductor film 508. This makes it possible to provide a device with less display unevenness compared to, for example, a device (including light-emitting devices, display panels, display devices, and light-receiving devices) that uses polysilicon for the semiconductor film 508. Alternatively, it is easier to scale up the device.

[0549] Furthermore, polysilicon can be used for the semiconductor film 508. This allows for, for example, a higher field-effect mobility of the transistor compared to a transistor using hydrogenated amorphous silicon for the semiconductor film 508. Alternatively, for example, the driving capability can be increased compared to a transistor using hydrogenated amorphous silicon for the semiconductor film 508. Alternatively, for example, the aperture ratio of the pixels can be improved compared to a transistor using hydrogenated amorphous silicon for the semiconductor film 508.

[0550] Alternatively, for example, the reliability of the transistor can be improved compared to a transistor using hydrogenated amorphous silicon as the semiconductor film 508.

[0551] Alternatively, the temperature required for transistor fabrication can be lowered compared to, for example, transistors using single-crystal silicon.

[0552] Alternatively, the semiconductor film used for the transistors in the drive circuit can be formed using the same process as the semiconductor film used for the transistors in the pixel circuit. Alternatively, the drive circuit can be formed on the same substrate as the substrate on which the pixel circuit is formed. Alternatively, the number of components constituting the electronic device can be reduced.

[0553] Furthermore, single-crystal silicon can be used for the semiconductor film 508. This allows for higher resolution than, for example, a light-emitting device (or display panel) that uses hydrogenated amorphous silicon for the semiconductor film 508. Alternatively, it is possible to provide a light-emitting device with less display unevenness than a light-emitting device that uses polysilicon for the semiconductor film 508. Alternatively, for example, smart glasses or a head-mounted display can be provided.

[0554] Furthermore, a metal oxide can be used for the semiconductor film 508. This allows the pixel circuit to hold the image signal for a longer time compared to a pixel circuit using a transistor with amorphous silicon as the semiconductor film. Specifically, the selection signal can be supplied at a frequency of less than 30 Hz, preferably less than 1 Hz, and more preferably less than once per minute, while suppressing the occurrence of flicker. As a result, fatigue accumulated in the user of the electronic device can be reduced. In addition, power consumption associated with operation can be reduced.

[0555] Furthermore, an oxide semiconductor can be used for the semiconductor film 508. Specifically, an oxide semiconductor containing indium, an oxide semiconductor containing indium, gallium, and zinc, or an oxide semiconductor containing indium, gallium, zinc, and tin can be used for the semiconductor film 508.

[0556] Furthermore, by using an oxide semiconductor as the semiconductor film, it is possible to obtain a transistor with a smaller leakage current in the off state than a transistor using amorphous silicon as the semiconductor film. Therefore, it is preferable to use a transistor using an oxide semiconductor as the semiconductor film for a switch or the like. Moreover, a circuit using a transistor with an oxide semiconductor as the semiconductor film as a switch can maintain the potential of the floating node for a longer time than a circuit using a transistor with an amorphous silicon as the semiconductor film as a switch.

[0557] When an oxide semiconductor is used as the semiconductor film, the light-receiving device 720 has a configuration in which an oxide semiconductor is used as the semiconductor film and a light-emitting device with an MML (metal maskless) structure. This configuration makes it possible to make the leakage current that can flow through the transistor and the leakage current that can flow between adjacent light-emitting elements (also called lateral leakage current or side leakage current) extremely low. Furthermore, with the above configuration, when an image is displayed on the display device, the observer can observe one or more of the following: image sharpness, image clarity, high saturation, and high contrast ratio. Moreover, by making the leakage current that can flow through the transistor and the lateral leakage current between light-emitting elements extremely low, it is possible to achieve a display (also called true black display) with as little light leakage (so-called black floating) that may occur when displaying black as possible.

[0558] In particular, among light-emitting devices with an MML structure, applying the SBS structure described above results in a configuration where the layer provided between light-emitting elements (for example, an organic layer used in common between light-emitting elements, also called a common layer) is separated, making it possible to achieve a display with no side leakage or extremely low side leakage.

[0559] Next, a cross-sectional view of the light-receiving device is shown. Figure 13 shows a cross-sectional view of the light-receiving device shown in Figure 11(A).

[0560] The cross-sectional view in Figure 13 shows a portion of the region containing the FPC 713 and the wiring 706 electrically connected via the conductive material CP, and a portion of the display region 701 containing the pixel 703(i,j), when these regions are cut.

[0561] In Figure 13, the light-receiving device 700 has a functional layer 520 between the first substrate 510 and the second substrate 770. The functional layer 520 includes transistors (M11, M12, M13, M14, M15, M16, M17) and capacitive elements (C2, C3) as described in Figure 12, as well as wiring (VS, VG, V1, V2, V3, V4, V5) that electrically connect them. In Figure 13, the functional layer 520 is shown to include, but is not limited to, a pixel circuit 530X(i,j) and a pixel circuit 530S(i,j), as well as drive circuits GD, RD, and RC.

