Compound, organic electroluminescence element, and electronic device

Abstract

The present application relates to a compound, an organic electroluminescence element, and an electronic device. The present application provides a compound represented by General Formula (1C-A) below. In General Formula (1C-A) above, one of R4 to R8 and R 10 ~R 12 is a group represented by General Formula (1D-A) above, R1 to R3, R9, and the remaining R4 to R8 and R 10 ~R 12 are a hydrogen atom or a substituent, and the like, wherein at least one of R 21 ~R 30 is a group other than a hydrogen atom, in the case where R 11 is a group represented by General Formula (1D) above, R 12 is a hydrogen atom or a phenyl group, in the case where R 12 is a group represented by General Formula (1D) above, R 11 is a hydrogen atom or a phenyl group, in General Formula (1D) above, one of R 21 ~R 30 indicates a bonding position to a benzo[a]anthracene ring in General Formula (1C) above, and the remaining R 21 ~R 30 in General Formula (1D) above that does not form a ring are a hydrogen atom or a substituent, and the like.

Description

[0001] This application is a divisional application of the application filed on December 26, 2022, with application number 202280085898.X and entitled "Compounds, Organic Electroluminescent Elements and Electronic Devices". Technical Field

[0002] This invention relates to compounds, organic electroluminescent elements, and electronic devices. Background Technology

[0003] Organic electroluminescent devices (hereinafter sometimes referred to as "organic EL devices") are used in full-color displays for mobile phones, televisions, and other applications. When a voltage is applied to an organic EL device, holes are injected from the anode into the emitting layer, and electrons are injected from the cathode into the emitting layer. Then, in the emitting layer, the injected holes recombine with the electrons to form excitons. At this point, according to the statistical law of electron spin, singlet excitons are generated at a rate of 25%, and triplet excitons are generated at a rate of 75%.

[0004] To improve the performance of organic EL devices, various studies have been conducted on compounds used in organic EL devices (see, for example, Patent Document 1 and Patent Document 2). Performance characteristics of organic EL devices include, for example, brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime.

[0005] Existing technical documents

[0006] Patent documents

[0007] Patent Document 1: International Publication No. 2021 / 132535

[0008] Patent Document 2: International Publication No. 2009 / 081774 Summary of the Invention

[0009] The problem the invention aims to solve

[0010] One of the objectives of this invention is to provide a compound that can improve the lifetime of an organic electroluminescent element, an organic electroluminescent element containing the compound, and an electronic device equipped with the organic electroluminescent element.

[0011] In addition, one of the other objects of the present invention is to provide an organic electroluminescent element with improved lifespan and an electronic device equipped with the organic electroluminescent element.

[0012] means for solving problems

[0013] According to one aspect of the present invention, a compound represented by the following general formula (1C-A) is provided.

[0014]

Chemical Formula 1

[0015]

[0016] (In the above general formula (1C-A),

[0017] R4~R8 and R 10 ~R 12 One of them is a group represented by the general formula (1D-A) above.

[0018] R1 to R3, R9, and R4 to R8 and R9 other than the groups shown in the above general formula (1D-A). 10 ~R 12 Each independently

[0019] hydrogen atom,

[0020] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0021] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0022] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0023] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0024] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0025] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0026] -O-(R 904 The groups shown in the figure,

[0027] -S-(R 905 The groups shown in the figure,

[0028] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0029] -C(=O)R 801 The groups shown

[0030] -COOR 802 The groups shown

[0031] Halogen atoms,

[0032] cyano,

[0033] Nitro,

[0034] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0035] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0036] In R 11 In the case of a group represented by the above general formula (1D-A), R 12 A phenyl group consisting of a hydrogen atom or with or without substitution.

[0037] In R 12 In the case of a group represented by the above general formula (1D-A), R 11 A phenyl group consisting of a hydrogen atom or with or without substitution.

[0038] In the above general formula (1D-A), R 21 ~R 30 One of them represents the bonding position with the benzo[a]anthracene ring in the above general formula (1C-A), and the R in the above general formula (1D-A) is not at that bonding position. 21 ~R 30 One or more groups consisting of two or more adjacent elements.

[0039] They bond together to form substituted or unsubstituted monocyclic rings.

[0040] They bond together to form substituted or unsubstituted fused rings, or

[0041] They do not bond with each other.

[0042] The R in the above general formula (1D-A) is not at the bonding position of the benzo[a]anthracene ring in the above general formula (1C-A), does not form the above-mentioned substituted or unsubstituted monocyclic ring, and does not form the above-mentioned substituted or unsubstituted fused ring. 21 ~R 30 Each independently

[0043] hydrogen atom,

[0044] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0045] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0046] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0047] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0048] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0049] -O-(R 904 The groups shown in the figure,

[0050] -S-(R905 The groups shown in the figure,

[0051] -N(R 906 (R) 907 The groups shown in the figure,

[0052] Halogen atoms,

[0053] cyano,

[0054] Nitro,

[0055] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0056] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0057] Among them, R 21 ~R 30 At least one of them is a group other than a hydrogen atom.

[0058] In the compounds represented by the above general formula (1C-A), R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently

[0059] hydrogen atom,

[0060] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0061] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0062] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0063] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0064] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.

[0065] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.

[0066] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.

[0067] In R904 In the case of multiple Rs, multiple Rs 904 They are the same or different.

[0068] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.

[0069] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.

[0070] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.

[0071] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[0072] In R 802 In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)

[0073] According to one aspect of the present invention, a compound represented by the following general formula (1C-B) is provided.

[0074]

Chemical Formula 2

[0075]

[0076] (In the above general formula (1C-B),

[0077] R4~R6, R8 and R 10 ~R 12 One of them is a group represented by the general formula (1D-B) above.

[0078] R1–R3, R7, R9, and R4–R6, R8, and R9, excluding the groups shown in the above general formula (1D-B). 10 ~R 12 Each independently

[0079] hydrogen atom,

[0080] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0081] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0082] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0083] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0084] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0085] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0086] -O-(R 904 The groups shown in the figure,

[0087] -S-(R 905 The groups shown in the figure,

[0088] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0089] -C(=O)R 801 The groups shown

[0090] -COOR 802 The groups shown

[0091] Halogen atoms,

[0092] cyano,

[0093] Nitro,

[0094] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0095] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0096] In R 11 In the case of a group represented by the above general formula (1D-B), R 12 It is a hydrogen atom or an unsubstituted phenyl group.

[0097] In R 12 In the case of a group represented by the above general formula (1D-B), R 11 For substituted or unsubstituted phenyl groups,

[0098] In the above general formula (1D-B), R 21 ~R 30 One of them represents the bonding position with the benzo[a]anthracene ring in the above general formula (1C-B), and the R in the above general formula (1D-B) is not at that bonding position. 21 ~R 30 One or more groups consisting of two or more adjacent elements.

[0099] They bond together to form substituted or unsubstituted monocyclic rings.

[0100] They bond together to form substituted or unsubstituted fused rings, or

[0101] They do not bond with each other.

[0102] The R in the above general formula (1D-B) is not at the bonding position with the benzo[a]anthracene ring in the above general formula (1C-B), does not form the above-mentioned substituted or unsubstituted monocyclic ring, and does not form the above-mentioned substituted or unsubstituted fused ring. 21 ~R 30 Each independently

[0103] hydrogen atom,

[0104] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0105] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0106] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0107] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0108] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0109] -O-(R 904 The groups shown in the figure,

[0110] -S-(R 905 The groups shown in the figure,

[0111] -N(R 906 (R) 907 The groups shown in the figure,

[0112] Halogen atoms,

[0113] cyano,

[0114] Nitro,

[0115] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0116] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0117] In the compounds represented by the above general formula (1C-B), R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently

[0118] hydrogen atom,

[0119] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0120] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0121] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0122] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0123] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.

[0124] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.

[0125] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.

[0126] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.

[0127] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.

[0128] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.

[0129] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.

[0130] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[0131] In R 802 In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)

[0132] According to one aspect of the present invention, a compound represented by the following general formula (1C-C) is provided.

[0133]

Chemical Formula 3

[0134]

[0135] (In the above general formula (1C-C),

[0136] R4~R8 and R 10 ~R 12 One of them is a group represented by the general formula (1D-C) above.

[0137] R1 to R3, R9, and R4 to R8 and R9 other than the groups shown in the above general formula (1D-C). 10 ~R 12 Each independently

[0138] hydrogen atom,

[0139] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0140] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0141] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0142] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0143] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0144] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0145] -O-(R 904 The groups shown in the figure,

[0146] -S-(R 905 The groups shown in the figure,

[0147] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0148] -C(=O)R 801 The groups shown

[0149] -COOR 802 The groups shown

[0150] Halogen atoms,

[0151] cyano,

[0152] Nitro,

[0153] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0154] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0155] In R11 In the case of a group represented by the above general formula (1D-C), R 12 A phenyl group consisting of a hydrogen atom or with or without substitution.

[0156] In R 12 In the case of a group represented by the above general formula (1D-C), R 11 A phenyl group consisting of a hydrogen atom or with or without substitution.

[0157] In the above general formula (1D-C), R 22 R 23 R 25 R 27 R 28 and R 30 One of them represents the bonding position with the benzo[a]anthracene ring in the above general formula (1C-C), and is represented by R. 21 R 24 R 26 and R 29 And R in the above general formula (1D-C) that is not at the bonding site. 22 R 23 R 25 R 27 R 28 and R 30 One or more groups consisting of two or more adjacent elements.

[0158] They bond together to form substituted or unsubstituted monocyclic rings.

[0159] They bond together to form substituted or unsubstituted fused rings, or

[0160] They do not bond with each other.

[0161] The R in the above general formula (1D-C) is not at the bonding position with the benzo[a]anthracene ring in the above general formula (1C-C), does not form the above-mentioned substituted or unsubstituted monocyclic ring, and does not form the above-mentioned substituted or unsubstituted fused ring. 21 ~R 30 Each independently

[0162] hydrogen atom,

[0163] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0164] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0165] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0166] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0167] -Si(R901 (R) 902 (R) 903 The groups shown in the figure,

[0168] -O-(R 904 The groups shown in the figure,

[0169] -S-(R 905 The groups shown in the figure,

[0170] -N(R 906 (R) 907 The groups shown in the figure,

[0171] Halogen atoms,

[0172] cyano,

[0173] Nitro,

[0174] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0175] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0176] In the compounds represented by the above general formula (1C-C), R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently

[0177] hydrogen atom,

[0178] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0179] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0180] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0181] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0182] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.

[0183] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.

[0184] In R 903In the case of multiple Rs, multiple Rs 903 They are the same or different.

[0185] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.

[0186] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.

[0187] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.

[0188] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.

[0189] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[0190] In R 802 In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)

[0191] According to one aspect of the present invention, an organic electroluminescent element containing a compound according to one aspect of the present invention is provided.

[0192] According to one aspect of the present invention, an organic electroluminescent element is provided, having an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein at least one layer of the organic layer contains a compound according to one aspect of the present invention.

[0193] According to one aspect of the present invention, an organic electroluminescent element is provided, having an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer having a light-emitting region, the light-emitting region comprising a first light-emitting layer and a second light-emitting layer, the first light-emitting layer containing a first compound represented by the following general formula (1C), and the second light-emitting layer containing a second compound.

[0194] [Chemical Formula 4]

[0195]

[0196] (In the above general formula (1C),

[0197] R4~R8 and R 10 ~R 12 One of them is a group represented by the general formula (1D) above.

[0198] R1 to R3, R9, and R4 to R8 and R9 other than the groups shown in the above general formula (1D). 10 ~R 12 Each independently

[0199] hydrogen atom,

[0200] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0201] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0202] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0203] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0204] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0205] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0206] -O-(R 904 The groups shown in the figure,

[0207] -S-(R 905 The groups shown in the figure,

[0208] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0209] -C(=O)R 801 The groups shown

[0210] -COOR 802 The groups shown

[0211] Halogen atoms,

[0212] cyano,

[0213] Nitro,

[0214] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0215] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0216] In R 11 In the case of a group represented by the above general formula (1D), R 12 A phenyl group consisting of a hydrogen atom or with or without substitution.

[0217] In R 12In the case of a group represented by the above general formula (1D), R 11 A phenyl group consisting of a hydrogen atom or with or without substitution.

[0218] In the above general formula (1D), R 21 ~R 30 One of them represents the bonding position with the benzo[a]anthracene ring in the above general formula (1C), and the R in the above general formula (1D) is not at that bonding position. 21 ~R 30 One or more groups consisting of two or more adjacent elements.

[0219] They bond together to form substituted or unsubstituted monocyclic rings.

[0220] They bond together to form substituted or unsubstituted fused rings, or

[0221] They do not bond with each other.

[0222] The R in the above general formula (1D) is not bonded to the benzo[a]anthracene ring in the above general formula (1C), does not form the above-mentioned substituted or unsubstituted monocyclic ring, and does not form the above-mentioned substituted or unsubstituted fused ring. 21 ~R 30 Each independently

[0223] hydrogen atom,

[0224] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0225] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0226] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0227] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0228] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0229] -O-(R 904 The groups shown in the figure,

[0230] -S-(R 905 The groups shown in the figure,

[0231] -N(R 906 (R) 907 The groups shown in the figure,

[0232] Halogen atoms,

[0233] cyano,

[0234] Nitro,

[0235] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0236] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0237] In the compounds represented by the above general formula (1C), R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently

[0238] hydrogen atom,

[0239] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0240] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0241] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0242] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0243] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.

[0244] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.

[0245] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.

[0246] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.

[0247] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.

[0248] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.

[0249] In R 907 In the case of multiple Rs, multiple Rs907 They are the same or different.

[0250] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[0251] In R 802 In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)

[0252] According to one aspect of the present invention, an electronic device is provided that incorporates an organic electroluminescent element according to one aspect of the present invention.

[0253] According to one aspect of the present invention, a compound capable of improving the lifetime of an organic electroluminescent element, an organic electroluminescent element comprising the compound, and an electronic device equipped with the organic electroluminescent element can be provided.

[0254] In addition, according to one aspect of the present invention, an organic electroluminescent element with improved lifespan and an electronic device equipped with the organic electroluminescent element can be provided. Attached Figure Description

[0255] Figure 1 This is a diagram illustrating the general configuration of an example of an organic electroluminescent element according to one embodiment of the present invention.

[0256] Figure 2 This is a diagram illustrating the general configuration of another example of an organic electroluminescent element according to one embodiment of the present invention. Detailed Implementation

[0257] [definition]

[0258] In this specification, a hydrogen atom means an isotope containing different numbers of neutrons, namely protium, deuterium, and tritium.

[0259] In this specification, the chemical structural formula does not explicitly show that the bonding positions of symbols such as "R" and "D" representing deuterium atoms are set to be bonded to hydrogen atoms, i.e., protium atoms, deuterium atoms, or tritium atoms.

[0260] In this specification, the number of carbon atoms forming a ring refers to the number of carbon atoms in the ring itself of a compound whose atoms are bonded in a ring (e.g., monocyclic compounds, fused-ring compounds, bridged-ring compounds, carbocyclic compounds, and heterocyclic compounds). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of carbon atoms forming the ring. The term "number of carbon atoms forming a ring" is used as such unless otherwise specified. For example, the number of carbon atoms forming a ring is 6 for a benzene ring, 10 for a naphthalene ring, 5 for a pyridine ring, and 4 for a furan ring. Additionally, for example, the number of carbon atoms forming a ring is 13 for 9,9-diphenylfluorene and 25 for 9,9'-spirobifluorene.

[0261] Furthermore, when a benzene ring is substituted with an alkyl group, the carbon number of the alkyl group is not included in the number of carbon atoms in the ring-forming process of the benzene ring. Therefore, the number of carbon atoms in the cyclic benzene ring substituted with an alkyl group is 6. Similarly, when a naphthalene ring is substituted with an alkyl group, the carbon number of the alkyl group is not included in the number of carbon atoms in the ring-forming process of the naphthalene ring. Therefore, the number of carbon atoms in the cyclic naphthalene ring substituted with an alkyl group is 10.

[0262] In this specification, the number of cyclic atoms refers to the number of atoms constituting the ring itself in compounds with a cyclic structure (e.g., monocyclic, fused-ring, and ring assemblies). Atoms that do not constitute the ring (e.g., hydrogen atoms ending the bonds of the ring-forming atoms) and atoms contained in substituents when the ring is substituted are not included in the number of cyclic atoms. The term "number of cyclic atoms" as used below is the same unless otherwise stated. For example, the number of cyclic atoms in a pyridine ring is 6, in a quinazoline ring it is 10, and in a furan ring it is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or atoms constituting substituents are not included in the number of cyclic atoms in pyridine. Therefore, the number of cyclic atoms in a pyridine ring bonded with hydrogen atoms or substituents is 6. Furthermore, hydrogen atoms bonded to the carbon atoms of the quinazoline ring, or atoms constituting substituents, are not included in the number of cyclic atoms of the quinazoline ring. Therefore, the number of cyclic atoms in a quinazoline ring with bonded hydrogen atoms or substituents is 10.

[0263] In this specification, the phrase "ZZ group with substituted or unsubstituted carbon numbers of XX to YY" indicates the number of carbons when the ZZ group is unsubstituted; the number of carbons in substituents is not included. Here, "YY" is greater than "XX," where "XX" refers to an integer greater than 1, and "YY" refers to an integer greater than 2.

[0264] In this specification, the phrase "ZZ group with substituted or unsubstituted atoms of XX to YY" refers to the number of atoms when the ZZ group is unsubstituted, excluding the number of atoms of substituents when substitution has occurred. Here, "YY" is greater than "XX", where "XX" is an integer greater than or equal to 1, and "YY" is an integer greater than or equal to 2.

[0265] In this specification, "unsubstituted ZZ group" means "substituted or unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".

[0266] In this specification, "unsubstituted" when referred to as "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group has not been substituted with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0267] Furthermore, in this specification, "substitution" when expressed as "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group have been replaced by a substituent. Similarly, "substitution" when expressed as "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group have been replaced by an AA group.

[0268] Substituents described in this specification

[0269] The substituents described in this specification are explained below.

[0270] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted aryl group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0271] Unless otherwise stated in this specification, the number of cyclic atoms in the "unsubstituted heterocyclic group" is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0272] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0273] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkenyl group" is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0274] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkynyl group" is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0275] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted cycloalkyl group" is 3 to 50, preferably 3 to 20, and more preferably 3 to 6.

[0276] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted aryl group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0277] Unless otherwise stated in this specification, the number of cyclic atoms in the "unsubstituted divalent heterocyclic group" is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0278] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkylene group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0279] • "Substituted or unsubstituted aryl groups"

[0280] Specific examples of "substituted or unsubstituted aryl" as described in this specification (specific example group G1) include unsubstituted aryl (specific example group G1A) and substituted aryl (specific example group G1B), etc. (Here, unsubstituted aryl refers to the case where "substituted or unsubstituted aryl" is "unsubstituted aryl", and substituted aryl refers to the case where "substituted or unsubstituted aryl" is "substituted aryl".) In this specification, when referred to only as "aryl", both "unsubstituted aryl" and "substituted aryl" are included.

[0281] "Substituted aryl" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl" group have been substituted with a substituent. Examples of "substituted aryl" include the group in Specific Example Group G1A below in which one or more hydrogen atoms of an "unsubstituted aryl" group have been substituted with a substituent, and the substituted aryl group in Specific Example Group G1B below. It should be noted that the examples of "unsubstituted aryl" and "substituted aryl" listed here are only examples. The "substituted aryl" described in this specification also includes the group in Specific Example Group G1B below in which hydrogen atoms bonded to the carbon atom of the aryl group itself have been further substituted with a substituent, and the group in Specific Example Group G1B below in which hydrogen atoms of the substituent have been further substituted with a substituent.

[0282] • Unsubstituted aryl groups (specific example group G1A):

[0283] Phenyl,

[0284] p-phenyl,

[0285] metaphenyl,

[0286] o-biphenylyl,

[0287] p-terphenyl-4-yl,

[0288] p-terphenyl-3-yl,

[0289] p-terphenyl-2-yl,

[0290] m-terphenyl-4-yl,

[0291] m-terphenyl-3-yl,

[0292] m-terphenyl-2-yl,

[0293] o-terphenyl-4-yl,

[0294] o-terphenyl-3-yl,

[0295] o-terphenyl-2-yl,

[0296] 1-naphthyl,

[0297] 2-naphthyl,

[0298] anthryl,

[0299] benzanthryl,

[0300] phenanthryl,

[0301] triphenylenyl,

[0302] phenalenyl,

[0303] pyrenyl,

[0304] chrysenyl,

[0305] benzochrysenyl,

[0306] triphenylenyl,

[0307] benzo triphenylenyl,

[0308] tetracenyl,

[0309] pentacenyl,

[0310] fluorenyl,

[0311] 9,9'-spirobifluorenyl,

[0312] benzofluorenyl,

[0313] dibenzofluorenyl,

[0314] fluoranthenyl,

[0315] benzofluoranthenyl,

[0316] perylenyl and

[0317] The monovalent aryl group is derived by removing one hydrogen atom from the ring structure shown in the following general formulas (TEMP-1) to (TEMP-15).

[0318] [Chemical Formula 5]

[0319]

[0320]

Chemical Formula 6

[0321]

[0322] • Substituted aryl groups (specific example group G1B):

[0323] o-Tolyl,

[0324] m-Tolyl,

[0325] p-Tolyl,

[0326] p-Xylyl,

[0327] m-Xylyl,

[0328] o-xylyl,

[0329] p-isopropylphenyl,

[0330] m-Isopropylphenyl,

[0331] o-isopropylphenyl,

[0332] p-tert-butylphenyl,

[0333] m-tert-butylphenyl,

[0334] o-tert-butylphenyl,

[0335] 3,4,5-Trimethylphenyl

[0336] 9,9-Dimethylfluorenyl,

[0337] 9,9-Diphenylfluorenyl,

[0338] 9,9-Bis(4-methylphenyl)fluorenyl,

[0339] 9,9-Bis(4-isopropylphenyl)fluorenyl,

[0340] 9,9-Bis(4-tert-butylphenyl)fluorenyl,

[0341] cyanophenyl,

[0342] Triphenylsilylphenyl

[0343] Trimethylsilylphenyl

[0344] Phenynaphthyl,

[0345] Naphthylphenyl and

[0346] A group derived from the ring structure shown in the above general formulas (TEMP-1) to (TEMP-15) by substitution of one or more hydrogen atoms of a monovalent group with a substituent.

[0347] • "Substituted or unsubstituted heterocyclic groups"

[0348] The term "heterocyclic group" as used in this specification refers to a cyclic group whose cyclic atoms contain at least one heteroatom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.

[0349] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.

[0350] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0351] Specific examples of "substituted or unsubstituted heterocyclic groups" described in this specification (specific example group G2) include unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B), etc. (Here, unsubstituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group", and substituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group".) In this specification, the term "heterocyclic group" includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".

[0352] "Substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" have been substituted with a substituent. Specific examples of "substituted heterocyclic groups" include the group in example group G2A below where the hydrogen atoms of the "unsubstituted heterocyclic group" have been substituted, and the example of a substituted heterocyclic group in example group G2B below. It should be noted that the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are only examples. The "substituted heterocyclic groups" described in this specification also include the group in example group G2B where the hydrogen atoms bonded to the cyclic atoms of the heterocyclic group itself have been further substituted with a substituent, and the group in example group G2B where the hydrogen atoms of the substituent have been further substituted with a substituent.

[0353] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1), unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2), unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0354] Specific example group G2B includes, for example, the following: a nitrogen-containing substituted heterocyclic group (specific example group G2B1), an oxygen-containing substituted heterocyclic group (specific example group G2B2), a sulfur-containing substituted heterocyclic group (specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) have been substituted with a substituent (specific example group G2B4).

[0355] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1):

[0356] pyrrole,

[0357] Imidazole group,

[0358] pyrazolyl,

[0359] Triazole group,

[0360] Tetrazolyl,

[0361] Oxazolyl,

[0362] Isoxazolyl,

[0363] Oxadiazole group,

[0364] Thiazole group,

[0365] Isothiazolyl,

[0366] Thiadiazole group,

[0367] pyridyl,

[0368] pyridazinyl,

[0369] Pyrimidine group,

[0370] Pyrazinyl,

[0371] Triazine group

[0372] Indole,

[0373] Isoindolyl,

[0374] Indazine-based

[0375] Quinazine-based

[0376] Quinoline,

[0377] Isoquinoline,

[0378] Crenoline group

[0379] Phthaloazine

[0380] Quinazolinyl,

[0381] Quinoxaloyl,

[0382] Benzimidazole group,

[0383] Indazole group,

[0384] phenanthroline,

[0385] phenanthridine,

[0386] acridine group,

[0387] Phenazine group,

[0388] Carbazolyl,

[0389] Benzocarbazolyl,

[0390] Morpholinyl,

[0391] phenoxazine group,

[0392] phenothiazine group,

[0393] Azacarbazolyl, and

[0394] Diazacarbazolyl.

[0395] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2):

[0396] furanyl,

[0397] Oxazolyl,

[0398] Isoxazolyl,

[0399] Oxadiazole group,

[0400] Xuton base,

[0401] Benzofuranyl,

[0402] Isobenzofuranyl,

[0403] Dibenzofuranyl,

[0404] Naphthobenzofuranyl,

[0405] Benzoxazolyl,

[0406] Benzisoxazole group,

[0407] phenoxazine group,

[0408] Morpholinyl,

[0409] Dinaphthylfuranyl,

[0410] Azadibenzofuranyl,

[0411] diazadibenzofuranyl,

[0412] Azanaphthalenebenzofuranyl and

[0413] Diazanaphthenebenzofuranyl.

