Organic compounds and organic light-emitting devices

Abstract

ΔE ST Provided is an organic compound that serves as a delayed fluorescence material (TADF material) with a small value. 【Solution Means】 An organic compound represented by formula (1). TIFF2026170588000045.tif41157 In formula (1), R1 to R4 are selected from a hydrogen atom, an alkyl group and the like, at least one of R1 to R4 is a group represented by formula (2), at least one of R1 to R4 is a group represented by general formula (3), R5 to R8 are selected from a hydrogen atom, an alkyl group and the like, and E is selected from a sulfur atom and the like. In formula (3), X1 to X4 are N, CR 11 selected from, R 11 is selected from a hydrogen atom, an alkyl group and the like, R 15 to R 18 are selected from a hydrogen atom, an alkyl group and the like, R 15 to R 18 two adjacent ones among them may form a group represented by formula (4), and b indicates a bonding position.

Description

[Technical Field]

[0001] This invention relates to an organic compound and an organic light-emitting device using the same. [Background technology]

[0002] An organic light-emitting element (hereinafter sometimes referred to as an "organic electroluminescent element" or "organic EL element") is an electronic element having a first electrode, a second electrode, and an organic compound layer placed between these electrodes. By injecting electrons and holes from this pair of electrodes, excitons of the light-emitting organic compound in the organic compound layer are generated, and when these excitons return to the ground state, the organic EL element emits light. Delayed fluorescence (TADF) materials generally have a structure in which a donor site and an acceptor site are bound together (hereinafter sometimes referred to as "DA type"). DA type TADF materials emit fluorescence when they return from the excited singlet state to the ground state after undergoing reverse intersystem crossing (RISC) from the excited triplet state to the excited singlet state in the excited state. In other words, in TADF materials, not only the excited singlet state but also the excited triplet state can be utilized for fluorescence emission via the reverse intersystem crossing pathway, resulting in higher luminescence efficiency compared to ordinary fluorescent materials. Since this principle was revealed, various TADF materials have been discovered through various studies. Patent document 1 describes compound A.

[0003] [ka] [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Chinese Patent Application Publication No. 103896973 Specification [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] Compound A described in Patent Document 1 has a high singlet energy, therefore the energy difference between the singlet and triplet states ΔE ST The size is large, and there is room for improvement as a delayed fluorescence material. This invention has been made in view of the above problems, and ΔE ST The objective is to provide organic compounds with small size. [Means for solving the problem]

[0006] The organic compound of the present invention is characterized by being represented by the following general formula (1).

[0007] [ka] In general formula (1), R1 to R4 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted silyl group, and a group represented by the following general formula (3). However, at least one of R1 to R4 is a group represented by the following general formula (2), and at least one of R1 to R4 is a group represented by the following general formula (3). R5 to R8 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a substituted silyl group. E is selected from sulfur, selenium, and tellurium atoms.

[0008] [ka] In general formula (2), R9 is independently selected from a hydrogen atom and a substituted or unsubstituted alkyl group. R 10 Each of these is independently selected from substituted or unsubstituted alkyl groups. 'a' indicates the bonding position.

[0009]

Chemical Formula

[0010]

Chemical Formula

Effects of the Invention

[0011] According to the present invention, an organic compound having a small ΔE ST can be provided.

Brief Description of the Drawings

[0012] [Figure 1]This figure shows the torsion angles between the central benzene ring and the acceptor (A), and the torsion angles between the central benzene ring and the donor ring (D). [Figure 2] This figure shows the orbital distribution of HOMO and LUMO. [Figure 3] (a) A schematic cross-sectional view showing an example of a pixel of a display device according to one embodiment of the present invention. (b) A schematic cross-sectional view showing an example of a display device using an organic light-emitting element according to one embodiment of the present invention. [Figure 4] This is a schematic diagram illustrating an example of a display device according to one embodiment of the present invention. [Figure 5] (a) A schematic diagram showing an example of an imaging device according to one embodiment of the present invention. (b) A schematic diagram showing an example of an electronic device according to one embodiment of the present invention. [Figure 6] (a) A schematic diagram showing an example of a display device according to one embodiment of the present invention. (b) A schematic diagram showing an example of a foldable display device. [Figure 7] (a) A schematic diagram showing an example of a lighting device according to one embodiment of the present invention. (b) A schematic diagram showing an example of a mobile body having a vehicle light fixture according to one embodiment of the present invention. [Figure 8] (a) A schematic diagram showing an example of a wearable device according to one embodiment of the present invention. (b) A schematic diagram showing another example of a wearable device according to one embodiment of the present invention. [Figure 9] (a) A schematic diagram showing an example of an image forming apparatus according to one embodiment of the present invention. (b)(c) A schematic diagram showing an example of an exposure light source for an image forming apparatus according to one embodiment of the present invention. [Modes for carrying out the invention]

[0013] In this specification, alkyl groups may have 1 to 40 carbon atoms, 1 to 20 carbon atoms, 1 to 10 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms. Specifically, examples include, but are not limited to, methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, tert-butyl groups, secondary butyl groups, pentyl groups, hexyl groups, octyl groups, cyclohexyl groups, tert-pentyl groups, and 3-methylpentan-3-yl groups.

[0014] The aryl group may have 6 to 20 carbon atoms, 6 to 18 carbon atoms, 6 to 15 carbon atoms, or 6 to 12 carbon atoms. Specifically, examples include, but are not limited to, phenyl, naphthyl, indenyl, biphenyl, terphenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, anthranyl, perilenyl, chrysenyl, and fluoranthenyl groups.

[0015] The heterocyclic group may have 3 to 24 carbon atoms, 3 to 18 carbon atoms, 3 to 12 carbon atoms, or 5 to 12 carbon atoms. Specifically, examples include, but are not limited to, pyridyl, pyrimidyl, pyrazyl, triazyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, carbazolyl, acridinyl, and phenanthrolyl groups.

[0016] Examples of substituted silyl groups include, but are not limited to, trimethylsilyl and triphenylsilyl groups.

[0017] Examples of the substituent that the aforementioned alkyl group, aryl group, heterocyclic group, or silyl group may further have include, but are not limited to, halogen atoms such as fluorine, chlorine, bromine, and iodine; alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, and tert-butyl group; alkoxy groups such as methoxy group, ethoxy group, and propoxy group; amino groups such as dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, and ditolylamino group; aryloxy groups such as phenoxy group; aryl groups such as phenyl group and biphenyl group; heterocyclic groups such as pyridyl group and pyrrolyl group; and cyano group.

[0018] (1) Organic Compound First, the organic compound according to the present embodiment will be described. The organic compound according to the present embodiment is an organic compound represented by the following general formula (1). The isotope species of the hydrogen atoms present in the molecule of the organic compound according to the present embodiment is not particularly limited, and for example, all the hydrogen atoms in the molecule may be 1 H, or a part or all of them may be 2 H (deuterium). The organic compound according to the present embodiment may be a compound exhibiting delayed fluorescence, and may be a compound exhibiting thermally activated delayed fluorescence (TADF).

[0019]

Chemical Formula

[0020] <R1 to R4> In general formula (1), R1 to R4 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted silyl group, and a group represented by the following general formula (3). Provided that at least one of R1 to R4 is a group represented by the following general formula (2), and at least one of R1 to R4 is a group represented by the following general formula (3).

[0021] When each of R1 to R4 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms, the molecular weight of the organic compound according to the present embodiment is reduced, which is preferable due to excellent sublimability. It is more preferable that R1 to R4 are each a hydrogen atom, a methyl group, a tert-butyl group, or a phenyl group. Further, when two adjacent groups among R1 to R4 are the group represented by the general formula (2) and the group represented by the general formula (3), ΔE ST is decreased, which is preferable. Further, among R1 to R4, the group adjacent to both the group represented by the general formula (2) and the group represented by the general formula (3) is preferably a group other than a hydrogen atom. It is preferable that one of R1 to R4 is the group represented by the general formula (2), and one or two of R1 to R4 are the group represented by the general formula (3).

[0022] <R5 to R8> In general formula (1), each of R5 to R8 is independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a substituted silyl group.

[0023] When each of R5 to R8 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms, the molecular weight of the organic compound according to the present embodiment is reduced, which is preferable due to excellent sublimability. From the viewpoint of molecular weight, it is more preferable that each of R5 to R8 is a hydrogen atom. The reduced molecular weight provides further superiority in terms of sublimability.

[0024] <e> E is selected from sulfur, selenium, and tellurium atoms. Since the heavy atom effect increases the reverse intersystem crossing rate, E is preferably a tellurium atom.

[0025] [ka]

[0026] <r9> In general formula (2), R9 is independently selected from a hydrogen atom and a substituted or unsubstituted alkyl group. From the viewpoint of molecular weight, alkyl groups having 1 to 4 carbon atoms are preferred, methyl groups or isopropyl groups are more preferred, and methyl groups are even more preferred.

[0027] <R 10 > In general formula (2), R 10 Each of these is independently selected from substituted or unsubstituted alkyl groups. From the viewpoint of molecular weight, alkyl groups having 1 to 4 carbon atoms are preferred, methyl groups or isopropyl groups are more preferred, and methyl groups are even more preferred.

[0028] In general formula (2), a represents the bonding position with general formula (1).

[0029]

Chemical Formula

[0030] <X1 to X4> In general formula (3), X1 to X4 are each independently selected from N and CR 11 . X1 to X4 are all independently selected from CR 11 , or one of them is N and the other three are CR 11 , which is preferable.

[0031] [R 11 R 11 is each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted silyl group, and a cyano group. When there are a plurality of CR 11 groups, each R 11 may be the same or different. R 11 is preferably a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 12 carbon atoms, or a cyano group. R 11 is more preferably a hydrogen atom, a t-butyl group or a phenyl group.

[0032] <R 15 to R 18 > In general formula (3), R 15 to R 18 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted silyl group, and a cyano group. R 15 to R 18 ​It is preferable that the group is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 12 carbon atoms, or a cyano group. 15 ~R 18 It is more preferable that this is a hydrogen atom, a t-butyl group, or a phenyl group.

[0033] R 15 ~R 18 Two adjacent R groups may form a group represented by the following general formula (4). Two adjacent R groups are R 15 and R 16 , R 16 and R 17 ,R 17 and R 18 And in particular, R 15 and R 16 When a group represented by general formula (4) is formed, chemical stability is increased, resulting in excellent device lifespan.

[0034] In general formula (3), b indicates the bonding position with general formula (1).