[0562] Furthermore, the pixel circuits formed on the functional layer 520 (for example, the pixel circuits 530X(i,j) and 530S(i,j) shown in Figure 13) are electrically connected to the light-emitting device and light-receiving device (for example, the light-emitting device 550X(i,j) and light-receiving device 550S(i,j) shown in Figure 13) formed on the functional layer 520. Specifically, the light-emitting device 550X(i,j) is electrically connected to the pixel circuit 530X(i,j) via wiring 591X, and the light-receiving device 550S(i,j) is electrically connected to the pixel circuit 530S(i,j) via wiring 591S. In addition, there is an insulating layer 705 on the functional layer 520, the light-emitting device, and the light-receiving device, and the insulating layer 705 has the function of bonding the functional layer 520 to the second substrate 770.

[0563] Furthermore, the second substrate 770 can be a substrate equipped with touch sensors in a matrix. For example, a substrate equipped with a capacitive touch sensor or an optical touch sensor can be used as the second substrate 770. This allows the light-receiving device according to one aspect of the present invention to be used as a touch panel.

[0564] The configuration shown in this embodiment can be used in appropriate combination with the configurations shown in other embodiments.

[0565] (Embodiment 6) In this embodiment, the configuration of an electronic device according to one aspect of the present invention will be explained with reference to Figures 14(A) to 16(B). Note that a part of the electronic device shown in this embodiment may be equipped with a light-receiving device, which is also an aspect of the present invention.

[0566] Figures 14(A) to 16(B) illustrate the configuration of an electronic device according to one embodiment of the present invention. Figure 14(A) is a block diagram of the electronic device, and Figures 14(B) to 14(E) are perspective views illustrating the configuration of the electronic device. Figures 15(A) to 15(E) are perspective views illustrating the configuration of the electronic device, and Figures 16(A) and 16(B) are perspective views illustrating the configuration of the electronic device.

[0567] The electronic device 5200B described in this embodiment includes a computing device 5210 and an input / output device 5220 (see Figure 14(A)).

[0568] The arithmetic unit 5210 has a function to receive operation information and a function to supply image information based on the operation information.

[0569] The input / output device 5220 includes a display unit 5230, an input unit 5240, a detection unit 5250, a communication unit 5290, a function for supplying operation information, and a function for supplying image information. Furthermore, the input / output device 5220 also includes a function for supplying detection information, a function for supplying communication information, and a function for receiving communication information.

[0570] The input unit 5240 has the function of supplying operation information. For example, the input unit 5240 supplies operation information based on the operation of the user of the electronic device 5200B.

[0571] Specifically, the input unit 5240 can use a keyboard, hardware buttons, pointing device, touch sensor, illuminance sensor, imaging device, voice input device, eye-tracking device, posture detection device, etc.

[0572] The display unit 5230 has the function of displaying a display panel and image information. For example, the display panel described in Embodiment 4 can be used in the display unit 5230.

[0573] The detection unit 5250 has the function of supplying detection information. For example, it has the function of detecting the surrounding environment in which electronic equipment is being used and supplying it as detection information.

[0574] Specifically, illuminance sensors, imaging devices, posture detection devices, pressure sensors, human presence sensors, etc., can be used in the detection unit 5250.

[0575] The communication unit 5290 has functions for receiving and supplying communication information. For example, it has functions for connecting with other electronic devices or communication networks via wireless or wired communication. Specifically, it has functions such as wireless local area communication, telephone communication, and short-range wireless communication.

[0576] Figure 14(B) shows an electronic device having an external shape that follows a cylindrical column or the like. One example is digital signage. A display panel, which is one aspect of the present invention, can be applied to the display unit 5230. It may also have a function to change the display method according to the illumination of the usage environment. It may also have a function to change the display content when a person is detected. This allows it to be installed, for example, on a building column, or to display advertisements or information, or to be used in digital signage, etc.

[0577] Figure 14(C) shows an electronic device that has the function of generating image information based on the trajectory of a pointer used by the user. Examples include electronic whiteboards, electronic bulletin boards, and electronic signboards. Specifically, a display panel with a diagonal length of 20 inches or more, preferably 40 inches or more, and more preferably 55 inches or more can be used. Alternatively, multiple display panels can be arranged to form a single display area. Alternatively, multiple display panels can be arranged to form a multi-screen.

[0578] Figure 14(D) shows an electronic device that can receive information from other devices and display it on the display unit 5230. One example is a wearable electronic device. Specifically, it can display several options, or the user can select several options and send them back to the information sender. Alternatively, it can have a function to change the display method according to the illumination of the usage environment. This can reduce the power consumption of the wearable electronic device, for example. Alternatively, it can display images on the wearable electronic device so that it can be used suitably even in environments with strong ambient light, such as outdoors on a sunny day.

[0579] Figure 14(E) shows an electronic device having a display unit 5230 with a curved surface that gently curves along the side of the housing. One example is a mobile phone. The display unit 5230 includes a display panel, which has the function of displaying on, for example, the front, side, top, and back. This allows information to be displayed not only on the front of the mobile phone, but also on the sides, top, and back.

[0580] Figure 15(A) shows an electronic device that can receive information from the internet and display it on the display unit 5230. One example is a smartphone. For example, a message that has been created can be viewed on the display unit 5230. Alternatively, a message that has been created can be sent to another device. Alternatively, for example, it has a function to change the display method according to the illumination of the usage environment. This can reduce the power consumption of the smartphone. Alternatively, for example, an image can be displayed on the smartphone so that it can be used suitably even in environments with strong ambient light, such as outdoors on a sunny day.