[0414] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3):

[0415] Thiophene group

[0416] Thiazole group,

[0417] Isothiazolyl,

[0418] Thiadiazole group,

[0419] benzothienyl

[0420] isobenzothienyl

[0421] dibenzothienyl

[0422] Naphthobenzothienyl

[0423] Benzothiazolyl,

[0424] Benzisothiazolyl,

[0425] phenothiazine group,

[0426] dinaphthothienyl

[0427] azadibenzothienyl

[0428] diazadibenzothienyl

[0429] azanaphthobenzothienyl and

[0430] diazanaphthobenzothienyl.

[0431] • A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0432] [Chemical Formula 7]

[0433]

[0434] [Chemical Formula 8]

[0435]

[0436] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each can be independently composed of an oxygen atom, a sulfur atom, NH, or CH2. Among them, X... A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH.

[0437] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A When at least one of them is NH or CH2, the monovalent heterocyclic group derived from the ring structure shown in the above general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0438] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1):

[0439] (9-phenyl)carbazole group,

[0440] (9-Biphenyl)carbazolyl,

[0441] (9-Phenyl)phenylcarbazolyl,

[0442] (9-Naphthyl)carbazole,

[0443] Diphenylcarbazole-9-yl,

[0444] Phenylexacarbazole-9-yl,

[0445] Methylbenzimidazole,

[0446] Ethylbenzimidazole,

[0447] Phenylacetyl,

[0448] Biphenyltriazine

[0449] diphenyltriazine group,

[0450] phenylquinazolinyl, and

[0451] Biphenylquinazolinyl.

[0452] • Heterocyclic groups containing oxygen atoms (specific example group G2B2):

[0453] Phenyl dibenzofuranyl,

[0454] Methyldibenzofuranyl,

[0455] tert-butyldibenzofuranyl and

[0456] The monovalent residue of [9H-xanton-9,9'-[9H]fluorene].

[0457] • Heterocyclic groups containing sulfur atoms (specific example group G2B3):

[0458] Phenyl dibenzothiophene,

[0459] Methyldibenzothiophene,

[0460] tert-butyldibenzothiophene and

[0461] The monovalent residue of [9H-thiophene-9,9'-[9H]fluorene].

[0462] • Groups derived from the ring structures shown in the above general formulas (TEMP-16) to (TEMP-33) in which one or more hydrogen atoms of a monovalent heterocyclic group have been substituted with substituents (specific example group G2B4):

[0463] The aforementioned "one or more hydrogen atoms in a monovalent heterocyclic group" refers to hydrogen atoms bonded to the cyclic carbon atoms of the monovalent heterocyclic group, X A and Y A The hydrogen atom bonded to the nitrogen atom when at least one of them is NH and X A and Y A One of them is one or more hydrogen atoms in the methylene group when CH2 is present.

[0464] • "Substituted or unsubstituted alkyl groups"

[0465] As specific examples of "substituted or unsubstituted alkyl" described in this specification (specific example group G3), the following unsubstituted alkyl (specific example group G3A) and substituted alkyl (specific example group G3B) can be cited. (Here, unsubstituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when referred to as "alkyl", both "unsubstituted alkyl" and "substituted alkyl" are included.

[0466] "Substituted alkyl" refers to a group in which one or more hydrogen atoms of an "unsubstituted alkyl" have been substituted with a substituent. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms of an "unsubstituted alkyl" (specific example group G3A) have been substituted with a substituent, and examples of substituted alkyl (specific example group G3B). In this specification, "unsubstituted alkyl" refers to a chain-like alkyl group. Therefore, "unsubstituted alkyl" includes both straight-chain and branched-chain unsubstituted alkyl groups. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples; the "substituted alkyl" described in this specification also includes groups in which the hydrogen atoms of the alkyl group in specific example group G3B have been further substituted with a substituent, and groups in which the hydrogen atoms of the substituents in specific example group G3B have been further substituted with a substituent.

[0467] • Unsubstituted alkyl groups (specific example group G3A):

[0468] methyl,

[0469] Ethyl,

[0470] n-propyl,

[0471] Isopropyl,

[0472] n-Butyl,

[0473] Isobutyl,

[0474] sec-butyl and

[0475] tert-butyl.

[0476] • Substituted alkyl groups (specific example group G3B):

[0477] Heptafluoropropyl (including isomers),

[0478] Pentafluoroethyl,

[0479] 2,2,2-Trifluoroethyl and

[0480] Trifluoromethyl

[0481] • "Substituted or unsubstituted alkenyl groups"

[0482] Specific examples of "substituted or unsubstituted alkenyl groups" (specific example group G4) described in this specification include unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "substituted alkenyl group".) In this specification, when simply referred to as "alkenyl group", both "unsubstituted alkenyl group" and "substituted alkenyl group" are included.

[0483] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" group have been substituted with a substituent. Specific examples of "substituted alkenyl" include the "unsubstituted alkenyl" group (specific example group G4A) having a substituent and examples of substituted alkenyl groups (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples; the "substituted alkenyl" described in this specification also includes groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the alkenyl itself have been further substituted with a substituent, and groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the substituent have been further substituted with a substituent.

[0484] • Unsubstituted alkenyl groups (specific example group G4A):

[0485] vinyl,

[0486] Allyl

[0487] 1-Butenyl,

[0488] 2-Butenyl and

[0489] 3-Butenyl.

[0490] • Substituted alkenyl groups (specific example group G4B):

[0491] 1,3-Butadienyl,

[0492] 1-Methylvinyl

[0493] 1-Methylallyl,

[0494] 1,1-Dimethylallyl,

[0495] 2-Methylallyl and

[0496] 1,2-Dimethylallyl.

[0497] As specific examples of "substituted or unsubstituted alkynyl groups" described in this specification (specific example group G5), the following unsubstituted alkynyl groups (specific example group G5A) can be cited. (Here, unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group".) The following description of "alkynyl group" includes both "unsubstituted alkynyl group" and "substituted alkynyl group".

[0498] "Substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" have been replaced by a substituent. Specific examples of "substituted alkynyl group" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl group" (specific example group G5A) have been replaced by a substituent.

[0499] • Unsubstituted alkynyl group (specific example group G5A):

[0500] Acetylene group.

[0501] • "Substituted or unsubstituted cycloalkyl groups"

[0502] Specific examples of "substituted or unsubstituted cycloalkyl" described in this specification (specific example group G6) include unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B), etc. (Here, unsubstituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl".) In this specification, when referred to only as "cycloalkyl", both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.

[0503] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group have been substituted with a substituent. Specific examples of "substituted cycloalkyl" include the group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group (specific example group G6A) have been substituted with a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples. The "substituted cycloalkyl" described in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl" group of specific example group G6B have been substituted with a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted cycloalkyl" group of specific example group G6B have been further substituted with a substituent.

[0504] • Unsubstituted cycloalkyl groups (specific example group G6A):

[0505] Cyclopropyl,

[0506] Cyclobutyl,

[0507] Cyclopentyl,

[0508] Cyclohexyl,

[0509] 1-Adamantyl,

[0510] 2-Adamantyl,

[0511] 1-norborneol and

[0512] 2-norborneol.

[0513] • Substituted cycloalkyl groups (specific example group G6B):

[0514] 4-Methylcyclohexyl.

[0515] ·"-Si(R 901 (R) 902 (R) 903 The group shown in the figure”

[0516] As described in this specification, -Si(R) 901 (R) 902 (R) 903 Specific examples of the group shown in the figure (specific example group G7) can be given as follows:

[0517] -Si(G1)(G1)(G1),

[0518] -Si(G1)(G2)(G2)

[0519] -Si(G1)(G1)(G2),

[0520] -Si(G2)(G2)(G2),

[0521] -Si(G3)(G3)(G3) and

[0522] -Si(G6)(G6)(G6). Here.

[0523] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0524] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0525] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0526] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0527] In -Si(G1)(G1)(G1), multiple G1s may be identical or different from each other.

[0528] In -Si(G1)(G2)(G2), multiple G2s may be the same or different from each other.

[0529] In -Si(G1)(G1)(G2), multiple G1s may be the same or different from each other.

[0530] In -Si(G2)(G2)(G2), multiple G2s may be the same or different from each other.

[0531] In -Si(G3)(G3)(G3), multiple G3s may be identical or different from each other.

[0532] In -Si(G6)(G6)(G6), multiple G6s may be identical or different from each other.

[0533] ·“-O-(R 904 The group shown in the figure”

[0534] As described in this specification, -O-(R) 904 Specific examples of the group shown in the figure (specific example group G8) can be given as follows:

[0535] -O(G1)

[0536] -O(G2),

[0537] -O(G3) and

[0538] -O(G6).

[0539] Here,

[0540] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0541] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0542] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0543] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0544] ·“-S-(R 905 The group shown in the figure”

[0545] As described in this specification, -S-(R) 905 Specific examples of the group shown in the figure (specific example group G9) can be given as follows:

[0546] -S(G1)

[0547] -S(G2),

[0548] -S(G3) and

[0549] -S(G6).

[0550] Here,

[0551] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0552] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0553] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0554] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0555] ·"-N(R 906 (R) 907 The group shown in the figure”

[0556] As described in this specification, -N(R) 906 (R) 907 Specific examples of the group shown (specific example group G10) can be given as follows:

[0557] -N(G1)(G1),

[0558] -N(G2)(G2),

[0559] -N(G1)(G2),

[0560] -N(G3)(G3) and

[0561] -N(G6)(G6).

[0562] Here,

[0563] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0564] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0565] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0566] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0567] In -N(G1)(G1), multiple G1s may be the same or different from each other.

[0568] In -N(G2)(G2), multiple G2s may be the same or different from each other.

[0569] In -N(G3)(G3), multiple G3s may be the same or different from each other.

[0570] In -N(G6)(G6), multiple G6s may be the same or different from each other.

[0571] • "Halogen atom"

[0572] Specific examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0573] • "Substituted or unsubstituted fluoroalkyl groups"

[0574] The term "substituted or unsubstituted fluoroalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group has been replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group have been replaced by fluorine atoms (perfluorinated groups). Unless otherwise specified in this specification, the number of carbon atoms in an "unsubstituted fluoroalkyl" group is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted fluoroalkyl" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl" group have been replaced by a substituent. It should be noted that the term "substituted fluoroalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in a "substituted fluoroalkyl" group have been further replaced by a substituent, and groups in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl" group have been further replaced by a substituent. As a specific example of "unsubstituted fluoroalkyl", examples can be given of groups in which one or more hydrogen atoms in the above-mentioned "alkyl" (specific example group G3) have been replaced by fluorine atoms.

[0575] • "Substituted or unsubstituted haloalkyl groups"

[0576] The term "substituted or unsubstituted haloalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group has been replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group have been replaced by halogen atoms. Unless otherwise specified in this specification, the number of carbon atoms in an "unsubstituted haloalkyl" group is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted haloalkyl" refers to a group in which one or more hydrogen atoms of a "haloalkyl" group have been replaced by a substituent. It should be noted that "substituted haloalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in a "substituted haloalkyl" group have been further replaced by a substituent, and groups in which one or more hydrogen atoms of a substituent in a "substituted haloalkyl" group have been further replaced by a substituent. As a specific example of "unsubstituted haloalkyl", examples can be given of groups in which one or more hydrogen atoms of the above-mentioned "alkyl" (specific example group G3) have been substituted with halogen atoms. Haloalkyl is sometimes called haloalkyl.

[0577] • "Substituted or unsubstituted alkoxy groups"

[0578] As a specific example of "substituted or unsubstituted alkoxy group" as described in this specification, it is the group indicated by -O (G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0579] • "Substituted or unsubstituted alkylthio groups"

[0580] As a specific example of "substituted or unsubstituted alkylthio group" as described in this specification, it is the group indicated by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0581] • "Substituted or unsubstituted aryloxy groups"

[0582] As a specific example of "substituted or unsubstituted aryloxy group" as described in this specification, it is the group indicated by -O (G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of carbon atoms in the ring of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0583] • "Substituted or unsubstituted arylthio groups"

[0584] As a specific example of "substituted or unsubstituted arylthio group" as described in this specification, it is the group indicated by -S(G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of carbon atoms in the ring of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0585] • "Substituted or unsubstituted trialkylsilyl groups"

[0586] As a specific example of "trialkylsilyl" as described in this specification, it is the group represented by -Si(G3)(G3)(G3), where G3 refers to the "substituted or unsubstituted alkyl" described in the specific example group G3. The plurality of G3s in -Si(G3)(G3)(G3) may be identical or different from each other. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the "trialkylsilyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0587] • "Substituted or unsubstituted aralkyl groups"

[0588] As a specific example of "substituted or unsubstituted aralkyl" as described in this specification, it is the group shown as -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl" described in specific example group G3, and G1 is the "substituted or unsubstituted aryl" described in specific example group G1. Therefore, "aralkyl" is a group in which the hydrogen atom of "alkyl" is replaced by "aryl" as a substituent, and is one embodiment of "substituted alkyl". "Unsubstituted aralkyl" is an "unsubstituted alkyl" that is substituted with "unsubstituted aryl", and the number of carbon atoms of "unsubstituted aralkyl" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.

[0589] Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl.

[0590] Unless otherwise specified in this specification, the substituted or unsubstituted aryl groups described herein are preferably phenyl, p-biphenyl, meta-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, meta-terphenyl-4-yl, meta-terphenyl-3-yl, meta-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthraceneyl, phenanthryl, pyrene, phenyl, triphenylene, fluorene, 9,9'-spirobisfluorene, 9,9-dimethylfluorene, and 9,9-diphenylfluorene, etc.

[0591] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic groups described herein are preferably pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, phenanthrolinel, carbazole (1-carbazole, 2-carbazole, 3-carbazole, 4-carbazole or 9-carbazole), benzocarbazole, azacarbazole, diazacarbazole, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophene, and naphtho-benzofuranyl. Benzothiophene, azadibenzothiophene, diazadibenzothiophene, (9-phenyl)carbazoyl ((9-phenyl)carbazo-1-yl, (9-phenyl)carbazo-2-yl, (9-phenyl)carbazo-3-yl or (9-phenyl)carbazo-4-yl), (9-biphenyl)carbazoyl, (9-phenyl)phenylcarbazoyl, diphenylcarbazo-9-yl, phenylcarbazo-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl and phenyldibenzothiophene, etc.

[0592] In this specification, the carbazoyl group, unless otherwise specified herein, specifically refers to any one of the following groups.

[0593] [Chemical Formula 9]

[0594]

[0595] In this specification, (9-phenyl)carbazolyl refers specifically to any one of the following groups unless otherwise stated herein.

[0596]

Chemical Formula 10

[0597]

[0598] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.

[0599] In this specification, dibenzofuranyl and dibenzothiopheneyl are specifically any one of the following groups unless otherwise stated in this specification.

[0600]

Chemical Formula 11

[0601]

[0602] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.

[0603] Unless otherwise specified in this specification, the substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and tert-butyl.

[0604] • "Substituted or unsubstituted aryl groups"

[0605] Unless otherwise stated, the "substituted or unsubstituted aryl group" described in this specification is a divalent group derived from the "substituted or unsubstituted aryl group" by removing one hydrogen atom from the aryl ring. Specific examples of "substituted or unsubstituted aryl group" (specific example group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in specific example group G1 by removing one hydrogen atom from the aryl ring.

[0606] • "Substituted or unsubstituted divalent heterocyclic groups"

[0607] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived from the aforementioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom from the heterocycle. Specific examples of "substituted or unsubstituted divalent heterocyclic groups" (specific example group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in specific example group G2 by removing one hydrogen atom from the heterocycle.

[0608] • "Substituted or unsubstituted alkylene compounds"

[0609] Unless otherwise stated, "substituted or unsubstituted alkylene groups" as described in this specification are divalent groups derived from "substituted or unsubstituted alkylene groups" by removing one hydrogen atom from the alkyl chain. Specific examples of "substituted or unsubstituted alkylene groups" (specific example group G14) include divalent groups derived from "substituted or unsubstituted alkylene groups" described in specific example group G3 by removing one hydrogen atom from the alkyl chain.

[0610] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described herein is preferably any one of the groups in the following general formulas (TEMP-42) to (TEMP-68).

[0611]

Chemical Formula 12

[0612]

[0613]

Chemical Formula 13

[0614]

[0615] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0616] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.

[0617]

Chemical Formula 14

[0618]

[0619] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0620] Formulas Q9 and Q 10 They can form rings by bonding with each other via single bonds.

[0621] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.

[0622]

Chemical Formula 15

[0623]

[0624] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0625] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.

[0626] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described herein is preferably any group of the following general formulas (TEMP-69) to (TEMP-102).

[0627] [Chemical Formula 16]

[0628]

[0629]

Chemical Formula 17

[0630]

[0631] [Chemical Formula 18]

[0632]

[0633] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0634] [Chemical Formula 19]

[0635]

[0636]

Chemical Formula 20

[0637]

[0638]

Chemical Formula 21

[0639]

[0640]

Chemical Formula 22

[0641]

[0642] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0643] The above is an explanation of "substituents described in this specification".

[0644] • "Cases where bonds form rings"

[0645] In this specification, the description of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring, or bonded together to form a substituted or unsubstituted fused ring, or not bonded together" refers to the cases of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring", "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted fused ring", and "one or more groups of two or more adjacent elements not bonded together".

[0646] The following description addresses the cases described in this specification as "forming a substituted or unsubstituted monocyclic ring by bonding one or more groups of two or more adjacent elements together" and "forming a substituted or unsubstituted fused ring by bonding one or more groups of two or more adjacent elements together" (hereinafter, these cases are sometimes collectively referred to as "forming a ring by bonding"). The case of anthracene compounds represented by the following general formula (TEMP-103) with an anthracene ring as the parent skeleton will be used as an example.

[0647]

Chemical Formula 23

[0648]

[0649] For example, in the case of R 921 ~R 930 In the case of "one or more groups consisting of two or more adjacent elements bonded together to form a loop", a group consisting of two adjacent elements is referred to as R. 921 With R 922 group, R 922 With R 923 group, R 923 With R 924 group, R 924 With R 930 group, R 930 With R 925 group, R 925 With R 926 group, R 926 With R 927 group, R 927 With R 928 group, R 928 With R 929 The group, and R 929 With R 921 The group.

[0650] The phrase "one or more groups" refers to the fact that two or more of the aforementioned groups consisting of two or more adjacent elements can simultaneously form a loop. For example, in R... 921 With R 922 They bond together to form a ring Q A Moreover, R 925 With R 926 They bond together to form a ring Q B In this case, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0651]

Chemical Formula 24

[0652]

[0653] The formation of rings from "groups consisting of two or more adjacent elements" includes not only the case of bonds formed by groups consisting of "two" adjacent elements, as in the previous example, but also the case of bonds formed by groups consisting of "three or more" adjacent elements. For example, it refers to R... 921 With R 922 They bond together to form a ring Q A And R 922 With R 923 They bond together to form a ring Q C , consisting of 3 adjacent (R) 921 R 922 and R 923When the groups of components Q bond together to form a ring and fuse to the anthracene matrix, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q... A and ring Q C There are a total of R 922 .

[0654] [Chemical Formula 25]

[0655]

[0656] In the formed "single ring" or "fused ring," the structure of the ring alone can be either a saturated ring or an unsaturated ring. Even when a "single ring" or "fused ring" is formed from "one group of two adjacent rings," the "single ring" or "fused ring" can still form a saturated ring or an unsaturated ring. For example, the ring Q formed in the above general formula (TEMP-104) A and ring Q B Each is either a "single ring" or a "fused ring". Additionally, the ring Q formed in the above general formula (TEMP-105) A and Q ring C It is a "fused ring". The ring Q of the above general formula (TEMP-105) A With ring Q C Through ring Q A With ring Q C Fusing together forms a fused ring. The ring Q of the above general formula (TMEP-104) A If it is a benzene ring, then ring Q A It is a single ring. The ring Q in the above general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a fused ring.

[0657] "Unsaturated rings" refer to aromatic hydrocarbon rings or aromatic heterocycles. "Saturated rings" refer to aliphatic hydrocarbon rings or non-aromatic heterocycles.

[0658] As a specific example of an aromatic hydrocarbon ring, the structure formed by the hydrogen atom-terminated group in specific example group G1 can be cited.

[0659] As a specific example of an aromatic heterocycle, one can cite the structure formed by end-capping an aromatic heterocycle group with hydrogen atoms in specific example group G2.

[0660] As a specific example of an aliphatic hydrocarbon ring, the structure formed by the hydrogen atom-terminated group in specific example group G6 can be cited.

[0661] "Ring formation" refers to the formation of a ring solely by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton forming a ring with one or more other optional elements. For example, R shown in the above general formula (TEMP-104) 921 With R 922 The ring Q formed by mutual bonding A It refers to R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 The carbon atoms of the bonded anthracene framework form rings with one or more optional elements. As a specific example, in the case of R... 921 With R 922 Forming ring Q A In the case of R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 When the bonded anthracene skeleton carbon atoms and 4 carbon atoms form a monocyclic unsaturated ring, R 921 With R 922 The resulting ring is a benzene ring.

[0662] Here, "optional element" is preferably selected from at least one element chosen from the group consisting of carbon, nitrogen, oxygen, and sulfur, unless otherwise specified in this specification. In the case of optional elements (e.g., carbon or nitrogen), non-ring bonds can be capped by hydrogen atoms or replaced by "optional substituents" described later. When optional elements other than carbon are included, the resulting ring is a heterocycle.

[0663] Unless otherwise specified in this specification, the "one or more optional elements" constituting a monocyclic or fused ring are preferably two or more and 15 or less, more preferably three or more and 12 or less, and even more preferably three or more and 5 or less.

[0664] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".

[0665] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".

[0666] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.

[0667] Unless otherwise stated in this specification, the "unsaturated ring" is preferably a benzene ring.

[0668] In the case of “one or more groups consisting of two or more adjacent elements”, “forming a substituted or unsubstituted monocyclic ring by mutual bonding”, or “forming a substituted or unsubstituted fused ring by mutual bonding”, unless otherwise stated in this specification, it is preferred that one or more groups consisting of two or more adjacent elements are mutually bonded to form a substituted or unsubstituted “unsaturated ring” consisting of a plurality of atoms of a parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0669] When the aforementioned "monocyclic" or "fused-ring" rings have substituents, the substituents are, for example, the "optional substituents" described later. Specific examples of substituents when the aforementioned "monocyclic" or "fused-ring" rings have substituents are the substituents described in the section "Substituents Represented in This Specification" above.

[0670] When the aforementioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of substituents when the aforementioned "monocyclic" or "fused ring" has a substituent are the substituents described in the section "Substituents Represented in This Specification" above.

[0671] The above explains the cases of "a single ring formed by bonding one or more groups of two or more adjacent elements together" and "a fused ring formed by bonding one or more groups of two or more adjacent elements together" ("the case of forming a ring by bonding").

[0672] Substituents when described as "substituted or unsubstituted"

[0673] In one embodiment of this specification, the substituents described above as "substituted or unsubstituted" (sometimes referred to as "optional substituents" in this specification) are, for example, selected from...

[0674] Unsubstituted alkyl groups having 1 to 50 carbon atoms

[0675] Unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0676] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms

[0677] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0678] -Si(R 901 (R) 902 (R) 903 ),

[0679] -O-(R 904 ),

[0680] -S-(R 905 ),

[0681] -N(R 906 (R) 907 ),

[0682] Halogen atom, cyano group, nitro group,

[0683] Unsubstituted aryl groups with 6 to 50 carbon atoms and

[0684] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms

[0685] Groups, etc., in the composition group

[0686] Here, R 901 ~R 907 Each independently

[0687] hydrogen atom,

[0688] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0689] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0690] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0691] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0692] In R 901 When there are more than two, more than two R 901 They are the same or different.

[0693] In R 902 When there are more than two, more than two R 902 They are the same or different.

[0694] In R 903 When there are more than two, more than two R 903 They are the same or different.

[0695] In R 904 When there are more than two, more than two R 904 They are the same or different.

[0696] In R 905 When there are more than two, more than two R 905 They are the same or different.

[0697] In R 906 When there are more than two, more than two R 906 They are the same or different.

[0698] In R 907 When there are more than two, more than two R 907 They are the same or different.

[0699] In one embodiment, the substituents described above as "substituted or unsubstituted" are selected freely.

[0700] Alkyl groups with 1 to 50 carbon atoms

[0701] Aryl groups with 6 to 50 carbon atoms and

[0702] Groups in the group consisting of heterocyclic groups with 5 to 50 cyclic atoms.

[0703] In one embodiment, the substituents described above as "substituted or unsubstituted" are selected freely.

[0704] Alkyl groups having 1 to 18 carbon atoms

[0705] aryl groups with 6 to 18 carbon atoms and

[0706] Groups in the group consisting of heterocyclic groups with 5 to 18 cyclic atoms.

[0707] Specific examples of each of the optional substituents are those described in the section "Substituents as described in this specification" above.

[0708] Unless otherwise stated in this specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring" with each other, preferably forming a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably forming a benzene ring.

[0709] Unless otherwise stated in this specification, optional substituents may also have other substituents. Any further substituents that may be present as optional substituents are the same as those described above.

[0710] In this specification, the numerical range represented by "AA~BB" refers to the range included by taking the value AA, which is written before "AA~BB", as the lower limit and the value BB, which is written after "AA~BB", as the upper limit.

[0711] [First Implementation Method]

[0712] (compound)

[0713] The compounds involved in this embodiment are those represented by the following general formula (1C-A).

[0714]

Chemical Formula 26

[0715]

[0716] (In the above general formula (1C-A),

[0717] R4~R8 and R 10 ~R 12 One of them is a group represented by the general formula (1D-A) above.