[0035] [ka]

[0036] <R 19 ~R 22 > In general formula (4), R 19 ~R 22 Each of these is independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a substituted silyl group. 19 ~R 22 It is preferable that it be a hydrogen atom.

[0037] <y> In general formula (4), Y is selected from oxygen, sulfur, selenium, and tellurium atoms.

[0038] <c> In general formula (4), c indicates the bonding position with general formula (3).

[0039] R 15 ~R 18 When two adjacent elements of these elements form a group represented by general formula (4), from the viewpoint of device lifetime, R 15 and R 16 It is preferable that a group represented by general formula (4) is formed, and more preferably that the group is represented by the following general formula (5).

[0040] [ka]

[0041] The group represented by general formula (3) is preferably one of the groups shown in group A below, from the viewpoint of organic EL element lifespan.

[0042] [ka]

[0043] R1 to R8, R 11 , R 15 ~R 22 From the viewpoint of sublimation properties, the substituents that may be present are preferably substituted or unsubstituted alkyl groups having 1 to 4 carbon atoms, substituted or unsubstituted aryl groups having 6 to 14 carbon atoms, substituted or unsubstituted heteroaryl groups having 6 to 12 carbon atoms, or substituted silyl groups, and more preferably any of the groups shown in group B below. In group B below, * indicates the bond position.

[0044] [ka]

[0045] <Characteristics of the compound> The organic compound of this embodiment has the following characteristics. (1) Both the donor (a group represented by general formula (3)) and the acceptor (a group represented by general formula (2)) are bonded to a carbon of the central benzene ring (a benzene ring having R1 to R4), preferably to an adjacent carbon. (2)(1) improves the separation of HOMO-LUMO and ΔE ST It becomes smaller. The following describes these features.

[0046] (1) Both the donor (a group represented by general formula (3)) and the acceptor (a group represented by general formula (2)) are bonded to a carbon of the central benzene ring (a benzene ring having R1 to R4), preferably to an adjacent carbon.

[0047] Both the donor and acceptor are bonded to the carbon of the central benzene ring shown in the general formula (6) below, so that the donor and acceptor are arranged in a twisted manner relative to the central benzene ring. From the viewpoint of twisting, it is preferable that the donor and acceptor are bonded to adjacent carbon rings of the central benzene ring, or that substituents (groups other than hydrogen atoms) are provided so as to be adjacent to either the donor or acceptor. Furthermore, the carbon ring next to R4 is considered to be substituted with a phenyl group, as shown by the bold line in the general formula (6) below. In particular, it is preferable to introduce substituents to groups adjacent to either the donor or acceptor, and it is more preferable that the donor and acceptor are adjacent to each other.

[0048] [ka]

[0049] Figure 1 shows the torsion angles of the central benzene ring and the acceptor (A), and the torsion angles of the central benzene ring and the donor (D). Figure 1(a) shows the torsion angle of compound A, Figure 1(b) shows the torsion angle of Comp.27(S), Figure 1(c) shows the torsion angle of Comp.16(S), and Figure 1(d) shows the torsion angle of Comp.1(S). Here, compound A is the compound described in Patent Document 1. Furthermore, Comp.27(S), Comp.16(S), and Comp.1(S) are compounds in the compound group (Comp.Gr.) 27,16,1 described later, where E=S.

[0050] As shown in Figure 1(a), compound A, in which the donor and acceptor are bonded to the respective benzene rings of dibenzothiophene, had a helix angle of A:156° and D:53°. In contrast, in the compounds shown in Figures 1(b) to (d), both the donor and acceptor are bonded to the carbon of the central benzene ring. As shown in Figure 1(b), Comp.27(S), which does not have substituents introduced between the donor and acceptor, had a helix angle of A:144° and D:58°. As shown in Figure 1(c), Comp.16(S), in which substituents are introduced at positions adjacent to both the donor and acceptor (between the donor and acceptor), had a helix angle of A:144° and D:83°. And as shown in Figure 1(d), Comp.1(S), in which the donor and acceptor are adjacent, had a helix angle of A:154° and D:68°. The closer the twist angle is to 90°, the more twisted it is relative to the benzene ring, and the closer it is to 180°, the more planar it becomes. In other words, in Figure 1, (a) is highly planar, (b) is more twisted than (a), and (c) and (d) are more twisted than (b).

[0051] (2)(1) improves the separation of HOMO-LUMO and ΔE ST It becomes smaller.

[0052] By twisting the donor, acceptor, and central benzene rings, orbital infiltration into the central benzene ring is prevented, resulting in improved HOMO-LUMO separation and ΔE ST The ΔE becomes smaller. In fact, Figure 2 shows the orbital distributions of the HOMO and LUMO of compound A and Comp.1(S). In compound A, the HOMO orbital is spread throughout the entire dibenzothiophene ring, and similarly the LUMO is spread throughout the entire dibenzothiophene ring, so the HOMO-LUMO overlap is large. In contrast, the HOMO of Comp.1 does not have orbital spread in the area indicated by the circle, and the overlap with the LUMO, which is spread throughout the entire dibenzothiophene ring, is small. As a result, the ΔE of compound A ST While the value of was 0.43 eV, the ΔE of Comp.1(S) ST It is small, at 0.10 eV. ST Delayed fluorescence is observed when the voltage is 0.3 eV or less. Therefore, the organic compound according to this embodiment is preferred because delayed fluorescence is observed.

[0053] Furthermore, the ΔE of each compound shown below ST The calculation results for [eV] are shown in Tables 1 and 2. Note that in the following compound group, E represents S, Se, or Te.

[0054] [ka]

[0055] [ka]

[0056] [Table 1]

[0057] [Table 2]

[0058] As shown in Tables 1 and 2, Comp.Gr.A to Comp.Gr.D, in which a donor and acceptor are arranged on each of the two benzene rings of dibenzochalcogenofen, have ΔE ST The voltage is high, at over 0.3 eV.

[0059] In contrast, Comp.Gr.1 to Comp.Gr.28 related to this embodiment have ΔE ST The ΔE is small, less than 0.3 eV. This is because the HOMO-LUMO separation is improved by arranging the donor and acceptor in a twisted manner relative to the central benzene ring. Therefore, the organic compound according to this embodiment has a ΔE ST This can show a small value. Furthermore, when the organic compound according to this embodiment is used in an organic light-emitting element, it is preferable from the viewpoint of maintaining efficiency in the high current density region.

[0060] <Specific example> The following are example compounds according to this embodiment. In the example compounds, E is S, Se, or Te.

[0061] [ka]

[0062] [ka]

[0063] [ka]

[0064] [ka]

[0065] [ka]

[0066] [ka]

[0067] (2) Organic light-emitting element Next, the organic light-emitting element of this embodiment will be described. The organic light-emitting element of this embodiment has at least a first electrode, a second electrode, and an organic compound layer disposed between these electrodes. One of the first electrode and the second electrode is the anode and the other is the cathode. In the organic light-emitting element of this embodiment, the organic compound layer may be a single layer or a laminate consisting of multiple layers, as long as it has a light-emitting layer. If the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have, in addition to the light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole-exciton blocking layer, an electron transport layer, an electron injection layer, etc. Furthermore, the light-emitting layer may be a single layer or a laminate consisting of multiple layers.

[0068] In the organic light-emitting element of this embodiment, at least one layer of the organic compound layer contains the organic compound according to this embodiment. Specifically, the organic compound according to this embodiment is included in any of the above-mentioned light-emitting layer, hole injection layer, hole transport layer, electron blocking layer, hole-exciton blocking layer, electron transport layer, electron injection layer, etc. The organic compound according to this embodiment is preferably included in the light-emitting layer.

[0069] In the organic light-emitting device of this embodiment, if the organic compound according to this embodiment is included in the light-emitting layer, the light-emitting layer may consist only of the organic compound according to this embodiment, or it may consist of the organic compound according to this embodiment and other compounds such as a second organic compound, a third organic compound, etc. In the light-emitting layer, the organic compound of this embodiment may be used as a guest and doped into the host material (second organic compound), or it may be used as an assist dopant and doped into the host material (second organic compound) together with a fluorescent material (third organic compound).

[0070] In the doped type, the host is the compound with the largest mass ratio among the compounds that make up the light-emitting layer. The guest is the compound with a smaller mass ratio than the host among the compounds that make up the light-emitting layer, and is responsible for the primary light emission. The assist dopant is the compound with a smaller mass ratio than the host among the compounds that make up the light-emitting layer, and plays the role of sensitizing excitons.

[0071] When the organic compound of this embodiment is used as a guest, the concentration of the organic compound of this embodiment is preferably 0.01% by mass or more and 50% by mass or less, and more preferably 10% by mass or more and 50% by mass or less, relative to the entire light-emitting layer. When the organic compound of this embodiment is used as an assist dopant, the concentration of the organic compound of this embodiment is preferably 1% by mass or more and 50% by mass or less, and more preferably 10% by mass or more and 50% by mass or less, relative to the entire light-emitting layer. In this case, the concentration of the fluorescent material is preferably 0.01% by mass or more and 20% by mass or less, and more preferably 0.01% by mass or more and 5% by mass or less, relative to the entire light-emitting layer.

[0072] The inventors have conducted various studies and found that when the organic compound according to this embodiment is used as a host or guest for the light-emitting layer, particularly as a guest for the light-emitting layer, a device can be obtained that exhibits high efficiency, high brightness, and extremely high durability. This light-emitting layer may be a single layer or a multi-layer, and it is also possible to mix the light-emitting color with that of the organic compound of this embodiment by including a light-emitting material having another light-emitting color. A multi-layer means a state in which one light-emitting layer and another light-emitting layer are stacked. In this case, the light-emitting color of the organic light-emitting element is not limited to the light-emitting color of the organic compound of this embodiment. More specifically, it may be white or an intermediate color. In the case of white, if the other light-emitting layer is a color other than the light-emitting color of the organic compound of this embodiment, for example, if the light-emitting color of the organic compound of this embodiment is blue, it will emit green or red light. Furthermore, the film can be formed by vapor deposition or coating.

[0073] The organic compound according to this embodiment can be used as a constituent material for organic compound layers other than the light-emitting layer constituting the organic light-emitting element of this embodiment. Specifically, it may be used as a constituent material for electron transport layers, electron injection layers, hole transport layers, hole injection layers, hole blocking layers, etc. In this case, the light emission color of the organic light-emitting element is not limited to the light emission color of the organic compound according to this embodiment. More specifically, it may be white light emission or an intermediate color.

