Organic compound and synthesis method thereof

Abstract

Provided are: an organic compound of a 1, 10-phenanthroline derivative or a 2, 2 '-dipyridyl derivative, which has substituents at symmetrical positions and which are different from each other; and a method for synthesizing the organic compound of the 1, 10-phenanthroline derivative or the 2, 2'-dipyridyl derivative. Provided is an organic compound represented by general formula (G1) or general formula (G2). In general formula (G1) or general formula (G2), any one of X2 to X5 and X6 to X9 is a halogen or a trifluoromethanesulfonyl group, and the others are hydrogen. In addition, any one of R2 to R5 or R6 to R9 is an aliphatic cyclic amino group. Note that the position of a carbon substituted by a halogen or a trifluoromethanesulfonyl group and the position of a carbon substituted by an aliphatic cyclic amino group are axisymmetric positions in the main skeleton (1, 10-phenanthroline skeleton or 2, 2 '-bipyridine skeleton).

Description

Technical Field

[0001] One aspect of the present invention relates to an organic compound, an organic electronic device, a light-emitting device, an organic EL device, an electronic device, and a method for synthesizing the organic compound.

[0002] Note that one aspect of the present invention is not limited to the technical fields described above. Examples of technical fields encompassing one aspect of the present invention include compounds, light-emitting devices, organic EL devices, semiconductor devices, display devices, light-emitting devices, energy storage devices, memory devices, electronic devices, lighting devices, input devices (e.g., touch sensors), input / output devices (e.g., touch panels), and methods for driving or manufacturing such devices. Background Technology

[0003] In recent years, display devices have been expected to be used for a variety of purposes. Examples of applications as large display devices include home television sets (also known as televisions or television receivers), digital signage, and public information displays (PIDs). Furthermore, as portable information terminals, smartphones and tablets with touch panels are under development.

[0004] In addition, there is a demand for high-definition display devices. Development of devices requiring high-definition displays, such as those for Virtual Reality (VR), Augmented Reality (AR), Substitutional Reality (SR), and Mixed Reality (MR), is very active.

[0005] As display devices, light-emitting devices, including light-emitting devices (also known as light-emitting elements), have been developed. Light-emitting devices that utilize the electroluminescence (EL) phenomenon (also known as organic "EL devices" or "light-emitting devices") have the characteristics of being easy to achieve in thin and lightweight form; being able to respond to input signals at high speed; and being able to be driven by DC constant voltage power supplies, etc., and have been applied to display devices.

[0006] Although displays or lighting devices using light-emitting devices are suitable for a wide variety of electronic devices, both materials and devices are still under continuous research and development in pursuit of light-emitting devices with better characteristics (see, for example, Patent Document 1).

[0007] [Patent Document 1] Chinese Patent No. 111943949 Specification

[0008] [Non-patent document 1] AbelAnton S et a1, "1,10-Phenanthroline Carboxylic Acids for Preparation of Functionalized Metal-Organic Frameworks", Asian Journal of Organic Chemistry, 2019, 8(11), pp.2128-2142 Summary of the Invention

[0009] One objective of this invention is to provide a synthetic method that readily introduces different substituents into symmetrical positions of 1,10-phenanthroline derivatives or 2,2'-bipyridine derivatives.

[0010] Another aspect of the present invention aims to provide an organic compound in which different substituents are introduced into symmetrical positions of a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative. Another aspect of the present invention aims to provide an organic compound in which an aliphatic cyclic amino group is introduced into one of the symmetrical positions of a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative, and a substituent different from the aliphatic cyclic amino group (hereinafter also referred to as substituent A) is introduced into the other symmetrical position.

[0011] Another objective of the present invention is to provide a novel phenanthroline derivative or bipyridine derivative. Furthermore, another objective of the present invention is to provide a method for synthesizing a novel phenanthroline derivative or bipyridine derivative.

[0012] Note that the description of these objectives does not preclude the existence of other objectives. One aspect of the invention does not require achieving all of the above objectives. Objectives other than those described above can be understood and extracted from the description, drawings, claims, etc.

[0013] One aspect of the invention is a compound represented by general formula (G1) or general formula (G2).

[0014] [Chemical Formula 1]

[0015] In the above general formula (G1) or general formula (G2), X 2 To X 5 and X 6 To X 9 One of them is a halogen or trifluoromethanesulfonyl group, and the others are hydrogen. Additionally, R... 2 To R 5 and R 6 To R 9One of them is an aliphatic cyclic amino group represented by the following general formula (g1), and the others are hydrogen. However, the positions of the carbons substituted by the halogen or trifluoromethanesulfonyl group and the carbons substituted by the group represented by the following general formula (g1) are axially symmetric positions in the main skeleton (1,10-phenanthroline skeleton or 2,2'-bipyridine skeleton).

[0016] [Chemical Formula 2]

[0017] In the above general formula (g1), R 11 To R 18 Each of these groups independently represents hydrogen (including deuterium) or any one of the following: an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, a secondary amino group with 2 to 10 carbon atoms (substituted or unsubstituted), a monovalent aromatic group with 6 to 30 carbon atoms (substituted or unsubstituted), a heteroaryl group with 1 to 30 carbon atoms, a cyano group, a halogen, a hydroxyl group, an amide group, or a carbonyl group. p and q independently represent 0 to 3. Note that R... 11 To R 18 Any two of them can also bond with each other to form a ring.

[0018] Alternatively, another aspect of the invention is an organic compound represented by any one of general formulas (G1-1) to (G1-4).

[0019] [Chemical Formula 3]

[0020] In the above general formulas (G1-1) to (G1-4), X is a halogen or trifluoromethanesulfonyl group, and R represents an aliphatic cyclic amino group represented by the following general formula (g1).

[0021] [Chemical Formula 4]

[0022] In the above general formula (g1), R 11 To R 18 Each of these groups independently represents hydrogen (including deuterium) or any one of the following: an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, a secondary amino group with 2 to 10 carbon atoms (substituted or unsubstituted), a monovalent aromatic group with 6 to 30 carbon atoms (substituted or unsubstituted), a heteroaryl group with 1 to 30 carbon atoms, a cyano group, a halogen, a hydroxyl group, an amide group, or a carbonyl group. p and q independently represent 0 to 3. Note that R... 11 To R 18 Any two of them can also bond with each other to form a ring.

[0023] Alternatively, another aspect of the invention is an organic compound represented by any one of general formulas (G2-1) to (G2-4).

[0024] [Chemical Formula 5]

[0025] In the above general formulas (G2-1) to (G2-4), X is a halogen or trifluoromethanesulfonyl group, and R represents an aliphatic cyclic amino group represented by the following general formula (g1).

[0026] [Chemical Formula 6]

[0027] In the above general formula (g1), R 11 To R 18 Each of these groups independently represents hydrogen (including deuterium) or any one of the following: an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, a secondary amino group with 2 to 10 carbon atoms (substituted or unsubstituted), a monovalent aromatic group with 6 to 30 carbon atoms (substituted or unsubstituted), a heteroaryl group with 1 to 30 carbon atoms, a cyano group, a halogen, a hydroxyl group, an amide group, or a carbonyl group. p and q independently represent 0 to 3. Note that R... 11 To R 18 Any two of them can also bond with each other to form a ring.

[0028] Alternatively, another aspect of the present invention is an organic compound represented by the general formula (G3).

[0029] [Chemical Formula 7]

[0030] In the above general formula (G3), R is a base represented by the following general formula (g1), and A is a base represented by the following general formula (g2) or the following general formula (g3). Note that in general formula (G3), substituent A and substituent R are different substituents.

[0031] [Chemical Formula 8]

[0032] In the above general formulas (g1) and (g2), R 11 To R 18 R 21 To R 28Each of these groups independently represents hydrogen (including deuterium) or any one of the following: an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, a secondary amino group with 2 to 10 carbon atoms (substituted or unsubstituted), a monovalent aromatic group with 6 to 30 carbon atoms (substituted or unsubstituted), a heteroaryl group with 1 to 30 carbon atoms, a cyano group, a halogen, a hydroxyl group, an amide group, or a carbonyl group. p, q, s, and t independently represent 0 to 3. Note that R... 11 To R 18 Any two and R 21 To R 28 Any two of them can also bond to each other to form a ring. Additionally, the aliphatic cyclic amino group represented by the above general formula (g2) can also be fused with an aromatic ring having 6 to 10 carbon atoms. In the above general formula (g3), Z represents any one of the following: a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms; a substituted or unsubstituted monovalent aromatic group having 6 to 30 carbon atoms; a substituted or unsubstituted monovalent heteroaromatic group having 1 to 30 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; a substituted or unsubstituted secondary amino group having 2 to 10 carbon atoms; a cyano group; a halogen group; a hydroxyl group; an amide group; and a carbonyl group; and m represents an integer from 1 to 3. Note that when m is 2 or more, multiple Zs can also be the same or different groups. Additionally, L represents a substituted or unsubstituted alkylene group with 1 to 3 carbon atoms, a substituted or unsubstituted cycloalkylene group with 3 to 10 carbon atoms, a substituted or unsubstituted divalent aromatic group with 6 to 25 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group with 1 to 25 carbon atoms, and n represents an integer from 0 to 3. Note that when n is 2 or higher, multiple Ls can be the same or different groups.

[0033] Another aspect of the invention is an organic compound represented by the general formula (G3-1).

[0034] [Chemical Formula 9]

[0035] In the above general formula (G3-1), R 11 To R 18 and R 21 To R 28 Each of the following groups independently represents hydrogen (including deuterium), an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, a secondary amino group with 2 to 10 carbon atoms (substituted or unsubstituted), a monovalent aromatic group with 6 to 30 carbon atoms (substituted or unsubstituted), a heteroaryl group with 1 to 30 carbon atoms, a cyano group, a halogen, a hydroxyl group, an amide group, and a carbonyl group. p, q, s, and t independently represent 0 to 3. Note that R...11 To R 18 Any two and R 21 To R 28 Any two of them can also bond to each other to form a ring. Additionally, one of the aliphatic cyclic amino groups in the above general formula (G3-1) can also fused with an aromatic ring having 6 to 10 carbon atoms. Note that in general formula (G3-1), the substituents bonded to the 4 and 7 positions of the 1,10-phenanthroline skeleton are different substituents.

[0036] Alternatively, another aspect of the present invention is an organic compound represented by the general formula (G3-2).

[0037] [Chemical Formula 10]

[0038] In the above general formula (G3-2), R 11 To R 18 Each of the following groups independently represents hydrogen (including deuterium), an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, a secondary amino group with 2 to 10 carbon atoms (substituted or unsubstituted), a monovalent aromatic group with 6 to 30 carbon atoms (substituted or unsubstituted), a heteroaryl group with 1 to 30 carbon atoms, a cyano group, a halogen, a hydroxyl group, an amide group, and a carbonyl group, with p and q independently representing 0 to 3. Note that R... 11 To R 18 Any two of them can also bond to each other to form a ring. Additionally, Z represents any one of the following: alkyl group with 1 to 10 substituted or unsubstituted carbon atoms; cycloalkyl group with 3 to 10 substituted or unsubstituted carbon atoms; monovalent aromatic group with 6 to 30 substituted or unsubstituted carbon atoms; monovalent heteroaryl group with 1 to 30 substituted or unsubstituted carbon atoms; alkoxy group with 1 to 10 substituted or unsubstituted carbon atoms; secondary amino group, cyano group, halogen group, hydroxyl group, amide group, and carbonyl group with 2 to 10 substituted or unsubstituted carbon atoms; and m represents an integer from 1 to 3. Note that when m is 2 or more, multiple Zs can also be the same or different groups. Additionally, L represents a substituted or unsubstituted alkylene group with 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkylene group with 3 to 10 carbon atoms, a substituted or unsubstituted divalent aromatic group with 6 to 25 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group with 1 to 25 carbon atoms, and n represents an integer from 0 to 3. Note that when n is 2 or higher, multiple Ls can be the same or different groups.

[0039] Another aspect of the present invention is a method for synthesizing a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative having two substituents respectively bonded to carbon at symmetrical positions and the two substituents being different from each other. The method comprises a step of reacting an 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative having two halogen or trifluoromethanesulfonyl groups respectively bonded to carbon at symmetrical positions with an aliphatic cyclic amine using an inorganic base and a solvent.

[0040] Another aspect of the present invention is a method for synthesizing a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative having two substituents respectively bonded to carbon at symmetrical positions and the substituents being different from each other. The method comprises a step of reacting a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative having two halogen or trifluoromethanesulfonate groups respectively bonded to carbon at symmetrical positions with an aliphatic cyclic amine by heating with potassium carbonate or potassium acetate and a solvent.

[0041] Another aspect of the present invention is a method for synthesizing a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative having two substituents respectively bonded to carbon at symmetrical positions and the substituents being different from each other. This method comprises the following steps: a first step, wherein a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative having two halogen or trifluoromethanesulfonate groups respectively bonded to carbon at symmetrical positions is reacted with an aliphatic cyclic amine using potassium carbonate or potassium acetate and a solvent to obtain a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative having an aliphatic cyclic amine bonded to one carbon at a symmetrical position and having a halogen or trifluoromethanesulfonate group bonded to the other carbon at a symmetrical position; and a second step, wherein another substituent is introduced to the other carbon at a symmetrical position.

[0042] Another aspect of the present invention is a method for synthesizing a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative having the above-described structure, wherein two substituents are respectively bonded to carbon at symmetrical positions and the substituents are different from each other, and N-methyl-2-pyrrolidone is used as a solvent.

[0043] Another aspect of the present invention is an organic semiconductor device comprising any of the aforementioned organic compounds.

[0044] Another aspect of the present invention is a light-emitting device comprising any of the organic compounds described above.

[0045] Another aspect of the present invention is a light-receiving device comprising any of the aforementioned organic compounds.

[0046] Another aspect of the present invention is an organic electronic device that uses any of the above-mentioned organic compounds in the coating layer.

[0047] Another aspect of the present invention is an electronic device that includes the aforementioned organic electronic devices.

[0048] One aspect of the present invention provides a synthetic method that readily introduces different substituents into symmetrical positions of 1,10-phenanthroline derivatives or 2,2'-bipyridine derivatives.

[0049] Alternatively, another aspect of the present invention can provide an organic compound in which different substituents are introduced into two carbons at an axially symmetrical position in a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative. Another aspect of the present invention can provide an organic compound in which an aliphatic cyclic amino group is introduced into one carbon at an axially symmetrical position in a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative, and a substituent different from the aliphatic cyclic amino group (hereinafter also referred to as substituent A) is introduced into the other carbon.

[0050] Alternatively, another aspect of the present invention can provide a novel phenanthroline derivative or a bipyridine derivative. Furthermore, another aspect of the present invention can provide a method for synthesizing a novel phenanthroline derivative or a bipyridine derivative.

[0051] In addition, according to one aspect of the present invention, a novel light-emitting device, a novel display device, a novel display module, and a novel electronic device can be provided.

[0052] Note that the description of these effects does not preclude the existence of other effects. One aspect of the invention does not necessarily require all of the aforementioned effects. Effects other than those described above can be extracted from the specification, drawings, and claims. Attached Figure Description

[0053] Figures 1A to 1C This is a diagram representing a light-emitting device; Figure 2A and Figure 2B These are the top view and cross-sectional view of the light-emitting device; Figure 3A and Figure 3B This is a perspective view showing an example of the structure of a display module; Figure 4A and Figure 4B This is a cross-sectional view showing an example of the structure of a display device; Figure 5 This is a perspective view showing an example of the structure of a display device; Figure 6 This is a cross-sectional view showing an example of the structure of a display device; Figure 7This is a cross-sectional view showing an example of the structure of a display device; Figure 8 This is a cross-sectional view showing an example of the structure of a display device; Figures 9A to 9D This is a diagram illustrating an example of an electronic device; Figures 10A to 10F This is a diagram illustrating an example of an electronic device; Figures 11A to 11G This is a diagram illustrating an example of an electronic device; Figures 12A to 12C It shows 4Cl7HidPhen 1 The 1H NMR spectrum; Figures 13A to 13C This shows Hid2Phen 1 The 1H NMR spectrum; Figures 14A to 14C It shows 4Cl7PrdPhen 1 The 1H NMR spectrum; Figures 15A to 15C It shows 4Br7HidPhen 1 The 1H NMR spectrum; Figures 16A to 16C It shows 4Br7PrdPhen 1 The 1H NMR spectrum; Figures 17A to 17C It shows 2Cl9HidPhen 1 The 1H NMR spectrum; Figures 18A to 18C This shows 4Cl4'HidBpy. 1 The 1H NMR spectrum; Figures 19A to 19C This shows Hid-DPPrdPhen 1 The 1H NMR spectrum; Figures 20A to 20C This shows Hid-αNPrdPhen 1 The 1H NMR spectrum; Figures 21A to 21C This shows Hid-αNPPhen 1 The 1H NMR spectrum; Figures 22A to 22C This shows Hid-ceHBazPhen 1 The 1H NMR spectrum; Figure 23 It is a diagram showing the brightness-current density characteristics of light-emitting device 1-1, light-emitting device 1-2, and comparison of light-emitting device 1; Figure 24This is a diagram showing the current efficiency-brightness characteristics of light-emitting device 1-1, light-emitting device 1-2, and a comparison of light-emitting device 1; Figure 25 This is a diagram showing the brightness-voltage characteristics of light-emitting device 1-1, light-emitting device 1-2, and a comparison of light-emitting device 1; Figure 26 It is a graph showing the current density-voltage characteristics of light-emitting device 1-1, light-emitting device 1-2, and comparison light-emitting device 1; Figure 27 This is a diagram showing the electroluminescence spectra of light-emitting device 1-1, light-emitting device 1-2, and comparative light-emitting device 1; Figure 28 This is a diagram showing the brightness-current density characteristics of light-emitting device 2-1, light-emitting device 2-2, and a comparison of light-emitting device 2; Figure 29 This is a diagram showing the current efficiency-brightness characteristics of light-emitting device 2-1, light-emitting device 2-2, and comparison of light-emitting device 2; Figure 30 This is a diagram showing the brightness-voltage characteristics of light-emitting device 2-1, light-emitting device 2-2, and a comparison of light-emitting device 2; Figure 31 This is a graph showing the current density-voltage characteristics of light-emitting device 2-1, light-emitting device 2-2, and comparison light-emitting device 2; Figure 32 This is a diagram showing the electroluminescence spectra of light-emitting device 2-1, light-emitting device 2-2, and comparative light-emitting device 2; Figures 33A to 33C This shows Hid-AcuPhen 1 The 1H NMR spectrum. Detailed Implementation

[0054] The embodiments will be described in detail with reference to the accompanying drawings. Note that the present invention is not limited to the following description, and those skilled in the art will readily understand that its methods and details can be varied in many ways without departing from the spirit and scope of the invention. Therefore, the present invention should not be construed as being limited to the contents described in the embodiments shown below.

[0055] Furthermore, in this specification, ordinal numbers such as "first" and "second" are added to avoid confusion among the constituent elements and do not indicate a specific order or sequence, such as the order of processes or stacking. Additionally, to avoid confusion among the constituent elements, even phrases not explicitly stated in this specification may sometimes have ordinal numbers included in the claims. Regarding phrases explicitly stated in this specification, different ordinal numbers may sometimes be included in the claims. Regarding phrases explicitly stated in this specification, the ordinal numbers may sometimes be omitted in the claims.

[0056] Note that in this specification, photoluminescence (PL) spectroscopy refers to the spectrum obtained by scanning the emission wavelength and measuring the emission intensity in fluorescence spectrophotometry with a fixed excitation wavelength. It is sometimes also called emission spectrum. Furthermore, emission spectra sometimes include fluorescent and phosphorescent components. In this specification, emission spectra consisting of fluorescent components are sometimes referred to as fluorescence spectra, and emission spectra consisting of phosphorescent components are particularly referred to as phosphorescence spectra.

[0057] Implementation Method 1 1,10-phenanthroline derivatives and 2,2'-bipyridine derivatives possess excellent electron transport properties and are therefore actively used as materials for organic semiconductor devices such as organic EL devices (which are synonymous with light-emitting devices in this specification). For example, red phenanthroline (BPhen) and 2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBPhen), as 1,10-phenanthroline derivatives, have high electron transport properties and have been widely used since ancient times.

[0058] Furthermore, 1,10-phenanthroline derivatives such as 4,7-di-1-pyrrolidinyl-1,10-phenanthroline (abbreviated as Pyrrd-Phen), which have electron-donating groups at the 4 and 7 positions, can increase the electron density of nitrogen at the 1 and 10 positions of 1,10-phenanthroline. Therefore, the composite material co-deposited with a metal or metal compound can be appropriately used as the electron injection layer in a light-emitting device and as the n-type layer in the intermediate layer of a tandem light-emitting device. It is particularly preferred when this composite material is used in light-emitting devices where the EL layer is processed using photolithography, as the rise in driving voltage is suppressed.

[0059] Here, the conventionally used 1,10-phenanthroline derivatives, especially the aforementioned 1,10-phenanthroline derivatives with substituents at positions 4 and 7, are organic compounds with a symmetrical 1,10-phenanthroline skeleton as the main skeleton, and the substituents at positions 4 and 7 are identical, exhibiting a so-called C2 symmetry. When substituents are introduced into the two symmetrical carbons of a 1,10-phenanthroline derivative (e.g., carbons at positions 2 and 9, 3 and 8, 4 and 7, 5 and 6), for example, substituents can be introduced and synthesized by nucleophilic substitution reactions or Buchwald-Hartwig reactions on 1,10-phenanthroline derivatives substituted at these carbon positions with halogens, trifluoromethanesulfonate groups, etc. Furthermore, 1,10-phenanthroline derivatives substituted at these positions with halogens, trifluoromethanesulfonate groups, etc., can be readily obtained.

[0060] However, from the viewpoint of chemical reactivity, it is difficult to introduce different substituents into the 2 and 9, 3 and 8, 4 and 7, and 5 and 6 positions using this method, since the 2 and 9, 3 and 8, 4 and 7, and 5 and 6 positions are equal. Similarly, it is also difficult to introduce different substituents into the symmetrical positions of 2,2'-bipyridine.

[0061] As mentioned above, while it is possible to synthesize asymmetric substituents, such as in 1,10-phenanthroline, using methods like the Skipp reaction, this requires highly hazardous reagents like concentrated sulfuric acid and has low reaction selectivity, making it impractical. Even if synthesis is possible, multiple analogs are generated simultaneously, making purification uncertain, thus this method cannot be considered suitable for supplying asymmetric 1,10-phenanthroline derivatives.

[0062] Similarly, two pyridine derivatives of 2,2'-bipyridine, with different substituents at the 4-position and halogen, pinacol, or boron substituents at the 2-position, can also be synthesized via cross-coupling. However, pyridine compounds with boron at the 2-position are generally known to have low stability, are difficult to adjust and store, and the coupling reaction induces self-coupling as a side reaction, theoretically yielding a mixture of at least three reaction products. Therefore, the purification process is significantly burdened when separating and purifying the desired compound from three compounds with similar properties. Furthermore, cross-coupling reactions generally increase manufacturing costs due to the use of expensive transition metal catalysts. Transition metal catalysts include: for example, cheaper transition metal catalysts such as nickel could be considered, but nickel is carcinogenic, requiring adjustments to the safety and hygiene environment of research facilities and production sites, making its active use difficult, and preparing such an environment is costly. In other words, it can be said that, using existing technology prior to the invention of the technology developed by our company, obtaining the aforementioned asymmetric 1,10-phenanthroline or 2,2'-bipyridine derivatives would require at least a significant amount of time and cost, and it is uncertain whether the compound can be synthesized and supplied using existing technology.

[0063] However, here, the inventors have discovered that by using an inorganic base and a solvent to react a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative having a symmetrical structure and a halogen or trifluoromethanesulfonyl group bonded to two carbons at symmetrical positions with an aliphatic cyclic amine, an asymmetrical 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative can be obtained, wherein the aliphatic cyclic amine is bonded to one carbon at a symmetrical position.

[0064] This method can be described as a technique for stably synthesizing and providing asymmetric 1,10-phenanthroline or 2,2'-bipyridine derivatives by using relatively inexpensive commercially available symmetrical 1,10-phenanthroline or 2,2'-bipyridine derivatives.

[0065] By substituting the remaining halogen or trifluoromethanesulfonyl group and any substituent in the asymmetric 1,10-phenanthroline derivative or 2,2'-bipyridine derivative obtained from the reaction, 1,10-phenanthroline derivatives or 2,2'-bipyridine derivatives with substituents in different symmetrical positions can be obtained.

[0066] Furthermore, as the inorganic base used in this reaction, salts containing alkali metals or alkaline earth metals, or hydroxides or hydrides of metal elements, can be used. Potassium carbonate or potassium acetate are preferred as they offer high yields. Additionally, highly polar solvents such as N-methyl-2-pyrrolidone and ethanol can be used as solvents, with N-methyl-2-pyrrolidone being particularly preferred due to its high yield.

[0067] Furthermore, in this reaction, even if more than two equivalents of an aliphatic cyclic amine are added to the remaining halogen or trifluoromethanesulfonyl group in the 1,10-phenanthroline derivative or the 2,2'-bipyridine derivative, 1,10-phenanthroline derivatives or 2,2'-bipyridine derivatives bonded to any one of the carbon atoms at symmetrical positions and bonded to an aliphatic cyclic amine can be obtained in high yield. Therefore, in mass production processes, greater flexibility and a stable supply system can be established under conditions such as the amount of raw materials, reaction temperature, or reaction time.

[0068] In reactions aimed at obtaining the aforementioned asymmetric 1,10-phenanthroline derivatives or 2,2'-bipyridine derivatives, one of the key factors for selectivity is the combination of solvent and base. As will be explained in detail later, as disclosed in Non-Patent Document 1, when an amine dissolved in an organic solvent is used as the base, symmetric di-substituted 1,10-phenanthroline derivatives can be selectively obtained. Therefore, when the reaction system is kept strongly basic, it is difficult to obtain asymmetric mono-substituted 1,10-phenanthroline.

[0069] On the other hand, in one aspect of the synthesis method of the present invention, by using an inorganic base such as potassium carbonate, which has reduced solubility in organic solvents, the basicity in the reaction system can be maintained within an appropriate pH range to obtain the asymmetric 1,10-phenanthroline, a point that contributes to the selectivity of the reaction. Similarly, acetates of weakly basic salts also contribute to selectivity. Thus, in one aspect of the synthesis method of the present invention, polybasic acid salts such as phosphates, whose solubility in solvents and pH are easily controlled, can also be used as the base, thereby selectively obtaining the asymmetric 1,10-phenanthroline derivative or the 2,2'-bipyridine derivative by using such a base.

[0070] By using the above synthetic method, an organic compound represented by the following general formula (G1) can be obtained.

[0071] [Chemical Formula 11]

[0072] In the above general formula (G1), X 2 To X 5 One of them is a halogen or trifluoromethanesulfonyl group, and the others are hydrogen. Additionally, R... 2 To R 5 Each of them represents an aliphatic cyclic amino group represented by the following general formula (g1), and the others are hydrogen.

[0073] [Chemical Formula 12]

[0074] In the above general formula (g1), R 11 To R18 Each of these groups independently represents hydrogen (including deuterium) or any one of the following: an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, a secondary amino group with 2 to 10 carbon atoms (substituted or unsubstituted), a monovalent aromatic group with 6 to 30 carbon atoms (substituted or unsubstituted), a heteroaryl group with 1 to 30 carbon atoms, a cyano group, a halogen, a hydroxyl group, an amide group, or a carbonyl group. p and q independently represent 0 to 3. Note that R... 11 To R 18 Any two of them can also bond with each other to form a ring.