[0718] R1 to R3, R9, and R4 to R8 and R9 other than the groups shown in the above general formula (1D-A). 10 ~R 12 Each independently

[0719] hydrogen atom,

[0720] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0721] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0722] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0723] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0724] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0725] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0726] -O-(R 904 The groups shown in the figure,

[0727] -S-(R 905 The groups shown in the figure,

[0728] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0729] -C(=O)R 801 The groups shown

[0730] -COOR 802 The groups shown

[0731] Halogen atoms,

[0732] cyano,

[0733] Nitro,

[0734] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0735] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0736] In R 11 In the case of a group represented by the above general formula (1D-A), R 12 A phenyl group consisting of a hydrogen atom or with or without substitution.

[0737] In R 12 In the case of a group represented by the above general formula (1D-A), R 11 A phenyl group consisting of a hydrogen atom or with or without substitution.

[0738] In the above general formula (1D-A), R 21 ~R 30 One of them represents the bonding position with the benzo[a]anthracene ring in the above general formula (1C-A), and the R in the above general formula (1D-A) is not at that bonding position. 21 ~R 30 One or more groups consisting of two or more adjacent elements.

[0739] They bond together to form substituted or unsubstituted monocyclic rings.

[0740] They bond together to form substituted or unsubstituted fused rings, or

[0741] They do not bond with each other.

[0742] The R in the above general formula (1D-A) is not at the bonding position of the benzo[a]anthracene ring in the above general formula (1C-A), does not form the above-mentioned substituted or unsubstituted monocyclic ring, and does not form the above-mentioned substituted or unsubstituted fused ring. 21 ~R 30 Each independently

[0743] hydrogen atom,

[0744] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0745] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0746] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0747] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0748] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0749] -O-(R 904 The groups shown in the figure,

[0750] -S-(R905 The groups shown in the figure,

[0751] -N(R 906 (R) 907 The groups shown in the figure,

[0752] Halogen atoms,

[0753] cyano,

[0754] Nitro,

[0755] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0756] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0757] Among them, R 21 ~R 30 At least one of them is a group other than a hydrogen atom.

[0758] In the compounds represented by the above general formula (1C-A), R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently

[0759] hydrogen atom,

[0760] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0761] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0762] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0763] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0764] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.

[0765] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.

[0766] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.

[0767] In R904 In the case of multiple Rs, multiple Rs 904 They are the same or different.

[0768] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.

[0769] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.

[0770] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.

[0771] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[0772] In R 802 In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)

[0773] In the compounds involved in this embodiment, it is also preferred that the R in the general formula (1D-A) is not a bonded position to the benzo[a]anthracene ring in the general formula (1C-A), does not form the aforementioned substituted or unsubstituted monocyclic ring, does not form the aforementioned substituted or unsubstituted fused ring, and is not a hydrogen atom. 21 ~R 30 At least one of them is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.

[0774] In the compounds involved in this embodiment, it is also preferred that the R in the general formula (1D-A) is not a bonded position to the benzo[a]anthracene ring in the general formula (1C-A), does not form the aforementioned substituted or unsubstituted monocyclic ring, does not form the aforementioned substituted or unsubstituted fused ring, and is not a hydrogen atom. 21 ~R 30 At least one of them is a substituted or unsubstituted phenyl group.

[0775] In the compounds involved in this embodiment, it is also preferred that the group represented by the above general formula (1D-A) is the group represented by the following general formula (1D-A1), general formula (1D-A2) or general formula (1D-A3).

[0776] [Chemical Formula 27]

[0777]

[0778] (In the above general formula (1D-A1),

[0779] By R 21 ~R 29 One or more groups consisting of two or more adjacent elements.

[0780] They bond together to form substituted or unsubstituted monocyclic rings.

[0781] They bond together to form substituted or unsubstituted fused rings, or

[0782] They do not bond with each other.

[0783] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 21 ~R 29 Each independently

[0784] hydrogen atom,

[0785] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0786] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0787] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0788] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0789] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0790] -O-(R 904 The groups shown in the figure,

[0791] -S-(R 905 The groups shown in the figure,

[0792] -N(R 906 (R) 907 The groups shown in the figure,

[0793] Halogen atoms,

[0794] cyano,

[0795] Nitro,

[0796] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0797] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0798] Among them, R 21 ~R 29At least one of them is a group other than a hydrogen atom.

[0799] * indicates the bonding position with the benzo[a]anthracene ring in the above general formula (1C-A).

[0800] In the above general formula (1D-A2),

[0801] By R 21 ~R 28 and R 30 One or more groups consisting of two or more adjacent elements.

[0802] They bond together to form substituted or unsubstituted monocyclic rings.

[0803] They bond together to form substituted or unsubstituted fused rings, or

[0804] They do not bond with each other.

[0805] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 21 ~R 28 and R 30 Each independently relates to R in the above general formula (1D-A1). 21 ~R 29 Same meaning

[0806] Among them, R 21 ~R 28 and R 30 At least one of them is a group other than a hydrogen atom.

[0807] * indicates the bonding position with the benzo[a]anthracene ring in the above general formula (1C-A).

[0808] In the above general formula (1D-A3),

[0809] By R 21 ~R 27 R 29 and R 30 One or more groups consisting of two or more adjacent elements.

[0810] They bond together to form substituted or unsubstituted monocyclic rings.

[0811] They bond together to form substituted or unsubstituted fused rings, or

[0812] They do not bond with each other.

[0813] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 21 ~R 27 R 29 and R 30Each independently relates to R in the above general formula (1D-A1). 21 ~R 29 Same meaning

[0814] Among them, R 21 ~R 27 R 29 and R 30 At least one of them is a group other than a hydrogen atom.

[0815] * indicates the bonding position with the benzo[a]anthracene ring in the above general formula (1C-A).

[0816] In the compounds involved in this embodiment, it is also preferred that the group represented by the above general formula (1D-A1), general formula (1D-A2), or general formula (1D-A3) does not form the aforementioned substituted or unsubstituted monocyclic ring, does not form the aforementioned substituted or unsubstituted fused ring, and is not a hydrogen atom, and that the R in the above general formula (1D-A1) is... 21 ~R 29 At least one of them, R in the above general formula (1D-A2) 21 ~R 28 and R 30 At least one of them, or R in the above general formula (1D-A3) 21 ~R 27 R 29 and R 30 At least one of them is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.

[0817] In the compounds involved in this embodiment, it is also preferred that the group represented by the above general formula (1D-A1), general formula (1D-A2), or general formula (1D-A3) does not form the aforementioned substituted or unsubstituted monocyclic ring, does not form the aforementioned substituted or unsubstituted fused ring, and is not a hydrogen atom, and that the R in the above general formula (1D-A1) is... 21 ~R 29 At least one of them, R in the above general formula (1D-A2) 21 ~R 28 and R 30 At least one of them, or R in the above general formula (1D-A3) 21 ~R 27 R 29 and R 30 At least one of them is a substituted or unsubstituted phenyl group.

[0818] In the compounds involved in this embodiment, it is also preferred that the group represented by the above general formula (1D-A) is the group represented by the above general formula (1D-A1).

[0819] Among the compounds involved in this embodiment, R5, R6, R7, R8, and R are also preferred. 11 and R 12 One of them is a group represented by the general formula (1D-A) above.

[0820] Among the compounds involved in this embodiment, R6, R7, and R are also preferred. 11 and R 12 One of them is a group represented by the general formula (1D-A) above.

[0821] Among the compounds involved in this embodiment, R is also preferred. 11 The group is represented by the general formula (1D-A) above.

[0822] Among the compounds involved in this embodiment, R is preferred. 12 Compounds of the groups represented by the above general formula (1D-A).

[0823] Among the compounds involved in this embodiment, R is also preferred. 11 The groups represented by the above general formula (1D-A), R 12 It is an unsubstituted phenyl, or R 12 The groups represented by the above general formula (1D-A), R 11 It is an unsubstituted phenyl group.

[0824] Among the compounds involved in this embodiment, R is also preferred. 11 The groups represented by the above general formula (1D-A), R 12 It is an unsubstituted phenyl group.

[0825] Among the compounds involved in this embodiment, R is also preferred. 12 The groups represented by the above general formula (1D-A), R 11 It is an unsubstituted phenyl group.

[0826] The compounds involved in this embodiment are preferably those represented by the following general formula (1C-A-1).

[0827] The compounds involved in this embodiment are preferably those represented by the following general formula (1C-A-2).

[0828] [Chemical Formula 28]

[0829]

[0830] [Chemical Formula 29]

[0831]

[0832] (R1~R in the above general formula (1C-A-1)) 11 and R1 to R in the above general formula (1C-A-2) 10 and R 12 Each independently

[0833] hydrogen atom,

[0834] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0835] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0836] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0837] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0838] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0839] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0840] -O-(R 904 The groups shown in the figure,

[0841] -S-(R 905 The groups shown in the figure,

[0842] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0843] -C(=O)R 801 The groups shown

[0844] -COOR 802 The groups shown

[0845] Halogen atoms,

[0846] cyano,

[0847] Nitro,

[0848] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0849] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0850] R in the above general formulas (1C-A-1) and (1C-A-2) 21 ~R 28 and R 30 Each independently

[0851] hydrogen atom,

[0852] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0853] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0854] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0855] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0856] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0857] -O-(R 904 The groups shown in the figure,

[0858] -S-(R 905 The groups shown in the figure,

[0859] -N(R 906 (R) 907 The groups shown in the figure,

[0860] Halogen atoms,

[0861] cyano,

[0862] Nitro,

[0863] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0864] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0865] Among them, R 21 ~R 28 and R 30 At least one of them is a group other than a hydrogen atom.

[0866] Among the compounds involved in this embodiment, R is also preferred. 12 It is a hydrogen atom.

[0867] In the compounds involved in this embodiment, it is preferable that the molecule has one or more deuterium atoms.

[0868] In the compounds involved in this embodiment, it is also preferred that R1 to R3, R9 are hydrogen atoms, and R4 to R8 and R9 are hydrogen atoms other than the groups shown in the above general formula (1D-A). 10 ~R 12 And R when it is a hydrogen atom 21 ~R 30 One or more of them are deuterium atoms.

[0869] In the compounds involved in this embodiment, it is also preferred that R1 to R3, R9 are hydrogen atoms, and R4 to R8 and R9 are hydrogen atoms other than the groups shown in the above general formula (1D-A). 10 ~R 12 And R when it is a hydrogen atom 21 ~R 30 All are deuterium atoms.

[0870] In the compounds involved in this embodiment, R1 to R3, R9 when they are groups other than hydrogen atoms, and R4 to R8 and R9 when they are groups other than hydrogen atoms, excluding the groups shown in the above general formula (1D-A). 10 ~R 12 And R when it is a group other than a hydrogen atom 21 ~R 30 When each hydrogen atom is present, one or more of these hydrogen atoms are deuterium atoms.

[0871] In the compounds involved in this embodiment, R1 to R3, R9 when they are groups other than hydrogen atoms, and R4 to R8 and R9 when they are groups other than hydrogen atoms, excluding the groups shown in the above general formula (1D-A). 10 ~R 12 And R when it is a group other than a hydrogen atom 21 ~R 30 When each hydrogen atom is present, all hydrogen atoms are deuterium atoms.

[0872] In the compounds involved in this embodiment, if one of R5, R6, R7 and R8 is a group represented by the above general formula (1D-A), it is also preferred that R2 and R3 are hydrogen atoms.

[0873] Among the compounds involved in this embodiment, compounds that do not contain heteroatoms in their molecules are preferred.

[0874] In the compounds involved in this embodiment, it is also preferred that the groups described as "substituted or unsubstituted" are all "unsubstituted" groups, and the rings described as "substituted or unsubstituted" are all "unsubstituted" rings.

[0875] • Method for manufacturing the compound involved in this embodiment

[0876] The compounds involved in this embodiment can be manufactured according to the synthesis method described in the examples below. Alternatively, the compounds involved in this embodiment can also be manufactured by using known alternative reactions and starting materials corresponding to the target substance, following the same synthesis method.

[0877] Specific examples of compounds involved in this embodiment

[0878] As a specific example of the compounds involved in this embodiment, for example, the compounds that fall within the scope of the compounds involved in this embodiment are examples of the compounds shown in the compound of general formula (1C) used as the first compound in the organic electroluminescent element of the fourth embodiment described later.

[0879] [Second Implementation]

[0880] (compound)

[0881] The compounds involved in this embodiment are those represented by the following general formula (1C-B).

[0882]

Chemical Formula 30

[0883]

[0884] (In the above general formula (1C-B),

[0885] R4~R6, R8 and R 10 ~R 12 One of them is a group represented by the general formula (1D-B) above.

[0886] R1–R3, R7, R9, and R4–R6, R8, and R9, excluding the groups shown in the above general formula (1D-B). 10 ~R 12 Each independently

[0887] hydrogen atom,

[0888] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0889] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0890] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0891] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0892] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0893] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0894] -O-(R 904 The groups shown in the figure,

[0895] -S-(R 905 The groups shown in the figure,

[0896] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0897] -C(=O)R 801 The groups shown

[0898] -COOR 802 The groups shown

[0899] Halogen atoms,

[0900] cyano,

[0901] Nitro,

[0902] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0903] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0904] In R 11 In the case of a group represented by the above general formula (1D-B), R 12 It is a hydrogen atom or an unsubstituted phenyl group.

[0905] In R 12 In the case of a group represented by the above general formula (1D-B), R 11 For substituted or unsubstituted phenyl groups,

[0906] In the above general formula (1D-B), R 21 ~R 30 One of them represents the bonding position with the benzo[a]anthracene ring in the above general formula (1C-B), and the R in the above general formula (1D-B) is not at that bonding position. 21 ~R 30 One or more groups consisting of two or more adjacent elements.

[0907] They bond together to form substituted or unsubstituted monocyclic rings.

[0908] They bond together to form substituted or unsubstituted fused rings, or

[0909] They do not bond with each other.

[0910] The R in the above general formula (1D-B) is not at the bonding position with the benzo[a]anthracene ring in the above general formula (1C-B), does not form the above-mentioned substituted or unsubstituted monocyclic ring, and does not form the above-mentioned substituted or unsubstituted fused ring. 21 ~R 30 Each independently

[0911] hydrogen atom,

[0912] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0913] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0914] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0915] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0916] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0917] -O-(R 904 The groups shown in the figure,

[0918] -S-(R 905 The groups shown in the figure,

[0919] -N(R 906 (R) 907 The groups shown in the figure,

[0920] Halogen atoms,

[0921] cyano,

[0922] Nitro,

[0923] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0924] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0925] In the compounds represented by the above general formula (1C-B), R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently

[0926] hydrogen atom,

[0927] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0928] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0929] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0930] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0931] In R 901In the case of multiple Rs, multiple Rs 901 They are the same or different.

[0932] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.

[0933] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.

[0934] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.

[0935] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.

[0936] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.

[0937] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.

[0938] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[0939] In R 802 In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)

[0940] In the compounds involved in this embodiment, it is also preferred that the R in the general formula (1D-B) is not bonded to the benzo[a]anthracene ring in the general formula (1C-B), does not form the aforementioned substituted or unsubstituted monocyclic ring, and does not form the aforementioned substituted or unsubstituted fused ring. 21 ~R 30 At least one of them is a group other than a hydrogen atom.

[0941] In the compounds involved in this embodiment, it is also preferred that the R in the general formula (1D-B) is not bonded to the benzo[a]anthracene ring in the general formula (1C-B), does not form the aforementioned substituted or unsubstituted monocyclic ring, and does not form the aforementioned substituted or unsubstituted fused ring. 21 ~R 30 At least one of them is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.

[0942] In the compounds involved in this embodiment, it is also preferred that the R in the general formula (1D-B) is not bonded to the benzo[a]anthracene ring in the general formula (1C-B), does not form the aforementioned substituted or unsubstituted monocyclic ring, and does not form the aforementioned substituted or unsubstituted fused ring. 21 ~R 30 At least one of them is a substituted or unsubstituted phenyl group.

[0943] In the compounds involved in this embodiment, it is also preferred that the group represented by the above general formula (1D-B) is the group represented by the following general formula (1D-B1), general formula (1D-B2) or general formula (1D-B3).

[0944]

Chemical Formula 31

[0945]

[0946] (In the above general formula (1D-B1),

[0947] By R 21 ~R 29 One or more groups consisting of two or more adjacent elements.

[0948] They bond together to form substituted or unsubstituted monocyclic rings.

[0949] They bond together to form substituted or unsubstituted fused rings, or

[0950] They do not bond with each other.

[0951] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 21 ~R 29 Each independently

[0952] hydrogen atom,

[0953] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0954] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0955] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0956] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0957] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0958] -O-(R904 The groups shown in the figure,

[0959] -S-(R 905 The groups shown in the figure,

[0960] -N(R 906 (R) 907 The groups shown in the figure,

[0961] Halogen atoms,

[0962] cyano,

[0963] Nitro,

[0964] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0965] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0966] * indicates the bonding position with the benzo[a]anthracene ring in the above general formula (1C-B).

[0967] In the above general formula (1D-B2),

[0968] By R 21 ~R 28 and R 30 One or more groups consisting of two or more adjacent elements.

[0969] They bond together to form substituted or unsubstituted monocyclic rings.

[0970] They bond together to form substituted or unsubstituted fused rings, or

[0971] They do not bond with each other.

[0972] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 21 ~R 28 and R 30 Each independently relates to R in the above general formula (1D-B1). 21 ~R 29 Same meaning

[0973] * indicates the bonding position with the benzo[a]anthracene ring in the above general formula (1C-B).

[0974] In the above general formula (1D-B3),

[0975] By R 21 ~R 27 R 29 and R 30 One or more groups consisting of two or more adjacent elements.

[0976] They bond together to form substituted or unsubstituted monocyclic rings.

[0977] They bond together to form substituted or unsubstituted fused rings, or

[0978] They do not bond with each other.

[0979] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 21 ~R 27 R 29 and R 30 Each independently relates to R in the above general formula (1D-B1). 21 ~R 29 Same meaning

[0980] * indicates the bonding position with the benzo[a]anthracene ring in the above general formula (1C-B).

[0981] In the compounds involved in this embodiment, it is also preferred that the R in the above general formula (1D-B1) does not form the aforementioned substituted or unsubstituted monocyclic ring and does not form the aforementioned substituted or unsubstituted fused ring. 21 ~R 29 At least one of them, R in the above general formula (1D-B2) 21 ~R 28 and R 30 At least one of them, or R in the above general formula (1D-B3) 21 ~R 27 R 29 and R 30 At least one of them is a group other than a hydrogen atom.

[0982] In the compounds involved in this embodiment, it is also preferred that the R in the above general formula (1D-B1) does not form the aforementioned substituted or unsubstituted monocyclic ring and does not form the aforementioned substituted or unsubstituted fused ring. 21 ~R 29 At least one of them, R in the above general formula (1D-B2) 21 ~R 28 and R 30 At least one of them, or R in the above general formula (1D-B3) 21 ~R 27 R 29 and R 30 At least one of them is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.

[0983] In the compounds involved in this embodiment, it is also preferred that the R in the above general formula (1D-B1) does not form the aforementioned substituted or unsubstituted monocyclic ring and does not form the aforementioned substituted or unsubstituted fused ring. 21 ~R 29 At least one of them, R in the above general formula (1D-B2) 21 ~R 28 and R 30 At least one of them, or R in the above general formula (1D-B3) 21 ~R 27 R 29 and R 30 At least one of them is a substituted or unsubstituted phenyl group.

[0984] In the compounds involved in this embodiment, it is also preferred that the group represented by the above general formula (1D-B) is the group represented by the above general formula (1D-B1).

[0985] Among the compounds involved in this embodiment, R5, R6, R8, and R are also preferred. 11 and R 12 One of them is a group represented by the general formula (1D-B) above.

[0986] Among the compounds involved in this embodiment, R6 and R are also preferred. 11 and R 12 One of them is a group represented by the general formula (1D-B) above.

[0987] Among the compounds involved in this embodiment, R is also preferred. 11 The group is represented by the general formula (1D-B) above.

[0988] Among the compounds involved in this embodiment, R is also preferred. 12 The group is represented by the general formula (1D-B) above.

[0989] Among the compounds involved in this embodiment, R is also preferred. 11 The groups represented by the above general formula (1D-B), R 12 It is an unsubstituted phenyl, or R 12 The groups represented by the above general formula (1D-B), R 11 It is an unsubstituted phenyl group.

[0990] Among the compounds involved in this embodiment, R is also preferred. 11 For the group represented by the above general formula (1D-B), R 12 It is an unsubstituted phenyl group.

[0991] Among the compounds involved in this embodiment, R is also preferred. 12 For the group represented by the above general formula (1D-B), R 11 It is an unsubstituted phenyl group.

[0992] The compounds involved in this embodiment are preferably those represented by the following general formula (1C-B-1).

[0993] The compounds involved in this embodiment are preferably those represented by the following general formula (1C-B-2).

[0994]

Chemical Formula 32

[0995]

[0996]

Chemical Formula 33

[0997]

[0998] (R1~R in the above general formula (1C-B-1)) 10 and R1 to R in the above general formula (1C-B-2) 10 Each independently

[0999] hydrogen atom,

[1000] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1001] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[1002] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1003] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1004] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1005] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1006] -O-(R 904 The groups shown in the figure,

[1007] -S-(R 905 The groups shown in the figure,

[1008] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[1009] -C(=O)R 801 The groups shown

[1010] -COOR 802 The groups shown

[1011] Halogen atoms,

[1012] cyano,

[1013] Nitro,

[1014] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1015] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1016] R in the above general formulas (1C-B-1) and (1C-B-2) 21 ~R 28 and R 30 Each independently

[1017] hydrogen atom,

[1018] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1019] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1020] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1021] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1022] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1023] -O-(R 904 The groups shown in the figure,

[1024] -S-(R 905 The groups shown in the figure,

[1025] -N(R 906 (R) 907 The groups shown in the figure,

[1026] Halogen atoms,

[1027] cyano,

[1028] Nitro,

[1029] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1030] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1031] In the above general formula (1C-B-1), R 11For substituted or unsubstituted phenyl groups,

[1032] In the above general formula (1C-B-2), R 12 (This could be a hydrogen atom or an unsubstituted phenyl group.)

[1033] Among the compounds involved in this embodiment, R7 and R are also preferred. 12 It is a hydrogen atom.

[1034] In the compounds involved in this embodiment, it is also preferable that they have one or more deuterium atoms in the molecule.

[1035] In the compounds involved in this embodiment, it is also preferred that R1 to R3, R7, and R9 are hydrogen atoms, and that R4 to R6, R8, and R9 are hydrogen atoms other than the groups shown in the above general formula (1D-B). 10 ~R 12 And R when it is a hydrogen atom 21 ~R 30 One or more of them are deuterium atoms.

[1036] In the compounds involved in this embodiment, it is also preferred that R1 to R3, R7, and R9 are hydrogen atoms, and that R4 to R6, R8, and R9 are hydrogen atoms other than the groups shown in the above general formula (1D-B). 10 ~R 12 And R when it is a hydrogen atom 21 ~R 30 All are deuterium atoms.

[1037] In the compounds involved in this embodiment, it is also preferred that R1 to R3, R7, and R9 are groups other than hydrogen atoms, and that R4 to R8 and R9 are groups other than hydrogen atoms, excluding the groups shown in the above general formula (1D-B). 10 ~R 12 And R when it is a group other than a hydrogen atom 21 ~R 30 When each hydrogen atom is present, one or more of these hydrogen atoms are deuterium atoms.

[1038] In the compounds involved in this embodiment, it is also preferred that R1 to R3, R7, and R9 are groups other than hydrogen atoms, and that R4 to R8 and R9 are groups other than hydrogen atoms, excluding the groups shown in the above general formula (1D-B). 10 ~R 12 And R when it is a group other than a hydrogen atom 21 ~R 30 When each hydrogen atom is present, all hydrogen atoms are deuterium atoms.

[1039] Among the compounds involved in this embodiment, compounds that do not contain heteroatoms in their molecules are preferred.

[1040] In the compounds involved in this embodiment, it is also preferred that the groups described as "substituted or unsubstituted" are all "unsubstituted" groups, and the rings described as "substituted or unsubstituted" are all "unsubstituted" rings.

[1041] • Method for manufacturing the compound involved in this embodiment

[1042] The compounds involved in this embodiment can be manufactured according to the synthesis method described in the examples below. Alternatively, the compounds involved in this embodiment can also be manufactured by using known alternative reactions and starting materials corresponding to the target substance, following the same synthesis method.

[1043] Specific examples of compounds involved in this embodiment

[1044] As a specific example of the compounds involved in this embodiment, for example, the compounds that fall within the scope of the compounds involved in this embodiment are examples of the compounds shown in the compound of general formula (1C) used as the first compound in the organic electroluminescent element of the fourth embodiment described later.

[1045] [Third Implementation Method]

[1046] (compound)

[1047] The compounds involved in this embodiment are those represented by the following general formula (1C-C).

[1048] [Chemical Formula 34]

[1049]

[1050] (In the above general formula (1C-C),

[1051] R4~R8 and R 10 ~R 12 One of them is a group represented by the general formula (1D-C) above.

[1052] R1 to R3, R9, and R4 to R8 and R9 other than the groups shown in the above general formula (1D-C). 10 ~R 12 Each independently

[1053] hydrogen atom,

[1054] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1055] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[1056] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1057] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1058] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1059] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1060] -O-(R 904 The groups shown in the figure,

[1061] -S-(R 905 The groups shown in the figure,

[1062] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[1063] -C(=O)R 801 The groups shown

[1064] -COOR 802 The groups shown

[1065] Halogen atoms,

[1066] cyano,

[1067] Nitro,

[1068] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1069] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1070] In R 11 In the case of a group represented by the above general formula (1D-C), R 12 A phenyl group consisting of a hydrogen atom or with or without substitution.

[1071] In R 12 In the case of a group represented by the above general formula (1D-C), R 11 A phenyl group consisting of a hydrogen atom or with or without substitution.