[0074] <Other compounds> In addition to the organic compounds according to this embodiment, conventionally known low-molecular-weight and high-molecular-weight hole-injection compounds or hole-transporting compounds, host compounds, luminescent compounds, electron-injection compounds or electron-transporting compounds, etc., can be used together as needed. Examples of these compounds are listed below.

[0075] As hole-injection transport materials, materials with high hole mobility are preferred to facilitate hole injection from the anode and to transport the injected holes to the light-emitting layer. Furthermore, materials with a high glass transition temperature are preferred to suppress deterioration of the film quality, such as crystallization, in the organic light-emitting element. Examples of low-molecular-weight and high-molecular-weight materials with hole-injection transport properties include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. In addition, the above-mentioned hole-injection transport materials are also suitably used in electron-blocking layers. Alternatively, a mixture of polyethylenedioxythiophene and polystyrene sulfonic acid (PEDOT:PSS), which is commonly used as a hole injection material when manufactured by coating methods, may be used. Specific examples of compounds used as hole-injection transport materials are shown below, but are not limited to these.

[0076] [ka]

[0077] [ka]

[0078] Among the hole transport materials listed, HT16-HT18 can reduce the driving voltage when used in the layer in contact with the anode. HT16 is widely used in organic light-emitting devices. HT2-HT7, HT10, HT12, and HT22-HT28 may be used in the organic compound layer adjacent to HT16. High molecular weight compounds such as hole-transporting polyphenylene vinylene (PPV), polyfluorene (PF), polyvinylcarbazole (PVK), and their derivatives may also be used. In addition, inorganic insulating layers such as SiO2 and SiN, or organosilicon polymers such as siloxanes can also be used. Furthermore, multiple materials may be used in a single organic compound layer.

[0079] Luminescent materials primarily involved in light emission include donor-acceptor type organic compounds, boron-containing complexes, indocarbazole fused ring compounds, fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-quinolinolate)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives such as poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives. Furthermore, when producing a luminescent layer by coating, polymer compounds with luminescent properties are mainly used. This is because polymer compounds have high amorphous properties, making them less prone to crystallization compared to low molecular weight systems. Specific materials used include polymer compounds such as polyphenylene vinylene (PPV), polyfluorene (PF), polyvinylcarbazole (PVK), and their derivatives. Specific examples of compounds used as luminescent materials are shown below, but are not limited to these.

[0080] [ka]

[0081] [ka]

[0082] [ka]

[0083] [ka]

[0084] [ka]

[0085] The following are specific examples of compounds used as luminescent layer hosts or luminescence assist materials contained in the luminescent layer, but of course, they are not limited to these.

[0086] [ka]

[0087] [ka]

[0088] When used with delayed fluorescence materials or phosphorescent materials, the host material is preferably one whose triplet fluorescence is higher than that of the delayed fluorescence material. Preferred host materials include, but are not limited to, EM2-EM4, EM7-EM11, and EM14-EM16.

[0089] As electron-transporting materials, any material capable of transporting electrons injected from the cathode to the light-emitting layer can be arbitrarily selected, taking into consideration the balance with the hole mobility of the hole-transporting material. Examples of materials with electron-transporting properties include oxadiazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, and fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron-transporting materials are also suitably used in the hole-blocking layer. Specific examples of compounds used as electron-transporting materials are shown below, but are of course not limited to these.

[0090] [ka]

[0091] [ka]

[0092] Electron injection materials can be arbitrarily selected from those that allow for easy electron injection from the cathode, taking into consideration the balance with hole injection properties. Organic compounds include n-type dopants and reducing dopants. Examples include alkali metal compounds such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fluvalene derivatives, and acridine derivatives. They can also be used in combination with the above-mentioned electron transport materials.

[0093] <Configuration of an organic light-emitting element> An organic light-emitting element is provided on a substrate by forming an insulating layer, a first electrode, an organic compound layer, and a second electrode. A protective layer, a color filter, a microlens, etc., may be provided on the second electrode. If a color filter is provided, a planarization layer may be provided between it and the protective layer. The planarization layer can be made of acrylic resin or the like. The same applies when a planarization layer is provided between the color filter and the microlens. Either the first electrode or the second electrode may be the anode and the other the cathode.

[0094] [substrate] Examples of substrates include quartz, glass, silicon wafers, resins, and metals. The substrate may also be equipped with switching elements such as transistors and wiring, and an insulating layer may be provided on top of them. The insulating layer can be made of any material that allows for the formation of contact holes between it and the first electrode, while ensuring insulation from wiring that is not connected. For example, resins such as polyimide, silicon oxide, and silicon nitride can be used.

[0095] [electrode] A pair of electrodes can be used. The pair of electrodes may be an anode and a cathode. When an electric field is applied in the direction in which the organic light-emitting element emits light, the electrode with the higher potential is the anode, and the other is the cathode. Alternatively, the electrode that supplies holes to the light-emitting layer can be the anode, and the electrode that supplies electrons can be the cathode.

[0096] For the anode, materials with the largest possible work function are preferable. For example, elemental metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten, or mixtures containing these, or alloys combining them, as well as metal oxides such as tin oxide, zinc oxide, indium oxide, tin-indium oxide (ITO), and zinc-indium oxide can be used. Conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.

[0097] These electrode materials may be used individually or in combination of two or more types. Furthermore, the anode may consist of a single layer or multiple layers.

[0098] When used as a reflective electrode, materials such as chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys or laminates thereof can be used. It is also possible to use the above materials as a reflective film without serving as an electrode. Furthermore, when used as a transparent electrode, oxide transparent conductive layers such as indium tin oxide (ITO) or indium zinc oxide can be used, but are not limited to these. Photolithography can be used to form the electrodes.

[0099] On the other hand, materials with a small work function are preferred for the cathode. Examples include alkali metals such as lithium, alkaline earth metals such as calcium, and elemental metals or mixtures containing aluminum, titanium, manganese, silver, lead, and chromium. Alternatively, alloys combining these elemental metals can also be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, and zinc-silver can be used. Metal oxides such as indium tin oxide (ITO) can also be used. These electrode materials may be used individually or in combination of two or more. The cathode may also be a single-layer or multi-layer structure. Among these, silver is preferred, and a silver alloy is even more preferred to reduce silver aggregation. The alloy ratio is not important as long as silver aggregation is reduced. For example, the ratio of silver to other metals may be 1:1, 3:1, etc.

[0100] The cathode may be a top-emission element using an oxide conductive layer such as ITO, or a bottom-emission element using a reflective electrode such as aluminum (Al), and is not particularly limited. The method for forming the cathode is not particularly limited, but using DC and AC sputtering methods is more preferable because it provides good film coverage and makes it easier to reduce resistance.

[0101] [Organic compound layer] The organic compound layer may be formed as a single layer or as multiple layers. If there are multiple layers, they may be called a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, a hole blocking layer, an electron transport layer, or an electron injection layer, depending on their function. The organic compound layer is mainly composed of organic compounds, but may also contain inorganic atoms and inorganic compounds. For example, it may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, etc. The organic compound layer may be placed between the first electrode and the second electrode, or it may be placed in contact with the first electrode and the second electrode.

[0102] The organic compound layer (hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, electron injection layer, etc.) constituting the organic light-emitting element according to one embodiment of the present invention is formed by the method shown below.

[0103] The organic compound layer constituting the organic light-emitting element according to one embodiment of the present invention can be formed using a dry process such as vacuum deposition, ionization deposition, sputtering, or plasma deposition. Alternatively, instead of a dry process, a wet process can be used in which the compound is dissolved in a suitable solvent and the layer is formed by a known coating method (for example, spin coating, casting, microgravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing, flexographic printing, offset printing, inkjet printing, capillary coating, nozzle coating, etc.). Among these, vacuum deposition, ionization deposition, inkjet printing, and nozzle coating are suitable for manufacturing large-area organic light-emitting elements.

[0104] When forming the light-emitting layer using an organic compound with high solubility in organic solvents from the organic compounds of this embodiment, it is preferable to form it by a coating method. Examples of coating methods include spin coating, slit coating, printing, inkjet, dispensing, and spraying. Alternatively, the light-emitting layer may be formed by vacuum deposition.

[0105] When layers are formed using methods such as vacuum deposition or solution coating, crystallization is less likely to occur, resulting in excellent stability over time. Furthermore, when forming films using coating methods, it is possible to combine the film with an appropriate binder resin.

[0106] Examples of the binder resins mentioned above include, but are not limited to, polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, and urea resin.

[0107] Furthermore, these binder resins may be used individually as homopolymers or copolymers, or as a mixture of two or more types. Additionally, known additives such as plasticizers, antioxidants, and UV absorbers may be used in combination as needed.

[0108] The thickness of each layer in an organic light-emitting device is usually preferably between 1 nm and 10 μm. In particular, the thickness of the light-emitting layer of the organic compound layer is preferably between 10 nm and 100 μm in order to obtain effective light-emitting properties.

[0109] [Protective layer] A protective layer may be provided on the second electrode. For example, by bonding glass with a desiccant to the second electrode, the intrusion of water and other substances into the organic compound layer can be reduced, thereby reducing the occurrence of display defects. In another embodiment, a passivation film such as silicon nitride may be provided on the second electrode to reduce the intrusion of water and other substances into the organic compound layer. For example, after forming the second electrode, it may be transported to another chamber without breaking the vacuum and a silicon nitride film with a thickness of 2 μm may be formed by the CVD method to serve as a protective layer. A protective layer may also be provided using atomic deposition (ALD) after film formation by the CVD method. The material of the film formed by the ALD method is not limited, but may be silicon nitride, silicon oxide, aluminum oxide, etc. Silicon nitride may be further formed on the film formed by the ALD method by the CVD method. The film formed by the ALD method may have a thinner film thickness than the film formed by the CVD method. Specifically, it may be 50% or less, or even 10% or less.

[0110] [Color Filter] A color filter may be provided on top of the protective layer. For example, a color filter that takes into account the size of the organic light-emitting element may be provided on a separate substrate and bonded to the substrate on which the organic light-emitting element is provided, or a color filter may be patterned on the protective layer as described above using photolithography technology. The color filter may be made of polymer.

[0111] [Planarization layer] A planarizing layer may be provided between the color filter and the protective layer. The planarizing layer is provided to reduce the unevenness of the layer below. It may also be called a material resin layer without limiting its purpose. The planarizing layer may be composed of an organic compound, which may be low molecular weight or high molecular weight, but high molecular weight is preferred.

[0112] The planarization layer may be provided above or below the color filter, and its constituent materials may be the same or different. Specifically, examples include polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, urea resin, etc.

