Organic compound and organic light-emitting element

Abstract

The present disclosure provides an organic compound represented by general formula (1-1) or (1-2). In general formulae (1-1) and (1-2), at least four of the bonds Ra to Rh and at least four of the bonds Ri to Rp are bonded to a skeleton selected from Structural Group A, and the bonds of the bonds Ra to Rp that are not bonded to the skeleton in Structural Group A are independently selected from a hydrogen atom or a substituent. In general formulae (2-1) to (2-10), R1 to R90 are independently selected from the group consisting of a hydrogen atom, a deuterium atom, and various substituents. And X is an oxygen atom, a sulfur atom, NR91, CR92R93, or SiR94R95. And R91 to R95 are independently selected from a hydrogen atom or a substituent group. The bonding position represents a bonding position with a bond Ra to Rp. STRUCTURE A SET

Description

Technical Field

[0001] This invention relates to organic compounds and organic light-emitting elements containing such organic compounds. Background Technology

[0002] An organic light-emitting element (hereinafter also referred to as an "organic electroluminescent element" or "organic EL element") is an electronic device comprising a pair of electrodes and an organic compound layer disposed between the electrodes. By injecting electrons and holes into the organic compound layer via the pair of electrodes, excitons of luminescent organic compounds are generated in the organic compound layer, and the organic light-emitting element emits light when the excitons return to their ground state.

[0003] To date, compounds suitable for organic light-emitting elements have been actively developed. Patent document 1 discloses compounds Ref-1 and Ref-2 as compounds having an indole-carbazole skeleton.

[0004] [Chemical Formula 1]

[0005]

[0006] Compound Ref-1 Compound Ref-2

[0007] Existing technical documents

[0008] Patent documents

[0009] Patent Document 1: International Publication No. 2019 / 111971 Summary of the Invention

[0010] The problem the invention aims to solve

[0011] However, each of the above compounds has room for improvement in terms of thermal stability.

[0012] The present invention was made in view of the above-mentioned problems, and its object is to provide an organic compound with high thermal stability.

[0013] Solution for solving the problem

[0014] Organic compounds according to the present invention are represented by general formula (1-1) or (1-2).

[0015] [Chemical Formula 2]

[0016]

[0017] In general formula (1-1), the bonding site R a To R h At least four of the bonds are attached to the backbone selected from structure group A. At the bonding site R... aTo R h In this context, the bonding sites not bonded to structure group A are each independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted silyl group, and cyano group.

[0018] In general formula (1-2), the bonding site R i To R p At least four of the bonds are attached to the backbone selected from structure group A. At the bonding site R... i To R p In this context, the bonding sites not bonded to structure group A are each independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted silyl group, and cyano group.

[0019] [Chemical Formula 3]

[0020] Structure A Group

[0021]

[0022] In general formulas (2-1) to (2-10), R 1 To R 90 Each is independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted silyl and cyano.

[0023] X represents an oxygen atom, a sulfur atom, and NR. 91 CR 92 R 93 or SiR 94 R 95 R 91 To R 95 Each group is independently selected from the following groups: hydrogen atom, deuterium atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group. Bonding position. Indicates bonding to the bonding site R a To R p The location.

[0024] Advantages of the invention

[0025] According to the present invention, an organic compound with high thermal stability can be provided. Attached Figure Description

[0026] [ Figure 1A [Illustrated cross-sectional view] is a schematic cross-sectional view showing an example of a pixel of a display device according to an embodiment of the present invention.

[0027] [ Figure 1B [Illustrated cross-sectional view of an example of a display device including an organic EL element according to an embodiment of the present invention.]

[0028] [ Figure 2 [Illustration] is a schematic diagram illustrating an example of a display device according to an embodiment of the present invention.

[0029] [ Figure 3A [Illustration] is a schematic diagram illustrating an example of a camera device according to an embodiment of the present invention.

[0030] [ Figure 3B [Illustration] is a schematic diagram illustrating an example of an electronic device according to an embodiment of the present invention.

[0031] [ Figure 4A [Illustration] is a schematic diagram illustrating an example of a display device according to an embodiment of the present invention.

[0032] [ Figure 4B [Illustration] is a schematic diagram illustrating an example of a foldable display device.

[0033] [ Figure 5A [Illustration] is a schematic diagram illustrating an example of a lighting device according to an embodiment of the present invention.

[0034] [ Figure 5B [Illustration] is a schematic diagram illustrating an example of a car including vehicle lights according to an embodiment of the present invention.

[0035] [ Figure 6A [Illustration] is a schematic diagram illustrating an example of a wearable device according to one embodiment of the present invention.

[0036] [ Figure 6B [Illustration] is a schematic diagram of an example of a wearable device according to an embodiment of the present invention, the wearable device including a camera device.

[0037] [ Figure 7A [Illustration] is a schematic diagram illustrating an example of an image forming apparatus according to an embodiment of the present invention.

[0038] [ Figure 7B[Illustration] is a schematic diagram illustrating an example of an exposure light source for an image forming apparatus according to an embodiment of the present invention.

[0039] [ Figure 7C [Illustration] is a schematic diagram illustrating an example of an exposure light source for an image forming apparatus according to an embodiment of the present invention.

[0040] [ Figure 8 The crystal structure of intermediate 7 was obtained through single-crystal X-ray structural analysis.

[0041] [ Figure 9 [ ] is the normalized emission spectrum of compound A-7 in toluene solution.

[0042] [ Figure 10 [ ] is the normalized emission spectrum of compound D-1 in toluene solution.

[0043] [ Figure 11 [ ] is the normalized emission spectrum of compound D-2 in toluene solution. Detailed Implementation

[0044] In this specification, examples of halogen atoms include, but are not limited to, fluorine, chlorine, bromine, and iodine atoms.

[0045] Alkyl groups can have 1 to 20 carbon atoms, 1 to 10 carbon atoms, or 1 to 4 carbon atoms. Specific examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, octyl, cyclohexyl, tert-pentyl, 3-methylpent-3-yl, 1-adamantyl, and 2-adamantyl.

[0046] The aryl group can have 6 to 20 carbon atoms or 6 to 12 carbon atoms. Specific examples include, but are not limited to, phenyl, naphthyl, indene, biphenyl, terphenyl, fluorenyl, phenanthrene, triphenylene, pyrene, anthranil group, peryl, chrysenyl group, and fluoranyl.

[0047] Heterocyclic groups can have 3 to 24 carbon atoms, 3 to 18 carbon atoms, or 3 to 12 carbon atoms. Specific examples include, but are not limited to, pyridinyl, pyrazinyl, triazinyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, carbazole, acridineyl, and phenanthrolyl group.

[0048] The amino group can be a substituted amino group that is substituted with an alkyl or aryl group, or a substituted amino group that is substituted with an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 12 carbon atoms. Specific examples include, but are not limited to, N-methylamino, N-ethylamino, N,N-dimethylamino, N,N-diethylamino, N-methyl-N-ethylamino, N-benzylamino, N-methyl-N-benzylamino, N,N-dibenzylamino, aniline, N,N-diphenylamino, N,N-dinaphthylamino, N,N-difluorenylamino, N-phenyl-N-tolylamino, N,N-dimethylmethylamino, N-methyl-N-phenylamino, N,N-dianisolylaminogroup, N-trimethylmethyl-N-phenylamino, N,N-ditrimethylmethylamino, N-phenyl-N-(4-tert-butylphenyl)amino, N-phenyl-N-(4-trifluoromethylphenyl)amino, and N-piperidinyl.

[0049] Alkoxy groups can have 1 to 10 carbon atoms or 1 to 4 carbon atoms. Specific examples include, but are not limited to, methoxy, ethoxy, propoxy, 2-ethyl-octoxy, and benzyloxy.

[0050] Specific examples of aryloxy groups include, but are not limited to, phenoxy groups.

[0051] Specific examples of heteroaryloxy groups include, but are not limited to, thienyloxy groups.

[0052] Specific examples of silyl groups include, but are not limited to, trimethylsilyl and triphenylsilyl.

[0053] Examples of substituents that may be further present in the aforementioned alkyl, alkoxy, amino, aryloxy, silyl, aryl, and heterocyclic groups include halogen atoms such as fluorine, chlorine, bromine, and iodine; alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl; alkoxy groups such as methoxy, ethoxy, and propoxy; amino groups such as dimethylamino, diethylamino, dibenzylamino, diphenylamino, and xylylamino; aryloxy groups such as phenoxy; aryl groups such as phenyl and biphenyl; heterocyclic groups such as pyridyl and pyrrole; and cyano groups, but are not limited thereto.

[0054] (1) Organic compounds

[0055] First, the organic compounds according to the present invention are described.

[0056] The organic compounds according to the present invention are compounds represented by general formula (1-1) or (1-2).

[0057] [Chemical Formula 4]

[0058]

[0059] In general formula (1-1), the bonding site R a To R h At least four of the bonds are attached to the backbone selected from structure group A. At the bonding site R... a To R h In this context, the bonding sites not bonded to structure group A are each independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted silyl group, and cyano group.

[0060] In general formula (1-1), the bonding site R b R c R f and R g It can be bonded to a skeleton selected from structure group A.

[0061] In general formula (1-2), the bonding site R i To R p At least four of the bonds are attached to the backbone selected from structure group A. At the bonding site R... i To R p In this context, the bonding sites not bonded to structure group A are each independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted silyl group, and cyano group. X is an oxygen atom, sulfur atom, NR... 91 CR 92 R 93 or SiR 94 R 95 R 91 To R 95 Each is independently selected from the group consisting of: hydrogen atoms, deuterium atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heterocyclic groups.

[0062] In general formula (1-2), the bonding site R j R k R n and R o It can be bonded to a skeleton selected from structure group A.

[0063] [Chemical Formula 5]

[0064] Structure A Group

[0065]

[0066] In general formulas (2-1) to (2-10), R 1 To R 90 Each is independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted silyl group, and cyano group. X is oxygen atom, sulfur atom, NR 91 CR 92 R 93 or SiR 94 R 95 R 91 To R 95 Each group is independently selected from the following groups: hydrogen atom, deuterium atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group. Bonding position. Indicates bonding to the bonding site R a To R p The location.

[0067] The organic compounds according to the invention have a central skeleton as a naphthalene skeleton or a skeleton in which a six-membered ring is fused to both sides of a five-membered ring structure (e.g., a fluorene skeleton), and further have an indole-carbazole skeleton with a fused ring structure, thus being compounds with high thermal stability. The term "central skeleton" refers to the skeleton represented by general formula (1-1) or (1-2). Specifically, the organic compounds according to the invention differ from compounds Ref-1 and Ref-2 in that they have a central skeleton as a naphthalene skeleton or a skeleton in which a six-membered ring is fused to both sides of a five-membered ring structure (e.g., a fluorene skeleton), and have a carbazole skeleton fused with benzofuran or benzothiophene, etc. Therefore, the organic compounds according to the invention have a larger molecular weight than compounds Ref-1 and Ref-2. Therefore, the organic compounds according to the invention have strong intermolecular forces, and thus are organic compounds with high thermal stability.

[0068] Table 1 shows the results of TG-DTA (thermogravimetric-differential thermal analysis) measurements of the organic compounds according to the present invention and compound Ref-1 as a comparative example.

[0069] [Table 1]

[0070]

[0071] Table 1 shows that the 5% weight loss temperatures of compounds A-6, A-7, D-1, and D-2, which are examples of organic compounds according to the present invention, are 596°C, 573°C, 540°C, and 553°C, respectively, and are significantly higher than the 5% weight loss temperature of compound Ref-1, which is a comparative example. In particular, it is shown that the 5% weight loss temperatures of compounds A-6, A-7, and D-2 are more than 100°C higher than the 5% weight loss temperature of compound Ref-1.

[0072] As described above, the organic compounds according to the present invention have a large molecular weight because their structure consists of a central skeleton having a naphthalene skeleton or a skeleton in which a six-membered ring is fused to both sides of a five-membered ring structure (e.g., a fluorene skeleton), and a carbazole skeleton fused with benzofuran or benzothiophene, etc. Therefore, the organic compounds according to the present invention are considered to have high thermal stability.