[1072] In the above general formula (1D-C), R 22 R 23 R 25 R 27 R 28 and R 30 One of them represents the bonding position with the benzo[a]anthracene ring in the above general formula (1C-C), and is represented by R.21 R 24 R 26 and R 29 And R in the above general formula (1D-C) that is not at the bonding site. 22 R 23 R 25 R 27 R 28 and R 30 One or more groups consisting of two or more adjacent elements.

[1073] They bond together to form substituted or unsubstituted monocyclic rings.

[1074] They bond together to form substituted or unsubstituted fused rings, or

[1075] They do not bond with each other.

[1076] The R in the above general formula (1D-C) is not at the bonding position with the benzo[a]anthracene ring in the above general formula (1C-C), does not form the above-mentioned substituted or unsubstituted monocyclic ring, and does not form the above-mentioned substituted or unsubstituted fused ring. 21 ~R 30 Each independently

[1077] hydrogen atom,

[1078] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1079] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1080] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1081] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1082] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1083] -O-(R 904 The groups shown in the figure,

[1084] -S-(R 905 The groups shown in the figure,

[1085] -N(R 906 (R) 907 The groups shown in the figure,

[1086] Halogen atoms,

[1087] cyano,

[1088] Nitro,

[1089] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1090] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1091] In the compounds represented by the above general formula (1C-C), R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently

[1092] hydrogen atom,

[1093] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1094] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1095] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1096] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1097] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.

[1098] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.

[1099] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.

[1100] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.

[1101] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.

[1102] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.

[1103] In R 907 In the case of multiple Rs, multiple Rs 907They are the same or different.

[1104] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[1105] In R 802 In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)

[1106] In the compounds involved in this embodiment, it is also preferred that the R in the general formula (1D-C) is not bonded to the benzo[a]anthracene ring in the general formula (1C-C), does not form the aforementioned substituted or unsubstituted monocyclic ring, and does not form the aforementioned substituted or unsubstituted fused ring. 21 ~R 30 At least one of them is a group other than a hydrogen atom.

[1107] In the compounds involved in this embodiment, it is also preferred that the R in the general formula (1D-C) is not bonded to the benzo[a]anthracene ring in the general formula (1C-C), does not form the aforementioned substituted or unsubstituted monocyclic ring, and does not form the aforementioned substituted or unsubstituted fused ring. 21 ~R 30 At least one of them is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.

[1108] In the compounds involved in this embodiment, it is also preferred that the R in the general formula (1D-C) is not bonded to the benzo[a]anthracene ring in the general formula (1C-C), does not form the aforementioned substituted or unsubstituted monocyclic ring, and does not form the aforementioned substituted or unsubstituted fused ring. 21 ~R 30 At least one of them is a substituted or unsubstituted phenyl group as described above.

[1109] In the compounds involved in this embodiment, it is also preferred that the group represented by the above general formula (1D-C) is the group represented by the following general formula (1D-C1) or general formula (1D-C3).

[1110]

Chemical Formula 35

[1111]

[1112] (In the above general formula (1D-C1),

[1113] By R 21 ~R 29 One or more groups consisting of two or more adjacent elements.

[1114] They bond together to form substituted or unsubstituted monocyclic rings.

[1115] They bond together to form substituted or unsubstituted fused rings, or

[1116] They do not bond with each other.

[1117] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 21 ~R 29 Each independently

[1118] hydrogen atom,

[1119] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1120] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1121] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1122] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1123] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1124] -O-(R 904 The groups shown in the figure,

[1125] -S-(R 905 The groups shown in the figure,

[1126] -N(R 906 (R) 907 The groups shown in the figure,

[1127] Halogen atoms,

[1128] cyano,

[1129] Nitro,

[1130] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1131] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1132] * indicates the bonding position with the benzo[a]anthracene ring in the above general formula (1C-C).

[1133] In the above general formula (1D-C3),

[1134] By R 21 ~R 27 R 29and R 30 One or more groups consisting of two or more adjacent elements.

[1135] They bond together to form substituted or unsubstituted monocyclic rings.

[1136] They bond together to form substituted or unsubstituted fused rings, or

[1137] They do not bond with each other.

[1138] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 21 ~R 27 R 29 and R 30 Each independently relates to R in the above general formula (1D-C1). 21 ~R 29 Same meaning

[1139] * indicates the bonding position with the benzo[a]anthracene ring in the above general formula (1C-C).

[1140] In the compounds involved in this embodiment, it is also preferred that the R in the above general formula (1D-C1) does not form the aforementioned substituted or unsubstituted monocyclic ring and does not form the aforementioned substituted or unsubstituted fused ring. 21 ~R 29 At least one of them, or R in the above general formula (1D-C3) 21 ~R 27 R 29 and R 30 At least one of them is a group other than a hydrogen atom.

[1141] In the compounds involved in this embodiment, it is also preferred that the R in the above general formula (1D-C1) does not form the aforementioned substituted or unsubstituted monocyclic ring and does not form the aforementioned substituted or unsubstituted fused ring. 21 ~R 29 At least one of them, or R in the above general formula (1D-C3) 21 ~R 27 R 29 and R 30 At least one of them is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.

[1142] In the compounds involved in this embodiment, it is also preferred that the R in the above general formula (1D-C1) does not form the aforementioned substituted or unsubstituted monocyclic ring and does not form the aforementioned substituted or unsubstituted fused ring.21 ~R 29 At least one of them, or R in the above general formula (1D-C3) 21 ~R 27 R 29 and R 30 At least one of them is a substituted or unsubstituted phenyl group.

[1143] In the compounds involved in this embodiment, it is also preferred that the group represented by the above general formula (1D-C) is the group represented by the above general formula (1D-C1).

[1144] Among the compounds involved in this embodiment, R5, R6, R7, R8, and R are also preferred. 11 and R 12 One of them is a group represented by the general formula (1D-C) above.

[1145] Among the compounds involved in this embodiment, R6, R7, and R are also preferred. 11 and R 12 One of them is a group represented by the general formula (1D-C) above.

[1146] Among the compounds involved in this embodiment, R is also preferred. 11 The group is represented by the general formula (1D-C) above.

[1147] Among the compounds involved in this embodiment, R is also preferred. 12 The group is represented by the general formula (1D-C) above.

[1148] Among the compounds involved in this embodiment, R is also preferred. 11 The groups represented by the above general formula (1D-C), R 12 It is an unsubstituted phenyl, or R 12 The groups represented by the above general formula (1D-C), R 11 It is an unsubstituted phenyl group.

[1149] Among the compounds involved in this embodiment, R is also preferred. 11 For the group represented by the above general formula (1D-C), R 12 It is an unsubstituted phenyl group.

[1150] Among the compounds involved in this embodiment, R is also preferred. 12 For the group represented by the above general formula (1D-C), R 11 It is an unsubstituted phenyl group.

[1151] The compounds involved in this embodiment are preferably those represented by the following general formula (1C-C-1).

[1152] The compounds involved in this embodiment are preferably those represented by the following general formula (1C-C-2).

[1153]

Chemical Formula 36

[1154]

[1155]

Chemical Formula 37

[1156]

[1157] (R1~R in the above general formula (1C-C-1)) 11 and R1 to R in the above general formula (1C-C-2) 10 and R 12 Each independently

[1158] hydrogen atom,

[1159] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1160] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[1161] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1162] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1163] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1164] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1165] -O-(R 904 The groups shown in the figure,

[1166] -S-(R 905 The groups shown in the figure,

[1167] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[1168] -C(=O)R 801 The groups shown

[1169] -COOR 802 The groups shown

[1170] Halogen atoms,

[1171] cyano,

[1172] Nitro,

[1173] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1174] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1175] R in the above general formulas (1C-C-1) and (1C-C-2) 21 ~R 29 Each independently

[1176] hydrogen atom,

[1177] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1178] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1179] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1180] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1181] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1182] -O-(R 904 The groups shown in the figure,

[1183] -S-(R 905 The groups shown in the figure,

[1184] -N(R 906 (R) 907 The groups shown in the figure,

[1185] Halogen atoms,

[1186] cyano,

[1187] Nitro,

[1188] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1189] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1190] Among the compounds involved in this embodiment, R is also preferred. 12 It is a hydrogen atom.

[1191] In the compounds involved in this embodiment, it is also preferable that they have one or more deuterium atoms in the molecule.

[1192] In the compounds involved in this embodiment, it is also preferred that R1 to R3, R9 are hydrogen atoms, and that R4 to R8 and R9 are hydrogen atoms other than the groups shown in the above general formula (1D-C). 10 ~R 12 And R when it is a hydrogen atom 21 ~R 30 One or more of them are deuterium atoms.

[1193] In the compounds involved in this embodiment, it is also preferred that R1 to R3, R9 are hydrogen atoms, and that R4 to R8 and R9 are hydrogen atoms other than the groups shown in the above general formula (1D-C). 10 ~R 12 And R when it is a hydrogen atom 21 ~R 30 All are deuterium atoms.

[1194] In the compounds involved in this embodiment, it is also preferred that R1 to R3, R9 are groups other than hydrogen atoms, and that R4 to R8 and R9 are groups other than hydrogen atoms, excluding the groups shown in the above general formula (1D-C). 10 ~R 12 And R when it is a group other than a hydrogen atom 21 ~R 30 When each hydrogen atom is present, one or more of these hydrogen atoms are deuterium atoms.

[1195] In the compounds involved in this embodiment, it is also preferred that R1 to R3, R9 are groups other than hydrogen atoms, and that R4 to R8 and R9 are groups other than hydrogen atoms, excluding the groups shown in the above general formula (1D-C). 10 ~R 12 And R when it is a group other than a hydrogen atom 21 ~R 30 When each hydrogen atom is present, all hydrogen atoms are deuterium atoms.

[1196] Among the compounds involved in this embodiment, compounds that do not contain heteroatoms in their molecules are preferred.

[1197] In the compounds involved in this embodiment, it is also preferred that the groups described as "substituted or unsubstituted" are all "unsubstituted" groups, and the rings described as "substituted or unsubstituted" are all "unsubstituted" rings.

[1198] • Method for manufacturing the compound involved in this embodiment

[1199] The compounds involved in this embodiment can be manufactured according to the synthesis method described in the examples below. Alternatively, the compounds involved in this embodiment can also be manufactured by using known alternative reactions and starting materials corresponding to the target substance, following the same synthesis method.

[1200] Specific examples of compounds involved in this embodiment

[1201] As a specific example of the compounds involved in this embodiment, for example, the compounds that fall within the scope of the compounds involved in this embodiment are examples of the compounds shown in the compound of general formula (1C) used as the first compound in the organic electroluminescent element of the fourth embodiment described later.

[1202] [Fourth Implementation Method]

[1203] (Organic electroluminescent device)

[1204] The organic EL element involved in this embodiment will be described.

[1205] The organic EL element involved in this embodiment contains, in one embodiment, the compound involved in the first embodiment, the second embodiment, or the third embodiment.

[1206] The organic EL element according to this embodiment has an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer comprises at least one layer formed of an organic compound. Alternatively, the organic layer is formed by stacking multiple layers formed of organic compounds. The organic layer may also further comprise inorganic compounds.

[1207] In one embodiment of the organic EL element, at least one layer of the organic layer contains the compound of the first embodiment.

[1208] In one embodiment of the organic EL element, at least one layer of the organic layer contains the compound described in the second embodiment.

[1209] In one embodiment of the organic EL element, at least one layer of the organic layer contains the compound described in the third embodiment.

[1210] In the organic EL element of this embodiment, it is preferable that at least one of the organic layers has a light-emitting region. In the organic EL element of this embodiment, the light-emitting region preferably contains at least one light-emitting layer. In one embodiment, the light-emitting layer contains a compound represented by the above-described general formula (1C-A). In one embodiment, the light-emitting layer contains a compound represented by the above-described general formula (1C-B). In one embodiment, the light-emitting layer contains a compound represented by the above-described general formula (1C-C).

[1211] Preferably, the organic EL element according to this embodiment has an anode, a cathode and a light-emitting region disposed between the anode and the cathode, the light-emitting region including a first light-emitting layer and a second light-emitting layer, the first light-emitting layer containing a compound represented by the above general formula (1C-A) as a first compound, and the second light-emitting layer containing a second compound.

[1212] In the organic EL element of this embodiment, the compound represented by the above general formula (1C-A) is a different compound from the second compound.

[1213] Preferably, the organic EL element according to this embodiment has an anode, a cathode and a light-emitting region disposed between the anode and the cathode, the light-emitting region including a first light-emitting layer and a second light-emitting layer, the first light-emitting layer containing a compound represented by the above general formula (1C-B) as a first compound, and the second light-emitting layer containing a second compound.

[1214] In the organic EL element of this embodiment, the compound represented by the above general formula (1C-B) is a different compound from the second compound.

[1215] Preferably, the organic EL element according to this embodiment has an anode, a cathode and a light-emitting region disposed between the anode and the cathode, the light-emitting region includes a first light-emitting layer and a second light-emitting layer, the first light-emitting layer contains a compound represented by the general formula (1C-C) as a first compound, and the second light-emitting layer contains a second compound.

[1216] In the organic EL element of this embodiment, the compound represented by the above general formula (1C-C) is a different compound from the second compound.

[1217] In one embodiment, the organic EL element has an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer has a light-emitting region, which includes a first light-emitting layer and a second light-emitting layer. The first light-emitting layer contains a first compound represented by the following general formula (1C), and the second light-emitting layer contains a second compound.

[1218] [Chemical Formula 38]

[1219]

[1220] (In the above general formula (1C),

[1221] R4~R8 and R 10 ~R 12 One of them is a group represented by the general formula (1D) above.

[1222] R1 to R3, R9, and R4 to R8 and R9 other than the groups shown in the above general formula (1D). 10 ~R 12 Each independently

[1223] hydrogen atom,

[1224] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1225] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[1226] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1227] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1228] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1229] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1230] -O-(R 904 The groups shown in the figure,

[1231] -S-(R 905 The groups shown in the figure,

[1232] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[1233] -C(=O)R 801 The groups shown

[1234] -COOR 802 The groups shown

[1235] Halogen atoms,

[1236] cyano,

[1237] Nitro,

[1238] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1239] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1240] In R 11 In the case of a group represented by the above general formula (1D), R 12 A phenyl group consisting of a hydrogen atom or with or without substitution.

[1241] In R 12 In the case of a group represented by the above general formula (1D), R11 A phenyl group consisting of a hydrogen atom or with or without substitution.

[1242] In the above general formula (1D), R 21 ~R 30 One of them represents the bonding position with the benzo[a]anthracene ring in the above general formula (1C), and the R in the above general formula (1D) is not at that bonding position. 21 ~R 30 One or more groups consisting of two or more adjacent elements.

[1243] They bond together to form substituted or unsubstituted monocyclic rings.

[1244] They bond together to form substituted or unsubstituted fused rings, or

[1245] They do not bond with each other.

[1246] The R in the above general formula (1D) is not bonded to the benzo[a]anthracene ring in the above general formula (1C), does not form the above-mentioned substituted or unsubstituted monocyclic ring, and does not form the above-mentioned substituted or unsubstituted fused ring. 21 ~R 30 Each independently

[1247] hydrogen atom,

[1248] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1249] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1250] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1251] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1252] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1253] -O-(R 904 The groups shown in the figure,

[1254] -S-(R 905 The groups shown in the figure,

[1255] -N(R 906 (R) 907 The groups shown in the figure,

[1256] Halogen atoms,

[1257] cyano,

[1258] Nitro,

[1259] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1260] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1261] In the compounds represented by the above general formula (1C), R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently

[1262] hydrogen atom,

[1263] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1264] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1265] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1266] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1267] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.

[1268] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.

[1269] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.

[1270] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.

[1271] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.

[1272] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.

[1273] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.

[1274] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[1275] In R 802 In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)

[1276] In one embodiment of the organic electroluminescent element, it is also preferred that the R in the above general formula (1D) is not bonded to the benzo[a]anthracene ring in the above general formula (1C), does not form the above-mentioned substituted or unsubstituted monocyclic ring, and does not form the above-mentioned substituted or unsubstituted fused ring. 21 ~R 30 At least one of them is a group other than a hydrogen atom.

[1277] In one embodiment of the organic electroluminescent element, it is also preferred that the R in the above general formula (1D) is not bonded to the benzo[a]anthracene ring in the above general formula (1C), does not form the above-mentioned substituted or unsubstituted monocyclic ring, and does not form the above-mentioned substituted or unsubstituted fused ring. 21 ~R 30 At least one of them is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.

[1278] In one embodiment of the organic electroluminescent element, it is also preferred that the R in the above general formula (1D) is not bonded to the benzo[a]anthracene ring in the above general formula (1C), does not form the above-mentioned substituted or unsubstituted monocyclic ring, and does not form the above-mentioned substituted or unsubstituted fused ring. 21 ~R 30 At least one of them is a substituted or unsubstituted phenyl group.

[1279] In one embodiment of the organic electroluminescent element, it is also preferred that the group represented by the above general formula (1D) is the group represented by the following general formula (1D-1), general formula (1D-2) or general formula (1D-3).

[1280] [Chemical Formula 39]

[1281]

[1282] (In the above general formula (1D-1),

[1283] By R 21 ~R 29 One or more groups consisting of two or more adjacent elements.

[1284] They bond together to form substituted or unsubstituted monocyclic rings.

[1285] They bond together to form substituted or unsubstituted fused rings, or

[1286] They do not bond with each other.

[1287] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 21 ~R 29 Each independently

[1288] hydrogen atom,

[1289] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1290] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1291] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1292] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1293] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1294] -O-(R 904 The groups shown in the figure,

[1295] -S-(R 905 The groups shown in the figure,

[1296] -N(R 906 (R) 907 The groups shown in the figure,

[1297] Halogen atoms,

[1298] cyano,

[1299] Nitro,

[1300] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1301] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1302] * indicates the bonding position with the benzo[a]anthracene ring in the above general formula (1C).

[1303] In the above general formula (1D-2),

[1304] By R 21 ~R 28 and R 30 One or more groups consisting of two or more adjacent elements.

[1305] They bond together to form substituted or unsubstituted monocyclic rings.

[1306] They bond together to form substituted or unsubstituted fused rings, or

[1307] They do not bond with each other.

[1308] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 21 ~R 28 and R 30 Each independently relates to R in the above general formula (1D-1). 21 ~R 29 Same meaning

[1309] * indicates the bonding position with the benzo[a]anthracene ring in the above general formula (1C).

[1310] In the above general formula (1D-3),

[1311] By R 21 ~R 27 R 29 and R 30 One or more groups consisting of two or more adjacent elements.

[1312] They bond together to form substituted or unsubstituted monocyclic rings.

[1313] They bond together to form substituted or unsubstituted fused rings, or

[1314] They do not bond with each other.

[1315] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 21 ~R 27 R 29 and R 30 Each independently relates to R in the above general formula (1D-1). 21 ~R 29 Same meaning

[1316] * indicates the bonding position with the benzo[a]anthracene ring in the above general formula (1C).

[1317] In one embodiment of the organic electroluminescent element, it is also preferred that R in the above general formula (1D-1) does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 21 ~R 29 At least one of them, R in the above general formula (1D-2) 21 ~R 28 and R 30At least one of them, or R in the above general formula (1D-3) 21 ~R 27 R 29 and R 30 At least one of them is a group other than a hydrogen atom.

[1318] In one embodiment of the organic electroluminescent element, it is also preferred that R in the above general formula (1D-1) does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 21 ~R 29 At least one of them, R in the above general formula (1D-2) 21 ~R 28 and R 30 At least one of them, or R in the above general formula (1D-3) 21 ~R 27 R 29 and R 30 At least one of them is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.

[1319] In one embodiment of the organic electroluminescent element, it is also preferred that R in the above general formula (1D-1) does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 21 ~R 29 At least one of them, R in the above general formula (1D-2) 21 ~R 28 and R 30 At least one of them, or R in the above general formula (1D-3) 21 ~R 27 R 29 and R 30 At least one of them is a substituted or unsubstituted phenyl group.

[1320] In one embodiment of the organic electroluminescent element, it is also preferred that the group represented by the above general formula (1D) is the group represented by the above general formula (1D-1).

[1321] In one embodiment of the organic electroluminescent element, it is also preferred that R5, R6, R7, R8, and R... are present in the compound represented by the above general formula (1C). 11 and R 12 One of them is a group represented by the general formula (1D) above.

[1322] In one embodiment of the organic electroluminescent element, it is also preferred that R6, R7, and R... are present in the compound represented by the above general formula (1C). 11 and R12 One of them is a group represented by the general formula (1D) above.

[1323] In one embodiment of the organic electroluminescent element, it is also preferred that R is a compound represented by the above general formula (1C). 11 The group is represented by the general formula (1D) above.

[1324] In one embodiment of the organic electroluminescent element, it is also preferred that R is a compound represented by the above general formula (1C). 12 The group is represented by the general formula (1D) above.

[1325] In one embodiment of the organic electroluminescent element, it is also preferred that R is a compound represented by the above general formula (1C). 11 The groups represented by the above general formula (1D), R 12 It is an unsubstituted phenyl, or R 12 The groups represented by the above general formula (1D), R 11 It is an unsubstituted phenyl group.

[1326] In one embodiment of the organic electroluminescent element, it is also preferred that R is a compound represented by the above general formula (1C). 11 For the group represented by the above general formula (1D), R 12 It is an unsubstituted phenyl group.

[1327] In one embodiment of the organic electroluminescent element, it is also preferred that R is a compound represented by the above general formula (1C). 12 For the group represented by the above general formula (1D), R 11 It is an unsubstituted phenyl group.

[1328] In one embodiment of the organic electroluminescent element, the compound represented by the above general formula (1C) is preferably a compound represented by the following general formula (1C-1).

[1329] In one embodiment of the organic electroluminescent element, the compound represented by the above general formula (1C) is preferably a compound represented by the following general formula (1C-2).

[1330]

Chemical Formula 40

[1331]

[1332]

Chemical Formula 41

[1333]

[1334] (R1~R in the above general formula (1C-1)) 11 and R1 to R in the above general formula (1C-2) 10 and R 12 Each independently

[1335] hydrogen atom,

[1336] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1337] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[1338] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1339] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1340] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1341] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1342] -O-(R 904 The groups shown in the figure,

[1343] -S-(R 905 The groups shown in the figure,

[1344] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[1345] -C(=O)R 801 The groups shown

[1346] -COOR 802 The groups shown

[1347] Halogen atoms,

[1348] cyano,

[1349] Nitro,

[1350] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1351] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1352] R in the above general formulas (1C-1) and (1C-2) 21 ~R 28 and R 30 Each independently

[1353] hydrogen atom,

[1354] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1355] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1356] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1357] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1358] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1359] -O-(R 904 The groups shown in the figure,

[1360] -S-(R 905 The groups shown in the figure,

[1361] -N(R 906 (R) 907 The groups shown in the figure,

[1362] Halogen atoms,

[1363] cyano,

[1364] Nitro,

[1365] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1366] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1367] In one embodiment of the organic electroluminescent element, it is also preferred that R is a compound represented by the above general formula (1C). 12 For the group represented by the above general formula (1D), R 11 It is a hydrogen atom.

[1368] In one embodiment of the organic electroluminescent element, R is also preferred. 12 For the group represented by the above general formula (1D), R 11 The phenyl group can be substituted or unsubstituted.

[1369] In one embodiment of the organic electroluminescent element, it is also preferred that, in the compound represented by the above general formula (1C), R1 to R3, R9, and R4 to R8 and R9 other than the groups represented by the above general formula (1D) are present. 10 ~R 12 Each is an aryl group consisting of a hydrogen atom, or a substituted or unsubstituted cyclic carbon group with 6 to 50 carbon atoms.

[1370] In one embodiment of the organic electroluminescent element, it is also preferred that the R in the above general formula (1D) is not bonded to the benzo[a]anthracene ring in the above general formula (1C), does not form the above-mentioned substituted or unsubstituted monocyclic ring, and does not form the above-mentioned substituted or unsubstituted fused ring. 21 ~R 30 Each is an aryl group consisting of a hydrogen atom, or a substituted or unsubstituted cyclic carbon group with 6 to 50 carbon atoms.

[1371] One embodiment of this invention involves an organic electroluminescent element that is preferably a compound that does not contain heteroatoms in its molecule.

[1372] In one embodiment of the organic electroluminescent element, it is also preferred that all groups described as "substituted or unsubstituted" are "unsubstituted" groups, and all rings described as "substituted or unsubstituted" are "unsubstituted" rings.

[1373] In one embodiment of the organic electroluminescent element, it is also preferred that R in the compound represented by the above general formula (1C) is... 12 It is a hydrogen atom.

[1374] In one embodiment of the organic electroluminescent element, it is also preferred that the compound represented by the above general formula (1C) has one or more deuterium atoms in the molecule.

[1375] In one embodiment of the organic electroluminescent element, it is also preferred that R1 to R3, R9, which are hydrogen atoms in the compound represented by the general formula (1C), and R4 to R8, which are hydrogen atoms other than those represented by the general formula (1D). 10 ~R 12 And R when it is a hydrogen atom 21 ~R 30 One or more of them are deuterium atoms.

[1376] In one embodiment of the organic electroluminescent element, it is also preferred that R1 to R3, R9, which are hydrogen atoms in the compound represented by the general formula (1C), and R4 to R8, which are hydrogen atoms other than those represented by the general formula (1D). 10 ~R 12 And R when it is a hydrogen atom 21 ~R 30 All are deuterium atoms.

[1377] In one embodiment of the organic electroluminescent element, it is also preferred that, in the compound represented by the above general formula (1C), R1 to R3, R9 are groups other than hydrogen atoms, and R4 to R8 and R9 are groups other than hydrogen atoms, excluding those represented by the above general formula (1D). 10 ~R 12 And R when it is a group other than a hydrogen atom 21 ~R 30 When each hydrogen atom is present, one or more of these hydrogen atoms are deuterium atoms.

