Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device

Abstract

To provide a compound further improving the performance of an organic EL element, an organic electroluminescent element whose element performance is further improved, an electronic device including such an organic electroluminescent element, a compound represented by the following formula (1) having at least one deuterium atom, an organic electroluminescent element including the compound, and an electronic device including such an organic electroluminescent element are provided. Each symbol in the formula is defined in the description.

Description

Technical Field

[0001] This invention relates to compounds, materials for organic electroluminescent elements, organic electroluminescent elements, and electronic devices comprising the organic electroluminescent elements. Background Technology

[0002] Generally, organic electroluminescent devices (hereinafter sometimes referred to as "organic EL devices") consist of an anode, a cathode, and an organic layer sandwiched between the anode and cathode. When a voltage is applied between the two electrodes, electrons are injected into the luminescent region from the cathode side, and holes are injected into the luminescent region from the anode side. The injected electrons and holes recombine in the luminescent region to generate an excited state, which emits light when it returns to the ground state. Therefore, developing materials that efficiently transport electrons or holes to the luminescent region and facilitate electron-hole recombination is important for obtaining high-performance organic EL devices.

[0003] Patent documents 1 and 2 disclose compounds used as materials for organic electroluminescent elements.

[0004] Existing technical documents

[0005] Patent documents

[0006] Patent Document 1: International Publication No. 2022 / 071350

[0007] Patent Document 2: International Publication No. 2017 / 052261 Summary of the Invention

[0008] The problem the invention aims to solve

[0009] In the past, a large number of compounds for organic EL devices have been reported, but we are still looking for compounds that can further improve the performance of organic EL devices.

[0010] The present invention was made to solve the above-mentioned problems, and aims to provide a compound that further improves the performance of an organic EL element, an organic EL element that further improves the performance of the element, and an electronic device comprising such an organic EL element.

[0011] means for solving problems

[0012] The inventors have repeatedly conducted in-depth studies on the performance of organic EL elements containing the compounds described in Patent Documents 1 to 2, and found that the performance of organic EL elements containing the compounds shown in Formula (1) is further improved.

[0013] In one embodiment, the present invention provides a compound having at least one deuterium atom as shown in formula (1) below.

[0014]

Chemical Formula 1

[0015]

[0016] In equation (1),

[0017] N ＊ The central nitrogen atom,

[0018] R 1 ~R 4 and R 11 ~R 18 Each is an independent hydrogen atom.

[0019] Ar 1 It is an aryl group with 6 to 50 carbon atoms that is substituted or unsubstituted, or a heterocyclic group with 5 to 50 carbon atoms that is substituted or unsubstituted.

[0020] In the case of substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, the substituents described as "substituted or unsubstituted" are each independently a halogen, an unsubstituted alkyl group with 1 to 18 carbon atoms, an unsubstituted cycloalkyl group with 3 to 20 carbon atoms, or an unsubstituted aryl group with 6 to 18 carbon atoms, wherein the hydrogen atoms of the unsubstituted alkyl group are not deuterated.

[0021] When a heterocyclic group with 5 to 50 cyclic atoms is described as "substituted or unsubstituted", the substituent is independently a halogen, an unsubstituted alkyl group with 1 to 18 carbon atoms, or an unsubstituted cycloalkyl group with 3 to 20 cyclic carbon atoms.

[0022] Ar 2 It is represented by the following formulas (2A), (2B), (2C), (2D), (2E), (2F) or (2G).

[0023]

Chemical Formula 2

[0024]

[0025] (In equation (2A),

[0026] *21 indicates the relationship with L 2 . bond.

[0027] Selected from R 101 ~R 105 One of them is a single bond bonded to *22, selected from R 106 ~R 110 One of them is a single bond that bonds with *23.

[0028] R is not the single bond mentioned above. 101 ~R 105 and R 106 ~R 110Each is independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.

[0029] Selected from R that is not one of the above single bonds 101 ~R 105 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0030] Selected from R that is not one of the above single bonds 106 ~R 110 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0031] R 111 ~R 115 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 5 to 13 carbon atoms.

[0032] Selected from R 111 ~R 115 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0033] j is 0, 1, or 2, and k is 0 or 1. The case where j is 2 and k is 0 is excluded.

[0034] When j=0 and k=0, *23 means *21.

[0035] When j=0 and k=1, *22 means *21.

[0036] When j=1 and k=0, *23 represents *22.

[0037]

Chemical Formula 3

[0038]

[0039] (In equation (2B),

[0040] *24 indicates the relationship with L 2 . bond.

[0041] Selected from R 121 ~R 128 One of them is a single bond that bonds with *25.

[0042] R is not the single bond mentioned above. 121 ~R 128 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 12 carbon atoms.

[0043] Selected from R that is not one of the above single bonds 121 ~R 128(Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.)

[0044] [Chemical Formula 4]

[0045]

[0046] (In equation (2C),

[0047] *26 indicates the relationship with L 2 . bond.

[0048] Selected from R 131 ~R 138 One of them is a single bond that bonds with *27.

[0049] R is not the single bond mentioned above. 131 ~R 138 and R 139 ~R 140 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 12 carbon atoms.

[0050] Selected from R that is not one of the above single bonds 131 ~R 138 and R 139 ~R 140 (Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.)

[0051] [Chemical Formula 5]

[0052]

[0053] (In equation (2D),

[0054] *28 indicates the relationship with L 2 . bond.

[0055] X 1 For oxygen atoms, sulfur atoms, -CR a R b or -NR c .

[0056] *29 and R 141 ~R 148 R 200 ~R 203 R a R b Or R c Any one of the bonds in.

[0057] In *29 and R a and R b In the case of one of them being bonded, R a and R bOne of them is a single bond bonded to *29 or a divalent group bonded to *29.

[0058] p is 0 or 1.

[0059] When p is 0, X 1 For oxygen atoms, sulfur atoms, -CR a R b or -NR c At that time, selected from R a R b R c and R 141 ~R 148 One of them is a single bond that bonds with *29.

[0060] When p is 1, X 1 For -CR a R b or -NR c At that time, R 145 With R 146 R 146 With R 147 Or R 147 With R 148 One of them is a single bond bonded to *e, and the other is a single bond bonded to *f, selected from R bonds that are not bonded to *e or *f. 145 ~R 148 R 141 ~R 144 R 200 ~R 203 R a R b and R c One of them is a single bond that bonds with *29.

[0061] When p is 1, X 1 When R is an oxygen atom or a sulfur atom 145 With R 146 R 146 With R 147 Or R 147 With R 148 One of them is a single bond bonded to *e, and the other is a single bond bonded to *f, selected from R bonds that are not bonded to *e or *f. 145 ~R 148 R 141 ~R 144 and R 200 ~R 203 One of them is a single bond that bonds with *29.

[0062] R is not the single bond mentioned above. 141 ~R 148 R is not one of the single bonds mentioned above.200 ~R 203 R is neither a single bond nor a divalent group as described above. a and R b and R c Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 5 to 13 carbon atoms.

[0063] Among them, R a and R b The unsubstituted alkyl group indicates that the hydrogen atoms have not been deuterated.

[0064] Selected from R that is not one of the above single bonds 141 ~R 148 And R that is not a single bond as described above 200 ~R 203 (Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.)

[0065]

Chemical Formula 6

[0066]

[0067] (In equation (2E),

[0068] *30 indicates the relationship with L 2 . bond.

[0069] Selected from R 151 ~R 155 One of them is a single bond bonded to *31, selected from R 151 ~R 155 The other one is a single bond that bonds with *32.

[0070] R is not the single bond mentioned above. 151 ~R 155 Each is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group.

[0071] Selected from R that is not one of the above single bonds 151 ~R 155 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0072] R 161 ~R 165 and R 171 ~R 175 Each is independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.

[0073] Selected from R which is not a hydrogen atom 161 ~R 165At least one pair of adjacent two atoms in the form of a benzene ring are bonded to each other to form one or more unsubstituted benzene rings, or they are not bonded to each other and do not form a ring.

[0074] Selected from R which is not a hydrogen atom 171 ~R 175 (At least one pair of adjacent two atoms in the form of a benzene ring are bonded to each other to form one or more unsubstituted benzene rings, or they are not bonded to each other and therefore do not form a ring.)

[0075] [Chemical Formula 7]

[0076]

[0077] (In equation (2F),

[0078] *33 indicates the relationship with L 2 . bond.

[0079] Selected from R 181 ~R 192 One of them is a single bond that bonds with *34.

[0080] R is not the single bond mentioned above. 181 ~R 192 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 12 carbon atoms.

[0081] Selected from R that is not one of the above single bonds 181 ~R 192 (Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.)

[0082] [Chemical Formula 8]

[0083]

[0084] (In equation (2G),

[0085] *35 indicates the relationship with L 2 . bond.

[0086] R 301 ~R 308 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 5 to 13 carbon atoms.

[0087] Selected from R 301 ~R 308 (Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.)

[0088] L 1 and L 2Each is an arylene group that is independently a single bond or substituted or unsubstituted, with 6 to 30 carbon atoms in a cyclic structure.

[0089] Among them, R selected from the A of the benzene ring 1 ~R 4 The group of hydrogen atoms represented by L 1 The hydrogen atom group of the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aforementioned arylene group, or the hydrogen atom group of the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, and L 2 The hydrogen atoms in at least one of the hydrogen atom groups in the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aforementioned arylene group, or in the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, are deuterated.

[0090] In L 1 When it is a single bond, it is selected from L. 2 The hydrogen atom group of the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aforementioned arylene group, or the hydrogen atom group of the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, and Ar 1 The hydrogen atom group of the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aforementioned aryl group, or the hydrogen atom group of the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, and Ar 1 The hydrogen atom group of the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the aforementioned heterocyclic group, and the R on benzene ring A. 1 ~R 4 At least one hydrogen atom in the indicated hydrogen atom group is deuterated.

[0091] In L 2 When it is a single bond, it is selected from L. 1 The hydrogen atom group of the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aforementioned arylene group, or the hydrogen atom group of the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, and Ar 2 The hydrogen atom group of the unsubstituted benzene ring directly attached to the central nitrogen atom in the aryl group of formulas (2A) to (2G), or the hydrogen atom group of the unsubstituted fused benzene ring directly attached to the central nitrogen atom, and Ar 2 The hydrogen atom groups of the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the heterocyclic group represented in formulas (2A) to (2G), and the R on benzene ring A 1 ~R 4 At least one hydrogen atom in the indicated hydrogen atom group is deuterated.

[0092] In L 1 and L 2 When it is a single bond, it is selected from Ar1 The hydrogen atom group of the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aforementioned aryl group, or the hydrogen atom group of the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, and Ar 1 The hydrogen atom group and Ar atom group represented by the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the aforementioned heterocyclic group. 2 The hydrogen atom group of the unsubstituted benzene ring directly attached to the central nitrogen atom in the aryl group of formulas (2A) to (2G), or the hydrogen atom group of the unsubstituted fused benzene ring directly attached to the central nitrogen atom, and Ar 2 The hydrogen atom groups of the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the heterocyclic group represented in formulas (2A) to (2G), and the R on benzene ring A 1 ~R 4 At least one hydrogen atom in the indicated hydrogen atom group is deuterated.

[0093] Ar 1 With L 1 No cross-linking, and Ar 2 With L 2 It does not crosslink.

[0094] In another embodiment, the present invention provides a material for an organic EL element comprising the compound shown in formula (1) above.

[0095] In another embodiment, the present invention provides an organic electroluminescent element having a cathode, an anode, and an organic layer located between the cathode and the anode, the organic layer being formed of a single layer or multiple layers including a light-emitting layer, wherein at least one layer selected from the single layer and multiple layers constituting the organic layer contains the aforementioned compound.

[0096] In another embodiment, the present invention provides an electronic device comprising the above-described organic electroluminescent element.

[0097] The effects of the invention

[0098] Organic EL elements containing the compound shown in formula (1) above exhibit improved element performance. Attached Figure Description

[0099] Figure 1 This is a schematic diagram illustrating an example of the layer configuration of an organic EL element according to one aspect of the present invention.