[0581] Figure 15(B) shows an electronic device that can use a remote controller as an input unit 5240. One example is a television system. Alternatively, it can receive information from a broadcasting station or the internet and display it on the display unit 5230. Alternatively, it can photograph the user using the detection unit 5250. Alternatively, it can transmit the user's video. Alternatively, it can acquire the user's viewing history and provide it to a cloud service. Alternatively, it can acquire recommendation information from a cloud service and display it on the display unit 5230. Alternatively, it can display a program or video based on the recommendation information. Alternatively, it can have a function to change the display method according to the illumination of the usage environment. This allows the video to be displayed on the television system in a way that is suitable for use even when strong sunlight shines into the room on a sunny day.

[0582] Figure 15(C) shows an electronic device that can receive educational materials from the internet and display them on the display unit 5230. One example is a tablet computer. Alternatively, a report can be entered using the input unit 5240 and sent to the internet. Alternatively, the correction results or evaluations of the report can be obtained from a cloud service and displayed on the display unit 5230. Alternatively, appropriate educational materials can be selected and displayed based on the evaluation.

[0583] For example, the display unit 5230 can receive image signals from other electronic devices and display them. Alternatively, it can be propped up on a stand or the like and used as a sub-display. This allows images to be displayed on the tablet computer in a way that is suitable for use even in environments with strong ambient light, such as outdoors on a sunny day.

[0584] Figure 15(D) shows an electronic device having multiple display units 5230. One example is a digital camera. For example, the detection unit 5250 can capture images while displaying them on the display units 5230. Alternatively, the captured images can be displayed on the detection unit. Alternatively, the input unit 5240 can be used to add embellishments to the captured images. Alternatively, messages can be attached to the captured images. Alternatively, the images can be transmitted to the internet. Alternatively, the device has a function to change the shooting conditions according to the illumination of the environment in which they are used. This allows the subject to be displayed on the digital camera in a way that allows for suitable viewing even in environments with strong ambient light, such as outdoors on a sunny day.

[0585] Figure 15(E) shows an electronic device that can control other electronic devices by using the electronic device of this embodiment as a master and using other electronic devices as slaves. One example is a portable personal computer. For example, part of the image information can be displayed on the display unit 5230 and the other part of the image information can be displayed on the display unit of the other electronic device. Alternatively, an image signal can be supplied. Alternatively, information to be written can be obtained from the input unit of the other electronic device using the communication unit 5290. This allows for the use of a wide display area, for example, with a portable personal computer.

[0586] Figure 16(A) shows an electronic device having a detection unit 5250 that detects acceleration or direction. An example is a goggle-type electronic device. Alternatively, the detection unit 5250 can supply information relating to the user's position or the direction the user is facing. Alternatively, the electronic device can generate image information for the right eye and image information for the left eye based on the user's position or the direction the user is facing. Alternatively, the display unit 5230 has a display area for the right eye and a display area for the left eye. This allows, for example, the display of an immersive virtual reality space on a goggle-type electronic device.

[0587] Figure 16(B) shows an electronic device having an imaging device and a detection unit 5250 that detects acceleration or direction. One example is a glasses-type electronic device. Alternatively, the detection unit 5250 can supply information relating to the user's position or the direction the user is facing. Alternatively, the electronic device can generate image information based on the user's position or the direction the user is facing. This allows, for example, information to be attached to and displayed on a real-world landscape. Alternatively, images of an augmented reality space can be displayed on a glasses-type electronic device.

[0588] This embodiment can be appropriately combined with other embodiments shown in this specification. [Examples]

[0589] (Synthesis Example 1) This example describes the physical properties and synthesis method of an organic compound according to one embodiment of the present invention. Specifically, the synthesis method of N,9-diphenyl-N-(2,6,10-triphenyl-9-anthracenyl)-9H-carbazole-3-amine (abbreviated as 2,6Ph-PCAA), shown by structural formula (124) in Embodiment 1, will be described. The structure of 2,6Ph-PCAA is shown below.

[0590] [ka]

[0591] <Step 1: Synthesis of 2,6-diphenylanthracene> 5.0 g (15 mmol) of 2,6-dibromoanthracene, 4.0 g (33 mmol) of phenylboronic acid, 0.22 g (0.60 mmol) of di(1-adamantyl)-n-butylphosphine (cataCXium® A), 13 g (60 mmol) of tripotassium phosphate (K3PO4), and 0.15 L of xylene were placed in a 500 mL three-necked flask fitted with a reflux condenser, and the flask was then purged with nitrogen. 67 mg (0.30 mmol) of palladium(II) acetate (Pd(OAc)2) was added to this mixture, and the mixture was heated under reflux at 150 °C for 3 hours.

[0592] Next, after stirring, the precipitated solid was collected by suction filtration and washed with toluene, ethanol, and water. The remaining solid was dried to obtain 5.0 g of a greenish-yellow solid. The synthesis scheme for Step 1 is shown below (b-1).

[0593] [ka]

[0594] <Step 2: Synthesis of 9-bromo-2,6-diphenylanthracene> First, in step A, 2.5 g of the yellow-green solid obtained in step 1 was added to a 1 L three-necked flask with 0.50 L of N,N-dimethylformamide (DMF), and the mixture was heated and stirred at 125°C until dissolved. The resulting solution was cooled to 100°C, and 1.4 g (7.9 mmol) of N-bromosuccinimide (NBS) was added gradually over 5 minutes. The resulting mixture was stirred for 18 hours while returning to room temperature. After stirring, 0.50 L of water was added to the mixture to precipitate the solid. The obtained solid was collected by suction filtration and washed with ethanol, water, and toluene. The remaining solid was dried.