[0073] Furthermore, the fusion of benzofuran or benzothiophene into the carbazole skeleton tends to lower the HOMO (highest occupied molecular orbital) energy level. Therefore, in the organic compounds according to the present invention, compounds having a carbazole skeleton fused with benzofuran or benzothiophene are considered to have high antioxidant stability.

[0074] Due to the above-mentioned characteristics, when the organic compound according to the present invention is used in an organic light-emitting element, an organic light-emitting element with high durability can be provided.

[0075] Specific examples of organic compounds according to the present invention are shown below. However, the invention is not limited thereto.

[0076] [Chemical Formula 6]

[0077]

[0078] [Chemical Formula 7]

[0079]

[0080] [Chemical Formula 8]

[0081]

[0082] [Chemical Formula 9]

[0083]

[0084] [Chemical Formula 10]

[0085]

[0086] [Chemical Formula 11]

[0087]

[0088] [Chemical Formula 12]

[0089]

[0090] [Chemical Formula 13]

[0091]

[0092] [Chemical Formula 14]

[0093]

[0094] [Chemical Formula 15]

[0095]

[0096] [Chemical Formula 16]

[0097]

[0098] [Chemical Formula 17]

[0099]

[0100] [Chemical Formula 18]

[0101]

[0102] [Chemical Formula 19]

[0103]

[0104] [Chemical Formula 20]

[0105]

[0106] [Chemical Formula 21]

[0107]

[0108] [Chemical Formula 22]

[0109]

[0110] [Chemical Formula 23]

[0111]

[0112] [Chemical Formula 24]

[0113]

[0114] [Chemical Formula 25]

[0115]

[0116] [Chemical Formula 26]

[0117]

[0118] [Chemical Formula 27]

[0119]

[0120] [Chemical Formula 28]

[0121]

[0122] [Chemical Formula 29]

[0123]

[0124] [Chemical Formula 30]

[0125]

[0126] [Chemical Formula 31]

[0127]

[0128] [Chemical Formula 32]

[0129]

[0130] [Chemical Formula 33]

[0131]

[0132] [Chemical Formula 34]

[0133]

[0134] [Chemical Formula 35]

[0135]

[0136] [Chemical Formula 36]

[0137]

[0138] [Chemical Formula 37]

[0139]

[0140] [Chemical Formula 38]

[0141]

[0142] [Chemical Formula 39]

[0143]

[0144] [Chemical Formula 40]

[0145]

[0146] [Chemical Formula 41]

[0147]

[0148] [Chemical Formula 42]

[0149]

[0150] [Chemical Formula 43]

[0151]

[0152] [Chemical Formula 44]

[0153]

[0154] [Chemical Formula 45]

[0155]

[0156] [Chemical Formula 46]

[0157]

[0158] [Chemical Formula 47]

[0159]

[0160] [Chemical Formula 48]

[0161]

[0162] [Chemical Formula 49]

[0163]

[0164] [Chemical Formula 50]

[0165]

[0166] [Chemical Formula 51]

[0167]

[0168] [Chemical Formula 52]

[0169]

[0170] [Chemical Formula 53]

[0171]

[0172] [Chemical Formula 54]

[0173]

[0174] [Chemical Formula 55]

[0175]

[0176] [Chemical Formula 56]

[0177]

[0178] [Chemical Formula 57]

[0179]

[0180] [Chemical Formula 58]

[0181]

[0182] [Chemical Formula 59]

[0183]

[0184] [Chemical Formula 60]

[0185]

[0186] [Chemical Formula 61]

[0187]

[0188] [Chemical Formula 62]

[0189]

[0190] [Chemical Formula 63]

[0191]

[0192] [Chemical Formula 64]

[0193]

[0194] [Chemical Formula 65]

[0195]

[0196] [Chemical Formula 66]

[0197]

[0198] In the organic compounds according to the invention, the synthetic routes of organic compounds having a central skeleton represented by general formula (1-1) are described in detail in the examples given later. In the organic compounds according to the invention, the synthetic routes of organic compounds having a central skeleton represented by general formula (1-2) are, for example, the following synthetic routes, but are not limited thereto.

[0199] [Chemical Formula 67]

[0200]

[0201] The organic compounds according to the present invention preferably further have the following characteristics.

[0202] (A) In general formula (1-1), the bonding site R a To R h At least four of the preferred bonds are attached to general formulas (2-1), (2-2), (2-4), (2-5), (2-6), (2-7), (2-8), (2-9), or (2-10).

[0203] (B) In organic compounds having a central skeleton represented by general formula (1-2), general formula (1-2) is preferably a fluorene skeleton.

[0204] (C) Organic compounds having a central skeleton represented by general formulas (1-1) and (1-2) preferably have bulky substituents.

[0205] These characteristics are described below.

[0206] (A) In general formula (1-1), the bonding site R a To R h At least four of the preferred bonds are attached to general formulas (2-1), (2-2), (2-4), (2-5), (2-6), (2-7), (2-8), (2-9), or (2-10).

[0207] In the organic compounds having characteristic (A), it is more preferred to bond to (2-1), (2-5), (2-6), (2-7) or (2-8). The organic compounds according to the invention are preferably represented by general formula (3-6) or (3-7).

[0208] [Chemical Formula 68]

[0209]

[0210] In general formulas (3-6) and (3-7), the bonding site R a R d R e and R hEach is independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, and cyano group. 46 To R 63 Each is independently selected from the following groups: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, and cyano group. X is oxygen atom, sulfur atom, NR 91 CR 92 R 93 or SiR 94 R 95 R 91 To R 95 Each is independently selected from the group consisting of: hydrogen atoms, deuterium atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heterocyclic groups.

[0211] In general formulas (3-6) and (3-7), R 46 To R 63 It can be a hydrogen atom, and R 46 To R 63 Each can be independently selected from the group consisting of: hydrogen atoms, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, and substituted or unsubstituted heterocyclic groups having 3 to 24 carbon atoms.

[0212] In the organic compounds according to the invention, among organic compounds having a central skeleton represented by the general formula (1-1), the organic compound having characteristic (A) is an organic compound with a particularly high oscillator strength. The oscillator strength of the organic compounds according to the invention was determined using Gaussian 16 (Gaussian 16, Revision C.01, MJ Frisch et al., Gaussian, Inc., Wallingford CT, 2019.), a molecular orbital calculation software manufactured by Gaussian, Inc., USA. The results are shown in Tables 2 and 3.

[0213] [Table 2]

[0214]

[0215] Compounds A-1 to A-10 are the following compounds.

[0216] [Chemical Formula 69]

[0217]

[0218] Table 2 shows that the oscillator strength values ​​of compounds A-1, A-2, and A-4 to A-10 are higher than those of compounds Ref-1 and Ref-2. In particular, in this invention, compounds A-1, A-5, A-6, A-7, and A-8 have particularly high oscillator strengths. The organic compounds represented as compounds A-1, A-2, and A-4 to A-10 are each compounds in which general formulas (2-1), (2-2), (2-4), (2-5), (2-6), (2-7), (2-8), (2-9), or (2-10) are bonded to a central skeleton represented by general formula (1-1).

[0219] [Table 3]

[0220]

[0221] Compounds B-1 to B-10 are the following compounds.

[0222] [Chemical Formula 70]

[0223]

[0224] Table 3 shows that the oscillator strength values ​​of compounds B-1, B-2, and B-4 to B-10 are higher than those of compounds Ref-1 and Ref-2. In particular, in this invention, compounds B-1, B-5, B-6, B-7, B-8, and B-9 have particularly high oscillator strengths. The organic compounds represented as compounds B-1, B-2, and B-4 to B-10 are each compounds in which general formulas (2-1), (2-2), (2-4), (2-5), (2-6), (2-7), (2-8), (2-9), or (2-10) are bonded to a central backbone represented by general formula (1-1).

[0225] The relationship between oscillator strength and quantum yield (luminescence efficiency) is described. As described in paragraph

[0262] of Japanese Patent Application Publication No. 2020-47930 and paragraph

[0035] of Japanese Patent Application Publication No. 2022-46999, compounds with high oscillator strength are known to exhibit high quantum yield (luminescence efficiency).

[0226] Therefore, from the viewpoint of oscillator strength, compounds of general formulas (2-1), (2-2), (2-4), (2-5), (2-6), (2-7), (2-8), (2-9), or (2-10) are preferably bonded to a central framework represented by general formula (1-1), and compounds of general formulas (2-1), (2-5), (2-6), (2-7), or (2-8) are more preferred, and compounds of general formulas (2-6), (2-7), or (2-8) are particularly preferred. X is preferably an oxygen atom or a sulfur atom, more preferably an oxygen atom.

[0227] (B) In organic compounds having a central skeleton represented by general formula (1-2), general formula (1-2) is preferably a fluorene skeleton.

[0228] Among the organic compounds with characteristic (B), the organic compounds represented by general formula (4-2) are more preferred.

[0229] [Chemical Formula 71]

[0230]

[0231] In general formula (4-2), the bonding site R i R l R m and R p Each is independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, and cyano group. 46 To R 54 Each is independently selected from the following groups: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, and cyano group. X is oxygen atom, sulfur atom, NR 91 CR 92 R 93 or SiR 94 R 95 R 91 To R 95 Each is independently selected from the group consisting of: hydrogen atoms, deuterium atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heterocyclic groups.

[0232] In the organic compounds according to the invention, among the organic compounds having a central framework represented by general formulas (1-2), the organic compound with characteristic (B) is an organic compound with particularly high oscillator strength. The oscillator strengths of compounds C-1 to C-14 were determined by the method described above. The results are shown in Table 4.

[0233] [Table 4]

[0234]

[0235] Compounds C-1 to C-14 are the following compounds.

[0236] [Chemical Formula 72]

[0237]

[0238] Table 4 shows that, in organic compounds having a central framework represented by general formula (1-2), particularly when the central framework represented by general formula (1-2) is a fluorene framework, the organic compounds according to this embodiment tend to exhibit high oscillator strength. This can be explained as follows: the fluorene framework itself has high oscillator strength, such that when general formula (1-2) is a fluorene framework, the organic compounds according to the invention tend to exhibit high oscillator strength.

[0239] Among the organic compounds according to this embodiment, those represented by general formula (4-2) exhibit particularly high oscillator strength. This can be explained as follows: the direction of the oscillator torque of fluorene, which forms the central framework, coincides with the extension direction of the framework further fused to the carbazole framework, resulting in particularly high oscillator strength.

[0240] (C) Organic compounds having a central skeleton represented by general formulas (1-1) and (1-2) preferably have bulky substituents.

[0241] In the organic compounds according to the invention, organic compounds having a central skeleton represented by general formulas (1-1) and (1-2) preferably have bulky substituents. Characteristic (C) provides an organic compound exhibiting higher oscillator strength. In the invention according to this embodiment, having bulky substituents is preferred because solvent solubility can be improved.

[0242] In the organic compounds according to this embodiment, the bulk substituent is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 12 carbon atoms, and preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms. Specifically, it can be isopropyl, cyclohexyl with phenyl, phenyl, phenyl with 3 to 6 carbon atoms, p-phenylene consisting of 2 to 3 phenyl groups, p-phenylene consisting of 2 to 3 phenyl groups and having a tert-butyl group, meta-phenylene consisting of 2 to 5 phenyl groups, or meta-phenylene consisting of 2 to 5 phenyl groups and having a methyl or isopropyl group. The phenyl with 3 to 6 carbon atoms can be a phenyl group having an isopropyl, tert-butyl, or cyclohexyl group. The meta-phenylene can be a structure in which the phenyl groups are linearly bonded, or a structure in which they are bonded in a branched manner.

[0243] Table 5 shows the oscillator strengths of compounds D-1 to D-20, which are organic compounds according to this embodiment. The oscillator strengths were obtained by the method described above.

[0244] [Table 5]

[0245]

[0246] Compounds D-1 to D-20 are the following compounds.

[0247] [Chemical Formula 73]

[0248]

[0249] [Chemical Formula 74]

[0250]

[0251] Table 5 shows that the organic compounds according to this embodiment exhibit high oscillator strength. Among the organic compounds according to this embodiment, those having substituents along their length are preferred, especially those having a central framework represented by general formulas (1-1) and (1-2). This is because such compounds exhibit particularly high oscillator strength.

[0252] As described above, the organic compounds according to the present invention are organic compounds with high thermal stability. Furthermore, among the organic compounds according to the present invention, the organic compounds having characteristic (A) or (B) are organic compounds with particularly high oscillator strength.