[0075] Note that in the organic compounds represented by the above general formula (G1), the positions of the carbons substituted by the halogen or trifluoromethanesulfonyl group are symmetrical with the positions of the carbons substituted by the group represented by the above general formula (G1). That is, in the above general formula (G1), when X 2 When it is a halogen or trifluoromethanesulfonyl group, R 2 This represents an aliphatic cyclic amino group represented by the above general formula (g1). Similarly, when X 3 When it is a halogen or trifluoromethanesulfonyl group, R 3 This represents an aliphatic cyclic amino group represented by the above general formula (g1), when X 4 When it is a halogen or trifluoromethanesulfonyl group, R 4 This represents an aliphatic cyclic amino group represented by the above general formula (g1), when X 5 When it is a halogen or trifluoromethanesulfonyl group, R 5 This represents an aliphatic cyclic amino group represented by the above general formula (g1).

[0076] That is, one aspect of the present invention is an organic compound represented by any of the following general formulas (G1-1) to (G1-4).

[0077] [Chemical Formula 13]

[0078] In the above general formulas (G1-1) to (G1-4), X is a halogen or trifluoromethanesulfonyl group, and R represents an aliphatic cyclic amino group represented by the above general formula (g1).

[0079] Similarly, by using the above-described synthetic method, an organic compound represented by the following general formula (G2) can be obtained.

[0080] [Chemical Formula 14]

[0081] In the above general formula (G2), X 6 To X 9One of them is a halogen or trifluoromethanesulfonyl group, and the others are hydrogen. Additionally, R... 6 To R 9 Each of them represents an aliphatic cyclic amino group represented by the above general formula (g1), and the others are hydrogen.

[0082] In organic compounds represented by the above general formula (G2), the positions of the carbons substituted by the halogen or trifluoromethanesulfonyl group are symmetrical with those substituted by the group represented by the above general formula (g1). That is, in the above general formula (G2), when X 6 When it is a halogen or trifluoromethanesulfonyl group, R 6 This represents an aliphatic cyclic amino group represented by the above general formula (g1). Similarly, when X 7 When it is a halogen or trifluoromethanesulfonyl group, R 7 This represents an aliphatic cyclic amino group represented by the above general formula (g1), when X 8 When it is a halogen or trifluoromethanesulfonyl group, R 8 This represents an aliphatic cyclic amino group represented by the above general formula (g1), when X 9 When it is a halogen or trifluoromethanesulfonyl group, R 9 This represents an aliphatic cyclic amino group represented by the above general formula (g1).

[0083] That is, one aspect of the present invention is an organic compound represented by any of the following general formulas (G2-1) to (G2-4).

[0084] [Chemical Formula 15]

[0085] In the above general formulas (G2-1) to (G2-4), X is a halogen or trifluoromethanesulfonyl group, and R represents the aliphatic cyclic amino group represented by the above general formula (g1).

[0086] Among the organic compounds represented by the above general formulas (G1), (G2), (G1-1) to (G1-4), and (G2-1) to (G2-4), due to X 2 To X 9 If any one of the groups or X is a halogen or a trifluoromethanesulfonyl group, then a wide variety of substituents can be introduced onto one side of the halogen and trifluoromethanesulfonyl groups by using these nucleophilic substitution reactions. Organic compounds that can be synthesized using one method of the present invention include, for example, organic compounds represented by the following general formula (G3).

[0087] [Chemical Formula 16]

[0088] In the above general formula (G3), R is a base represented by the following general formula (g1), and A is a base represented by the following general formula (g2) or the following general formula (g3). Note that in general formula (G3), substituent A and substituent R are different substituents.

[0089] [Chemical Formula 17]

[0090] In the above general formula (g1), R 11 To R 18 Each of these groups independently represents hydrogen (including deuterium) or any one of the following: an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, a secondary amino group with 2 to 10 carbon atoms (substituted or unsubstituted), a monovalent aromatic group with 6 to 30 carbon atoms (substituted or unsubstituted), a heteroaryl group with 1 to 30 carbon atoms, a cyano group, a halogen, a hydroxyl group, an amide group, or a carbonyl group. p and q independently represent 0 to 3. Note that R... 11 To R 18 Any two of them can also bond with each other to form a ring.

[0091] [Chemical Formula 18]

[0092] In the above general formula (g2), R 21 To R 28 Each of the following groups independently represents hydrogen (including deuterium), an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, a secondary amino group with 2 to 10 carbon atoms (substituted or unsubstituted), a monovalent aromatic group with 6 to 30 carbon atoms (substituted or unsubstituted), a heteroaryl group with 1 to 30 carbon atoms, a cyano group, a halogen, a hydroxyl group, an amide group, and a carbonyl group. s and t independently represent 0 to 3. Note that R... 21 To R 28Any two of them can also bond to each other to form a ring. Additionally, the aliphatic cyclic amino group represented by the above general formula (g2) can also be fused with an aromatic ring having 6 to 10 carbon atoms. Furthermore, in the above general formula (g3), Z represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted monovalent aromatic group having 6 to 30 carbon atoms, a substituted or unsubstituted monovalent heteroaromatic group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted secondary amino group, cyano group, halogen, hydroxyl group, amide group, or carbonyl group having 2 to 10 carbon atoms, and m represents an integer from 1 to 3. Note that when m is 2 or more, multiple Zs can also be the same or different groups. Additionally, L represents a substituted or unsubstituted alkylene group with 1 to 3 carbon atoms, a substituted or unsubstituted cycloalkylene group with 3 to 10 carbon atoms, a substituted or unsubstituted divalent aromatic group with 6 to 25 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group with 1 to 25 carbon atoms, and n represents an integer from 0 to 3. Note that when n is 2 or higher, multiple Ls can be the same or different groups.

[0093] In the organic compounds represented by the above general formula (G3), when A is an organic compound represented by the above general formula (G2), electrons are supplied to the 1,10-phenanthroline ring through a resonance effect, and the electron density of the 1,10-phenanthroline ring portion is increased, which is therefore preferred. That is, one aspect of the present invention is an organic compound represented by the following general formula (G3-1).

[0094] [Chemical Formula 19]

[0095] In the above general formula (G3-1), R 11 To R 18 and R 21 To R 28 Each of the following groups independently represents hydrogen (including deuterium), an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, a secondary amino group with 2 to 10 carbon atoms (substituted or unsubstituted), a monovalent aromatic group with 6 to 30 carbon atoms (substituted or unsubstituted), a heteroaryl group with 1 to 30 carbon atoms, a cyano group, a halogen, a hydroxyl group, an amide group, and a carbonyl group. p, q, s, and t independently represent 0 to 3. Note that R... 11 To R 18 Any two and R 21 To R 28Any two of them can also bond to each other to form a ring. Additionally, one of the aliphatic cyclic amino groups in the above general formula (G3-1) can also fused with an aromatic ring having 6 to 10 carbon atoms. Note that in general formula (G3-1), the substituents bonded to the 4 and 7 positions of the 1,10-phenanthroline skeleton are different substituents.

[0096] In the organic compounds represented by the above general formula (G3), when A is an organic compound represented by the above general formula (g3), since the substituents of 1,10-phenanthroline in (g1) and (g3) are different from each other, it is easy to adjust parameters such as electron donation, affinity or exclusivity to aqueous solvents, and heat resistance, and therefore it is preferred. That is to say, one aspect of the present invention is preferably an organic compound represented by the following general formula (G3-2).

[0097] [Chemical Formula 20]

[0098] In the above general formula (G3-2), R 11 To R 18 Each of the following groups independently represents hydrogen (including deuterium), an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, a secondary amino group with 2 to 10 carbon atoms (substituted or unsubstituted), a monovalent aromatic group with 6 to 30 carbon atoms (substituted or unsubstituted), a heteroaryl group with 1 to 30 carbon atoms, a cyano group, a halogen, a hydroxyl group, an amide group, and a carbonyl group, with p and q independently representing 0 to 3. Note that R... 11 To R 18 Any two of them can also bond to each other to form a ring. Additionally, Z represents an alkyl group with 1 to 10 substituted or unsubstituted carbon atoms, a cycloalkyl group with 3 to 10 substituted or unsubstituted carbon atoms, a monovalent aromatic group with 6 to 30 substituted or unsubstituted carbon atoms, a monovalent heterocyclic group with 1 to 30 substituted or unsubstituted carbon atoms, an alkoxy group with 1 to 10 substituted or unsubstituted carbon atoms, or a secondary amino group with 2 to 10 substituted or unsubstituted carbon atoms, and m represents an integer from 1 to 3. Note that when m is 2 or more, multiple Zs can also be the same or different groups. Additionally, L represents an alkylene group with 1 to 10 substituted or unsubstituted carbon atoms, a cycloalkylene group with 3 to 10 substituted or unsubstituted carbon atoms, a divalent aromatic group with 6 to 25 substituted or unsubstituted carbon atoms, or a divalent heterocyclic group with 1 to 25 substituted or unsubstituted carbon atoms, and n represents an integer from 0 to 3. Note that when n is 2 or more, multiple Ls can be the same or different bases.

[0099] Among the bases represented by the above general formula (g1) or general formula (g2), bases represented by the following structural formulas (Am-1) to (Am-49) are preferred, for example.

[0100] [Chemical Formula 21]

[0101] [Chemical Formula 22]

[0102] Examples of alkyl groups having 1 to 10 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, hexyl, isohexyl, heptyl, octyl, 3-methylpentyl, 2-methylpentyl, 2-ethylbutyl, 1,2-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylhexyl, 1-ethylpropyl, nonyl, 3,7-dimethyl-1-octyl, 3,7-dimethyl-2-octyl, and decyl. Tert-butyl or cyclohexyl groups are particularly preferred as they can reduce the refractive index. Note that when the alkyl group having 1 to 10 carbon atoms has a substituent, examples of such substituents include cycloalkyl groups having 3 to 6 carbon atoms, aryl groups having 6 to 13 carbon atoms, halogens, or cyano groups.

[0103] Examples of cycloalkyl groups having 3 to 10 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, adamantyl, bicyclo[2.2.1]heptyl, tricyclo[5.2.1.0(2,6)]decyl, noradamantyl, 1-methylcyclohexyl, bicyclo[2,2,2]octyl, norbornyl, etc. Note that when a cycloalkyl group having 3 to 10 carbon atoms has a substituent, examples of such substituents include alkyl groups having 1 to 4 carbon atoms, cycloalkyl groups having 3 to 6 carbon atoms, or aryl, halogen, cyano, etc., having 6 to 13 carbon atoms.

[0104] Examples of alkoxy groups with 1 to 10 carbon atoms include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, n-pentoxy, isopentoxy, sec-pentoxy, tert-pentoxy, neopentoxy, n-hexoxy, isohexoxy, sec-hexoxy, tert-hexoxy, neohexoxy, and cyclohexoxy.

[0105] Examples of monovalent aromatic groups having 6 to 30 carbon atoms include phenyl, o-tolyl, m-tolyl, p-tolyl, mesitylelel, biphenyl-2-yl (o-biphenyl), biphenyl-3-yl (m-biphenyl), biphenyl-4-yl (p-biphenyl), 1-naphthyl, 2-naphthyl, phenylnaphthyl, naphthylphenyl, terphenyl, fluorenyl, 9,9-dimethylfluorenyl, tetraphenyl, spirodifluorenyl, phenanthryl, anthracenel, binatylphenyl, fluoranyl, and triphenylene. Note that when the aryl group having 6 to 30 carbon atoms has a substituent, examples of such substituents include alkyl groups having 1 to 4 carbon atoms, cycloalkyl groups having 3 to 6 carbon atoms, aryl groups having 6 to 13 carbon atoms, halogens, or cyano groups.

[0106] Specific examples of heteroaryl groups with 1 to 30 carbon atoms include 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, pyrimidin-4-yl, pyrazin-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, carbazolyl, dibenzofuranyl, dibenzothiopheneyl, benzonaphthofuranyl, benzonaphthothiopheneyl, dinaphthofuranyl, dinaphthothiopheneyl, indolocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, indocarbazolyl, dibenzocarbazolyl, indolo, pyrrole-1,2,3-triazolyl, 1,2,4-triazolyl, etc. Note that when a heteroaryl group having 1 to 30 carbon atoms has a substituent, examples of such substituents include alkyl groups having 1 to 4 carbon atoms, cycloalkyl groups having 3 to 6 carbon atoms, aromatic groups having 6 to 13 carbon atoms, halogens, or cyano groups.

[0107] Examples of alkylene groups having 1 to 3 carbon atoms include methyl, vinyl, and propenyl groups. Additionally, examples of cycloalkylene groups having 3 to 10 carbon atoms include divalent groups derived from the cycloalkyl groups having 3 to 10 carbon atoms mentioned above by removing one hydrogen atom.

[0108] Examples of divalent heterocyclic groups with 1 to 25 carbon atoms include pyrimidine-diyl, pyrazin-diyl, pyridazin-diyl, triazin-diyl, bipyridine-diyl, phenanthroline-diyl, quinoxaline-diyl, dibenzoquinoxaline-diyl, quinazoline-diyl, benzoquinazoline-diyl, dibenzoquinazoline-diyl, imidazole-diyl, triazole-diyl, oxadiazole-diyl, benzimidazole-diyl, furandiazin-diyl, benzofuran-pyrimidine-diyl, and thiamethoxam. Fen-diyl, furan-diyl, benzothiophene-diyl, benzofuran-diyl, dibenzothiophene-diyl, dibenzofuran-diyl, benzonaphthothiophene-diyl, benzonaphthofuran-diyl, dinaphthothiophene-diyl, dinaphthofuran-diyl, piperazine-diyl, hexahydropyrimidine-diyl, hexahydrotriazine-diyl, decahydroquinoxaline-diyl, decahydronaphthidine-diyl, imidazoline-diyl, octahydropyrrolopyridine-diyl, octahydropyrrolopyrrolo-diyl. Note that when the divalent heterocyclic group having 1 to 25 carbon atoms has a substituent, examples of such substituents include alkyl groups having 1 to 4 carbon atoms, cycloalkyl groups having 3 to 6 carbon atoms, or aryl groups having 6 to 13 carbon atoms.

[0109] Examples of divalent aromatic groups having 6 to 25 carbon atoms include phenylene, biphenyl-diyl, naphthyl-diyl, fluorene-diyl, acenaphthene-diyl, anthracene-diyl, phenanthrene-diyl, terphenyl-diyl, triphenylene-diyl, tetraphenyl-diyl, benzanthracene-diyl, pyrene-diyl, and spirobis[9H-fluorene]-diyl. Note that when the aryl group having 6 to 30 carbon atoms has a substituent, examples of such substituents include alkyl groups having 1 to 4 carbon atoms, cycloalkyl groups having 3 to 6 carbon atoms, or aryl groups having 6 to 13 carbon atoms.

[0110] When an organic compound represented by the general formula (G3) has one or two alkyl groups, it is less likely to impede electron transport, and is therefore preferred. By having alkyl groups, the refractive index of the film formed by the organic compound can be reduced; when the number of alkyl groups is large, the refractive index of the vapor-deposited film becomes lower, and the luminous efficiency of the light-emitting device is improved. On the other hand, it is also known that the alkyl group tends to reduce electron transport. In one aspect of the present invention, even if the organic compound has few hydrocarbon groups, it can form a film with a low refractive index, thereby simultaneously achieving low electron transport and a low film refractive index.

[0111] Furthermore, when the organic compound represented by general formula (G3) is an organic compound having an alkyl group, at least one alkyl group is preferably bonded to the phenyl group. That is, the organic compound represented by general formula (G3) preferably contains a phenyl group having an alkyl group. Additionally, when the phenyl group has two alkyl groups, in order to facilitate the availability of synthetic raw materials, the two alkyl groups are preferably substituted at the 3- and 5-positions of the terminal phenyl group. As alkyl-containing phenyl groups, 4-cyclohexylphenyl, 3',5'-di-tert-butylphenyl, and 3',5'-dicyclohexylphenyl are particularly preferred.

[0112] The secondary amino group having 2 to 10 carbon atoms is preferably a cyclic secondary amine, such as pyrrolidin-1-yl, isoindol-2-yl, dihydroisoindol-2-yl, tetrahydroisoindol-2-yl, hexahydroisoindol-2-yl, hexahydroisoindololin-2-yl, piperidin-1-yl, aziridin-1-yl, aziridine-1-yl, octahydrocyclopentane[c]pyrrole-2-yl, octahydro-4,7-bridged methylene(methano)-1H-isoindol-2-yl, 2-nitrobicyclo[3.1.0] Hexane-2-yl, 3-azabicyclo[3.1.0]hexane-2-yl, 3-azabicyclo[3.2.0]heptane-2-yl, 5-azaspiro[3.4]octane-5-yl, 8-azabicyclo[3.2.1]octane-8-yl, 7-azabicyclo[2.2.1]heptane-7-yl, 5-azaspiro[2.4]heptane-5-yl, 5-azabicyclo[2.1.1]hexane-5-yl, etc., dimethylamino, diethylamino, diisopropylamino, diphenylamino, dicyclohexylamino, etc. When the cyclic secondary amino group having 2 to 10 carbon atoms has a substituent, examples of such substituents include alkyl groups having 1 to 4 carbon atoms, cycloalkyl groups having 3 to 6 carbon atoms, or aryl groups having 6 to 13 carbon atoms.

[0113] Examples of organic compounds represented by the above general formulas (G1) and (G2) include organic compounds represented by the following structural formulas (200) to (275).

[0114] [Chemical Formula 23]

[0115] [Chemical Formula 24]

[0116] [Chemical Formula 25]

[0117] [Chemical Formula 26]

[0118] In addition, as an organic compound represented by the above general formula (G3) that can be synthesized using an organic compound represented by the above general formula (G1), examples include organic compounds represented by the following structural formulas (100) to (135).

[0119] [Chemical Formula 27]

[0120] [Chemical Formula 28]

[0121] [Chemical Formula 29]

[0122] The following details a method for synthesizing an organic compound of one aspect of the present invention, represented by the above general formulas (G1) to (G3).

[0123] First, taking the synthesis of an organic compound represented by the following general formula (G1-3-1) as an example, a method for synthesizing an organic compound represented by the above general formulas (G1) and (G2) according to one aspect of the present invention will be described. Note that the following general formula (G1-3-1) represents the case where R in the above general formula (G1-3) is substituted by a group represented by (g1). Note that X and R in general formula (G1-3-1) 11 To R 18 p and q are the same as (G1-3), so repeated explanations are omitted.

[0124] [Chemical Formula 30]

[0125] Organic compounds represented by the general formula (G1-3-1) can be synthesized using a simple synthetic scheme as described in the following synthetic scheme (A-1).

[0126] [Chemical Formula 31]

[0127] In the above compound (a1), X represents halogen or trifluoromethanesulfonyl group.

[0128] R in the above compound (a2) 11 To R 18 p and q are the same as in general formula (g1).

[0129] In the synthetic scheme (A-1), a phenanthroline intermediate having an aliphatic cyclic amino group represented by the general formula (G1-3) can be obtained by nucleophilic substitution reaction of a phenanthroline derivative (a1) with an aliphatic cyclic amine derivative (a2) using a suitable solvent and an inorganic base.

[0130] Examples of inorganic bases usable in the nucleophilic substitution reaction represented by the above synthetic scheme (A-1) include carbonates such as potassium carbonate, cesium carbonate, sodium carbonate, and potassium bicarbonate; acetates such as potassium acetate and sodium acetate; and phosphates such as tripotassium phosphate and trisodium phosphate. Note that potassium carbonate and potassium acetate, especially potassium carbonate, have high yields and are therefore preferred.

[0131] Examples of solvents that can be used in the nucleophilic substitution reaction represented by the above synthetic scheme (A-1) include N-methyl-2-pyrrolidone, N,N-dimethylformamide, tetrahydrofuran, dioxane, ethanol, ethyl acetate, toluene, etc. Note that the solvents that can be used are not limited to these.

[0132] The above describes the method for synthesizing organic compounds represented by general formula (G1-3-1), but general formulas (G1-1), (G1-2), (G1-4) and general formulas (G2-1) to (G2-4) can also be synthesized by replacing the starting materials corresponding to phenanthroline derivatives (a1).

[0133] Next, taking an organic compound represented by general formula (3-1) as an example, the method for synthesizing an organic compound represented by general formula (G3) will be explained.

[0134] In the organic compound represented by general formula (G3-1), the substituent of A in the organic compound represented by the above general formula (G3) is a group represented by the above general formula (g2), and can be synthesized by a simple synthetic scheme such as the above synthetic scheme (A-1) and the following synthetic scheme (A-2).

[0135] [Chemical Formula 32]

[0136] In the above compound (a3), R 21 To R 28 , s, and t are the same as in general formula (g2). Note that different compounds are used than those used in (a2).

[0137] In synthetic scheme (A-2), an organic compound represented by general formula (G3-1) is obtained by nucleophilic substitution of a phenanthroline intermediate having an aliphatic cyclic amino group represented by general formula (G1-3) with an aliphatic cyclic amine derivative (a3) ​​using a suitable solvent and base.

[0138] Examples of bases that can be used in the nucleophilic substitution reaction represented by the above synthetic scheme (A-2) include organic bases such as diazabicycloundecene (DBU), triethylamine, and potassium tert-butoxide, as well as inorganic bases such as potassium carbonate, cesium carbonate, sodium carbonate, sodium bicarbonate, potassium acetate, sodium acetate, tripotassium phosphate, and trisodium phosphate.

[0139] Examples of solvents that can be used in the nucleophilic substitution reaction represented by the above synthetic scheme (A-2) include N-methyl-2-pyrrolidone, N,N-dimethylformamide, toluene, tetrahydrofuran, dioxane, and ethanol. Note that the solvents used are not limited to these. Additionally, when an organic base is used, it can be used as both a base and a solvent.

[0140] Furthermore, the reactions carried out in the above synthetic scheme (A-2) are not limited to nucleophilic substitution reactions, but can utilize Buchwald-Hartwig reactions, coupling reactions using copper or copper compounds, etc.

[0141] In the organic compounds represented by the above general formula (G3), the organic compounds represented by the general formula (G3-2) with the substituent of A represented by the above general formula (g3) can be synthesized by simple synthetic schemes such as the above synthetic scheme (A-1) and the following synthetic scheme (A-3).

[0142] [Chemical Formula 33]

[0143] In the above compound (a4), Q represents a boron hydroxyl group (-B(OH)2), and Z, L, n, and m are the same as in the general formula (g3). Additionally, in compound (a4), when Q is a boron hydroxyl group, borate esters or cyclic triol borates can also be used. However, Q is not limited to a boron hydroxyl group. Furthermore, it can also be a nucleophile such as magnesium or zinc, which are generally widely used in coupling reactions. From the viewpoint of environmental impact and ease of obtaining raw materials, a boron hydroxyl group is preferred.

[0144] Examples of palladium catalysts usable in the coupling reaction represented by the above synthetic scheme (A-3) include palladium(II) acetate, tetra(triphenylphosphine)palladium(O), and bis(triphenylphosphine)palladium(II) dichloride. Examples of ligands for palladium catalysts include bis(1-adamantane)-n-butylphosphine, (±)-2,2'-bis(diphenylphosphine)-1,1'-binaphthyl, tris(o-tolyl)phosphine, triphenylphosphine, and tricyclohexylphosphine.

[0145] Examples of bases that can be used in the coupling reaction represented by the above synthetic scheme (A-3) include organic bases such as potassium tert-butoxide, and inorganic bases such as cesium carbonate, potassium carbonate, sodium carbonate, and tripotassium phosphate.

[0146] Examples of solvents that can be used in the coupling reaction represented by the above synthetic scheme include 1,2-dimethoxyethane, toluene, xylene, mesitylene, benzene, tetrahydrofuran, and dioxane. Note that the solvents that can be used are not limited to these.

[0147] Furthermore, the reactions carried out in the above synthetic scheme (A-3) are not limited to the Suzuki-Miyaura reaction, but can also be carried out using the Yuda-Kosugi-Stille coupling reaction using organotin compounds, coupling reactions using Grignard reagents, the Negishi reaction, coupling reactions using copper or copper compounds, nucleophilic substitution reactions, etc.

[0148] In addition, various of the above-mentioned compounds (a1), (a2), (a3) ​​and (a4) are available on the market, or can be synthesized.

[0149] The organic compound of one embodiment of the present invention can be synthesized as described above, but the present invention is not limited thereto and can also be synthesized by other synthetic methods.

[0150] This implementation method can be used in any combination with other implementation methods and examples.

[0151] This embodiment can be appropriately combined with other embodiments or examples. Furthermore, where multiple structural examples are shown in one embodiment in this specification, these structural examples can be appropriately combined.

[0152] Implementation Method 2 In this embodiment, a light-emitting device according to one aspect of the present invention is described in detail.

[0153] Figures 1A to 1C This is a schematic diagram of a light-emitting device according to one embodiment of the present invention. A first electrode 101 of the light-emitting device is disposed on an insulator 100, and an organic compound layer 103 is included between the first electrode 101 and the second electrode 102. The organic compound layer 103 contains at least one of the organic compounds represented by general formula (G3) in Embodiment 1. The light-emitting layer 113 in the light-emitting device contains a light-emitting center material, which emits light by applying a voltage between the first electrode 101 and the second electrode 102.

[0154] Preferably, such as Figure 1A As shown, in addition to the light-emitting layer 113, the organic compound layer 103 includes functional layers such as a hole injection layer 111, a hole transport layer 112, an electron transport layer 114, and an electron injection layer 115. Note that the organic compound layer 103 may also include functional layers other than the aforementioned functional layers such as a hole blocking layer, an electron blocking layer, an exciton blocking layer, and a charge generation layer. Conversely, any of the aforementioned layers may not be provided.

[0155] Because the organic compound represented by general formula (G3) in Embodiment 1 has high electron transport and electron injection properties, it is preferable to include it in the layer where electrons are used as charge carriers. Examples of layers where electrons are used as charge carriers include electron injection layers, electron transport layers, hole blocking layers, light-emitting layers, and intermediate layers. The organic compound represented by general formula (G3) is particularly preferred for electron injection layers and intermediate layers.

[0156] In this embodiment, the first electrode 101 is referred to as an electrode including an anode and the second electrode 102 is referred to as an electrode including a cathode, but the reverse is also possible. The first electrode 101 and the second electrode 102 are formed in a single-layer structure or a multilayer structure. When a multilayer structure is provided, the layer in contact with the organic compound layer 103 is used as the anode or cathode. When the electrode has a multilayer structure, there are no restrictions on the work function of the layers other than the layer in contact with the organic compound layer 103, and the material can be selected according to the required characteristics such as resistance, ease of processing, reflectivity, light transmittance, and stability.

[0157] The anode is preferably formed using a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically 4.0 eV or higher). Examples of such anodes include indium tin oxide (ITO), indium tin oxide (ITSO) containing silicon or silicon oxide, indium zinc oxide, and indium tin oxide (IWZO) containing tungsten oxide and zinc oxide. While these conductive metal oxide films are typically deposited by sputtering, they can also be formed using sol-gel methods. Examples of formation methods include sputtering an indium tin oxide film using a target containing 1 wt% to 20 wt% zinc oxide. Furthermore, indium tin oxide (IWZO) containing tungsten oxide and zinc oxide can be formed by sputtering a target containing 0.5 wt% to 5 wt% tungsten oxide and 0.1 wt% to 1 wt% zinc oxide. Furthermore, materials used for the anode include, for example, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), aluminum (Al), or nitrides of metallic materials (e.g., titanium nitride). The anode can also be a layer of the aforementioned materials stacked together. For example, a film sequentially stacked with Al, Ti, and ITSO on Ti is preferred due to its good reflectivity, resulting in high efficiency and achieving high resolution of several thousand ppi. Graphene can also be used as the anode material. Furthermore, by using a composite material that can constitute the hole injection layer 111 described later as the layer in contact with the anode (typically a hole injection layer), the work function can be disregarded when selecting the electrode material.