[0595] Furthermore, the 5.0g of greenish-yellow solid obtained in Step 1 was subjected to Step A in two separate steps. In other words, 2.5g of the 5.0g of greenish-yellow solid obtained in Step 1 was used in each step A. Therefore, 5.0g of the greenish-yellow solid obtained in Step 1 was used.

[0596] Next, the washed solids were combined and purified by recrystallization (toluene / ethanol). The precipitated solid was collected, washed with a small amount of toluene and hexane, and then dried to obtain 3.68 g of the target yellow solid, with a combined yield of 60% from the two reactions in Step 1 and Step 2. The synthesis scheme for Step 2 is shown below (b-2).

[0597] [ka]

[0598] <Step 3: Synthesis of 2,6,9-triphenylanthracene> 3.7 g (9.0 mmol) of 9-bromo-2,6-diphenylanthracene, 1.2 g (9.9 mmol) of phenylboronic acid, 65 mg (0.18 mmol) of di(1-adamantyl)-n-butylphosphine (cataCXium(R) A), 3.8 g (18 mmol) of tripotassium phosphate (K3PO4), and 60 mL of xylene were placed in a 200 mL three-necked flask fitted with a reflux condenser, and the flask was then purged with nitrogen. 20 mg (89 μmol) of palladium(II) acetate (Pd(OAc)2) was added to this mixture, and the mixture was heated under reflux at 150 °C for 3 hours.

[0599] Next, after stirring, the precipitated solid was recovered by suction filtration and washed with toluene, ethanol, and water. The obtained solid was dried to obtain 4.0 g of a brown solid containing impurities. The synthesis scheme for Step 3 is shown below (b-3).

[0600] [ka]

[0601] <Step 4: Synthesis of 9-bromo-2,6,10-triphenylanthracene> In a 300 mL three-necked flask, 4.0 g of the brown solid containing impurities obtained in Step 3, 90 mL of N,N-dimethylformamide (DMF), and 0.10 L of toluene were added, and the mixture was stirred while cooling to 0°C. To the resulting mixture, 2.0 g (11 mmol) of N-bromosuccinimide (NBS) was gradually added, and the mixture was stirred for 25 hours while returning it to room temperature. After stirring, 0.50 L of water was added to the mixture, and the aqueous layer was extracted with toluene.

[0602] The obtained organic layer was washed twice with water, followed by washing with saturated brine. The organic layer was dried over magnesium sulfate. The resulting mixture was filtered by gravity to remove the magnesium sulfate. The resulting filtrate was concentrated and dried to obtain 3.8 g of an orange-yellow solid. This orange-yellow solid was purified by high-performance liquid chromatography (mobile phase: chloroform) to obtain 2.8 g of a yellow solid containing impurities. The synthesis scheme for step 4 is shown below (b-4).

[0603] [ka]

[0604] <Step 5: Synthesis of 2,6Ph-PCAA> 1.2 g of the yellow solid obtained in step 4, along with 0.84 g (2.5 mmol) of N,9-diphenyl-9H-carbazole-3-amine, 0.48 g (5.0 mmol) of sodium t-butoxide (t-BuONa), 0.30 mL of tri(t-butyl)phosphine ((t-Bu)3P), and 15 mL of xylene were placed in a 200 mL three-necked flask fitted with a reflux condenser, and the flask was then purged with nitrogen. Subsequently, 14 mg (25 μmol) of bis(dibenzylideneacetone)palladium(O) (Pd(dba)2) was added to the three-necked flask, and the mixture was stirred at 150 °C for 7 hours.

[0605] After stirring, water was added to the mixture, and the aqueous layer was extracted with toluene. The resulting organic layer was washed twice with water, followed by washing with saturated brine. The organic layer was dried over magnesium sulfate. The resulting mixture was filtered naturally to remove the magnesium sulfate. The resulting filtrate was concentrated and dried to obtain 2.2 g of an orange solid.

[0606] The orange solid obtained above was purified by recrystallization (toluene / ethanol) to obtain 2.1 g of orange solid. This orange solid was further purified by silica gel chromatography (hexane and toluene were used as the developing solvents. The ratio of hexane to toluene was initially hexane:toluene = 4:1, followed by hexane:toluene = 2:1) and recrystallization (toluene / hexane) to obtain 1.2 g of the target orange solid (yield 65%).

[0607] Next, the obtained 1.2 g of solid was purified by sublimation using the train sublimation method. Sublimation purification was performed by heating the solid for 16 hours at a pressure of 3.2 Pa and a temperature range of 300°C to 290°C while flowing argon at 5 mL / min. After sublimation purification, 0.89 g of orange solid was obtained with a recovery rate of 77%. The synthesis scheme for Step 5 is shown below (b-5).

[0608] [ka]

[0609] The obtained solid 1 The 1H NMR spectra are shown in Figures 17(A) and 17(B). 1 The results of the 1H NMR measurement are shown below. This shows that 2,6Ph-PCAA (structural formula (124)) was obtained in this synthesis example.