[1378] In one embodiment of the organic electroluminescent element, it is also preferred that, in the compound represented by the above general formula (1C), R1 to R3, R9 are groups other than hydrogen atoms, and R4 to R8 and R9 are groups other than hydrogen atoms, excluding those represented by the above general formula (1D). 10 ~R 12 And R when it is a group other than a hydrogen atom 21 ~R 30 When each hydrogen atom is present, all hydrogen atoms are deuterium atoms.

[1379] In one embodiment of the organic electroluminescent element, the compounds represented by the above general formula (1C) contain R4, R5, R6, R7, R8, and R... 10 R 11 Or R 12 The group is represented by the general formula (1D) above.

[1380] In one embodiment of the organic electroluminescent element, R4, R5, R6, R7, R8, and R... of the compounds represented by the above general formula (1C-A) 10 R 11 Or R 12 The group is represented by the general formula (1D-A) above.

[1381] In one embodiment of the organic electroluminescent element, R4, R5, R6, R8, and R... of the compounds represented by the above general formula (1C-B) 10 R 11 Or R 12 The group is represented by the general formula (1D-B) above.

[1382] In one embodiment of the organic electroluminescent element, R4, R5, R6, R7, R8, and R... of the compounds represented by the above general formula (1C-C) 10 R 11 Or R 12 The group is represented by the general formula (1D-C) above.

[1383] By using R4, R5, R6, R7, R8, R, which are positions with higher electron density in HOMO and LUMO or lower singlet state energy S1, 10 R 11 Or R 12 The group is selected from any one of the groups shown in the above general formula (1D), the above general formula (1D-A), and the above general formula (1D-C), thereby easily improving the excitation resistance and easily obtaining the long-lifetime effect of organic EL elements.

[1384] By using R4, R5, R6, R8, R, which are positions with higher electron density in HOMO and LUMO or lower singlet state energy S1, 10 R 11 Or R 12 The groups represented by the above general formula (1D-B) can easily improve the excitation resistance and achieve a longer lifetime for organic EL elements.

[1385] When the first compound used in the first luminescent layer has a structure in which the group shown in the above general formula (1D), the group shown in the above general formula (1D-A), the group shown in the above general formula (1D-B), or the group shown in the above general formula (1D-C) is directly connected to the benzo[a]anthracene ring, it is believed that the triplet energy T1 is distributed on both sides of the pyrene skeleton in the benzo[a]anthracene ring and the group shown in the above general formula (1D), the group shown in the above general formula (1D-A), the group shown in the above general formula (1D-B), and the group shown in the above general formula (1D-C), thus resulting in a long lifetime.

[1386] • Method for preparing the compound represented by general formula (1C)

[1387] The compound represented by general formula (1C) can be manufactured according to the synthetic method described in the examples below. Alternatively, the compound represented by general formula (1C) can also be manufactured by analogy with this synthetic method, using known alternative reactions and starting materials corresponding to the target substance.

[1388] Specific examples of compounds represented by general formula (1C)

[1389] Specific examples of compounds represented by general formula (1C) include the following compounds. However, the present invention is not limited to these specific examples. In this specification, the deuterium atom is designated as D in the chemical formula, and the protium atom is designated as H or omitted.

[1390]

Chemical Formula 42

[1391]

[1392]

Chemical Formula 43

[1393]

[1394]

Chemical Formula 44

[1395]

[1396] [Chemical Formula 45]

[1397]

[1398]

Chemical Formula 46

[1399]

[1400] [Chemical Formula 47]

[1401]

[1402] [Chemical Formula 48]

[1403]

[1404] [Chemical Formula 49]

[1405]

[1406] [Chemical Formula 50]

[1407]

[1408]

Chemical Formula 51

[1409]

[1410]

Chemical Formula 52

[1411]

[1412]

Chemical Formula 53

[1413]

[1414] [Chemical Formula 54]

[1415]

[1416]

Chemical Formula 55

[1417]

[1418] [Chemical Formula 56]

[1419]

[1420] [Chemical Formula 57]

[1421]

[1422] [Chemical Formula 58]

[1423]

[1424] [Chemical Formula 59]

[1425]

[1426] [Chemical Formula 60]

[1427]

[1428]

Chemical Formula 61

[1429]

[1430]

Chemical Formula 62

[1431]

[1432]

Chemical Formula 63

[1433]

[1434]

Chemical Formula 64

[1435]

[1436] In the case where the light-emitting region includes a first light-emitting layer and a second light-emitting layer, the organic EL element involved in this embodiment may, for example, have an anode, a first light-emitting layer, a second light-emitting layer and a cathode in sequence, or the order of the first light-emitting layer and the second light-emitting layer may be reversed so that the anode, the second light-emitting layer, the first light-emitting layer and the cathode are in sequence.

[1437] In cases where the light-emitting region includes a first light-emitting layer and a second light-emitting layer, it is also preferable that the organic EL element according to this embodiment includes a second light-emitting layer located between the anode and the cathode, and a first light-emitting layer is disposed between the anode and the second light-emitting layer.

[1438] In cases where the light-emitting region includes a first light-emitting layer and a second light-emitting layer, it is also preferable that the organic EL element according to this embodiment includes a first light-emitting layer located between the anode and the cathode, and a second light-emitting layer disposed between the anode and the first light-emitting layer.

[1439] (Emitting wavelength of organic EL devices)

[1440] The organic EL element involved in this embodiment preferably emits light with a maximum peak wavelength of less than 500 nm when the element is driven, and more preferably emits light with a wavelength of more than 430 nm and less than 480 nm.

[1441] The maximum peak wavelength of light emitted by the organic EL element during element driving was determined as follows. A CS-2000 spectroradiometer (manufactured by Konica Minolta) was used to measure the wavelength of light emitted by the organic EL element when a voltage was applied to achieve a current density of 10 mA / cm². 2 The spectroscopic emission intensity spectrum at that time was obtained. In the obtained spectroscopic emission intensity spectrum, the peak wavelength of the emission spectrum where the luminous intensity reaches its maximum was measured and taken as the maximum peak wavelength (unit: nm).

[1442] The method for determining the maximum peak wavelength of the compounds described in this specification is as follows. 10 [units of measurement] of the compound to be measured were prepared. -6 mol / L or higher and 10 -5 A toluene solution with a concentration of less than mol / L was added to a quartz cuvette, and the emission spectrum of the sample was measured at room temperature (300K) (vertical axis is set as emission intensity, and horizontal axis is set as wavelength). The emission spectrum can be measured using a spectrophotometer (device name: F-7000) manufactured by Hitachi Advanced Scientific Corporation. It should be noted that the emission spectrum measurement device is not limited to the device used here.

[1443] In the emission spectrum, the peak wavelength of the emission spectrum with the highest emission intensity is taken as the maximum emission peak wavelength. It should be noted that in this specification, the maximum peak wavelength is sometimes referred to as the fluorescence emission maximum peak wavelength (FL-peak).

[1444] In the organic EL element of this embodiment, the organic layer may consist of only the light-emitting layer. As the organic layer, it may also have at least one layer selected from hole injection layer, hole transport layer, electron injection layer, electron transport layer, hole blocking layer and electron blocking layer.

[1445] In the organic EL element of this embodiment, a hole transport layer is preferably provided between the anode and the light-emitting region.

[1446] In the organic EL element according to this embodiment, when the light-emitting region includes a first light-emitting layer and a second light-emitting layer, and the stacking order of the first light-emitting layer and the second light-emitting layer is from the anode side in the order of the first light-emitting layer and the second light-emitting layer, it is preferable to have a hole transport layer between the anode and the first light-emitting layer. Furthermore, when the stacking order of the first light-emitting layer and the second light-emitting layer is from the anode side in the order of the second light-emitting layer and the first light-emitting layer, it is preferable to have a hole transport layer between the anode and the second light-emitting layer.

[1447] In the organic EL element involved in this embodiment, it is preferable to have an electron transport layer between the cathode and the light-emitting region.

[1448] In the organic EL element according to this embodiment, when the light-emitting region includes a first light-emitting layer and a second light-emitting layer, and the stacking order of the first and second light-emitting layers is from the anode side to the second light-emitting layer, it is preferable to have an electron transport layer between the cathode and the second light-emitting layer. Furthermore, when the stacking order of the first and second light-emitting layers is from the anode side to the second light-emitting layer and the first light-emitting layer, it is preferable to have an electron transport layer between the cathode and the first light-emitting layer.

[1449] Figure 1 The general configuration of an example of an organic EL element involved in this embodiment is shown.

[1450] Figure 1 The organic EL element 1A shown includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10A disposed between the anode 3 and the cathode 4. From the anode 3 side, the organic layer 10A sequentially includes a hole transport region 6, a light-emitting region 5A, and an electron transport region 7. From the anode 3 side, the hole transport region 6 sequentially includes a hole injection layer 61 and a hole transport layer 62. The light-emitting region 5A includes a single light-emitting layer 5. From the light-emitting region 5A side, the electron transport region 7 sequentially includes an electron transport layer 71 and an electron injection layer 72.

[1451] (Emitting layer)

[1452] The light-emitting layer 5 contains the compound involved in the first embodiment, the compound involved in the second embodiment, or the compound involved in the third embodiment.

[1453] In the organic EL element 1A, the compound contained in the light-emitting layer 5 is preferably a compound represented by the above general formula (1C-A).

[1454] In the organic EL element 1A, the compound contained in the light-emitting layer 5 is preferably a compound represented by the above general formula (1C-B).

[1455] In the organic EL element 1A, the compound contained in the light-emitting layer 5 is preferably a compound represented by the above general formula (1C-C).

[1456] (Luminescent compounds)

[1457] In the organic EL element 1A, the light-emitting layer 5 preferably also contains a light-emitting compound (preferably a fluorescent compound).

[1458] The luminescent compounds contained in the luminescent layer 5 can be selected from...

[1459] The compounds represented by the following general formula (3),

[1460] The compounds represented by the following general formula (4),

[1461] The compounds represented by the following general formula (5),

[1462] The compounds represented by the following general formula (6),

[1463] The compounds represented by the following general formula (7),

[1464] The compounds represented by the following general formula (8),

[1465] The compounds represented by the following general formula (9), and

[1466] One or more of the compounds represented by the following general formula (10).

[1467] (The compound represented by general formula (3))

[1468] The compounds represented by general formula (3) will be described.

[1469]

Chemical Formula 65

[1470]

[1471] (In the above general formula (3),

[1472] By R 301 ~R 310 One or more groups consisting of two or more adjacent elements.

[1473] They bond together to form substituted or unsubstituted monocyclic rings.

[1474] They bond together to form substituted or unsubstituted fused rings, or

[1475] They are not mutually bonded.

[1476] R 301 ~R 310 At least one of them is a monovalent group represented by the following general formula (31),

[1477] R that does not form the above-mentioned monocyclic ring, does not form the above-mentioned fused ring, and is not a monovalent group represented by the following general formula (31) 301 ~R 310 Each independently

[1478] hydrogen atom,

[1479] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1480] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1481] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1482] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1483] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1484] -O-(R 904 The groups shown in the figure,

[1485] -S-(R 905 The groups shown in the figure,

[1486] -N(R 906 (R) 907 The groups shown in the figure,

[1487] Halogen atoms,

[1488] cyano,

[1489] Nitro,

[1490] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1491] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1492]

Chemical Formula 66

[1493]

[1494] (In the above general formula (31),

[1495] Ar 301 and Ar 302 Each independently

[1496] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1497] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1498] L 301 ~L 303 Each independently

[1499] single bond,

[1500] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or

[1501] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.

[1502] * indicates the bonding position in the pyrene ring in the above general formula (3).

[1503] In luminescent compounds, R 901 R 902 R 903 R 904 R 905 R 906 and R 907 Each independently

[1504] hydrogen atom,

[1505] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1506] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1507] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1508] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1509] Preferably, it is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[1510] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.

[1511] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.

[1512] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.

[1513] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.

[1514] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.

[1515] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.

[1516] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.

[1517] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.

[1518] In the above general formula (3), R is preferred. 301 ~R 310 Two of them are groups represented by the general formula (31) above.

[1519] In one embodiment, the compound represented by the above general formula (3) is the compound represented by the following general formula (33).

[1520] [Chemical Formula 67]

[1521]

[1522] (In the above general formula (33),

[1523] R 311 ~R 318 Each independently interacts with the R group in the above general formula (3) that is not a monovalent group represented by the above general formula (31). 301 ~R 310 Same meaning

[1524] L 311 ~L 316 Each independently

[1525] single bond,

[1526] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or

[1527] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.

[1528] Ar 312 Ar 313 Ar 315 and Ar 316 Each independently

[1529] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1530] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1531] In the above general formula (31), L 301 Preferably a single bond, L 302 and L 303 Single bonds are preferred.

[1532] In one embodiment, the compound represented by the above general formula (3) is represented by the following general formula (34) or general formula (35).

[1533]

Chemical Formula 68

[1534]

[1535] (In the above general formula (34),

[1536] R 311 ~R 318 Each independently interacts with the R group in the above general formula (3) that is not a monovalent group represented by the above general formula (31). 301 ~R 310 Same meaning

[1537] L 312 L 313 L 315 and L 316 Each independently relates to L in the above general formula (33) 312 L 313 L 315 and L 316 Same meaning

[1538] Ar 312 Ar 313 Ar 315 and Ar 316 Each independently relates to Ar in the above general formula (33) 312 Ar 313 Ar 315 and Ar 316 The meaning is the same.

[1539]

Chemical Formula 69

[1540]

[1541] (In the above general formula (35),

[1542] R 311 ~R 318 Each independently interacts with the R group in the above general formula (3) that is not a monovalent group represented by the above general formula (31). 301 ~R 310 Same meaning

[1543] Ar 312 Ar 313 Ar 315 and Ar 316 Each independently relates to Ar in the above general formula (33) 312 Ar 313 Ar 315 and Ar 316 The meaning is the same.

[1544] In the above general formula (31), Ar is preferred. 301 and Ar 302 At least one of them is a group represented by the following general formula (36).

[1545] In the above general formulas (33) to (35), Ar is preferred. 312 and Ar 313 At least one of them is a group represented by the following general formula (36).

[1546] In the above general formulas (33) to (35), Ar is preferred. 315 and Ar 316 At least one of them is a group represented by the following general formula (36).

[1547] [Chemical Formula 70]

[1548]

[1549] (In the above general formula (36),

[1550] X3 represents an oxygen atom or a sulfur atom.

[1551] By R 321 ~R 327 One or more groups consisting of two or more adjacent elements.

[1552] They bond together to form substituted or unsubstituted monocyclic rings.

[1553] They bond together to form substituted or unsubstituted fused rings, or

[1554] They do not bond with each other.

[1555] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 321 ~R 327 Each independently

[1556] hydrogen atom,

[1557] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1558] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1559] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1560] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1561] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1562] -O-(R 904 The groups shown in the figure,

[1563] -S-(R 905 The groups shown in the figure,

[1564] -N(R 906 (R) 907 The groups shown in the figure,

[1565] Halogen atoms,

[1566] cyano,

[1567] Nitro,

[1568] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1569] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1570] * indicates that L 302 L 303 L 312 L 313 L 315 or L 316 (The bonding location.)

[1571] X3 is preferably an oxygen atom.

[1572] Preferably, R 321 ~R 327 At least one of them is

[1573] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1574] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1575] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1576] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1577] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1578] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[1579] In the above general formula (31), it is preferred that Ar 301 For the group represented by the above general formula (36), Ar 302 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[1580] In the above general formulas (33) to (35), Ar is preferred. 312 For the group represented by the above general formula (36), Ar 313 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[1581] In the above general formulas (33) to (35), Ar is preferred. 315 For the group represented by the above general formula (36), Ar 316 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[1582] In one embodiment, the compound represented by the above general formula (3) is represented by the following general formula (37).

[1583]

Chemical Formula 71

[1584]

[1585] (In the above general formula (37),

[1586] R 311 ~R 318 Each independently interacts with the R group in the above general formula (3) that is not a monovalent group represented by the above general formula (31). 301 ~R 310 Same meaning

[1587] By R 321 ~R 327 One or more groups consisting of two or more adjacent elements.

[1588] They bond together to form substituted or unsubstituted monocyclic rings.

[1589] They bond together to form substituted or unsubstituted fused rings, or

[1590] They do not bond with each other.

[1591] By R 341 ~R 347 One or more groups consisting of two or more adjacent elements.

[1592] They bond together to form substituted or unsubstituted monocyclic rings.

[1593] They bond together to form substituted or unsubstituted fused rings, or

[1594] They do not bond with each other.

[1595] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 321 ~R 327 and R 341 ~R 347 Each independently

[1596] hydrogen atom,

[1597] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1598] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1599] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1600] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1601] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1602] -O-(R 904 The groups shown in the figure,

[1603] -S-(R 905 The groups shown in the figure,

[1604] -N(R 906 (R) 907 The groups shown in the figure,

[1605] Halogen atoms,

[1606] cyano,

[1607] Nitro,

[1608] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1609] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1610] R 331 ~R 335 and R 351 ~R 355 Each independently

[1611] hydrogen atom,

[1612] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1613] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1614] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1615] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1616] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1617] -O-(R 904 The groups shown in the figure,

[1618] -S-(R 905The groups shown in the figure,

[1619] -N(R 906 (R) 907 The groups shown in the figure,

[1620] Halogen atom, cyano group, nitro group,

[1621] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1622] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1623] As a compound represented by the above general formula (3), the following compounds can be cited as specific examples.

[1624]

Chemical Formula 72

[1625]

[1626]

Chemical Formula 73

[1627]

[1628] [Chemical Formula 74]

[1629]

[1630] [Chemical Formula 75]

[1631]

[1632] [Chemical Formula 76]

[1633]

[1634] (The compound represented by general formula (4))

[1635] The compounds represented by general formula (4) will be described.

[1636]

Chemical Formula 77

[1637]

[1638] (In the above general formula (4),

[1639] Z can be independently represented by CRa or nitrogen atoms.

[1640] Rings A1 and A2 are each independent of each other.

[1641] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or

[1642] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1643] When there are multiple Ra, one or more groups consisting of two or more adjacent Ra are selected.

[1644] They bond together to form substituted or unsubstituted monocyclic rings.

[1645] They bond together to form substituted or unsubstituted fused rings, or

[1646] They do not bond with each other.

[1647] n21 and n22 are each independently 0, 1, 2, 3 or 4.

[1648] When there are multiple Rb, one or more groups consisting of two or more adjacent Rb are considered.

[1649] They bond together to form substituted or unsubstituted monocyclic rings.

[1650] They bond together to form substituted or unsubstituted fused rings, or

[1651] They do not bond with each other.

[1652] When there are multiple Rc, one or more groups consisting of two or more adjacent Rc are considered.

[1653] They bond together to form substituted or unsubstituted monocyclic rings.

[1654] They bond together to form substituted or unsubstituted fused rings, or

[1655] They do not bond with each other.

[1656] Ra, Rb, and Rc, which do not form the aforementioned single rings and do not form the aforementioned fused rings, are each independently...

[1657] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1658] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1659] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1660] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1661] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1662] -O-(R 904 The groups shown in the figure,

[1663] -S-(R905 The groups shown in the figure,

[1664] -N(R 906 (R) 907 The groups shown in the figure,

[1665] Halogen atoms,

[1666] cyano,

[1667] Nitro,

[1668] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1669] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1670] The "aromatic hydrocarbon rings" of the A1 and A2 rings have the same structure as compounds formed by introducing hydrogen atoms into the aforementioned "aryl" group.

[1671] The "aromatic hydrocarbon rings" of A1 and A2 rings contain two carbon atoms on the fused 2-ring structure in the center of the above general formula (4) as cyclic atoms.

[1672] As a specific example of "a cyclic aromatic hydrocarbon ring with 6 to 50 carbon atoms, whether substituted or unsubstituted", compounds formed by introducing hydrogen atoms into the "aryl" group described in Specific Example Group G1 can be cited.

[1673] The "heterocyclic" rings A1 and A2 have the same structure as compounds formed by introducing hydrogen atoms into the aforementioned "heterocyclic group".

[1674] The "heterocyclic" rings A1 and A2 contain two carbon atoms on the fused 2-ring structure in the center of the above general formula (4) as cyclic atoms.

[1675] As a specific example of "a heterocycle with 5 to 50 cyclic atoms, whether substituted or unsubstituted", one can cite compounds formed by introducing hydrogen atoms into the "heterocyclic group" described in Specific Example Group G2.

[1676] Rb is bonded to any one of the carbon atoms that form an aromatic hydrocarbon ring as an Al ring, or to any one of the atoms that form a heterocycle as an Al ring.

[1677] Rc is bonded to any one of the carbon atoms that form an aromatic hydrocarbon ring as an A2 ring, or to any one of the atoms that form a heterocycle as an A2 ring.

[1678] Among Ra, Rb and Rc, at least one is preferably a group represented by the following general formula (4a), and more preferably at least two are groups represented by the following general formula (4a).

[1679] [Chemical Formula 78]

[1680]

[1681] (In the above general formula (4a),

[1682] L 401 for

[1683] single bond,

[1684] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or

[1685] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.

[1686] Ar 401 for

[1687] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms

[1688] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or

[1689] The group represented by the following general formula (4b).

[1690] [Chemical Formula 79]

[1691]

[1692] (In the above general formula (4b),

[1693] L 402 and L 403 Each independently

[1694] single bond,

[1695] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or

[1696] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.

[1697] By Ar 402 and Ar 403 Groups

[1698] They bond together to form substituted or unsubstituted monocyclic rings.

[1699] They bond together to form substituted or unsubstituted fused rings, or

[1700] They do not bond with each other.

[1701] Ar does not form the aforementioned single ring and does not form the aforementioned fused ring 402 and Ar 403 Each independently

[1702] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1703] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1704] In one embodiment, the compound represented by the above general formula (4) is represented by the following general formula (42).

[1705] [Chemical Formula 80]

[1706]

[1707] (In the above general formula (42),

[1708] By R 401 ~R 411 One or more groups consisting of two or more adjacent elements.

[1709] They bond together to form substituted or unsubstituted monocyclic rings.

[1710] They bond together to form substituted or unsubstituted fused rings, or

[1711] They do not bond with each other.

[1712] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 401 ~R 411 Each independently

[1713] hydrogen atom,

[1714] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1715] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1716] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1717] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1718] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1719] -O-(R 904 The groups shown in the figure,

[1720] -S-(R 905 The groups shown in the figure,

[1721] -N(R 906 (R) 907 The groups shown in the figure,

[1722] Halogen atoms,

[1723] cyano,

[1724] Nitro,

[1725] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1726] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1727] R 401 ~R 411 Preferably, at least one of them is a group represented by the above general formula (4a), and more preferably at least two of them are groups represented by the above general formula (4a).

[1728] Preferred R 404 and R 411 The group is represented by the general formula (4a) above.

[1729] In one embodiment, the compound represented by the above general formula (4) is a compound having the structure represented by the following general formula (4-1) or general formula (4-2) bonded to the A1 ring.

[1730] In another embodiment, the compound represented by the above general formula (42) is in R 404 ~R 407 Compounds having structures represented by the following general formula (4-1) or general formula (4-2) bonded to the bonded ring.

[1731]

Chemical Formula 81

[1732]

[1733] In the above general formula (4-1), each of the two * atoms is independently bonded to the cyclic carbon atom of the aromatic hydrocarbon ring or the cyclic atom of the heterocycle in the above general formula (4), or to the R atom in the above general formula (42). 404 ~R 407 Any one of the bonds in,

[1734] The three asterisks in the above general formula (4-2) are each independently bonded to the cyclic carbon atom of the aromatic hydrocarbon ring or the cyclic atom of the heterocycle in the above general formula (4) which is the A1 ring, or to the R in the above general formula (42). 404 ~R 407 Any one of the bonds in,

[1735] By R 421 ~R 427 One or more groups consisting of two or more adjacent elements.

[1736] They bond together to form substituted or unsubstituted monocyclic rings.

[1737] They bond together to form substituted or unsubstituted fused rings, or

[1738] They do not bond with each other.

[1739] By R 431 ~R 438 One or more groups consisting of two or more adjacent elements.

[1740] They bond together to form substituted or unsubstituted monocyclic rings.

[1741] They bond together to form substituted or unsubstituted fused rings, or

[1742] They do not bond with each other.

[1743] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 421 ~R 427 and R 431 ~R 438 Each independently

[1744] hydrogen atom,

[1745] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1746] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1747] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1748] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1749] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1750] -O-(R 904 The groups shown in the figure,

[1751] -S-(R 905 The groups shown in the figure,

[1752] -N(R 906 (R) 907 The groups shown in the figure,

[1753] Halogen atoms,

[1754] cyano,

[1755] Nitro,

[1756] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1757] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1758] In one embodiment, the compound represented by the above general formula (4) is a compound represented by the following general formula (41-3), general formula (41-4) or general formula (41-5).

[1759]

Chemical Formula 82

[1760]

[1761]

Chemical Formula 83

[1762]

[1763]

Chemical Formula 84

[1764]

[1765] (In the above general formulas (41-3), (41-4), and (41-5),

[1766] Ring A1 is defined in the same way as in general formula (4) above.

[1767] R 421 ~R 427 Each independently relates to R in the above general formula (4-1) 421 ~R 427 Same meaning

[1768] R 440 ~R 448 Each independently relates to R in the above general formula (42) 401 ~R 411 The meaning is the same.

[1769] In one embodiment, the aromatic hydrocarbon ring of the above general formula (41-5) with 6 to 50 carbon atoms, either substituted or unsubstituted for the A1 ring, is...