[0253] (2) Organic light-emitting element

[0254] Next, an organic light-emitting element according to an embodiment of the present invention will be described. An organic light-emitting element according to an embodiment of the present invention includes a first electrode, a second electrode, and an organic compound layer disposed between the electrodes. One of the first and second electrodes is an anode, and the other electrode is a cathode. In the organic light-emitting element according to this embodiment, the organic compound layer can be a single layer or a multi-layer stack, as long as the organic compound layer includes a light-emitting layer. The organic compound according to the present invention can be contained in the organic compound layer, and preferably in the light-emitting layer. When the organic compound layer is a multi-layer stack, in addition to the light-emitting layer, the organic compound layer may also include a hole injection layer, a hole transport layer, an electron blocking layer, a hole / exciton blocking layer, an electron transport layer, and an electron injection layer, etc. The light-emitting layer can be a single layer or a multi-layer stack. When the light-emitting layer includes multiple layers, a charge-generating layer can be disposed between the light-emitting layers. The charge-generating layer can be composed of a compound whose LUMO (lowest unoccupied molecular orbital) energy level is lower than the LUMO energy level of the hole transport layer, and the LUMO energy level of the charge-generating layer can be lower than the HOMO energy level of the hole transport layer. The HOMO and LUMO energy levels of the organic compound layer can be the HOMO and LUMO energy levels of the organic compound with the highest weight ratio in the organic compound layer.

[0255] The HOMO and LUMO levels, which are closer to the vacuum level, are described as "higher". When the LUMO level of the charge generation layer is lower than the HOMO level of the hole transport layer, it indicates that the LUMO level of the charge generation layer is further away from the vacuum level than the HOMO level of the hole transport layer.

[0256] In this specification, molecular orbital calculations can be used to calculate HOMO and LUMO energy levels. Molecular orbital calculations are performed using density functional theory (DFT) and other methods, and can utilize, for example, B3LYP functionals and 6-31G... Additional fuel tank designs include the following specifications: Gaussian 09 (Gaussian 09, Revision C.01, MJ Frisch, GW Trucks, HB Schlegel, GE Scuseria, 2013). Robb MA, JRCheeseman, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li, HP Hratchian, AF Izmaylov, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T , Honda Y , Kitao H , Vreven T , Montgomery JA , Peralta JE , Ogliaro M Bearpark , Heyd JJ , Kudin KN , Staroverov VN , Keith T , Kobayashi R , Normand K , Raghavachari K A , Rendell JC Burant, SS, Iyengar, J, Tomasi, M, Cossi, N, Rega, JM, Klene, JE, Knox, JB Cross, V, Bakken, C, Adamo, J, Jaramillo, R, Gomperts, RE, Stratmann, O, Yazyev, AJAustin, R, Cammi, C, Pomelli, JW, Ochterski, RL Martin, K, Morokuma, VG Zakrzewski , GA Voth , Salvador P , Dannenberg JJ , Dapprich S , ADDaniels , Farkas O , Foresman JB , Ortiz JV , J .Cioslowski, and DJFox, Gaussian, Inc., Wallingford CT, 2010.). .

[0257] The HOMO and LUMO energy levels in this specification can be calculated using ionization potential and band gap. The HOMO energy level can be estimated by measuring the ionization potential. After the analyte has been dissolved in a solvent such as toluene or after a vapor-deposited film of the analyte has been formed on a substrate such as glass, the ionization potential can be measured using a measuring device such as an AC-3. The band gap can be measured by dissolving the analyte in a solvent such as toluene and irradiating it with excitation light. The band gap can be determined by measuring the absorption end of the absorption spectrum of the excitation light. Alternatively, the band gap can be measured by vapor-depositing the analyte onto a substrate such as glass and applying excitation light to the vapor-deposited film. In the measurement, the absorption end of the absorption spectrum of the excitation light absorbed by the vapor-deposited film is measured, thereby determining the band gap.

[0258] The LUMO level can be calculated using the values ​​of the band gap and the ionization potential. The LUMO level can be estimated by subtracting the ionization potential from the band gap value.

[0259] The LUMO level can also be estimated from the reduction potential. For example, the single-electron reduction potential can be estimated using cyclic voltammetry (CV). CV measurements can be performed, for example, in a 0.1 M tetrabutylammonium perchlorate DMF solution using Ag / Ag+ as the reference electrode, Pt as the counter electrode, and glassy carbon as the working electrode. The LUMO level can be estimated by adding the difference between the reduction potential of the obtained compound and the reduction potential of ferrocene to -4.8 eV.

[0260] In an organic light-emitting element according to one embodiment of the present invention, when the organic compound according to the present invention is included in the light-emitting layer, the light-emitting layer may be a layer formed solely of the organic compound according to the present invention or a layer formed of the organic compound according to the present invention and other compounds. When the light-emitting layer is a layer formed of the organic compound according to the present invention and other compounds, the organic compound according to the present invention may be used as a host material or guest material of the light-emitting layer. The organic compound may also be used as an auxiliary material that can be included in the light-emitting layer. The host material, also called "host" or "first compound," is the compound that has the largest mass ratio among the compounds constituting the light-emitting layer. The guest material, also called "guest," "dopant material," "dopant," or "third compound," is the compound that has a smaller mass ratio than the host among the compounds constituting the light-emitting layer and is responsible for primary light emission. Therefore, the guest material may be called a light-emitting material. The auxiliary material, also called "auxiliary agent" or "second compound," is the compound that has a smaller mass ratio than the host material among the compounds constituting the light-emitting layer and assists the guest material in emitting light. The auxiliary material is also called a second host.

[0261] The lowest excitation singlet state energy of the host material is defined as S1(H), the lowest excitation singlet state energy of the guest material is defined as S1(D), and the lowest excitation singlet state energy of the auxiliary material is defined as S1(A). The guest material can be considered as an organic compound according to the present invention. In this case, the organic light-emitting element according to this embodiment preferably satisfies S1(H) > S1(D) or S1(H) > S1(A) > S1(D). When the lowest excitation singlet state energy of the compound contained in the organic light-emitting element according to this embodiment satisfies the above relationship, excitons can be effectively transferred to the guest material, resulting in higher luminous efficiency of the organic light-emitting element.

[0262] When the organic compound according to the invention is used as the guest material of the light-emitting layer, the concentration of the guest material relative to the entire light-emitting layer can be 0.01% by mass or more and less than 50% by mass, and preferably 0.01% by mass or more and less than 10% by mass, more preferably 0.01% by mass or more and less than 5% by mass. When the light-emitting layer includes auxiliary materials, the mass of the auxiliary materials relative to the entire light-emitting layer can be 1% by mass or more and less than 50% by mass, and preferably 10% by mass or more and less than 50% by mass.

[0263] The inventors have conducted various studies and discovered that when the organic compound according to the invention is used as the host or guest material of the light-emitting layer, particularly as the guest material of the light-emitting layer, it can provide an element with high efficiency and high brightness light output and very high durability. The light-emitting layer can have a single-layer or multi-layer structure. The light-emitting layer can contain a luminescent material having any other luminescent color to emit light having a color mixed with the blue luminescent color of this embodiment. A multi-layer structure refers to a state in which the light-emitting layer and other light-emitting layers are stacked on top of each other. In this case, the luminescent color of the organic light-emitting element is not limited to blue. More specifically, the luminescent color can be white or an intermediate color. In the case of white, the other light-emitting layers emit light of colors other than blue, i.e., red or green. The light-emitting layer is formed by vapor deposition or coating. Details are described in the embodiments given later.

[0264] The organic compounds according to the present invention can be used as constituent materials for organic compound layers other than the light-emitting layer of the organic light-emitting element according to this embodiment. Specifically, the organic compounds can be used as constituent materials for, for example, electron transport layers, electron injection layers, hole transport layers, hole injection layers, or hole blocking layers. In this case, the emission color of the organic light-emitting element is not limited to blue. More specifically, the emission color can be white or an intermediate color.

[0265] (3) Other compounds

[0266] In addition to the organic compounds according to the invention, conventionally known low-molecular-weight and high-molecular-weight hole-injection or hole-transporting compounds, host materials, luminescent compounds, electron-injection or electron-transporting compounds, etc., may be optionally used in combination. Examples of such compounds are described below.

[0267] Materials that facilitate hole injection from the anode and possess such high hole mobility that they can transport injected holes to the light-emitting layer are preferred as hole injection and transport materials. Materials with high glass transition temperatures are preferred to suppress crystallization of organic compounds, such as in organic light-emitting elements. Examples of low-molecular-weight and high-molecular-weight materials with hole injection and transport properties include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. These hole injection and transport materials are also suitable for use in electron blocking layers. When forming a hole injection layer by coating, a mixture of polyethylene dioxythiophene and polystyrene sulfonate (PEDOT:PSS), commonly used as hole injection materials, can be used. Non-limiting specific examples of compounds that can be used as hole injection and transport materials are shown below.

[0268] [Chemical Formula 75]

[0269]

[0270] Of the hole injection and transport materials given above, HT16 to HT18 can be used in the layer in contact with the anode to achieve a lower drive voltage. HT16 is widely used in organic light-emitting devices. HT2 to HT7, HT10, HT12, and HT22 to HT28 can be used in the organic compound layer adjacent to HT16. Hole transport polymers such as polyphenylenevinylene (PPV), polyfluorene (PF), polyvinylcarbazole (PVK), and their derivatives can be used. Alternatively, for example, inorganic insulating layers such as SiO2 and SiN, as well as organosilicon polymers such as siloxanes, can also be used. Multiple materials can be used in a single organic compound layer.

[0271] Examples of guest materials primarily involved in luminescent functionality include donor-acceptor type organic compounds, boron-containing complexes, indole-carbazole fused-ring compounds, fused-ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetraphenylene derivatives, anthracene derivatives, and rubrene), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-hydroxyquinoline)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymeric derivatives such as poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives. When producing luminescent layers by coating, luminescent polymers are primarily used. This is because polymers tend to exhibit high glass transition temperatures and are therefore less likely to undergo crystallization compared to low-molecular-weight compounds. Specific examples of materials used include polymers such as polyphenylenevinylene (PPV), polyfluorene (PF), polyvinylcarbazole (PVK), and their derivatives.

[0272] Non-limiting specific examples of compounds that can be used as luminescent materials are shown below.

[0273] [Chemical Formula 76]

[0274]

[0275] [Chemical Formula 77]

[0276]

[0277] Non-limiting specific examples of compounds that can be used as host or auxiliary materials contained in the luminescent layer are shown below.

[0278] [Chemical Formula 78]

[0279]

[0280] Considering factors such as the balance with the hole mobility of the hole transport material, any electron transport material capable of transporting electrons injected from the cathode to the light-emitting layer can be freely chosen. Examples of electron-transporting materials include oxadiazole derivatives, oxazole 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, thionyl derivatives, and anthracene derivatives). These electron transport materials are also suitable for use in hole-blocking layers.

[0281] Non-limiting specific examples of compounds that can be used as electron transport materials are shown below.

[0282] [Chemical Formula 79]

[0283]

[0284] Considering factors such as the balance with hole injection, any electron injection material capable of readily injecting electrons from the cathode can be freely chosen. Both n-type dopants and reducing dopants are included as organic compounds. Examples include alkali metal compounds such as lithium fluoride, lithium complexes such as lithium hydroxyquinoline, benzimidazolidine derivatives, imidazolidine derivatives, fulvalene derivatives, and acridine derivatives.

[0285] These can also be used in combination with the aforementioned electronic transport materials.

[0286] The organic compounds according to the present invention can also be used in the form of ink compositions.

[0287] The ink composition according to this embodiment comprises at least one compound represented by general formula (1-1) or (1-2). Using the ink composition according to this embodiment, a layer formed from the organic compound constituting the organic light-emitting element, particularly the light-emitting layer, can be formed by coating, thus allowing for the easy production of large-area elements at a relatively low cost. Examples of solvents for dissolving the compounds represented by general formula (1-1) or (1-2) include toluene, xylene, mesitylene, dioxane, methylnaphthalene, tetrahydrofuran, diethylene glycol dimethyl ether, 1,2-dichlorobenzene, and 1,2-dichloropropane. These solvents can be used alone or in combination of two or more. Solvents with suitable evaporation rates, particularly those with boiling points of about 70°C to 200°C, are preferred because they readily provide films with uniform thickness. The ink composition according to this embodiment may further comprise compounds used as additives. Examples of compounds used as additives include the aforementioned known light-emitting layer host or light-emitting auxiliary materials, hole transport materials, light-emitting materials, and electron transport materials.