[0610] 1H NMR (dichloromethane-d2,500MHz): δ=8.59(d,J=1.7Hz,1H), 8.44(d,J=9.2Hz,1H), 8.12(d,J=2.3Hz,1H), 7.96-7.94(m,2H), 7.81(d,J=9.2Hz, 1H), 7.72(dd,J=9.2Hz,1.7Hz,1H), 7.69-7.52(m,14H), 7.47-7.28(m,11H), 7.22-7.17(m,3H), 7.12-7.10(m,2H), 6.87(t,J=7.4Hz,1H)

[0611] <Measurement of physical properties> Next, Figure 18 shows the results of measuring the absorption and emission spectra of a toluene solution of 2,6Ph-PCAA.

[0612] To measure the absorption spectrum of the toluene solution, a UV-Vis spectrophotometer (V-770DS, JASCO Corporation) was used, and the spectrum obtained by measuring toluene alone in a quartz cell was subtracted. For the emission spectrum, a spectrofluorometer (FP-8600DS, JASCO Corporation) was used.

[0613] As shown in Figure 18, the toluene solution of 2,6Ph-PCAA showed an absorption peak around 470 nm, and the emission wavelength peak was 570 nm (excitation wavelength 470 nm).

[0614] Next, the HOMO and LUMO levels of 2,6Ph-PCAA were calculated based on cyclic voltammetry (CV) measurements, and the calculation method is shown below.

[0615] An electrochemical analyzer (manufactured by BAS Corporation, model number: ALS Model 600A or 600C) was used as the measuring device. For the CV measurement, the solution was prepared by dissolving anhydrous dimethylformamide (DMF) (manufactured by Aldrich Corporation, 99.8%, catalog number: 22705-6) as the solvent, dissolving tetra-n-butylammonium perchlorate (n-Bu4NClO4) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) as the supporting electrolyte to a concentration of 100 mmol / L, and then dissolving the target substance to a concentration of 2 mmol / L. A platinum electrode (manufactured by BAS Corporation, PTE platinum electrode) was used as the working electrode, a platinum electrode (manufactured by BAS Corporation, VC-3 Pt counter electrode (5cm)) was used as the auxiliary electrode, and Ag / Ag was used as the reference electrode. + Each electrode (RE7 non-aqueous solvent reference electrode, manufactured by BAS Corporation) was used.

[0616] Furthermore, the measurements were performed at room temperature (20-25°C). The scan speed during CV measurement was standardized to 0.1 V / sec, and the oxidation potential Ea [V] and reduction potential Ec [V] with respect to the reference electrode were measured. Ea was defined as the intermediate potential of the oxidation-reduction wave, and Ec was defined as the intermediate potential of the reduction-oxidation wave. Here, since the potential energy of the reference electrode used in this embodiment with respect to the vacuum level is known to be -4.94 [eV], the HOMO level [eV] = -4.94 - Ea and the LUMO level [eV] = -4.94 - Ec can be used to determine the HOMO level and LUMO level, respectively.

[0617] The CV measurement was repeated 100 times, and the oxidation-reduction wave at the 100th cycle was compared with the oxidation-reduction wave at the 1st cycle to investigate the electrical stability of the compound.

[0618] As a result, it was found that the HOMO level of 2,6Ph-PCAA is -5.37 eV and the LUMO level is -2.93 eV. Furthermore, when comparing the waveforms after 1 cycle and 100 cycles in repeated oxidation-reduction wave measurements, the peak intensity was maintained at 90% in the Ea measurement and 93% in the Ec measurement, confirming that 2,6Ph-PCAA has very good resistance to oxidation and reduction.

[0619] Furthermore, thermogravimetric analysis-differential thermal analysis (TG-DTA) was performed on 2,6Ph-PCAA. A high-vacuum differential thermal balance (Bruker AXS Corporation, TG-DTA2410SA) was used for the measurements.

[0620] The measurements were performed at atmospheric pressure, under conditions of a heating rate of 10°C / min and a nitrogen stream (flow rate of 200 mL / min).

[0621] Thermogravimetric-differential thermal analysis revealed that 2,6Ph-PCAA has a decomposition temperature of 460°C at which its weight, determined by thermogravimetric analysis, becomes 5% of its initial weight, indicating that it is a substance with high heat resistance.

[0622] In addition, differential scanning calorimetry (DSC) was performed on 2,6Ph-PCAA using a PerkinElmer DSC8500. The differential scanning calorimetry involved heating the sample from -10°C to 350°C at a heating rate of 40°C / min, holding it at that temperature for 3 minutes, and then cooling it down to -10°C at a cooling rate of 100°C / min. This process was repeated twice in succession.

[0623] DSC measurement results from the second cycle revealed that the glass transition temperature of 2,6Ph-PCAA is 170°C, indicating that it is a material with extremely high heat resistance. [Examples]

[0624] (Synthesis Example 2) This example describes the physical properties and synthesis method of an organic compound according to one embodiment of the present invention. Specifically, the synthesis method of N-(2,6,10-triphenyl-9-anthracenyl)-bis(9-phenyl-9H-carbazole-3-yl)amine (abbreviated as 2,6Ph-PC2APhA), shown by structural formula (116) in Embodiment 1, will be described. The structure of 2,6Ph-PC2APhA is shown below.