[0113] [Microlens] An organic light-emitting element may have optical components such as microlenses on its light-emitting side. Microlenses may be made of acrylic resin, epoxy resin, or the like. Microlenses may be used to increase the amount of light extracted from the organic light-emitting element or to control the direction of the extracted light. Microlenses may have a hemispherical shape. If they have a hemispherical shape, among the tangents tangent to the hemisphere, there is a tangent parallel to the insulating layer, and the point of contact between that tangent and the hemisphere is the vertex of the microlens. The vertex of the microlens can be similarly determined in any cross-sectional view. That is, among the tangents tangent to the semicircle of the microlens in the cross-sectional view, there is a tangent parallel to the insulating layer, and the point of contact between that tangent and the semicircle is the vertex of the microlens.

[0114] Furthermore, the midpoint of a microlens can also be defined. In the cross-section of a microlens, a line segment can be imagined from the point where one arc ends to the point where another arc ends, and the midpoint of this line segment can be called the midpoint of the microlens. The cross-section used to determine the vertices and midpoints may be a cross-section perpendicular to the insulating layer.

[0115] [Opposite substrate] A counter substrate may be provided on the planarized layer. The counter substrate is called a counter substrate because it is provided in a position corresponding to the aforementioned substrate. The constituent material of the counter substrate may be the same as that of the aforementioned substrate. The counter substrate may be the second substrate if the aforementioned substrate is referred to as the first substrate.

[0116] [Pixel circuit] An organic light-emitting device having an organic light-emitting element may have a pixel circuit connected to the organic light-emitting element. The pixel circuit may be an active-matrix type that independently controls the light emission of a first light-emitting element and a second light-emitting element. The active-matrix type circuit may be voltage-programmed or current-programmed. The driving circuit has a pixel circuit for each pixel. The pixel circuit may include a light-emitting element, a transistor that controls the light emission brightness of the light-emitting element, a transistor that controls the light emission timing, a capacitor that holds the gate voltage of the transistor that controls the light emission brightness, and a transistor for connecting to GND without going through the light-emitting element.

[0117] The light-emitting device has a display area and a peripheral area arranged around the display area. The display area has a pixel circuit, and the peripheral area has a display control circuit. The mobility of the transistors constituting the pixel circuit may be smaller than the mobility of the transistors constituting the display control circuit. The slope of the current-voltage characteristic of the transistors constituting the pixel circuit may be smaller than the slope of the current-voltage characteristic of the transistors constituting the display control circuit. The slope of the current-voltage characteristic can be measured by the so-called Vg-Ig characteristic. The transistors constituting the pixel circuit are transistors connected to the light-emitting element, such as the first light-emitting element.

[0118] [Pixels] An organic light-emitting device having an organic light-emitting element may have a plurality of pixels. Each pixel may have subpixels that emit light of a different color from the others. The subpixels may each have, for example, RGB light-emitting colors.

[0119] A pixel emits light in a region also called the pixel aperture. The pixel aperture may be 15 μm or less, or 5 μm or more. More specifically, it may be 11 μm, 9.5 μm, 7.4 μm, 6.4 μm, etc. The distance between subpixels may be 10 μm or less, and specifically, it may be 8 μm, 7.4 μm, 6.4 μm, etc.

[0120] Pixels can take on known arrangements in a plan view. For example, they may be in a stripe arrangement, delta arrangement, pentile arrangement, or Bayer arrangement. The shape of subpixels in a plan view may be any known shape. For example, rectangles, rhombuses, hexagons, etc. Of course, even if it is not a precise shape, if it is close to a rectangle, it is included in the category of rectangles. The shape of subpixels and the pixel arrangement can be used in combination.

[0121] <Applications of organic light-emitting diodes> The organic light-emitting element according to this embodiment can be used as a component of a display device or lighting device. Other applications include exposure light sources for electrophotographic image forming apparatuses, backlights for liquid crystal display devices, and light-emitting devices with a color filter in a white light source.

[0122] The display device may be an image information processing device having an image input unit for inputting image information from an area CCD, linear CCD, memory card, etc., an information processing unit for processing the input information, and a display unit for displaying the input image. The display device may have a plurality of pixels, and at least one of the plurality of pixels may have an organic light-emitting element of this embodiment and an active element such as a transistor connected to the organic light-emitting element. In this case, the substrate is a semiconductor substrate such as silicon, and the transistor may be a MOSFET formed on the substrate. The image display device has an input unit for inputting image information and a display unit for outputting an image, and the display unit has the display device of this embodiment.

[0123] Furthermore, the display unit of the imaging device or inkjet printer may have a touch panel function. The driving method for this touch panel function may be infrared, capacitive, resistive, or electromagnetic induction, and is not particularly limited. The display device may also be used as the display unit of a multifunction printer.

[0124] Next, a display device according to this embodiment will be described with reference to the drawings. Figure 3 is a schematic cross-sectional view showing an example of a display device having an organic light-emitting element and a transistor connected to the organic light-emitting element. The transistor is an example of an active element. The transistor may be a thin-film transistor (TFT).

[0125] Figure 3(a) is a schematic cross-sectional view of an example of a pixel, which is a component of the display device according to this embodiment. The pixel has sub-pixels 10. The sub-pixels are divided into 10R, 10G, and 10B based on their light emission. The emitted color may be distinguished by the wavelength emitted from the light-emitting layer, or the light emitted from the sub-pixel may be selectively transmitted or color-converted by a color filter or the like. Each sub-pixel 10 has a reflective electrode which is a first electrode 2 on an interlayer insulating layer 1, an insulating layer 3 covering the end of the first electrode 2, an organic compound layer 4 covering the first electrode 2 and the insulating layer 3, a transparent electrode which is a second electrode 5, a protective layer 6, and a color filter 7.

[0126] The interlayer insulating layer 1 may have transistors and capacitive elements placed in the layer below or inside it. The transistor and the first electrode 2 may be electrically connected via a contact hole or the like (not shown).

[0127] The insulating layer 3 is also called a bank or pixel isolation layer. It covers the edge of the first electrode 2 and surrounds the first electrode 2. The portion not covered by the insulating layer 3 is in contact with the organic compound layer 4 and becomes the light-emitting region.

[0128] The organic compound layer 4 includes a hole injection layer 41, a hole transport layer 42, a light-emitting layer 43, a hole blocking layer 44, and an electron transport layer 45.

[0129] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0130] The protective layer 6 reduces the penetration of moisture into the organic compound layer 4. Although the protective layer 6 is shown as a single layer, it may consist of multiple layers. Each layer may contain an inorganic compound layer and an organic compound layer.

[0131] The color filter 7 is classified into 7R, 7G, and 7B according to its color. The color filter 7 may be formed on a planarization film (not shown). The color filter 7 may also have a resin protective layer (not shown). Alternatively, the color filter 7 may be formed on a protective layer 6. Or it may be bonded to an opposing substrate such as a glass substrate after being placed on it.

[0132] The display device 100 in Figure 3(b) includes an organic light-emitting element 26 and a TFT 18, which is an example of a transistor. A substrate 11 made of glass, silicon, or the like is provided, with an insulating layer 12 on top of it. An active element such as the TFT 18 is placed on the insulating layer 12, and the active element has a gate electrode 13, a gate insulating film 14, and a semiconductor layer 15. The TFT 18 has a drain electrode 16 and a source electrode 17. An insulating film 19 is provided on top of the TFT 18. The anode 21 and the source electrode 17 constituting the organic light-emitting element 26 are connected via a contact hole 20 provided in the insulating film 19.

[0133] Furthermore, the method of electrical connection between the electrodes (anode 21, cathode 23) included in the organic light-emitting element 26 and the electrodes (source electrode 17, drain electrode 16) included in the TFT 18 is not limited to the configuration shown in Figure 3(b). In other words, it is sufficient if either the anode 21 or the cathode 23 is electrically connected to either the source electrode 17 or the drain electrode 16 of the TFT 18.

[0134] In the display device 100 shown in Figure 3(b), the organic compound layer 22 is depicted as a single layer, but the organic compound layer 22 may consist of multiple layers. A first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce the degradation of the organic light-emitting element 26.

[0135] In the display device 100 shown in Figure 3(b), a transistor is used as the switching element, but other switching elements such as MIM elements may be used instead.

[0136] Furthermore, the transistor used in the display device 100 in Figure 3(b) is not limited to a thin-film transistor having an active layer on the insulating surface of the substrate, but may also be a transistor using a single-crystal silicon wafer. Examples of the active layer include non-single-crystal silicon such as single-crystal silicon, amorphous silicon, and microcrystalline silicon, and non-single-crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Thin-film transistors are also called TFT elements.

[0137] The transistors included in the display device 100 in Figure 3(b) may be formed within a substrate such as a Si substrate. Here, "formed within a substrate" means that the transistors are manufactured by processing the substrate itself, such as a Si substrate. In other words, having transistors within a substrate can be seen as the substrate and transistors being formed as a single unit.

[0138] The organic light-emitting element according to this embodiment has its luminescence controlled by a TFT, which is an example of a switching element, and by providing multiple organic light-emitting elements on the surface, an image can be displayed using the luminescence of each element. The switching element according to this embodiment is not limited to a TFT, but may also be a transistor made of low-temperature polysilicon, or an active matrix driver formed on a substrate such as a Si substrate. "On the substrate" can also mean "within the substrate." Whether to provide a transistor within the substrate or to use a TFT is selected depending on the size of the display area; for example, if the size is about 0.5 inches, it is preferable to provide the organic light-emitting element on a Si substrate.

[0139] Figure 4 is a schematic diagram showing an example of a display device according to this embodiment. The display device 1000 may have a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. Flexible printed circuits FPCs 1002 and 1004 are connected to the touch panel 1003 and the display panel 1005. Transistors are printed on the circuit board 1007. The battery 1008 does not need to be provided if the display device is not a portable device, or it may be provided in a different location even if it is a portable device.

[0140] The display device according to this embodiment may have a color filter having red, green, and blue colors. The color filter may have the red, green, and blue colors arranged in a delta array.

[0141] The display device according to this embodiment may be used in the display unit of a mobile terminal. In that case, it may have both display and operation functions. Examples of mobile terminals include smartphones and other mobile phones, tablets, and head-mounted displays.

[0142] The display device according to this embodiment may be used in the display unit of an imaging device having an optical unit with multiple lenses and an image sensor that receives light that has passed through the optical unit. The imaging device may have a display unit that displays information acquired by the image sensor. Furthermore, the display unit may be a display unit exposed to the outside of the imaging device or a display unit located inside the viewfinder. The imaging device may be a digital camera or a digital video camera.