[0288] In the ink composition according to this embodiment, the concentration of the compound represented by general formula (1-1) or (1-2) is preferably 0.05% by weight or more and 20% by weight or less relative to the whole composition, more preferably 0.1% by weight or more and 5% by weight or less.

[0289] The ink composition according to this embodiment can be formed into a film by spin coating, bar coating, slot coating, inkjet coating, nozzle coating, casting or gravure printing, thereby forming the organic layer of the organic light-emitting element.

[0290] (4) Composition of organic light-emitting elements

[0291] The constituent components constituting the organic light-emitting element according to this embodiment are described below.

[0292] An organic light-emitting element is formed on a substrate by creating an insulating layer, a first electrode, an organic compound layer, and a second electrode. A protective layer, a color filter, a microlens, etc., can be formed on the second electrode. When a color filter is provided, a planarization layer can be provided between the color filter and the protective layer. The planarization layer can be formed of, for example, an acrylic resin. This also applies when the planarization layer is provided between the color filter and the microlens.

[0293] [Substrate]

[0294] Examples of substrates include quartz, glass, silicon wafers, resin, and metal. The substrate may have switching elements, such as transistors, and wiring disposed thereon, and may have an insulating layer disposed thereon. The insulating layer can be made of any material, as long as contact holes can be formed therein to allow the formation of wiring connected to the first electrode, and it can provide insulation from unconnected wiring. For example, resins such as polyimide, silicon oxide, and silicon nitride can be used.

[0295] [electrode]

[0296] An electrode can be a pair of electrodes. A pair of electrodes consists of a first electrode and a second electrode. Specifically, a pair of electrodes can be an anode and a cathode. When an electric field is applied in the direction of light emission from the organic light-emitting element, one of the electrodes at the higher potential is the anode, and the other is the cathode. In other words, one of the electrodes supplying holes to the light-emitting layer is the anode, and the other electrode supplying electrons to the light-emitting layer is the cathode.

[0297] The anode material preferably has the highest possible work function. For example, elemental metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten, mixtures containing these metals, alloys obtained by combining these metals, and metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide can also be used. Conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.

[0298] These electrode materials can be used alone or in combination of two or more. The anode can consist of a single layer or multiple layers.

[0299] When the anode is used as a reflective electrode, materials such as chromium, aluminum, silver, titanium, tungsten, molybdenum, their alloys, or stacks thereof can be used. These materials can also be used as reflective films that do not function as electrodes. When the anode is used as a transparent electrode, it can be, but is not necessarily, a transparent conductive layer made of oxides such as indium tin oxide (ITO) or indium zinc oxide. Photolithography can be used to form the electrode.

[0300] The cathode material preferably has a low work function. Examples of such materials include alkali metals such as lithium, alkaline earth metals such as calcium, elemental metals such as aluminum, titanium, manganese, silver, lead, and chromium, and mixtures thereof. Alloys obtained by combining these elemental metals can also be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, and zinc-silver alloys can be used. Metal oxides such as indium tin oxide (ITO) can also be used. These electrode materials can be used alone or in combination of two or more. The cathode can be composed of a single layer or multiple layers. In particular, silver is preferred, and silver alloys are more preferred to reduce silver aggregation. The content ratio in the alloy is not limited as long as it reduces silver aggregation. For example, the ratio of silver to other metals can be, for example, 1:1 or 3:1.

[0301] There are no particular limitations on the cathode; a conductive layer formed of oxides such as ITO can be used to provide the top emitting element, or a reflective electrode formed of aluminum (Al) or the like can be used to provide the bottom emitting element. There are no particular limitations on the method of forming the cathode, but DC sputtering or AC sputtering is preferred because it allows for good film coverage and tends to reduce resistance.

[0302] [Organic compound layer]

[0303] The organic compound layer can be formed as a single layer or multiple layers. When the organic compound layer comprises multiple layers, depending on their function, the layers can be called a hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, and electron injection layer. The organic compound layer is mainly composed of organic compounds and may contain inorganic atoms and inorganic compounds. For example, the organic compound layer may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, or zinc. The organic compound layer can be disposed between the first electrode and the second electrode and can be configured to contact the first electrode and the second electrode.

[0304] The organic compound layers constituting the organic light-emitting element according to this embodiment (e.g., hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, and electron injection layer) are formed by the following method.

[0305] The organic compound layer constituting the organic light-emitting element according to this embodiment can be formed using dry methods such as vacuum evaporation, ionization evaporation, sputtering, or plasma. Alternatively, a wet method can be used, in which a solution in a suitable solvent is used to form the layer by a known coating method (e.g., spin coating, dip coating, casting, LB coating, or inkjet coating).

[0306] When a layer is formed by means such as vacuum evaporation or solution coating, the layer is less likely to undergo crystallization and exhibits high stability over time. When forming a film using a coating method, appropriate binder resins can be combined to form the film.

[0307] Examples of adhesive resins include, but are not limited to, polyvinylcarbazole resins, polycarbonate resins, polyester resins, ABS resins, acrylic resins, polyimide resins, phenolic resins, epoxy resins, silicone resins, and urea-formaldehyde resins.

[0308] These adhesive resins can be used alone as homopolymers or copolymers, or as a mixture of two or more. Furthermore, known additives such as plasticizers, antioxidants, and UV absorbers can be used in combination as needed.

[0309] [Protective Layer]

[0310] A protective layer can be disposed on the cathode. For example, a glass component with a desiccant can be attached to the cathode to reduce, for example, water ingress into the organic compound layer, thereby reducing the occurrence of display defects. In another embodiment, a passivation film made of silicon nitride or the like can be disposed on the cathode to reduce, for example, water ingress into the organic compound layer. For example, the protective layer can be formed in a manner that the resulting material is transferred to another chamber after cathode formation without breaking the vacuum, and a silicon nitride film with a thickness of 2 μm can be formed by CVD. After the film is formed by CVD, atomic layer deposition (ALD) can be performed to form the protective layer. The material of the film formed by ALD is not limited and can be, for example, silicon nitride, silicon oxide, or aluminum oxide. Silicon nitride can be further formed by CVD on the film formed by ALD. The film formed by ALD can have a smaller thickness than the film formed by CVD. Specifically, the thickness of the film formed by ALD can be less than 50% of the thickness of the film formed by CVD, or even less than 10%.

[0311] [Color Filter]

[0312] The color filter can be disposed on the protective layer. For example, the color filter can be formed on another substrate to correspond to the size of the organic light-emitting element and attached to the substrate on which the organic light-emitting element is disposed. Optionally, the color filter can be patterned on the aforementioned protective layer by photolithography. The color filter can be formed from a polymer.

[0313] [Planning Layer]

[0314] A planarization layer can be disposed between the color filter and the protective layer. The planarization layer is disposed to reduce the non-uniformity of the underlying layer. The planarization layer can be referred to as a material resin layer, without limitation. The planarization layer can be formed from an organic compound. The organic compound can have a low molecular weight or a high molecular weight, and preferably a high molecular weight.

[0315] The planarization layer can be applied to the opposite surfaces of the color filter, and its constituent materials can be the same or different. Specific examples include polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, and urea-formaldehyde resin.

[0316] [Microlens]

[0317] The organic light-emitting element according to this embodiment may include optical components, such as microlenses, on its light-emitting side. The microlenses may be formed from acrylic resins or epoxy resins, etc. The microlenses can be used to increase the amount of light extracted from the organic light-emitting element and to control the direction of the extracted light. The microlenses may have a hemispherical shape. In the case of a hemispherical shape, there exists a tangent parallel to the insulating layer in the tangent of the hemisphere, and the point of contact between this tangent and the hemisphere is the vertex of the microlens. The vertex of the microlens can be determined in the same way in any cross-sectional view. That is, in the cross-sectional view, there exists a tangent parallel to the insulating layer in the tangent to the semicircle of the microlens, and the point of contact between this tangent and the semicircle is the vertex of the microlens.

[0318] The midpoint of a microlens can also be defined. In the cross-section of a microlens, imagine a line segment from the starting point of one arc shape to the starting point of another arc shape, and the midpoint of this line segment can be called the midpoint of the microlens. The cross-section used to determine the vertex and midpoint can be a cross-section perpendicular to the insulating layer.

[0319] [Opposing substrate]

[0320] The opposing substrate can be disposed on the planarization layer. Since the opposing substrate is disposed opposite to the aforementioned substrate, it is called the opposing substrate. The constituent material of the opposing substrate can be the same as that of the aforementioned substrate. When the aforementioned substrate is the first substrate, the opposing substrate can be the second substrate.

[0321] [Pixel Circuit]

[0322] The light-emitting device may include pixel circuits connected to light-emitting elements. The pixel circuits may be active matrix circuits that independently control the light emission of a first light-emitting element and a second light-emitting element. The active matrix circuits may be voltage-programmable or current-programmable. The driving circuitry includes pixel circuits for each pixel. The pixel circuits may include light-emitting elements, transistors controlling the brightness of the light-emitting elements, transistors controlling the timing of light emission, capacitors maintaining the gate voltage of the transistors controlling the brightness, and transistors providing a connection to GND without passing through the light-emitting elements.

[0323] The light-emitting device has a display area and a peripheral area disposed around the display area. The display area includes pixel circuitry, and the peripheral area includes display control circuitry. The mobility of the transistors constituting the pixel circuitry may be lower than the mobility of the transistors constituting the display control circuitry.

[0324] The slope of the current-voltage characteristic of the transistors constituting the pixel circuit can be less 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 determined based on the so-called Vg-Ig characteristic.

[0325] The transistors that make up the pixel circuit are transistors connected to light-emitting elements such as the first light-emitting element.

[0326] [pixel]

[0327] Organic light-emitting devices comprise multiple pixels. Each pixel includes sub-pixels that emit light of different colors from each other. Sub-pixels can each have emission colors such as R, G, and B.

[0328] Within each pixel, an area also known as a pixel aperture emits light. This area is the same as the first area. The size of the pixel aperture can be less than 15 μm and greater than 5 μm. More specifically, the size can be, for example, 11 μm, 9.5 μm, 7.4 μm, or 6.4 μm.

[0329] The distance between sub-pixels can be less than 10μm, specifically 8μm, 7.4μm or 6.4μm.

[0330] When viewed in a planar diagram, pixels can have a known configuration. For example, a configuration can be a stripe configuration, a delta configuration, a PenTile configuration, or a Bayer configuration. The shape of a subpixel in the planar diagram can be any known shape. Examples include quadrilaterals such as rectangles and rhombuses, as well as hexagons. It should be understood that shapes that are not exact rectangles but resemble rectangles are also considered rectangles. Subpixel shapes and pixel arrangements can be combined.

[0331] (5) Application of organic light-emitting elements according to this implementation plan

[0332] The organic light-emitting element according to this embodiment can be used as a component of display devices or lighting devices. Other applications include exposure light sources in electrophotographic image forming equipment, backlights in liquid crystal displays, and light-emitting devices including white light sources with color filters.

[0333] The display device may be an image information processor, which includes an image input unit that inputs image information from a regional CCD, a linear CCD, or a memory card, etc., includes an information processing unit configured to process the input information, and displays the input image on the display unit.

[0334] The display unit of a camera device or inkjet printer can have a touch panel function. The touch panel function can be activated by any system, such as an infrared system, an electrostatic capacitive system, a resistive film system, or an electromagnetic induction system. The display device can also be used as the display unit of a multifunction printer.

[0335] Next, the display device according to this embodiment will be described with reference to the accompanying drawings.

[0336] Figure 1A and Figure 1B These are schematic cross-sectional views illustrating examples of display devices, each including 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 can be a thin-film transistor (TFT).