[1770] Substituted or unsubstituted naphthalene ring, or

[1771] Substituted or unsubstituted fluorene ring.

[1772] In one embodiment, the heterocycle of the above general formula (41-5), which has 5 to 50 cyclic atoms and is either substituted or unsubstituted for the A1 ring, is...

[1773] Substituted or unsubstituted dibenzofuran rings,

[1774] Substituted or unsubstituted carbazole ring, or

[1775] Substituted or unsubstituted dibenzothiophene ring.

[1776] In one embodiment, the compound represented by the above general formula (4) or the above general formula (42) is selected from the group consisting of the compounds represented by the following general formulas (461) to (467).

[1777]

Chemical Formula 85

[1778]

[1779]

Chemical Formula 86

[1780]

[1781]

Chemical Formula 87

[1782]

[1783]

Chemical Formula 88

[1784]

[1785]

Chemical Formula 89

[1786]

[1787] (In the above general formulas (461), (462), (463), (464), (465), (466), and (467),

[1788] R 421 ~R 427 Each independently relates to R in the above general formula (4-1) 421 ~R 427 Same meaning

[1789] R 431 ~R 438 Each independently relates to R in the above general formula (4-2) 431 ~R 438 Same meaning

[1790] R 440 ~R 448 and R 451 ~R 454 Each independently relates to R in the above general formula (42) 401 ~R 411 Same meaning

[1791] X4 represents an oxygen atom, NR 801 Or C(R) 802 (R) 803 ),

[1792] R 801 R 802 and R803 Each independently

[1793] hydrogen atom,

[1794] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1795] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1796] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1797] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1798] Preferably, it is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[1799] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.

[1800] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[1801] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.

[1802] In R 803 In the case of multiple Rs, multiple Rs 803 (They may be the same or different.)

[1803] In one embodiment, in the compound represented by the above general formula (42), R 401 ~R 411 The embodiment is described in detail in the form of a compound represented by the following general formula (45), wherein two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring.

[1804] (The compound represented by general formula (45))

[1805] The compounds represented by general formula (45) will be described.

[1806] [Chemical Formula 90]

[1807]

[1808] (In the above general formula (45),

[1809] From R 461 With R 462 The group composed of R 462 With R 463The group composed of R 464 With R 465 The group composed of R 465 With R 466 The group composed of R 466 With R 467 The group composed of R 468 With R 469 The group composed of R 469 With R 470 Groups composed of R, and groups composed of R 470 With R 471 Two or more groups selected from the groups formed by the composition of the composition bond to each other to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.

[1810] in,

[1811] By R 461 With R 462 The group composed of R 462 With R 463 The groups do not simultaneously form a ring;

[1812] By R 464 With R 465 The group composed of R 465 With R 466 The groups do not simultaneously form a ring;

[1813] By R 465 With R 466 The group composed of R 466 With R 467 The groups do not simultaneously form a ring;

[1814] By R 468 With R 469 The group composed of R 469 With R 470 The groups do not simultaneously form a ring; and

[1815] By R 469 With R 470 The group composed of R 470 With R 471 The groups do not simultaneously form a ring.

[1816] R 461 ~R 471 Two or more rings are formed that are identical or different from each other.

[1817] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 461 ~R 471 Each independently

[1818] hydrogen atom,

[1819] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1820] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1821] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1822] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1823] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1824] -O-(R 904 The groups shown in the figure,

[1825] -S-(R 905 The groups shown in the figure,

[1826] -N(R 906 (R) 907 The groups shown in the figure,

[1827] Halogen atoms,

[1828] cyano,

[1829] Nitro,

[1830] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1831] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1832] In the above general formula (45), R n With R n＋1 (n represents an integer selected from 461, 462, 464-466 and 468-470) mutually bonded with R n and R n＋1 The two bonded cyclic carbon atoms together form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring. The ring is preferably composed of atoms selected from carbon, oxygen, sulfur and nitrogen atoms, and the number of atoms in the ring is preferably 3 to 7, more preferably 5 or 6.

[1833] The compound represented by the above general formula (45) may have, for example, two, three, or four ring structures. Two or more ring structures may each reside on the same benzene ring in the parent skeleton of the above general formula (45), or they may reside on different benzene rings. For example, in the case of three ring structures, one ring structure may reside on each of the three benzene rings in the above general formula (45).

[1834] Examples of the ring structures in the compounds represented by the general formula (45) above include those represented by the general formulas (451) to (460).

[1835]

Chemical Formula 91

[1836]

[1837] (In the above general formulas (451) to (457),

[1838] *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14 represent R respectively. n and R n＋1 The two cyclic carbon atoms bonded above,

[1839] R n The bonded cyclic carbon atoms can be any one of the two cyclic carbon atoms represented by *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14.

[1840] X 45 For C(R) 4512 (R) 4513 ), NR 4514 oxygen or sulfur atoms

[1841] By R 4501 ~R 4506 and R 4512 ~R 4513 One or more groups consisting of two or more adjacent elements.

[1842] They bond together to form substituted or unsubstituted monocyclic rings.

[1843] They bond together to form substituted or unsubstituted fused rings, or

[1844] They do not bond with each other.

[1845] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 4501 ~R 4514 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.

[1846]

Chemical Formula 92

[1847]

[1848] (In the above general formulas (458) to (460),

[1849] *1 and *2, and *3 and *4 respectively represent R n and R n＋1 The two cyclic carbon atoms bonded above,

[1850] R n The bonded cyclic carbon atoms can be any one of the two cyclic carbon atoms represented by *1 and *2 or *3 and *4.

[1851] X 45 For C(R) 4512 (R) 4513 ), NR 4514 oxygen or sulfur atoms

[1852] By R 4512 ~R 4513 and R 4515 ~R 4525 One or more groups consisting of two or more adjacent elements.

[1853] They bond together to form substituted or unsubstituted monocyclic rings.

[1854] They bond together to form substituted or unsubstituted fused rings, or

[1855] They do not bond with each other.

[1856] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 4512 ~R 4513 R 4515 ~R 4521 and R 4522 ~R 4525 and R 4514 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.

[1857] In the above general formula (45), R is preferred. 462 R 464 R 465 R 470 and R 471 At least one of them (preferably R) 462 R 465 and R 470 At least one of them, further preferred R 462 () are groups that do not form ring structures.

[1858] (i) In the above general formula (45), R n With R n＋1 When the formed ring structure has substituents, the substituents,

[1859] (ii) R in the above general formula (45) that does not form a ring structure461 ~R 471 as well as

[1860] (iii) R in the above general formulas (451) to (460) 4501 ~R 4514 R 4515 ~R 4525 Each independently preferred

[1861] hydrogen atom,

[1862] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1863] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1864] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1865] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1866] -N(R 906 (R) 907 The groups shown in the figure,

[1867] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms

[1868] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or

[1869] Choose any group from the group consisting of the groups shown in the following general formulas (461) to (464).

[1870] [Chemical Formula 93]

[1871]

[1872] (In the above general formulas (461) to (464),

[1873] R d Each independently

[1874] hydrogen atom,

[1875] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1876] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1877] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1878] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1879] -Si(R 901 (R) 902 (R)903 The groups shown in the figure,

[1880] -O-(R 904 The groups shown in the figure,

[1881] -S-(R 905 The groups shown in the figure,

[1882] -N(R 906 (R) 907 The groups shown in the figure,

[1883] Halogen atoms,

[1884] cyano,

[1885] Nitro,

[1886] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1887] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1888] X 46 For C(R) 801 (R) 802 ), NR 803 oxygen or sulfur atoms

[1889] R 801 R 802 and R 803 Each independently

[1890] hydrogen atom,

[1891] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1892] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1893] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1894] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1895] Preferably, it is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[1896] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.

[1897] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[1898] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.

[1899] In R 803 In the case of multiple Rs, multiple Rs 803 They are the same or different.

[1900] p1 is 5.

[1901] p2 is 4.

[1902] p3 is 3.

[1903] p4 is 7.

[1904] In the above general formulas (461) to (464), each * independently represents a bonding position with the ring structure.

[1905] In luminescent compounds, R 901 ~R 907 Same as defined above.

[1906] In one embodiment, the compound represented by the above general formula (45) is represented by any one of the following general formulas (45-1) to (45-6).

[1907] [Chemical Formula 94]

[1908]

[1909] [Chemical Formula 95]

[1910]

[1911] (In the above general formulas (45-1) to (45-6),

[1912] Each of the rings d to i is independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.

[1913] R 461 ~R 471 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.

[1914] In one embodiment, the compound represented by the above general formula (45) is represented by any one of the following general formulas (45-7) to (45-12).

[1915] [Chemical Formula 96]

[1916]

[1917] [Chemical Formula 97]

[1918]

[1919] (In the above general formulas (45-7) to (45-12),

[1920] Rings d to f, k, and j are each independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.

[1921] R 461 ~R 471 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.

[1922] In one embodiment, the compound represented by the above general formula (45) is represented by any one of the following general formulas (45-13) to (45-21).

[1923]

Chemical Formula 98

[1924]

[1925]

Chemical Formula 99

[1926]

[1927]

Chemical Formula 100

[1928]

[1929] (In the above general formulas (45-13) to (45-21),

[1930] Each of the rings d to k is independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.

[1931] R 461 ~R 471 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.

[1932] Substituents that further have substituents, such as those found in the above-mentioned ring g or ring h, can be exemplified by...

[1933] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1934] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms

[1935] The groups represented by the above general formula (461),

[1936] The groups represented by the above general formula (463), or

[1937] The group represented by the above general formula (464).

[1938] In one embodiment, the compound represented by the above general formula (45) is represented by any one of the following general formulas (45-22) to (45-25).

[1939]

Chemical Formula 101

[1940]

[1941] (In the above general formulas (45-22) to (45-25),

[1942] X 46 and X 47 Each independently is C(R) 801 (R) 802 ), NR 803 oxygen or sulfur atoms

[1943] R 461 ~R 471 and R 481 ~R 488 Each independently relates to R in the above general formula (45) 461 ~R 471 They have the same meaning.

[1944] R 801 R 802 and R 803 Each independently

[1945] hydrogen atom,

[1946] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1947] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1948] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1949] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1950] Preferably, it is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[1951] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.

[1952] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[1953] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.

[1954] In R 803In the case of multiple Rs, multiple Rs 803 (They may be the same or different.)

[1955] In one embodiment, the compound represented by the above general formula (45) is represented by the following general formulas (45-26).

[1956]

Chemical Formula 102

[1957]

[1958] (In the above general formula (45-26),

[1959] X 46 For C(R) 801 (R) 802 ), NR 803 oxygen or sulfur atoms

[1960] R 463 R 464 R 467 R 468 R 471 and R 481 ~R 492 Each independently relates to R in the above general formula (45) 461 ~R 471 They have the same meaning.

[1961] R 801 R 802 and R 803 Each independently

[1962] hydrogen atom,

[1963] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1964] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1965] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1966] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1967] Preferably, it is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[1968] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.

[1969] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[1970] In R 802In the case of multiple Rs, multiple Rs 802 They are the same or different.

[1971] In R 803 In the case of multiple Rs, multiple Rs 803 (They may be the same or different.)

[1972] As a compound represented by the above general formula (4), the following compounds can be cited as specific examples. In the following specific examples, Ph represents a phenyl group and D represents a deuterium atom.

[1973]

Chemical Formula 103

[1974]

[1975] [Chemical Formula 104]

[1976]

[1977] [Chemical Formula 105]

[1978]

[1979] [Chemical Formula 106]

[1980]

[1981] [Chemical Formula 107]

[1982]

[1983] [Chemical Formula 108]

[1984]

[1985] [Chemical Formula 109]

[1986]

[1987]

Chemical Formula 110

[1988]

[1989]

Chemical Formula 111

[1990]

[1991]

Chemical Formula 112

[1992]

[1993] (The compound represented by general formula (5))

[1994] The compounds represented by general formula (5) will be described. The compounds represented by general formula (5) are the compounds corresponding to the compounds represented by general formula (41-3) above.

[1995]

Chemical Formula 113

[1996]

[1997] (In the above general formula (5),

[1998] By R 501 ~R 507 and R 511 ~R 517 One or more groups consisting of two or more adjacent elements.

[1999] They bond together to form substituted or unsubstituted monocyclic rings.

[2000] They bond together to form substituted or unsubstituted fused rings, or

[2001] They do not bond with each other.

[2002] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 501 ~R 507 and R 511 ~R 517 Each independently

[2003] hydrogen atom,

[2004] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2005] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2006] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2007] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2008] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2009] -O-(R 904 The groups shown in the figure,

[2010] -S-(R 905 The groups shown in the figure,

[2011] -N(R 906 (R) 907 The groups shown in the figure,

[2012] Halogen atoms,

[2013] cyano,

[2014] Nitro,

[2015] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2016] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2017] R 521 and R 522 Each independently

[2018] hydrogen atom,

[2019] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2020] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2021] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2022] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2023] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2024] -O-(R 904 The groups shown in the figure,

[2025] -S-(R 905 The groups shown in the figure,

[2026] -N(R 906 (R) 907 The groups shown in the figure,

[2027] Halogen atoms,

[2028] cyano,

[2029] Nitro,

[2030] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2031] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[2032] "By R" 501 ~R 507 and R 511 ~R 517 "One of the groups consisting of two or more adjacent elements" is, for example, R. 501 With R 502 The group formed, R 502 With R503 The group formed, R 503 With R 504 The group formed, R 505 With R 506 The group formed, R 506 With R 507 The group formed, R 501 With R 502 With R 503 The groups and combinations formed by them.

[2033] In one implementation, R 501 ~R 507 and R 511 ~R 517 At least one, preferably two, of them are -N(R) 906 (R) 907 The group shown is ).

[2034] In one implementation, R 501 ~R 507 and R 511 ~R 517 Each independently

[2035] hydrogen atom,

[2036] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2037] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2038] In one embodiment, the compound represented by the above general formula (5) is the compound represented by the following general formula (52).

[2039]

Chemical Formula 114

[2040]

[2041] (In the above general formula (52),

[2042] By R 531 ~R 534 and R 541 ~R 544 One or more groups consisting of two or more adjacent elements.

[2043] They bond together to form substituted or unsubstituted monocyclic rings.

[2044] They bond together to form substituted or unsubstituted fused rings, or

[2045] They do not bond with each other.

[2046] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 531~R 534 R 541 ~R 544 and R 551 and R 552 Each independently

[2047] hydrogen atom,

[2048] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2049] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2050] R 561 ~R 564 Each independently

[2051] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2052] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[2053] In one embodiment, the compound represented by the above general formula (5) is the compound represented by the following general formula (53).

[2054]

Chemical Formula 115

[2055]

[2056] (In the above general formula (53), R) 551 R 552 and R 561 ~R 564 Each independently relates to R in the above general formula (52) 551 R 552 and R 561 ~R 564 The meaning is the same.

[2057] In one implementation, R in the above general formulas (52) and (53) 561 ~R 564 Each is independently a substituted or unsubstituted aryl group (preferably phenyl) with 6 to 50 carbon atoms in a cyclic structure.

[2058] In one implementation, R in the above general formula (5) 521 and R 522 R in the above general formulas (52) and (53) 551 and R 552 It is a hydrogen atom.

[2059] In one embodiment, the substituents expressed as "substituted or unsubstituted" in the above general formulas (5), (52), and (53) are...

[2060] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2061] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2062] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2063] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2064] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2065] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2066] As a compound represented by the above general formula (5), the following compounds can be cited as specific examples.

[2067]

Chemical Formula 116

[2068]

[2069]

Chemical Formula 117

[2070]

[2071]

Chemical Formula 118

[2072]

[2073]

Chemical Formula 119

[2074]

[2075]

Chemical Formula 120

[2076]

[2077]

Chemical Formula 121

[2078]

[2079]

Chemical Formula 122

[2080]

[2081]

Chemical Formula 123

[2082]

[2083] [Chemical Formula 124]

[2084]

[2085] [Chemical Formula 125]

[2086]

[2087] [Chemical Formula 126]

[2088]

[2089]

Chemical Formula 127

[2090]

[2091] [Chemical Formula 128]

[2092]

[2093] [Chemical Formula 129]

[2094]

[2095]

Chemical Formula 130

[2096]

[2097]

Chemical Formula 131

[2098]

[2099]

Chemical Formula 132

[2100]

[2101] (The compound represented by general formula (6))

[2102] The compounds represented by general formula (6) will be described.

[2103]

Chemical Formula 133

[2104]

[2105] (In the above general formula (6),)

[2106] Rings a, b, and c are each independently...

[2107] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or

[2108] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2109] R 601 and R 602 Each ring independently does not form a substituted or unsubstituted heterocycle, or it bonds with the aforementioned a-ring, b-ring, or c-ring to form a substituted or unsubstituted heterocycle.

[2110] R does not form the aforementioned substituted or unsubstituted heterocycles 601 and R 602 Each independently

[2111] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2112] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2113] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2114] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2115] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2116] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[2117] Rings a, b, and c are rings fused with the central fused 2-ring structure of the above general formula (6) consisting of boron atoms and two nitrogen atoms (substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 cyclic carbon atoms, or substituted or unsubstituted heterocycles with 5 to 50 cyclic atoms).

[2118] The "aromatic hydrocarbon rings" of rings a, b, and c have the same structure as compounds formed by introducing hydrogen atoms into the aforementioned "aryl" group.

[2119] The "aromatic hydrocarbon ring" of ring a contains three carbon atoms on the fused 2-ring structure in the center of the above general formula (6) as cyclic atoms.

[2120] The "aromatic hydrocarbon rings" of rings b and c contain two carbon atoms on the fused 2-ring structure in the center of the above general formula (6) as cyclic atoms.

[2121] As a specific example of "a cyclic aromatic hydrocarbon ring with 6 to 50 carbon atoms, whether substituted or unsubstituted", compounds formed by introducing hydrogen atoms into the "aryl" group described in Specific Example Group G1 can be cited.

[2122] The "heterocyclic" rings a, b, and c have the same structure as compounds formed by introducing hydrogen atoms into the aforementioned "heterocyclic groups".

[2123] The "heterocyclic ring" of ring a includes three carbon atoms in the fused 2-ring structure at the center of the above general formula (6) as cyclic atoms. The "heterocyclic rings" of rings b and c include two carbon atoms in the fused 2-ring structure at the center of the above general formula (6) as cyclic atoms. As a specific example of "heterocyclic rings with 5 to 50 substituted or unsubstituted cyclic atoms", compounds formed by introducing hydrogen atoms into the "heterocyclic group" described in specific example group G2 can be cited.

[2124] R 601 and R 602 Each ring can independently bond with ring a, ring b, or ring c to form substituted or unsubstituted heterocycles. In this case, the heterocycle contains the nitrogen atom in the fused 2-ring structure at the center of the general formula (6). The heterocycle may also contain heteroatoms other than the nitrogen atom. R 601 and R 602 Specifically, bonding with ring a, ring b, or ring c refers to the bonding between atoms constituting ring a, ring b, or ring c and atoms constituting ring R. 601 and R 602 The atoms are bonded together. For example, it could also be R. 601 fused with α ring to form R 601 A nitrogen-containing heterocycle in which two rings (or three or more rings) are fused with the a ring. Specific examples of such nitrogen-containing heterocycles include compounds corresponding to the heterocyclic groups in Specific Example Group G2 that contain nitrogen and are fused with two or more rings.

[2125] R 601 Cases involving b-ring bonding, R 602 The case of α-ring bonding and R 602 The situation regarding bonding with the c-ring is the same as described above.

[2126] In one embodiment, ring a, ring b, and ring c in the above general formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring with 6 to 50 carbon atoms.

[2127] In one embodiment, ring a, ring b, and ring c in the above general formula (6) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.

[2128] In one implementation, R in the above general formula (6) 601 and R 602 Each independently

[2129] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2130] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2131] Preferably, it is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[2132] In one embodiment, the compound represented by the above general formula (6) is the compound represented by the following general formula (62).

[2133]

Chemical Formula 134

[2134]

[2135] (In the above general formula (62),

[2136] R 601A With selection from R 611 and R 621 One or more of them are bonded together to form a substituted or unsubstituted heterocycle, or they do not form a substituted or unsubstituted heterocycle.

[2137] R 602A With selection from R 613 and R 614 One or more of them are bonded together to form a substituted or unsubstituted heterocycle, or they do not form a substituted or unsubstituted heterocycle.

[2138] R does not form the aforementioned substituted or unsubstituted heterocycles 601A and R 602A Each independently

[2139] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2140] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2141] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2142] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2143] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2144] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2145] By R 611 ~R 621 One or more groups consisting of two or more adjacent elements.

[2146] They bond together to form substituted or unsubstituted monocyclic rings.

[2147] They bond together to form substituted or unsubstituted fused rings, or

[2148] They do not bond with each other.

[2149] R does not form the aforementioned substituted or unsubstituted heterocycles, does not form the aforementioned monocyclic rings, and does not form the aforementioned fused rings. 611 ~R 621 Each independently

[2150] hydrogen atom,

[2151] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2152] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2153] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2154] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2155] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2156] -O-(R 904 The groups shown in the figure,

[2157] -S-(R 905 The groups shown in the figure,

[2158] -N(R 906 (R) 907 The groups shown in the figure,

[2159] Halogen atoms,

[2160] cyano,

[2161] Nitro,

[2162] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2163] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[2164] R in the above general formula (62) 601A and R 602A R, respectively, is the same as the general formula (6) above. 601 and R 602 The corresponding functional group.

[2165] For example, R 601A With R 611 These are nitrogen-containing heterocycles that are bonded together to form a fused two-ring (or three-ring or more) fused ring, comprising the rings containing the rings and a benzene ring corresponding to the α-ring. Specific examples of such nitrogen-containing heterocycles include compounds corresponding to the nitrogen-containing fused heterocyclic groups in Specific Example Group G2. R 601A With R 621 Bonding situation, R 602A With R 613 Bonding conditions and R 602A With R 614 The bonding situation is the same as above.

[2166] By R 611 ~R 621 One or more of the two or more adjacent groups can

[2167] They bond together to form substituted or unsubstituted monocyclic rings, or

[2168] They bond together to form substituted or unsubstituted fused rings.

[2169] For example, R 611 With R 612 The bonds can be combined to form structures consisting of six-membered rings such as benzene rings, indole rings, pyrrole rings, benzofuran rings, or benzothiophene rings. The resulting fused rings can be naphthalene rings, carbazole rings, indole rings, dibenzofuran rings, or dibenzothiophene rings.

[2170] In one implementation, R does not participate in forming the ring. 611 ~R 621 Each independently

[2171] hydrogen atom,

[2172] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2173] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2174] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2175] In one implementation, R does not participate in forming the ring. 611 ~R 621 Each independently

[2176] hydrogen atom,

[2177] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2178] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2179] In one implementation, R does not participate in forming the ring. 611 ~R 621 Each independently

[2180] hydrogen atom, or

[2181] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted.

[2182] In one implementation, R does not participate in forming the ring. 611 ~R 621 Each independently

[2183] hydrogen atom, or

[2184] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[2185] R 611 ~R 621At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[2186] In one embodiment, the compound represented by the above general formula (62) is the compound represented by the following general formula (63).

[2187] [Chemical Formula 135]

[2188]

[2189] (In the above general formula (63),

[2190] R 631 With R 646 Bonding to form substituted or unsubstituted heterocycles, or not forming substituted or unsubstituted heterocycles.

[2191] R 633 With R 647 Bonding to form substituted or unsubstituted heterocycles, or not forming substituted or unsubstituted heterocycles.

[2192] R 634 With R 651 Bonding to form substituted or unsubstituted heterocycles, or not forming substituted or unsubstituted heterocycles.

[2193] R 641 With R 642 Bonding to form substituted or unsubstituted heterocycles, or not forming substituted or unsubstituted heterocycles.

[2194] By R 631 ~R 651 One or more groups consisting of two or more adjacent elements.

[2195] They bond together to form substituted or unsubstituted monocyclic rings.

[2196] They bond together to form substituted or unsubstituted fused rings, or

[2197] They do not bond with each other.

[2198] R does not form the aforementioned substituted or unsubstituted heterocycles, does not form the aforementioned monocyclic rings, and does not form the aforementioned fused rings. 631 ~R 651 Each independently

[2199] hydrogen atom,

[2200] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2201] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2202] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2203] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2204] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2205] -O-(R 904 The groups shown in the figure,

[2206] -S-(R 905 The groups shown in the figure,

[2207] -N(R 906 (R) 907 The groups shown in the figure,

[2208] Halogen atoms,

[2209] cyano,

[2210] Nitro,

[2211] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2212] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[2213] R 631 Can be used with R 646 Bonding forms substituted or unsubstituted heterocycles. For example, R can be... 631 With R 646 Bonding to form fused R 646 The bonded benzene ring, or a nitrogen-containing heterocycle consisting of three or more rings fused together with a nitrogen-containing ring and a benzene ring corresponding to the a ring. Specific examples of such nitrogen-containing heterocycles include compounds corresponding to the nitrogen-containing heterocyclic groups fused together in Specific Example Group G2. R 633 With R 647 Bonding situation, R 634 With R 651 Bonding conditions and R 641 With R 642 The bonding situation is the same as above.

[2214] In one implementation, R does not participate in forming the ring. 631 ~R 651 Each independently

[2215] hydrogen atom,

[2216] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2217] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2218] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2219] In one implementation, R does not participate in forming the ring. 631 ~R 651 Each independently

[2220] hydrogen atom,

[2221] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2222] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2223] In one implementation, R does not participate in forming the ring. 631 ~R 651 Each independently

[2224] hydrogen atom, or

[2225] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted.

[2226] In one implementation, R does not participate in forming the ring. 631 ~R 651 Each independently

[2227] hydrogen atom, or

[2228] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[2229] R 631 ~R 651 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[2230] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63A).