[0100] Figure 2 This is a schematic diagram illustrating another example of the layer configuration of an organic EL element according to one aspect of the present invention.

[0101] Figure 3This is a schematic diagram illustrating another example of the layer configuration of an organic EL element according to one aspect of the present invention. Detailed Implementation

[0102] [definition]

[0103] In this specification, a hydrogen atom means an isotope containing different numbers of neutrons, namely protium, deuterium, and tritium.

[0104] 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.

[0105] 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.

[0106] 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.

[0107] 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.

[0108] 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.

[0109] 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.

[0110] In this specification, "unsubstituted ZZ group" means "substituted or unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".

[0111] 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.

[0112] 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.

[0113] Substituents described in this specification

[0114] The substituents described in this specification are explained below.

[0115] 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.

[0116] 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.

[0117] 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.

[0118] 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.

[0119] 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.

[0120] 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.

[0121] 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.

[0122] 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.

[0123] 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.

[0124] • "Substituted or unsubstituted aryl groups"

[0125] 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.

[0126] "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.

[0127] • Unsubstituted aryl groups (specific example group G1A):

[0128] phenyl,

[0129] p-phenyl,

[0130] metaphenyl,

[0131] o-phenyl,

[0132] p-terphenyl-4-yl,

[0133] p-terphenyl-3-yl,

[0134] p-terphenyl-2-yl,

[0135] m-terphenyl-4-yl,

[0136] m-terphenyl-3-yl,

[0137] m-terphenyl-2-yl,

[0138] o-terphenyl-4-yl

[0139] o-terphenyl-3-yl

[0140] o-terphenyl-2-yl,

[0141] 1-Naphthyl,

[0142] 2-Naphthyl,

[0143] Anthryl,

[0144] Benzoanthryl,

[0145] Phenanthryl,

[0146] Benzo[ghi]phenanthryl,

[0147] Phenalenyl,

[0148] Pyrenyl,

[0149] Chrysenyl,

[0150] Benzo[rst]chrysenyl,

[0151] Triphenylenyl,

[0152] Benzo[a]triphenylenyl,

[0153] Tetracenyl,

[0154] Pentacenyl,

[0155] Fluorenyl,

[0156] 9,9'-Spirobi[fluorenyl],

[0157] Benzo[h]fluorenyl,

[0158] Dibenzo[a,c]fluorenyl,

[0159] Fluoranthenyl,

[0160] Benzo[k]fluoranthenyl,

[0161] Perylenyl and

[0162] monovalent aryl groups derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-1) to (TEMP-15).

[0163]

Chemical Formula 9

[0164]

[0165]

Chemical Formula 10

[0166]

[0167] · Substituted aryl groups (specific example group G1B):

[0168] o-Tolyl,

[0169] m-Tolyl,

[0170] p-Tolyl,

[0171] p-Xylyl,

[0172] m-Xylyl,

[0173] o-xylyl,

[0174] p-isopropylphenyl,

[0175] m-Isopropylphenyl,

[0176] o-isopropylphenyl,

[0177] p-tert-butylphenyl,

[0178] m-tert-butylphenyl,

[0179] o-tert-butylphenyl,

[0180] 3,4,5-Trimethylphenyl

[0181] 9,9-Dimethylfluorenyl,

[0182] 9,9-Diphenylfluorenyl

[0183] 9,9-Bis(4-methylphenyl)fluorenyl,

[0184] 9,9-Bis(4-isopropylphenyl)fluorenyl,

[0185] 9,9-Bis(4-tert-butylphenyl)fluorenyl,

[0186] cyanophenyl,

[0187] Triphenylsilylphenyl

[0188] Trimethylsilylphenyl

[0189] Phenynaphthyl,

[0190] Naphthylphenyl and

[0191] 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.

[0192] • "Substituted or unsubstituted heterocyclic groups"

[0193] 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.

[0194] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.

[0195] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0196] 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".

[0197] "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.

[0198] 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).

[0199] 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).

[0200] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1):

[0201] pyrrole,

[0202] Imidazole group,

[0203] Pyrazolyl,

[0204] Triazole group,

[0205] Tetrazolyl,

[0206] Oxazolyl,

[0207] Isoxazolyl,

[0208] Oxadiazole group,

[0209] Thiazole group,

[0210] Isothiazolyl,

[0211] Thiadiazole group,

[0212] pyridyl,

[0213] pyridazinyl,

[0214] Pyrimidine group,

[0215] Pyrazinyl,

[0216] Triazine group

[0217] Indole,

[0218] Isoindolyl,

[0219] Indazine-based

[0220] Quinazine-based

[0221] Quinoline,

[0222] Isoquinoline,

[0223] Crenoline group

[0224] Phthaloazine

[0225] Quinazolinyl,

[0226] Quinoxaloyl,

[0227] Benzimidazole group,

[0228] Indazole group,

[0229] phenanthroline,

[0230] phenanthridine,

[0231] acridine group,

[0232] Phenazine group,

[0233] Carbazolyl,

[0234] Benzocarbazolyl,

[0235] Morpholinyl,

[0236] phenoxazine group,

[0237] phenothiazine group,

[0238] Azacarbazolyl, and

[0239] Diazacarbazolyl.

[0240] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2):

[0241] furanyl,

[0242] Oxazolyl,

[0243] Isoxazolyl,

[0244] Oxadiazole group,

[0245] Xuton base,

[0246] Benzofuranyl,

[0247] Isobenzofuranyl,

[0248] Dibenzofuranyl,

[0249] Naphthobenzofuranyl,

[0250] Benzoxazolyl,

[0251] Benzisoxazole group,

[0252] phenoxazine group,

[0253] Morpholinyl,

[0254] Dinaphthylfuranyl,

[0255] Azadibenzofuranyl,

[0256] diazadibenzofuranyl,

[0257] Azanaphthalenebenzofuranyl and

[0258] Diazanaphthenebenzofuranyl.

[0259] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3):

[0260] Thiophene group

[0261] Thiazole group,

[0262] Isothiazolyl,

[0263] Thiadiazole group,

[0264] benzothienyl

[0265] isobenzothienyl

[0266] dibenzothienyl

[0267] Naphthobenzothienyl

[0268] Benzothiazolyl,

[0269] Benzisothiazolyl,

[0270] phenothiazine group,

[0271] dinaphthothienyl

[0272] azadibenzothienyl

[0273] diazadibenzothienyl

[0274] azanaphthobenzothienyl and

[0275] diazanaphthobenzothienyl.

[0276] • 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):

[0277]

Chemical Formula 11

[0278]

[0279]

Chemical Formula 12

[0280]

[0281] 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.

[0282] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y AWhen 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.

[0283] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1):

[0284] (9-phenyl)carbazole group,

[0285] (9-Biphenyl)carbazolyl,

[0286] (9-Phenyl)phenylcarbazolyl,

[0287] (9-Naphthyl)carbazole,

[0288] Diphenylcarbazole-9-yl,

[0289] Phenylexacarbazole-9-yl,

[0290] Methylbenzimidazole,

[0291] Ethylbenzimidazole,

[0292] Phenylacetyl,

[0293] Biphenyltriazine

[0294] diphenyltriazine group,

[0295] phenylquinazolinyl, and

[0296] Biphenylquinazolinyl.

[0297] • Heterocyclic groups containing oxygen atoms (specific example group G2B2):

[0298] Phenyl dibenzofuranyl,

[0299] Methyldibenzofuranyl,

[0300] tert-butyldibenzofuranyl and

[0301] The monovalent residue of [9H-xanton-9,9'-[9H]fluorene].

[0302] • Heterocyclic groups containing sulfur atoms (specific example group G2B3):

[0303] Phenyl dibenzothiophene,

[0304] Methyldibenzothiophene,

[0305] tert-butyldibenzothiophene and

[0306] The monovalent residue of [9H-thiophene-9,9'-[9H]fluorene].

[0307] • 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):

[0308] 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.

[0309] • "Substituted or unsubstituted alkyl groups"

[0310] 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.

[0311] "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.

[0312] • Unsubstituted alkyl groups (specific example group G3A):

[0313] methyl,

[0314] Ethyl,

[0315] n-propyl,

[0316] Isopropyl,

[0317] n-Butyl,

[0318] Isobutyl,

[0319] sec-butyl and

[0320] tert-butyl.

[0321] • Substituted alkyl groups (specific example group G3B):

[0322] Heptafluoropropyl (including isomers),

[0323] Pentafluoroethyl,

[0324] 2,2,2-Trifluoroethyl and

[0325] Trifluoromethyl

[0326] • "Substituted or unsubstituted alkenyl groups"

[0327] 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.

[0328] "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.

[0329] • Unsubstituted alkenyl groups (specific example group G4A):

[0330] vinyl,

[0331] Allyl

[0332] 1-Butenyl,

[0333] 2-Butenyl and

[0334] 3-Butenyl.

[0335] • Substituted alkenyl groups (specific example group G4B):

[0336] 1,3-Butadienyl,

[0337] 1-Methylvinyl

[0338] 1-Methylallyl,

[0339] 1,1-Dimethylallyl,

[0340] 2-Methylallyl and

[0341] 1,2-Dimethylallyl.

[0342] • "Substituted or unsubstituted alkynyl groups"

[0343] 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".

[0344] "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.

[0345] • Unsubstituted alkynyl group (specific example group G5A):

[0346] Acetylene group.

[0347] • "Substituted or unsubstituted cycloalkyl groups"

[0348] 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.

[0349] "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.

[0350] • Unsubstituted cycloalkyl groups (specific example group G6A):

[0351] Cyclopropyl

[0352] Cyclobutyl,

[0353] Cyclopentyl,

[0354] Cyclohexyl,

[0355] 1-Adamantyl,

[0356] 2-Adamantyl,

[0357] 1-norborneol and

[0358] 2-norborneol.

[0359] • Substituted cycloalkyl groups (specific example group G6B):

[0360] 4-Methylcyclohexyl.

[0361] ·"-Si(R 901 (R) 902 (R) 903 The group shown in the figure”

[0362] 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:

[0363] -Si(G1)(G1)(G1),

[0364] -Si(G1)(G2)(G2),

[0365] -Si(G1)(G1)(G2),

[0366] -Si(G2)(G2)(G2),

[0367] -Si(G3)(G3)(G3) and

[0368] -Si(G6)(G6)(G6). Here.

[0369] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0370] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0371] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0372] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0373] In -Si(G1)(G1)(G1), multiple G1s may be identical or different from each other.

[0374] In -Si(G1)(G2)(G2), multiple G2s may be the same or different from each other.

[0375] In -Si(G1)(G1)(G2), multiple G1s may be the same or different from each other.

[0376] In -Si(G2)(G2)(G2), multiple G2s may be the same or different from each other.

[0377] In -Si(G3)(G3)(G3), multiple G3s may be identical or different from each other.

[0378] In -Si(G6)(G6)(G6), multiple G6s may be identical or different from each other.

[0379] ·“-O-(R 904 The group shown in the figure”

[0380] 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:

[0381] -O(G1)

[0382] -O(G2),

[0383] -O(G3) and

[0384] -O(G6).

[0385] Here,

[0386] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0387] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0388] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0389] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0390] ·“-S-(R 905 The group shown in the figure”

[0391] 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:

[0392] -S(G1)

[0393] -S(G2),

[0394] -S(G3) and

[0395] -S(G6).

[0396] Here,

[0397] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0398] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0399] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0400] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0401] ·"-N(R 906 (R) 907 The group shown in the figure”

[0402] 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:

[0403] -N(G1)(G1),

[0404] -N(G2)(G2),

[0405] -N(G1)(G2),

[0406] -N(G3)(G3) and

[0407] -N(G6)(G6).

[0408] Here,

[0409] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0410] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0411] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0412] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0413] In -N(G1)(G1), multiple G1s may be the same or different from each other.

[0414] In -N(G2)(G2), multiple G2s may be the same or different from each other.

[0415] In -N(G3)(G3), multiple G3s may be the same or different from each other.

[0416] In -N(G6)(G6), multiple G6s may be the same or different from each other.