[0625] [ka]

[0626] <Step 1: Synthesis of 9-phenyl-9H-carbazole-3-t-butoxycarbonylamine> 2.5 g (6.8 mmol) of 3-iodo-9-phenylcarbazole, 0.89 g (7.6 mmol) of tert-butyl carbamate, 4.4 g (14 mmol) of cesium carbonate (Cs2CO3), 78 mg (0.13 mmol) of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos), and 35 mL of 1,4-dioxane were placed in a 200 mL three-necked flask fitted with a reflux condenser, and the flask was purged with nitrogen. 45 mg (0.20 mmol) of palladium(II) acetate (Pd(OAc)2) was added to the flask, and the mixture was stirred at 110 °C for 20 hours.

[0627] After stirring, water was added to the mixture, and the aqueous layer was extracted with ethyl acetate. The resulting organic layer was washed twice with water, followed by washing with saturated brine. The organic layer was dried over magnesium sulfate. The resulting mixture was filtered naturally to remove the magnesium sulfate. The resulting filtrate was concentrated and dried to obtain 2.9 g of a brown solid.

[0628] The above brown solid was recrystallized (solvent: acetone / hexane / toluene), and purified by silica gel chromatography (hexane and ethyl acetate were used as developing solvents. The ratio of hexane to ethyl acetate was initially hexane:ethyl acetate = 10:1, then switched to hexane:ethyl acetate = 5:1) to obtain 1.0 g of the target yellow solid (yield 42%). The synthesis scheme for Step 1 is shown below (c-1).

[0629] [ka]

[0630] The yellow solid obtained in Step 1 1 The 1H NMR spectra are shown in Figures 19(A) and 19(B). 1 The results of the 1H NMR measurement are shown below. This confirms that the target compound was obtained in this synthesis example.

[0631] 1 ¹H NMR (dichloromethane - d2, 500MHz): δ=8.24 (br, 1H), 8.12 (d, J=7.4Hz, 1H), 7.64-7.56 (m, 4H), 7.48 (t, J=7.4Hz, 1H), 7.41-7.40 (m, 2H), 7.35-7.25 (m, 3H), 6.67 (br, 1H), 1.54 (s, 9H)

[0632] <Step 2: Synthesis of 9-phenyl-9H-carbazole-3-amine> 1.0 g (2.9 mmol) of 9-phenyl-9H-carbazole-3-t-butoxycarbonylamine and 50 mL of dichloromethane (CH2Cl2) were added to a 200 mL round-bottom flask and stirred. 3.3 g (29 mmol) of trifluoroacetic acid (TFA) was added dropwise to the flask, and the mixture was stirred at room temperature for 22 hours.

[0633] After stirring, water was added to the resulting reaction solution, and the aqueous layer was extracted with dichloromethane. The organic layer was washed twice with water, followed by washing with saturated brine. The organic layer was dried over magnesium sulfate. The resulting mixture was filtered by gravity to remove the magnesium sulfate. The resulting filtrate was concentrated and dried to obtain 0.71 g (96% yield) of the target brown solid. The synthesis scheme for Step 2 is shown below (c-2).

[0634] [ka]

[0635] <Step 3: Synthesis of bis(9-phenyl-9H-carbazole-3-yl)amine> 0.71 g (2.8 mmol) of 9-phenyl-9H-carbazole-3-amine, 1.0 g (2.8 mmol) of 3-iodo-9-phenylcarbazole, 0.53 g (5.5 mmol) of sodium t-butoxide (t-BuONa), 0.25 mL of tri(t-butyl)phosphine ((t-Bu)3P), and 15 mL of toluene were placed in a 200 mL three-necked flask fitted with a reflux condenser, and the inside of the three-necked flask was purged with nitrogen.

[0636] Next, 15 mg (28 μmol) of bis(dibenzylideneacetone)palladium(O)(Pd(dba)2) was added to the three-necked flask, and the mixture was stirred at 50°C for 2 hours. After stirring, water was added to the mixture, and the aqueous layer was extracted with toluene. The resulting organic layer was washed twice with water, followed by washing with saturated brine. The organic layer was dried over magnesium sulfate. The resulting mixture was filtered by gravity to remove the magnesium sulfate.

[0637] The filtrate obtained above was concentrated and dried to obtain 1.6 g of a brown solid. The obtained solid was purified by silica gel chromatography (hexane and toluene were used as the developing solvents. The ratio of hexane to toluene was initially hexane:toluene = 4:1, followed by hexane:toluene = 4:3, and then hexane:toluene = 1:4) to obtain 1.0 g (yield 73%) of the target pale yellow solid. The synthesis scheme for Step 3 is shown below (c-3).

[0638] [ka]

[0639] <Step 4: Synthesis of 2,6Ph-PC2APhA> 1.1 g (2.2 mmol) of 9-bromo-2,6,10-triphenylanthracene, 1.0 g (2.0 mmol) of bis(9-phenyl-9H-carbazole-3-yl)amine, 0.38 g (4.0 mmol) of sodium t-butoxide (t-BuONa), 0.20 mL of tri(t-butyl)phosphine ((t-Bu)3P), and 15 mL of xylene were placed in a 200 mL three-necked flask fitted with a reflux condenser, and the flask was then purged with nitrogen. Subsequently, 12 mg (20 μmol) of bis(dibenzylideneacetone)palladium(O) (Pd(dba)2) was added to the flask, and the mixture was stirred at 150 °C for 1 hour.