[0337] Figure 1A This is an example of a pixel as a component of a display device according to this embodiment. The pixel includes sub-pixels 10. Sub-pixels are classified as 10R, 10G, and 10B based on their emission characteristics. The emitted color can be distinguished based on the wavelength of light emitted from the light-emitting layer, or the light emitted from the sub-pixels can be selectively transmitted or color-converted through a color filter, etc. Each sub-pixel includes a reflective electrode 2 serving as a first electrode, an insulating layer 3 covering the edge of the reflective electrode 2, an organic compound layer 4 covering the first electrode and the insulating layer, a transparent electrode 5, a protective layer 6, and a color filter 7 on the interlayer insulating layer 1.

[0338] The interlayer insulating layer 1 may include transistor and capacitor elements located below or inside the interlayer insulating layer 1. The transistor and the first electrode may be electrically connected to each other through contact holes (not shown) or the like.

[0339] The insulating layer 3 is also called a bank or pixel separation film. The insulating layer 3 is configured to cover the edge of the first electrode and surround the first electrode. The portion without the insulating layer is in contact with the organic compound layer 4 and serves as the light-emitting area.

[0340] The organic compound layer 4 includes a hole injection layer 41, a hole transport layer 42, a first light-emitting layer 43, a second light-emitting layer 44, and an electron transport layer 45.

[0341] The second electrode 5 can be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0342] Protective layer 6 reduces the penetration of moisture into the organic compound layer. Although the protective layer is shown as a single layer, it can be composed of multiple layers. The layers can consist of inorganic compound layers and organic compound layers.

[0343] Color filters 7 are classified as 7R, 7G, and 7B according to their color. Color filters can be formed on a planarization film (not shown). A resin protective layer (not shown) can be disposed on the color filters. Color filters can be formed on a protective layer 6. Color filters can be bonded to opposing substrates, such as a glass substrate, after being disposed on them.

[0344] exist Figure 1B The display device 100 shown includes an organic light-emitting element 26 and a TFT 18, an example of a transistor. The display device 100 includes a substrate 11 made of glass or silicon, and an insulating layer 12 disposed thereon. An active element 18, such as a TFT, is disposed on the insulating layer, and a gate electrode 13, a gate insulating film 14, and a semiconductor layer 15 of the active element are also disposed thereon. The active element 18 also includes the semiconductor layer 15, a drain electrode 16, and a source electrode 17. An insulating film 19 is disposed on the active element 18. The anode 21 and the source electrode 17 constituting the organic light-emitting element 26 are connected to each other through contact holes 20 extending through the insulating film.

[0345] The electrodes (anode and cathode) included in the organic light-emitting element 26 and the electrodes (source and drain electrodes) included in the TFT do not necessarily have to be... Figure 1B The electrodes are electrically connected to each other as shown. Only the anode or cathode needs to be electrically connected to the source or drain electrode of the TFT. TFT stands for Thin Film Transistor.

[0346] Although the organic compound layer is Figure 1B The display device 100 is shown as a single layer, but the organic compound layer 22 may be composed of multiple layers. A first protective layer 24 and a second protective layer 25 for reducing the degradation of the organic light-emitting element are disposed on the cathode 23.

[0347] Although transistors are used as Figure 1B The switching element in the display device 100 can be replaced by other switching elements.

[0348] Figure 1B The transistors used in the display device 100 can be not only transistors obtained using a single-crystal silicon wafer, but also thin-film transistors including a substrate and an active layer on an insulating surface of the substrate. The active layer can be made of, for example, single-crystal silicon, non-single-crystal silicon such as amorphous silicon or microcrystalline silicon, or non-single-crystal oxide semiconductors such as indium zinc oxide or indium gallium zinc oxide. Thin-film transistors are also called TFT elements.

[0349] Included Figure 1B The transistors in the display device 100 can be formed in a substrate, such as a Si substrate. The phrase "formed in a substrate" means that the transistors are produced by processing the substrate itself, such as a Si substrate. That is, having transistors in a substrate can also mean that the substrate and the transistors are formed integrally.

[0350] The luminous intensity of the organic light-emitting element according to this embodiment is controlled by a TFT, which is an example of a switching element. Multiple organic light-emitting elements are arranged in the screen to enable the display of images with different luminous intensities. The switching element according to this embodiment is not limited to a TFT, but can also be a transistor formed of low-temperature polysilicon or an active matrix driver formed on a substrate such as a Si substrate. The phrase "on the substrate" can also be referred to as "in the substrate." The choice between setting transistors in the substrate or using TFTs depends on the size of the display. For example, when the size of the display is approximately 0.5 inches, the organic light-emitting element is preferably disposed on a Si substrate.

[0351] Figure 2 This is a schematic diagram illustrating an example of a display device according to this embodiment. The display device 1000 may include an upper cover 1001, a lower cover 1009, and a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 disposed between the covers. The display panel 1005 may include an organic light-emitting element according to this embodiment. Flexible printed circuits (FPCs) 1002 and 1004 are connected to the touch panel 1003 and the display panel 1005, respectively. Transistors are printed on the circuit board 1007. If the display device is not a mobile device, the battery 1008 can be omitted. If the display device is a mobile device, the battery 1008 can be disposed in other locations.

[0352] The display device according to this embodiment may include red, green, and blue color filters. The red, green, and blue color filters may be configured in a triangular arrangement.

[0353] The display device according to this embodiment can be used as the display unit of a mobile terminal. In this case, the display device can have both display and operation functions. Examples of mobile terminals include portable phones such as smartphones, tablet computers, and head-mounted displays.

[0354] The display device according to this embodiment can be used as a display unit of a camera device, which includes an imaging element configured to receive light. The camera device may include a display unit configured to display information acquired by the imaging element. The display unit may be exposed outside the camera device or disposed in a viewfinder. The camera device may be a digital camera or a digital video camera.

[0355] Figure 3A This is a schematic diagram illustrating an example of a camera device according to this embodiment. The camera device 1100 may include a viewfinder 1101, a rear display 1102, an operation unit 1103, and a housing 1104. The viewfinder 1101 and the rear display 1102 may include organic light-emitting elements according to this embodiment. In this case, the viewfinder 1101 and the rear display 1102 can display not only the image to be captured, but also environmental information, camera commands, etc. Environmental information may include, for example, the intensity of external light, the direction of external light, the speed of movement of the subject, or the possibility that the subject is obstructed by an object.

[0356] Since the opportunity to capture an image is only fleeting, it is desirable to display the information as quickly as possible. Therefore, a display device including an organic light-emitting element according to this embodiment is preferred. This is because organic light-emitting elements have a high response speed.

[0357] The imaging device 1100 may further include an optical unit (not shown). The optical unit may have a single lens or multiple lenses and focuses the image onto an imaging element 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 be referred to as a photoelectric conversion device. Instead of sequential imaging, the photoelectric conversion device may involve detecting differences from previous images or extracting images from continuously recorded images as an imaging method.

[0358] Figure 3B This is a schematic diagram illustrating an example of an electronic device according to this embodiment. The electronic device 1200 includes a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may include circuitry, a printed circuit board including the circuitry, a battery, and a communication unit. The operation unit 1202 may be a button or a touch-sensitive response unit. The operation unit may be, for example, a biometric unit that unlocks the device after fingerprint recognition. An electronic device including a communication unit may also be called a communication device. The electronic device may further have a camera function by including a lens and an imaging element. Images captured by the camera function are displayed on the display unit. Examples of electronic devices include smartphones and laptops.

[0359] Figure 4A and Figure 4B This is a schematic diagram illustrating an example of a display device according to this embodiment. Figure 4A Such as a television monitor or PC monitor. The display device 1300 includes a housing 1301 and a display unit 1302. The organic light-emitting element according to this embodiment can be used in the display unit 1302.

[0360] The display device 1300 may include a support housing 1301 and a base 1303 for the display unit 1302. The base 1303 does not necessarily have to be... Figure 4A As shown in the diagram. The lower side of the housing 1301 can be used as a base.

[0361] The housing 1301 and the display unit 1302 can be curved. The radius of curvature can be more than 5000 mm and less than 6000 mm.

[0362] Figure 4B This is a schematic diagram illustrating another example of a display device according to this embodiment. Figure 4B The display device 1310 is configured to be foldable and is a so-called foldable display device. The display device 1310 includes a first display portion 1311, a second display portion 1312, a housing 1313, and a bending point 1314. The first display portion 1311 and the second display portion 1312 may include organic light-emitting elements according to this embodiment. The first display portion 1311 and the second display portion 1312 may be a single seamless display device. The first display portion 1311 and the second display portion 1312 may be divided by the bending point. The first display portion 1311 and the second display portion 1312 may display different images, or the first and second display portions may display a single image together.

[0363] Figure 5A This is a schematic diagram illustrating an example of a lighting device according to this embodiment. The lighting device 1400 may include a housing 1401, a light source 1402, and a circuit board 1403. The light source 1402 may include an organic light-emitting element according to this embodiment. To improve the color rendering index of the light source, the lighting device 1400 may include an optical film 1404. To effectively diffuse light from the light source, the lighting device 1400 may include a light diffuser 1405. The lighting device 1400 including the light diffuser 1405 allows light to reach a wide area. The optical film 1404 and the light diffuser 1405 may be disposed on the light-emitting side of the lighting device. If necessary, a cover may be disposed at the outermost portion.

[0364] The lighting device is, for example, an indoor lighting device. The lighting device may emit white, daylight white, or any other color of light from blue to red. The lighting device according to this embodiment may include a modulation circuit configured to modulate light. The lighting device according to this embodiment may include a power supply circuit connected to the organic light-emitting element according to this embodiment. The power supply circuit may be a circuit configured to convert AC voltage to DC voltage. White is a color with a color temperature of 4200K, and daylight white is a color with a color temperature of 5000K. The lighting device according to this embodiment may further include a color filter.

[0365] The lighting device according to this embodiment may also include a heat dissipation section. The heat dissipation section is configured to dissipate heat from the device to the outside, and may be, for example, a metal or ceramic with high thermal conductivity.

[0366] Figure 5B This is a schematic diagram of an automobile as an example of a moving body according to this embodiment. The automobile includes taillights as an example of lamps. The automobile 1500 includes taillights 1501 and a body 1503, and the taillights may be configured to open in response to, for example, braking operations. The body 1503 may also be referred to as a chassis. The automobile 1500 may include windows 1502 attached to the body 1503.

[0367] The taillight 1501 may include an organic light-emitting element according to this embodiment. The taillight may include a protective member to protect the light source. The protective member may be formed of any material having a certain degree of high strength and transparency, but is preferably formed of polycarbonate or the like. Polycarbonate may be mixed with furan dicarboxylic acid derivatives or acrylonitrile derivatives, etc.

[0368] Window 1502 can be a transparent display, unless it is a window used for inspecting the front and rear of a vehicle. The transparent display may include an organic light-emitting element according to this embodiment. In this case, components of the organic light-emitting element according to the invention, such as electrodes, are made of transparent members.

[0369] The mobile body according to this embodiment includes one or both of a drive force generating unit configured to generate a driving force primarily for the movement of the mobile body and a rotating body primarily for the movement of the mobile body. The drive force generating unit may be an engine or motor, etc. The rotating body may be a tire, wheel, ship's screw, or aircraft's propeller, etc. Specifically, the mobile body may be a bicycle, car, train, ship, aircraft, or drone, etc. The mobile body may include a body and lights mounted on the body. The lights can emit light to allow identification of the body's position.

[0370] Reference Figure 6A and Figure 6B This section describes application examples of the display device according to the above embodiments. The display device can be applied to systems that can be worn as wearable devices such as smart glasses, head-mounted displays, and smart contact lenses. Display devices that can be used in wearable devices may include camera devices capable of photoelectric conversion of visible light and display devices capable of emitting visible light.

[0371] Figure 6A and Figure 6B This is a schematic diagram illustrating an example of eyeglasses (smart glasses) according to this embodiment. (Refer to...) Figure 6AThe glasses 1600 (smart glasses) are described. The glasses 1600 includes a display portion on the back side of a lens 1601. The display portion may include an organic light-emitting element according to the present invention. Furthermore, a camera device 1602, such as a CMOS sensor or a SPAD, may be disposed on the front side of the lens 1601.

[0372] The glasses 1600 further include a controller 1603. The controller 1603 functions as a power supply to the camera device 1602 and the display unit. The controller 1603 controls the operation of the camera device 1602 and the display unit. The lens 1601 is provided with an optical system for focusing light for the camera device 1602 and the display unit.