[0417] • "Halogen atom"

[0418] Specific examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0419] • "Substituted or unsubstituted fluoroalkyl groups"

[0420] 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.

[0421] • "Substituted or unsubstituted haloalkyl groups"

[0422] 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.

[0423] • "Substituted or unsubstituted alkoxy groups"

[0424] 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.

[0425] • "Substituted or unsubstituted alkylthio groups"

[0426] 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.

[0427] • "Substituted or unsubstituted aryloxy groups"

[0428] 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.

[0429] • "Substituted or unsubstituted arylthio groups"

[0430] 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.

[0431] • "Substituted or unsubstituted trialkylsilyl groups"

[0432] 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.

[0433] • "Substituted or unsubstituted aralkyl groups"

[0434] 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.

[0435] 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.

[0436] 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.

[0437] 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.

[0438] In this specification, the carbazoyl group, unless otherwise specified herein, specifically refers to any one of the following groups.

[0439]

Chemical Formula 13

[0440]

[0441] In this specification, (9-phenyl)carbazolyl refers specifically to any one of the following groups unless otherwise specified herein.

[0442]

Chemical Formula 14

[0443]

[0444] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.

[0445] In this specification, dibenzofuranyl and dibenzothiopheneyl are specifically any one of the following groups unless otherwise stated in this specification.

[0446]

Chemical Formula 15

[0447]

[0448] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.

[0449] 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.

[0450] • "Substituted or unsubstituted aryl groups"

[0451] 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.

[0452] • "Substituted or unsubstituted divalent heterocyclic groups"

[0453] 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.

[0454] • "Substituted or unsubstituted alkylene compounds"

[0455] 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.

[0456] 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).

[0457] [Chemical Formula 16]

[0458]

[0459]

Chemical Formula 17

[0460]

[0461] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0462] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.

[0463] [Chemical Formula 18]

[0464]

[0465] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0466] Formulas Q9 and Q 10 They can form rings by bonding with each other via single bonds.

[0467] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.

[0468] [Chemical Formula 19]

[0469]

[0470] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0471] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.

[0472] 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).

[0473]

Chemical Formula 20

[0474]

[0475]

Chemical Formula 21

[0476]

[0477]

Chemical Formula 22

[0478]

[0479] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0480]

Chemical Formula 23

[0481]

[0482]

Chemical Formula 24

[0483]

[0484] [Chemical Formula 25]

[0485]

[0486]

Chemical Formula 26

[0487]

[0488] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0489] The above is an explanation of "substituents described in this specification".

[0490] • "Cases where bonds form rings"

[0491] 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".

[0492] 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.

[0493] [Chemical Formula 27]

[0494]

[0495] For example, in the case of R 921 ~R 930 In the case of "one or more groups 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.

[0496] 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).

[0497] [Chemical Formula 28]

[0498]

[0499] 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 .

[0500] [Chemical Formula 29]

[0501]

[0502] 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.

[0503] "Unsaturated rings" refer to aromatic hydrocarbon rings or aromatic heterocycles. "Saturated rings" refer to aliphatic hydrocarbon rings or non-aromatic heterocycles.

[0504] 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.

[0505] 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.

[0506] 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.

[0507] "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.

[0508] 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.

[0509] 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.

[0510] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".

[0511] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".

[0512] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.

[0513] Unless otherwise stated in this specification, the "unsaturated ring" is preferably a benzene ring.

[0514] 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.

[0515] 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.

[0516] 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.

[0517] 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").

[0518] Substituents when described as "substituted or unsubstituted"

[0519] 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...

[0520] Unsubstituted alkyl groups having 1 to 50 carbon atoms

[0521] Unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0522] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms

[0523] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0524] -Si(R 901 (R) 902 (R) 903 ),

[0525] -O-(R 904 ),

[0526] -S-(R 905 ),

[0527] -N(R 906 (R) 907 ),

[0528] Halogen atom, cyano group, nitro group,

[0529] Unsubstituted aryl groups with 6 to 50 carbon atoms and

[0530] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms

[0531] Groups, etc., in the composition group

[0532] Here, R 901 ~R 907 Each independently

[0533] hydrogen atom,

[0534] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0535] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0536] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0537] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0538] In R 901 When there are more than two, more than two R 901 They are the same or different.

[0539] In R 902 When there are more than two, more than two R 902 They are the same or different.

[0540] In R 903 When there are more than two, more than two R 903 They are the same or different.

[0541] In R 904 When there are more than two, more than two R 904 They are the same or different.

[0542] In R 905 When there are more than two, more than two R 905 They are the same or different.

[0543] In R 906 When there are more than two, more than two R 906 They are the same or different.

[0544] In R 907 When there are more than two, more than two R 907 They are the same or different.

[0545] In one embodiment, the substituents described above as "substituted or unsubstituted" are selected freely.

[0546] Alkyl groups with 1 to 50 carbon atoms

[0547] Aryl groups with 6 to 50 carbon atoms and

[0548] Groups in the group consisting of heterocyclic groups with 5 to 50 cyclic atoms.

[0549] In one embodiment, the substituents described above as "substituted or unsubstituted" are selected freely.

[0550] Alkyl groups having 1 to 18 carbon atoms

[0551] aryl groups with 6 to 18 carbon atoms and

[0552] Groups in the group consisting of heterocyclic groups with 5 to 18 cyclic atoms.

[0553] Specific examples of the substituents mentioned above are the specific examples of the substituents described in the section "Substituents as described in this specification" above.

[0554] 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.

[0555] 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.

[0556] 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.

[0557] The compounds of the present invention will be described below.

[0558] The compounds of the present invention are represented by the following formula (1) and have at least one deuterium atom. Hereinafter, the compounds of the present invention represented by the formulas contained in formula (1) and formula (1-1) described below are sometimes referred to simply as "inventive compounds".

[0559]

Chemical Formula 30

[0560]

[0561] The symbols in equation (1) and equation (1-1) described below will be explained below. It should be noted that the same symbols have the same meaning.

[0562] In equation (1),

[0563] N ＊ The central nitrogen atom,

[0564] R 1 ~R 4 and R 11 ~R 18 Each is an independent hydrogen atom.

[0565] Ar 1 It is an aryl group with 6 to 50 carbon atoms that is substituted or unsubstituted, or a heterocyclic group with 5 to 50 carbon atoms that is substituted or unsubstituted.

[0566] In the case of substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, the substituents described as "substituted or unsubstituted" are each independently a halogen, an unsubstituted alkyl group with 1 to 18 carbon atoms, an unsubstituted cycloalkyl group with 3 to 20 carbon atoms, or an unsubstituted aryl group with 6 to 18 carbon atoms, wherein the hydrogen atoms of the unsubstituted alkyl group are not deuterated.

[0567] When a heterocyclic group with 5 to 50 cyclic atoms is described as "substituted or unsubstituted", the substituent is independently a halogen, an unsubstituted alkyl group with 1 to 18 carbon atoms, or an unsubstituted cycloalkyl group with 3 to 20 cyclic carbon atoms.

[0568] Ar 1 The details of the substituted or unsubstituted aryl groups with 6 to 50 carbon atoms are the same as those described in "Substituents as Described in this Specification". Preferably, the unsubstituted aryl group is selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl and phenanthrene.

[0569] Ar 1Examples of unsubstituted alkyl groups with 1 to 18 carbon atoms in the substituted or unsubstituted aryl groups having 6 to 50 carbon atoms, when expressed as "substituted or unsubstituted," include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, pentyl, isopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Preferably, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl; more preferably, methyl, ethyl, isopropyl, or tert-butyl; and even more preferably, methyl or tert-butyl.

[0570] Ar 1 Examples of unsubstituted cycloalkyl groups with 3 to 20 carbon atoms in the substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, when expressed as "substituted or unsubstituted," include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl. Preferably, cyclopropyl, cyclobutyl, cyclohexyl, 1-adamantyl, or 1-norbornyl are used.

[0571] Ar 1 Examples of unsubstituted aryl groups with 6 to 50 carbon atoms, when described as "substituted or unsubstituted," include phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenatenyl, penfenyl, pyrene, phenyl, fluorene, and triphenylenyl. Phenyl, biphenyl, naphthyl, phenanthrene, anthracene, fluorene, or triphenylenyl are preferred.

[0572] Ar 1 The details of the heterocyclic groups with 5 to 50 cyclic atoms, whether substituted or unsubstituted, are the same as those described in "Substituents as Described in this Specification". Preferably, the unsubstituted heterocyclic group is selected from the group consisting of benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, and carbazole.

[0573] Ar 1Examples of unsubstituted alkyl groups with 1 to 18 carbon atoms in the heterocyclic groups of 5 to 50 cyclic atoms described above as "substituted or unsubstituted" include: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, pentyl, isopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Preferably, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl; more preferably, methyl, ethyl, isopropyl, or tert-butyl; and even more preferably, methyl or tert-butyl.

[0574] Ar 1 Examples of unsubstituted cycloalkyl groups with 3 to 20 carbon atoms among the heterocyclic groups with 5 to 50 cyclic atoms, when described as "substituted or unsubstituted," include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl. Cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl are preferred, and cyclopropyl, cyclopentyl, or cyclohexyl are more preferred.

[0575] Ar 2 It is represented by the following formulas (2A), (2B), (2C), (2D), (2E), (2F) or (2G).

[0576]

Chemical Formula 31

[0577]

[0578] In equation (2A), *21 represents the relationship with L. 2 . bond.

[0579] In equation (2A), the values ​​selected from R 101 ~R 105 One of them is a single bond bonded to *22, selected from R 106 ~R 110 One of them is a single bond that bonds with *23.

[0580] R is not the single bond mentioned above. 101 ~R 105 and R 106 ~R 110 Each is an independent hydrogen atom and an unsubstituted alkyl group having 1 to 10 carbon atoms.

[0581] Among the unsubstituted alkyl groups having 1 to 10 carbon atoms, examples of such alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, or decyl.

[0582] Preferably, it is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl;

[0583] More preferably, it is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl;

[0584] Further preferred are methyl or tert-butyl;

[0585] Tert-butyl is particularly preferred.

[0586] Selected from R that is not one of the above single bonds 101 ~R 105 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0587] Selected from R that is not one of the above single bonds 106 ~R 110 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0588] In equation (2A), R 111 ~R 115 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 5 to 13 carbon atoms.

[0589] Selected from R 111 ~R 115 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0590] Details and preferred examples of the unsubstituted alkyl groups having 1 to 10 carbon atoms, and for R 101 ~R 105 The records are the same.

[0591] In the above-mentioned unsubstituted aryl groups with 6 to 12 carbon atoms, the aryl group is phenyl, biphenyl, or naphthyl;

[0592] Preferably, it is phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, or 1-naphthyl or 2-naphthyl;

[0593] More preferably, it is phenyl, or 1-naphthyl or 2-naphthyl;

[0594] Phenyl is particularly preferred.

[0595] Among the aforementioned substituted or unsubstituted heteroaryl groups with 5 to 13 cyclic atoms, the heteroaryl group is, for example, pyrroleyl, furanyl, thiopheneyl, pyridinyl, imidazopyridyl, pyridinyl, pyrazinyl, triazinyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiazolyl, triazolyl, tetrazolyl, indoleyl, isoindoleyl, indazinyl, quinazinyl, quinolinyl, isoquinolinyl, terpineyl, phthalazinyl. Quinazolinyl, quinoxolinyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, indazole, benzoisoxazolyl, benzoisothiazolyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothienyl, isobenzothienyl, dibenzothienyl, or carbazolyl;

[0596] Preferably, it is pyrroleyl, furanyl, thiopheneyl, pyridyl, pyrimidinyl, triazineyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, or carbazoyl.

[0597] More preferably, it is benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, carbazoyl (9-carbazoyl, or 1-carbazoyl, 2-carbazoyl, 3-carbazoyl or 4-carbazoyl).

[0598] The substituted heteroaryl groups with 5 to 13 cyclic atoms are, for example, 9-phenylcarbazolyl, 9-biphenylcarbazolyl, 9-phenylphenylcarbazolyl, 9-naphthylcarbazolyl, phenyldibenzofuranyl, or phenyldibenzothienyl (hereinafter the same).