[0143] Figure 5(a) is a schematic diagram showing an example of an imaging device according to this embodiment. The imaging device 1100 may include a viewfinder 1101, a rear display 1102, an operation unit 1103, and a housing 1104. The viewfinder 1101 may have a display device according to this embodiment. In that case, the display device may display not only the image to be captured, but also environmental information, imaging instructions, etc. Environmental information may include the intensity of ambient light, the direction of ambient light, the speed at which the subject is moving, the possibility of the subject being obscured by an obstacle, etc.

[0144] Since the optimal timing for imaging is very short, it is best to display the information as quickly as possible. Therefore, it is preferable to use a display device using the organic light-emitting element of this embodiment, because organic light-emitting elements have a fast response speed. Display devices using organic light-emitting elements can be used more suitably than liquid crystal display devices, which require a fast display speed.

[0145] The imaging device 1100 has an optical section (not shown). The optical section has multiple lenses that form an image on the image sensor housed in the housing 1104. The focus can be adjusted by adjusting the relative positions of the multiple lenses. This operation can also be performed automatically. The imaging device may also be called a photoelectric converter. The photoelectric converter may not capture images sequentially, but may include imaging methods such as detecting the difference from the previous image or extracting from an image that is always being recorded.

[0146] Figure 5(b) is a schematic diagram showing an example of an electronic device according to this embodiment. The electronic device 1200 has a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may have a circuit, a printed circuit board having the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a touch panel type response unit. The operation unit 1202 may also be a biometric recognition unit that recognizes a fingerprint to unlock or otherwise perform actions. An electronic device having a communication unit can also be called a communication device. The electronic device 1200 may further have a camera function by including a lens and an image sensor. Images captured by the camera function are displayed on the display unit 1201. Examples of the electronic device 1200 include smartphones and laptop computers.

[0147] Figure 6 is a schematic diagram showing an example of a display device according to this embodiment. Figure 6(a) is a display device such as a television monitor or a PC monitor. The display device 1300 has a frame 1301 and a display unit 1302. The display unit 1302 may use a light-emitting element according to this embodiment. The display device 1300 has a frame 1301 and a base 1303 that supports the display unit 1302. The base 1303 is not limited to the form shown in Figure 6(a). The lower edge of the frame 1301 may also serve as the base. In addition, the frame 1301 and the display unit 1302 may be curved. The radius of curvature may be 5000 mm or more and 6000 mm or less.

[0148] Figure 6(b) is a schematic diagram showing another example of the display device according to this embodiment. The display device 1310 in Figure 6(b) is configured to be foldable and is a so-called foldable display device. The display device 1310 has a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may have light-emitting elements according to this embodiment. The first display unit 1311 and the second display unit 1312 may be a single display device without seams. The first display unit 1311 and the second display unit 1312 can be separated by a bending point. The first display unit 1311 and the second display unit 1312 may each display different images, or the first and second display units may together display a single image.

[0149] Figure 7(a) is a schematic diagram showing an example of a lighting device according to this embodiment. The lighting device 1400 may include a housing 1401, a light source 1402, a circuit board 1403, and an optical filter 1404 and a light diffusion unit 1405 that transmit light emitted from the light source 1402. The light source 1402 may have an organic light-emitting element according to this embodiment. The optical filter 1404 may be a filter that improves the color rendering of the light source. The light diffusion unit 1405 can effectively diffuse the light from the light source, such as for lighting up, and deliver light over a wide area. The optical filter 1404 and the light diffusion unit 1405 may be provided on the light-emitting side of the lighting. A cover may be provided on the outermost part as needed.

[0150] The lighting device is, for example, a device for illuminating a room. The lighting device may emit white light, daylight white light, or any other color from blue to red. It may have a dimming circuit to adjust the brightness and a color tuning circuit to adjust the color of the emitted light. The lighting device may have the organic light-emitting element of this embodiment and a power supply circuit connected thereto. The power supply circuit is a circuit that converts AC voltage to DC voltage. The lighting device may have an inverter circuit. Also, white has a color temperature of 4200K and daylight white has a color temperature of 5000K. The lighting device may have a color filter.

[0151] Furthermore, the lighting device according to this embodiment may have a heat dissipation section. The heat dissipation section releases heat from inside the device to the outside, and examples include metals with high specific heat, liquid silicon, etc.

[0152] Figure 7(b) is a schematic diagram of an automobile, which is an example of a mobile body according to this embodiment. The automobile has a taillight, which is an example of a lighting device. The automobile 1500 has a taillight 1501, and may be configured to illuminate when the brakes are applied or the like.

[0153] The taillight 1501 may have an organic light-emitting element according to this embodiment. The taillight 1501 may have a protective member to protect the organic light-emitting element. The protective member has a reasonably high strength and can be made of any transparent material, but it is preferably made of polycarbonate or the like. A frangic acid derivative, an acrylonitrile derivative, or the like may be mixed with the polycarbonate.

[0154] The automobile 1500 may have a body 1503 and windows 1502 attached thereto. The windows 1502 may be transparent displays, unless they are windows for checking the front and rear of the automobile. The transparent displays may have organic light-emitting elements according to this embodiment. In this case, the constituent materials such as electrodes of the organic light-emitting element are made of transparent members.

[0155] The mobile body according to this embodiment may be a ship, aircraft, drone, etc. The mobile body may have a body and a lighting device provided on the body. The lighting device may emit light to indicate the position of the body. The lighting device has an organic light-emitting element according to this embodiment.

[0156] Referencing Figure 8, examples of applications of the display devices of each embodiment described above will be explained. The display device can be applied to systems that can be worn as wearable devices, such as smart glasses, HMDs, and smart contact lenses. The imaging display device used in such applications comprises an imaging device capable of photoelectric conversion of visible light and a display device capable of emitting visible light.

[0157] Figure 8(a) is a schematic diagram showing an example of a wearable device according to one embodiment of the present invention. Using Figure 8(a), we will explain a pair of glasses 1600 (smart glasses) according to one application example. An imaging device 1602, such as a CMOS sensor or SPAD, is provided on the front surface side of the lens 1601 of the glasses 1600. In addition, the display devices of each embodiment described above are provided on the back surface side of the lens 1601.

[0158] The eyeglasses 1600 further include a control device 1603. The control device 1603 functions as a power supply that provides power to the imaging device 1602 and the display device. The control device 1603 also controls the operation of the imaging device 1602 and the display device. The lens 1601 has an optical system formed therein for focusing light onto the imaging device 1602.

[0159] Figure 8(b) is a schematic diagram showing another example of a wearable device according to one embodiment of the present invention. Using Figure 8(b), we will describe a pair of glasses 1610 (smart glasses) according to one application example. The glasses 1610 have a control device 1612, which is equipped with an imaging device corresponding to the imaging device 1602 in Figure 8(a) and a display device. The lens 1611 has an optical system formed therein for projecting light emitted from the imaging device and the display device in the control device 1612, and an image is projected onto the lens 1611. The control device 1612 functions as a power supply that supplies power to the imaging device and the display device, and also controls the operation of the imaging device and the display device.

[0160] The control device 1612 may have a gaze detection unit that detects the wearer's gaze. Gaze detection may use infrared light. The infrared light emitter emits infrared light towards the user's eyeball that is fixated on the displayed image. An imaging unit having a photodetector detects the reflected light from the eyeball of the emitted infrared light, thereby obtaining an image of the eyeball. By having a reduction means that reduces the light from the infrared light emitter to the display unit in a planar view, the degradation of image quality is reduced. The user's gaze toward the displayed image is detected from the image of the eyeball obtained by imaging with infrared light. Any known method can be applied to gaze detection using the image of the eyeball. As an example, a gaze detection method based on the Purkinje image obtained by the reflection of irradiated light from the cornea can be used. More specifically, gaze detection processing based on the pupil-corneal reflection method is performed. Using the pupil-corneal reflection method, the user's gaze is detected by calculating a gaze vector representing the orientation (rotation angle) of the eyeball based on the pupil image and Purkinje image included in the image of the eyeball.

[0161] A display device according to one embodiment of the present invention has an imaging device having a light-receiving element, and may control the display image of the display device based on the user's gaze information from the imaging device. Specifically, the display device determines a first display area that the user is fixated on and a second display area other than the first display area based on the gaze information. The first display area and the second display area may be determined by the control device of the display device, or they may be determined by an external control device and received. In the display area of ​​the display device, the display resolution of the first display area may be controlled to be higher than the display resolution of the second display area. In other words, the resolution of the second display area may be lower than that of the first display area.

[0162] Furthermore, the display area has a first display area and a second display area different from the first display area, and based on gaze information, a higher priority area is determined from the first and second display areas. The first and second display areas may be determined by the control device of the display device, or they may be determined by an external control device and received. The resolution of the higher priority area may be controlled to be higher than the resolution of the areas other than the higher priority area. In other words, the resolution of areas with relatively lower priority may be set lower.

[0163] AI may be used to determine the primary field of view and high-priority areas. The AI ​​may be a model configured to estimate the angle of gaze and the distance to the target object at the end of the line of sight from the image of the eye, using the image of the eye and the direction the eye was actually looking in that image as training data. The AI ​​program may be installed in the display device, the imaging device, or an external device. If installed in an external device, it will be transmitted to the display device via communication.

[0164] When display control is based on visual detection, this method is preferably applicable to smart glasses that further include an imaging device for capturing images of the surrounding environment. The smart glasses can display the captured external information in real time.

[0165] Figure 9(a) is a schematic diagram showing an example of an image forming apparatus according to one embodiment of the present invention. The image forming apparatus 40 is an electrophotographic image forming apparatus and includes a photoreceptor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transfer unit 32, a transport roller 33, and a fuser 35. Light 29 is irradiated from the exposure light source 28, and an electrostatic latent image is formed on the surface of the photoreceptor 27. This exposure light source 28 has an organic light-emitting element according to this embodiment. The developing unit 31 has toner or the like. The charging unit 30 charges the photoreceptor 27. The transfer unit 32 transfers the developed image to a recording medium 34. The transport roller 33 transports the recording medium 34. The recording medium 34 is, for example, paper. The fuser 35 fixes the image formed on the recording medium 34.