[0158] Hole injection layer 111 is in contact with the anode and facilitates hole injection into organic compound layer 103. Phthalocyanine compounds and phthalocyanine complexes such as phthalocyanine (H2Pc), copper phthalocyanine (CuPc), etc.; aromatic amine compounds such as 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (DNTPD), etc.; or polymeric compounds such as poly(3,4-ethylenedioxythiophene) / (polystyrene sulfonic acid) (PEDOT / PSS), etc., can be used to form hole injection layer 111.

[0159] Furthermore, the hole injection layer 111 can also be composed of a substance with electron-accepting properties. As such, organic compounds with electron-withdrawing groups (halogen groups, cyano groups, etc.) can be used, including 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinone dimethyl ether (abbreviated: F4-TCNQ), chloroquinone, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviated: HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinone dimethyl ether (abbreviated: F6-TCNNQ), 2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyrene-2-yl)malononitrile, etc. In particular, compounds such as HAT-CN, which have electron-withdrawing groups bonded to fused aromatic rings with multiple heteroatoms, are thermally stable and therefore preferred. Furthermore, [3] axylene derivatives containing electron-withdrawing groups (especially halogen groups such as fluorine groups, cyano groups, etc.) are particularly preferred due to their high electron acceptor properties. Examples include: α,α',α”-1,2,3-cyclopropanetrimethylenetri[4-cyano-2,3,5,6-tetrafluorophenylacetonitrile], α,α',α”-1,2,3-cyclopropanetrimethylenetri[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)phenylacetonitrile], and α,α',α”-1,2,3-cyclopropanetrimethylenetri[2,3,4,5,6-pentafluorophenylacetonitrile]. In addition to the aforementioned organic compounds, transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide can also be used as acceptor substances.

[0160] Furthermore, the hole injection layer 111 is preferably formed of a composite material comprising the aforementioned acceptor material and an organic compound with hole transport properties.

[0161] Various organic compounds with hole-transporting properties can be used as the organic compound for use in composite materials, such as aromatic amines, heteroaromatics, aromatic hydrocarbons, and polymers (oligomers, dendritic polymers, polymers, etc.). Preferably, the organic compound with a hole mobility of 1×10⁻⁶ is used. -6 cm 2 Organic compounds with a ratio of / Vs or higher. The organic compounds with hole-transporting properties used in composite materials are preferably compounds containing fused aromatic rings or π-electron-rich heteroaromatic rings. As fused aromatic rings, anthracene rings, naphthalene rings, etc., are preferred. Furthermore, as π-electron-rich heteroaromatic rings, fused aromatic rings containing at least one of a pyrrole skeleton, a furan skeleton, and a thiophene skeleton are preferred, specifically carbazole rings, dibenzothiophene rings, or rings that are also fused with aromatic or heteroaromatic rings.

[0162] Such hole-transporting organic compounds more preferably have at least one of a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton, and an anthracene skeleton. In particular, they can be aromatic amines having substituents comprising a dibenzofuran ring or a dibenzothiophene ring, aromatic monoamines comprising a naphthyl ring, or aromatic monoamines in which a 9-fluorenyl group is bonded to the nitrogen of the amine via an arylene group. Note that when these hole-transporting organic compounds are substances comprising N,N-bis(4-biphenyl)amino groups, long-lifetime light-emitting devices can be manufactured, and therefore they are preferred.

[0163] Specifically, examples of the aforementioned hole-transporting organic compounds include N-(4-biphenyl)-6,N-diphenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviated as: BnfABP), N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviated as: BBABnf), 4,4'-bis(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)-4”-phenyltriphenylamine (abbreviated as: BnfBB1BP), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviated as: BBABnf(6)), and 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-benzidine (abbreviation: ThBA1BP), 4-(2-naphthyl)-4',4”-diphenyltriphenylamine (abbreviation: BBAβNB), 4-[4-(2-naphthyl)phenyl]-4',4”-diphenyltriphenylamine (abbreviation: BBAβNBi), 4,4'-diphenyl-4” -([2,1'-binathyl]-6-yl)triphenylamine (abbreviation: BBAαNβNB), 4,4'-diphenyl-4”-([2,1'-binathyl]-7-yl)triphenylamine (abbreviation: BBAαNβNB-03), 4,4'-diphenyl-4”-(7-phenyl)naphthyl-2-yltriphenylamine (abbreviation: BBAPβNB-03), 4,4'-diphenyl-4”-([2,2'-binathyl]-6-yl)triphenylamine (abbreviation: BBA(βN2)B), 4,4'-diphenyl-4”-([2,2'-binathyl]-7-yl)triphenylamine (abbreviation: BBA(βN2)B-03), 4,4'-diphenyl-4”-([1,2'-binathyl) -4-yl)triphenylamine (abbreviation: BBAβNαNB), 4,4'-diphenyl-4”-([1,2'-binaphthyl]-5-yl)triphenylamine (abbreviation: BBAβNαNB-02), 4-(4-biphenyl)-4'-(2-naphthyl)-4”-phenyltriphenylamine (abbreviation: TPBiAβNB), 4-(3-biphenyl)-4'-[4-(2-naphthyl)phenyl]-4”-phenyltriphenylamine (abbreviation: mTPBiAβNBi), 4-(4-biphenyl)-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: YGTBilBP), 4'-[4-(3-phenyl-9H-carbazole-9-yl)phenyl]tri(biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02), 4-[4'-(carbazole-9-yl)biphenyl-4-yl]-4'-(2-naphthyl)-4”-phenyltriphenylamine (abbreviation: YGTBiβNB), N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9'-spirodi[9H-fluorene]-2-amine (abbreviation: PCBNB) SF), N,N-bis(biphenyl-4-yl)-9,9'-spirodi[9H-fluorene]-2-amine (abbreviated as: BBASF), N,N-bis(biphenyl-4-yl)-9,9'-spirodi[9H-fluorene]-4-amine (abbreviated as: BBASF(4)), N-(biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirodi[9H-fluorene]-4-amine (abbreviated as: oFBiSF), N-(biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)dibenzofuran-4-amine (abbreviated as: FrBiF), N-[4-(1-naphthyl)phenyl]-N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthylamine ( Abbreviations: mPDBfBNBN), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4'-[4-(9-phenylfluorene-9-yl)phenyl]triphenylamine (abbreviation: BPAFLBi), 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBA1BP), 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: mPDBfBNBN), 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4'-[4-(9-phenylfluorene-9-yl)phenyl]triphenylamine (abbreviation: BPAFLBi), 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: mBPAFLP ... The following are listed as abbreviations: PCBANB, 4,4'-bis(1-naphthyl)-4”-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBABB), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9'-spirodi[9H-fluorene]-2-amine (abbreviation: PCBASF), N-(biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: PCBiF), N,N-bis(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirodi-9H-fluorene-4-amine, N,N-bis(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirodi-9H-fluorene-3-amine, N,N-bis(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirodi-9H-fluorene-2-amine, N,N-bis(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirodi-9H-fluorene-1-amine, etc.

[0164] In addition, as a material with hole transport capabilities, other aromatic amine compounds such as N,N'-bis(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (DPA3B) can also be used.

[0165] By forming a hole injection layer 111, hole injection capability can be improved, thereby obtaining a light-emitting device with low driving voltage.

[0166] Furthermore, organic compounds with acceptor properties can be easily formed using vapor deposition in substances with acceptor properties, making them easy-to-use materials.

[0167] The hole transport layer 112 is formed by comprising an organic compound with hole transport properties. The organic compound with hole transport properties preferably has a concentration of 1 × 10⁻⁶. -6 cm 2 Hole mobility above / Vs.

[0168] Examples of materials exhibiting hole transport capabilities include: 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl (TPD), N,N'-bis(9,9'-spirobis[9H-fluorene]-2-yl)-N,N'-diphenyl-4,4'-diaminobiphenyl (BSPB), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BPAFLP), 4-phenyl-3'-(9-phenylfluorene-9-yl)triphenylamine (mBPAFLP), and 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (PCBA1BP). Compounds with aromatic amine skeletons, such as 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)triphenylamine (abbreviation: PCCNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]fluorene-2-amine (abbreviation: PCBAF), and N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9'-spirodi[9H-fluorene]-2-amine (abbreviation: PCBASF);1,3-Bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-bis(N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-didiphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 9,9'-bis(biphenyl-4-yl)-3,3'-bi-9H-carbazole (abbreviation: BisBPCz), 9,9'-bis(biphenyl-3-yl)-3,3'-bi-9H-carbazole (abbreviation: BisBPCz), 9-(biphenyl-3-yl)-9'-(biphenyl-4-yl)-9H,9 'H-3,3'-Bicarbazole (abbreviation: mBPCCBP), 9-(2-naphthyl)-9'-phenyl-3,3'-bi-9H-carbazole (abbreviation: βNCCP), 9-(3-biphenyl)-9'-(2-naphthyl)-3,3'-bi-9H-carbazole (abbreviation: βNCCmBP), 9-(4-biphenyl)-9'-(2-naphthyl)-3,3'-bi-9H-carbazole (abbreviation: βNCCBP), 9,9'-di-2-naphthyl-3,3'-9H,9'H-bicarbazole (abbreviation: BisβNCz), 9-(2-naphthyl)-9'-[1,1':4',1”-terphenyl] -3-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':3',1”-terphenyl]-3-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':3',1”-terphenyl]-5'-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':4',1”-terphenyl]-4-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':3',1”-terphenyl]-4-yl-3,3'-9H,9'H-bicarbazole Compounds with a carbazole skeleton, such as 9-(2-naphthyl)-9'-(triphenyl-2-yl)-3,3'-9H,9'H-bicarbazole, 9-phenyl-9'-(triphenyl-2-yl)-3,3'-9H,9'H-bicarbazole (abbreviated as PCCzTp), 9,9'-bis(triphenyl-2-yl)-3,3'-9H,9'H-bicarbazole, 9-(4-biphenyl)-9'-(triphenyl-2-yl)-3,3'-9H,9'H-bicarbazole, and 9-(triphenyl-2-yl)-9'-[1,1':3',1”-terphenyl]-4-yl-3,3'-9H,9'H-bicarbazole;Compounds with a thiophene skeleton, such as 4,4',4”-(benzyl-1,3,5-triyl)tris(dibenzothiophene) (abbreviated as DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]dibenzothiophene (abbreviated as DBTFLP-III), and 4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviated as DBTFLP-IV); and compounds with a furan skeleton, such as 4,4',4”-(benzyl-1,3,5-triyl)tris(dibenzofuran) (abbreviated as DBF3P-II) and 4-{3-[3-(9-phenyl-9H-fluorene-9-yl)phenyl]phenyl}dibenzofuran (abbreviated as mmDBFFLBi-II). Compounds with an aromatic amine backbone and compounds with a carbazole backbone are preferred due to their high reliability, excellent hole transport properties, and ability to reduce driving voltage. Note that materials with hole transport properties, such as those used in the hole injection layer 111, can also be appropriately used as materials constituting the hole transport layer 112.

[0169] The luminescent center can be a fluorescent luminescent substance, a phosphorescent luminescent substance, a substance exhibiting thermally activated delayed fluorescence (TADF), or other luminescent substances.

[0170] In the luminescent layer, materials that can be used as fluorescent luminescent substances include, for example, the following substances. Note that other fluorescent luminescent substances can also be used.

[0171] Examples include 5,6-bis[4-(10-phenyl-9-anthrayl)phenyl]-2,2'-bipyridine (abbreviated as PAP2BPy), 5,6-bis[4'-(10-phenyl-9-anthrayl)biphenyl-4-yl]-2,2'-bipyridine (abbreviated as PAPP2BPy), N,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluorene-9-yl)phenyl]pyrene-1,6-diamine (abbreviated as 1,6FLPAPrn), and N,N'-bis(3-methylphenyl)-N,N '-Bis[3-(9-phenyl-9H-fluorene-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), 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-anthrayl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazole-9-yl)-4'-(9,10-diphenyl-2- Anthrayl)triphenylamine (abbreviated as: 2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole-3-amine (abbreviated as: PCAPA), dinaphthalene, 2,5,8,11-tetra-tert-butyldinaphthalene (abbreviated as: TBP), 4-(10-phenyl-9-anthrayl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as: PCPAPA), N,N”-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene) Bis(N,N',N'-triphenyl-1,4-phenylenediamine) (abbreviated as DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-anthrayl)phenyl]-9H-carbazole-3-amine (abbreviated as 2PCAPPA), N-[4-(9,10-diphenyl-2-anthrayl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPAPPA), N,N,N',N',N",N",N"',N"'-octaphenyldibenzo[g,p] (chrysene)-2,7,10,15-tetramine (DBCl), coumarin 30, 9,10-diphenyl-2-[N-phenyl-N-(9-phenyl-carbazole-3-yl)amino]anthracene (2PCAPA), N-[9,10-bis(biphenyl-2-yl)-2-anthrayl]-N,9-diphenyl-9H-carbazole-3-amine (2PCABPhA), N-(9,10-diphenyl-2-anthrayl)-N,N',N'-triphenyl-1,4-phenylenediamine (2DPAPA), N-[9,10-bis(biphenyl-2-yl)-2-anthrayl]-N,N',N'-triphenyl-1,4-phenylenediamine (2DPABPhA) 9,10-Bis(biphenyl-2-yl)-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracene-9-amine (abbreviation: DPhAPhA), coumarin 545T, N,N'-diphenylquinacridone (abbreviation: DPQd), rubrene, 5,12-bis(biphenyl-4-yl)-6,11-diphenylbenzotetraphenyl (abbreviation: BPT), 2-(2-{2-[4-(dimethylamino)phenyl]vinyl}-6-methyl-4H-pyran-4-yl)malononitrile (abbreviation: DCM1), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinazine-9- [2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinazine-9-yl)vinyl]-4H-pyran-4-ylidene}malononitrile (abbreviation: DCM2), N,N,N',N'-tetra(4-methylphenyl)-4H-pyran-4-ylidene}malononitrile (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetra(4-methylphenyl)acenaphthene[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinazine-9-yl)vinyl]-4H-pyran-4-ylidene}malononitrile (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7-tetramethyl ... 2,3,6,7-Tetrahydro-1H,5H-benzo[ij]quinazine-9-yl)vinyl]-4H-pyran-4-ylidene}malonium (abbreviation: DCJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]vinyl}-4H-pyran-4-ylidene)malonium (abbreviation: BisDCM), 2-{2,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinazine-9-yl)vinyl]-4H-”pyran-4-ylidene}malonium (abbreviation: BisDCJTM), N,N'-diphenyl-N,N'-(1,6-pyrene-diyl)bis[(6-phenylbenzo[b]naphtho[1,[2-d]furan)-8-amine] (abbreviated as: 1,6BnfAPrn-03), N,N'-diphenyl-N,N'-bis(9-phenyl-9H-carbazole-2-yl)naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviated as: 3,10PCA2Nbf(IV)-02), 3,10-bis[N-(dibenzofuran-3-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviated as: 3,10FrA2Nbf(IV)-02), etc. In particular, fused aromatic diamine compounds, represented by pyrene diamine compounds such as 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03, have high hole trapping, high luminescence efficiency, and high reliability, and are therefore preferred. ,

[0172] In addition, 5,9-diphenyl-5,9-diaza-13b-boronazonaphtho[3,2,1-de]anthracene (abbreviated as DABNA1), 9-(diphenyl-3-yl)-N,N,5,11-tetraphenyl-5,9-dihydro-5,9-diaza-13b-boronazonaphtho[3,2,1-de]anthracene-3-amine (abbreviated as DABNA-2), and 2,12-bis(tert-butyl)-5,9-bis(4-tert-butylphenyl)-N,N-diphenyl-5H,9H-[1,4]benzozaboron[2,3,4-kl]phenazaboron-7 -amine (abbreviation: DPhA-tBu4DABNA), 2,12-di(tert-butyl)-N,N,5,9-tetra(4-tert-butylphenyl)-5H,9H-[1,4]benzozaboron[2,3,4-kl]benzozaboron-7-amine (abbreviation: tBuDPhA-tBu4DABNA), 2,12-di(tert-butyl)-5,9-di(4-tert-butylphenyl)-7-methyl-5H,9H-[1,4]benzozaboron[2,3,4-kl]phenazonon (abbreviation: Me-tBu4DABNA), N 7 N 7 N 13 Fused heteroaromatic compounds containing nitrogen and boron, such as N13,5,9,11,15-octaphenyl-5H,9H,11H,15H-[1,4]benzozaborono[2,3,4-kl][1,4]benzozaborono[4',3',2':4,5][1,4]benzozaborono[3,2-b]phenazaboron-7,13-diamine (abbreviation: v-DABNA), 2-(4-tert-butylphenyl)benzo[5,6]indole[3,2,1-jk]benzo[b]carbazole (abbreviation: tBuPBibc), especially those with a diaza-boron-naphtho-anthracene skeleton, have narrow emission spectra and can produce blue luminescence with good color purity, and therefore can be used appropriately.

[0173] In addition to the above, 9,10,11-tris[3,6-bis(1,1-dimethylethyl)-9H-carbazole-9-yl]-2,5,15,18-tetra(1,1-dimethylethyl)indolo[3,2,1-de]indolo[3',2',1':8,1][1,4]benzozaboro[2,3,4-k1]phenazaboro (abbreviated as: BBCz-G), 9,11-bis[3,6-bis(1,1-dimethylethyl)-9H-carbazole-9-yl]-2,5,15,18-tetra(1,1-dimethylethyl)indolo[3,2,1-de]indolo[3',2',1':8,1][1,4]benzozaboro[2,3,4-k1]phenazaboro (abbreviated as: BBCz-Y), etc. can also be used appropriately.

[0174] When a phosphorescent material is used as a luminescent material in the luminescent layer, a metal complex is preferred, and an iridium complex or a platinum complex is particularly preferred. Examples of such materials include the following.

[0175] Examples of organometallic iridium complexes with a 4H-triazole skeleton include tri{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III) (abbreviated as [Ir(mpptz-dmp)3]) and tri(5-methyl-3,4-diphenyl-4H-1,2,4-triazol)iridium(III) (abbreviated as [Ir(Mptz)3]). Organometallic iridium complexes with a 1H-triazole skeleton, such as tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole]iridium(III) (abbreviated as [Ir(Mptzl-mp)3]) and tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazole)iridium(III) (abbreviated as [Ir(Prptz1-Me)3]); fac-tris[1-(2,6-diisopropylphenyl) [Ir(iPrpim)3]tri[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviated as [Ir(dmpimpt-Me)3]), [Ir(dmpimpt-Me)3]tri[2-{1-[2,6-bis(1-methylethyl)phenyl]-1H-imidazo-2-yl-κN] Organometallic iridium complexes with an imidazole skeleton, such as 3'-4-cyanophenyl-κC)iridium(III) (abbreviated as CNImIr); organometallic complexes with a benzimidazole skeleton, such as tris[(6-tert-butyl-3-phenyl-2H-imidazo[4,5-b]pyrazin-1-yl-κC2)phenyl-κC]iridium(III) (abbreviated as [Ir(cb)3]); and bis[2-(4',6'-difluorophenyl)pyridinium-N,C 2’ Iridium(III) tetrakis(1-pyrazolyl)borate (abbreviated as: FIr6), bis[2-(4',6'-difluorophenyl)pyridinium-N,C 2’ Iridium(III) pyridine carboxylate (abbreviated as FIRPIC), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinium-N,C 2’ Iridium(III)pyridinecarboxylate (abbreviated as: [Ir(CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyridinium-N,C 2’ Organometallic iridium complexes such as iridium(III) acetylacetone (abbreviated as FIracac) with phenylpyridine derivatives having electron-withdrawing groups as ligands. These substances are compounds that emit blue phosphorescence and have emission peaks in the wavelength region of 450 nm to 520 nm.

[0176] In addition, examples include: tris(4-methyl-6-phenylpyrimidine)iridium(III) (abbreviated as [Ir(mppm)3]), tris(4-tert-butyl-6-phenylpyrimidine)iridium(III) (abbreviated as [Ir(tBuppm)3]), (acetylacetonate)bis(6-methyl-4-phenylpyrimidine)iridium(III) (abbreviated as [Ir(mppm)2(acac)]), (acetylacetonate)bis(6-tert-butyl-4-phenylpyrimidine)iridium(III) (abbreviated as [Ir(tBuppm)2(acac)]), (acetylacetonate)bis[6-(2-norborneol)-4-phenylpyrimidine]iridium(III) (abbreviated as [Ir(nbppm)2(acac)]), (acetylacetonate)bis[5-methyl Organometallic iridium complexes with a pyrimidine skeleton, such as 6-(2-methylphenyl)-4-phenylpyrimidinium-iridium(III) (abbreviated as [Ir(mpmppm)2(acac)]) and (acetylacetonium-ionium)bis(4,6-diphenylpyrimidinium-ionium(III)) (abbreviated as [Ir(dppm)2(acac)]); organometallic iridium complexes with a pyrazine skeleton, such as (acetylacetonium-ionium)bis(3,5-dimethyl-2-phenylpyrazine-ionium(III)) (abbreviated as [Ir(mppr-Me)2(acac)]) and (acetylacetonium-ionium)bis(5-isopropyl-3-methyl-2-phenylpyrazine-ionium(III)) (abbreviated as [Ir(mppr-iPr)2(acac)]); tris(2-phenylpyridinium-N,C 2’ Iridium(III) (abbreviated as: [Ir(pPy)3]), bis(2-phenylpyridinium-N,C) 2’ Iridium(III) acetylacetone (abbreviated as: [Ir(PPy)2(acac)]), bis(benzo[h]quinoline)iridium(III) acetylacetone (abbreviated as: [Ir(bzq)2(acac)]), tri(benzo[h]quinoline)iridium(III) (abbreviated as: [Ir(bzq)3]), tri(2-phenylquinoline-N,C 2’ Iridium(III) (abbreviated as: [Ir(pq)3]), bis(2-phenylquinoline-N,C) 2’ Iridium(III)acetylacetone (abbreviated as: [Ir(pq)2(acac)]), [2-d3-methyl-8-(2-pyridyl-κN)benzofurano[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridyl-κN) 2[2-(methyl-d3)-8-[4-(1-methylethyl-1-d)-2-pyridyl-κN]benzofurano[2,3-b]pyridin-7-yl-κC]bis[5-(methyl-d3)-2-[5-(methyl-d3)-2-pyridinyl-κN]phenyl-κC]iridium(III) (abbreviated as: Ir(5mtpy-d6)2(mbfpypy-iPr-d4)), [2-methyl-d3)-8-(2-pyridinyl-κN)benzofurano[2,3-b]pyridinyl-κC]bis[2-(2-pyridinyl-κN)phenyl [-κC]iridium(III) (abbreviated as: [Ir(ppy)2(mbfpypy-d3)]), [2-(4-methyl-5-phenyl-2-pyridyl-κN)phenyl-κC]bis[2-(2-pyridyl-κN)phenyl-κC]iridium(III) (abbreviated as: [Ir(ppy)2(mdppy)]), [2-(4-d3-methyl-5-phenyl-2-pyridyl-κN2)phenyl-κC]bis[2-(5-d3-methyl-2-pyridyl-κN2)phenyl-κC]iridium(III) (abbreviated as: [Ir(5mppy-d3)2(mdppy-d3)]), [2-methyl-8-(2-pyridyl-κN)benzofurano[2,3- [b]pyridine-κC]bis[2-(2-pyridyl-κN)phenyl-κC]iridium(III) (abbreviated as: [Ir(ppy)2(mbfpypy)]), tri{2-[5-(methyl-d3)-4-phenyl-2-pyridyl-κN]phenyl-κC}iridium(III) (abbreviated as: Ir(5m4dppy-d3)3) and other organometallic iridium complexes with a pyridine skeleton, (2-{1-(5-tert-butylbiphenyl-2-yl)-4-[3-tert-butyl-5-(4-phenyl-2-pyridyl-κN)phenyl-κC6]-2-benzimidazolyl-κN3}-4,6-di-tert-butylphenol-κO)platinum(II) (abbreviated as: Pt(tBudppymmt) Organometallic platinum complexes such as Bubiz-tBubp), [2-(4-(3,5-di-tert-butylphenyl)-6-{3-[4-(5'-tert-butyl[1,1':3',1”-terphenyl]-2'-yl)-2-pyridyl-κN]phenyl-κC2}-2-pyridyl-κN)phenol-κO]platinum(II) (abbreviated as Pt(4tButpppypyp-mmtBup)), and rare earth metal complexes such as tri(acetylacetone)(monophanyline)terbium(III) (abbreviated as [Tb(acac)3(Phen)]) are all present. These substances are primarily compounds exhibiting green phosphorescence and a emission peak in the 500 nm to 600 nm wavelength region.Furthermore, organometallic iridium complexes with a pyrimidine framework are particularly preferred due to their exceptionally high reliability and luminescence efficiency.

[0177] In addition, examples of organogold compounds with a pyrimidine skeleton include: (diisobutyrylmethane)bis[4,6-bis(3-methylphenyl)pyrimidinyl]iridium(III) (abbreviated as: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinyl](dineopentaylmethane)iridium(III) (abbreviated as: [Ir(5mdppm)2(dpm)]), and bis[4,6-bis(naphthyl-1-yl)pyrimidinyl](dineopentaylmethane)iridium(III) (abbreviated as: [Ir(d1npm)2(dpm)]). Organometallic iridium complexes with a pyrazine skeleton, such as (acetylacetonate)bis(2,3,5-triphenylpyrazine)iridium(III) (abbreviated as [Ir(tppr)2(acac)]), bis(2,3,5-triphenylpyrazine)(dinepentylmethane)iridium(III) (abbreviated as [Ir(tppr)2(dpm)]), and (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxaloline]iridium(III) (abbreviated as [Ir(Fdpq)2(acac)]); tris(1-phenylisoquinoline-N,C 2’ Iridium(III) (abbreviated as: [Ir(piq)3]), bis(1-phenylisoquinoline-N,C) 2’ Organometallic iridium complexes with a pyridine skeleton include iridium(III) acetylacetone (abbreviated as [Ir(piq)2(acac)]), (3,7-diethyl-4,6-nonanedione-κO4,κO6)bis[2,4-dimethyl-6-[7-(1-methylethyl)-1-isoquinolinyl-κN]phenyl-κC]iridium(III), (3,7-diethyl-4,6-nonanedione-κO4,κO6)bis[2,4-dimethyl-6-[5-(1-methylethyl)-2-quinolinyl-κN]phenyl-κC]iridium(III). The compounds include platinum complexes such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as PtOEP); and rare earth metal complexes such as tris(1,3-diphenyl-1,3-propanedionato) (monophenanthroline) europium(III) (abbreviated as [Eu(DBM)3(Phen)]) and tris[1-(2-thiophenecarboxyl)-3,3,3-trifluoroacetone] (monophenanthroline) europium(III) (abbreviated as [Eu(TTA)3(Phen)]). These substances are red phosphorescent compounds with emission peaks in the 600 nm to 700 nm wavelength region. Furthermore, organometallic iridium complexes with a pyrazine framework exhibit excellent red luminescence.

[0178] In addition to the phosphorescent compounds mentioned above, other known phosphorescent compounds may also be used.

[0179] Fullerenes and their derivatives, acridines and their derivatives, and eosin derivatives can be used as TADF materials. In addition, metal porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd) can also be used. Examples of metalloporphyrins include, for instance, protoporphyrin-tin fluoride complexes represented by the following structural formulas: protoporphyrin-tin fluoride complex (SnF2(Proto IX)), mesotoporphyrin-tin fluoride complex (SnF2(Meso IX)), hematoporphyrin-tin fluoride complex (SnF2(Hemato IX)), tetramethyl coprophyrin-tin fluoride complex (SnF2(Copro III-4Me), octaethylporphyrin-tin fluoride complex (SnF2(OEP)), protoporphyrin-tin fluoride complex (SnF2(Etio I)), and octaethylporphyrin-platinum chloride complex (PtCl2OEP).