[0599] The aforementioned heteroaryl groups with 5 to 13 cyclic atoms, whether substituted or unsubstituted, also include isomer groups in the presence of isomer groups.

[0600] In equation (2A), j is 0, 1, or 2, and k is 0 or 1. The case where j is 2 and k is 0 is excluded.

[0601] When j=0 and k=0, *23 means *21.

[0602] When j=0 and k=1, *22 means *21.

[0603] When j=1 and k=0, *23 means *22.

[0604] In one embodiment of the invention, j is 0 and k is 0. In this case, *23 represents *21, and equation (2A) is represented by the following equation.

[0605]

Chemical Formula 32

[0606]

[0607] In another embodiment of the invention, j is 0 and k is 1. In this case, *22 represents *21, and equation (2A) is represented by the following equation.

[0608]

Chemical Formula 33

[0609]

[0610] In another embodiment of the invention, j is 1 and k is 0. In this case, *23 represents *22, and equation (2A) is represented by the following equation.

[0611] [Chemical Formula 34]

[0612]

[0613] In another embodiment of the invention, j is 1 and k is 1. In this case, equation (2A) is represented by the following equation.

[0614]

Chemical Formula 35

[0615]

[0616] In another embodiment of the invention, j is 2 and k is 1. In this case, equation (2A) is represented by the following equation.

[0617]

Chemical Formula 36

[0618]

[0619] The group represented by formula (2A) is preferably represented by the following formula. In the following formula, R is omitted for simplification.

[0620]

Chemical Formula 37

[0621]

[0622] R is not a single bond that bonds with *22 101 ~R 105 R is not a single bond that bonds with *23. 106 ~R 110 and R 111 ~R 115 Both can be hydrogen atoms.

[0623] [Chemical Formula 38]

[0624]

[0625] In equation (2B), *24 represents L 2 . bond.

[0626] In equation (2B), the values ​​selected from R 121 ~R 128 One of them is a single bond that bonds with *25.

[0627] R is not the single bond mentioned above. 121 ~R 128 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 12 carbon atoms.

[0628] Selected from R that is not one of the above single bonds 121 ~R 128 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0629] R 121 ~R 128 Details and preferred examples of the unsubstituted alkyl groups having 1 to 10 carbon atoms as shown above, and for the purposes of R above 101 ~R 105 The records are the same.

[0630] R 121 ~R 128 The unsubstituted aryl group with 6 to 12 carbon atoms mentioned above and the R mentioned above 111 ~R 115 The records are the same.

[0631] In one embodiment of the present invention, preferably, the material is selected from R. 121 R 124 R 125 and R 128 One of them is a single bond that bonds with *25.

[0632] R is not a single bond that bonds with *25 121 ~R 128 Both can be hydrogen atoms.

[0633] [Chemical Formula 39]

[0634]

[0635] In equation (2C), *26 represents L 2 . bond.

[0636] In equation (2C), the values ​​selected from R 131 ~R 138 One of them is a single bond that bonds with *27.

[0637] R is not the single bond mentioned above. 131~R 138 and R 139 ~R 140 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 12 carbon atoms.

[0638] Selected from R that is not one of the above single bonds 131 ~R 138 and R 139 ~R 140 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0639] R 131 ~R 140 Details and preferred examples of the unsubstituted alkyl groups having 1 to 10 carbon atoms as shown above, and for the purposes of R above 101 ~R 105 The records are the same.

[0640] R 131 ~R 140 Details and preferred examples of the unsubstituted aryl groups with 6 to 12 carbon atoms described above, and for the above R 111 ~R 115 The records are the same.

[0641] In one embodiment of the present invention, preferably, the material is selected from R. 137 and R 138 One of them is a single bond bonded to *27, and more preferably, R 137 It is a single bond that bonds with *27.

[0642] R is not a single bond that bonds with *27 131 ~R 138 and R 139 ~R 140 Both can be hydrogen atoms.

[0643]

Chemical Formula 40

[0644]

[0645] In equation (2D), *28 represents the relationship with L. 2 . bond.

[0646] In equation (2D), X 1 For oxygen atoms, sulfur atoms, -CR a R b or -NR c Preferably, oxygen atoms or -CR a R b .

[0647] *29 and R 141 ~R148 R 200 ~R 203 R a R b Or R c Any one of the bonds in.

[0648] In *29 and R a and R b In the case of one of them being bonded, R a and R b One of them is a single bond bonded to *29 or a divalent group bonded to *29.

[0649] As R a Or R b The divalent groups that can be selected include, for example, unsubstituted phenylene, unsubstituted biphenylene, and unsubstituted naphthylene, preferably unsubstituted phenylene, more preferably unsubstituted meta-phenylene or unsubstituted para-phenylene.

[0650] In equation (2D), p is 0 or 1.

[0651] When p is 0, X 1 For oxygen atoms, sulfur atoms, -CR a R b or -NR c At that time, selected from R a R b R c and R 141 ~R 148 One of them is a single bond that bonds with *29.

[0652] When p is 1, X 1 For -CR a R b or -NR c At that time, R 145 With R 146 R 146 With R 147 Or R 147 With R 148 One of them is a single bond bonded to *e, and the other is a single bond bonded to *f, selected from R bonds that are not bonded to *e or *f. 145 ~R 148 R 141 ~R 144 R 200 ~R 203 R a R b and R c One of them is a single bond that bonds with *29.

[0653] When p is 1, X 1 When R is an oxygen atom or a sulfur atom 145 With R 146 R 146 With R 147 Or R 147 With R 148 One of them is a single bond bonded to *e, and the other is a single bond bonded to *f, selected from R bonds that are not bonded to *e or *f. 145 ~R 148 R 141 ~R 144 and R 200 ~R 203 One of them is a single bond that bonds with *29.

[0654] In equation (2D), R is not the single bond mentioned above. 141 ~R 148 R is not one of the single bonds mentioned above. 200 ~R 203 R is neither a single bond nor a divalent group as described above. a and R b and R c Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 5 to 13 carbon atoms.

[0655] Among them, R a and R b The unsubstituted alkyl group indicates that the hydrogen atoms have not been deuterated.

[0656] Selected from R that is not one of the above single bonds 141 ~R 148 And R that is not a single bond as described above 200 ~R 203 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0657] R is not the single bond mentioned above. 141 ~R 148 R is not one of the single bonds mentioned above. 200 ~R 203 R is neither a single bond nor a divalent group as described above. a and R b Details and preferred examples of the unsubstituted alkyl groups having 1 to 10 carbon atoms as shown above, and for the purposes of R above 101 ~R 105 The records are the same.

[0658] R is not the single bond mentioned above. 141 ~R 148 R is not one of the single bonds mentioned above. 200 ~R203 R is neither a single bond nor a divalent group as described above. a and R b Details and preferred examples of the unsubstituted aryl groups with 6 to 12 carbon atoms described above, and for the above R 111 ~R 115 The records are the same.

[0659] R is not the single bond mentioned above. 141 ~R 148 R is not one of the single bonds mentioned above. 200 ~R 203 R is neither a single bond nor a divalent group as described above. a and R b Details and preferred examples of the above-mentioned substituted or unsubstituted heteroaryl groups with 5 to 13 cyclic atoms, and for the above-mentioned R 111 ~R 115 The records are the same.

[0660] R is not the single bond mentioned above. 141 ~R 148 R is not one of the single bonds mentioned above. 200 ~R 203 And R that is neither a single bond nor a divalent group as described above. a and R b Both can be hydrogen atoms.

[0661]

Chemical Formula 41

[0662]

[0663] In equation (2E), *30 represents L 2 . bond.

[0664] In equation (2E), the values ​​selected from R 151 ~R 155 One of them is a single bond bonded to *31, selected from R 151 ~R 155 The other one is a single bond that bonds with *32.

[0665] R is not the single bond mentioned above. 151 ~R 155 Each is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group.

[0666] Selected from R that is not one of the above single bonds 151 ~R 155 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0667] R 161 ~R 165 and R 171~R 175 Each is independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.

[0668] Selected from R which is not a hydrogen atom 161 ~R 165 At least one pair of adjacent 2 atoms in the benzene ring can bond together to form one or more unsubstituted benzene rings, or they can not bond together to form a ring.

[0669] Selected from R which is not a hydrogen atom 171 ~R 175 At least one pair of adjacent 2 atoms in the benzene ring can bond to each other to form one or more unsubstituted benzene rings, or they can not bond to each other and thus not form a ring.

[0670] R 151 ~R 155 R 161 ~R 165 and R 171 ~R 175 Details and preferred examples of the unsubstituted alkyl groups having 1 to 10 carbon atoms as shown above, and for the purposes of R above 101 ~R 105 The records are the same.

[0671] In one embodiment of the invention, the material selected from R 161 ~R 165 Two adjacent benzene rings in the form of a substituted or unsubstituted benzene ring are bonded together. In another embodiment of the invention, the benzene ring is selected from R... 161 ~R 165 The two adjacent ones in the structure do not bond to each other and therefore do not form a ring structure.

[0672] In one embodiment of the invention, the material selected from R 171 ~R 175 Two adjacent benzene rings in the form of a substituted or unsubstituted benzene ring are bonded together. In another embodiment of the invention, the benzene ring is selected from R... 171 ~R 175 The two adjacent ones in the structure do not bond to each other and therefore do not form a ring structure.

[0673] R is not the single bond mentioned above. 151 ~R 155 Both can be hydrogen atoms, R 161 ~R 165 Both can be hydrogen atoms, R 171 ~R 175 Both can be hydrogen atoms.

[0674]

Chemical Formula 42

[0675]

[0676] In equation (2F), *33 represents the relationship with L. 2 . bond.

[0677] In equation (2F), the values ​​selected from R are... 181 ~R 192 One of them is a single bond that bonds with *34.

[0678] R is not the single bond mentioned above. 181 ~R 192 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 12 carbon atoms.

[0679] Selected from R that is not one of the above single bonds 181 ~R 192 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0680] R 181 ~R 192 Details and preferred examples of the unsubstituted alkyl groups having 1 to 10 carbon atoms as shown above, and for the purposes of R above 101 ~R 105 The records are the same.

[0681] R 181 ~R 192 Details and preferred examples of the unsubstituted aryl groups with 6 to 12 carbon atoms described above, and for the above R 111 ~R 115 The records are the same.

[0682] In one embodiment of the invention, R 181 For a single bond that bonds with *33, in another scheme, R 182 It is a single bond that bonds with *33.

[0683] R is not the single bond mentioned above. 181 ~R 192 Both can be hydrogen atoms.

[0684]

Chemical Formula 43

[0685]

[0686] In formula (2G), *35 represents L 2 . bond.

[0687] In equation (2G), R 301 ~R 308 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 5 to 13 carbon atoms.

[0688] Selected from R 301 ~R 308 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0689] R 301 ~R 308 Details and preferred examples of the unsubstituted alkyl groups having 1 to 10 carbon atoms as shown above, and for the purposes of R above 101 ~R 105 The records are the same.

[0690] R 301 ~R 308 Details and preferred examples of the unsubstituted aryl groups with 6 to 12 carbon atoms described above, and for the above R 111 ~R 115 The records are the same.

[0691] R 301 ~R 308 Details and preferred examples of the above-mentioned substituted or unsubstituted heteroaryl groups with 5 to 13 cyclic atoms, and for the above-mentioned R 111 ~R 115 The records are the same.

[0692] The above R 301 ~R 308 Both can be hydrogen atoms.

[0693] As a preferred option, Ar 2 It can be expressed by any one of the above equations (2A) to (2G).

[0694] As another option, Ar is preferred. 2 It can be represented by the above formula (2A) or (2B).

[0695] As another option, the preferred one is Ar. 2 It can be represented by the above formulas (2C), (2D) or (2E).

[0696] L 1 and L 2 Each is an arylene group that is independently a single bond or substituted or unsubstituted, with 6 to 30 carbon atoms in a cyclic structure.