[0166] Figures 9(b) and 9(c) are diagrams showing the exposure light source 28, schematic diagrams showing how multiple light-emitting units 36 are arranged on a long substrate. The arrow 37 is parallel to the axis of the photoreceptor and represents the column direction in which the organic light-emitting elements are arranged. This column direction is the same as the direction of the axis in which the photoreceptor 27 rotates. This direction can also be called the long axis direction of the photoreceptor 27. Figure 9(b) shows a configuration in which the light-emitting units 36 are arranged along the long axis direction of the photoreceptor 27. Figure 9(c) is a different configuration from Figure 9(b), in which the light-emitting units 36 are arranged alternately in the column direction in the first and second columns, respectively. The first and second columns are located at different positions in the row direction. In the first column, multiple light-emitting units 36 are arranged with intervals between them. In the second column, light-emitting units 36 are located at positions corresponding to the intervals between the light-emitting units 36 in the first column. That is, multiple light-emitting units 36 are also arranged with intervals between them in the row direction. The arrangement in Figure 9(c) can also be described as a grid pattern, a houndstooth pattern, or a checkerboard pattern.

[0167] As described above, by using the device employing the organic light-emitting element according to this embodiment, stable display with good image quality is possible even during long-term display. Furthermore, by using the device employing the organic light-emitting element according to this embodiment, it is possible to achieve both good visibility outdoors due to high-efficiency, high-brightness light output and power-saving display.

[0168] (3) Ink composition Next, an ink composition according to one embodiment of the present invention will be described. The ink composition of this embodiment contains at least one of the organic compounds of this embodiment described above.

[0169] The organic compound of this embodiment has good solubility in organic solvents and can therefore be used as an ink composition. Furthermore, by using the ink composition of this embodiment, the organic compound layer constituting the organic light-emitting element of this embodiment, particularly the light-emitting layer, can be fabricated by a coating method, making it possible to easily manufacture large-area elements at a relatively low cost.

[0170] Examples of solvents for dissolving the organic compounds in this embodiment include toluene, xylene, mesitylene, dioxane, methylnaphthalene, tetrahydrofuran, diglycreme, 1,2-dichlorobenzene, and 1,2-dichloropropane. These organic solvents can be used individually or in combination of two or more. Among these, it is preferable to use an organic solvent with a suitable evaporation rate, specifically one with a boiling point of about 70°C to 200°C, as this makes it easier to obtain a thin film with a uniform thickness.

[0171] Furthermore, the ink composition of this embodiment may also contain other additive compounds. Examples of additive compounds include the above-mentioned known light-emitting layer host or light-emitting assist material, hole transport material, light-emitting material, electron transport material, etc.

[0172] The concentration of the organic compound of this embodiment in the ink composition is preferably 0.05% by mass or more and 20% by mass or less, and more preferably 0.1% by mass or more and 5% by mass or less, relative to the entire composition.

[0173] The ink composition of the present embodiment can form a film by a spin coating method, a bar coating method, a slit coating method, an inkjet method, a nozzle coating method, a casting method, a gravure printing method, or the like. The organic light-emitting device of the present embodiment can construct a display apparatus such as a display by forming a layer containing the organic compound of the present embodiment on an electrode formed in a pixel pattern.

Examples

[0174] «Synthesis of Compounds» The following compounds were synthesized. Comp.1, Comp.2, Comp.3, and Comp.E are respectively the aforementioned Comp.1(Te), Comp.24(Te), Comp.7(Te), and Comp.A(Te).

[0175]

Chemical Formula

[0176] <Synthesis of Comp.1>

Chemical Formula

[0177] (1) Synthesis of 4'-bromo-3'-fluoro-2-iodo-1,1'-biphenyl (Compound 1) In a 500 mL Schlenk tube, 1-bromo-2-fluoro-4-iodobenzene (11.7 g, 39 mmol), 2-iodophenylboronic acid (7.43 g, 30 mmol), K2CO3 (12.4 g, 90 mmol), toluene (100 mL), EtOH (50 mL), and water (50 mL) were added and the mixture was stirred for 20 minutes while bubbling with nitrogen gas. Tetrakis(triphenylphosphine)palladium(0) (1.73 g, 1.5 mmol) was added and the mixture was stirred under reflux at 90°C for 17 hours. After cooling to room temperature, water was added to the reaction solution, and the mixture was extracted with toluene. The organic layer was washed with water. The organic layer was dried with Na2SO4, the Na2SO4 hydrate was collected by filtration, the filtrate was recovered, and the solvent was removed by vacuum distillation. The crude product obtained was purified by silica gel chromatography (eluent: hexane) to obtain compound 1 as a white solid (yield: 10.5 g, yield: 93%).

[0178] 1 H NMR(400MHz, CDCl3): δ7.96(dd,J=8.0,1.0Hz,1H),7.62-7.58(m,1H),7.40(td,J=7.5,1.3H z,1H),7.28-7.25(m,1H),7.12(dd,J=9.3,2.0Hz,1H),7.09-7.04(m,1H),7.03-7.00(m,1H).

[0179] (2) Synthesis of 3-bromo-2-fluorodibenzo[b,d]iodol-5-ium trifluoromethanesulfonate (compound 2) Compound 1 (10.2 g, 27 mmol) and anhydrous CH2Cl2 (135 mL) were added to a 500 mL Schlenk tube, and the mixture was stirred at 0°C for 20 minutes and then cooled. 3-Chloroperoxybenzoic Acid (contains ca. 30% water) (9.37 g, 38 mmol) was added, and the mixture was stirred at 0°C for 10 minutes. Then, TfOH (10.2 g, 68 mmol) was added dropwise, and the mixture was stirred at room temperature for 1 hour. Diethyl ether was added to the reaction solution, and the precipitate was filtered off to obtain Compound 2 as a white solid (yield: 13.1 g, yield: 92%).

[0180] 1 H NMR(400MHz,DMSO-d6):δ8.65(d,J=10.0Hz,1H),8.54(dd,J=8.0,1.3Hz,1H),8.4 5-8.40(m,1H),8.22(dd,J=8.3,1.0Hz,1H),7.91-7.87(m,1H),7.79-7.75(m,1H).

[0181] (3) Synthesis of 3-bromo-2-fluorodibenzo[b,d]tellurophene (compound 3) Compound 2 (12.6 g, 24 mmol), TBAB (23.2 g, 72 mmol), Te (15.3 g, 120 mmol), anhydrous DMSO (37 mL), and 2-methylpyridine (19 mL) were placed in a 100 mL Schlenk tube and vigorously stirred under nitrogen at 120 °C for 14 hours. After cooling to room temperature, water was added to the reaction solution and filtered by Celite filtration. The filtrate was washed with water, the remaining filtrate was eluted with CH2Cl2, the filtrate was collected, and the solvent was removed by vacuum distillation. The resulting crude product was purified by silica gel chromatography (eluent: hexane) to obtain compound 3 as a pale yellow solid (yield: 3.47 g, yield: 38%).

[0182] 1 H NMR (400MHz, CDCl3) δ8.01-7.99(m,2H),7.88-7.81(m,2H),7.49-7.45(m,1H),7.37-7.33(m,1H).

[0183] (4) Synthesis of 9-(3-bromodibenzo[b,d]tellurophen-2-yl)-9H-carbazole (compound 4) To a 300 mL Schlenk tube were added carbazole (2.01 g, 12 mmol), Cs₂CO₃ (4.43 g, 14 mmol), dehydrated DMF (80 mL), and Compound 3 (3.01 g, 8.0 mmol), and the mixture was stirred at 150°C for 13 hours under nitrogen. After allowing the mixture to cool to room temperature, water was added to the reaction solution, and celite filtration was performed. The residue on the filter was washed with water, the remaining residue was eluted with CHCl₃, the filtrate was collected, and the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel chromatography (developing solvent: CH₂Cl₂ / hexane = 1 / 4, v / v), and further purified by recycling preparative GPC to obtain 4 as a pale yellow solid (yield: 2.65 g, 63%).

[0184] 1 ¹H NMR (400 MHz, CDCl₃) δ 8.34 (s, 1H), 8.19 (dt, J=7.8, 0.9 Hz, 2H), 8.16 (s, 1H), 7.96-7.90 (m, 2H), 7.44-7.30 (m, 6H), 7.12 (d, J=8.0 Hz, 2H).

[0185] (5) Synthesis of 9-(3-(dimesitylboraneyl)dibenzo[b,d]tellurophen-2-yl)-9H-carbazole (Comp.1) To a 200 mL Schlenk tube were added Compound 4 (1.31 g, 2.5 mmol) and dehydrated toluene (50 mL), and the mixture was stirred and cooled at -10°C for 30 minutes under nitrogen. n-BuLi (1.55 M in hexane, 1.69 mL, 2.6 mmol) was added dropwise, and the mixture was stirred at 0°C for 1 hour. Dimesitylfluoroborane (2.04 g, 8.0 mmol) was added, and the mixture was stirred at 60°C for 11 hours. After allowing the mixture to cool to room temperature, water was added to the reaction solution, the mixture was extracted with toluene, and the organic layer was washed with water. The organic layer was dried over Na₂SO₄, the hydrate of Na₂SO₄ was removed by filtration, the filtrate was collected, and the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel chromatography (developing solvent: CH₂Cl₂ / hexane = 1 / 7, v / v), and further purified by recycling preparative GPC to obtain Comp.1 as a yellow solid (yield: 0.70 g, 40%).

[0186] 1 1H NMR (400 MHz, DMSO-d6) δ 8.43 (d, J=6.3 Hz, 2H), 8.37-8.34 (m, 1H), 8.21-8.19 (m, 1H), 7.89 (s, 2H), 7.42-7.34 (m, 2H), 7.24 (t, J=7.5 Hz, 2H), 7.14-7.07 (m, 4H), 5.34-7.01 (m, 4H), 0.27-2.42 (m, 18H). MS (MALDI-TOF): m / z calcd 695.20 [M] + ; found 695.43.

[0187] <Synthesis of Comp. 2 and Comp. 3>

Chem.

[0188] (1) Synthesis of 4'-bromo-3',5'-difluoro-2-iodo-1,1'-biphenyl (Compound 6) A 1 L three-neck round-bottom flask was charged with 2-bromo-1,3-difluoro-5-iodobenzene (15.6 g, 49 mmol), 2-iodophenylboronic acid (8.67 g, 35 mmol), K2CO3 (14.5 g, 105 mmol), toluene (140 mL), EtOH (70 mL), and water (70 mL), and the mixture was stirred for 30 minutes while bubbling with nitrogen gas. Tetrakis(triphenylphosphine)palladium(0) (2.02 g, 1.8 mmol) was added, and the mixture was stirred for 17 hours under reflux at 90°C. After allowing to cool to room temperature, water was added to the reaction solution, the mixture was extracted with toluene, and the organic layer was washed with water. The organic layer was dried over Na2SO4, the hydrate of Na2SO4 was collected by filtration, the filtrate was recovered, and the solvent was distilled off under reduced pressure. The obtained crude product was purified by silica gel chromatography (developing solvent: hexane) to obtain Compound 6 as a white solid (yield: 12.8 g, yield rate: 93%).