[0180] [Chemical Formula 34]

[0181] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazole-11-yl)-1,3,5-triazine (abbreviated as: PIC-TRZ), 9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviated as: PCCzTzn), 2-{4-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviated as: PCCzPTzn), 2-[4-(10H-phenoxazine-10-yl)phenyl]-4,6-diphenyl-1, Heterocyclic compounds such as 3,5-triazine (PXZ-TRZ), 3-[4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (PPZ-3TPT), 3-(9,9-dimethyl-9H-acridin-10-yl)-9H-oxazanthracene-9-one (ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridin)phenyl]sulfone (DMAC-DPS), and 10-phenyl-10H,10'H-spiro[acridin-9,9'-anthracene]-10'-one (ACRSA) possessing one or both π-electron-rich and π-electron-deficient heterocyclic rings are preferred. These heterocyclic compounds exhibit high electron and hole transport properties due to the presence of both π-electron-rich and π-electron-deficient heterocyclic rings. Among the skeletons with π-electron-deficient heteroaromatic rings, pyridine, diazine (pyrimidine, pyrazine, pyridazine), and triazine skeletons are stable and reliable, and are therefore preferred. In particular, benzofuran-pyrimidine, benzothiophene-pyrimidine, benzofuran-pyrazine, and benzothiophene-pyrazine skeletons are highly acceptor and reliable, and are therefore preferred. Furthermore, among the skeletons with π-electron-rich heteroaromatic rings, acridine, phenoxazine, phenothiazine, furan, thiophene, and pyrrole skeletons are stable and reliable, and at least one of these skeletons is preferred. Moreover, dibenzofuran skeletons are preferred as furan skeletons, and dibenzothiophene skeletons are preferred as thiophene skeletons. As pyrrole skeletons, indole, carbazole, indole-carbazole, bicarbazole, and 3-(9-phenyl-9H-carbazole-3-yl)-9H-carbazole skeletons are particularly preferred. In substances where π-electron-rich and π-electron-deficient heteroaromatic rings are directly bonded, the π-electron-rich ring exhibits high electron-donating and electron-accepting properties, while the energy difference between the S1 and T1 energy levels decreases, resulting in highly efficient thermally activated delayed fluorescence. Therefore, it is particularly preferred. Note that aromatic rings bonded with electron-withdrawing groups such as cyano groups can also be used instead of π-electron-deficient heteroaromatic rings. Furthermore, aromatic amine skeletons, phenazine skeletons, etc., can be used as π-electron-rich skeletons.Furthermore, as π-electron-deficient skeletons, the following can be used: oxanthracene skeleton, thioxanthene dioxide skeleton, oxadiazole skeleton, triazole skeleton, imidazole skeleton, anthraquinone skeleton, boron-containing skeletons such as phenylborane or boranthrene, aromatic or heteroaromatic rings with nitrile or cyanobenzene, carbonyl skeletons such as benzophenone, phosphine oxide skeleton, sulfone skeleton, etc. Thus, π-electron-deficient and π-electron-rich skeletons can be used to replace at least one of the π-electron-deficient and π-electron-rich heteroaromatic rings.

[0182] [Chemical Formula 35]

[0183] TADF materials refer to materials with a small energy difference between the S1 and T1 levels and the ability to convert triple excitation energy into single excitation energy through antisystem crossing. Therefore, they can upconvert triple excitation energy into single excitation energy (antisystem crossing) with minimal thermal energy, efficiently generating singlet excited states. Furthermore, triple excitation energy can be converted into luminescence.

[0184] Exciplexes formed by two substances in an excited state have the function of converting triple excitation energy into single excitation energy due to the extremely small difference between the S1 and T1 energy levels.

[0185] Note that the phosphorescence spectrum observed at low temperatures (e.g., 77K to 10K) can be used as an indicator of the T1 energy level. For TADF materials, it is preferable that the difference between S1 and T1 is 0.3 eV or less, more preferably 0.2 eV or less, when the wavelength energy of the extrapolated line obtained by drawing a tangent at the tail of the short-wavelength side of the fluorescence spectrum is taken as the S1 energy level and the wavelength energy of the extrapolated line obtained by drawing a tangent at the tail of the short-wavelength side of the phosphorescence spectrum is taken as the T1 energy level.

[0186] Furthermore, when using TADF material as the luminescent material, the S1 energy level of the host material is preferably higher than that of the TADF material. Additionally, the T1 energy level of the host material is preferably higher than that of the TADF material.

[0187] As the main material of the light-emitting layer, various carrier transport materials such as materials with electron transport properties and / or materials with hole transport properties, the aforementioned TADF materials, etc., can be used.

[0188] As a material with hole transport capabilities, organic compounds having an amine skeleton or a π-electron-rich heteroaromatic ring skeleton are preferred. The π-electron-rich heteroaromatic ring is preferably a fused aromatic ring comprising at least one of an acridine skeleton, a phenoxazine skeleton, a phenothiazine skeleton, a furan skeleton, a thiophene skeleton, and a pyrrole skeleton; specifically, a carbazole ring, a dibenzothiophene ring, or a ring fused with an aromatic ring or heteroaromatic ring.

[0189] Such hole-transporting organic compounds more preferably have at least one of a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton, and an anthracene skeleton. In particular, they can be aromatic amines having substituents comprising a dibenzofuran ring or a dibenzothiophene ring, aromatic monoamines comprising a naphthyl ring, or aromatic monoamines in which a 9-fluorenyl group is bonded to the nitrogen of the amine via an arylene group. Note that when these hole-transporting organic compounds are substances comprising N,N-bis(4-biphenyl)amino groups, long-lifetime light-emitting devices can be manufactured, and therefore they are preferred.

[0190] Examples of such organic compounds include: 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminebiphenyl (TPD), N,N'-bis(9,9'-spirobis[9H-fluorene]-2-yl)-N,N'-diphenyl-4,4'-diaminebiphenyl (BSPB), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BPAFLP), 4-phenyl-3'-(9-phenylfluorene-9-yl)triphenylamine (mBPAFLP), and 4-phenyl-4'- -(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBA1BP), 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)triphenylamine (abbreviation: PCNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]fluorene-2-amine (abbreviation: PCBAF), N- Compounds with an aromatic amine skeleton, such as phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobis[9H-fluorene]-2-amine (abbreviated as PCBASF); compounds with a carbazole skeleton, such as 1,3-bis(N-carbazolyl)benzene (abbreviated as mCP), 4,4'-bis(N-carbazolyl)biphenyl (abbreviated as CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviated as CzTP), and 3,3'-bis(9-phenyl-9H-carbazole) (abbreviated as PCCP); and compounds with a carbazole skeleton, such as 4,4',4”-(benzyl-1,3,5-triyl)tris(dibenzothiophene) (abbreviated as DBT3). Compounds with a thiophene skeleton, such as 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); and compounds with a furan skeleton, such as 4,4',4”-(benzyl-1,3,5-triyl)tris(dibenzofuran) (abbreviated as DBF3P-II) and 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviated as mmDBFFLBi-II). Among these, compounds with an aromatic amine skeleton and compounds with a carbazole skeleton are preferred due to their good reliability, high hole transport properties, and ability to reduce the driving voltage. Furthermore, organic compounds with hole transport properties, exemplified as hole transport layers, can also be used.

[0191] As a material with electron transport properties, it is preferable to use a material with an electron mobility of 1×10⁻⁶ when the square root of the electric field strength [V / cm] is 600. -7 cm 2 / Vs or more, preferably 1×10 -6 cm 2 Substances with a value of / Vs or higher. Furthermore, any substance other than those mentioned above may be used, provided that its electron transport capacity is higher than its hole transport capacity.

[0192] As materials with electron transport properties, preferred materials include metal complexes such as bis(10-hydroxybenzo[h]quinoline)beryllium(II) (abbreviated as BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO), and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ), as well as organic compounds including π-electron-deficient heteroaromatic rings. Examples of organic compounds with π-electron-deficient heteroaromatic skeletons include organic compounds containing heteroaromatic rings with azole skeletons, organic compounds containing heteroaromatic rings with pyridine skeletons, organic compounds containing heteroaromatic rings with diazine skeletons, and organic compounds containing heteroaromatic rings with triazine skeletons.

[0193] Organic compounds containing heteroaromatic rings with a diazine (pyrimidine, pyrazine, or pyridazine) skeleton, organic compounds containing heteroaromatic rings with a pyridine skeleton, or organic compounds containing heteroaromatic rings with a triazine skeleton are preferred due to their good reliability. In particular, organic compounds containing heteroaromatic rings with a diazine (pyrimidine or pyrazine) skeleton and organic compounds containing heteroaromatic rings with a triazine skeleton exhibit high electron transport properties, which helps to reduce the driving voltage. Furthermore, benzofuran-pyrimidine skeletons, benzothiophene-pyrimidine skeletons, benzofuran-pyrazine skeletons, and benzothiophene-pyrazine skeletons are preferred due to their high acceptor activity and reliability.

[0194] Examples of organic compounds with π-electron-deficient heteroaromatic ring skeletons include: 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated: PBD), 3-(4-biphenyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviated: TAZ), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazole-2-yl)phenyl]-9H-carbazole (abbreviated: CO11), 2,2',2”-(1,3,5-phenyltriyl)tris(1-phenyl-1H-benzimidazole) (abbreviated: TPBI), 2-[3- [(dibenzothiophene-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) and other organic compounds with azole skeletons; 3,5-bis[3-(9H-carbazole-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tris[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), phenanthroline (abbreviation: Bphen), copper hydroxide (abbreviation: BCP), 2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen), 2,2'-(1,3-phenylene)bis(9-phenyl) Organic compounds containing heteroaromatic rings with a pyridine skeleton, such as 2-[3-(2-triphenylene)phenyl]-1,10-phenanthroline (mPPhen2P), 2-[3-(2-triphenylene)phenyl]-1,10-phenanthroline (mTpPPhen), 2-phenyl-9-(2-triphenylene)-1,10-phenanthroline (Ph-TpPhen), 2-[4-(9-phenanthyl)-1-naphthyl]-1,10-phenanthroline (PnNPhen), and 2-[4-(2-triphenylene)phenyl]-1,10-phenanthroline (pTpPPhen); and 2-[3-(dibenzothiophene-4-yl)phenyl]dibenzo[f,h]quinoxaline (2mDBTPDBq-II), etc. 2-[3'-(dibenzothiophene-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazole-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4'-(9-phenyl-9H-carbazole-3-yl)-3,1'-biphenyl-1-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mpPCBPDBq), 2-[4-(3,6-diphenyl-9H-carbazole-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzothiophene-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazole-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzPDBq-III), 2-[3-(dibenzothiophene-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(dibenzothiophene-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzPDBq-III), 2-[3'-(dibenzothiophene-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(dibenzothiophene-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzPDBq-h] Quinoxaline (abbreviation: 7mDBTPDBq-II), 6-[3-(dibenzothiophene-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II), 9-[3'-(dibenzothiophene-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furano[2,3-b]pyrazine (abbreviation: 9mDBtBPNfpr), 9-[3'-(dibenzothiophene-4-yl)biphenyl-4-yl]naphtho[1',2':4,5]furano[2,3-b]pyrazine (abbreviation: 9pmDBtBPNfpr), 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4 ,6-bis[3-(dibenzothiophene-4-yl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazole-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), 9,9'-[pyrimidine-4,6-diylbis(biphenyl-3,3'-diyl)]bis(9H-carbazole) (abbreviation: 4,6mCzBP2Pm), 8-(biphenyl-4-yl)-4-[3-(dibenzothiophene-4-yl)phenyl]-[1]benzofuran[3,2-d]pyrimidine (abbreviation: 8BP-4mDBtPBfpm), 3,8-bis[3-(dibenzothiophene-4-yl)phenyl]benzofuran[2,3-b] Pyrazine (abbreviation: 3,8mDBtP2Bfpr), 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofurano[3,2-d]pyrimidine (abbreviation: 4,8mDBtP2Bfpm), 8-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furano[3,2-d]pyrimidine (abbreviation: 8mDBtBPNfpm), 8-([2,2'-binaphthyl]-6-yl)-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofurano[3,2-d]pyrimidine (abbreviation: 8(βN2)-4mDBtPBfpm), 8-(p-terphenyl-3-yl)-4-[3 -(dibenzothiophene-4-yl)phenyl]-[1]benzofuran[3,2-d]pyrimidine (abbreviation: 8mpTP-4mDBtPBfpm), 2,2'-(pyridin-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'-(pyridin-2,6-diyl)bis{4-[4-(2-naphthyl)phenyl]-6-phenylpyrimidine} (abbreviation: 2,6(NP-PPm)2Py), 6-(biphenyl-3-yl)-4-[3,5-Bis(9H-carbazole-9-yl)phenyl]-2-phenylpyrimidine (abbreviation: 6mBP-4Cz2PPm), 2,6-bis(4-naphthyl-1-ylphenyl)-4-[4-(3-pyridyl)phenyl]pyrimidine (abbreviation: 2,4NP-6PyPPm), 4-[3,5-bis(9H-carbazole-9-yl)phenyl]-2-phenyl-6-(biphenyl-4-yl)pyrimidine (abbreviation: 6BP-4Cz2PPm), 7-[4-(9-phenyl-9H-carbazole-2-yl)quinazolin-2-yl]-7H-dibenzo[c,g]carbazole (abbreviation: PC-cgDBCzQz), 11-[3'-(dibenzothiophene-4-yl)biphenyl-3-yl]phenanthrene[9',10':4,5] Organic compounds with a diazine skeleton, such as furano[2,3-b]pyrazine (abbreviation: 11mDBtBPPnfpr); 2-(biphenyl-4-yl)-4-phenyl-6-(9,9'-spirobis[9H-fluorene]-2-yl)-1,3,5-triazine (abbreviation: BP-SFTzn), 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-8-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPTzn), 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-6-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPTzn-02), 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-triazin-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), 2-[3'-(9,9-dimethyl-9H-fluorene-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn), 5-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-7,7-dimethyl-5H,7H-indo[2,1-b]carbazole (abbreviation: :mINc(II)PTzn), 2-{3-[3-(dibenzothiophene-4-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mDBtBPTzn), 2,4,6-tris[3'-(pyridin-3-yl)biphenyl-3-yl]-1,3,5-triazine (abbreviation: TmPPPyTz), 2,4,6-tris(2-pyridinyl)-1,3,5-triazine (abbreviation: 2Py3Tzn), 2-[3-(2,6-dimethyl-3-pyridinyl)-5-(9-phenanthyl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mPn-mDMePyPTzn), 11-[4-(biphenyl-4-yl)-6-phenyl-1,3,5-Triazine-2-yl]-11,12-dihydro-12-phenyl-indolo[2,3-a]carbazole (abbreviation: BP-Icz(II)Tzn), 2-[3'-(triphenyl-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mTpBPTzn), 3-[9-(4,6-diphenyl-1,3,5-triazine-2-yl)-2-dibenzofuranyl]-9 -Phenylacetyl-9H-carbazole (abbreviation: PCDBfTzn), 2-(biphenyl-3-yl)-4-phenyl-6-[8-([1,1':4',1”-terphenyl]-4-yl)-1-dibenzofuranyl}-1,3,5-triazine (abbreviation: mBP-TPDBfTzn), 2-[4-(2-naphthyl)phenyl]-4-phenyl-6-spiro[9H-fluorene-9,9'-[9H]oxanthracene]-4-yl Organic compounds containing heteroaromatic rings with a triazine skeleton, such as βNP-SFx(4)Tzn, 2-phenyl-4,6-bis[3-(triphenylsilyl)phenyl]-1,3,5-triazine (mSiTrz), and 9,9'-{6-[3-(triphenylsilyl)phenyl]-1,3,5-triazine-2,4-diyl}bis(9H-carbazole) (SiTrzCz2), are preferred. Furthermore, organic compounds containing heteroaromatic rings with a diazine skeleton, pyridine skeletons, or triazine skeletons are preferred due to their high reliability. In particular, organic compounds containing heteroaromatic rings with a diazine (pyrimidine or pyrazine) skeleton or triazine skeleton have high electron transport properties, which helps to reduce the driving voltage.

[0195] Since the organic compound represented by general formula (G3) in embodiment 1 is also an organic compound having a pyridine skeleton and a π-electron-deficient heteroaromatic ring skeleton, it can be appropriately used as a material with electron transport properties.

[0196] As a TADF material that can be used as the host material, the same materials mentioned above as TADF materials can be used. When a TADF material is used as the host material, the triple excitation energy generated by the TADF material is converted into a single excitation energy via antisystem crossing and further transferred to the luminescent material, thereby improving the luminous efficiency of the light-emitting device. In this case, the TADF material acts as the energy donor, and the luminescent material acts as the energy acceptor.

[0197] This is highly effective when the luminescent material is a fluorescent luminescent material. Furthermore, to obtain high luminescent efficiency, the S1 energy level of the TADF material is preferably higher than the S1 energy level of the fluorescent luminescent material. Additionally, the T1 energy level of the TADF material is preferably higher than the S1 energy level of the fluorescent luminescent material. Therefore, the T1 energy level of the TADF material is preferably higher than the T1 energy level of the fluorescent luminescent material.

[0198] Furthermore, it is preferable to use a TADF material that exhibits luminescence with a wavelength overlapping the absorption band on the lowest energy side of the fluorescent luminescent material. This allows for efficient transfer of excitation energy from the TADF material to the fluorescent luminescent material, resulting in highly efficient luminescence, and is therefore preferred.

[0199] To efficiently generate a singlet excitation energy from a triplet excitation energy via antisystem crossing, it is preferable to generate carrier recombination within the TADF material. Furthermore, it is preferable that the triplet excitation energy generated in the TADF material does not transfer to the triplet excitation energy of the fluorescent luminescent material. For this purpose, the fluorescent luminescent material preferably has a protecting group surrounding the luminescent body (the backbone that causes luminescence) of the fluorescent luminescent material. This protecting group is preferably a substituent without π bonds, preferably a saturated hydrocarbon; specifically, examples include alkyl groups with 3 or more but less than 10 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 or more but less than 10 carbon atoms, and trialkylsilyl groups with 3 or more but less than 10 carbon atoms; more preferably, multiple protecting groups are preferred. Substituents without π bonds have almost no function in transporting charge carriers, so they have little effect on charge carrier transport or recombination, allowing the TADF material and the luminescent body of the fluorescent luminescent material to be kept apart. Here, the luminescent body refers to the atomic group (backbone) in the fluorescent luminescent material that causes luminescence. The luminescent material preferably has a π-bonded framework, preferably containing an aromatic ring, and more preferably having a fused aromatic ring or a fused heteroaromatic ring. Examples of such luminescent materials include phenanthrene frameworks, stilbene frameworks, acridinone frameworks, phenoxazine frameworks, phenothiazine frameworks, naphthalene frameworks, anthracene frameworks, and fluorene frameworks. The skeleton includes triphenylene skeleton, tetraphenylene skeleton, pyrene skeleton, perylene skeleton, coumarin skeleton, quinacridone skeleton, naphthobisbenzofuran skeleton, etc. In particular, those possessing naphthalene skeleton, anthracene skeleton, fluorene skeleton, etc. Fluorescent materials with skeletons such as triphenylene skeleton, tetraphenylene skeleton, pyrene skeleton, perylene skeleton, coumarin skeleton, quinacridone skeleton, and naphthobisbenzofuran skeleton have high fluorescence quantum yields and are therefore preferred.

[0200] When using a fluorescent luminescent material as the luminescent material, materials with a benzo[a]benzene backbone, especially an anthracene backbone, are preferred as the host material. By using an anthracene backbone as the host material of the fluorescent luminescent material, a luminescent layer with high luminous efficiency and durability can be achieved. Among the anthracene backbone materials used as host materials, those with a diphenylanthracene backbone, especially 9,10-diphenylanthracene, are chemically stable and therefore preferred. Furthermore, when the host material has a carbazole backbone, hole injection / transport is improved, which is also preferred. In the case of a benzo[a]carbazole backbone with a fused benzene ring to a carbazole backbone, its HOMO level is about 0.1 eV higher than that of a host material with a carbazole backbone, facilitating hole injection, which is even more preferable. In particular, when the host material has a dibenzo[a]carbazole backbone, its HOMO level is about 0.1 eV higher than that of a host material with a carbazole backbone, improving not only hole injection but also hole transport and heat resistance, which is also preferred. Therefore, a further preferred material for use as the host material is one having a 9,10-diphenylanthracene framework and a carbazole framework (or a benzo[a]carbazole framework or a dibenzo[a]carbazole framework). Note that from the viewpoint of hole injection / transportation described above, a benzo[a]fluorene framework or a dibenzo[a]fluorene framework can also be used instead of a carbazole framework. Furthermore, reliability can be ensured without lowering the T1 energy level, so a dibenzofuran framework is preferred.

[0201] Examples of such substances include 9-phenyl-3-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (abbreviated as PCzPA), 3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviated as PCPN), 9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (abbreviated as CzPA), 7-[4-(10-phenyl-9-anthrayl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated as cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthrayl)phenyl]benzo[b]naphtho[1,2-d]furan (abbreviated as 2mBnfPPA), and 9-phenyl-10-[4-(9-phenyl-9H-fluorene-9-yl)bi] [Benzen-4'-yl]anthracene (abbreviation: FLPPA), 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth), 9-(1-naphthyl)-10-(2-naphthyl)anthracene (abbreviation: α,βADN), 2-(10-phenylanthracene-9-yl)dibenzofuran, 2-(10-phenyl-9-anthyl)benzo[b]naphtho[2,3-d]furan (abbreviation: Bnf(II)PhA), 9-(2-naphthyl)-10-[3-(2-naphthyl)phenyl]anthracene (abbreviation: βN-mβNPAnth), 1-{4-[10-(biphenyl-4-yl)-9-anthyl]phenyl}-2-ethyl-1H-benzimidazole (abbreviation: EtBImPBPhA), etc. In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA exhibit very good properties and are therefore preferred.

[0202] Furthermore, the host material can also be a mixture of multiple substances. When using a mixed host material, it is preferable to mix materials with electron transport properties and materials with hole transport properties. By mixing materials with electron transport properties and materials with hole transport properties, it is easier to adjust the transport properties of the light-emitting layer 113 and to more easily control the rebinding region. The weight ratio of the material with hole transport properties to the material with electron transport properties can be 1:19 to 19:1.

[0203] Note that phosphorescent materials can be used as part of the above-described mixture. When used as a fluorescent material, the phosphorescent material can be used as an energy donor to supply excitation energy to the fluorescent material.

[0204] Furthermore, these mixed materials can also be used to form excimer complexes. By selecting a combination of excimer complexes that emit light with wavelengths overlapping the absorption band on the lowest energy side of the luminescent material, energy transfer can be facilitated, resulting in efficient luminescence, which is therefore preferred. Furthermore, this structure allows for a reduction in the driving voltage, making it also preferred.

[0205] Note that at least one of the materials forming the excitocomplex can be a phosphorescent material. This allows for the efficient conversion of the triple excitation energy into a single excitation energy via antisystem crossing.

[0206] Regarding the combination of materials for efficiently forming excitocomplexes, the HOMO energy level of the material with hole transport is preferably higher than or equal to the HOMO energy level of the material with electron transport. Furthermore, the LUMO energy level of the material with hole transport is preferably higher than or equal to the LUMO energy level of the material with electron transport. Note that the LUMO and HOMO energy levels of the material can be determined from the electrochemical properties (reduction potential and oxidation potential) of the material measured by cyclic voltammetry (CV).

[0207] Note that the formation of excitocomplexes can be confirmed, for example, by comparing the emission spectra of a hole-transporting material, the emission spectra of an electron-transporting material, and the emission spectra of a hybrid film formed by mixing these materials. When the emission spectrum of the hybrid film is observed to shift towards a longer wavelength (or to have a new peak on the longer wavelength side) compared to the emission spectra of each material, it indicates the formation of an excitocomplex. Alternatively, by comparing the transient photoluminescence (PL) of a hole-transporting material, the transient PL of an electron-transporting material, and the transient PL of a hybrid film formed by mixing these materials, when a difference in transient response is observed, such as the mixed film having a longer lifetime component or a higher ratio of delayed components compared to the transient PL lifetimes of each material, it indicates the formation of an excitocomplex. Furthermore, the aforementioned transient PL can be referred to as transient electroluminescence (EL). In other words, by comparing the transient EL of a hole-transporting material, the transient EL of an electron-transporting material, and the transient EL of a hybrid film of these materials, and observing the differences in transient responses, the formation of an excitocomplex can be confirmed.

[0208] Electron transport layer 114 is a layer containing a material with electron transport properties. Preferably, the electron transport material has an electron mobility of 1×10⁻⁶ when the square root of the electric field strength [V / cm] is 600. -7 cm 2 / Vs or more, preferably 1×10 -6 cm 2Substances with a value of / Vs or higher. Furthermore, any substance other than those described above can be used, as long as its electron transport capability is higher than its hole transport capability. As the aforementioned organic compounds, organic compounds containing a π-electron-deficient heteroaromatic ring are preferred. For example, one or more of the following are preferred: organic compounds containing a heteroaromatic ring with an azole skeleton, organic compounds containing a heteroaromatic ring with a pyridine skeleton, organic compounds containing a heteroaromatic ring with a diazine skeleton, and organic compounds containing a heteroaromatic ring with a triazine skeleton.

[0209] As an organic compound with electron transport properties that can be used in the electron transport layer 114, the same organic compounds with electron transport properties that can be used in the light-emitting layer 113 can be used. In particular, organic compounds containing heteroaromatic rings with a diazine skeleton, organic compounds containing heteroaromatic rings with a pyridine skeleton, or organic compounds containing heteroaromatic rings with a triazine skeleton are preferred due to their good reliability. In particular, organic compounds containing heteroaromatic rings with a diazine (pyrimidine or pyrazine) skeleton and organic compounds containing heteroaromatic rings with a triazine skeleton have high electron transport properties, which helps to reduce the driving voltage. In particular, organic compounds with a phenanthroline skeleton, such as mTpPPhen, PnNPhen, and mPPhen2P, are preferred, and organic compounds with a phenanthroline dimer structure, such as mPPhen2P, have excellent stability and are therefore more preferred.

[0210] Since the organic compound represented by general formula (G3) in embodiment 1 is also an organic compound with a π-electron-deficient heteroaromatic ring skeleton, it can also be appropriately used as a material with electron transport properties.

[0211] Note that the electron transport layer 114 may also have a stacked structure. The layer in the electron transport layer 114 that contacts the light-emitting layer 113 can also be used as a hole blocking layer. When the electron transport layer that contacts the light-emitting layer is used as a hole blocking layer, it is preferable to use a material whose HOMO energy level is more than 0.5 eV lower than the HOMO energy level of the material in the light-emitting layer 113.

[0212] As the electron injection layer 115, a layer may also be provided containing a compound or complex of an alkali metal or alkaline earth metal such as 8-hydroxyquinoline-lithium (abbreviated as Liq), or 1,1'-pyridine-2,6-diyl-bis(1,3,4,6,7,8-hexahydro-2H-pyrimidino[1,2-a]pyrimidinium) (abbreviated as hpp2Py), or an organic compound represented by general formula (G3) in Embodiment 1. As the electron injection layer 115, an alkali metal or alkaline earth metal or its compound may also be included in a layer formed using a substance with electron transport properties.

[0213] In addition, a charge generation layer 116 can be provided instead of an electron injection layer 115. Figure 1B The charge generation layer 116 is a layer that, by applying a potential, can inject holes into the layer in contact with the cathode side of the layer and inject electrons into the layer in contact with the anode side of the layer. The charge generation layer 116 includes at least a second layer 117 of p-type layers. The second layer 117 is preferably formed using the composite material constituting the hole injection layer 111 described above. Alternatively, the second layer 117 can also be formed by laminating a film containing the acceptor material and a film containing a hole transport material as the constituent material of the composite material. By applying a potential to the second layer 117, electrons and holes are injected into the electron transport layer 114 and the cathode, respectively, causing the light-emitting device to operate. In addition, one embodiment of the present invention uses an organic compound with a low refractive index, and by using it in the second layer 117, a light-emitting device with good external quantum efficiency can be obtained.