[0697] Preferably, in L 1 and L 2 In the substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, the unsubstituted arylene groups are each independently selected from the group consisting of phenylene, biphenylene, naphthylene, and terphenylene.

[0698] Preferably, L 1 and L 2Each can be independently a substituted or unsubstituted meta-phenylene or a substituted or unsubstituted p-phenylene.

[0699] L 1 and L 2 When the substituted or unsubstituted aryl group with 6 to 30 carbon atoms is described as "substituted or unsubstituted", the substituents are each independently a halogen, an unsubstituted alkyl group with 1 to 18 carbon atoms, an unsubstituted cycloalkyl group with 3 to 20 carbon atoms, or an unsubstituted aryl group with 6 to 18 carbon atoms.

[0700] L 1 and L 2 The unsubstituted alkyl group with 1 to 18 carbon atoms in the substituted or unsubstituted aryl group having 6 to 30 carbon atoms, when expressed as "substituted or unsubstituted," can include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, pentyl, isopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Preferably, it is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl; more preferably, it is methyl, ethyl, isopropyl, or tert-butyl; and even more preferably, it is methyl or tert-butyl.

[0701] L 1 and L 2 The unsubstituted aryl group with 6 to 18 carbon atoms among the substituted or unsubstituted aryl groups (when expressed as "substituted or unsubstituted") can be, for example, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenatenyl, penfenyl, pyrene, phenyl, fluorene, and triphenylenyl. Among these, phenyl, biphenyl, naphthyl, phenanthrene, anthracene, fluorene, or triphenylenyl are preferred.

[0702] L 1 and L 2 Examples of unsubstituted cycloalkyl groups with 3 to 20 carbon atoms in the substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, when expressed as "substituted or unsubstituted," include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl. Cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl are preferred, and cyclopropyl, cyclopentyl, or cyclohexyl are more preferred.

[0703] As a solution, in L 2 For substituted or unsubstituted phenylene, Ar 2 As indicated by the above formula (2D), when p is 1, *28 can be interpositionally or adjacently with L. 2 The above-mentioned substituted or unsubstituted phenylene bonds are represented, and in L 1 For substituted or unsubstituted phenylene, Ar 1 When the aforementioned substituted or unsubstituted heterocyclic group with 5 to 50 cyclic atoms is a substituted or unsubstituted naphthobenzofuran group, the aforementioned naphthobenzofuran group may be meta- or ortho-substituted with L 1 The above-mentioned substituted or unsubstituted phenylene bonds are represented.

[0704] The inventive compound contains at least one deuterium atom.

[0705] By using a portion or all of the raw material compound as a deuterated compound, it is possible to intentionally introduce deuterium atoms into the inventive compound.

[0706] Here, examples of starting material compounds that are partially or wholly deuterated include: compounds forming a 9-carbazole group of formula (1), compounds forming a phenylene group containing a benzene ring A of formula (1), and compounds forming a linking group (L) of formula (1). 1 L 2 Compounds of formula (1) with terminal Ar 1 Ar 2 Compounds, etc.

[0707] In equation (1), with L 1 The hydrogen atom directly bonded to the arylene group, and the L 2 The hydrogen atom directly bonded to the arylene group, and Ar 1 The hydrogen atom directly attached to the aryl group, and the Ar group... 1 The hydrogen atom and Ar atom directly bonded to the heterocyclic group are represented. 2 The hydrogen atom directly bonded to the aryl group or directly bonded to the heterocyclic group in formulas (2A) to (2G), R 1 ~R 4 The hydrogen atom and R represent 11 ~R 18 At least one of the hydrogen atoms represented is a deuterium atom.

[0708] That is, in the following formula (1-1), the sum of a, b, c, d, e and f is 1 or more.

[0709]

Chemical Formula 44

[0710]

[0711] In equation (1-1), “Da” represents R. 11 ~R 18 "Db" indicates that "a" of the hydrogen atoms are deuterium atoms, and "Db" indicates R. 1 ~R 4 The hydrogen atoms represented are represented by b deuterium atoms, and "Dc" indicates that they are related to L. 1 The aryl group indicates that c of the hydrogen atoms directly bonded to it are deuterium atoms, and "Dd" indicates that it is bonded to L. 2 The aryl group indicates that d hydrogen atoms are directly bonded to it, and "De" indicates that it is bonded to Ar. 1 "Df" indicates that among the hydrogen atoms directly bonded to the aryl group or directly bonded to the heterocyclic group, e are deuterium atoms. 2 In the formulas (2A) to (2G), f of the hydrogen atoms directly connected to the aryl group or directly connected to the heterocyclic group are deuterium atoms.

[0712] Among them, R selected from the A of the benzene ring 1 ~R 4 The group of hydrogen atoms represented by L 1 The hydrogen atom group of the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aforementioned arylene group, or the hydrogen atom group of the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, and L 2 The hydrogen atoms in at least one of the hydrogen atom groups in the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aforementioned arylene group, or in the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, are deuterated.

[0713] In L 1 When it is a single bond, it is selected from L. 2 The hydrogen atom group of the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aforementioned arylene group, or the hydrogen atom group of the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, and Ar 1 The hydrogen atom group of the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aforementioned aryl group, or the hydrogen atom group of the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, and Ar 1 The hydrogen atom group of the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the aforementioned heterocyclic group, and the R on benzene ring A. 1 ~R 4 At least one hydrogen atom in the indicated hydrogen atom group is deuterated.

[0714] In L 2 When it is a single bond, it is selected from L. 1The hydrogen atom group of the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aforementioned arylene group, or the hydrogen atom group of the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, and Ar 2 The hydrogen atom group of the unsubstituted benzene ring directly attached to the central nitrogen atom in the aryl group of formulas (2A) to (2G), or the hydrogen atom group of the unsubstituted fused benzene ring directly attached to the central nitrogen atom, and Ar 2 The hydrogen atom groups of the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the heterocyclic group represented in formulas (2A) to (2G), and the R on benzene ring A 1 ~R 4 At least one hydrogen atom in the indicated hydrogen atom group is deuterated.

[0715] In L 1 and L 2 When it is a single bond, it is selected from Ar 1 The hydrogen atom group of the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aforementioned aryl group, or the hydrogen atom group of the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, and Ar 1 The hydrogen atom group and Ar atom group represented by the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the aforementioned heterocyclic group. 2 The hydrogen atom group of the unsubstituted benzene ring directly attached to the central nitrogen atom in the aryl group of formulas (2A) to (2G), or the hydrogen atom group of the unsubstituted fused benzene ring directly attached to the central nitrogen atom, and Ar 2 The hydrogen atom groups of the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the heterocyclic group represented in formulas (2A) to (2G), and the R on benzene ring A 1 ~R 4 At least one hydrogen atom in the indicated hydrogen atom group is deuterated.

[0716] Ar 1 With L 1 No cross-linking, and Ar 2 With L 2 It does not crosslink.

[0717] R selected from the benzene ring A directly bonded to the central nitrogen atom 1 ~R 4 The group of hydrogen atoms is represented.

[0718] L 1 The hydrogen atom group represented by the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aforementioned arylene group, or the hydrogen atom group represented by the unsubstituted fused benzene ring directly bonded to the central nitrogen atom.

[0719] L 2The hydrogen atom group represented by the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aforementioned arylene group, or the hydrogen atom group represented by the unsubstituted fused benzene ring directly bonded to the central nitrogen atom.

[0720] Ar 1 The hydrogen atom group represented by the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aforementioned aryl group, or the hydrogen atom group represented by the unsubstituted fused benzene ring directly bonded to the central nitrogen atom.

[0721] Ar 1 The hydrogen atom group represented by the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the aforementioned heterocyclic group...

[0722] Ar 2 The hydrogen atom groups of the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aryl group of formulas (2A) to (2G), or the hydrogen atom groups of the unsubstituted fused benzene ring directly bonded to the central nitrogen atom.

[0723] as well as

[0724] Ar 2 The group of hydrogen atoms in the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the heterocyclic group represented by formulas (2A) to (2G)

[0725] In at least one hydrogen atom group, the ratio of the total number of deuterated hydrogen atoms to the total number of hydrogen atoms in that hydrogen atom group is preferably 65% ​​or more, more preferably 75% or more, even more preferably 85% or more, even more preferably 95% or more, and particularly preferably 100%.

[0726] Preferably, in L 1 and L 2 In the case of substituted or unsubstituted arylene groups with 6 to 30 carbon atoms in the cyclic group, as one scheme, L 1 and L 2 All hydrogen atoms in the unsubstituted benzene ring directly connected to the central nitrogen atom or in the unsubstituted fused benzene ring directly connected to the central nitrogen atom of at least one of the aforementioned aryl groups are deuterated.

[0727] Preferably, in L 1 and L 2 In the case of a single bond, as a solution, Ar 1 The hydrogen atom group of the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aforementioned aryl group, or the hydrogen atom group of the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, or Ar 1In the aforementioned heterocyclic group, more than 50% of the hydrogen atoms in the unsubstituted fused benzene ring directly connected to the central nitrogen atom are deuterated.

[0728] Ar 2 The hydrogen atom group of the unsubstituted benzene ring directly attached to the central nitrogen atom in the aryl group of formulas (2A) to (2G), or the hydrogen atom group of the unsubstituted fused benzene ring directly attached to the central nitrogen atom, or Ar 2 More than 50% of the hydrogen atoms in the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the heterocyclic group represented by formulas (2A) to (2G) are deuterated.

[0729] In L 1 In the case of a single bond, Ar is the preferred option. 1 The hydrogen atom group of the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aforementioned aryl group, or the hydrogen atom group of the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, or Ar 1 More than 50% of the hydrogen atoms in the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the aforementioned heterocyclic group are deuterated.

[0730] In L 2 In the case of a single bond, Ar is the preferred option. 2 The hydrogen atom group of the unsubstituted benzene ring directly attached to the central nitrogen atom in the aryl group of formulas (2A) to (2G), or the hydrogen atom group of the unsubstituted fused benzene ring directly attached to the central nitrogen atom, or Ar 2 More than 50% of the hydrogen atoms in the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the heterocyclic group represented by formulas (2A) to (2G) are deuterated.

[0731] As a preferred approach, the R atom on the benzene ring A, which is directly bonded to the central nitrogen atom, is preferred. 1 ~R 4 The group of hydrogen atoms and L 1 The hydrogen atoms in each group of hydrogen atoms in the unsubstituted benzene ring directly connected to the central nitrogen atom in the aforementioned arylene group, or in each group of hydrogen atoms in the unsubstituted fused benzene ring directly connected to the central nitrogen atom, are deuterated.

[0732] As a preferred approach, the R atom on the benzene ring A, which is directly bonded to the central nitrogen atom, is preferred. 1 ~R 4 The group of hydrogen atoms and L 2The hydrogen atoms in each group of hydrogen atoms in the unsubstituted benzene ring directly connected to the central nitrogen atom in the aforementioned arylene group, or in each group of hydrogen atoms in the unsubstituted fused benzene ring directly connected to the central nitrogen atom, are deuterated.

[0733] As a preferred approach, the R atom on the benzene ring A, which is directly bonded to the central nitrogen atom, is preferred. 1 ~R 4 The group of hydrogen atoms represented by L 1 The hydrogen atom group of the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aforementioned arylene group, or the hydrogen atom group of the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, and L 2 The hydrogen atoms in the unsubstituted benzene ring directly connected to the central nitrogen atom in the aforementioned arylene group, or in the unsubstituted fused benzene ring directly connected to the central nitrogen atom, are deuterated by more than 75%.

[0734] As a preferred approach, the R atom on the benzene ring A, which is directly bonded to the central nitrogen atom, is preferred. 1 ~R 4 The hydrogen atoms in the group represented are all deuterated.

[0735] In one aspect of the present invention,

[0736] (A-1)R 1 ~R 4 All hydrogen atoms can be replaced by deuterium.

[0737] (A-2)R 11 ~R 18 All hydrogen atoms can be replaced by deuterium.

[0738] (A-3)L 1 The unsubstituted aryl group indicates that all hydrogen atoms can be deuterated.