[0640] After stirring, water was added to the mixture, and the aqueous layer was extracted with toluene. The resulting organic layer was washed twice with water, followed by washing with saturated brine. The organic layer was dried over magnesium sulfate. The resulting mixture was filtered by gravity to remove the magnesium sulfate. The filtrate was concentrated, and the resulting solid was purified by silica gel chromatography (using hexane and toluene as developing solvents; initially treated with a hexane:toluene ratio of 4:1, then with a hexane:toluene ratio of 2:1), recrystallization (toluene / hexane), and high-performance liquid chromatography (mobile phase: chloroform) to obtain 0.97 g of the target red solid (yield 53%).

[0641] Next, 0.93 g of the red solid was purified by sublimation using the train sublimation method. Sublimation purification was performed by heating the solid for 24 hours at a pressure of 2.6 Pa and a temperature range of 365°C to 350°C while flowing argon at 10 mL / min. After sublimation purification, 0.72 g of the red solid was obtained with a recovery rate of 78%. The synthesis scheme for Step 4 is shown below (c-4).

[0642] [ka]

[0643] The yellow solid obtained in step 4 1 The 1H NMR spectra are shown in Figures 20(A) and 20(B). 1 The results of the 1H NMR measurement are shown below. This indicates that 2,6Ph-PC2APhA was obtained in this synthesis example.

[0644] 1 H NMR (dichloromethane-d2,500MHz): δ=8.75(d,J=1.7Hz,1H), 8.57(d,J=9.2Hz,1H), 8.01(d,J=1.7Hz,2H), 7.97(d,J=1.7H) z,1H), 7.90(d,J=7.5Hz,2H), 7.83(d,J=9.2Hz,1H), 7.71-7.51(m,19H), 7.46-7.23(m,16H), 7.15(t,J=7.5Hz,2H)

[0645] <Measurement of physical properties> Next, Figure 21 shows the results of measuring the absorption and emission spectra of a toluene solution of 2,6Ph-PC2APhA.

[0646] To measure the absorption spectrum of the toluene solution, a UV-Vis spectrophotometer (V-770DS, JASCO Corporation) was used, and the spectrum obtained by measuring toluene alone in a quartz cell was subtracted. For the emission spectrum, a spectrofluorometer (FP-8600DS, JASCO Corporation) was used.

[0647] As shown in Figure 21, the toluene solution of 2,6Ph-PC2APhA showed an absorption peak around 504 nm, and the emission wavelength peak was 604 nm (excitation wavelength 504 nm).

[0648] Next, the HOMO and LUMO levels of 2,6Ph-PC2APhA were calculated based on cyclic voltammetry (CV) measurements, and the calculation method is shown below.

[0649] An electrochemical analyzer (manufactured by BAS Corporation, model number: ALS Model 600A or 600C) was used as the measuring device. For the CV measurement, the solution was prepared by dissolving anhydrous dimethylformamide (DMF) (manufactured by Aldrich Corporation, 99.8%, catalog number: 22705-6) as the solvent, dissolving tetra-n-butylammonium perchlorate (n-Bu4NClO4) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) as the supporting electrolyte to a concentration of 100 mmol / L, and then dissolving the target substance to a concentration of 2 mmol / L. A platinum electrode (manufactured by BAS Corporation, PTE platinum electrode) was used as the working electrode, a platinum electrode (manufactured by BAS Corporation, VC-3 Pt counter electrode (5cm)) was used as the auxiliary electrode, and Ag / Ag was used as the reference electrode. + Each electrode (RE7 non-aqueous solvent reference electrode, manufactured by BAS Corporation) was used.

[0650] The measurements were performed at room temperature (20-25°C). The scan speed during CV measurement was standardized to 0.1 V / sec, and the oxidation potential Ea [V] and reduction potential Ec [V] relative to the reference electrode were measured. Ea was defined as the intermediate potential of the oxidation-reduction wave, and Ec was defined as the intermediate potential of the reduction-oxidation wave. Here, since the potential energy of the reference electrode used in this embodiment relative to the vacuum level is known to be -4.94 [eV], the HOMO level [eV] = -4.94 - Ea and the LUMO level [eV] = -4.94 - Ec can be used to determine the HOMO level and LUMO level, respectively.

[0651] The CV measurement was repeated 100 times, and the oxidation-reduction wave at the 100th cycle was compared with the oxidation-reduction wave at the 1st cycle to investigate the electrical stability of the compound.

[0652] As a result, it was found that the HOMO level of 2,6Ph-PC2APhA is -5.21 eV and the LUMO level is -2.91 eV. Furthermore, when comparing the waveforms after 1 cycle and 100 cycles in repeated oxidation-reduction wave measurements, the peak intensity was maintained at 95% in the Ea measurement and 88% in the Ec measurement, confirming that 2,6Ph-PCAA has very good resistance to oxidation and reduction.

[0653] Furthermore, thermogravimetric analysis-differential thermal analysis (TG-DTA) was performed on 2,6Ph-PC2APhA. A high-vacuum differential thermal balance (Bruker AXS Corporation, TG-DTA2410SA) was used for the measurements. The measurements were performed at atmospheric pressure, with a heating rate of 10°C / min and under a nitrogen stream (flow rate of 200 mL / min).

[0654] Thermogravimetric-differential thermal analysis revealed that 2,6Ph-PC2APhA has a decomposition temperature (temperature at which its weight, determined by thermogravimetric analysis, becomes -5% of its initial weight) of 500°C or higher, indicating that it is a substance with high heat resistance.