[0373] Reference Figure 6B Glasses 1610 (smart glasses) are described. Glasses 1610 includes a controller 1612, and the controller 1612 is equipped with a display device including an organic light-emitting element according to the invention. The controller 1612 may further include a camera device corresponding to a camera device 1602. A lens 1611 is provided with an optical system for projecting light emitted from the controller 1612, and an image is projected onto the lens 1611. The controller 1612 functions as a power source for powering the camera device and the display device, and also controls the operation of the camera device and the display device. The controller may include a gaze detection unit configured to detect the wearer's gaze. Infrared light can be used to detect the gaze. An infrared light-emitting unit emits infrared light towards the eyeball of a user gazing at the displayed image. Reflected light from the eyeball in the emitted infrared light is detected by the camera unit, which includes a light-receiving element, thereby obtaining a photographic image of the eyeball. Because a light reduction unit configured to reduce light from the infrared light-emitting unit to the display unit is present in the planar view, image quality degradation is reduced.

[0374] The controller 1612 detects the user's gaze toward the displayed image from an image of the eye obtained by infrared photography. Any known method can be used to detect the gaze using the image of the eye. For example, a gaze detection method based on a Purkinje image formed by reflecting illumination light onto the cornea can be used.

[0375] More specifically, gaze detection processing based on the pupil-corneal reflection method is performed. Using the pupil-corneal reflection method, a gaze vector representing the direction (rotation angle) of the eyeball is generated based on the pupil image and Purkinje image included in the camera image of the eyeball, thereby detecting the user's gaze.

[0376] The display device according to this embodiment may include a camera device, which includes a light receiving element and can control the image displayed on the display device based on the user's gaze information from the camera device.

[0377] Specifically, the display device determines a first viewing area and a second viewing area (excluding the first viewing area) based on gaze information. The first and second viewing areas can be determined by the display device's controller, or by an external controller and transmitted from there. Within the display area of ​​the display device, the display resolution of the first viewing area can be controlled to be higher than the display resolution of the second viewing area. That is, the resolution of the second viewing area can be set to be lower than the resolution of the first viewing area.

[0378] The display area includes a first viewing area and a second viewing area different from the first viewing area, and a high-priority area is determined from the first and second viewing areas based on gaze information. The first and second viewing areas can be determined by the display device's controller, or they can be determined by and sent from an external controller. The resolution in the high-priority area can be controlled to be higher than the resolution in areas other than the high-priority area. That is, the resolution in relatively low-priority areas can be set lower.

[0379] AI can be used to determine the primary or high-priority viewing area. AI can be a model configured to use images of the eye and the actual direction of the eye's gaze within the image as teaching data, and to estimate the angle of the gaze and the distance to the object being viewed from the image of the eye. AI can be included in a display device, a camera device, or an external device. When the external device includes AI, it can be appropriately used in smart glasses that further include a camera device configured to capture external images. The smart glasses can display external information from the camera in real time.

[0380] Figure 7A This is a schematic diagram illustrating an example of an image forming apparatus according to this embodiment. 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 fixing unit 35. The exposure light source 28 emits light 29 and forms an electrostatic latent image on the surface of the photoreceptor 27. The exposure light source 28 may include an organic light-emitting element according to this embodiment. The developing unit 31 contains toner, etc. The charging unit 30 charges the photoreceptor 27. The transfer unit 32 transfers the developed image onto a recording medium 34. The transport roller 33 transports the recording medium 34. The recording medium 34 is, for example, paper. The fixing unit 35 fixes the image formed on the recording medium 34.

[0381] Figure 7B and Figure 7CEach of the exposure light sources 28 is shown, and each schematically illustrates how multiple light-emitting units 36 are arranged on a long substrate. Arrow 37 indicates the column direction of the organic light-emitting elements. The column direction is the same as the direction of the rotation axis of the photoreceptor 27. This direction can also be referred to as the long axis direction of the photoreceptor 27. Figure 7B In this configuration, the light-emitting portion 36 is arranged along the long axis of the photoreceptor 27. Figure 7C In, with Figure 7B The difference lies in the arrangement of the light-emitting portions 36 in the first and second columns, which are alternately arranged in the column direction. The first and second columns are located at different positions in the row direction. In the first column, multiple light-emitting portions 36 are arranged at intervals. In the second column, the light-emitting portions 36 are arranged at positions corresponding to the intervals between the light-emitting portions 36 in the first column. That is, multiple light-emitting portions 36 are also arranged at intervals in the row direction. Figure 7C The configuration in the text can be described as, for example, a grid configuration, an alternating configuration, or a checkered pattern.

[0382] As described above, using a device that includes an organic light-emitting element according to this embodiment enables stable display with good image quality over a long period of time.

[0383] Example

[0384] The invention will now be described with reference to embodiments. It should be noted that the invention is not limited thereto.

[0385] [Example 1]

[0386] (1) Synthesis of compound A-6

[0387] Compound A-6 was synthesized according to the following synthetic route.

[0388] [Chemical Formula 80]

[0389]

[0390] (1-1) Synthesis of Intermediate 1

[0391] 1,3-Dichloro-2-nitrobenzene (5 g), dibenzo[b,d]furan-4-ylboronic acid (5.6 g), tetrakis(triphenylphosphine)palladium (0.61 g), sodium carbonate (8.5 g), dioxane (40 mL), and water (10 mL) were added, and the mixture was stirred at 100 °C for 10 hours. After extraction with dichloromethane, the result was concentrated. The concentrate was washed with methanol and filtered to obtain 6 g of intermediate 1 as a white solid.

[0392] (1-2) Synthesis of intermediate 2

[0393] Intermediate 1 (7.8 g), triphenylphosphine (14.15 g), and o-dichlorobenzene (180 mL) were added, and the mixture was stirred at 220 °C for 120 hours. After distilling off the o-dichlorobenzene, the mixture was subjected to silica gel chromatography with ethyl acetate:heptane = 1:4 to obtain 5.41 g of intermediate 2 as a white powder.

[0394] (1-3) Synthesis of intermediate 3

[0395] Intermediate 2 (3.4 g), bis(pinacol)diboron (8.8 g), tris(dibenzylacetone)dipalladium(0) (0.33 g), XPhos (0.33 g), potassium acetate (3.41 g), and dioxane (100 mL) were added, and after Ar bubbling, the mixture was stirred at 100 °C for 8 hours under nitrogen. Water was added, and the mixture was extracted with toluene. After distilling off the toluene, the mixture was subjected to silica gel chromatography with ethyl acetate:heptane = 1:10 to obtain 3.84 g of intermediate 3.

[0396] (1-4) Synthesis of intermediate 4

[0397] 2,6-Dichloro-3,7-dimethoxynaphthalene (5 g) and dichloromethane (200 mL) were added, and the mixture was cooled in an ice bath. Boron tribromide (17% in dichloromethane, ca. 1 mol / L) (97 mL) was then added dropwise. The mixture was brought to room temperature and stirred for another 16 hours. Water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate was distilled off to obtain 3.9 g of intermediate 4.

[0398] (1-5) Synthesis of intermediate 5

[0399] Intermediate 4 (1.83 g), dichloromethane (60 mL), and pyridine (2.58 mL) were added, and the mixture was cooled in an ice bath. Trifluoromethanesulfonic anhydride (3.37 mL) was then added dropwise. The mixture was brought to room temperature and stirred for another 16 hours. Water was added, and the mixture was extracted with dichloromethane, which was then distilled off. Silica gel chromatography with dichloromethane was performed to obtain intermediate 5 as a white powder (3.23 g).

[0400] (1-6) Synthesis of intermediate 6

[0401] Intermediate 3 (0.766 g), intermediate 5 (2 g), tetrakis(triphenylphosphine)palladium (0.115 g), potassium carbonate (0.829 g), toluene (50 mL), ethanol (20 mL), and water (20 mL) were added, and the mixture was stirred at 100 °C for 12 hours. The mixture was washed with methanol and filtered to obtain crude form intermediate 6. Intermediate 6 was used directly in subsequent reactions without further purification.

[0402] (1-7) Synthesis of compound A-6

[0403] Intermediate 6, 1,10-phenanthroline (0.238 g), copper iodide (0.228 g), potassium carbonate (1.106 g), and dimethylacetamide (40 mL) were added, and the mixture was stirred at 160 °C for 16 hours. After filtration with methanol / water, the filter cake was repeatedly dispersed with toluene and washed three times, and then vacuum dried at 140 °C to obtain a green powder. The green powder was purified by sublimation to obtain 90 mg of compound A-6 as a yellow powder. THF was added to the yellow powder to form a slurry, and in this state, mass spectrometry analysis was performed by APSAP (Atmospheric Pressure Solid Sample Probe)-MS to identify the compound (m / z = 634.168, C). 46 H 32 N2O2 + ).

[0404] [Example 2]

[0405] (2) Synthesis of compound A-7

[0406] Compound A-7 was synthesized according to the following synthetic route. Intermediate 5 was synthesized by the method described in Example 1.

[0407] [Chemical Formula 81]

[0408]

[0409] (2-1) Synthesis of intermediate 7

[0410] After adding 2.58 g of 5H-benzofurano[3,2-c]carbazole and 100 mL of dichloromethane and dissolving, 1.78 g of N-bromosuccinimide was added, and the mixture was stirred at room temperature for 20 hours. After extraction with dichloromethane, the result was concentrated. The concentrate was washed with ethanol and filtered to obtain 2.19 g of intermediate 7 as a white powder. The white powder was grown using chloroform and ethanol to obtain single crystals (size: 0.3 mm × 0.06 mm × 0.06 mm). X-ray crystal structure analysis showed that the bromination was located at position 6. Figure 8 The crystal structure obtained by single-crystal X-ray structure analysis is shown. (Unit cell: a=5.6801(8)Å, b=15.309(2)Å, β=96.405(7)o, c=15.0889(19)Å, Z=4, space group: P21)

[0411] (2-2) Synthesis of intermediate 8

[0412] Intermediate 7 (2.15 g), bis(pinacolyl)diboron (1.79 g), the dichloromethane complex of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.261 g), potassium acetate (1.88 g), and dioxane (80 mL) were added, and the mixture was stirred at 90 °C for 12 hours under nitrogen after Ar bubbling. Water was added, and the mixture was extracted with dichloromethane. After distilling off the dichloromethane, the result was washed with a small amount of methanol and heptane and filtered to obtain 1.6 g of intermediate 8.

[0413] (2-3) Synthesis of intermediate 9

[0414] Intermediate 8 (0.76 g), intermediate 5 (0.465 g), tetrakis(triphenylphosphine)palladium (0.031 g), potassium carbonate (0.521 g), dioxane (20 mL), and water (10 mL) were added, and after Ar bubbling, the mixture was stirred at 90 °C for 12 hours under nitrogen. The result was washed with methanol and filtered to obtain 0.368 g of crude intermediate 9 as a gray powder. Intermediate 9 was used directly in subsequent reactions without further purification.

[0415] (2-4) Synthesis of compound A-7

[0416] Intermediate 9 (0.368 g), 1,10-phenanthroline (0.069 g), copper iodide (0.066 g), potassium carbonate (0.321 g), and dimethylacetamide (20 mL) were added, and the mixture was stirred at 160 °C for 3 hours. After filtration with methanol / water, the filter cake was repeatedly dispersed with toluene and washed three times, and then dried under vacuum at 140 °C. Sublimation purification was then performed to obtain 140 mg of compound A-7 as a yellow powder. THF was added to the yellow powder, and the resulting solution was analyzed by UPLC (ultra-high performance liquid chromatography)-MS for identification (m / z = 634.168, C). 46 H 32 N2O2 + ). Figure 9 The normalized emission spectrum of compound A-7 in toluene solution is shown.

[0417] [Example 3]

[0418] (3) Synthesis of compound D-1

[0419] Compound D-1 was synthesized according to the following synthetic route.

[0420] [Chemical Formula 82]

[0421]

[0422] (3-1) Synthesis of intermediate 10

[0423] 1-Bromo-2-iodo-3-nitrobenzene (8.89 g), dibenzo[b,d]furan-4-ylboronic acid (5.75 g), palladium acetate (0.122 g), dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (0.443 g), potassium carbonate (11.2 g), dioxane (200 mL), and water (80 mL) were added, and the mixture was stirred at 80 °C for 3 hours. After extraction with toluene, the result was concentrated. After distillation toluene, the mixture was subjected to silica gel chromatography with chloroform:heptane = 1:2 to obtain 4.9 g of intermediate 10.