[0214] In addition, the charge generation layer 116 preferably includes, in addition to the second p-type layer 117, either or both of the first electron injection buffer layer 119 and the third electron relay layer 118.

[0215] The first layer 119 can use alkali metals, alkaline earth metals, rare earth metals, and compounds of these substances (alkali metal compounds (including oxides such as lithium oxide, halides, carbonates such as lithium carbonate or cesium carbonate), alkaline earth metal compounds (including oxides, halides, carbonates) or rare earth metal compounds (including oxides, halides, carbonates)) and other substances with high electron injection capacity.

[0216] Furthermore, when the first layer 119 contains an electron-transporting substance and a donor substance, the donor substance may include alkali metals, alkaline earth metals, rare earth metals, and compounds of these substances (alkali metal compounds (including oxides such as lithium oxide, halides, carbonates such as lithium carbonate or cesium carbonate), alkaline earth metal compounds (including oxides, halides, and carbonates), or rare earth metal compounds (including oxides, halides, and carbonates)). Organic compounds such as tetrathianaphthacene (TTN), nickel-cadmium, and decamethylnickel-cadmium may also be used. Additionally, the electron-transporting substance may be the same material described above for the electron transport layer 114.

[0217] Furthermore, when the first layer 119 is formed by including an electron transport material and a donor material, it is preferred that the rise of the driving voltage during photolithography is suppressed by including an organic compound of one aspect of the present invention represented by the above general formula (G3).

[0218] The third layer 118 contains at least an electron-transporting material and is capable of preventing the interaction between the first layer 119 and the second layer 117, while facilitating electron transfer. Preferably, the LUMO energy level of the electron-transporting material contained in the third layer 118 is set between the LUMO energy level of the acceptor material in the second layer 117 and the LUMO energy level of the material contained in the layer in the electron transport layer 114 that is in contact with the charge-generating layer 116. Specifically, the LUMO energy level of the electron-transporting material in the third layer 118 is -5.0 eV or higher, preferably -5.0 eV or higher and -3.0 eV or lower. Furthermore, phthalocyanine materials or metal complexes having metal-oxygen bonds and aromatic ligands are preferably used as the electron-transporting material in the third layer 118.

[0219] The second electrode 102 is an electrode that includes a cathode. The second electrode 102 may also have a layered structure, in which case the layer in contact with the organic compound layer 103 is used as the cathode. As the material forming the cathode, metals, alloys, conductive compounds, and mixtures thereof with low work functions (specifically below 3.8 eV) can be used. Specific examples of such cathode materials include alkali metals such as lithium (Li) or cesium (Cs), elements belonging to Group 1 or Group 2 of the periodic table such as magnesium (Mg), calcium (Ca), or strontium (Sr), alloys containing them (MgAg, AlLi), compounds (lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), etc.), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them. However, by providing an electron injection layer 115 or a thin film of a material with a small work function between the second electrode 102 and the electron transport layer, various conductive materials such as Al, Ag, ITO, indium oxide-tin oxide containing silicon or silicon oxide, etc., can be used as cathodes regardless of the size of the work function.

[0220] When the second electrode 102 is made of a material that is transmissive to visible light, a light-emitting device that emits light from one side of the second electrode 102 can be formed.

[0221] These conductive materials can be deposited using dry methods such as vacuum evaporation and sputtering, as well as inkjet printing and spin coating. Alternatively, they can be formed using wet methods such as sol-gel processes or wet methods using pastes of metallic materials.

[0222] Furthermore, various methods, whether dry or wet, can be used to form the organic compound layer 103. For example, vacuum evaporation, gravure printing, offset printing, screen printing, inkjet printing, or spin coating can also be used.

[0223] In addition, the aforementioned electrodes or layers can also be formed by using different deposition methods.

[0224] Next, refer to Figure 1C This describes a light-emitting device (also called a stacked element or series element) with a structure having multiple light-emitting units stacked together. This light-emitting device has multiple light-emitting units between the anode and cathode. Each light-emitting unit has a... Figure 1A The organic compound layer 103 shown has a structure that is substantially the same. That is to say, it can be said that... Figure 1C The light-emitting device shown is a light-emitting device with multiple light-emitting units, while Figure 1A or Figure 1B The light-emitting device shown is a light-emitting device with one light-emitting unit.

[0225] exist Figure 1C In this structure, a first light-emitting unit 511 and a second light-emitting unit 512 are stacked between the first electrode 501 and the second electrode 502, and an intermediate layer 513 is disposed between the first light-emitting unit 511 and the second light-emitting unit 512. The first electrode 501 and the second electrode 502 respectively correspond to... Figure 1A The first electrode 101 and the second electrode 102 are used in the process, and can be applied to... Figure 1A The same material as described. Furthermore, the first light-emitting unit 511 and the second light-emitting unit 512 may have the same structure or different structures.

[0226] The intermediate layer 513 has the function of injecting electrons into one light-emitting unit and holes into another light-emitting unit when a voltage is applied to the first electrode 501 and the second electrode 502. In other words, in Figure 1C In this process, when a voltage is applied such that the potential of the anode is higher than that of the cathode, the intermediate layer 513 only needs to be a layer that injects electrons into the first light-emitting unit 511 and holes into the second light-emitting unit 512.

[0227] The intermediate layer 513 preferably has the same as Figure 1B The charge generation layer 116 shown has the same structure. Because the composite material of organic compound and metal oxide has good carrier injection and carrier transport properties, it is possible to achieve low voltage drive and low current drive.

[0228] In particular, the first layer 119 of the intermediate layer 513 preferably contains an organic compound represented by the general formula (G3) shown in Embodiment 1. When an organic compound represented by the general formula (G3) shown in Embodiment 1 is included, electron injection can be improved, thereby enabling a light-emitting device with a low driving voltage.

[0229] Furthermore, by coordinating the organic compound represented by general formula (G3) shown in Embodiment 1 with the organic compound represented by general formula (G3), the donorness of the metal or metal compound can be improved. Therefore, even if the organic compound layer 503 is exposed to the atmospheric atmosphere, the rise in driving voltage can be suppressed by preventing damage to the function of the first layer 119 in the intermediate layer 513, thereby providing a light-emitting device with excellent characteristics.

[0230] That is to say, a series-type light-emitting device including an intermediate layer 513 of a first layer 119 containing an organic compound and a metal or metal compound represented by general formula (G3) as shown in Embodiment 1 can realize a light-emitting device with low driving voltage and good characteristics.

[0231] Furthermore, even when processed using photolithography, which includes an organic compound represented by general formula (G3) as shown in Embodiment 1, and an intermediate layer 513 containing an organic compound, a metal or metal compound, and an organic compound with electron transport properties, the tandem type light-emitting device does not experience a significant increase in driving voltage, and can achieve a light-emitting device with excellent characteristics.

[0232] Note that when the anode side of the light-emitting unit is in contact with the intermediate layer 513, the intermediate layer 513 can function as a hole injection layer of the light-emitting unit, so the light-emitting unit may not have a hole injection layer.

[0233] Furthermore, when the first layer 119 is provided in the intermediate layer 513, since the first layer 119 has the function of an electron injection layer in the light-emitting unit on the anode side, it is not necessary to provide an electron injection layer in the light-emitting unit on the anode side.

[0234] Although Figure 1C The description includes a light-emitting device with two light-emitting units, but similarly, light-emitting devices with three or more light-emitting units stacked can be applied. As in the light-emitting device according to this embodiment, by separating and arranging multiple light-emitting units between a pair of electrodes using an intermediate layer 513, the device can achieve high brightness emission while maintaining low current density and can achieve a long lifespan. Furthermore, a light-emitting device capable of low-voltage driving and low power consumption can be realized.

[0235] Furthermore, by making the emission colors of each light-emitting unit different, the desired color of emission can be obtained from the entire light-emitting device. For example, by obtaining red and green emission colors from the first light-emitting unit and blue emission color from the second light-emitting unit in a light-emitting device with two light-emitting units, a light-emitting device that emits white light throughout the entire device can be obtained.

[0236] The aforementioned organic compound layer 103, first light-emitting unit 511, second light-emitting unit 512, intermediate layer 513, and electrodes can be formed using methods such as vapor deposition (including vacuum vapor deposition), droplet jetting (also known as inkjet printing), coating, and gravure printing. Furthermore, they may also contain low-molecular-weight materials, medium-molecular-weight materials (including oligomers and dendritic polymers), or high-molecular-weight materials.

[0237] This embodiment can be appropriately combined with other embodiments or examples. Furthermore, where multiple structural examples are shown in one embodiment in this specification, these structural examples can be appropriately combined.

[0238] Implementation Method 3 In this embodiment, an example is described of using a light-emitting device according to one aspect of the present invention as a display element of a display device. In this embodiment, the shape of the light-emitting device is shown to be formed using photolithography, but the light-emitting device can also be formed using methods such as high-precision metal masks.

[0239] like Figure 2B As shown, multiple light-emitting devices 130 are formed on the insulating layer 175 and constitute a display device.

[0240] The display device includes a pixel section 177 in which a plurality of pixels 178 are arranged in a matrix. Pixel 178 includes sub-pixels 110R, 110G, and 110B.

[0241] In this specification, etc., the term "subpixel 110" is sometimes used to describe the common features among subpixels 110R, 110G, and 110B. Furthermore, regarding other constituent elements distinguished by letters, reference numerals with omitted letters are sometimes used to describe the common features among these constituent elements.

[0242] Subpixel 110R emits red light, subpixel 110G emits green light, and subpixel 110B emits blue light. Thus, an image can be displayed on pixel unit 177. Note that in this embodiment, only subpixels of three colors—red (R), green (G), and blue (B)—are used as an example for explanation; other colors of subpixels can also be combined. Furthermore, the number of subpixels is not limited to three; it can be four or more. Examples of four subpixels include: a subpixel of four colors—R, G, B, and white (W); a subpixel of four colors—R, G, B, and yellow (Y); and a subpixel of four colors—R, G, B, and infrared (IR); etc.

[0243] In this specification, the row direction is sometimes referred to as the X direction and the column direction as the Y direction. The X direction and the Y direction intersect, for example, perpendicularly.

[0244] exist Figure 2A In the example shown, subpixels of different colors are arranged in the X direction, and subpixels of the same color are arranged in the Y direction. Note that it is also possible to arrange subpixels of different colors in the Y direction and subpixels of the same color in the X direction.

[0245] A connecting portion 140 may be provided on the outer side of the pixel portion 177, and a region 141 may also be provided thereon. The region 141 is provided between the pixel portion 177 and the connecting portion 140. An organic compound layer 103 is provided in the region 141. In addition, a conductive layer 151C is provided in the connecting portion 140.

[0246] exist Figure 2A In the example shown, region 141 and connecting portion 140 are located to the right of pixel portion 177, but there are no particular restrictions on the position of region 141 and connecting portion 140. Furthermore, region 141 and connecting portion 140 may be one or more.

[0247] Figure 2B It is along Figure 2A An example of a cross-sectional view of the dashed-dot line A1-A2 in the diagram. For example... Figure 2B As shown, the display device includes an insulating layer 171, a conductive layer 172 on the insulating layer 171, an insulating layer 173 on the insulating layer 171 and the conductive layer 172, an insulating layer 174 on the insulating layer 173, and an insulating layer 175 on the insulating layer 174. The insulating layer 171 is disposed on a substrate (not shown). The insulating layers 175, 174, and 173 are provided with openings leading to the conductive layer 172, and a plug 176 is disposed such that it is inserted into the openings.

[0248] In the pixel section 177, a light-emitting device 130 is disposed on the insulating layer 175 and the plug 176. A protective layer 131 is disposed to cover the light-emitting device 130. The substrate 120 is attached to the protective layer 131 by a resin layer 122. In addition, it is preferable to provide an inorganic insulating layer 125 and an insulating layer 127 on the inorganic insulating layer 125 between adjacent light-emitting devices 130.

[0249] Figure 2B Cross-sections of multiple inorganic insulating layers 125 and multiple insulating layers 127 are shown, but when viewed from above, the inorganic insulating layers 125 and 127 are preferably formed as a connected layer. That is, the inorganic insulating layers 125 and 127 are preferably insulating layers having openings on the first electrode.

[0250] exist Figure 2BLight-emitting devices 130R, 130G, and 130B are shown as light-emitting devices 130. Light-emitting devices 130R, 130G, and 130B emit light of different colors. For example, light-emitting device 130R can emit red light, light-emitting device 130G can emit green light, and light-emitting device 130B can emit blue light. Alternatively, light-emitting devices 130R, 130G, or 130B can also emit other visible or infrared light. Note that in... Figure 2B In this context, light-emitting devices 130R and 130G, as well as light-emitting devices 130G and 130B, can be referred to as adjacent light-emitting devices.

[0251] One aspect of the display device of the present invention may include a top emission structure that emits light in a direction opposite to that of the substrate on which the light-emitting device is formed. Alternatively, another aspect of the display device of the present invention may include a bottom emission structure.

[0252] The light-emitting device 130R is a light-emitting device that emits red light (preferably phosphorescence), and preferably has the structure shown in Embodiment 2. The light-emitting device 130R includes a first electrode (pixel electrode) composed of conductive layers 151R and 152R, a first layer 135R on the first electrode, a common layer 104 on the first layer 135R, and a second electrode (common electrode) 102 on the common layer 104. The common layer 104 is preferably an electron injection layer or a stack of an electron transport layer and an electron injection layer.

[0253] The light-emitting device 130G is a green light-emitting device (preferably phosphorescent), and preferably has the structure shown in Embodiment 2. The light-emitting device 130G includes a first electrode (pixel electrode) composed of conductive layers 151G and 152G, a first layer 135G on the first electrode, a common layer 104 on the first layer 135G, and a second electrode (common electrode) 102 on the common layer 104. The common layer 104 is preferably an electron injection layer or a stack of an electron transport layer and an electron injection layer.

[0254] The light-emitting device 130B is a light-emitting device that emits blue light (preferably fluorescence), and preferably has the structure shown in Embodiment 2. The light-emitting device 130B includes a first electrode (pixel electrode) composed of conductive layers 151B and 152B, a first layer 135B on the first electrode, a common layer 104 on the first layer 135B, and a second electrode (common electrode) 102 on the common layer 104. The common layer 104 is preferably an electron injection layer or a stack of an electron transport layer and an electron injection layer. Furthermore, the stack of the first layer 135B and the common layer 104 is equivalent to... Figure 1AOrganic compound layer 103 in etc.

[0255] Furthermore, without the common layer 104, the first layer 135 is equivalent to the organic compound layer 103.

[0256] In a light-emitting device, one of the pixel electrode (first electrode) and the common electrode (second electrode) is used as the anode, and the other is used as the cathode. In this embodiment, unless otherwise specified, it is sometimes assumed that the pixel electrode is used as the anode and the common electrode is used as the cathode.

[0257] The first layers 135R, 135G, and 135B are arranged independently in an island shape according to each light-emitting device or each light-emitting color. Note that the first layers 135R, 135G, and 135B preferably do not overlap with each other. Sometimes, the first layer including the multiple light-emitting devices 130 formed in the light-emitting device, such as the first layers 135R, 135G, and 135B, is collectively referred to as the first layer group 135A. By arranging the first layer group 135A in an island shape for each light-emitting device 130, leakage current between adjacent light-emitting devices 130 can be suppressed even in high-definition display devices. As a result, crosstalk can be suppressed, and a display device with extremely high contrast can be realized. In particular, a display device with high current efficiency at low brightness can be realized.

[0258] The island-shaped first layer group 135A is formed by depositing an EL film according to the emission color and processing the EL film using photolithography.

[0259] The first layer 135 is preferably provided in such a way that it covers the top surface and side surface of the first electrode 101 (pixel electrode) of the light-emitting device 130. This makes it easier to increase the aperture ratio of the display device compared to a structure where the end of the first layer 135 is located inside the end of the pixel electrode. Furthermore, by covering the side surface of the pixel electrode of the light-emitting device 130 with the first layer 135, contact between the first electrode 101 and the second electrode 102 can be suppressed, thus preventing short circuits in the light-emitting device 130.

[0260] In one aspect of the display device of the present invention, the first electrode 101 (pixel electrode) of the light-emitting device preferably has a stacked structure. For example, in Figure 2B In the example shown, the first electrode 101 of the light-emitting device 130 has a stacked structure of a conductive layer 151 disposed on one side of the insulating layer 171 and a conductive layer 152 disposed on one side of the organic compound layer.

[0261] As the conductive layer 151, a metallic material can be used, for example. Specifically, 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 thereof can also be used.

[0262] As the conductive layer 152, an oxide containing one or more of indium, tin, zinc, gallium, titanium, aluminum, and silicon can be used. For example, conductive oxides containing one or more of indium oxide, indium tin oxide, indium zinc oxide, zinc oxide, gallium-containing zinc oxide, titanium oxide, gallium-containing indium zinc oxide, aluminum-containing indium zinc oxide, silicon-containing indium tin oxide, and silicon-containing indium zinc oxide are preferred. In particular, silicon-containing indium tin oxide has a large work function, for example, 4.0 eV or more, so it is suitable for use as the conductive layer 152.

[0263] Conductive layer 151 and conductive layer 152 may each have a stacked structure containing multiple layers of different materials. In this case, conductive layer 151 may also include a layer using a material that can be used in conductive layer 152, such as a conductive oxide, and conductive layer 152 may also include a layer using a material that can be used in conductive layer 151, such as a metallic material. For example, when conductive layer 151 has a stacked structure of two or more layers, the layer in contact with conductive layer 152 may be a layer using a material that can be used in conductive layer 152.

[0264] The ends of the conductive layer 151 preferably have a tapered shape. Specifically, the ends of the conductive layer 151 preferably have a tapered shape with a taper angle of less than 90°. At this time, the conductive layer 152 disposed along the side of the conductive layer 151 also has a tapered shape. By making the side of the conductive layer 152 tapered, the coverage of the first layer 135 disposed along the side of the conductive layer 152 can be improved.

[0265] This embodiment can be appropriately combined with other embodiments or examples. Furthermore, where multiple structural examples are shown in one embodiment in this specification, these structural examples can be appropriately combined.

[0266] Implementation Method 4 In this embodiment, a display device according to one aspect of the present invention will be described.

[0267] The display device in this embodiment can be a high-definition display device. Therefore, for example, the display device in this embodiment can be used in the display section of information terminal devices (wearable devices) such as watch-type and bracelet-type devices, as well as in the display section of wearable devices that can be worn on the head, such as head-mounted displays (HMDs) for VR devices and glasses-type AR devices.

[0268] Furthermore, the display device of this embodiment can be a high-resolution display device or a large-screen display device. Therefore, the display device of this embodiment can be used, for example, in the display section of devices such as: electronic devices with large screens, such as television devices, desktop or laptop personal computers, monitors for computers, digital signage, and large game machines such as pinball machines; digital cameras; digital video cameras; digital photo frames; mobile phones; portable game consoles; portable information terminals; and sound reproduction devices.

[0269] [Display Module] Figure 3A A perspective view of display module 280 is shown. Display module 280 includes light-emitting device 100A and FPC 290. Note that the display device included in display module 280 is not limited to display device 100A, but may be any of display devices 100B to 100E, which will be described later.

[0270] The display module 280 includes a substrate 291 and a substrate 292. The display module 280 includes a display section 281. The display section 281 is the image display area in the display module 280, and can display light from each pixel disposed in the pixel section 284.

[0271] Figure 3B This is a three-dimensional schematic diagram of the structure on one side of the substrate 291. A circuit section 282, a pixel circuit section 283 on the circuit section 282, and a pixel section 284 on the pixel circuit section 283 are stacked on the substrate 291. Furthermore, a terminal section 285 for connecting to the FPC 290 is provided on the portion of the substrate 291 that does not overlap with the pixel section 284. The terminal section 285 is electrically connected to the circuit section 282 via a wiring section 286 composed of multiple wirings.

[0272] The pixel unit 284 includes a plurality of pixels 284a arranged periodically. Figure 3B The right side shows a magnified view of pixel 284a. Pixel 284a can adopt various structures described in the above embodiments. Figure 3B In the example, pixel 284a has the same characteristics as... Figure 2A and Figure 2B The same structure as pixel 178 shown.

[0273] The pixel circuit section 283 includes a plurality of pixel circuits 283a arranged periodically.

[0274] A pixel circuit 283a controls the driving of multiple elements included in a pixel 284a.

[0275] The circuit section 282 includes circuitry for driving each pixel circuit 283a of the pixel circuit section 283. For example, it preferably includes one or both of a gate line driving circuit and a source line driving circuit. Furthermore, it may also include at least one of an arithmetic circuit, a storage circuit, and a power supply circuit.

[0276] The FPC290 is used for wiring to supply video signals or power potentials, etc., from the outside to the circuit section 282. Additionally, ICs can be mounted on the FPC290.

[0277] The display module 280 can adopt a structure in which one or both of the pixel circuit section 283 and the circuit section 282 are stacked on the lower side of the pixel section 284, so that the display section 281 can have an extremely high aperture ratio (effective display area ratio).

[0278] Due to its extremely high resolution, the display module 280 is suitable for use in VR devices such as HMDs or glasses-type AR devices. For example, because the display module 280 has a display section 281 with extremely high resolution, even when the user views the display section of the display module 280 through a lens and magnifies the display section, the pixels are not visible, thereby achieving a highly immersive display. Furthermore, not limited to this, the display module 280 can also be applied to electronic devices with relatively small display sections.

[0279] [Display Device 100A] Figure 4A The display device 100A shown includes a substrate 301, light-emitting devices 130R, 130G, 130B, a capacitor 240, and a transistor 310.

[0280] Substrate 301 is equivalent to Figure 3A and Figure 3B The substrate 291 is used in the transistor 310. The transistor 310 is a transistor having a channel formation region in the substrate 301. The substrate 301 can be, for example, a semiconductor substrate such as a single-crystal silicon substrate. The transistor 310 includes a portion of the substrate 301, a conductive layer 311, a low-resistance region 312, an insulating layer 313, and an insulating layer 314. The conductive layer 311 serves as the gate electrode. The insulating layer 313 is located between the substrate 301 and the conductive layer 311 and serves as the gate insulating layer. The low-resistance region 312 is a region in the substrate 301 doped with impurities and serves as the source or drain. The insulating layer 314 covers the sides of the conductive layer 311.

[0281] In addition, a component separation layer 315 is provided between two adjacent transistors 310 in a manner embedded in the substrate 301.

[0282] In addition, an insulating layer 261 is provided to cover the transistor 310, and a capacitor 240 is provided on the insulating layer 261.

[0283] The capacitor 240 includes a conductive layer 241, a conductive layer 245, and an insulating layer 243 located therebetween. The conductive layer 241 is used as one electrode in the capacitor 240, the conductive layer 245 is used as the other electrode in the capacitor 240, and the insulating layer 243 is used as the dielectric of the capacitor 240.

[0284] A conductive layer 241 is disposed on an insulating layer 261 and embedded within an insulating layer 254. The conductive layer 241 is electrically connected to one of the source and drain terminals of the transistor 310 via a connector 271 embedded in the insulating layer 261. An insulating layer 243 is disposed to cover the conductive layer 241. A conductive layer 245 is disposed in the region where it overlaps with the conductive layer 241, separated by the insulating layer 243.

[0285] An insulating layer 255 is provided to cover the capacitor 240. An insulating layer 174 is provided on the insulating layer 255, and an insulating layer 175 is provided on the insulating layer 174. Light-emitting devices 130R, 130G, and 130B are provided on the insulating layer 175. An insulating material is provided in the area between adjacent light-emitting devices.

[0286] An insulating layer 156R is provided such that it overlaps with the side surface of conductive layer 151R; an insulating layer 156G is provided such that it overlaps with the side surface of conductive layer 151G; and an insulating layer 156B is provided such that it overlaps with the side surface of conductive layer 151B. Furthermore, a conductive layer 152R is provided such that it covers conductive layer 151R and insulating layer 156R; a conductive layer 152G is provided such that it covers conductive layer 151G and insulating layer 156G; and a conductive layer 152B is provided such that it covers conductive layer 151B and insulating layer 156B. A sacrificial layer 158R is located on the first layer 135R; a sacrificial layer 158G is located on the first layer 135G; and a sacrificial layer 158B is located on the first layer 135B.

[0287] Conductive layers 151R, 151G, and 151B are electrically connected to one of the source and drain terminals of transistor 310 via plugs 256 embedded in insulating layers 243, 255, 174, and 175, conductive layer 241 embedded in insulating layer 254, and plug 271 embedded in insulating layer 261. The plugs can be made of various conductive materials.

[0288] Furthermore, a protective layer 131 is provided on the light-emitting devices 130R, 130G, and 130B. A substrate 120 is bonded to the protective layer 131 by a resin layer 122. Detailed descriptions of the constituent elements of the light-emitting devices 130 and the substrate 120 can be found in Embodiment 3. The substrate 120 corresponds to... Figure 3A Substrate 292.

[0289] Figure 4B Show Figure 4A The illustrated example is a modified version of the display device 100A. Figure 4B The display device shown includes a color layer 132R, a color layer 132G, and a color layer 132B, and a light-emitting device 130 has a region overlapping one of the color layers 132R, 132G, and 132B. Figure 4B In the display device shown, the light-emitting device 130 can emit white light, for example. In addition, for example, the color layer 132R, color layer 132G and color layer 132B can transmit red light, green light and blue light, respectively.

[0290] [Display device 100B] Figure 5 A perspective view of the display device 100B is shown. Figure 6 A cross-sectional view of the display device 100C is shown.

[0291] The display device 100B has a structure that bonds substrate 352 and substrate 351. Figure 5 In the image, substrate 352 is represented by a dashed line.

[0292] The display device 100B includes a pixel unit 177, a connection unit 140, a circuit 356, and wiring 355, etc. Figure 5 An example is shown where display device 100B is equipped with IC354 and FPC353. Therefore, it is also possible to... Figure 5 The structure shown is referred to as a display module including a display device 100B, an IC (integrated circuit), and an FPC. Here, the substrate of the display device on which connectors such as the FPC are mounted, or the substrate on which the IC is mounted, is referred to as the display module.

[0293] The connecting portion 140 is disposed on the outer side of the pixel portion 177. There may be one or more connecting portions 140. In the connecting portion 140, the common electrode of the light-emitting device is electrically connected to the conductive layer, and power can be supplied to the common electrode.

[0294] For example, a scan line drive circuit can be used as circuit 356.

[0295] Wiring 355 has the function of supplying signals and power to pixel unit 177 and circuit 356. The signals and power are input to wiring 355 from the outside via FPC 353 or from IC 354.

[0296] Figure 5 An example is shown where IC 354 is mounted on substrate 351 using methods such as COG (Chip On Glass) or COF (Chip On Film). IC 354 can be, for example, an IC including scan line drive circuitry or signal line drive circuitry. Note that the display device 100B and display module do not necessarily need to have an IC mounted on them. Alternatively, the IC can also be mounted on an FPC using a COF method.

[0297] Figure 6 An example of a cross-section of a portion of the display device 100B including an area of ​​FPC 353, a portion of circuitry 356, a portion of pixel portion 177, a portion of connection portion 140, and a portion of the area including the end portion is shown.

[0298] [Display Device 100C] Figure 6 The display device 100C shown includes transistors 201 and 205, a light-emitting device 130R that emits red light, a light-emitting device 130G that emits green light, and a light-emitting device 130B that emits blue light, etc., between substrates 351 and 352.

[0299] For details on light-emitting devices 130R, 130G, and 130B, please refer to Embodiment 2.