[0655] Furthermore, differential scanning calorimetry (DSC) was performed on 2,6Ph-PC2APhA using a PerkinElmer DSC8500. The differential scanning calorimetry involved heating the sample from -10°C to 365°C at a heating rate of 40°C / min, holding it at that temperature for 3 minutes, and then cooling it down to -10°C at a cooling rate of 100°C / min. This process was repeated twice in succession.

[0656] DSC measurement results from the second cycle revealed that the glass transition temperature of 2,6Ph-PC2APhA is 205°C, demonstrating that it is a material with extremely high heat resist...

Claims

1. An organic compound represented by general formula (G1): 【Chemical 1】 (In the formula, A １ represents any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 13 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, and a substituted or unsubstituted diarylamino group. １ ~Ar ４ each independently represents one of a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, or a substituted or unsubstituted diarylamino group. １ or Ar １ ~Ar ４ The two aryl groups in the substituted or unsubstituted diarylamino group are each independently either a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms. The two aryl groups may be bonded to each other to form a ring. １ ~R ６ each independently represents any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 13 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, and a substituted or unsubstituted alkoxy group having 1 to 13 carbon atoms, and all of the hydrogen atoms in General Formula (G1) may be deuterium.

2. An organic compound represented by general formula (G2): 【Chemistry 2】 (In the formula, A １ represents any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 13 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, and a substituted or unsubstituted diarylamino group. １ ~Ar ３ each independently represents one of a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, or a substituted or unsubstituted diarylamino group. １ or Ar １ ~Ar ３ The two aryl groups in the substituted or unsubstituted diarylamino group are each independently a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms. The two aryl groups may be bonded to each other to form a ring. ５ represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 25 carbon atoms, and n represents an integer of 0 to 2. ６ or Ar ７ each independently represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms. ６ and Ar ７ may be bonded to each other to form a ring. ５ and Ar ６ And, Ar ５ and Ar ７ may be bonded to each other to form a ring. ５ Among the groups included in ６ and a group adjacent thereto, or Ar ７ and the adjacent group are Ar ６ or Ar ７ may be bonded to each other to form a ring. １ ~R ６ each independently represents any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 13 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, and a substituted or unsubstituted alkoxy group having 1 to 13 carbon atoms, and all of the hydrogen atoms in General Formula (G2) may be deuterium.

3. An organic compound represented by general formula (G3): 【Chemistry 3】 (In the formula, Ar １ ~Ar ３ each independently represents one of a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, or a substituted or unsubstituted diarylamino group. １ ~Ar ３ The two aryl groups in the substituted or unsubstituted diarylamino group are each independently a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms. The two aryl groups may be bonded to each other to form a ring. ５ represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 25 carbon atoms, and n represents an integer of 0 to 2. ６ or Ar ７ each independently represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms. ６ and Ar ７ may be bonded to each other to form a ring. ５ and Ar ６ And, Ar ５ and Ar ７ may be bonded to each other to form a ring. ５ Among the groups included in ６ and a group adjacent thereto, or Ar ７ and the adjacent group are Ar ６ or Ar ７ may be bonded to each other to form a ring. １ ~R ６ and R ２０ ~R ２４ each independently represents any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 13 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, and a substituted or unsubstituted alkoxy group having 1 to 13 carbon atoms, and all of the hydrogen atoms in General Formula (G3) may be deuterium.

4. An organic compound represented by general formula (G4): 【Chemistry 4】 (In the formula, Ar １ ~Ar ３ , Ar ８ , and Ar ９ each independently represents one of a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, or a substituted or unsubstituted diarylamino group. １ ~Ar ３ , Ar ８ , and Ar ９ The two aryl groups in the substituted or unsubstituted diarylamino group are each independently a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms. The two aryl groups may be bonded to each other to form a ring. ５ represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 25 carbon atoms, and n represents an integer of 0 to 2. ６ or Ar ７ each independently represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms. ６ and Ar ７ may be bonded to each other to form a ring. ５ and Ar ６ And, Ar ５ and Ar ７ may be bonded to each other to form a ring. ５ Among the groups included in ６ and a group adjacent thereto, or Ar ７ and the adjacent group are Ar ６ or Ar ７ may be bonded to each other to form a ring. １ ~R ６ and R ２０ ~R ２４ each independently represents any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 13 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, and a substituted or unsubstituted alkoxy group having 1 to 13 carbon atoms, and all of the hydrogen atoms in general formula (G4) may be deuterium.

5. An organic compound represented by general formula (G5): 【Chemistry 5】 (In the formula, A １ represents any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 13 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, and a substituted or unsubstituted diarylamino group. １ ~Ar ３ each independently represents one of a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, or a substituted or unsubstituted diarylamino group. １ or Ar １ ~Ar ３ The two aryl groups in the substituted or unsubstituted diarylamino group are each independently a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms. The two aryl groups may be bonded to each other to form a ring. １０ represents any one of a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 13 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms. １ ~R １４ each independently represents any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 13 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, and a substituted or unsubstituted alkoxy group having 1 to 13 carbon atoms, and all of the hydrogen atoms in general formula (G5) may be deuterium.

6. An organic compound represented by general formula (G6): 【Chemistry 6】 (In the formula, R １ ~R １４ , and R ２０ ~R ４４ each independently represents any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 13 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms, and a substituted or unsubstituted alkoxy group having 1 to 13 carbon atoms.

7. A light emitting and receiving device comprising the organic compound according to claim 1 .

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