[0189] 1H NMR (400MHz, CDCl3): δ7.96(dd,J=8.0,1.0Hz,1H),7.43-7.39(m,1H),7.27-7.25(dd,J=7.6,1.6Hz,1H),7.11-7.06(m,1H),6.97-6.93(m,2H).

[0190] (2) Synthesis of 3-bromo-2,4-difluorodibenzo[b,d]iodol-5-ium trifluoromethanesulfonate (compound 7) Compound 6 (11.1 g, 28 mmol) and anhydrous CH2Cl2 (140 mL) were added to a 500 mL Schlenk tube, and the mixture was stirred at 0°C for 20 minutes and then cooled. 3-Chloroperoxybenzoic Acid (contains ca. 30% water) (9.66 g, 39 mmol) was added, and the mixture was stirred at 0°C for 10 minutes. Then, TfOH (10.6 g, 71 mmol) was added dropwise, and the mixture was stirred at room temperature for 1 hour. Diethyl ether was added to the reaction solution, and the precipitate was filtered off to obtain compound 7 as a white solid (yield: 11.3 g, yield: 74%).

[0191] 1 H NMR (400MHz, DMSO-d6): δ8.51-8.45(m,2H),8.27-8.24(m,1H),7.91-7.87(m,1H),7.80-7.76(m,1H).

[0192] (3) Synthesis of 3-bromo-2,4-difluorodibenzo[b,d]tellurophene (compound 8) Compound 7 (10.9 g, 20 mmol), TBAB (19.4 g, 60 mmol), Te (12.8 g, 100 mmol), anhydrous DMSO (31 mL), and 2-methylpyridine (16 mL) were placed in a 100 mL Schlenk tube and vigorously stirred under nitrogen at 120 °C for 14 hours. After cooling to room temperature, water was added to the reaction solution and filtered by Celite filtration. The filtrate was washed with water, the remaining filtrate was eluted with CH2Cl2, the filtrate was collected, and the solvent was removed by vacuum distillation. The resulting crude product was purified by silica gel chromatography (eluent: hexane) and further purified by recycled preparative GPC to obtain compound 8 as a pale yellow solid (yield: 2.85 g, yield: 36%).

[0193] 1 H NMR(400MHz,CDCl3)δ8.01-7.99(m,1H),7.88(dt,J=7.8,0.5Hz,1H),7.68(dd,J=9.0,1.0Hz,1H),7.51-7.47(m,1H),7.40-7.36(m,1H).

[0194] (4) Synthesis of 5,5'-(3-bromodibenzo[b,d]tellurophene-2,4-diyl)bis(5H-pyrido[4,3-b]indole) (compound 9) 5H-Pyrido[4,3-b]indole (0.81 g, 4.8 mmol), Cs2CO3 (1.8 g, 5.5 mmol), anhydrous DMF (20 mL), and compound 8 (0.79 g, 2.0 mmol) were added to a 100 mL Schlenk tube and stirred at 100 °C under nitrogen for 17 hours. After cooling to room temperature, water was added to the reaction solution and the precipitate was filtered. The filtrate was washed with water, the remaining filtrate was eluted with CHCl3, the filtrate was collected, and the solvent was removed by vacuum distillation. The resulting crude product was purified by silica gel chromatography (eluent: CH2Cl2 / MeOH = 20 / 1, v / v) to obtain compound 9 as a light brown solid (yield: 0.18 g, yield: 13%).

[0195] 1 H NMR(400MHz,DMSO-d6)δ9.52(dd,J=14.1,1.0Hz,2H),8.93(s,1H),8.54-8.49(m,3H),8.43-8.38(m,2H),8.15-8.13(m,1H),7.58-7.39(m,10H).

[0196] (5) Synthesis of 5,5'-(3-(dimesitylboraneyl)dibenzo[b,d]tellurophene-2,4-diyl)bis(5H-pyrido[4,3-b]indole) (Comp.2)

[0197] Compound 9 (0.14 g, 0.20 mmol) and anhydrous toluene (5 mL) were added to a 50 mL Schlenk tube, and the mixture was stirred under nitrogen at -10°C for 30 minutes and then cooled. n-BuLi (1.6 M, 0.13 mL, 0.21 mmol) was added dropwise, and the mixture was stirred at 0°C for 1 hour. Dimesitylfluoroborane (0.16 g, 0.62 mmol) was added, and the mixture was stirred at 60°C for 11 hours. After cooling to room temperature, water was added to the reaction solution, and the mixture was extracted with CH2Cl2. The organic layer was washed with water. The organic layer was dried with Na2SO4, the Na2SO4 hydrate was collected by filtration, the filtrate was recovered, and the solvent was removed by vacuum distillation. The resulting crude product was purified by silica gel column chromatography (eluent: CH2Cl2 / MeOH = 20 / 1, v / v) to obtain Comp.2 as a yellow solid (yield: 7.4 mg, yield: 4.3%).

[0198] MS(MALDI-TOF):m / z calcd 862.25 [M+H] + ;found 863.17.

[0199] (6) Synthesis of 9,9'-(3-bromodibenzo[b,d]tellurophene-2,4-diyl)bis(9H-carbazole) (compound 10) In a 100 mL Schlenk tube, carbazole (2.3 g, 14 mmol), Cs2CO3 (6.0 g, 18 mmol), anhydrous DMF (20 mL), and compound 8 (1.7 g, 4.9 mmol) were added and stirred under nitrogen at 140 °C for 14 hours. After cooling to room temperature, water was added to the reaction solution and the precipitate was filtered. The filtrate was washed with water and MeOH, and the resulting crude product was purified by silica gel chromatography (developing solvent: CH2Cl2 / hexane = 1 / 4, v / v) to obtain pale yellow solid compound 10 (yield 2.9 g, yield 86%).

[0200] 1 H NMR(400MHz,CDCl3)δ8.35(s,1H),8.20(d,J=8.0Hz,4H),8.07(d,J=8.8Hz,1H) ,7.83(d,J=8.8Hz,1H),7.49-7.44(m,5H),7.39-7.32(m,5H),7.24-7.19(m,4H)

[0201] (7) Synthesis of 9,9'-(3-(dimesitylboraneyl)dibenzo[b,d]tellurophene-2,4-diyl)bis(9H-carbazole) (Comp.3) A 100 mL Schlenk tube was purged with nitrogen, compound 10 (1.0 g, 1.5 mmol) and anhydrous toluene (30 mL) were added, and n-BuLi (2.6 M, 0.60 mL, 1.6 mmol) was added dropwise. The mixture was stirred at 60°C for 1 hour. The mixture was cooled to 0°C, dimesitylfluoroborane (1.3 g, 4.8 mmol) was added, and the mixture was stirred at 60°C for 14 hours. After cooling to room temperature, water was added to the reaction solution, and the mixture was extracted with toluene. The organic layer was washed with water. The organic layer was dried over Na2SO4, the Na2SO4 hydrate was collected by filtration, the filtrate was recovered, and the solvent was removed by vacuum distillation. The resulting crude product was purified by silica gel column chromatography (eluent: CH2Cl2 / hexane = 1 / 10, v / v) and further purified by recycled preparative GPC to obtain Comp.3 as a yellow solid (yield 0.13 g, yield 10%).

[0202] 1 1H NMR (400 MHz, CDCl3) δ 8.40 (s, 1H), 8.16 (d, J=7.2 Hz, 1H), 7.93 (d, J=7.2 Hz, 2H), 7.86-7.76 (m, 3H), 7.48 (t, J=6.8 Hz, 1H), 7.32-7.15 (m, 13H), 7.14-7.10 (m, 3H), 5.80 (s, 2H), 5.73 (s, 2H), 2.32 (s, 3H), 2.25 (s, 3H), 1.82 (s, 3H), 1.80 (s, 3H), 0.77 (s, 6H). MS (MALDI-TOF): m / z calcd 860.27 [M] + ; found 860.30.

[0203] <Synthesis of Comp. E> Compound E was synthesized according to the synthesis of Compound A described in Patent Document 1.

[0204] ≪ΔE ST [eV] Calculation≫ Comp. 1 to Comp. 3 and Comp. E were each dissolved in toluene at 1.0×10 -5 M concentration, after subjecting the solution to Ar bubbling for 5 minutes, the fluorescence emission spectrum was measured at room temperature (298 K). A tangent line was drawn to the rising edge on the short-wavelength side of the measured fluorescence spectrum, the wavelength λF [nm] at the intersection of the tangent line and the horizontal axis was determined, and the excited singlet energy level S1 [eV] was calculated from the formula: Excited singlet energy level [eV] = 1239.85 / λF. A sample prepared in the same manner was cooled to 77 K, and the phosphorescence emission spectrum observed after blocking excitation light was measured. A tangent line was drawn to the rising edge on the short-wavelength side of the measured phosphorescence spectrum, the wavelength λP [nm] at the intersection of the tangent line and the horizontal axis was determined, and the excited triplet energy level T1 [eV] was calculated from the formula: Excited triplet energy level [eV] = 1239.85 / λP.

[0205] ΔE was calculated from S1 and T1 measured as described above. ST [eV]. The results are shown in Table 3.

[0206] [Table 3]

[0207] From Table 3, Comp. 1 to 3, which are the compounds of the present example, have ΔE ST small. ΔE ST of the compounds of the present example is smaller than that of Comp. E, that is, it is better to arrange a donor and an acceptor on one benzene ring of dibenzotellurophene.

[0208] ≪Included Configurations≫ The disclosure of the present embodiment includes the following configurations. (Configuration 1) An organic compound represented by the general formula (1). In general formula (1), R1 to R4 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted silyl group, and a group represented by general formula (3). Provided that at least one of R1 to R4 is a group represented by general formula (2), and at least one of R1 to R4 is a group represented by general formula (3). R5 to R8 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a substituted silyl group. E is selected from a sulfur atom, a selenium atom, and a tellurium atom. In general formula (2), each R9 is independently selected from a hydrogen atom and a substituted or unsubstituted alkyl group. R 10 are each independently selected from substituted or unsubstituted alkyl groups. a represents a bonding position. In general formula (3), X1 to X4 are each independently selected from N and CR 11 . R 11 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted silyl group, and a cyano group. When there are a plurality of CR 11 , each R 11 may be the same or different. R 15 to R 18 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted silyl group, and a cyano group. R 15 to R 18 two adjacent groups among them may form a group represented by general formula (4). b represents a bonding position. In general formula (4), R 19 to R 22 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a substituted silyl group. Y is selected from an oxygen atom, a sulfur atom, a selenium atom, and a tellurium atom. c represents a bonding position.