[0300] Light-emitting device 130R includes a conductive layer 224R, a conductive layer 151R on the conductive layer 224R, and a conductive layer 152R on the conductive layer 151R. Light-emitting device 130G includes a conductive layer 224G, a conductive layer 151G on the conductive layer 224G, and a conductive layer 152G on the conductive layer 151G. Light-emitting device 130B includes a conductive layer 224B, a conductive layer 151B on the conductive layer 224B, and a conductive layer 152B on the conductive layer 151B.

[0301] The conductive layer 224R is connected to the conductive layer 222b included in the transistor 205 through an opening provided in the insulating layer 214. The end of the conductive layer 151R is located outside the end of the conductive layer 224R. The insulating layer 156R is provided in such a way that it includes a region that contacts the side of the conductive layer 151R, and the conductive layer 152R is provided in such a way that it covers the conductive layer 151R and the insulating layer 156R.

[0302] The conductive layers 224G, 151G, 152G, and 156G in the light-emitting device 130G, and the conductive layers 224B, 151B, 152B, and 156B in the light-emitting device 130B, are the same as the conductive layers 224R, 151R, 152R, and 156R in the light-emitting device 130R, so detailed descriptions are omitted.

[0303] The conductive layers 224R, 224G, and 224B have recesses formed in a manner that cover the openings provided in the insulating layer 214. These recesses are filled with layer 128.

[0304] Layer 128 has the function of planarizing the recesses of conductive layers 224R, 224G, and 224B. Conductive layers 151R, 151G, and 151B, which are electrically connected to conductive layers 224R, 224G, and 224B, are disposed on conductive layers 224R, 224G, and 224B. Therefore, the area overlapping the recesses of conductive layers 224R, 224G, and 224B can also be used as a light-emitting area, which can improve the pixel aperture ratio.

[0305] Layer 128 can also be an insulating layer or a conductive layer. Various inorganic insulating materials, organic insulating materials, and conductive materials can be suitably used for layer 128. In particular, layer 128 is preferably formed using an insulating material, and more preferably using an organic insulating material. Layer 128 can, for example, use the organic insulating material described above that can be used in insulating layer 127.

[0306] A protective layer 131 is provided on light-emitting devices 130R, 130G, and 130B. The protective layer 131 and the substrate 352 are bonded together by an adhesive layer 142. A light-shielding layer 157 is provided on the substrate 352. The light-emitting device 130 can be sealed using a solid sealing structure or a hollow sealing structure, etc. Figure 6 In this configuration, the space between substrates 352 and 351 is filled with adhesive layer 142, thus employing a solid sealing structure. Alternatively, an inert gas (such as nitrogen or argon) can be used to fill the space, resulting in a hollow sealing structure. In this case, adhesive layer 142 can also be arranged in a manner that does not overlap with the light-emitting device. Furthermore, a resin different from that used for the frame-shaped adhesive layer 142 can be used to fill the space.

[0307] Figure 6An example is shown below: the connecting portion 140 includes a conductive layer 224C obtained by processing a conductive film identical to conductive layers 224R, 224G, and 224B; a conductive layer 151C obtained by processing a conductive film identical to conductive layers 151R, 151G, and 151B; and a conductive layer 152C obtained by processing a conductive film identical to conductive layers 152R, 152G, and 152B. Furthermore, Figure 6 An example is shown in which the insulating layer 156C is disposed in such a manner that it includes a region that overlaps with the side of the conductive layer 151C.

[0308] Display device 100B is a top-emitting display device. A light-emitting device emits light onto one side of a substrate 352. The substrate 352 is preferably made of a material with high transmittance to visible light. When the light-emitting device emits infrared or near-infrared light, a material with high transmittance to such light is preferably used. The first electrode (pixel electrode) contains a material that reflects visible light, and the second electrode (opposite electrode) contains a material that transmits visible light.

[0309] Insulating layers 211, 213, 215, and 214 are sequentially disposed on substrate 351. A portion of insulating layer 211 serves as the gate insulating layer for each transistor. A portion of insulating layer 213 serves as the gate insulating layer for each transistor. Insulating layer 215 is disposed to cover the transistor. Insulating layer 214 is disposed to cover the transistor and serves as a planarization layer. Furthermore, there is no particular limitation on the number of gate insulating layers and the number of insulating layers covering the transistor; there can be one or more.

[0310] Inorganic insulating films are preferably used as insulating layers 211, 213 and 215.

[0311] The insulating layer 214 used as the planarization layer is preferably an organic insulating layer.

[0312] Transistor 201 and transistor 205 include: a conductive layer 221 serving as a gate; an insulating layer 211 serving as a gate insulating layer; conductive layers 222a and 222b serving as source and drain; a semiconductor layer 231; an insulating layer 213 serving as a gate insulating layer; and a conductive layer 223 serving as a gate.

[0313] A connection portion 204 is provided in a region of substrate 351 that is not overlapped with substrate 352. In the connection portion 204, wiring 355 is electrically connected to FPC 353 via conductive layer 166 and connection layer 242. An example is shown where conductive layer 166 has a stacked structure comprising a conductive film formed by processing conductive films identical to conductive layers 224R, 224G, and 224B; a conductive film formed by processing conductive films identical to conductive layers 151R, 151G, and 151B; and a conductive film formed by processing conductive films identical to conductive layers 152R, 152G, and 152B. Conductive layer 166 is exposed on the top surface of connection portion 204. Therefore, connection portion 204 can be electrically connected to FPC 353 via connection layer 242.

[0314] Preferably, a light-shielding layer 157 is provided on the surface of the substrate 352 on the substrate 351 side. The light-shielding layer 157 can be provided between adjacent light-emitting devices, in the connection portion 140, and in the circuit 356, etc. In addition, various optical components can be arranged on the outer side of the substrate 352.

[0315] Substrate 351 and substrate 352 may each be made of a material that can be used in substrate 120.

[0316] As the adhesive layer 142, a material suitable for the resin layer 122 can be used.

[0317] As the connecting layer 242, anisotropic conductive film (ACF) or anisotropic conductive paste (ACP) can be used.

[0318] [Display Device 100D] Figure 7 The display device 100D shown is Figure 6 The main difference between the display device 100C and the display device 100D is that the display device 100D is a bottom-emitting type display device.

[0319] The light emitted by the light-emitting device is directed onto one side of the substrate 351. The substrate 351 is preferably made of a material with high transmittance to visible light. On the other hand, there are no restrictions on the transmittance of the material used for the substrate 352.

[0320] Preferably, a light-shielding layer is formed between the substrate 351 and the transistor 201 and between the substrate 351 and the transistor 205. Figure 7 An example is shown where a light-shielding layer 157 is disposed on a substrate 351, an insulating layer 153 is disposed on the light-shielding layer 157, and transistors 201, 205, etc. are disposed on the insulating layer 153.

[0321] The light-emitting device 130R includes a conductive layer 112R, a conductive layer 126R on the conductive layer 112R, and a conductive layer 129R on the conductive layer 126R.

[0322] The light-emitting device 130B includes a conductive layer 112B, a conductive layer 126B on the conductive layer 112B, and a conductive layer 129B on the conductive layer 126B.

[0323] The conductive layers 112R, 112B, 126R, 126B, 129R, and 129B all use materials with high transmittance to visible light. A material that reflects visible light is preferably used as the second electrode.

[0324] Note that, although Figure 7 The light-emitting device 130G is not shown in the figure, but it is also provided.

[0325] in addition, Figure 7 Examples are shown where the top surface of layer 128 has a flat portion, but there are no particular restrictions on the shape of layer 128.

[0326] [Display Device 100E] Figure 8 The display device 100E shown is Figure 6 The main difference between the display device 100E and the display device 100C is that the display device 100E includes color layer 132R, color layer 132G and color layer 132B.

[0327] In the display device 100E, the light-emitting device 130 has a region overlapping one of the coloring layers 132R, 132G, and 132B. The coloring layers 132R, 132G, and 132B can be disposed on a surface of the substrate 352 on one side of the substrate 351. The ends of the coloring layers 132R, 132G, and 132B can overlap the light-shielding layer 157.

[0328] In the display device 100E, the light-emitting device 130 can emit white light, for example. Additionally, for example, the color layers 132R, 132G, and 132B can transmit red light, green light, and blue light, respectively. Alternatively, the display device 100E may also employ a structure in which the color layers 132R, 132G, and 132B are disposed between the protective layer 131 and the adhesive layer 142.

[0329] Figure 6 and Figure 8 Examples are shown where the top surface of layer 128 has a flat portion, but there are no particular restrictions on the shape of layer 128.

[0330] This embodiment can be appropriately combined with other embodiments or examples. Furthermore, where multiple structural examples are shown in one embodiment in this specification, these structural examples can be appropriately combined.

[0331] Implementation Method 5 In this embodiment, an electronic device according to one aspect of the present invention will be described.

[0332] The electronic device of this embodiment includes a display device according to one aspect of the present invention in its display unit. The display device according to one aspect of the present invention has low power consumption. Therefore, it can be used in the display units of various electronic devices.

[0333] As electronic devices, in addition to large-screen electronic devices such as television sets, desktop or laptop personal computers, monitors for computers, digital signage, and large game machines such as pinball machines, other examples include digital cameras, digital video cameras, digital photo frames, mobile phones, portable game consoles, portable information terminals, and sound reproduction devices.

[0334] In particular, because the display device of one aspect of the present invention has low power consumption, it can be suitable for use in smaller electronic devices. Examples of such electronic devices include watch-type and bracelet-type information terminal devices (wearable devices), wearable devices that can be worn on the head, VR devices such as head-mounted displays, AR devices such as glasses, and MR devices.

[0335] The electronic device in this embodiment may also include a sensor (which has the function of measuring factors such as force, displacement, position, velocity, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, tilt, vibration, odor, or infrared radiation).

[0336] Reference Figures 9A to 9D This illustrates an example of a wearable device that can be worn on the head.

[0337] Figure 9A The electronic device 700A shown and Figure 9B The electronic devices 700B shown include a pair of display panels 751, a pair of housings 721, a communication unit (not shown), a pair of mounting units 723, a control unit (not shown), an imaging unit (not shown), a pair of optical components 753, a frame 757, and a pair of nose pads 758.

[0338] The display panel 751 can be used in a display device according to one aspect of the present invention. Thus, an electronic device with low power consumption and the ability to operate for extended periods can be realized.

[0339] Both electronic devices 700A and 700B can project the image displayed by the display panel 751 onto the display area 756 in the optical component 753. Because the optical component 753 is light-transmitting, the user can see the image displayed in the display area by overlapping the image seen through the optical component 753.

[0340] Both electronic devices 700A and 700B can be equipped with cameras capable of capturing images of the front as imaging units. Furthermore, by incorporating accelerometers such as gyroscopes into both electronic devices 700A and 700B, the orientation of the user's head can be detected, and an image corresponding to that orientation can be displayed on the display area 756.

[0341] The communications unit includes a wireless communication device through which video signals can be supplied, for example. Additionally, a connector capable of connecting cables supplying video signals and power potential may be included, either in place of the wireless communication device or in addition to the wireless communication device.

[0342] In addition, electronic devices 700A and 700B are equipped with batteries that can be charged wirelessly or via wired means, or both.

[0343] The housing 721 can also be equipped with a touch sensor module.

[0344] Various touch sensors can be used as touch sensor modules. For example, capacitive, resistive, infrared, electromagnetic induction, surface acoustic wave, and optical sensors can be employed. In particular, capacitive or optical sensors are preferred for use in touch sensor modules.

[0345] Figure 9C The electronic device 800A shown and Figure 9D The electronic devices 800B shown all include a pair of display units 820, a housing 821, a communication unit 822, a pair of mounting units 823, a control unit 824, a pair of imaging units 825, and a pair of lenses 832.

[0346] The display unit 820 can be equipped with a display device according to one aspect of the present invention. This allows for the realization of an electronic device with low power consumption and the ability to operate for extended periods.

[0347] The display unit 820 is located inside the housing 821 in a position visible through the lens 832. Furthermore, by displaying different images on each of the pair of display units 820, three-dimensional display utilizing parallax can be achieved.

[0348] Electronic devices 800A and 800B preferably have a mechanism in which the left and right positions of the lens 832 and the display unit 820 can be adjusted so that the lens 832 and the display unit 820 are in the most suitable position according to the position of the user's eyes.

[0349] Users can use the mounting unit 823 to wear electronic device 800A or electronic device 800B on their heads.

[0350] The imaging unit 825 has the function of acquiring external information. The data acquired by the imaging unit 825 can be output to the display unit 820. An image sensor can be used in the imaging unit 825. In addition, multiple cameras can be set to support various viewing angles such as telephoto and wide-angle.

[0351] Electronic device 800A may also include a vibration mechanism used as a bone conduction headphone.

[0352] Electronic devices 800A and 800B may also include input terminals. Cables supplying image signals from image output devices and the like, as well as power for charging batteries installed within the electronic devices, can be connected to the input terminals.

[0353] The electronic device of one embodiment of the present invention may also have the function of wireless communication with the earphone 750.

[0354] In addition, electronic devices may also include an earphone unit. Figure 9B The illustrated electronic device 700B includes an earphone unit 727. A portion of the wiring connecting the earphone unit 727 and the control unit may also be configured inside the housing 721 or the mounting unit 723.

[0355] Similarly, Figure 9D The illustrated electronic device 800B includes an earphone unit 827. For example, a structure in which the earphone unit 827 and the control unit 824 are connected in a wired manner can be adopted.

[0356] Thus, as an embodiment of the present invention, both eyeglass type (electronic device 700A and electronic device 700B, etc.) and goggle type (electronic device 800A and electronic device 800B, etc.) are preferred electronic devices.

[0357] Figure 10A The electronic device 6500 shown is a portable information terminal device that can be used as a smartphone.

[0358] Electronic device 6500 includes a housing 6501, a display unit 6502, a power button 6503, a button 6504, a speaker 6505, a microphone 6506, a camera 6507, and a light source 6508, etc. The display unit 6502 has a touch panel function.

[0359] The display unit 6502 can use a display device according to one aspect of the present invention. This allows for the realization of an electronic device with low power consumption and the ability to operate for extended periods.

[0360] Figure 10B This is a cross-sectional schematic diagram of one end of the microphone 6506, including the housing 6501.

[0361] A light-transmitting protective member 6510 is provided on one side of the display surface of the housing 6501. The space surrounded by the housing 6501 and the protective member 6510 contains a display panel 6511, an optical member 6512, a touch sensor panel 6513, a printed circuit board 6517, a battery 6518, etc.

[0362] The display panel 6511, optical component 6512, and touch sensor panel 6513 are fixed to the protective component 6510 using an adhesive layer (not shown).

[0363] In the area outside the display unit 6502, a portion of the display panel 6511 is folded back, and this folded portion is connected to an FPC 6515. An IC 6516 is mounted on the FPC 6515. The FPC 6515 is connected to terminals disposed on a printed circuit board 6517.

[0364] The display panel 6511 can be used with a display device according to one aspect of the present invention. This allows for the realization of an extremely lightweight electronic device. Furthermore, since the display panel 6511 is extremely thin, a large-capacity battery 6518 can be installed while minimizing the thickness of the electronic device. Additionally, by folding a portion of the display panel 6511 to provide a connection portion with the FPC 6515 on the back of the pixel section, a narrow-bezel electronic device can be achieved.

[0365] Figure 10C An example of a television device is shown. In the television device 7100, a display unit 7000 is assembled in a housing 7171. Here is shown a structure in which the housing 7171 is supported by a bracket 7173.

[0366] The display unit 7000 can use a display device according to one aspect of the present invention. This allows for the realization of an electronic device with low power consumption and the ability to operate for extended periods.

[0367] It can be operated using the operating switch included in the housing 7171 and the separately provided remote control 7151. Figure 10C The operation of the television device 7100 shown.

[0368] Figure 10DAn example of a notebook computer is shown. The notebook computer 7200 includes a casing 7211, a keyboard 7212, a pointing device 7213, and an external connection port 7214, etc. A display unit 7000 is assembled in the casing 7211.

[0369] The display unit 7000 can use a display device according to one aspect of the present invention. This allows for the realization of an electronic device with low power consumption and the ability to operate for extended periods.

[0370] Figure 10E and Figure 10F Here is an example of digital signage.

[0371] Figure 10E The digital sign 7300 shown includes a housing 7301, a display unit 7000, and a speaker 7303. It may also include LEDs, operation keys (including a power switch or operation switch), connection terminals, various sensors, a microphone, etc.

[0372] Figure 10F A digital sign 7400 is shown mounted on a cylindrical column 7401. The digital sign 7400 includes a display section 7000 disposed along the curved surface of the column 7401.

[0373] exist Figure 10E and Figure 10F In this embodiment, a display device according to one aspect of the present invention can be used in the display unit 7000. This allows for the realization of a highly reliable electronic device.

[0374] The larger the display unit (7000), the more information it can provide at once. A larger display unit (7000) is also more likely to attract attention, which can improve the effectiveness of advertising.

[0375] like Figure 10E and Figure 10F As shown, the digital signage 7300 or digital signage 7400 preferably can be linked with the user's smartphone or other information terminal device 7311 or information terminal device 7411 via wireless communication.

[0376] Figures 11A to 11G The electronic device shown includes a housing 9000, a display unit 9001, a speaker 9003, operation keys 9005 (including a power switch or operation switch), a connection terminal 9006, a sensor 9007 (which has the function of measuring the following factors: force, displacement, position, velocity, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, tilt, vibration, odor, or infrared radiation), a microphone 9008, etc.

[0377] Figures 11A to 11GThe electronic device shown has various functions. For example, it may have the following functions: displaying various information (static images, dynamic images, or text images, etc.) on the display unit; touch panel function; displaying calendar, date, or time, etc.; controlled and processed by various software (programs); wireless communication function; reading and processing programs or data stored in the storage medium; etc.

[0378] The following is a detailed explanation. Figures 11A to 11G The electronic device shown.

[0379] Figure 11A This is a perspective view showing a portable information terminal 9171. The portable information terminal 9171 can be used, for example, as a smartphone. Note that a speaker 9003, a connection terminal 9006, a sensor 9007, etc., may also be included in the portable information terminal 9171. Furthermore, as a portable information terminal 9171, text or image information can be displayed on multiple surfaces. Figure 11A The image shows an example displaying three icons 9050. Alternatively, information 9051, shown as a dashed rectangle, can be displayed on other surfaces of the display unit 9001. Examples of information 9051 include notifications of received emails, SNS messages, or phone calls; the subject of the email or SNS message; the sender's name; the date; the time; remaining battery level; and radio wave strength. Alternatively, icons 9050 can be displayed in the same location where information 9051 is displayed.

[0380] Figure 11B This is a perspective view showing a portable information terminal 9172. The portable information terminal 9172 has the function of displaying information on three or more surfaces of the display unit 9001. Here, examples are shown where information 9052, information 9053, and information 9054 are displayed on different surfaces. For example, when the portable information terminal 9172 is placed in a jacket pocket, the user can view information 9053 displayed in a position seen from above the portable information terminal 9172.

[0381] Figure 11C This is a perspective view of a tablet terminal 9173. The tablet terminal 9173 can, for example, execute various application software such as mobile phone, email, and article reading and editing, music playback, network communication, and computer games. The tablet terminal 9173 includes a display unit 9001, a camera 9002, a microphone 9008, and a speaker 9003 on the front of its casing 9000; operation keys 9005 serving as operating buttons on the left side of the casing 9000; and a connection terminal 9006 on the bottom surface.

[0382] Figure 11DThis is a perspective view showing a watch-type portable information terminal 9200. The portable information terminal 9200 can be used, for example, as a smartwatch (registered trademark). Furthermore, the display surface of the display unit 9001 is curved, allowing display along its curved surface. In addition, the portable information terminal 9200 can perform hands-free calls, for example, by communicating with a headset capable of wireless communication. Furthermore, by utilizing the connection terminal 9006, the portable information terminal 9200 can transmit data or charge with other information terminals. Charging can also be performed wirelessly.

[0383] Figures 11E to 11G This is a perspective view showing the foldable portable information terminal 9201. Additionally, Figure 11E This is a 3D view of the portable information terminal 9201 in its unfolded state. Figure 11G It is a 3D image of the folded state. Figure 11F From Figure 11E status and Figure 11G The portable information terminal 9201 is a three-dimensional representation of the state transitioning between different states. In its folded state, it offers good portability, while in its unfolded state, it provides a large, seamless display area, resulting in excellent browsing capabilities. The display unit 9001 included in the portable information terminal 9201 is supported by three housings 9000 connected by hinges 9055. The display unit 9001 can be bent, for example, within a radius of curvature of 0.1 mm or more and 150 mm or less.

[0384] This embodiment can be appropriately combined with other embodiments or examples. Furthermore, where multiple structural examples are shown in one embodiment in this specification, these structural examples can be appropriately combined. Example 1

[0385] <<Synthesis Example 1>> In this synthetic example, the method for synthesizing 4-chloro-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviated as: 4Cl7HidPhen), the organic compound of the present invention represented by structural formula (259) in Embodiment 1, is described. The structure of 4Cl7HidPhen is shown below.

[0386] [Chemical Formula 36]

[0387] 2.9 g (12 mmol) of 4,7-dichloro-1,10-phenanthroline, 2.8 mL (24 mmol) of 2,3,3a,4,5,6,7,7a-octahydro-1H-isoindole, 4.9 g (35 mmol) of potassium carbonate (K₂CO₃), and 24 mL of N-methylpyrrolidone (NMP) were placed in a 100 mL three-necked flask and stirred at 80 °C for 5 hours. After cooling to room temperature, 50 mL of water and 50 mL of chloroform were added to the flask, and the mixture was separated using a separatory funnel. The mixture was extracted three times with chloroform, and the resulting organic layer was washed once with pure water. The organic layer was gravity filtered, and the filtrate was concentrated to obtain a solid. A small amount of acetone was added to the solid to obtain a suspension of the target compound. The suspension was filtered to obtain 3.6 g (92% yield) of a pale yellow solid of the target compound. The synthetic scheme (s1-1) is shown below.

[0388] [Chemical Formula 37]

[0389] Figures 12A to 12C The resulting pale yellow solid is shown. 1 The results of H NMR measurements. Figure 12B It is magnification Figure 12A The graph shows the range of 6.5 ppm to 9.0 ppm. Figure 12C This is a graph shown magnified to the range of 1 ppm to 4.0 ppm. Additionally, the following shows... 1 The results of H NMR measurements.

[0390] 1 H NMR (CD2Cl2, 500MHz): δ=8.89 (1H, d, J=5.0Hz), 8.64 (1H, d, J=5.5Hz), 8.35 (1H, d, J=10Hz), 7.95 (1H, d, J=10 Hz), 7.63 (1H, d, J = 4.5Hz), 6.73 (1H, d, J = 5.0Hz), 3.75-.3.60 (4H, m), 2.41-2.34 (2H, m), 1.70-1.38 (8H, m).

[0391] In addition, the molecular weight of the obtained pale yellow solid was measured using liquid chromatography-mass spectrometry (LC / MS).

[0392] In LC / MS analysis, LC (high-performance liquid chromatography) separation was performed using an AcquityUPLC system manufactured by Waters Corporation, and MS (mass spectrometry) analysis was performed using a Xevo G2 TofMS system manufactured by Waters Corporation. The chromatographic column used for LC separation was an AcquityUPLC BEH C8 (2.1 × 100 mm, 1.7 μm), and the column temperature was 40 °C. Acetonitrile was used as mobile phase A, and 0.1% formic acid aqueous solution was used as mobile phase B. Additionally, in the sample preparation, 2.0 mg of 4Cl7HidPhen was added to a sample vial, and 1.0 mL of dichloromethane was added using a micropipette to dissolve it, yielding a 1.0 mL solution. Then, 9.0 mL of acetonitrile was added to this solution using a micropipette, adjusting the concentration of 4Cl7HidPhen to 200 ppm. The sample injection volume was 5.0 μL.

[0393] In LC separation, a gradient method was used to change the composition of the mobile phase. The ratio was set to mobile phase A:mobile phase B = 30:70 from 0 to 1 minute after the start of measurement. Then, the composition was changed, and the ratio was set to mobile phase A:mobile phase B = 95:5 10 minutes after the start of measurement. The composition was changed linearly.

[0394] In MS analysis, ionization was performed using electrospray ionization (ESI) with a capillary voltage of 3.01075 kV and a sample cone voltage of 30 V, detected in positive mode. The measured mass range was m / z = 100 to 1200.

[0395] Based on the LC / MS analysis, a peak representing m / z 338 was observed relative to the calculated mass 337 of 4Cl7HidPhen. This peak can be considered to be a proton adduct of 4Cl7HidPhen.

[0396] Depend on 1 The results of H NMR and LC / MS analysis show that 4Cl7HidPhen was obtained in this synthesis example.

[0397] Here, the synthesis method disclosed in Non-Patent Document 1 is used to illustrate the results of the same synthesis as in the examples. Diisopropylethylamine is used as the base in the synthesis method disclosed in Non-Patent Document 1.

[0398] 1.0 g (4.0 mmol) of 4,7-dichloro-1,10-phenanthroline, 1.0 g (8.1 mmol) of 2,3,3a,4,5,6,7,7a-octahydro-1H-isoindole, 1.6 g (12 mmol) of diisopropylethylamine, and 8 mL of N-methylpyrrolidone (NMP) were placed in a standard glass reaction vessel with a diameter of 24 mm and stirred at 80 °C for 5 hours. After cooling to room temperature, the solid precipitated in the reaction vessel was filtered to obtain 0.13 g of a yellow solid. The synthetic scheme (s1-2) of this synthetic example is shown below.

[0399] [Chemical Formula 38]

[0400] Figures 13A to 13C The obtained yellow solid is shown. 1 1H NMR measurement results. Figure 13B It is magnification Figure 13A The graph shows the range of 6.5 ppm to 9.0 ppm. Figure 13C This is a graph shown magnified to the range of 1 ppm to 4.0 ppm. Additionally, the following shows... 1 The results of H NMR measurements.

[0401] 1 H NMR (CD2Cl2, 500MHz): δ=8.58 (2H, d, J=5.5Hz), 7.98 (2H, s), 6.65 (2H, d, J=5.0), 3.80-3.60 (8H, m), 2.45-2.30 (4H, m), 1.85-1.35 (16H, m).

[0402] The obtained yellow solid was analyzed by LC / MS, and its mass was measured. The results showed that a peak with m / z 427 was predominantly observed in the chromatogram. m / z 427 can be considered to be the peak of the following proton-added compound: 4,7-di(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviated: Hid2Phen) (calculated mass: 426), an organic compound of two 2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl groups bonded to 1,10-phenanthroline.

[0403] Depend on 1The results of 1H NMR and LC / MS analyses show that Hid2Phen was obtained by the synthetic method disclosed in Non-Patent Document 1. This synthetic method can selectively provide only 4,7-bis(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviated as Hid2Phen). In cases where symmetrical compounds with two or more functional groups exhibit essentially the same reactivity or reaction selectivity, it is currently difficult to selectively make only one of them react. Generally, as a method to improve reaction selectivity in coupling reactions, etc., although sometimes the ligand of the transition metal catalyst is adjusted to obtain selectivity, examples of controlling reactivity using simple and classical nucleophilic substitution reactions as in this method are extremely rare. Therefore, this invention provides an excellent method for asymmetrically modifying the symmetrical functional groups of a compound.

[0404] As can be seen from the above results, when using diisopropylethylamine in the synthesis method disclosed in Non-Patent Document 1, almost no 4Cl7HidPhen of the target compound was obtained. Thus, it is difficult to synthesize asymmetric 1,10-phenanthroline derivatives simply by using different types of bases. Therefore, the synthesis method of one aspect of the present invention is a very useful synthetic method for obtaining asymmetric 1,10-phenanthroline derivatives. Example 2

[0405] <<Synthesis Example 2>> In this embodiment, the synthesis method of 4-chloro-7-(1-pyrrolidinyl)-1,10-phenanthroline (abbreviated as 4Cl7PrdPhen), represented by structural formula (200) in Embodiment 1, is described. The structure of 4Cl7PrdPhen is shown below.