[0739] (A-4)L 2 The unsubstituted aryl group indicates that all hydrogen atoms can be deuterated.

[0740] (A-5)Ar 1 The unsubstituted aryl group indicates that all hydrogen atoms can be deuterated.

[0741] (A-6)Ar 1 The unsubstituted heterocyclic group indicates that all hydrogen atoms can be replaced by deuterium.

[0742] (A-7)Ar 2 The unsubstituted aryl group indicates that all hydrogen atoms can be deuterated.

[0743] (A-8)Ar2 The unsubstituted heterocyclic group indicates that all hydrogen atoms can be deuterated.

[0744] The inventive compound may, corresponding to the above-described structure, simultaneously satisfy two or more of the above conditions (A-1) to (A-8).

[0745] As stated above, the term "hydrogen atom" as used in this specification includes protium, deuterium, and tritium atoms. Therefore, the inventive compounds may contain naturally occurring deuterium atoms.

[0746] Alternatively, deuterium atoms can be intentionally introduced into the inventive compound by using a portion or all of the raw material compound as a deuterated compound. Therefore, in one aspect of the present invention, the inventive compound contains at least one deuterium atom. That is, the inventive compound can be a compound represented by formula (1), wherein at least one of the hydrogen atoms contained in the compound is a deuterium atom.

[0747] The deuteration rate of the inventive compound depends on the deuteration rate of the raw material compound used. Even when using a raw material with a specified deuteration rate, it may contain a certain proportion of protium isotopes from natural sources. Therefore, for the deuteration rate scheme of the inventive compound shown below, the ratio relative to the ratio obtained by simply counting the number of deuterium atoms represented in the chemical formula includes the ratio that takes into account trace amounts of isotopes from natural sources.

[0748] The deuteration rate of the inventive compound is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, even more preferably 10% or more, and even more preferably 20% or more. Furthermore, the deuteration rate can be 1 to 100%, 3 to 80%, 5 to 60%, 10 to 50%, or 20 to 30%.

[0749] The inventive compound can be a mixture comprising a deuterated compound and an undeuterated compound, or a mixture of two or more compounds with different deuteration rates. The deuteration rate of such a mixture is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, even more preferably 10% or more, and even more preferably 20% or more. Furthermore, the deuteration rate can be 1–100%, 3–80%, 5–60%, 10–50%, or 20–30%.

[0750] Except in specific cases, the details of the substituents (optional substituents) described as “substituted or unsubstituted” in the definitions of the above formulas are the same as those described in the section “substituents described as “substituted or unsubstituted””.

[0751] Those skilled in the art can easily manufacture the inventive compounds by referring to the following synthetic examples and known synthetic methods.

[0752] The following examples of inventive compounds are shown, but are not limited to the illustrative compounds below. In addition to the compounds described in the illustrative compounds below, the inventive compounds also include compounds in which a portion of the hydrogen is not deuterated in the synthetic process.

[0753] In the specific examples below, D represents a deuterium atom.

[0754] [Chemical Formula 45]

[0755]

[0756]

Chemical Formula 46

[0757]

[0758] [Chemical Formula 47]

[0759]

[0760] [Chemical Formula 48]

[0761]

[0762] [Chemical Formula 49]

[0763]

[0764] [Chemical Formula 50]

[0765]

[0766]

Chemical Formula 51

[0767]

[0768]

Chemical Formula 52

[0769]

[0770]

Chemical Formula 53

[0771]

[0772] [Chemical Formula 54]

[0773]

[0774]

Chemical Formula 55

[0775]

[0776] [Chemical Formula 56]

[0777]

[0778] [Chemical Formula 57]

[0779]

[0780] [Chemical Formula 58]

[0781]

[0782] [Chemical Formula 59]

[0783]

[0784] [Chemical Formula 60]

[0785]

[0786]

Chemical Formula 61

[0787]

[0788]

Chemical Formula 62

[0789]

[0790]

Chemical Formula 63

[0791]

[0792]

Chemical Formula 64

[0793]

[0794]

Chemical Formula 65

[0795]

[0796]

Chemical Formula 66

[0797]

[0798] [Chemical Formula 67]

[0799]

[0800]

Chemical Formula 68

[0801]

[0802]

Chemical Formula 69

[0803]

[0804] [Chemical Formula 70]

[0805]

[0806]

Chemical Formula 71

[0807]

[0808]

Chemical Formula 72

[0809]

[0810]

Chemical Formula 73

[0811]

[0812] [Chemical Formula 74]

[0813]

[0814] [Chemical Formula 75]

[0815]

[0816] [Chemical Formula 76]

[0817]

[0818]

Chemical Formula 77

[0819]

[0820] [Chemical Formula 78]

[0821]

[0822] [Chemical Formula 79]

[0823]

[0824] [Chemical Formula 80]

[0825]

[0826]

Chemical Formula 81

[0827]

[0828]

Chemical Formula 82

[0829]

[0830]

Chemical Formula 83

[0831]

[0832]

Chemical Formula 84

[0833]

[0834]

Chemical Formula 85

[0835]

[0836]

Chemical Formula 86

[0837]

[0838]

Chemical Formula 87

[0839]

[0840]

Chemical Formula 88

[0841]

[0842]

Chemical Formula 89

[0843]

[0844] [Chemical Formula 90]

[0845]

[0846]

Chemical Formula 91

[0847]

[0848]

Chemical Formula 92

[0849]

[0850] [Chemical Formula 93]

[0851]

[0852] [Chemical Formula 94]

[0853]

[0854] [Chemical Formula 95]

[0855]

[0856]

Chemical Formula 96

[0857]

[0858] [Chemical Formula 97]

[0859]

[0860] [Chemical Formula 98]

[0861]

[0862]

Chemical Formula 99

[0863]

[0864]

Chemical Formula 100

[0865]

[0866]

Chemical Formula 101

[0867]

[0868]

Chemical Formula 102

[0869]

[0870]

Chemical Formula 103

[0871]

[0872] [Chemical Formula 104]

[0873]

[0874] [Chemical Formula 105]

[0875]

[0876] [Chemical Formula 106]

[0877]

[0878] [Chemical Formula 107]

[0879]

[0880] [Chemical Formula 108]

[0881]

[0882] [Chemical Formula 109]

[0883]

[0884]

Chemical Formula 110

[0885]

[0886]

Chemical Formula 111

[0887]

[0888]

Chemical Formula 112

[0889]

[0890]

Chemical Formula 113

[0891]

[0892]

Chemical Formula 114

[0893]

[0894]

Chemical Formula 115

[0895]

[0896]

Chemical Formula 116

[0897]

[0898]

Chemical Formula 117

[0899]

[0900]

Chemical Formula 118

[0901]

[0902]

Chemical Formula 119

[0903]

[0904]

Chemical Formula 120

[0905]

[0906]

Chemical Formula 121

[0907]

[0908]

Chemical Formula 122

[0909]

[0910]

Chemical Formula 123

[0911]

[0912] [Chemical Formula 124]

[0913]

[0914] [Chemical Formula 125]

[0915]

[0916] [Chemical Formula 126]

[0917]

[0918]

Chemical Formula 127

[0919]

[0920] [Chemical Formula 128]

[0921]

[0922] [Chemical Formula 129]

[0923]

[0924]

Chemical Formula 130

[0925]

[0926]

Chemical Formula 131

[0927]

[0928]

Chemical Formula 132

[0929]

[0930]

Chemical Formula 133

[0931]

[0932]

Chemical Formula 134

[0933]

[0934] [Chemical Formula 135]

[0935]

[0936]

Chemical Formula 136

[0937]

[0938]

Chemical Formula 137

[0939]

[0940]

Chemical Formula 138

[0941]

[0942]

Chemical Formula 139

[0943]

[0944] [Chemical Formula 140]

[0945]

[0946]

Chemical Formula 141

[0947]

[0948] [Chemical Formula 142]

[0949]

[0950] [Chemical Formula 143]

[0951]

[0952] [Chemical Formula 144]

[0953]

[0954] [Chemical Formula 145]

[0955]

[0956] [Chemical Formula 146]

[0957]

[0958] [Chemical Formula 147]

[0959]

[0960] [Chemical Formula 148]

[0961]

[0962] [Chemical Formula 149]

[0963]

[0964] [Chemical Formula 150]

[0965]

[0966]

Chemical Formula 151

[0967]

[0968]

Chemical Formula 152

[0969]

[0970]

Chemical Formula 153

[0971]

[0972]

Chemical Formula 154

[0973]

[0974]

Chemical Formula 155

[0975]

[0976] [Chemical Formula 156]

[0977]

[0978] [Chemical Formula 157]

[0979]

[0980] [Chemical Formula 158]

[0981]

[0982] [Chemical Formula 159]

[0983]

[0984] [Chemical Formula 160]

[0985]

Chemical Formula 161

[0986]

[0987] [Chemical Formula 162]

[0988]

[0989] [Chemical Formula 163]

[0990]

[0991] [Chemical Formula 164]

[0992]

[0993] [Chemical Formula 165]

[0994]

[0995]

Chemical Formula 166

[0996]

[0997] [Chemical Formula 167]

[0998]

[0999] [Chemical Formula 168]

[1000]

[1001] [Chemical Formula 169]

[1002]

[1003] [Chemical Formula 170]

[1004]

Chemical Formula 171

[1005]

[1006] [Chemical Formula 172]

[1007]

[1008]

Chemical Formula 173

[1009]

[1010] [Chemical Formula 174]

[1011]

[1012] [Chemical Formula 175]

[1013]

[1014] [Chemical Formula 176]

[1015]

[1016]

Chemical Formula 177

[1017]

[1018] [Chemical Formula 178]

[1019]

[1020] [Chemical Formula 179]

[1021]

[1022] [Chemical Formula 180]

[1023]

Chemical Formula 181

[1024]

[1025]

Chemical Formula 182

[1026]

[1027] [Chemical Formula 183]

[1028]

[1029] [Chemical Formula 184]

[1030]

[1031] [Chemical Formula 185]

[1032]

[1033] [Chemical Formula 186]

[1034]

[1035] [Chemical Formula 187]

[1036]

[1037]

Chemical Formula 188

[1038]

[1039] [Chemical Formula 189]

[1040]

[1041] [Chemical Formula 190]

[1042]

[1043]

Chemical Formula 191

[1044]

[1045] [Chemical Formula 192]

[1046]

[1047] [Chemical Formula 193]

[1048]

[1049] [Chemical Formula 194]

[1050]

[1051] [Chemical Formula 195]

[1052]

[1053] [Chemical Formula 196]

[1054]

[1055] [Chemical Formula 197]

[1056]

[1057] [Chemical Formula 198]

[1058]

[1059]

Chemical Formula 199

[1060]

[1061] [Chemical Formula 200]

[1062]

Chemical Formula 201

[1063]

[1064]

Chemical Formula 202

[1065]

[1066]

Chemical Formula 203

[1067]

[1068]

Chemical Formula 204

[1069]

[1070]

Chemical Formula 205

[1071]

[1072]

Chemical Formula 206

[1073]

[1074] [Chemical Formula 207]

[1075]

[1076] [Chemical Formula 208]

[1077]

[1078]

Chemical Formula 209

[1079]

[1080]

Chemical Formula 210

[1081]

Chemical Formula 211

[1082]

[1083]

Chemical Formula 212

[1084]

[1085]

Chemical Formula 213

[1086]

[1087]

Chemical Formula 214

[1088]

[1089] Materials for organic EL components

[1090] The organic EL element material, as one aspect of the present invention, comprises the inventive compound. The content of the inventive compound in the organic EL element material is 1% by mass or more (including 100%), preferably 10% by mass or more (including 100%), more preferably 50% by mass or more (including 100%), further preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%). The organic EL element material, as one aspect of the present invention, is useful for the manufacture of organic EL elements.

[1091] In one aspect of the present invention, the inventive compound is preferably a hole transport layer material.

[1092] One aspect of this invention relates to a hole transport layer material for organic electroluminescent devices.