[0209] (Configuration 2) The organic compound according to Configuration 1, wherein two adjacent groups among the R1 to R4 are the group represented by the general formula (2) and the group represented by the general formula (3). (Configuration 3) The organic compound according to Configuration 1, wherein a group adjacent to both the group represented by the general formula (2) and the group represented by the general formula (3) among the R1 to R4 is a group other than a hydrogen atom. (Configuration 4) The organic compound according to any one of Configurations 1 to 3, wherein one of the R1 to R4 is the group represented by the general formula (2), and one or two of the R1 to R4 are the group represented by the general formula (3). (Configuration 5) The organic compound according to any one of Configurations 1 to 4, wherein the R5 to R8 are hydrogen atoms. (Configuration 6) The organic compound according to any one of Configurations 1 to 5, wherein E is a tellurium atom. (Configuration 7) The aforementioned R 10 The organic compound according to any one of configurations 1 to 6, characterized in that it is a methyl group or an isopropyl group. (Composition 8) The aforementioned R 11 , R 15 ~R 22 The organic compound according to any one of the configurations 1 to 7, characterized in that it is a hydrogen atom. (Composition 9) The organic compound according to any one of configurations 1 to 8, characterized in that the group represented by the general formula (3) is one of the groups shown in group A. (Composition 10) R1 to R8, R 11 , R 15 ~R 22 The organic compound according to any one of configurations 1 to 9, characterized in that the substituents that may be present are a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 12 carbon atoms, or a substituted silyl group. (Composition 11) R1 to R8, R 11 , R 15 ~R 22 The organic compound according to configuration 10, characterized in that the substituents that may be present are any of the groups shown in group B. In group B, * indicates a bond position.

[0210] (Composition 12) An organic light-emitting element having a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, An organic light-emitting element characterized in that at least one layer of the organic compound layer contains the organic compound described in any of configurations 1 to 11. (Composition 13) The organic light-emitting element according to configuration 12, characterized in that the layer containing the organic compound is a light-emitting layer. (Composition 14) The organic light-emitting element according to configuration 13, characterized in that the light-emitting layer has a second organic compound different from the organic compound. (Composition 15) The organic light-emitting element according to configuration 14, characterized in that the concentration of the organic compound is 0.01% by mass or more and 50% by mass or less relative to the entire light-emitting layer. (Composition 16) The organic light-emitting element according to configuration 15, characterized in that the concentration of the organic compound is 10% by mass or more and 50% by mass or less of the entire light-emitting layer. (Composition 17) The organic light-emitting element according to configuration 14, characterized in that the light-emitting layer has a third organic compound that is different from both the organic compound and the second organic compound. (Composition 18) The organic light-emitting element according to configuration 17, characterized in that the concentration of the organic compound is 1% by mass or more and 50% by mass or less of the entire light-emitting layer. (Composition 19) The organic light-emitting element according to configuration 18, characterized in that the concentration of the organic compound is 10% by mass or more and 50% by mass or less of the entire light-emitting layer.

[0211] (Composition 20) An ink composition characterized by containing an organic compound as described in any of the components 1 to 11. (Composition 21) A display device having a plurality of pixels, wherein at least one of the plurality of pixels has an organic light-emitting element according to any of configurations 12 to 19 and a transistor connected to the organic light-emitting element. (Composition 22) It comprises an optical unit having multiple lenses, an image sensor that receives light that has passed through the optical unit, and a display unit that displays the image captured by the image sensor. The photoelectric conversion device is characterized in that the display unit has an organic light-emitting element as described in any of configurations 12 to 19. (Composition 23) An electronic device comprising: a display unit having an organic light-emitting element as described in any of configurations 12 to 19; a housing on which the display unit is provided; and a communication unit provided in the housing for communicating with the outside. (Composition 24) A lighting device characterized by comprising a light source having an organic light-emitting element as described in any of configurations 12 to 19, and a light-diffusing section or optical filter that transmits the light emitted by the light source. (Composition 25) A mobile body characterized by comprising a lamp having an organic light-emitting element as described in any of configurations 12 to 19, and a body on which the lamp is provided. (Composition 26) An electrophotographic image forming apparatus characterized by having an organic light-emitting element as described in any of configurations 12 to 19. [Explanation of Symbols]

[0212] 1: Interlayer insulating layer, 2: First electrode, 3: Insulating layer, 4: Organic compound layer, 5: Second electrode, 6: 7: Protective layer, 10: Color filter, 11: Sub-pixel, 12: Substrate, 13: Insulating layer, 14: Gate Electrode, 14: Gate insulating film, 15: Semiconductor layer, 16: Drain electrode, 17: Source electrode, 18: TFT, 19: Insulating film, 20: Contact hole, 21: Anode, 22: Organic compound Layer, 23: Cathode, 24: First protective layer, 25: Second protective layer, 26: Organic light-emitting element, 10 0:Display device< / c> < / y> < / e>

Claims

1. An organic compound characterized by being represented by the following general formula (1). 【Chemistry 1】 In general formula (1), R 1 ~R 4 Each of these is independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted silyl group, and a group represented by the following general formula (3). However, R 1 ~R 4 At least one of them is a group represented by the following general formula (2), and R 1 ~R 4 At least one of these is a group represented by the following general formula (3). R 5 ~R 8 Each of these is independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a substituted silyl group. E is selected from sulfur, selenium, and tellurium atoms. 【Chemistry 2】 In general formula (2), R 9 are each independently selected from a hydrogen atom and a substituted or unsubstituted alkyl group. R 10 Each of these is independently selected from substituted or unsubstituted alkyl groups. 'a' indicates the bonding position. 【Transformation 3】 In general formula (3), X 1 ~X 4 These are N and CR, respectively. 11 From there, he was elected independent. R 11 Each of these is independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted silyl group, and a cyano group. CR 11 If there are multiple R 11 They can be the same or different. R 15 ~R 18 Each of these is independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted silyl group, and a cyano group. 15 ~R 18 Two adjacent of these may form a group represented by the following general formula (4). b indicates the bond position. 【Chemistry 4】 In general formula (4), R 19 ~R 22 Each of these is independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a substituted silyl group. Y is selected from oxygen, sulfur, selenium, and tellurium atoms. c indicates the bond position.

2. The aforementioned R 1 ~R 4 The organic compound according to claim 1, characterized in that two adjacent members of the group are a group represented by general formula (2) and a group represented by general formula (3).

3. The aforementioned R 1 ~R 4 The organic compound according to claim 1, characterized in that, among them, the group adjacent to both the group represented by general formula (2) and the group represented by general formula (3) is a group other than a hydrogen atom.

4. The aforementioned R 1 ~R 4 One of them is the group represented by the general formula (2), and R 1 ~R 4 The organic compound according to any one of claims 1 to 3, characterized in that one or two of them are groups represented by the general formula (3).

5. The aforementioned R 5 ~R 8 The organic compound according to any one of claims 1 to 3, characterized in that it is a hydrogen atom.

6. The organic compound according to any one of claims 1 to 3, characterized in that E is a tellurium atom.

7. The aforementioned R 10 The organic compound according to any one of claims 1 to 3, characterized in that it is a methyl group or an isopropyl group.

8. The aforementioned R 11 , R 15 ~R 22 The organic compound according to any one of claims 1 to 3, characterized in that it is a hydrogen atom.

9. The organic compound according to any one of claims 1 to 3, characterized in that the group represented by the general formula (3) is one of the groups shown in group A below. 【Transformation 5】

10. The aforementioned R 1 ~R 8 , R 11 , R 15 ~R 22 The organic compound according to any one of claims 1 to 3, characterized in that the substituents that may be present are a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 12 carbon atoms, or a substituted silyl group.

11. The aforementioned R 1 ~R 8 , R 11 , R 15 ~R 22 The organic compound according to claim 10, characterized in that the substituents that may be present are any of the groups shown in group B below. 【Transformation 6】 In group B, * indicates the binding site.

12. An organic light-emitting element having a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, An organic light-emitting element characterized in that at least one layer of the organic compound layer contains the organic compound described in any one of claims 1 to 3.

13. The organic light-emitting element according to claim 12, characterized in that the layer containing the organic compound is a light-emitting layer.

14. The organic light-emitting element according to claim 13, characterized in that the light-emitting layer has a second organic compound different from the organic compound.

15. The organic light-emitting element according to claim 14, characterized in that the concentration of the organic compound is 0.01% by mass or more and 50% by mass or less with respect to the entire light-emitting layer.

16. The organic light-emitting element according to claim 15, characterized in that the concentration of the organic compound is 10% by mass or more and 50% by mass or less with respect to the entire light-emitting layer.

17. The organic light-emitting element according to claim 14, characterized in that the light-emitting layer has a third organic compound that is different from both the organic compound and the second organic compound.

18. The organic light-emitting element according to claim 17, characterized in that the concentration of the organic compound is 1% by mass or more and 50% by mass or less with respect to the entire light-emitting layer.

19. The organic light-emitting element according to claim 18, characterized in that the concentration of the organic compound is 10% by mass or more and 50% by mass or less with respect to the entire light-emitting layer.

20. An ink composition characterized by containing the organic compound described in any one of claims 1 to 3.

21. A display device having a plurality of pixels, wherein at least one of the plurality of pixels is an organic light-emitting element according to claim 12 and a transistor connected to the organic light-emitting element.

22. It comprises an optical unit having multiple lenses, an image sensor that receives light that has passed through the optical unit, and a display unit that displays the image captured by the image sensor. The photoelectric conversion device is characterized in that the display unit has the organic light-emitting element described in claim 12.

23. An electronic device comprising: a display unit having an organic light-emitting element as described in claim 12; a housing on which the display unit is provided; and a communication unit provided in the housing for communicating with the outside.

24. A lighting device characterized by comprising a light source having an organic light-emitting element as described in claim 12, and a light-diffusing section or optical filter that transmits light emitted by the light source.

25. A mobile body characterized by comprising a lamp having an organic light-emitting element as described in claim 12, and a body on which the lamp is provided.

26. An electrophotographic image forming apparatus characterized by having an organic light-emitting element as described in claim 12.

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