[0424] (3-2) Synthesis of intermediate 11

[0425] Intermediate 10 (1.5 g), triethyl phosphite (1.746 mL), and o-dichlorobenzene (80 mL) were added, and the mixture was stirred at 220 °C for 72 hours. After distilling off the o-dichlorobenzene, the mixture was subjected to silica gel chromatography with ethyl acetate:heptane = 1:4 to obtain 0.75 g of intermediate 10 as a white powder.

[0426] (3-3) Synthesis of intermediate 12

[0427] Intermediate 11 (0.75 g), 2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.78 g), triphenylphosphine palladium (55 mg), potassium carbonate (0.62 g), dioxane (80 mL), and water (40 mL) were added, and the mixture was stirred at 80 °C for 8 hours under nitrogen after Ar bubbling. Water was added, and the mixture was extracted with toluene. After distilling off the toluene, the mixture was subjected to silica gel chromatography with ethyl acetate:heptane = 1:3 to obtain 0.95 g of intermediate 12.

[0428] (3-4) Synthesis of intermediate 13

[0429] After adding and dissolving intermediate 12 (0.92 g) and chloroform (80 mL), N-bromosuccinimide (0.374 g) was added, and the mixture was stirred at room temperature for 20 hours. After distilling off the chloroform, the mixture was subjected to silica gel chromatography with ethyl acetate:heptane = 1:3 to obtain 0.76 g of intermediate 13 as a white powder.

[0430] (3-5) Synthesis of intermediate 14

[0431] Intermediate 13 (0.72 g), bis(pinacolyl)diboron (0.453 g), the dichloromethane complex of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (33 mg), potassium acetate (0.403 g), and dioxane (30 mL) were added, and the mixture was stirred at 90 °C for 12 hours under nitrogen after Ar bubbling. Water was added, and the mixture was extracted with ethyl acetate. After distilling off the ethyl acetate, silica gel chromatography with ethyl acetate:heptane = 1:4 was performed to obtain 0.351 g of intermediate 14.

[0432] (3-6) Synthesis of intermediate 15

[0433] Intermediate 14 (0.34 g), intermediate 5 (0.140 g), tetrakis(triphenylphosphine)palladium (16 mg), potassium carbonate (0.160 g), dioxane (20 mL), and water (10 mL) were added, and after Ar bubbling, the mixture was stirred at 90 °C for 12 hours under nitrogen. The result was washed with methanol and filtered to obtain 0.530 g of crude intermediate 15, which was then subjected to silica gel chromatography with ethyl acetate:heptane = 1:2 to obtain 0.271 g of intermediate 15.

[0434] (3-7) Synthesis of compound D-1

[0435] Intermediate 15 (0.271 g), 1,10-phenanthroline (0.054 g), copper iodide (0.051 g), potassium carbonate (0.240 g), and dimethylacetamide (10 mL) were added, and the mixture was stirred at 150 °C for 10 hours. After filtration with water, chlorobenzene was added to the filter cake, and the mixture was melted by heating and filtered through silica gel. After concentration, chlorobenzene was added again, the mixture was melted by heating and cooled, and the precipitate was filtered. The mixture was dried under vacuum at 140 °C to obtain 31 mg of compound D-1 as a yellow powder. Mass spectrometry analysis by MALDI-MS was performed for identification (m / z = 1010.48, C). 74 H 62 N2O2). Figure 10 The normalized emission spectrum of compound D-1 in toluene solution is shown.

[0436] [Example 4]

[0437] (4) Synthesis of compound D-2

[0438] Compound D-2 was synthesized in the same manner as compound D-1, except that 2-([1,1':3',1'':3'',1''':3''',1''''-pentaphenyl]-5''-yl)-4,4,5,5-tetramethyl-1,3,2-dioxoboronalane was used instead of 2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxoboronalane. Figure 11 The normalized emission spectrum of compound D-2 in toluene solution is shown.

[0439] [Example 5 (Fabrication and Evaluation of Organic Light-Emitting Element)]

[0440] An organic light-emitting element is manufactured in which an anode, a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), a light-emitting layer (EML), a hole blocking layer (HBL), an electron transport layer (ETL), and a cathode are sequentially formed on a substrate.

[0441] A glass substrate with a 100 nm thick ITO film as an anode, formed by sputtering, was used as a transparent conductive support substrate (ITO substrate). Next, the glass substrate with the ITO film was ultrasonically cleaned sequentially with acetone and isopropanol (IPA), then cleaned by boiling in IPA, and finally dried. Next, the glass substrate was subjected to UV / ozone cleaning. This treated glass substrate was used as the transparent conductive support substrate.

[0442] Next, by passing through a vacuum chamber at 10 -5 Vacuum evaporation using Pa resistance heating is used to continuously form a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and a metal electrode layer, resulting in an electrode area of ​​3 mm². 2 The layer structure is shown below.

[0443] [Table 6]

[0444]

[0445] Next, the organic light-emitting element is covered with a protective glass plate in a dry air atmosphere and sealed with an acrylic resin adhesive to prevent the element from deteriorating due to moisture absorption. In this way, the organic light-emitting element is obtained.

[0446] For the obtained organic light-emitting elements (OLEDs), their characteristics were measured and evaluated. The OLEDs were tested at a current density of 10 mA / cm². 2 The external quantum yield (EQE) is 7.1%.

[0447] Furthermore, at a current density of 20 mA / cm² 2A continuous operation test was conducted to determine the time (LT80) it took for the brightness to decrease by 20% from the initial brightness. When the time taken for the brightness to decrease by 20% in Comparative Example 1 was set to 1.0, the relative value of LT80 in this example was 2.24.

[0448] Specifically, the current-voltage characteristics are measured using a DC voltage and current source / monitor 6253 manufactured by ADC Corporation, and the luminous intensity is measured using a spectroradiometer SR-LEDW manufactured by Topcon Corporation.

[0449] [Example 6, Comparative Example 1 (Manufacturing and Evaluation of Organic Light-Emitting Element)]

[0450] In Example 6, the organic light-emitting element was manufactured in the same manner as in Example 5, except that compound A-6 was replaced with compound A-7. In Comparative Example 1, the organic light-emitting element was manufactured in the same manner as in Example 3, except that compound A-6 was replaced with compound Ref-1. The characteristics of the manufactured organic light-emitting elements were measured and evaluated in the same manner as in Example 3. The results are shown in Table 7.

[0451] [Table 7]

[0452]

[0453] Table 7 shows that the relative values ​​of LT80 for the organic light-emitting elements of Examples 5 and 6 are 2.24 and 1.45, respectively. Therefore, the organic light-emitting elements comprising the organic compound according to the present invention exhibit high durability. The EQE of the organic light-emitting element of Comparative Example 1 is 5.8%, while the EQEs of the organic light-emitting elements of Examples 5 and 6 are 7.1% and 6.1%, respectively. Therefore, it is demonstrated that the organic light-emitting elements comprising the organic compound according to the present invention also possess high luminous efficiency.

[0454] As described above, the organic compound according to the present invention is an organic compound with high thermal stability. The organic compound according to one embodiment of the present invention exhibits particularly high oscillator strength. Therefore, the organic light-emitting element comprising the organic compound according to the present invention is an organic light-emitting element with high luminous efficiency. Furthermore, the organic light-emitting element comprising the organic compound according to the present invention is an organic light-emitting element with high element durability.

[0455] The present invention may also have the following configuration.

[0456] (Component 1)

[0457] Organic compounds represented by general formula (1-1) or (1-2).

[0458] [Chemical Formula 83]

[0459]

[0460] In general formula (1-1), the bonding site R a To R h At least four of the bonds are attached to the backbone selected from structure group A. At the bonding site R... a To R h In this context, the bonding sites not bonded to structure group A are each independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted silyl group, and cyano group.

[0461] In general formula (1-2), the bonding site R i To R p At least four of the bonds are attached to the backbone selected from structure group A. At the bonding site R... i To R p In this context, the bonding sites not bonded to structure group A are each independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted silyl group, and cyano group. X is an oxygen atom, sulfur atom, NR... 91 CR 92 R 93 or SiR 94 R 95 R 91 To R 95 Each is independently selected from the group consisting of: hydrogen atoms, deuterium atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heterocyclic groups.

[0462] [Chemical Formula 84]

[0463] Structure A Group

[0464]

[0465] In general formulas (2-1) to (2-10), R 1 To R 90Each is independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted silyl group, and cyano group. X is oxygen atom, sulfur atom, NR 91 CR 92 R 93 or SiR 94 R 95 R 91 To R 95 Each group is independently selected from the following groups: hydrogen atom, deuterium atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group. Bonding position. Indicates bonding to the bonding site R a To R p The location.

[0466] (Component 2)

[0467] According to the organic compound constituting 1, wherein in the general formula (1-1), the bonding site R a To R h The four bonds in the structure are selected from the skeleton of structure group A, and in general formula (1-2), the bonding sites R i To R p The four bonds in the structure are selected from the skeleton of structure group A.

[0468] (Component 3)

[0469] Based on the organic compounds constituting 1 or 2, wherein in the organic compounds represented by general formula (1-1), the bonding site R b R c R f and R g Bonded to a skeleton selected from structure group A.

[0470] (Component 4)

[0471] According to any one of 1 to 3, the organic compound represented by general formula (1-1) is bonded to general formula (2-1), (2-2), (2-4), (2-5), (2-6), (2-7), (2-8), (2-9) or (2-10).

[0472] (Component 5)

[0473] According to any one of 1 to 4, the organic compound represented by general formula (1-1) is bonded to general formula (2-1), (2-5), (2-6), (2-7) or (2-8).

[0474] (Composition 6)

[0475] According to any one of the organic compounds constituting 1 to 5, wherein the organic compound represented by general formula (1-1) is represented by general formula (3-6) or (3-7).

[0476] [Chemical Formula 85]

[0477]

[0478] In general formulas (3-6) and (3-7), the bonding site R a R d R e and R h Each is independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, and cyano group. 46 To R 63 Each is independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted silyl and cyano.

[0479] X represents an oxygen atom, a sulfur atom, and NR. 91 CR 92 R 93 or SiR 94 R 95 R 91 To R 95 Each is independently selected from the group consisting of: hydrogen atoms, deuterium atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heterocyclic groups.

[0480] (Component 7)

[0481] According to the organic compounds constituting 6, wherein in general formulas (3-6) and (3-7), R 46 To R 63 Each is independently selected from the group consisting of: hydrogen atoms, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, and substituted or unsubstituted heterocyclic groups having 3 to 24 carbon atoms.

[0482] (Composition 8)

[0483] According to the organic compounds constituting 7, wherein in general formulas (3-6) and (3-7), R 46 To R63 It is a hydrogen atom.

[0484] (Composition 9)

[0485] Based on the organic compounds constituting 1 or 2, wherein in the organic compounds represented by general formulas (1-2), the bonding site R j R k R n and R o Bonded to a skeleton selected from structure group A.

[0486] (Composition 10)

[0487] According to the organic compounds constituting any one of 1, 2 and 9, wherein the organic compounds represented by general formula (1-2) are bonded to general formula (2-6).

[0488] (Composition 11)

[0489] According to the organic compounds constituting any one of 1, 2, 9 and 10, wherein the organic compounds represented by general formula (1-2) are represented by general formula (4-2).

[0490] [Chemical Formula 86]

[0491]

[0492] In general formula (4-2), the bonding site R i R l R m and R p Each is independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, and cyano group. 46 To R 54 Each is independently selected from the following groups: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, and cyano group. X is oxygen atom, sulfur atom, NR 91 CR 92 R 93 or SiR 94 R 95 R 91 To R 95 Each is independently selected from the group consisting of: hydrogen atoms, deuterium atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heterocyclic groups.

[0493] (Composition 12)

[0494] Based on the organic compounds constituting 11, wherein in general formula (4-2), R46 To R 54 Each is independently selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, and substituted or unsubstituted heterocyclic groups having 3 to 24 carbon atoms.

[0495] (Composition 13)

[0496] Based on the organic compounds constituting 11 or 12, wherein in general formula (4-2), R 46 To R 54 It is a hydrogen atom.