[1093] The content of the inventive compound in the material for organic electroluminescent elements is preferably 1% by mass or more (including 100%), more preferably 10% by mass or more (including 100%), further preferably 50% by mass or more (including 100%), even more preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%).

[1094] Organic EL components

[1095] An organic EL element, as one aspect of the present invention, includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer is composed of a single layer or multiple layers including a light-emitting layer, and at least one layer selected from the single layer and multiple layers constituting the organic layer contains the inventive compound.

[1096] Examples of organic layers comprising the inventive compound include hole transport regions (hole injection layers, hole transport layers, electron blocking layers, exciton blocking layers, etc.) disposed between the anode and the light-emitting layer, light-emitting layers, spacer layers, and electron transport regions (electron injection layers, electron transport layers, hole blocking layers, etc.) disposed between the cathode and the light-emitting layer, and are not limited thereto. The inventive compound is preferably used as a material for the hole transport region or the light-emitting layer of a fluorescent or phosphorescent EL element, more preferably as a material for the hole transport region, even more preferably as a material for the hole injection layer, hole transport layer, electron blocking layer, or exciton blocking layer, and particularly preferably as a material for the hole injection layer or the hole transport layer.

[1097] As one aspect of the present invention, the organic EL element can be a monochromatic light-emitting element of the fluorescent or phosphorescent type, or a white light-emitting element of the fluorescent / phosphorescent hybrid type. It can be a simple type with a single light-emitting unit, or a tandem type with multiple light-emitting units, wherein a fluorescent light-emitting element is preferred. Here, "light-emitting unit" refers to the smallest unit that includes an organic layer and is composed of a single layer or multiple layers, at least one of which is selected from the single layer and multiple layers as the light-emitting layer, and emits light by recombination of injected holes and electrons.

[1098] For example, the following are typical component configurations for a simple organic EL element.

[1099] (1) Anode / Light-emitting unit / Cathode

[1100] Alternatively, the aforementioned light-emitting unit can also be a multilayer type with multiple phosphorescent or fluorescent light-emitting layers. In this case, spacer layers may be provided between the light-emitting layers to prevent excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer. A typical layer configuration of a simplified light-emitting unit is shown below. The layers within parentheses are optional.

[1101] (a)(hole injection layer / )hole transport layer / fluorescent layer / electron transport layer( / electron injection layer)

[1102] (b) (Hole injection layer / ) Hole transport layer / First fluorescent layer / Second fluorescent layer / Electron transport layer ( / Electron injection layer)

[1103] (c)(Hole injection layer / )Hole transport layer / phosphorescent layer / spacer layer / fluorescent layer / electron transport layer( / electron injection layer)

[1104] (d)(Hole injection layer / )Hole transport layer / First phosphorescent layer / Second phosphorescent layer / Spacer layer / Fluorescent layer / Electron transport layer( / Electron injection layer)

[1105] (e)(hole injection layer / )hole transport layer / phosphorescent layer / spacer layer / first fluorescent layer / second fluorescent layer / electron transport layer( / electron injection layer)

[1106] (f)(hole injection layer / )hole transport layer / electron blocking layer / fluorescent layer / electron transport layer( / electron injection layer)

[1107] (g)(hole injection layer / )hole transport layer / exciton blocking layer / fluorescent layer / electron transport layer( / electron injection layer)

[1108] (h)(Hole Injection Layer / )First Hole Transport Layer / Second Hole Transport Layer / Fluorescent Layer / Electron Transport Layer( / Electron Injection Layer)

[1109] (h1)(Hole Injection Layer / )First Hole Transport Layer / Second Hole Transport Layer / Third Hole Transport Layer / Fluorescent Layer / Electron Transport Layer( / Electron Injection Layer)

[1110] (i)(hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent layer / first electron transport layer / second electron transport layer( / electron injection layer)

[1111] (i1)(hole injection layer / ) first hole transport layer / second hole transport layer / third hole transport layer / fluorescent layer / first electron transport layer / second electron transport layer( / electron injection layer)

[1112] (j)(hole injection layer / )hole transport layer / fluorescent layer / hole blocking layer / electron transport layer( / electron injection layer)

[1113] (k)(hole injection layer / )hole transport layer / fluorescent layer / exciton blocking layer / electron transport layer( / electron injection layer)

[1114] Each of the aforementioned phosphorescent or fluorescent emitting layers can be configured to display a different emitting color. Specifically, in the aforementioned emitting unit (d), a layer configuration such as (hole injection layer / ) hole transport layer / first phosphorescent emitting layer (red emitting light) / second phosphorescent emitting layer (green emitting light) / spacer layer / fluorescent emitting layer (blue emitting light) / electron transport layer can be used.

[1115] It should be noted that electron blocking layers can be appropriately placed between each light-emitting layer and the hole transport layer or spacer layer. Similarly, hole blocking layers can be appropriately placed between each light-emitting layer and the electron transport layer. By placing electron blocking layers and hole blocking layers, electrons or holes can be confined within the light-emitting layer, thereby increasing the recombination probability of charges in the light-emitting layer and thus improving luminous efficiency.

[1116] The following are typical component configurations for tandem organic EL elements.

[1117] (2) Anode / First Light-Emitting Unit / Intermediate Layer / Second Light-Emitting Unit / Cathode

[1118] Here, the first light-emitting unit and the second light-emitting unit described above can be selected independently from the light-emitting units described above.

[1119] The aforementioned intermediate layer is generally also referred to as an intermediate electrode, intermediate conductive layer, charge generation layer, electron extraction layer, connecting layer, or intermediate insulating layer, and can be constructed using known materials that supply electrons to the first light-emitting unit and holes to the second light-emitting unit.

[1120] Furthermore, when the hole transport layer is a multilayer structure containing two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer in the aforementioned multilayer structure, such as the second hole transport layer in the two-layer structure or the third hole transport layer in the three-layer structure, can function as an electron blocking layer. That is, when the hole transport layer is a multilayer structure containing two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer in the aforementioned multilayer structure can also be used as an electron blocking layer.

[1121] Figure 1 This is a schematic diagram illustrating an example of the configuration of an organic EL element according to one aspect of the present invention. Figure 1The organic EL element 1 shown has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10 disposed between the anode 3 and the cathode 4. The light-emitting unit 10 has a light-emitting layer 5. A hole transport region 6 (hole injection layer, hole transport layer, etc.) is provided between the light-emitting layer 5 and the anode 3, and an electron transport region 7 (electron injection layer, electron transport layer, etc.) is provided between the light-emitting layer 5 and the cathode 4. In addition, an electron blocking layer (not shown) can be provided on the anode 3 side of the light-emitting layer 5, and a hole blocking layer (not shown) can be provided on the cathode 4 side of the light-emitting layer 5. As a result, electrons and holes can be confined in the light-emitting layer 5, thereby further improving the exciton generation efficiency in the light-emitting layer 5.

[1122] Figure 2 This is a schematic diagram illustrating another configuration of an organic EL element according to one aspect of the present invention. Figure 2 The organic EL element 11 shown has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 20 disposed between the anode 3 and the cathode 4. The light-emitting unit 20 has a light-emitting layer 5. The hole transport region disposed between the anode 3 and the light-emitting layer 5 is formed by a hole injection layer 6a, a first hole transport layer 6b, and a second hole transport layer 6c. In addition, the electron transport region disposed between the light-emitting layer 5 and the cathode 4 is formed by a first electron transport layer 7a and a second electron transport layer 7b.

[1123] Figure 3 This is a schematic diagram illustrating another configuration of an organic EL element according to one aspect of the present invention. The organic EL element 12 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 30 disposed between the anode 3 and the cathode 4. The light-emitting unit 30 has a light-emitting layer 5. The hole transport region disposed between the anode 3 and the light-emitting layer 5 is formed by a hole injection layer 6a, a first hole transport layer 6b, a second hole transport layer 6c, and a third hole transport layer 6d. Furthermore, the electron transport region disposed between the light-emitting layer 5 and the cathode 4 is formed by a first electron transport layer 7a and a second electron transport layer 7b.

[1124] exist Figures 1-3 In this embodiment, the light-emitting layer 5 comprises at least one light-emitting layer. The light-emitting layer 5 can be a single layer or a layer comprising multiple layers (e.g., multiple light-emitting layers, multiple light-emitting layers and spacer layers). Preferably, it is composed of multiple layers stacked together.

[1125] It should be noted that in this invention, the host material combined with the fluorescent dopant material (fluorescent emitting material) is called the fluorescent host material, and the host material combined with the phosphorescent dopant material is called the phosphorescent host material. The distinction between fluorescent and phosphorescent hosts is not solely based on molecular structure. That is, a phosphorescent host material refers to the material that forms a phosphorescent emitting layer containing phosphorescent dopant, and does not mean that it cannot be used as a material to form a fluorescent emitting layer. The same applies to fluorescent hosts.

[1126] substrate

[1127] The substrate serves as a support for the organic EL element. Examples of substrates include sheets made of glass, quartz, or plastic. Flexible substrates can also be used. Examples of flexible substrates include plastic substrates formed from polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. Inorganic vapor-deposited films can also be used.

[1128] anode

[1129] The anode formed on the substrate is preferably a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically 4.0 eV or higher). Examples of such anodes include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the aforementioned metals (e.g., titanium nitride).

[1130] These materials are typically formed into films using sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1–10 wt% zinc oxide relative to indium oxide, and indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5–5 wt% tungsten oxide and 0.1–1 wt% zinc oxide relative to indium oxide. Alternatively, they can be fabricated using vacuum evaporation, coating, inkjet printing, spin coating, and other methods.

[1131] Hole transport region

[1132] As described above, the organic layer may include a hole transport region located between the anode and the light-emitting layer. The hole transport region is composed of a hole injection layer, a hole transport layer, an electron blocking layer, etc. Preferably, the hole transport region contains the inventive compound. Preferably, the inventive compound is included in at least one of the layers (hole injection layer, hole transport layer, electron blocking layer, etc.) selected from those constituting the hole transport region, and more preferably, the inventive compound is included in the hole transport layer.

[1133] The hole injection layer formed adjacent to the anode is formed using a material that is easy to inject holes into regardless of the work function of the anode. Therefore, materials commonly used as electrode materials (e.g., metals, alloys, conductive compounds and mixtures thereof, elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[1134] Elements belonging to Group 1 or Group 2 of the periodic table that have low work functions can also be used, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them. It should be noted that when using alkali metals, alkaline earth metals, and their alloys to form the anode, vacuum evaporation or sputtering methods can be used. Furthermore, when using silver paste, coating or inkjet printing methods can be used.

[1135] Hole injection layer

[1136] A hole injection layer is a layer containing a material with high hole injection properties (hole injection material), which is formed between the anode and the light-emitting layer, or between the hole transport layer and the anode in the presence of a hole transport layer.

[1137] Other than the inventive compound, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc., can be used as hole-injecting materials.

[1138] Examples of hole injection layer materials include 4,4',4''-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), and 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (DN). Aromatic amine compounds such as TPD, 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) are also mentioned.

[1139] Polymers (oligomers, dendritic polymers, polymers, etc.) can also be used. Examples include: poly(N-vinylcarbazole) (PVK), poly(4-vinyltriphenylamine) (PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (Poly-TPD). Additionally, polymers containing acids, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[1140] In addition, acceptor materials such as hexaazabenzophenanthrene (HAT) compounds represented by the following formula (K) are also preferred.

[1141]

Chemical Formula 215

[1142]

[1143] (In the above formula, R) 221 ~R 226 Each can independently represent a cyano group, -CONH2, a carboxyl group, or -COOR. 227 (R 227 (Refers to alkyl groups having 1 to 20 carbon atoms or cycloalkyl groups having 3 to 20 carbon atoms). Additionally, it is selected from R... 221 and R 222 R 223 and R 224 and R 225 and R 226 Two adjacent groups can bond with each other to form a group represented by -CO-O-CO-.

[1144] As R 227 Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, and cyclohexyl.