[2231]

Chemical Formula 136

[2232]

[2233] (In the above general formula (63A),

[2234] R 661 for

[2235] hydrogen atom,

[2236] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2237] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2238] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2239] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or

[2240] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.

[2241] R 662 ~R 665 Each independently

[2242] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2243] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2244] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2245] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or

[2246] (Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure.)

[2247] In one implementation, R 661 ~R 665 Each independently

[2248] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or

[2249] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.

[2250] In one implementation, R 661 ~R 665 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[2251] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63B).

[2252]

Chemical Formula 137

[2253]

[2254] (In the above general formula (63B),

[2255] R 671 and R 672 Each independently

[2256] hydrogen atom,

[2257] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2258] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2259] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2260] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2261] -N(R 906 (R) 907 The group shown in the figure, or

[2262] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.

[2263] R 673 ~R 675 Each independently

[2264] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2265] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2266] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2267] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2268] -N(R 906 (R) 907 The group shown in the figure, or

[2269] (Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure.)

[2270] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63B').

[2271] [Chemical Formula 138]

[2272]

[2273] (In the above general formula (63B'), R) 672 ~R 675 Each independently relates to R in the above general formula (63B) 672 ~R 675 The meaning is the same.

[2274] In one implementation, R 671 ~R 675 At least one of them is

[2275] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2276] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2277] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2278] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2279] -N(R 906 (R) 907 The group shown in the figure, or

[2280] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.

[2281] In one implementation method

[2282] R 672 for

[2283] hydrogen atom,

[2284] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2285] -N(R 906 (R) 907 The group shown in the figure, or

[2286] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.

[2287] R 671 and R 673 ~R 675 Each independently

[2288] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2289] -N(R 906 (R) 907 The group shown in the figure, or

[2290] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.

[2291] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63C).

[2292]

Chemical Formula 139

[2293]

[2294] (In the above general formula (63C),

[2295] R 681 and R 682 Each independently

[2296] hydrogen atom,

[2297] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2298] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2299] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2300] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or

[2301] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.

[2302] R 683 ~R 686 Each independently

[2303] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2304] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2305] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2306] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or

[2307] (Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure.)

[2308] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63C').

[2309] [Chemical Formula 140]

[2310]

[2311] (In the above general formula (63C'), R) 683 ~R 686 Each independently relates to R in the above general formula (63C). 683 ~R 686 The meaning is the same.

[2312] In one implementation, R 681 ~R 686 Each independently

[2313] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or

[2314] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.

[2315] In one implementation, R 681 ~R 686 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure.

[2316] For the compound shown in the general formula (6) above, the a ring, b ring and c ring can first be connected by a linking group (containing NR).601 Groups and containing NR 602 The intermediate is produced by bonding the boron rings (a, b, and c) with a linking group (a group containing boron atoms). The final product is then produced by bonding the a, b, and c rings together with a linking group (a group containing boron atoms). Amination reactions such as the Buchwald-Hartwig reaction can be used in the first reaction. The tandem hetero Friedel-Crafts reaction can be used in the second reaction.

[2317] The following describes specific examples of compounds represented by the above general formula (6). These are merely examples, and the compounds represented by the above general formula (6) are not limited to the specific examples described below.

[2318]

Chemical Formula 141

[2319]

[2320] [Chemical Formula 142]

[2321]

[2322] [Chemical Formula 143]

[2323]

[2324] [Chemical Formula 144]

[2325]

[2326] [Chemical Formula 145]

[2327]

[2328] [Chemical Formula 146]

[2329]

[2330] [Chemical Formula 147]

[2331]

[2332] [Chemical Formula 148]

[2333]

[2334] [Chemical Formula 149]

[2335]

[2336] [Chemical Formula 150]

[2337]

[2338]

Chemical Formula 151

[2339]

[2340]

Chemical Formula 152

[2341]

[2342]

Chemical Formula 153

[2343]

[2344]

Chemical Formula 154

[2345]

[2346]

Chemical Formula 155

[2347]

[2348] [Chemical Formula 156]

[2349]

[2350] [Chemical Formula 157]

[2351]

[2352] [Chemical Formula 158]

[2353]

[2354] (The compound represented by general formula (7))

[2355] The compounds represented by general formula (7) will be described.

[2356] [Chemical Formula 159]

[2357]

[2358] [Chemical Formula 160]

[2359]

[2360] (In the above general formula (7),

[2361] The r-ring is a ring shown in the above general formula (72) or general formula (73) that is fused at any position of adjacent rings.

[2362] The q-ring and s-ring are each independently rings fused at any position of adjacent rings as shown in the above general formula (74).

[2363] The p-ring and t-ring are each independently structures shown in the above general formula (75) or general formula (76) that are fused at any position of adjacent rings.

[2364] X7 represents an oxygen atom, a sulfur atom, or NR. 702 .

[2365] In R 701 In the case of multiple R, multiple adjacent R 701

[2366] They bond together to form substituted or unsubstituted monocyclic rings.

[2367] They bond together to form substituted or unsubstituted fused rings, or

[2368] They do not bond with each other.

[2369] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 701 and R 702 Each independently

[2370] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2371] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2372] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2373] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2374] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2375] -O-(R 904 The groups shown in the figure,

[2376] -S-(R 905 The groups shown in the figure,

[2377] -N(R 906 (R) 907 The groups shown in the figure,

[2378] Halogen atoms,

[2379] cyano,

[2380] Nitro,

[2381] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2382] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2383] Ar 701 and Ar 702 Each independently

[2384] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2385] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2386] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2387] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2388] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2389] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2390] L 701 for

[2391] Substituted or unsubstituted alkylene groups having 1 to 50 carbon atoms

[2392] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2393] Substituted or unsubstituted ynylene groups with 2 to 50 carbon atoms

[2394] Substituted or unsubstituted cycloalkylene groups with 3 to 50 carbon atoms

[2395] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[2396] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2397] m1 is 0, 1, or 2.

[2398] m2 can be 0, 1, 2, 3, or 4.

[2399] m3 can be independently 0, 1, 2 or 3.

[2400] Each m4 is independently 0, 1, 2, 3, 4, or 5.

[2401] In R 701 In the case of multiple Rs, multiple Rs 701 They are the same or different.

[2402] When multiple X7s exist, they may be identical or different from each other.

[2403] In R 702 In the case of multiple Rs, multiple Rs 702 They are the same or different.

[2404] In Ar 701 In the case of multiple instances, multiple Ar 701 They are the same or different.

[2405] In Ar 702 In the case of multiple instances, multiple Ar 702 They are the same or different.

[2406] In L 701 In the case of multiple Ls, multiple Ls 701 (They may be the same or different.)

[2407] In the above general formula (7), each of the p-ring, q-ring, r-ring, s-ring, and t-ring is fused with its adjacent ring by two carbon atoms. The position and direction of fusion are not limited, and fusion can occur at any position and in any direction.

[2408] In one embodiment, in the above general formula (72) or general formula (73) which is an r-ring, m1 = 0 or m2 = 0.

[2409] In one embodiment, the compound represented by the above general formula (7) is represented by any one of the following general formulas (71-1) to (71-6).

[2410]

Chemical Formula 161

[2411]

[2412]

Chemical Formula 162

[2413]

[2414] [Chemical Formula 163]

[2415]

[2416] [Chemical Formula 164]

[2417]

[2418] [Chemical Formula 165]

[2419]

[2420]

Chemical Formula 166

[2421]

[2422] (In the above general formulas (71-1) to (71-6), R) 701 X7, Ar 701 Ar 702 L 701m1 and m3 are respectively related to R in the above general formula (7). 701 X7, Ar 701 Ar 702 L 701 (m1 and m3 have the same meaning.)

[2423] In one embodiment, the compound represented by the above general formula (7) is represented by any one of the following general formulas (71-11) to (71-13).

[2424] [Chemical Formula 167]

[2425]

[2426] [Chemical Formula 168]

[2427]

[2428] [Chemical Formula 169]

[2429]

[2430] (In the above general formulas (71-11) to (71-13), R) 701 X7, Ar 701 Ar 702 L 701 m1, m3 and m4 are respectively related to R in the above general formula (7) 701 X7, Ar 701 Ar 702 L 701 m1, m3 and m4 have the same meaning.

[2431] In one embodiment, the compound represented by the above general formula (7) is represented by any one of the following general formulas (71-21) to (71-25).

[2432] [Chemical Formula 170]

[2433]

[2434]

Chemical Formula 171

[2435]

[2436] [Chemical Formula 172]

[2437]

[2438]

Chemical Formula 173

[2439]

[2440] [Chemical Formula 174]

[2441]

[2442] (In the above general formulas (71-21) to (71-25), R) 701 X7, Ar 701 Ar 702 L 701 m1 and m4 are respectively related to R in the above general formula (7). 701 X7, Ar 701 Ar 702 L 701 (m1 and m4 have the same meaning.)

[2443] In one embodiment, the compound represented by the above general formula (7) is represented by any one of the following general formulas (71-31) to (71-33).

[2444] [Chemical Formula 175]

[2445]

[2446] [Chemical Formula 176]

[2447]

[2448] [Chemical Formula 177]

[2449]

[2450] (In the above general formulas (71-31) to (71-33), R) 701 X7, Ar 701 Ar 702 L 701 m2 to m4 are respectively related to R in the above general formula (7). 701 X7, Ar 701 Ar 702 L 701 (m2 to m4 have the same meaning.)

[2451] In one implementation, Ar 701 and Ar 702 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure.

[2452] In one implementation, Ar 701 and Ar 702 One of them is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic ring, Ar 701 and Ar 702 The other one is a heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2453] As a compound represented by the above general formula (7), the following compounds can be cited as specific examples.

[2454] [Chemical Formula 178]

[2455]

[2456] [Chemical Formula 179]

[2457]

[2458] [Chemical Formula 180]

[2459]

[2460]

Chemical Formula 181

[2461]

[2462] [Chemical Formula 182]

[2463]

[2464]

Chemical Formula 183

[2465]

[2466] (The compound represented by general formula (8))

[2467] The compounds represented by general formula (8) will be described.

[2468] [Chemical Formula 184]

[2469]

[2470] (In the above general formula (8),

[2471] R 801 With R 802 R 802 With R 803 and R 803 With R 804 At least one group in the group is bonded to each other to form a divalent group as shown in the following general formula (82).

[2472] R 805 With R 806 R 806 With R 807 and R 807 With R 808 At least one group of the radicals bonds together to form a divalent group as shown in the general formula (83).

[2473] [Chemical Formula 185]

[2474]

[2475] (R that does not form the divalent group shown in the above general formula (82)) 801 ~R 804 and R 811 ~R 814 At least one of them is a monovalent group represented by the following general formula (84),

[2476] R that does not form the divalent group shown in the above general formula (83) 805 ~R 808 and R 821 ~R 824 At least one of them is a monovalent group represented by the following general formula (84),

[2477] X8 represents an oxygen atom, a sulfur atom, or NR. 809 ,

[2478] R that does not form the divalent groups shown in general formulas (82) and (83) above and is not the monovalent group shown in general formula (84) above. 801 ~R 808 R that is not a monovalent group as shown in the above general formula (84) 811 ~R 814 and R 821 ~R 824 and R 809 Each independently

[2479] hydrogen atom,

[2480] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2481] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2482] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2483] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2484] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2485] -O-(R 904 The groups shown in the figure,

[2486] -S-(R 905 The groups shown in the figure,

[2487] -N(R 906(R) 907 The groups shown in the figure,

[2488] Halogen atoms,

[2489] cyano,

[2490] Nitro,

[2491] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2492] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[2493] [Chemical Formula 186]

[2494]

[2495] (In the above general formula (84),

[2496] Ar 801 and Ar 802 Each independently

[2497] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2498] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2499] L 801 ~L 803 Each independently

[2500] single bond,

[2501] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms

[2502] Substituted or unsubstituted divalent heterocyclic groups with 5 to 30 cyclic atoms, or

[2503] A divalent linker is formed by bonding 2 to 4 groups from the group consisting of a substituted or unsubstituted aryl group with 6 to 30 carbon atoms and a substituted or unsubstituted divalent heterocyclic group with 5 to 30 carbon atoms.

[2504] In the above general formula (84), * indicates the bonding position with the ring structure shown in general formula (8), or the group shown in general formula (82) or general formula (83).

[2505] In the above general formula (8), the positions of the divalent groups shown in general formula (82) and general formula (83) are not particularly limited, and can be formed in R 801 ~R 808 The group can be formed at any of the possible positions.

[2506] In one embodiment, the compound represented by the above general formula (8) is represented by any one of the following general formulas (81-1) to (81-6).

[2507] [Chemical Formula 187]

[2508]

[2509]

Chemical Formula 188

[2510]

[2511]

Chemical Formula 189

[2512]

[2513] (In the above general formulas (81-1) to (81-6),

[2514] X8 has the same meaning as X8 in the above general formula (8).

[2515] R 801 ~R 824 At least two of them are monovalent groups as shown in the above general formula (84).

[2516] R is not a monovalent group as shown in the above general formula (84) 801 ~R 824 Each independently

[2517] hydrogen atom,

[2518] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2519] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2520] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2521] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2522] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2523] -O-(R 904 The groups shown in the figure,

[2524] -S-(R 905 The groups shown in the figure,

[2525] -N(R 906 (R) 907 The groups shown in the figure,

[2526] Halogen atoms,

[2527] cyano,

[2528] Nitro,

[2529] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2530] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[2531] In one embodiment, the compound represented by the above general formula (8) is represented by any one of the following general formulas (81-7) to (81-18).

[2532] [Chemical Formula 190]

[2533]

[2534]

Chemical Formula 191

[2535]

[2536]

Chemical Formula 192

[2537]

[2538]

Chemical Formula 193

[2539]

[2540] [Chemical Formula 194]

[2541]

[2542] [Chemical Formula 195]

[2543]

[2544] (In the above general formulas (81-7) to (81-18),

[2545] X8 has the same meaning as X8 in the above general formula (8).

[2546] * represents a single bond bonded to the monovalent group shown in the above general formula (84).

[2547] R 801 ~R 824 Each independently relates to the R group in the above general formulas (81-1) to (81-6) that is not the monovalent group shown in the above general formula (84). 801 ~R 824 The meaning is the same.

[2548] R that does not form the divalent groups shown in general formulas (82) and (83) above and is not the monovalent group shown in general formula (84) above. 801 ~R 808 And R groups that are not monovalent groups represented by the above general formula (84) 811 ~R 814 and R 821 ~R 824 Preferred to be independent

[2549] hydrogen atom,

[2550] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2551] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2552] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2553] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2554] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2555] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2556] The monovalent group represented by the above general formula (84) is preferably represented by the following general formula (85) or general formula (86).

[2557] [Chemical Formula 196]

[2558]

[2559] (In the above general formula (85),

[2560] R 831 ~R 840 Each independently

[2561] hydrogen atom,

[2562] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2563] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2564] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2565] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2566] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2567] -O-(R 904 The groups shown in the figure,

[2568] -S-(R 905 The groups shown in the figure,

[2569] -N(R 906 (R) 907 The groups shown in the figure,

[2570] Halogen atoms,

[2571] cyano,

[2572] Nitro,

[2573] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2574] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2575] The asterisk (*) in the above general formula (85) has the same meaning as the asterisk (*) in the above general formula (84).

[2576] [Chemical Formula 197]

[2577]

[2578] (In the above general formula (86),

[2579] Ar 801 L 801 and L 803 Ar in the above general formula (84) 801 L 801 and L 803 Same meaning

[2580] HAr 801 The structure is shown in the following general formula (87).

[2581] [Chemical Formula 198]

[2582]

[2583] (In the above general formula (87),

[2584] X 81 It consists of oxygen or sulfur atoms.

[2585] R 841 ~R 848 Any one of them is related to L 803 Bonded single bonds,

[2586] R is not a single-key letter. 841 ~R 848 Each independently

[2587] hydrogen atom,

[2588] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2589] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2590] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2591] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2592] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2593] -O-(R 904 The groups shown in the figure,

[2594] -S-(R 905 The groups shown in the figure,

[2595] -N(R 906 (R) 907 The groups shown in the figure,

[2596] Halogen atoms,

[2597] cyano,

[2598] Nitro,

[2599] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2600] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[2601] As a compound represented by the above general formula (8), the compounds disclosed in International Publication No. 2014 / 104144 and, for example, the compounds shown below can be cited as specific examples.

[2602]

Chemical Formula 199

[2603]

[2604] [Chemical Formula 200]

[2605]

[2606]

Chemical Formula 201

[2607]

[2608]

Chemical Formula 202

[2609]

[2610]

Chemical Formula 203

[2611]

[2612]

Chemical Formula 204

[2613]

[2614] (The compound represented by general formula (9))

[2615] The compounds represented by general formula (9) will be described.

[2616]

Chemical Formula 205

[2617]

[2618] (In the above general formula (9),

[2619] A 91 Ring and A 92 Each ring is independent of the others.

[2620] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or,

[2621] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2622] Selected from A 91 Ring and A 92 One or more rings in a ring

[2623] * Bonded to the structure shown in the following general formula (92).

[2624]

Chemical Formula 206

[2625]

[2626] (In the above general formula (92),

[2627] A 93 Ring for

[2628] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or,

[2629] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2630] X9 is NR 93 C(R) 94 (R) 95 ), Si(R) 96 (R) 97), Ge(R) 98 (R) 99 ), oxygen atoms, sulfur atoms or selenium atoms,

[2631] R 91 and R 92

[2632] They bond together to form substituted or unsubstituted monocyclic rings.

[2633] They bond together to form substituted or unsubstituted fused rings, or

[2634] They do not bond with each other.

[2635] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 91 and R 92 and R 93 ~R 99 Each independently

[2636] hydrogen atom,

[2637] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2638] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2639] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2640] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2641] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2642] -O-(R 904 The groups shown in the figure,

[2643] -S-(R 905 The groups shown in the figure,

[2644] -N(R 906 (R) 907 The groups shown in the figure,

[2645] Halogen atoms,

[2646] cyano,

[2647] Nitro,

[2648] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2649] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[2650] Selected from A 91 Ring and A 92 One or more rings in the ring are bonded to the structure shown in the above general formula (92). That is, in one embodiment, A 91 The cyclic carbon atom of the aforementioned aromatic hydrocarbon ring or the cyclic atom of the aforementioned heterocycle is bonded to the structure shown in the aforementioned general formula (92). Additionally, in one embodiment, A 92 The cyclic carbon atom of the above-mentioned aromatic hydrocarbon ring or the cyclic atom of the above-mentioned heterocycle is bonded to the structure shown in the above-mentioned general formula (92).

[2651] In one embodiment, the group represented by the following general formula (93) is bonded to A 91 Ring and A 92 One or both of them in the ring.

[2652] [Chemical Formula 207]

[2653]

[2654] (In the above general formula (93),

[2655] Ar 91 and Ar 92 Each independently

[2656] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2657] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2658] L 91 ~L 93 Each independently

[2659] single bond,

[2660] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms

[2661] Substituted or unsubstituted divalent heterocyclic groups with 5 to 30 cyclic atoms, or

[2662] A divalent linking group is formed by bonding 2 to 4 groups from the group consisting of a substituted or unsubstituted aryl group with 6 to 30 carbon atoms and a substituted or unsubstituted divalent heterocyclic group with 5 to 30 carbon atoms.

[2663] In the above general formula (93), * indicates that it is related to A. 91 Ring and A 92 The bonding position of any element in the ring.

[2664] In one implementation, besides A 91 Outside the ring, there is A. 92The cyclic carbon atom of the aforementioned aromatic hydrocarbon ring or the cyclic atom of the aforementioned heterocycle is bonded to the structure shown in the aforementioned general formula (92). In this case, the structures shown in the aforementioned general formula (92) may be the same as or different from each other.

[2665] In one implementation, R 91 and R 92 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure.

[2666] In one implementation, R 91 and R 92 They bond together to form a fluorene structure.

[2667] In one implementation, ring A 91 And Ring A 92 Each is an aromatic hydrocarbon ring, either substituted or unsubstituted, having 6 to 50 carbon atoms, such as a substituted or unsubstituted benzene ring.

[2668] In one implementation, ring A 93 A cyclic aromatic hydrocarbon ring with 6 to 50 carbon atoms, either substituted or unsubstituted, such as a substituted or unsubstituted benzene ring.

[2669] In one implementation, X9 is an oxygen atom or a sulfur atom.

[2670] As a compound represented by the above general formula (9), the following compounds can be cited as specific examples.

[2671] [Chemical Formula 208]

[2672]

[2673]

Chemical Formula 209

[2674]

[2675]

Chemical Formula 210

[2676]

[2677]

Chemical Formula 211

[2678]

[2679] (The compound represented by general formula (10))

[2680] The compounds represented by general formula (10) will be described.

[2681]

Chemical Formula 212

[2682]

[2683]

Chemical Formula 213

[2684]

[2685] (In the above general formula (10),

[2686] Ax1 ring is a ring as shown in the above general formula (10a) that is fused at any position of adjacent rings.

[2687] Ax2 ring is a ring as shown in the above general formula (10b) that is fused at any position between adjacent rings.

[2688] The two asterisks in the above general formula (10b) are bonded to any position of the Ax3 ring.

[2689] X A and X B Each independently is C(R) 1003 (R) 1004 ), Si(R) 1005 (R) 1006 ), oxygen atom or sulfur atom,

[2690] Ax3 ring is

[2691] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or

[2692] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2693] Ar 1001 for

[2694] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2695] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2696] R 1001 ~R 1006 Each independently

[2697] hydrogen atom,

[2698] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2699] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2700] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2701] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2702] -Si(R 901 (R) 902 (R)903 The groups shown in the figure,

[2703] -O-(R 904 The groups shown in the figure,

[2704] -S-(R 905 The groups shown in the figure,

[2705] -N(R 906 (R) 907 The groups shown in the figure,

[2706] Halogen atoms,

[2707] cyano,

[2708] Nitro,

[2709] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2710] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2711] mx1 is 3, mx2 is 2.

[2712] Multiple R 1001 They are the same or different.

[2713] Multiple R 1002 They are the same or different.

[2714] ax is 0, 1, or 2.

[2715] When ax is 0 or 1, the structures within the parentheses shown in "3-ax" may be the same or different from each other.

[2716] When ax = 2, multiple Ar 1001 (They may be the same or different.)

[2717] In one implementation, Ar 1001 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[2718] In one embodiment, the Ax3 ring is a substituted or unsubstituted aromatic hydrocarbon ring with 6 to 50 carbon atoms, such as a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring.

[2719] In one implementation, R 1003 and R 1004 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[2720] In one implementation, ax is 1.

[2721] As a compound represented by the above general formula (10), the following compounds can be cited as specific examples.

[2722]

Chemical Formula 214

[2723]

[2724] In one embodiment, the light-emitting layer 5 contains a light-emitting compound selected from [a specific compound].

[2725] The compounds represented by the above general formula (4),

[2726] The compounds represented by the above general formula (5),

[2727] The compounds represented by the above general formula (6), and

[2728] One or more of the compounds represented by the following general formula (63a).

[2729]

Chemical Formula 215

[2730]

[2731] (In the above general formula (63a),

[2732] R 631 With R 646 They may bond to form substituted or unsubstituted heterocycles, or they may not form substituted or unsubstituted heterocycles.

[2733] R 633 With R 647 They may bond to form substituted or unsubstituted heterocycles, or they may not form substituted or unsubstituted heterocycles.

[2734] R 634 With R 651 They may bond to form substituted or unsubstituted heterocycles, or they may not form substituted or unsubstituted heterocycles.

[2735] R 641 With R 642 They may bond to form substituted or unsubstituted heterocycles, or they may not form substituted or unsubstituted heterocycles.

[2736] R 631 ~R 651 Two or more adjacent groups

[2737] They bond together to form substituted or unsubstituted monocyclic rings.

[2738] They bond together to form substituted or unsubstituted fused rings, or

[2739] They do not bond with each other.

[2740] R does not form the aforementioned substituted or unsubstituted heterocycles, does not form the aforementioned monocyclic rings, and does not form the aforementioned fused rings. 631 ~R 651 Each independently

[2741] hydrogen atom,

[2742] Halogen atoms,

[2743] cyano,

[2744] Nitro,

[2745] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2746] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2747] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2748] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2749] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2750] -O-(R 904 The groups shown in the figure,

[2751] -S-(R 905 The groups shown in the figure,

[2752] -N(R 906 (R) 907 The groups shown in the figure,

[2753] A substituted or unsubstituted aryl group with 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 cyclic atoms.

[2754] Among them, R does not form the aforementioned substituted or unsubstituted heterocycles, does not form the aforementioned monocyclic rings, and does not form the aforementioned fused rings. 631 ~R 651 At least one of them is

[2755] Halogen atoms,

[2756] cyano,

[2757] Nitro,

[2758] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2759] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2760] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2761] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2762] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2763] -O-(R 904 The groups shown in the figure,

[2764] -S-(R 905 The groups shown in the figure,

[2765] -N(R 906 (R) 907 The groups shown in the figure,

[2766] Halogen atoms,

[2767] cyano,

[2768] Nitro,

[2769] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2770] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[2771] In one embodiment, the compound represented by the above general formula (4) is a compound represented by the above general formula (41-3), general formula (41-4) or general formula (41-5), wherein the A1 ring in the above general formula (41-5) is a fused aromatic hydrocarbon ring with 10 to 50 cyclic carbon atoms, substituted or unsubstituted, or a fused heterocycle with 8 to 50 cyclic atoms, substituted or unsubstituted.

[2772] In one embodiment, the substituted or unsubstituted fused aromatic hydrocarbon rings with 10 to 50 carbon atoms in the above general formulas (41-3), (41-4), and (41-5) are...