[0497] (Composition 14)

[0498] An organic light-emitting element comprising:

[0499] First electrode and second electrode; and

[0500] An organic compound layer disposed between the first and second electrodes

[0501] The organic compound layer contains organic compounds according to any one of constituents 1 to 13.

[0502] (Composition 15)

[0503] According to the organic light-emitting element constituting 14, wherein the organic compound layer includes a light-emitting layer, and

[0504] The light-emitting layer contains organic compounds.

[0505] (Composition 16)

[0506] According to the organic light-emitting element constituting 15, wherein the light-emitting layer further comprises a first compound, and

[0507] The lowest excited singlet state energy of the first compound is higher than that of the organic compound.

[0508] (Composition 17)

[0509] According to the organic light-emitting element constituting 16, wherein the first compound includes a fused polycyclic hydrocarbon compound.

[0510] (Composition 18)

[0511] According to the organic light-emitting element constituting 16 or 17, wherein the light-emitting layer further comprises a second compound, and

[0512] The lowest excited singlet state energy of the second compound is higher than that of the organic compound but lower than that of the first compound.

[0513] (Composition 19)

[0514] A display device comprising a plurality of pixels, wherein at least one of the plurality of pixels includes an organic light-emitting element and a transistor connected to the organic light-emitting element, according to any one of 14 to 18.

[0515] (Composition 20)

[0516] A photoelectric conversion device includes: an imaging element configured to receive light; and a display unit configured to display an image captured by the imaging element.

[0517] The display section includes an organic light-emitting element according to any one of 14 to 18.

[0518] (Composition 21)

[0519] An image display device includes: a display section comprising an organic light-emitting element constituting any one of 14 to 18; and a housing on which the display section is disposed.

[0520] (Composition 22)

[0521] An electronic device includes: a display unit including an organic light-emitting element configured according to any one of 14 to 18; a housing on which the display unit is disposed; and a communication unit disposed in the housing and configured to communicate with an external unit.

[0522] (Composition 23)

[0523] A wearable device includes: a display unit including an organic light-emitting element according to any one of 14 to 18; an optical system configured to collect light from the display unit; and a controller configured to control the display of the display unit.

[0524] (Composition 24)

[0525] A lighting device comprising: a light source including an organic light-emitting element comprising any one of 14 to 18; and a housing provided with the light source.

[0526] (Composition 25)

[0527] A mobile body includes: a luminaire comprising an organic light-emitting element constituting any one of 14 to 18; and a body provided with the luminaire.

[0528] (Composition 26)

[0529] An image forming apparatus includes: a photoreceptor; and an exposure light source configured to expose the photoreceptor.

[0530] The light source for exposure includes an organic light-emitting element according to any one of 14 to 18.

[0531] This invention is not limited to the embodiments described above, and various changes and modifications can be made without departing from the spirit and scope of the invention. Therefore, the claims are appended to disclose the scope of the invention.

[0532] This application claims priority to Japanese Patent Application No. 2023-112256, filed July 7, 2023, and Japanese Patent Application No. 2024-083867, filed May 23, 2024, the entire contents of which are incorporated herein by reference.

[0533] Explanation of reference numerals in the attached figures

[0534] 1. Interlayer insulation layer

[0535] 2. Reflecting electrode

[0536] 3 Insulation layer

[0537] 4. Organic compound layer

[0538] 5 Transparent Electrodes

[0539] 6. Protective layer

[0540] 7 Color Filters

[0541] 10 subpixels

[0542] 11 base plate

[0543] 12 Insulation layer

[0544] 13. Gate electrode

[0545] 14. Grid insulating film

[0546] 15 Semiconductor Layer

[0547] 16 Drain electrode

[0548] 17 Source Electrode

[0549] 18 Thin-film transistors

[0550] 19 Insulating film

[0551] 20 Contact Holes

[0552] 21 Lower electrode

[0553] 22 Organic compound layer

[0554] 23 Upper electrode

[0555] 24 First protective layer

[0556] 25 Second protective layer

[0557] 26 Organic light-emitting elements

[0558] 27 Photoreceptors

[0559] 28 Exposure Light Source

[0560] 29 Light

[0561] 30 Charging Unit

[0562] 31. Developing Department

[0563] 32 Transfer Section

[0564] 33 Conveying Department

[0565] 34 Recording media

[0566] 35 Fixing section

[0567] 36 Light-emitting part

[0568] 37. The first direction parallel to the long axis of the photoreceptor

[0569] 40 Image forming apparatus

[0570] 100 display devices

[0571] 1000 display devices

[0572] 1001 Top Cover

[0573] 1002 Flexible Printed Circuit

[0574] 1003 Touch Panel

[0575] 1004 Flexible Printed Circuit

[0576] 1005 Display Panel

[0577] 1006 Framework

[0578] 1007 Circuit Board

[0579] 1008 battery

[0580] 1009 bottom cover

[0581] 1100 camera equipment

[0582] 1101 Viewfinder

[0583] 1102 rear monitor

[0584] 1103 Operations Department

[0585] 1104 Housing

[0586] 1200 electronic devices

[0587] 1201 Display Department

[0588] 1202 Operations Department

[0589] 1203 Casing

[0590] 1300 display devices

[0591] 1301 Framework

[0592] 1302 Display Section

[0593] 1303 Abutment

[0594] 1310 Display Device

[0595] 1311 First Display Section

[0596] 1312 Second Display Unit

[0597] 1313 Casing

[0598] 1314 Bending point

[0599] 1400 Lighting Equipment

[0600] 1401 Housing

[0601] 1402 Light Source

[0602] 1403 Circuit Board

[0603] 1404 optical film

[0604] 1405 Light Diffuser Section

[0605] 1500 cars

[0606] 1501 taillights

[0607] Window 1502

[0608] 1503 Car Body

[0609] 1600 Smart Glasses

[0610] 1601 Lens

[0611] 1602 Camera Equipment

[0612] 1603 Controller

[0613] 1610 Smart Glasses

[0614] 1611 Lens

[0615] 1612 Controller

Claims

1. An organic compound represented by general formula (1-1) or (1-2): [Chemical Formula 1] In general formula (1-1), the bonding site R a To R h At least four of the bonds are attached to the skeleton selected from structure group A; and at the bonding site R a To R h In this configuration, the bonding sites not bonded to structure group A are each independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted silyl group, and cyano group. In general formula (1-2), the bonding site R i To R p At least four of the bonds are attached to the skeleton selected from structure group A; at the bonding site R i To R p In this configuration, the bonding sites not bonded to structure group A are each independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted silyl group, and cyano group; and X is oxygen atom, sulfur atom, NR group, and NR group. 91 CR 92 R 93 or SiR 94 R 95 , where R 91 To R 95 Each is independently selected from the group consisting of: hydrogen atoms, deuterium atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heterocyclic groups. [Chemical Formula 2] Structure A Group In general formulas (2-1) to (2-10), R 1 To R 90 Each is independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted silyl group, and cyano group; X is oxygen atom, sulfur atom, NR 91 CR 92 R 93 or SiR 94 R 95 , where R 91 To R 95 Each is independently selected from the group consisting of: hydrogen atom, deuterium atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group; and the bonding position Indicates bonding to the bonding site R a To R p The location.

2. The organic compound according to claim 1, wherein in general formula (1-1), the bonding site R a To R h The four bonds in the structure are selected from the skeleton of structure group A, and in general formula (1-2), the bonding sites R i To R p The four bonds in the structure are selected from the skeleton of structure group A.

3. The organic compound according to claim 1, wherein in the organic compound represented by general formula (1-1), the bonding site R b R c R f and R g Bonded to a skeleton selected from structure group A.

4. The organic compound according to claim 1, wherein the organic compound represented by general formula (1-1) is bonded to general formula (2-1), (2-2), (2-4), (2-5), (2-6), (2-7), (2-8), (2-9) or (2-10).

5. The organic compound according to claim 1, wherein the organic compound represented by general formula (1-1) is bonded to general formula (2-1), (2-5), (2-6), (2-7) or (2-8).

6. The organic compound according to claim 1, wherein the organic compound represented by general formula (1-1) is represented by general formula (3-6) or (3-7): [Chemical Formula 3] In general formulas (3-6) and (3-7), the bonding site R a R d R e and R h Each is independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, and cyano group; R 46 To R 63 Each is independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted silyl group, and cyano group; and X represents an oxygen atom, a sulfur atom, and NR. 91 CR 92 R 93 or SiR 94 R 95 , where R 91 To R 95 Each is independently selected from the group consisting of: hydrogen atoms, deuterium atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heterocyclic groups.

7. The organic compound according to claim 6, wherein in general formulas (3-6) and (3-7), R 46 To R 63 Each is independently selected from the group consisting of: hydrogen atoms, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, and substituted or unsubstituted heterocyclic groups having 3 to 24 carbon atoms.

8. The organic compound according to claim 7, wherein in general formulas (3-6) and (3-7), R 46 To R 63 It is a hydrogen atom.

9. The organic compound according to claim 1, wherein in the organic compound represented by general formulas (1-2), the bonding site R j R k R n and R o Bonded to a skeleton selected from structure group A.

10. The organic compound according to claim 1, wherein the organic compound represented by general formula (1-2) is bonded to general formula (2-6).

11. The organic compound according to claim 1, wherein the organic compound represented by general formula (1-2) is represented by general formula (4-2): [Chemical Formula 4] In general formula (4-2), the bonding site R i R l R m and R p Each is independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, and cyano group; R 46 To R 54 Each is independently selected from the group consisting of: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, and cyano group; and X is oxygen atom, sulfur atom, NR 91 CR 92 R 93 or SiR 94 R 95 , where R 91 To R 95 Each is independently selected from the group consisting of: hydrogen atoms, deuterium atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heterocyclic groups.

12. The organic compound according to claim 11, wherein in general formula (4-2), R 46 To R 54 Each is independently selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, and substituted or unsubstituted heterocyclic groups having 3 to 24 carbon atoms.

13. The organic compound according to claim 11, wherein in general formula (4-2), R 46 To R 54 It is a hydrogen atom.

14. An organic light-emitting element, comprising: First electrode and second electrode; as well as An organic compound layer disposed between the first electrode and the second electrode, The organic compound layer thereon comprises the organic compound according to claim 1.

15. The organic light-emitting element according to claim 14, wherein the organic compound layer comprises a light-emitting layer, and The light-emitting layer contains the organic compound.

16. The organic light-emitting element of claim 15, wherein the light-emitting layer further comprises a first compound, and The lowest excited singlet state energy of the first compound is higher than that of the organic compound.

17. The organic light-emitting element according to claim 16, wherein the first compound comprises a fused polycyclic hydrocarbon compound.

18. The organic light-emitting element of claim 16, wherein the light-emitting layer further comprises a second compound, and The lowest excited singlet state energy of the second compound is higher than that of the organic compound and lower than that of the first compound.

19. A display device comprising a plurality of pixels, wherein at least one of the plurality of pixels comprises an organic light-emitting element according to any one of claims 14 to 18 and a transistor connected to the organic light-emitting element.

20. A photoelectric conversion device, comprising: An imaging element configured to receive light; and a display unit configured to display an image captured by the imaging element. The display unit includes an organic light-emitting element according to any one of claims 14 to 18.

21. An image display device, comprising: A display portion comprising an organic light-emitting element according to any one of claims 14 to 18; and a housing in which the display unit is provided.

22. An electronic device comprising: A display portion comprising an organic light-emitting element according to any one of claims 14 to 18; The housing is provided with the display unit; And a communication unit disposed in the housing and configured to communicate with external units.

23. A wearable device comprising: A display unit comprising an organic light-emitting element according to any one of claims 14 to 18; and an optical system configured to collect light from the display unit; And a controller configured to control the display of the display unit.

24. A lighting device comprising: A light source comprising an organic light-emitting element according to any one of claims 14 to 18; and a housing in which the light source is provided.

25. A mobile body comprising: Luminaires comprising organic light-emitting elements according to any one of claims 14 to 18; and the body on which the lamps are installed.

26. An image forming apparatus comprising: Photoreceptor; and an exposure light source configured to expose the photoreceptor. The exposure light source includes an organic light-emitting element according to any one of claims 14 to 18.

Images