[0406] [Chemical Formula 39]

[0407] 30 g (0.12 mol) of 4,7-dichloro-1,10-phenanthroline, 8.5 g (0.12 mol) of 1H-pyrrolidine, 50 g (0.36 mol) of potassium carbonate, and 0.24 L of 1-methyl-2-pyrrolidone (NMP) were placed in a 1000 mL three-necked flask and stirred at 100 °C for 5 hours under a nitrogen stream. After stirring, the mixture was cooled to room temperature. The insoluble matter of the mixture was separated by vacuum filtration, and the resulting filtrate was extracted with dichloromethane. The extract was concentrated to obtain an oil. Hexane was added to the oil and stirred at 0 °C. The precipitated solid was collected by vacuum filtration. Ethyl acetate and hexane were added to the solid and the mixture was sonicated. The solid was collected by vacuum filtration, yielding a light brown solid (19 g, yield 56%) of the target compound. The following formula (s2-1) shows the synthetic scheme of this example.

[0408] [Chemical Formula 40]

[0409] Figures 14A to 14C The resulting light brown solid is shown. 1 H NMR spectrum. Figure 14B It is magnification Figure 14A The graph shows the range of 6.5 ppm to 9.5 ppm. Figure 14C This is a graph shown magnified to the range of 1 ppm to 4.0 ppm. Additionally, the following shows... 1 The H NMR measurement results confirmed the presence of 4Cl7PrdPhen.

[0410] 1 H NMR (CDCl3, 300MHz): δ=8.99 (1H, d, J=4.8Hz), 8.77 (1H, d, J=5.5Hz), 8.29 (1H, d, J=9.5Hz), 7.97 (1 H, d, J = 9.5Hz), 7.65 (1H, d, J = 4.8Hz), 6.77 (1H, d, J = 5.5Hz), 3.73-3.69 (4H, m), 2.10-2.05 (4H, m).

[0411] Thus, it can be seen that one aspect of the synthesis method of the present invention is a method that does not lose selectivity even when the synthesis scale is increased. Example 3

[0412] <<Synthesis Example 3>> In this embodiment, the synthesis method of 4-bromo-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviated as 4Br7HidPhen), represented by structural formula (202) in Embodiment 1, is described. The structure of 4Br7HidPhen is shown below.

[0413] [Chemical Formula 41]

[0414] 10 g (30 mmol) of 4,7-dibromo-1,10-phenanthroline, 3.7 g (30 mmol) of 2,3,3a,4,5,6,7,7a-octahydro-1H-isoindole, 12 g (87 mmol) of potassium carbonate, and 0.10 L of 1-methyl-2-pyrrolidone (NMP) were placed in a 1000 mL three-necked flask and stirred at 100 °C for 7 hours under a nitrogen atmosphere. After stirring, the mixture was cooled to room temperature. The insoluble matter in the mixture was separated by filtration, and the filtrate was extracted with dichloromethane. The extract was concentrated to obtain an oil. The oil was purified by silica gel column chromatography (developing solvents: ethyl acetate, chloroform, methanol). The resulting fraction was concentrated to obtain an oil. A small amount of chloroform and ethyl acetate were added to the oil, and the mixture was irradiated with ultrasound. The precipitated solid was collected by filtration to obtain a yellow solid of the target compound (7.6 g, yield 69%). The following equation (s3-1) shows the synthesis scheme for this synthesis example.

[0415] [Chemical Formula 42]

[0416] Figures 15A to 15C The obtained yellow solid is shown. 1 H NMR spectrum. Figure 15B It is magnification Figure 15A The graph shows the range of 6.5 ppm to 9.0 ppm. Figure 15C This is a graph shown magnified to the range of 1 ppm to 4.0 ppm. Additionally, the following shows... 1 The H NMR measurement results confirmed the presence of 4Br7HidPhen.

[0417] 1H NMR (CDCl3, 300MHz): δ=8.88 (1H, d, J=4.8Hz), 8.76 (1H, d, J=5.9Hz), 8.32 (1H, d, J=9.5Hz), 7.93 (1H, d, J= 9.5Hz), 7.84 (1H, d, J = 4.8Hz), 6.73 (1H, d, J = 5.9Hz), 3.77-3.62 (4H, m), 2.40 (2H, br), 1.62-1.45 (8H, m). Example 4

[0418] <<Synthesis Example 4>> In this embodiment, the synthesis method of 4-bromo-7-(1-pyrrolidinyl)-1,10-phenanthroline (abbreviated as 4Br7PrdPhen), represented by structural formula (201) in Embodiment 1, is described. The structure of 4Br7PrdPhen is shown below.

[0419] [Chemical Formula 43]

[0420] 1.5 g (4.4 mmol) of 4,7-dibromo-1,10-phenanthroline, 0.32 g (4.5 mmol) of 1H-pyrrolidine, 1.8 g (13 mmol) of potassium carbonate, and 10 mL of 1-methyl-2-pyrrolidone (NMP) were placed in a 50 mL three-necked flask and stirred at 100 °C for 7 hours under a nitrogen atmosphere. After stirring, the mixture was cooled to room temperature. The insoluble matter in the mixture was separated by filtration, and the filtrate was extracted with dichloromethane after adding water. The extract was concentrated to obtain an oil. The oil was purified by silica gel column chromatography (developing solvents: ethyl acetate, chloroform, methanol, in sequence). The resulting fraction was concentrated to obtain an oil. A small amount of chloroform and ethyl acetate were added to the oil and the mixture was irradiated with ultrasound. The precipitated solid was collected by filtration to obtain a yellow solid of the target compound (0.77 g, yield 51%). The following formula (s4-1) shows the synthetic scheme of this example.

[0421] [Chemical Formula 44]

[0422] Figures 16A to 16C The obtained yellow solid is shown. 1 H NMR spectrum. Figure 16B It is magnification Figure 16A The graph shows the range of 6.5 ppm to 9.0 ppm. Figure 16C This is a graph shown magnified to the range of 1 ppm to 4.0 ppm. Additionally, the following shows... 1The H NMR measurement results confirmed the presence of 4Br7PrdPhen.

[0423] 1 H NMR (CDCl3, 300MHz): δ=8.88 (1H, d, J=4.8Hz), 8.78 (1H, d, J=5.5Hz), 8.30 (1H, d, J=9.5Hz), 7.94 (1 H, d, J = 9.5Hz), 7.85 (1H, d, J = 4.8Hz), 6.77 (1H, d, J = 5.9Hz), 3.74-3.70 (4H, m), 2.11-2.07 (4H, m). Example 5

[0424] <<Synthesis Example 5>> In this synthetic example, the method for synthesizing 2-chloro-9-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviated as: 2Cl9HidPhen), the organic compound of the present invention represented by structural formula (203) in Embodiment 1, is described. The structure of 2Cl9HidPhen is shown below.

[0425] [Chemical Formula 45]

[0426] 1.0 g (4.0 mmol) of 2,9-dichloro-1,10-phenanthroline, 1.1 mL (8.4 mmol) of 2,3,3a,4,5,6,7,7a-octahydro-1H-isoindole, 1.7 g (12 mmol) of potassium carbonate (K₂CO₃), and 8 mL of N-methylpyrrolidone (NMP) were placed in a 24 mm diameter standard glass reaction vessel and stirred at 80 °C for 4 hours. After cooling to room temperature, water was added, and the mixture was extracted with chloroform. The extract was washed once with saturated brine. After separation, the organic layer was gravity filtered, and the filtrate was concentrated, precipitating a yellow solid. Filtering yielded 1.3 g of a yellow solid containing the target compound. The solid was purified by silica gel column chromatography (developing solvent: chloroform) to obtain the target compound (0.67 g, 50% yield). The synthetic scheme of this example is shown below (s5-1).

[0427] [Chemical Formula 46]

[0428] Figures 17A to 17C The obtained yellow solid is shown. 1 1H NMR measurement results. Figure 17B It is magnification Figure 17AThe graph shows the range of 6.5 ppm to 8.5 ppm. Figure 17C This is a graph shown magnified to the range of 1 ppm to 4.0 ppm. Additionally, the following shows... 1 The results of H NMR measurements.

[0429] 1 H NMR (CD2Cl2, 500MHz): δ=8.11 (1H, d, J=8.5Hz), 7.94 (1H, d, J=9.5Hz), 7.64 (1H, d, J=8.5Hz), 7.47 (1H, d, J=8.0 Hz), 7.42 (1H, d, J = 8.5Hz), 6.75 (1H, d, J = 9.0Hz), 4.20-3.00 (8H, br), 2.50-2.35 (4H, br), 1.76-1.35 (16H, m).

[0430] The molecular weight of the obtained yellow solid was measured using LC / MS analysis. The results showed a peak representing m / z 338 relative to the calculated mass of the target compound (337). This can be considered a peak of the proton-added component of 2Cl9HidPhen.

[0431] according to 1 The results of H NMR and LC / MS analysis show that 2Cl9HidPhen can be obtained through this synthesis example. Example 6

[0432] <<Synthesis Example 6>> In this synthetic example, the method for synthesizing 4-chloro-4'-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-2,2'-bipyridine (abbreviated as: 4Cl4'HidBpy), the organic compound of the present invention represented by structural formula (204) in Embodiment 1, is described. The structure of 4Cl4'HidBpy is shown below.

[0433] [Chemical Formula 47]

[0434] 1.0 g (4.4 mmol) of 4,4'-dichloro-2,2'-bipyridine, 1.1 mL (9.0 mmol) of 2,3,3a,4,5,6,7,7a-octahydro-1H-isoindole, 1.8 g (13 mmol) of potassium carbonate (K₂CO₃), and 9 mL of N-methylpyrrolidone (NMP) were placed in a standard glass reaction vessel with a diameter of 24 mm and stirred at 80 °C for 6 hours. After cooling to room temperature, water was added, and the mixture was extracted with chloroform. The resulting extract was gravity filtered, and the filtrate was concentrated to obtain an oil. The oil was purified by silica gel column chromatography (developing solvents: ethyl acetate, chloroform, ethanol). The resulting fraction was concentrated to obtain an oil. A small amount of chloroform and hexane were added to the oil, and the mixture was irradiated with ultrasound. The precipitated solid was collected by vacuum filtration, yielding a white solid of the target compound (0.45 g, yield 32%). The following shows the synthesis scheme (s6-1) for this synthesis example.

[0435] [Chemical Formula 48]

[0436] Figures 18A to 18C The obtained white solid is shown 1 1H NMR measurement results. Figure 18B It is magnification Figure 18A The graph shows the range of 6.0 ppm to 9.0 ppm. Figure 18C This is a graph shown magnified to the range of 1 ppm to 4.0 ppm. Additionally, the following shows... 1 The results of H NMR measurements.

[0437] 1 H NMR (CD2Cl2, 500MHz): δ=8.49 (1H, d, J=5.0Hz), 8.43 (1H, d, J=2.5Hz), 8.20 (1H, d, J=5.0Hz), 7.52 (1H, d, J=2.0Hz) , 7.27 (1H, dd, J = 5.3Hz, 2.0Hz), 6.39 (1H, dd, J = 6.0Hz, 3.0Hz), 3.46-3.20 (4H, m), 2.35 (2H, m), 1.70-1.34 (8H, m).

[0438] The molecular weight of the obtained white solid was measured using LC / MS analysis. The results showed a peak representing m / z 314 relative to the calculated mass of the target compound (313). This can be considered a peak of the proton-dependent adduct of 4Cl4'HidBpy.

[0439] according to 1The results of H NMR and LC / MS analysis show that 4Cl4'HidBpy was obtained. Example 7

[0440] <<Synthesis Example 7>> In this embodiment, the synthesis method of 4-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-7-(3,4-diphenyl-1-pyrrolyl)-1,10-phenanthroline (abbreviated as: Hid-DPPrdPhen), represented by structural formula (100) in Embodiment 1, is described. The structure of Hid-DPPrdPhen is shown below.

[0441] [Chemical Formula 49]

[0442] 2.8 g (8.3 mmol) of 4-chloro-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline, 2.0 g (9.0 mmol) of rac-trans-3,4-diphenylpyrrolidine, and 3.7 g (24 mmol) of diazabicycloundecene (DBU) were placed in a 50 mL three-necked flask and stirred at 100 °C for 8 hours under a nitrogen atmosphere. After stirring, the mixture was cooled to room temperature. Water was added to the mixture, and the mixture was extracted with chloroform. The extract was concentrated to give an oil. Ethyl acetate and hexane were added to the oil, and the mixture was sonicated. The solid was collected by vacuum filtration to give a light brown solid (2.5 g, yield 58%) of the target compound. The following formula (s7-1) shows the synthetic scheme of this example.

[0443] [Chemical Formula 50]

[0444] 1.3 g of the obtained light brown solid (2.5 g) was purified by sublimation using a gradient sublimation method. The sublimation was performed at an argon flow rate of 0 mL / min and a pressure of 2.8 × 10⁻⁶. -2 The sample was sublimated by heating at 255°C for 24 hours. The result was a yellow solid (0.53 g, recovery rate 41%).

[0445] Figures 19A to 19C The obtained yellow solid is shown. 1 H NMR spectrum. Figure 19B It is magnification Figure 19A The graph shows the range of 6.5 ppm to 9.0 ppm. Figure 19C This is a graph shown magnified to the range of 1 ppm to 4.0 ppm. Additionally, the following shows... 1Measurement results of \(^1H\) NMR. From these results, it was confirmed that Hid-DPPrdPhen could be obtained through this synthesis example.

[0446] 1 \(^1H\) NMR (CD₂Cl₂, 300 MHz): δ = 8.68 (1H, d, J = 5.1 Hz), 8.62 (1H, d, J = 5.5 Hz), 8.02 - 7.92 (2H, m), 7.33 - 7.21 (10H, m), 6.77 (1H, d, J = 5.1 Hz), 6.68 (1H, d, J = 5.5 Hz), 4.17 - 4.02 (4H, m), 3.83 - 3.71 (4H, m), 3.63 - 3.57 (1H, m), 3.52 - 3.47 (1H, m), 2.44 - 2.37 (1H, m), 2.33 - 2.27 (1H, m), 1.63 - 1.32 (8H, m).

[0447] The glass transition temperature (Tg) of Hid-DPPrdPhen was measured. Using a differential scanning calorimeter (DSC8500 manufactured by PerkinElmer Japan Co., Ltd.), the powder was placed on an aluminum cell and heated at a rate of 40 °C / min to measure Tg. From these results, it was found that the Tg of Hid-DPPrdPhen was 129 °C, indicating good heat resistance.

[0448] Next, a solubility test of Hid-DPPrdPhen was conducted. Note that this test was carried out at one atmosphere and room temperature (RT).

[0449] <Solubility test of Hid-DPPrdPhen using LC / MS analysis> In LC / MS analysis, LC (liquid chromatography) separation was performed using Acquity UPLC manufactured by Waters Corporation, and MS analysis (mass spectrometry) was carried out using Xevo G2 TofMS manufactured by Waters Corporation. The chromatographic column used in LC separation was Acquity UPLC BEH C8 (2.1 × 100 mm, 1.7 μm). Acetonitrile was used as mobile phase A, and a 0.1% aqueous formic acid solution was used as mobile phase B. In addition, the sample injection volume was 5.0 μL. Note that the wavelength of the photodiode array detector was set at 254 nm ± 1 nm for analysis.

[0450] 1 mg of Hid-DPPrdPhen was placed in a 5 mL sample vial, 1 mL of water was added, and ultrasonic irradiation was performed for 5 minutes. The mixture was filtered using a membrane filter to remove solids, and the resulting filtrate was diluted 5-fold with acetonitrile. The obtained solution was subjected to LC / MS analysis.

[0451] As a result, the peak area value derived from Hid-DPPrdPhen could not be obtained by LC / MS analysis.

[0452] Therefore, it can be seen that the Hid-DPPrdPhen of one aspect of the present invention has low solubility in water and is applicable to light-emitting devices (i.e., light-emitting devices processed using lithography) whose manufacturing process includes the use of water or a drug solution with water as a solvent. Example 8

[0453] <<Synthesis Example 8>> In this synthetic example, the method for synthesizing 4-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-7-[3-(1-naphthyl)-1-pyrrolidinyl]-1,10-phenanthroline (abbreviated as: Hid-αNPrdPhen), represented by structural formula (101) in Embodiment 1, is described. The structure of Hid-αNPrdPhen is shown below.

[0454] [Chemical Formula 51]

[0455] 2.6 g (7.7 mmol) of 4-chloro-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline, 2.0 g (8.6 mmol) of 3-(naphth-1-yl)pyrrolidine hydrochloride, and 3.6 g (24 mmol) of diazabicycloundecene (DBU) were placed in a 50 mL three-necked flask and stirred at 100 °C for 8 hours under a nitrogen atmosphere. After stirring, the mixture was cooled to room temperature. Water was added to the mixture, and the mixture was extracted with chloroform. The extract was concentrated to obtain an oil. Acetone was added to the oil, and the mixture was sonicated. The solid was collected by vacuum filtration to obtain a pale red solid of the target compound (3.6 g, 92% yield). The following formula (s8-1) shows the synthetic scheme of this example.

[0456] [Chemical Formula 52]

[0457] 2.1 g of the obtained pale red solid (3.6 g) was purified by sublimation using a gradient sublimation method. The sublimation was performed at an argon flow rate of 0 mL / min and a pressure of 4.5 × 10⁻⁶. -2 The analyte was purified by sublimation under heating conditions of 255°C for 24 hours. The result was a yellow solid (0.20 g, recovery rate 9.5%).

[0458] Figures 20A to 20C The obtained yellow solid is shown. 11H NMR spectrum. Figure 20B is an enlarged Figure 20A and shows the range from 6.5 ppm to 9.0 ppm, Figure 20C and this is a figure showing the enlarged range from 1.0 ppm to 4.5 ppm. In addition, the measurement results by 1 1H NMR are shown below. From these results, it was confirmed that Hid-αNPrdPhen could be obtained by this synthesis example.

[0459] 1 1H NMR (CDCl3, 300 MHz): δ = 8.79 (1H, d, J = 5.5 Hz), 8.73 (1H, d, J = 5.5 Hz), 8.16 (1H, d, J = 7.7 Hz), 7.99 - 7.89 (3H, m), 7.80 (1H, t, J = 4.6 Hz), 7.58 - 7.45 (4H, m), 6.79 (1H, d, J = 5.5 Hz), 6.67 (1H, d, J = 5.5 Hz), 4.38 - 4.25 (2H, m), 3.98 - 3.82 (3H, m), 3.76 - 3.55 (4H, m), 2.59 - 2.32 (4H, m), 1.63 - 1.39 (8H, m).

[0460] The glass transition temperature (Tg) of Hid-αNPrdPhen was measured. Using a differential scanning calorimeter (DSC8500 manufactured by PerkinElmer Japan Co., Ltd.), the powder was placed on an aluminum cell and heated at a rate of 40 °C / min to measure Tg. From the results, it was found that the Tg of Hid-αNPrdPhen was 125 °C.

[0461] Next, a solubility test of Hid-αNPrdPhen was carried out. Note that this test was carried out at one atmosphere and room temperature (RT).

[0462] <Solubility test of Hid-αNPrdPhen using LC / MS analysis> In LC / MS analysis, LC (liquid chromatography) separation was carried out using Acquity UPLC manufactured by Waters Corporation, and MS analysis (mass spectrometry) was carried out using Xevo G2 TofMS manufactured by Waters Corporation. The chromatographic column used in LC separation was Acquity UPLC BEH C8 (2.1×100 mm, 1.7 μm). Acetonitrile was used as mobile phase A, and 0.1% aqueous formic acid solution was used as mobile phase B. In addition, the injection volume of the sample was 5.0 μL. Note that the wavelength of the photodiode array detector was analyzed at 254 nm ± 1 nm.

[0463] 1 mg of Hid-αNPrdPhen was placed in a 5 mL sample vial, and 2 mL of chloroform was added. The vial was then subjected to ultrasonic irradiation for 10 minutes. After confirming complete dissolution of the solid, the solution was diluted 2.5 times with acetonitrile to adjust the concentration to 0.20 g / L. This solution was then diluted with acetonitrile to adjust the concentrations to 2.5 mg / L and 0.5 mg / L. LC / MS analysis was performed using the adjusted solutions, and calibration curves were constructed using the peak areas derived from Hid-αNPrdPhen at each concentration.

[0464] Next, the solubility of Hid-αNPrdPhen in water was measured.

[0465] Place 1 mg of Hid-αNPrdPhen in a 5 mL sample vial, add 1 mL of water, and irradiate with ultrasound for 5 minutes. Filter the mixture using a membrane filter to remove solids, and dilute the filtrate 5-fold with acetonitrile. Analyze the resulting solution by LC / MS.

[0466] The calibration curve and signal intensity obtained from LC / MS analysis show that 0.0023 mg of Hid-αNPrdPhen dissolves in 1 mL of water. Furthermore, the solubility of Hid-αNPrdPhen in water can be calculated as 2.3 × 10⁻⁶ mg. -6 The weight fraction of Hid-αNPrdPhen has low solubility in water.

[0467] Therefore, it can be seen that the Hid-αNPrdPhen of one aspect of the present invention has low solubility in water and is applicable to light-emitting devices (i.e., light-emitting devices processed using lithography) whose manufacturing process includes the use of water or a drug solution with water as a solvent. Example 9

[0468] <<Synthesis Example 9>> In this synthetic example, the method for synthesizing 4-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-7-[4-(1-naphthyl)phenyl]-1,10-phenanthroline (abbreviated as: Hid-αNPPhen), represented by structural formula (103) in Embodiment 1, is described. The structure of Hid-αNPPhen is shown below.

[0469] [Chemical Formula 53]

[0470] 2.4 g (6.3 mmol) of 4-bromo-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline, 1.7 g (6.9 mmol) of 4-(1-naphthyl)phenylboronic acid, 0.16 g (0.45 mmol) of di(1-adamantane)-n-butylphosphine, 3.4 g (10 mmol) of cesium carbonate, 36 mL of 1,4-dioxane, and 13 mL of water were placed in a 100 mL three-necked flask and degassed by stirring under reduced pressure. 0.17 g (0.19 mmol) of tris(dibenzylacetone)dipalladium(O) was added to the mixture, and the mixture was stirred at 100 °C for 30 hours under a nitrogen stream. After stirring, the mixture was cooled to room temperature. Water was added to the mixture, and extraction was performed using dichloromethane. The extract was concentrated to obtain an oil. The oily substance was purified by silica gel column chromatography (developing solvents: chloroform and methanol, respectively). The obtained fraction was concentrated to obtain an oily substance. A small amount of chloroform and ethyl acetate were added to the oily substance and it was irradiated with ultrasound. The precipitated solid was collected by vacuum filtration, thereby obtaining a light brown solid of the target substance (1.2 g, yield 39%). The following formula (s9-1) shows the synthetic scheme of this synthetic example.

[0471] [Chemical Formula 54]

[0472] The obtained light brown solid (1.2 g) was purified by sublimation using a gradient sublimation method. The argon flow rate was 0 mL / min and the pressure was 3.2 × 10⁻⁶. -2 Sublimation purity was determined by heating at 240°C for 43 hours. The result was a yellow solid (0.55 g, recovery rate 46%) of the target compound.

[0473] Figures 21A to 21C The obtained yellow solid is shown. 1 H NMR spectrum. Figure 21B It is magnification Figure 21A The graph shows the range of 6.5 ppm to 9.5 ppm. Figure 21C This is a graph shown magnified to the range of 1.0 ppm to 4.0 ppm. Additionally, the following shows... 1 The results of the 1H NMR measurements confirmed the presence of Hid-α NPPhen.

[0474] 1H NMR (CDCl3, 300MHz): δ=9.20 (1H, d, J=4.4Hz), 8.79 (1H, d, J=5.5Hz), 8.23 ​​(1H, d, J=9.9Hz), 8.04 (1H, d, J=7.3Hz), 7.97-7.91 (2H, m ), 7.83 (1H, d, J = 9.5Hz), 7.69 (4H, s), 7.62-7.48 (5H, m), 6.75 (1H, d, J = 5.9Hz), 3.77-3.63 (4H, m), 2.39 (2H, br), 1.64-1.46 (8H, m).

[0475] The glass transition temperature (Tg) of Hid-α NPPhen was measured. The powder was placed on an aluminum element and heated at 40 °C / min using a differential scanning calorimeter (DSC8500, manufactured by PerkinElmer Japan Co., Ltd.). The results show that the Tg of Hid-α NPPhen is 124 °C, indicating good heat resistance. Example 10

[0476] <<Synthesis Example 10>> In this synthetic example, the method for synthesizing 4-(6,7-dihydro-5H-dibenzo[c,e]azapheno-5-yl)-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviated as: Hid-ceHBazPhen), represented by structural formula (102) in Embodiment 1, is described. The structure of Hid-ceHBazPhen is shown below.

[0477] [Chemical Formula 55]

[0478] 3.4 g (10 mmol) of 4-chloro-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline, 2.6 g (11 mmol) of 6,7-dihydro-5H-dibenzo[c,e]azapyridine hydrochloride, and 4.6 g (30 mmol) of diazabicycloundecene (DBU) were placed in a 100 mL three-necked flask and stirred at 100 °C for 32 hours under a nitrogen stream. After stirring, the mixture was cooled to room temperature. Water was added to the mixture, and the mixture was extracted with chloroform. The extract was concentrated to obtain an oil. Ethyl acetate was added to the oil, and the mixture was sonicated. The precipitated solid was separated by vacuum filtration, and the filtrate was concentrated to obtain the oil. A small amount of ethyl acetate was added to the oil, and the mixture was sonicated. The precipitated solid was collected by vacuum filtration, yielding a light brown solid (2.1 g, 42% yield) of the target compound. The following equation (s10-1) shows the synthesis scheme of this synthesis example.

[0479] [Chemical Formula 56]

[0480] Figures 22A to 22C The resulting light brown solid is shown. 1 H NMR spectrum. Figure 22B It is magnification Figure 22A The graph shows the range of 6.5 ppm to 9.0 ppm. Figure 22C This is a graph shown magnified to the range of 1.0 ppm to 4.5 ppm. Additionally, the following shows... 1 The H NMR measurement results confirmed the presence of Hid-ceHBazPhen.

[0481] 1 H NMR (CDCl3, 300MHz): δ=8.87 (1H, d, J=5.1Hz), 8.75 (1H, d, J=5.5Hz), 8.14 (1H, d, J=9.5Hz), 7.83 (1H, d, J=9.5Hz), 7.60 (2H, d, J=7.3Hz), 7.51 (2H, t, J=7.5Hz ), 7.36 (2H, t, J = 7.3Hz), 7.22 (2H, d, J = 7.3Hz), 7.00 (1H, d, J = 5.1Hz), 6.71 (1H , d, J=5.5Hz), 4.27 (4H, s), 3.78-3.63 (4H, m), 2.39 (2H, br), 1.61-1.44 (8H, m). Example 11

[0482] In this embodiment, a light-emitting device according to one aspect of the present invention is described in detail. The structural formulas of the main organic compounds used in this embodiment are shown below.

[0483] [Chemical Formula 57]

[0484] (Manufacturing method of light-emitting device 1-1) First, as a reflective electrode, an alloy of silver, palladium, and copper (APC: Ag-Pd-Cu) is deposited on a substrate using sputtering to a thickness of 100 nm. Then, as a transparent electrode, indium tin oxide (ITSO) containing silicon oxide is stacked using sputtering to a thickness of 50 nm, forming a first electrode 101 with dimensions of 2 mm × 2 mm. Note that the transparent electrode is used as the anode and is considered as the first electrode 101 together with the aforementioned reflective electrode.

[0485] Next, as a pretreatment for forming light-emitting devices on the substrate, the substrate surface is washed with water and baked at 200°C for 1 hour.