[2773] Substituted or unsubstituted naphthalene ring,

[2774] Substituted or unsubstituted anthracene rings, or

[2775] Substituted or unsubstituted fluorene ring,

[2776] The above-mentioned fused heterocycles with 8 to 50 cyclic atoms, whether substituted or unsubstituted, are

[2777] Substituted or unsubstituted dibenzofuran rings,

[2778] Substituted or unsubstituted carbazole ring, or

[2779] Substituted or unsubstituted dibenzothiophene ring.

[2780] In one embodiment, the substituted or unsubstituted fused aromatic hydrocarbon ring with 10 to 50 carbon atoms in the above general formulas (41-3), (41-4), or (41-5) is...

[2781] Substituted or unsubstituted naphthalene ring, or

[2782] Substituted or unsubstituted fluorene ring,

[2783] The above-mentioned fused heterocycles with 8 to 50 cyclic atoms, whether substituted or unsubstituted, are

[2784] Substituted or unsubstituted dibenzofuran rings,

[2785] Substituted or unsubstituted carbazole ring, or

[2786] Substituted or unsubstituted dibenzothiophene ring.

[2787] In one embodiment, the compound represented by the above general formula (4) is selected from...

[2788] The compounds represented by the following general formula (461),

[2789] The compounds represented by the following general formula (462),

[2790] The compounds represented by the following general formula (463),

[2791] The compounds represented by the following general formula (464),

[2792] The compounds represented by the following general formula (465),

[2793] The compounds represented by the following general formula (466), and

[2794] The group consisting of compounds represented by the following general formula (467).

[2795]

Chemical Formula 216

[2796]

[2797]

Chemical Formula 217

[2798]

[2799]

Chemical Formula 218

[2800]

[2801]

Chemical Formula 219

[2802]

[2803]

Chemical Formula 220

[2804]

[2805] (In the above general formulas (461) to (467),

[2806] By R 421 ~R 427 R 431 ~R 436 R 440 ~R 448 and R 451 ~R 454 One or more groups consisting of two or more adjacent elements.

[2807] They bond together to form substituted or unsubstituted monocyclic rings.

[2808] They bond together to form substituted or unsubstituted fused rings, or

[2809] They do not bond with each other.

[2810] R 437 R 438 and R that does not form the aforementioned single ring and does not form the aforementioned fused ring. 421 ~R 427 R 431 ~R 436 R 440 ~R 448 and R 451 ~R 454 Each independently

[2811] hydrogen atom,

[2812] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2813] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2814] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2815] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2816] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2817] -O-(R 904 The groups shown in the figure,

[2818] -S-(R 905 The groups shown in the figure,

[2819] -N(R906 (R) 907 The groups shown in the figure,

[2820] Halogen atoms,

[2821] cyano,

[2822] Nitro,

[2823] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2824] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2825] X4 represents an oxygen atom, NR 801 Or C(R) 802 (R) 803 ),

[2826] R 801 R 802 and R 803 Each independently

[2827] hydrogen atom,

[2828] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2829] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2830] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2831] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2832] Preferably, it is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[2833] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.

[2834] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[2835] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.

[2836] In R 803 In the case of multiple Rs, multiple Rs 803 (They may be the same or different.)

[2837] In one implementation, R 421 ~R 427 and R 440 ~R448 Each independently

[2838] hydrogen atom,

[2839] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2840] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2841] In one implementation, R 421 ~R 427 and R 440 ~R 447 Each independently chooses freedom

[2842] hydrogen atom,

[2843] Substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, and

[2844] The group consisting of substituted or unsubstituted heterocyclic groups with 5 to 18 cyclic atoms.

[2845] In one embodiment, the compound represented by the above general formula (41-3) is the compound represented by the following general formula (41-3-1).

[2846]

Chemical Formula 221

[2847]

[2848] (In the above general formula (41-3-1), R) 423 R 425 R 426 R 442 R 444 and R 445 Each independently relates to R in the above general formula (41-3). 423 R 425 R 426 R 442 R 444 and R 445 The meaning is the same.

[2849] In one embodiment, the compound represented by the above general formula (41-3) is the compound represented by the following general formula (41-3-2).

[2850]

Chemical Formula 222

[2851]

[2852] (In the above general formula (41-3-2), R) 421 ~R 427 and R 440 ~R 448Each independently relates to R in the above general formula (41-3). 421 ~R 427 and R 440 ~R 448 Same meaning

[2853] Among them, R 421 ~R 427 and R 440 ~R 446 At least one of them is -N(R) 906 (R) 907 The group shown in the diagram.

[2854] In one embodiment, R in the above general formula (41-3-2) 421 ~R 427 and R 440 ~R 446 Any two of them are -N(R) 906 (R) 907 The group shown is ).

[2855] In one embodiment, the compound represented by the above general formula (41-3-2) is the compound represented by the following formula (41-3-3).

[2856]

Chemical Formula 223

[2857]

[2858] (In the above general formula (41-3-3), R) 421 ~R 424 R 440 ~R 443 R 447 and R 448 Each independently relates to R in the above general formula (41-3). 421 ~R 424 R 440 ~R 443 R 447 and R 448 Same meaning

[2859] R A R B R C and R D Each independently

[2860] Substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, or

[2861] (Substituted or unsubstituted heterocyclic groups with 5 to 18 cyclic atoms)

[2862] In one embodiment, the compound represented by the above general formula (41-3-3) is the compound represented by the following formula (41-3-4).

[2863] [Chemical Formula 224]

[2864]

[2865] (In the above general formula (41-3-4), R) 447 R 448 R A R B R C and R D Each independently relates to R in the above general formula (41-3-3) 447 R 448 R A R B R C and R D The meaning is the same.

[2866] In one implementation, R A R B R C and R D Each is an aryl group, either substituted or unsubstituted, with 6 to 18 carbon atoms in a cyclic structure.

[2867] In one implementation, R A R B R C and R D Each can be a substituted or unsubstituted phenyl group.

[2868] In one implementation, R 447 and R 448 It is a hydrogen atom.

[2869] In the organic EL element 1A, the luminescent compound contained in the light-emitting layer 5 is preferably a compound that exhibits luminescence with a maximum peak wavelength of 500 nm or less, and more preferably a compound that exhibits luminescence with a wavelength of 430 nm or more and 480 nm or less.

[2870] In the organic EL element 1A, the luminescent compound contained in the light-emitting layer 5 is preferably a compound that exhibits fluorescence emission with a maximum peak wavelength of 500 nm or less, and more preferably a compound that exhibits fluorescence emission with a wavelength of 430 nm or more and 480 nm or less.

[2871] In the organic EL element 1A, when the light-emitting layer 5 contains the compound involved in the first embodiment and the luminescent compound, the compound involved in the first embodiment is preferably a host material (sometimes also called a matrix material), and the luminescent compound is preferably a dopant material (sometimes also called a guest material, emitter, or luminescent material).

[2872] In the organic EL element 1A, when the light-emitting layer 5 contains the compound and the luminescent compound according to the second embodiment, the compound according to the second embodiment is preferably a host material (sometimes also called a matrix material), and the luminescent compound is preferably a dopant material (sometimes also called a guest material, emitter, or luminescent material).

[2873] In the organic EL element 1A, when the light-emitting layer 5 contains the compound involved in the third embodiment and the luminescent compound, the compound involved in the third embodiment is preferably a host material (sometimes also called a matrix material), and the luminescent compound is preferably a dopant material (sometimes also called a guest material, emitter, or luminescent material).

[2874] In this specification, "main material" refers to, for example, a material with a content of "50% by mass or more of the layer".

[2875] Therefore, for example, in the case of organic EL element 1A, the content of the compound represented by the above general formula (1A) in the light-emitting layer 5 is 50% by mass or more of the total mass of the light-emitting layer.

[2876] Therefore, for example, in the case of organic EL element 1A, the content of the compound represented by the above general formula (1C) in the light-emitting layer 5 is 50% by mass or more of the total mass of the light-emitting layer.

[2877] (Thickness of the light-emitting layer)

[2878] The thickness of the light-emitting layer 5 is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and even more preferably 10 nm or more and 50 nm or less. If the thickness of the light-emitting layer is 5 nm or more, it is easy to form the light-emitting layer and easy to adjust the color. If the thickness of the light-emitting layer is 50 nm or less, it is easy to suppress the rise of the driving voltage.

[2879] (The content of compounds in the luminescent layer)

[2880] When the light-emitting layer 5 contains the compound and the luminescent compound involved in the first embodiment, the content of the compound and the luminescent compound involved in the first embodiment in the light-emitting layer 5 is preferably within the following ranges, for example.

[2881] The content of the compound involved in the first embodiment is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less.

[2882] The content of the luminescent compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less.

[2883] The upper limit of the total content of the compound and the luminescent compound involved in the first embodiment in the light-emitting layer 5 is 100% by mass.

[2884] When the light-emitting layer 5 contains the compound and luminescent compound according to the second embodiment, the content of the compound and luminescent compound according to the second embodiment in the light-emitting layer 5 is preferably within the following ranges, for example.

[2885] The content of the compound involved in the second embodiment is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less.

[2886] The content of the luminescent compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less.

[2887] The upper limit of the total content of the compound and the luminescent compound involved in the second embodiment of the light-emitting layer 5 is 100% by mass.

[2888] When the light-emitting layer 5 contains the compound and the luminescent compound according to the third embodiment, the content of the compound and the luminescent compound according to the third embodiment in the light-emitting layer 5 is preferably within the following ranges, for example.

[2889] The content of the compound involved in the third embodiment is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less.

[2890] The content of the luminescent compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less.

[2891] The upper limit of the total content of the compound and the luminescent compound involved in the third embodiment of the light-emitting layer 5 is 100% by mass.

[2892] It should be noted that this embodiment does not exclude the inclusion of materials other than the compounds and luminescent compounds involved in the first embodiment in the light-emitting layer 5.

[2893] In the light-emitting layer 5, the compound involved in the first embodiment may contain only one type or more types. In the light-emitting layer 5, the luminescent compound may contain only one type or more types.

[2894] Furthermore, this embodiment does not exclude the inclusion of materials other than the compounds and luminescent compounds involved in the second embodiment in the light-emitting layer 5.

[2895] In the light-emitting layer 5, the compound involved in the second embodiment may contain only one type or more types. In the light-emitting layer 5, the luminescent compound may contain only one type or more types.

[2896] Furthermore, this embodiment does not exclude the inclusion of materials other than the compounds and luminescent compounds involved in the third embodiment in the light-emitting layer 5.

[2897] In the light-emitting layer 5, the compound involved in the third embodiment may contain only one type or more types. In the light-emitting layer 5, the luminescent compound may contain only one type or more types.

[2898] Figure 2 The diagram shows the general configuration of another example of the organic EL element involved in this embodiment.

[2899] Figure 2 The organic EL element 1B shown differs from the organic EL element 1A at the point in the organic layer 10B that contains the first light-emitting region 5B, but is the same as the organic EL element 1A at other points. The first light-emitting region 5B sequentially includes a first light-emitting layer 51 and a second light-emitting layer 52 from the anode 3 side.

[2900] The first luminescent layer 51 contains a first compound, and the second luminescent layer 52 contains a second compound. The first compound and the second compound are different compounds from each other.

[2901] (First compound)

[2902] In one embodiment of the organic EL element 1B, the first compound is the compound involved in the first embodiment.

[2903] In one embodiment of the organic EL element, the first compound may be a compound represented by the general formula (1C-A) above.

[2904] In one embodiment of the organic EL element 1B, the first compound is the compound involved in the second embodiment.

[2905] In one embodiment of the organic EL element, the first compound may be a compound represented by the general formula (1C-B) above.

[2906] In one embodiment of the organic EL element 1B, the first compound is the compound involved in the third embodiment.

[2907] In one embodiment of the organic EL element, the first compound may be a compound represented by the general formula (1C-C) above.

[2908] In one embodiment of the organic EL element 1B, the first compound is the compound represented by the above general formula (1C).

[2909] (Second compound)

[2910] In the organic EL element 1B, the second compound is preferably a compound represented by the following general formula (2).

[2911] [Chemical Formula 225]

[2912]

[2913] (In the above general formula (2),)

[2914] R 201 ~R 208 Each independently

[2915] hydrogen atom,

[2916] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2917] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[2918] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2919] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2920] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2921] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2922] -O-(R 904 The groups shown in the figure,

[2923] -S-(R 905 The groups shown in the figure,

[2924] -N(R 906 (R) 907The groups shown in the figure,

[2925] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[2926] -C(=O)R 801 The groups shown

[2927] -COOR 802 The groups shown

[2928] Halogen atoms,

[2929] cyano,

[2930] Nitro,

[2931] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2932] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2933] L 201 and L 202 Each independently

[2934] single bond,

[2935] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[2936] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2937] Ar 201 and Ar 202 Each independently

[2938] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2939] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[2940] (In the second compound involved in this embodiment, R) 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently

[2941] hydrogen atom,

[2942] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2943] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2944] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2945] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2946] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.

[2947] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.

[2948] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.

[2949] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.

[2950] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.

[2951] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.

[2952] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.

[2953] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[2954] In R 802 In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)

[2955] In the organic EL element involved in this embodiment, it is preferred that,

[2956] R 201 ~R 208 Each independently

[2957] hydrogen atom,

[2958] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2959] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[2960] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2961] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2962] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2963] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2964] -O-(R 904 The groups shown in the figure,

[2965] -S-(R 905 The groups shown in the figure,

[2966] -N(R 906 (R) 907 The groups shown in the figure,

[2967] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[2968] -C(=O)R 801 The groups shown

[2969] -COOR 802 The groups shown

[2970] Halogen atoms,

[2971] cyano, or

[2972] Nitro,

[2973] L 201 and L 202 Each independently

[2974] single bond,

[2975] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[2976] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2977] Ar 201 and Ar 202 Each independently

[2978] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2979] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2980] In the organic EL element involved in this embodiment, it is preferred that,

[2981] L 201 and L 202 Each independently

[2982] single key, or

[2983] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms in a cyclic structure.

[2984] Ar 201 and Ar 202 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure.

[2985] In the organic EL element involved in this embodiment, it is preferred that,

[2986] Ar 201 and Ar 202 Each independently

[2987] Phenyl,

[2988] Naphthyl,

[2989] Fiki,

[2990] Biphenyl

[2991] Triphenyl

[2992] Diphenylfluorenyl,

[2993] Dimethylfluorenyl,

[2994] benzodiphenylfluorenyl,

[2995] benzodimethylfluorenyl,

[2996] Dibenzofuranyl,

[2997] Dibenzothiophene group,

[2998] Naphthobenzofuranyl, or

[2999] Naphthobenzothiophene group.

[3000] In the organic EL element of this embodiment, the second compound represented by the above general formula (2) is preferably a compound represented by the following general formulas (201), (202), (203), (204), (205), (206), (207), (208), or (209).

[3001]

Chemical Formula 226

[3002]

[3003] [Chemical Formula 227]

[3004]

[3005] [Chemical Formula 228]

[3006]

[3007] [Chemical Formula 229]

[3008]

[3009]

Chemical Formula 230

[3010]

[3011]

Chemical Formula 231

[3012]

[3013]

Chemical Formula 232

[3014]

[3015]

Chemical Formula 233

[3016]

[3017] [Chemical Formula 234]

[3018]

[3019] (In the above general formulas (201) to (209),

[3020] L 201 and Ar 201 L in the above general formula (2) 201 and Ar 201 Same meaning

[3021] R 201 ~R 208 Each independently relates to R in the above general formula (2) 201 ~R 208 The meaning is the same.

[3022] The second compound represented by the above general formula (2) is also preferably a compound represented by the following general formulas (221), (222), (223), (224), (225), (226), (227), (228) or (229).

[3023] [Chemical Formula 235]

[3024]

[3025]

Chemical Formula 236

[3026]

[3027] [Chemical Formula 237]

[3028]

[3029] [Chemical Formula 238]

[3030]

[3031] [Chemical Formula 239]

[3032]

[3033] [Chemical Formula 240]

[3034]

[3035]

Chemical Formula 241

[3036]

[3037]

Chemical Formula 242

[3038]

[3039] [Chemical Formula 243]

[3040]

[3041] (In the above general formulas (221), (222), (223), (224), (225), (226), (227), (228), and (229),

[3042] R 201 and R 203 ~R 208 Each independently relates to R in the above general formula (2) 201 and R 203 ~R 208 Same meaning

[3043] L 201 and Ar 201 Each of them corresponds to L in the above general formula (2) 201 and Ar 201 Same meaning

[3044] L 203 L in the above general formula (2) 201 Same meaning

[3045] L 203 With L 201 They are the same or different.

[3046] Ar 203 Ar in the above general formula (2) 201 Same meaning

[3047] Ar 203 with Ar 201 (They may be the same or different.)

[3048] The second compound represented by the above general formula (2) is also preferably a compound represented by the following general formulas (241), (242), (243), (244), (245), (246), (247), (248) or (249).

[3049] [Chemical Formula 244]

[3050]

[3051] [Chemical Formula 245]

[3052]

[3053] [Chemical Formula 246]

[3054]

[3055] [Chemical Formula 247]

[3056]

[3057] [Chemical Formula 248]

[3058]

[3059] [Chemical Formula 249]

[3060]

[3061] [Chemical Formula 250]

[3062]

[3063]

Chemical Formula 251

[3064]

[3065]

Chemical Formula 252

[3066]

[3067] (In the above general formulas (241), (242), (243), (244), (245), (246), (247), (248), and (249),

[3068] R 201 R 202 and R 204 ~R 208 Each independently relates to R in the above general formula (2) 201 R 202 and R 204 ~R 208 Same meaning

[3069] L 201 and Ar 201 Each of them corresponds to L in the above general formula (2) 201 and Ar 201 Same meaning

[3070] L 203 L in the above general formula (2) 201 Same meaning

[3071] L 203 With L 201 They are the same or different.

[3072] Ar 203 Ar in the above general formula (2) 201 Same meaning

[3073] Ar 203 with Ar 201 (They may be the same or different.)

[3074] In the second compound represented by the above general formula (2), R is preferred. 201 ~R 208 Each independently

[3075] hydrogen atom,

[3076] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[3077] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or

[3078] -Si(R 901 (R) 902 (R) 903 The group shown is ).

[3079] Preferably, L 201 for

[3080] single key, or

[3081] Unsubstituted arylene groups with 6 to 22 carbon atoms in the cyclic group,

[3082] Ar 201 It is an aryl group with 6 to 22 carbon atoms, either substituted or unsubstituted.

[3083] In the organic EL element involved in this embodiment,

[3084] In the second compound represented by the above general formula (2), R is preferred. 201 ~R 208 Each independently

[3085] hydrogen atom,

[3086] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[3087] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or

[3088] -Si(R 901 (R) 902 (R) 903 The group shown is ).

[3089] In the organic EL element involved in this embodiment,

[3090] In the second compound represented by the above general formula (2), R 201 ~R 208 Hydrogen atoms are preferred.

[3091] In the second compound described above, the groups described as "substituted or unsubstituted" are preferably "unsubstituted".

[3092] In the organic EL element involved in this embodiment, for example, Ar in the second compound shown in the above general formula (2) 201 It is a substituted or unsubstituted dibenzofuranyl group.

[3093] In the organic EL element involved in this embodiment, for example, Ar in the second compound shown in the above general formula (2) 201 It is an unsubstituted dibenzofuranyl group.

[3094] In the organic EL element involved in this embodiment, for example, the second compound shown in the above general formula (2) contains at least one hydrogen, at least one of which is deuterium.

[3095] In the organic EL element involved in this embodiment, for example, L in the second compound shown in the above general formula (2) 201 The range is from TEMP-63 to TEMP-68.

[3096] [Chemical Formula 253]

[3097]

[3098] In the organic EL device according to the present embodiment, for example, Ar in the second compound represented by the above general formula (2) 201 is at least one group selected from the group consisting of substituted or unsubstituted anthryl,

[3099] benzanthryl,

[3100] phenanthryl,

[3101] triphenylenyl,[Wait no, correction: benzophenanthryl,[

[3102] phenalenyl,

[3103] pyrenyl,[

[3104] chrysenyl,[

[3105] benzochrysenyl,[

[3106] triphenylenyl,[

[3107] benzotriphenylenyl,[

[3108] naphthacenyl,[

[3109] pentacenyl,[

[3110] fluoranthenyl,[

[3111] benzofluoranthenyl, and

[3112] perylenyl.

[3113] In the organic EL device according to the present embodiment, for example, Ar in the second compound represented by the above general formula (2) 201 is a substituted or unsubstituted fluorenyl group.

[3114] In the organic EL device according to the present embodiment, for example, Ar in the second compound represented by the above general formula (2) 201 is a substituted or unsubstituted xanthenyl group.

[3115] In the organic EL device according to the present embodiment, for example, Ar in the second compound represented by the above general formula (2) 201 is a benzoxanthenyl group.

[3116] (Method for Producing Second Compound)

[3117] The second compound can be produced by a known method. Alternatively, the second compound can also be produced by imitating known methods, using known starting materials and alternative reactions corresponding to the target substance.

[3118] (Specific example of the second compound)

[3119] Specific examples of the second compound include the following compounds. However, the present invention is not limited to these specific examples of the second compound.

[3120] [Chemical Formula 254]

[3121]

[3122] [Chemical Formula 255]

[3123]

[3124] [Chemical Formula 256]

[3125]

[3126] [Chemical Formula 257]

[3127]

[3128] [Chemical Formula 258]

[3129]

[3130] [Chemical Formula 259]

[3131]

[3132] [Chemical Formula 260]

[3133]

[3134]

Chemical Formula 261

[3135]

[3136]

Chemical Formula 262

[3137]

[3138] [Chemical Formula 263]

[3139]

[3140] [Chemical Formula 264]

[3141]

[3142] [Chemical Formula 265]

[3143]

[3144]

Chemical Formula 266

[3145]

[3146] [Chemical Formula 267]

[3147]

[3148] [Chemical Formula 268]

[3149]

[3150] [Chemical Formula 269]

[3151]

[3152] [Chemical Formula 270]

[3153]

[3154]

Chemical Formula 271

[3155]

[3156]

Chemical Formula 272

[3157]

[3158] [Chemical ...

Claims

1. The compounds represented by the following general formula (1C-B), In the general formula (1C-B), R 11 The group represented by the general formula (1D-B), or R 12 The group represented by the general formula (1D-B) R1~R3, R4~R6, R7, R8, R9 and R 10 Each independently protium atom, Deuterium atom, or Unsubstituted phenyl, In R 11 In the case of a group represented by the general formula (1D-B), R 12 It can be a protium atom, a deuterium atom, or an unsubstituted phenyl group. In R 12 In the case of a group represented by the general formula (1D-B), R 11 It is an unsubstituted phenyl group. In the general formula (1D-B), R 21 ~R 30 One of them represents the bonding position with the benzo[a]anthracene ring in the general formula (1C-B), and the R in the general formula (1D-B) is not at that bonding position. 21 ~R 30 In a group consisting of two or more adjacent groups, one or more groups are not bonded to each other. The R in general formula (1D-B) is not bonded to the benzo[a]anthracene ring in general formula (1C-B). 21 ~R 30 Each independently protium atom, Deuterium atom, or Unsubstituted phenyl group.

2. The compound according to claim 1, wherein, The group represented by the general formula (1D-B) is a group represented by the following general formulas (1D-B1), (1D-B2), or (1D-B3). In the general formula (1D-B1), By R 21 ~R 29 In a group consisting of two or more adjacent groups, one or more groups are not bonded to each other. R 21 ~R 29 Each independently protium atom, Deuterium atom, or Unsubstituted phenyl, * indicates the bonding position with the benzo[a]anthracene ring in the general formula (1C-B). In the general formula (1D-B2), By R 21 ~R 28 and R 30 In a group consisting of two or more adjacent groups, one or more groups are not bonded to each other. R 21 ~R 28 and R 30 Each independently relates to R in the general formula (1D-B1) 21 ~R 29 Same meaning * indicates the bonding position with the benzo[a]anthracene ring in the general formula (1C-B). In the general formula (1D-B3), By R 21 ~R 27 R 29 and R 30 In a group consisting of two or more adjacent groups, one or more groups are not bonded to each other. R 21 ~R 27 R 29 and R 30 Each independently relates to R in the general formula (1D-B1) 21 ~R 29 Same meaning * indicates the bonding position with the benzo[a]anthracene ring in the general formula (1C-B).

3. The compound according to claim 2, wherein, The group represented by the general formula (1D-B) is the same group represented by the general formula (1D-B1).

4. The compound according to claim 1, wherein, R 11 The group is represented by the general formula (1D-B).

5. The compound according to claim 1, wherein, R 12 The group is represented by the general formula (1D-B).

6. The compound according to claim 1, wherein, R 11 For the group represented by the general formula (1D-B), R 12 It is an unsubstituted phenyl group.

7. The compound according to any one of claims 1 to 4, wherein, R7 and R 12 It consists of protium or deuterium atoms.

8. The compound according to any one of claims 1 to 6, wherein, It has more than one deuterium atom in the molecule.

9. An organic electroluminescent element comprising any one of claims 1 to 6.

10. The organic electroluminescent element according to claim 9, wherein it has anode, cathode, and An organic layer disposed between the anode and the cathode, The organic layer has a light-emitting region. The light-emitting region includes at least one light-emitting layer. The light-emitting layer contains the compound.

11. The organic electroluminescent element according to claim 10, wherein, The light-emitting region includes a first light-emitting layer and a second light-emitting layer. The first light-emitting layer contains the aforementioned compound as a first compound, and the second light-emitting layer contains a second compound. The triplet energy T1(H1) of the first compound and the triplet energy T1(H2) of the second compound satisfy the following mathematical expression (Mathematical Expression 1). T1(H1)>T1(H2) …(Mathematical Formula 1).

12. An electronic device wherein the organic electroluminescent element of claim 9 is incorporated.

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