[0486] Then, the substrate is placed inside and depressurized to 1×10⁻⁶. -4 The substrate is placed in a vacuum evaporation equipment with a temperature of approximately 170°C and baked in a vacuum chamber for 30 minutes. Then, the substrate is cooled for about 30 minutes.

[0487] Next, the substrate is fixed on a support provided in a vacuum evaporation apparatus with the surface on which the first electrode 101 is formed facing down. A hole injection layer 111 is formed on the first electrode 101 by evaporation in a weight ratio of 1:0.03 (=PCBBiF:OCHD-003) of N-(biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2-amine (abbreviated as: PCBBiF) represented by the above structural formula (i) and an electron acceptor material (OCHD-003) containing fluorine with a molecular weight of 672 and a thickness of 10 nm.

[0488] PCBiF is deposited on the hole injection layer 111 with a thickness of 110 nm to form the first hole transport layer.

[0489] Next, on the first hole transport layer, 8-(p-terphenyl-3-yl)-4-[3-(dibenzothiophene-4-yl)phenyl]-[1]benzofurano[3,2-d]pyrimidine (abbreviated as: 8mpTP-4mDBtPBfpm) represented by the above structural formula (ii), 9-(2-naphthyl)-9'-phenyl-3,3'-bi-9H-carbazole (abbreviated as: βNCCP) represented by the above structural formula (iii), and [2-d3-methyl-8-(2-pyridine)] represented by the above structural formula (iv) are used. The first luminescent layer is formed by co-evaporation of iridium(III) (abbreviated as Ir(5mppy-d3)2(mbfpypy-d3)) in a weight ratio of 0.5:0.5:0.1 (=8mpTP-4mDBtPBfpm:βNCCP:Ir(5mppy-d3)2(mbfpypy-d3)) with a thickness of 40 nm.

[0490] Then, 2-{3-[3-(N-phenyl-9H-carbazo-3-yl)-9H-carbazo-9-yl]phenyl}dibenzo[f,h]quinoxaline (abbreviated as 2mPCCzPDBq) representing the above structural formula (v) is deposited with a thickness of 10 nm to form the first electron transport layer.

[0491] After forming the first electron transport layer, 2,2'-([2,2'-bipyridine]-6,6'-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviated as 6,6'(P-Bqn)2BPy) and 4-(3,4-diphenyl-1-pyrrolidinyl)-7-(2,6'-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviated as 6,6'(P-Bqn)2BPy) (abbreviated as 4-(3,4-diphenyl-1-pyrrolidinyl)-7-(2,6'-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviated as 6,6'(P-Bqn)2BPy) (abbreviated as 4-(3,4-diphenyl-1-pyrrolidinyl)-7-(2,6'-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviated as 4,6'(P-Bqn)2BPy) (abbreviated as 4-phenyl-1-pyrrolidinyl)-7-(2,6'-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviated as 4 ... A first layer is formed by 3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviated as Hid-DPPrdPhen) and lithium oxide (Li2O). A third layer is formed by evaporating copper phthalocyanine (abbreviated as CuPc) represented by the above structural formula (viii) with a thickness of 2 nm. Then, a second layer is formed by co-evaporating PCBBiF and OCHD-003 with a weight ratio of 1:0.15 (=PCBBiF:OCHD-003) and a thickness of 10 nm, thereby forming an intermediate layer.

[0492] PCBiF is deposited on the intermediate layer with a thickness of 50 nm to form the second hole transport layer.

[0493] A second light-emitting layer is formed by co-evaporation on the second hole transport layer with a weight ratio of 8mpTP-4mDBtPBfpm, βNCCP, and Ir(5mppy-d3)2(mbfpypy-d3) of 0.5:0.5:0.1 (=8mpTP-4mDBtPBfpm:βNCCP:Ir(5mppy-d3)2(mbfpypy-d3)) and a thickness of 40nm.

[0494] Then, after depositing 2mPCCzPDBq with a thickness of 20 nm, 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviated as mPPhen2P) with a thickness of 20 nm is deposited, thereby forming the second electron transport layer.

[0495] Then, an electron injection layer is formed by co-evaporation of lithium fluoride (LiF) and ytterbium (Yb) at a volume ratio of 1:0.5 (=LiF:Yb) and a thickness of 1.5 nm. Next, a second electrode 102 is formed by co-evaporation of silver (Ag) and magnesium (Mg) at a volume ratio of 1:0.1 and a thickness of 15 nm. Furthermore, 4,4',4”-(phenyl-1,3,5-triyl)tris(dibenzothiophene) (abbreviated as DBT3P-II) represented by the above structural formula (x) is deposited on the second electrode 102 as a capping layer with a thickness of 70 nm, thereby improving the light extraction efficiency.

[0496] Next, in a glove box under a nitrogen atmosphere, a glass substrate is used to seal the light-emitting device in a manner that prevents it from being exposed to the atmosphere (UV-curable sealing material is applied around the device, and UV is irradiated only to the sealing material without irradiating the light-emitting device, and heat treatment is performed at 80°C for 1 hour under atmospheric pressure), thereby forming the light-emitting device 1-1.

[0497] (Manufacturing method of light-emitting device 1-2) In the light-emitting device 1-2, 4-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-7-[3-(1-naphthyl)-1-pyrrolidinyl]-1,10-phenanthroline (abbreviated as Hid-αNPrdPhen), represented by the above structural formula (xi), is used instead of Hid-DPPrdPhen used in the first layer of the light-emitting device 1-1, and is otherwise manufactured in the same manner as the light-emitting device 1-1.

[0498] (Compare the manufacturing methods of light-emitting device 1) In comparative light-emitting device 1, 4,7-bis(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviated as Hid2Phen), represented by the above structural formula (xii), is used instead of Hid-DPPrdPhen used in the first layer of light-emitting device 1-1, and is otherwise manufactured in the same manner as light-emitting device 1-1.

[0499] The device structures of light-emitting device 1-1, light-emitting device 1-2, and comparative light-emitting device 1 are shown below.

[0500] [Table 1]

[0501] [Table 2]

[0502] Figure 23 The brightness-current density characteristics of light-emitting device 1-1, light-emitting device 1-2, and comparative light-emitting device 1 are shown. Figure 24 The current efficiency-brightness characteristics are shown. Figure 25 The brightness-voltage characteristics are shown. Figure 26 The current density-voltage characteristics are shown. Figure 27 The electroluminescence spectrum is shown. Furthermore, Table 3 shows that the luminance of light-emitting device 1-1, light-emitting device 1-2, and comparative light-emitting device 1 is 1000 cd / m². 2 Key characteristics of the surrounding area. Note that luminance, CIE chromaticity, and electroluminescence spectrum were measured at room temperature using a spectroradiometer (SR-UL1R manufactured by Topcon).

[0503] [Table 3]

[0504] Depend on Figures 23 to 27 As shown in Table 2, all devices exhibit high current efficiency and are used as series-type light-emitting devices.

[0505] As can be seen from the above results, the light-emitting device that uses the organic compound represented by the general formula (G1) in Embodiment 1 as the first layer of the tandem light-emitting device is a light-emitting device with good characteristics. Example 12

[0506] In this embodiment, a light-emitting device according to one aspect of the present invention is described in detail. The structural formulas of the main organic compounds used in this embodiment are shown below.

[0507] [Chemical Formula 58]

[0508] (Manufacturing method of light-emitting device 2-1) First, an alloy of silver, palladium, and copper (APC: Ag-Pd-Cu) is deposited on a substrate with a thickness of 100 nm using sputtering to serve as a transparent electrode. Then, an indium tin oxide (ITSO) layer containing silicon oxide is stacked on a substrate with a thickness of 50 nm using sputtering. This stacked film is then patterned using photolithography to form the first electrode. The patterned first electrode has multiple electrodes arranged in a 2 mm × 2 mm area with a resolution of 508 ppi, forming a first electrode group.

[0509] Next, as a pretreatment for forming light-emitting devices on the substrate, the substrate surface is washed with water and baked at 200°C for 1 hour.

[0510] Then, the substrate is placed inside and depressurized to 1×10⁻⁶. -4 The substrate is placed in a vacuum evaporation equipment with a temperature of approximately 170°C and baked in a vacuum chamber for 30 minutes. Then, the substrate is cooled for about 30 minutes.

[0511] Next, the substrate is fixed on a support provided in a vacuum evaporation apparatus with the surface on which the first electrode 101 is formed facing down. A hole injection layer 111 is formed on the first electrode 101 by evaporation in a weight ratio of 1:0.03 (=PCBBiF:OCHD-003) of N-(biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2-amine (abbreviated as: PCBBiF) represented by the above structural formula (i) and an electron acceptor material (OCHD-003) containing fluorine with a molecular weight of 672 and a thickness of 10 nm.

[0512] PCBiF is deposited on the hole injection layer 111 with a thickness of 110 nm to form the first hole transport layer.

[0513] Next, on the first hole transport layer, 8-(p-terphenyl-3-yl)-4-[3-(dibenzothiophene-4-yl)phenyl]-[1]benzofurano[3,2-d]pyrimidine (abbreviated as: 8mpTP-4mDBtPBfpm) represented by the above structural formula (ii), 9-(2-naphthyl)-9'-phenyl-3,3'-bi-9H-carbazole (abbreviated as: βNCCP) represented by the above structural formula (iii), and [2-d3-methyl-8-(2-pyridine)] represented by the above structural formula (iv) are used. The first luminescent layer is formed by co-evaporation of iridium(III) (abbreviated as Ir(5mppy-d3)2(mbfpypy-d3)) in a weight ratio of 0.5:0.5:0.1 (=8mpTP-4mDBtPBfpm:βNCCP:Ir(5mppy-d3)2(mbfpypy-d3)) with a thickness of 40 nm.

[0514] Then, 2-{3-[3-(N-phenyl-9H-carbazo-3-yl)-9H-carbazo-9-yl]phenyl}dibenzo[f,h]quinoxaline (abbreviated as 2mPCCzPDBq) representing the above structural formula (v) is deposited with a thickness of 10 nm to form the first electron transport layer.

[0515] After the formation of the first electron transport layer, 2,2'-([2,2'-bipyridine]-6,6'-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviated as: 6,6'(P-Bqn)2BPy) represented by the above structural formula (vi), 4-(3,4-diphenyl-1-pyrrolidinyl)-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviated as: Hid-DPPrdPhen) represented by the above structural formula (vii), and lithium oxide (Li2O) are used. The first layer is formed by co-evaporation with a volume ratio of 0.5:0.5:0.02 (=6,6'(P-Bqn)2BPy:Hid-DPPrdPhen:Li2O) and a thickness of 5nm. The third layer is formed by evaporation with a thickness of 2nm using copper phthalocyanine (CuPc) represented by the above structural formula (viii). The second layer is formed by co-evaporation with a weight ratio of PCBBiF and OCHD-003 of 1:0.15 (=PCBBiF:OCHD-003) and a thickness of 10nm. Thus, the intermediate layer is formed.

[0516] PCBiF is deposited on the intermediate layer with a thickness of 50 nm to form the second hole transport layer.

[0517] A second light-emitting layer is formed by co-evaporation on the second hole transport layer with a weight ratio of 8mpTP-4mDBtPBfpm, βNCCP, and Ir(5mppy-d3)2(mbfpypy-d3) of 0.5:0.5:0.1 (=8mpTP-4mDBtPBfpm:βNCCP:Ir(5mppy-d3)2(mbfpypy-d3)) and a thickness of 40nm.

[0518] Then, after depositing 2mPCCzPDBq with a thickness of 20 nm, 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviated as mPPhen2P) with a thickness of 20 nm is deposited, thereby forming the second electron transport layer.

[0519] Next, tri(8-hydroxyquinoline) aluminum (Alq3) is vapor-deposited with a thickness of 10 nm to form the first protective layer.

[0520] Then, after the substrate formed on the first protective layer is removed from the vacuum evaporation apparatus and exposed to the atmosphere, aluminum oxide is deposited using trimethylaluminum (TMA) as a precursor and water vapor as an oxidant via the ALD method with a thickness of 30 nm, thereby using the aluminum oxide film as the second protective layer.

[0521] Molybdenum was deposited on the second protective layer with a thickness of 50 nm using a sputtering method, thereby forming the third protective layer.

[0522] A photoresist is applied to the third protective layer, followed by exposure and development, corresponding to each of the multiple first electrodes and processed independently for each electrode, thereby achieving a resolution of 508ppi.

[0523] Using a photoresist as a mask, the third protective layer is processed with an etching gas containing SF6 and oxygen (O2). Using the processed third protective layer as a hard mask, the second protective layer is processed with an etching gas containing trifluoromethane (CHF3) and helium (He). Then, the hole injection layer, the first hole transport layer, the first light-emitting layer, the first electron transport layer, the intermediate layer, the second hole transport layer, the second light-emitting layer, and the second electron transport layer are processed with an etching gas containing oxygen (O2).

[0524] After processing the organic compound layer, the third protective layer is removed using an etching gas containing SF6 and oxygen (O2), leaving the second protective layer. Then, aluminum oxide is deposited at a thickness of 15 nm using the ALD method, thereby forming the fourth protective layer.

[0525] Next, a photosensitive polymer material is formed on the first electrode on the fourth protective layer using photolithography. Then, it is heated at 100°C for 10 minutes in an atmospheric atmosphere, and then the unwanted portions of the first, second, and fourth protective layers are removed using a mixed acid aqueous solution containing hydrofluoric acid (HF), exposing the second electron transport layer. At this point, the photosensitive polymer material is used as a photoresist.

[0526] The substrate that exposes the second electron transport layer is placed inside it and depressurized to 1×10⁻⁶. -4 In a vacuum evaporation apparatus with a pressure of approximately 100 Pa, vacuum baking is performed at 100°C for 60 minutes in the heating chamber of the vacuum evaporation apparatus.

[0527] Then, an electron injection layer is formed by co-evaporation of lithium fluoride (LiF) and ytterbium (Yb) at a volume ratio of 1:0.5 (=LiF:Yb) and a thickness of 1.5 nm. Next, a second electrode 102 is formed by co-evaporation of silver (Ag) and magnesium (Mg) at a volume ratio of 1:0.1 and a thickness of 15 nm. Furthermore, 4,4',4”-(phenyl-1,3,5-triyl)tris(dibenzothiophene) (abbreviated as DBT3P-II) represented by the above structural formula (x) is deposited on the second electrode 102 as a capping layer with a thickness of 70 nm, thereby improving the light extraction efficiency.

[0528] Next, in a glove box under a nitrogen atmosphere, a glass substrate is used to seal the light-emitting device in a manner that prevents it from being exposed to the atmosphere (UV-curable sealing material is applied around the device, and UV is irradiated only to the sealing material without irradiating the light-emitting device, and heat treatment is performed at 80°C for 1 hour under atmospheric pressure), thereby forming the light-emitting device 2-1.

[0529] (Manufacturing method of light-emitting device 2-2) In the light-emitting device 2-2, 4-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-7-[3-(1-naphthyl)-1-pyrrolidinyl]-1,10-phenanthroline (abbreviated as Hid-αNPrdPhen), represented by the above structural formula (xi), is used instead of Hid-DPPrdPhen used in the first layer of the light-emitting device 2-1, and is otherwise manufactured in the same manner as the light-emitting device 2-1.

[0530] (Compare the manufacturing methods of light-emitting device 2) In comparative light-emitting device 2, 4,7-bis(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviated as Hid2Phen), represented by the above structural formula (xii), is used instead of Hid-DPPrdPhen used in the first layer of light-emitting device 2-1, and is otherwise manufactured in the same manner as light-emitting device 2-1.

[0531] The device structures of light-emitting device 2-1, light-emitting device 2-2, and comparative light-emitting device 2 are shown below.

[0532] [Table 4] Processing using photolithography

[0533] [Table 5]

[0534] Figure 28 The brightness-current density characteristics of light-emitting device 2-1, light-emitting device 2-2, and comparative light-emitting device 2 are shown. Figure 29 The current efficiency-brightness characteristics are shown. Figure 30 The brightness-voltage characteristics are shown. Figure 31 The current density-voltage characteristics are shown. Figure 32 The electroluminescence spectrum is shown. Additionally, Table 6 shows that the luminance of light-emitting device 2-1, light-emitting device 2-2, and comparative light-emitting device 2 is 1000 cd / m². 2 Key characteristics of the surrounding area. Note that luminance, CIE chromaticity, and electroluminescence spectrum were measured at room temperature using a spectroradiometer (SR-UL1R manufactured by Topcon).

[0535] [Table 6]

[0536] Depend on Figures 28 to 32 As shown in Table 6, although all devices are processed by photolithography with exposure to the atmosphere during the formation of the light-emitting device, they exhibit high current efficiency and are used as series-type light-emitting devices.

[0537] As can be seen from the above results, the light-emitting device that uses the organic compound represented by the general formula (G1) in Embodiment 1 as the first layer of the tandem light-emitting device has good characteristics even when processed by photolithography. Example 13

[0538] <<Synthesis Example 11>> In this synthetic example, the synthesis method of 4-(4-azatricyclo[5.2.2.0, 2, 6]undecane-4-yl)-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviated as: Hid-AcuPhen), represented by structural formula (122) in Embodiment 1, is described. The structure of Hid-AcuPhen is shown below.

[0539] [Chemical Formula 59]

[0540] 1.00 g (2.96 mmol) of 4-chloro-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline, 0.69 g (3.68 mmol) of 4-azatricyclo[5.2.2.0,2,6]undecane hydrochloride, and 2.00 g (13.1 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) were placed in a 50 mL three-necked flask and stirred at 100 °C for 32 hours under a nitrogen stream. After stirring, the mixture was cooled to room temperature. Water was added to the mixture, and extraction was performed using dichloromethane. The extract was concentrated to give the crude product of the target compound (1.07 g). The following formula (s11-1) shows the synthetic scheme of this example.

[0541] [Chemical Formula 60]

[0542] Figures 33A to 33C The synthesized Hid-AcuPhen is shown. 1 H NMR spectrum. In addition... Figure 33B It is magnification Figure 33A The chart shows the range of 6.5 ppm to 9.0 ppm. Figure 33C This is a graph shown magnified to represent the range of 1.0 ppm to 4.0 ppm. Additionally, the following shows... 1 The H NMR measurement results confirmed the presence of Hid-AcuPhen.

[0543] 1H NMR (500MHz, CHLOROFORM-D) δ=8.85 (d, J=5.3Hz, 1H), 8.72 (d, J=5.4Hz, 1H), 8.08 (d, J=9.6Hz, 1H), 7.93 (d, J=9.7Hz, 1H), 6.92 (d, J=5.3Hz, 1H), 6.67 ( d, J=5.4Hz, 1H), 3.75-3.64(m, 4H), 3.54-3.48(m, 4H), 2.54-2.48(m, 2H), 2 .41-2.35(m, 2H), 1.99-1.89(m, 2H), 1.74-1.53(m, 12H), 1.49-1.39(m, 4H). Example 14

[0544] <<Synthesis Example 12>> In this embodiment, a method for synthesizing the organic compound 4-(4-azatricyclo[5.2.1.0, 2, 6]decane-4-yl)-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline (abbreviated as: Hid-AccPhen) according to one aspect of the present invention is described. The structure of Hid-AccPhen is shown below.

[0545] [Chemical Formula 61]

[0546] 1.0 g (3.0 mmol) of 4-chloro-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline, 0.64 g (3.7 mmol) of 4-azatricyclo[5.2.1.0,2,6]decane hydrochloride, and 1.1 g (7.2 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) were placed in a 50 mL three-necked flask and stirred at 100 °C for 8 hours under a nitrogen stream. After stirring, the mixture was cooled to room temperature. Water was added to the mixture, and the mixture was extracted with dichloromethane. The extract was concentrated to obtain the target compound. The following formula (s12-1) shows the synthetic scheme of Hid-AccPhen.

[0547] [Chemical Formula 62]

[0548] The mass of the obtained target compound was measured using GC-MS. The result showed a signal representing m / z 438 relative to the calculated mass of the target compound. Therefore, 4-(4-azatricyclo[5.2.1.0,2,6]decane-4-yl)-7-(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-1,10-phenanthroline was obtained.

[0549] In GC-MS analysis, a Thermo Fisher Scientific DEP-ISQ7610 was used for MS analysis using the DEP (Direct Exposure Probe) method. The ion source temperature was set to 200°C. Furthermore, the following conditions were used: the initial probe current was set to 0 mA and held for 30 seconds; then the probe current was increased at a rate of 20 mA / s for 30 seconds; finally, the probe current was increased to 800 mA and held for 30 seconds.

Claims

1. An organic compound represented by general formula (G1) or general formula (G2): in, X 2 To X 5 any one of X 6 To X 9 One of them represents a halogen or trifluoromethanesulfonyl group, and the others represent hydrogen. R 2 To R 5 any one of R 6 To R 9 Any one of them represents an aliphatic cyclic amino group represented by the general formula (g1), and the others represent hydrogen. In general formula (G1) or general formula (G2), the carbon bonded to the halogen or the trifluoromethanesulfonyl group and the carbon bonded to the aliphatic cyclic amino group represented by general formula (G1) are in an axisymmetric position in the 1,10-phenanthroline skeleton or the 2,2'-bipyridine skeleton of the main skeleton. R 11 To R 18 Each of the following groups independently represents hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a secondary amino group having 2 to 10 carbon atoms (substituted or unsubstituted), a monovalent aromatic group having 6 to 30 carbon atoms (substituted or unsubstituted), a heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen, a hydroxyl group, an amide group, and a carbonyl group. p and q independently represent 0 to 3, respectively. Furthermore, R 11 To R 18 Any two of them may bond to each other to form a ring or not bond to each other.

2. The organic compound according to claim 1, wherein the organic compound is represented by any one of general formulas (G1-1) to (G1-4): X represents halogen or trifluoromethanesulfonyl group. R represents an aliphatic cyclic amino group represented by the general formula (g1). R 11 To R 18 Each of the following groups independently represents hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a secondary amino group having 2 to 10 carbon atoms (substituted or unsubstituted), a monovalent aromatic group having 6 to 30 carbon atoms (substituted or unsubstituted), a heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen, a hydroxyl group, an amide group, and a carbonyl group. p and q independently represent 0 to 3, respectively. And R 11 To R 18 Any two of them may bond to each other to form a ring or not bond to each other.

3. The organic compound according to claim 1, wherein the organic compound is represented by any one of general formulas (G2-1) to (G2-4): X represents halogen or trifluoromethanesulfonyl group. R represents an aliphatic cyclic amino group represented by the general formula (g1). R 11 To R 18 Each of the following groups independently represents hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a secondary amino group having 2 to 10 carbon atoms (substituted or unsubstituted), a monovalent aromatic group having 6 to 30 carbon atoms (substituted or unsubstituted), a heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen, a hydroxyl group, an amide group, and a carbonyl group. p and q independently represent 0 to 3, respectively. And R 11 To R 18 Any two of them may bond to each other to form a ring or not bond to each other.

4. An organic compound represented by the general formula (G3): in, R represents the basis expressed in general formula (g1), A represents a base expressed in general formula (g2) or general formula (g3). A and R are different substituents. R 11 To R 18 and R 21 To R 28 Each of the following groups independently represents hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a secondary amino group having 2 to 10 carbon atoms (substituted or unsubstituted), a monovalent aromatic group having 6 to 30 carbon atoms (substituted or unsubstituted), a heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen, a hydroxyl group, an amide group, and a carbonyl group. p, q, s, and t independently represent 0 to 3, R 11 To R 18 Any two bonds between each other form a ring or do not bond with each other. R 21 To R 28 Any two bonds between each other form a ring or do not bond with each other. Z represents any one of the following groups: alkyl group with 1 to 10 substituted or unsubstituted carbon atoms; cycloalkyl group with 3 to 10 substituted or unsubstituted carbon atoms; monovalent aromatic group with 6 to 30 substituted or unsubstituted carbon atoms; monovalent heteroaromatic group with 1 to 30 substituted or unsubstituted carbon atoms; alkoxy group with 1 to 10 substituted or unsubstituted carbon atoms; secondary amino group, cyano group, halogen group, hydroxyl group, amide group, and carbonyl group with 2 to 10 substituted or unsubstituted carbon atoms. m represents an integer from 1 to 3. L represents any one of the following: a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms; a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms; a substituted or unsubstituted divalent aromatic group having 6 to 25 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 1 to 25 carbon atoms. Furthermore, n represents an integer from 0 to 3.

5. The organic compound according to claim 4, wherein the organic compound is represented by the general formula (G3-1): R 11 To R 18 and R 21 To R 28 Each of the following groups independently represents hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a secondary amino group having 2 to 10 carbon atoms (substituted or unsubstituted), a monovalent aromatic group having 6 to 30 carbon atoms (substituted or unsubstituted), a heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen, a hydroxyl group, an amide group, and a carbonyl group. p, q, s, and t independently represent 0 to 3, R 11 To R 18 Any two bonds between each other form a ring or do not bond with each other. R 21 To R 28 Any two bonds between each other form a ring or do not bond with each other. Furthermore, in the general formula (G3-1), different substituents are bonded to the 4 and 7 positions of the 1,10-phenanthroline skeleton.

6. The organic compound according to claim 4, wherein the organic compound is represented by the general formula (G3-2): R 11 To R 18 Each of the following groups independently represents hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a secondary amino group having 2 to 10 carbon atoms (substituted or unsubstituted), a monovalent aromatic group having 6 to 30 carbon atoms (substituted or unsubstituted), a heteroaryl group having 1 to 30 carbon atoms, a cyano group, a halogen, a hydroxyl group, an amide group, and a carbonyl group. p and q independently represent 0 to 3, respectively. R 11 To R 18 Any two bonds between each other form a ring or do not bond with each other. Z represents any one of the following groups: alkyl group with 1 to 10 substituted or unsubstituted carbon atoms; cycloalkyl group with 3 to 10 substituted or unsubstituted carbon atoms; monovalent aromatic group with 6 to 30 substituted or unsubstituted carbon atoms; monovalent heteroaromatic group with 1 to 30 substituted or unsubstituted carbon atoms; alkoxy group with 1 to 10 substituted or unsubstituted carbon atoms; secondary amino group, cyano group, halogen group, hydroxyl group, amide group, and carbonyl group with 2 to 10 substituted or unsubstituted carbon atoms. m represents an integer from 1 to 3. L represents any one of the following: alkylene group with 1 to 10 substituted or unsubstituted carbon atoms; cycloalkylene group with 3 to 10 substituted or unsubstituted carbon atoms; divalent aromatic group with 6 to 25 substituted or unsubstituted carbon atoms; and divalent heterocyclic group with 1 to 25 substituted or unsubstituted carbon atoms. And n represents an integer from 0 to 3.

7. The organic compound according to claim 4, wherein the aliphatic cyclic amino group represented by general formula (g2) is fused with an aromatic ring having 6 to 10 carbon atoms.

8. The organic compound according to claim 5, wherein an aliphatic cyclic amino group of general formula (G3-1) is fused with an aromatic ring having 6 to 10 carbon atoms.

9. A method for synthesizing a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative having two different substituents bonded to carbon at symmetrical positions, comprising the following steps: An inorganic base and solvent are used to react aliphatic cyclic amino groups with two halogen or trifluoromethanesulfonyl groups bonded to carbon at symmetrical positions.

10. A synthesis method according to claim 9, wherein the reaction is carried out by heating.

11. A synthesis method according to claim 9, wherein the inorganic base is potassium carbonate or potassium acetate.

12. A synthesis method according to claim 9, Following the reaction, a 1,10-phenanthroline derivative or a 2,2'-bipyridine derivative of an aliphatic cyclic amine bonded to one of the carbon atoms at the symmetrical position is obtained. The inorganic base is potassium carbonate or potassium acetate. The method further includes introducing other substituents into another carbon at the symmetrical position.

13. A synthesis method according to claim 9, wherein N-methyl-2-pyrrolidone is used as the solvent.

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