[1145] In one embodiment of the organic EL element of the present invention, the hole transport region includes a hole injection layer located between the anode and the first hole transport layer on the anode side. The hole injection layer includes a first organic material and a second organic material, wherein the first organic material and the second organic material are different from each other. The content of the second organic material in the hole injection layer is 0.01% by mass or more and less than 50% by mass, preferably 0.05% by mass or more and 30% by mass or less, more preferably 0.10% by mass or more and 10% by mass or less, further preferably 0.50% by mass or more and 5% by mass or less, and particularly preferably 1.0% by mass or more and 3% by mass or less.

[1146] Examples of the first organic material include the inventive compound or other hole-injecting materials mentioned above.

[1147] In one embodiment of the organic EL element, the second organic material is a compound comprising at least one of the first ring structure shown in the following general formula (P11) and the second ring structure shown in the following general formula (P12).

[1148]

Chemical Formula 216

[1149]

[1150] (The first ring structure shown in the above general formula (P11) is fused in the molecule of the above second organic material with at least one ring structure among the substituted or unsubstituted aromatic hydrocarbon ring with 6 to 50 carbon atoms and the substituted or unsubstituted heterocyclic ring with 5 to 50 atoms.)

[1151] =Z 10 The structures shown are represented by the following general formulas (11a), (11b), (11c), (11d), (11e), (11f), (11g), (11h), (11i), (11j), (11k), or (11m).

[1152]

Chemical Formula 217

[1153]

[1154]

Chemical Formula 218

[1155]

[1156] (In the above general formulas (11a), (11b), (11c), (11d), (11e), (11f), (11g), (11h), (11i), (11j), (11k) or (11m), R 11 ~R 14 and R1101 ~R 1110 Each independently

[1157] hydrogen atom,

[1158] Halogen atoms,

[1159] hydroxyl,

[1160] cyano,

[1161] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1162] Substituted or unsubstituted alkyl halides with 1 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] -N(R 906 (R) 907 The groups shown in the figure,

[1168] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms or

[1169] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1170] (In the above general formula (P12), Z1 to Z5 are each independently...)

[1171] nitrogen atoms,

[1172] With R 15 Bonded carbon atoms, or

[1173] Carbon atoms bonded to other atoms in the molecule of the second organic material mentioned above,

[1174] At least one of Z1 to Z5 is a carbon atom bonded to other atoms in the molecule of the second organic material mentioned above.

[1175] R 15 Freedom of choice

[1176] hydrogen atom,

[1177] Halogen atoms,

[1178] cyano,

[1179] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1180] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[1181] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1182] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms

[1183] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms

[1184] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1185] -O-(R 904 The groups shown in the figure,

[1186] -S-(R 905 The groups shown in the figure,

[1187] -N(R 906 (R) 907 The groups shown in the figure,

[1188] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1189] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[1190] carboxyl,

[1191] Substituted or unsubstituted ester groups

[1192] Substituted or unsubstituted carbamoyl group,

[1193] Nitro, and

[1194] The group consisting of substituted or unsubstituted siloxanyl groups.

[1195] In R 15 In the case of multiple Rs, multiple Rs 15 (They may be the same or different.)

[1196] (In the second organic material mentioned above, R) 901 ~R 907 Each independently

[1197] hydrogen atom,

[1198] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1199] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1200] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1201] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1202] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.

[1203] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.

[1204] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.

[1205] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.

[1206] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.

[1207] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.

[1208] In R 907 In the case of multiple Rs, multiple Rs 907 (They may be the same or different.)

[1209] In this specification, the ester group is selected from at least one group chosen from the group consisting of alkyl ester groups and aryl ester groups.

[1210] The alkyl ester group in this specification is, for example, represented by -C(=O)OR E Indicates. R E For example, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms (preferably 1 to 10 carbon atoms).

[1211] The aryl ester group in this specification is, for example, represented by -C(=O)OR Ar Indicates. R Ar For example, aryl groups with 6 to 30 carbon atoms, whether substituted or unsubstituted.

[1212] In this specification, siloxane refers to a silicon compound group via an ether bond, such as trimethylsiloxane.

[1213] In this specification, the carbamoyl group is represented by -CONH2.

[1214] The substituted carbamoyl group in this specification is, for example, derived from -CONH-Ar C , or -CONH-R C Ar indicates. C For example, it can be at least one group selected from the group consisting of an aryl group with 6 to 50 (preferably 6 to 10) cyclic carbon atoms (either substituted or unsubstituted) and a heterocyclic group with 5 to 50 (preferably 5 to 14) cyclic atoms. C It can be a group formed by bonding a substituted or unsubstituted aryl group with 6 to 50 carbon atoms to a substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms.

[1215] R C For example, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms (preferably 1 to 6 carbon atoms).

[1216] In the second organic material described above, it is preferred that the groups described as "substituted or unsubstituted" are all "unsubstituted" groups.

[1217] Examples of second organic materials include the following compounds. However, the present invention is not limited to specific examples of these second organic materials.

[1218]

Chemical Formula 219

[1219]

[1220]

Chemical Formula 220

[1221]

[1222] Hole transport layer

[1223] A hole transport layer is a layer containing a material with high hole transportability (hole transport material) formed between the anode and the light-emitting layer, or between the hole injection layer and the light-emitting layer in the presence of a hole injection layer. The inventive compound can be used alone or in combination with the compounds described below for use in the hole transport layer.

[1224] The hole transport layer can be a single-layer structure or a multi-layer structure containing two or more layers. For example, the hole transport layer can be a two-layer structure comprising a first hole transport layer (anode side) and a second hole transport layer (cathode side). That is, the aforementioned hole transport region can include a first hole transport layer on the anode side and a second hole transport layer on the cathode side. Alternatively, the hole transport layer can be a three-layer structure comprising a first hole transport layer, a second hole transport layer, and a third hole transport layer sequentially from the anode side. That is, a third hole transport layer can be disposed between the second hole transport layer and the light-emitting layer.

[1225] In one aspect of the present invention, the hole transport layer of the single-layer structure is preferably adjacent to the light-emitting layer. Furthermore, it is preferable that the hole transport layer closest to the cathode in the multilayer structure, such as the second hole transport layer in the two-layer structure or the third hole transport layer in the three-layer structure, is adjacent to the light-emitting layer. Particularly preferred is that the light-emitting layer and the second hole transport layer are directly connected. In another aspect of the present invention, an electron blocking layer, as described later, may be sandwiched between the hole transport layer and the light-emitting layer in the single-layer structure, or between the hole transport layer closest to the light-emitting layer in the multilayer structure. Additionally, as described above, when the hole transport layer is a multilayer structure containing two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer in the multilayer structure can also be used as an electron blocking layer.

[1226] In one embodiment of the organic electroluminescent device of the present invention, at least one of the first hole transport layer and the second hole transport layer comprises the inventive compound. Specifically, in the two-layer hole transport layer structure, the inventive compound may be contained in one or both of the first and second hole transport layers. In another embodiment, at least one of the first to third hole transport layers comprises the inventive compound. Specifically, in the three-layer hole transport layer structure, the inventive compound may be contained in only one of the first to third hole transport layers, only in any two layers, or in all layers.

[1227] In one aspect of the present invention, it is preferred that the inventive compound is contained in the second hole transport layer. More specifically, it is preferred that the inventive compound is contained only in the second hole transport layer, or that the inventive compound is contained in both the first hole transport layer and the second hole transport layer.

[1228] Other hole transport layer materials besides the inventive compound can be, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc.

[1229] Examples of aromatic amine compounds include: 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BAFLP), and 4,4'-bis[N-(9,9-dimethyl]... [fluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as DFLDPBi), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (abbreviated as TDATA), 4,4',4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as MTDATA), and 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB). The above compounds have 10 -6 cm 2 Hole mobility above / Vs.

[1230] Examples of carbazole derivatives include 4,4'-bis(9-carbazolyl)biphenyl (CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (PCzPA).

[1231] Examples of anthracene derivatives include 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (abbreviated as t-BuDNA), 9,10-bis(2-naphthyl)anthracene (abbreviated as DNA), and 9,10-diphenylanthracene (abbreviated as DPAnnth).

[1232] Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) can also be used.

[1233] Among them, any compound whose hole transport capability is higher than its electron transport capability can use compounds other than those mentioned above.

[1234] In one embodiment of the organic EL element involved in this invention, the first hole transport layer comprises a compound represented by formula (21) or formula (22).

[1235]

Chemical Formula 221

[1236]

[1237] In equations (21) and (22) above,

[1238] L A1 L B1 LC1 L A2 L B2 L C2 and L D2 Each is independently a single bond, a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in the cyclic ring, or a divalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms.

[1239] k can be 1, 2, 3, or 4.

[1240] When k is 1, L E2 It is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in the cyclic ring, or a substituted or unsubstituted divalent heterocyclic group with 5 to 50 carbon atoms in the cyclic ring.

[1241] When k is 2, 3, or 4, multiple L E2 They are the same or different.

[1242] When k is 2, 3, or 4, multiple L E2 They can bond together to form substituted or unsubstituted monocyclic rings, bond together to form substituted or unsubstituted fused rings, or not bond together at all.

[1243] L does not form the aforementioned single ring and does not form the aforementioned fused ring E2 It is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in the cyclic ring, or a substituted or unsubstituted divalent heterocyclic group with 5 to 50 carbon atoms in the cyclic ring.

[1244] A 1 B 1 C 1 A 2 B 2 C 2 and D 2 Each is independently a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group with 5 to 50 cyclic atoms, or a -Si(R') group. 901 )(R' 902 )(R' 903 ),

[1245] R' 901 、R' 902 and R' 903 Each is independently a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic formation.

[1246] In R' 901 In the case of multiple R's, multiple R's 901 They are the same or different.

[1247] In R' 902 In the case of multiple R's, multiple R's 902They are the same or different.

[1248] In R' 903 In the case of multiple R's, multiple R's 903 They are the same or different.

[1249] It should be noted that the first hole transport layer described above may contain one compound represented by formula (21) and formula (22), or it may contain multiple compounds represented by formula (21) and formula (22).

[1250] In equations (21) and (22), it is preferred that A 1 B 1 C 1 A 2 B 2 C 2 and D 2 Each is independently selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl and substituted or unsubstituted carbazoleyl.

[1251] Furthermore, more preferably, the part selected from A in formula (21) is... 1 B 1 and C 1 At least one of them, and the ones selected from A in equation (22) 2 B 2 C 2 and D 2 At least one of them is a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiopheneyl, or a substituted or unsubstituted carbazoyl.

[1252] A 1 B 1 C 1 A 2 B 2 C 2 and D 2 The optional fluorenyl group may have a substituent at the 9-position, such as 9,9-dimethylfluorenyl or 9,9-diphenylfluorenyl. Alternatively, the substituents at the 9-position may form a ring with each other, for example, a fluorenyl skeleton or a thallium skeleton may be formed by the substituents at the 9-position.

[1253] L A1 L B1 L C1 L A2 L B2 LC2 and L D2 Preferably, each arylene group is a single bond, substituted or unsubstituted, and has 6 to 12 carbon atoms in the cyclic group.

[1254] As specific examples of the compounds shown in formulas (21) and (22), the following compounds can be cited.

[1255]

Chemical Formula 222

[1256]

[1257] dopant material of the light-emitting layer

[1258] The luminescent layer is a layer containing a highly luminescent material (dopant material), and various materials can be used. For example, fluorescent luminescent materials and phosphorescent luminescent materials can be used as dopant materials. Fluorescent luminescent materials are compounds that emit light using a singlet excited state, while phosphorescent luminescent materials are compounds that emit light using a triplet excited state.

[1259] In one embodiment of the organic EL element involved in this invention, it is preferred that the light-emitting layer is a single layer.

[1260] In addition, in one embodiment of the organic EL element of the present invention, it is preferred that the light-emitting layer is composed of multiple layers stacked together.

[1261] As blue fluorescent materials that can be used in the luminescent layer, pyrene derivatives, styrylamine derivatives, phenanthrene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, azaborane derivatives, and arylborane derivatives can be used. Specifically, examples include N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenyl sphine-4,4'-diamine (abbreviated as YGA2S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthrayl)triphenylamine (abbreviated as YGAPA), and 4-(10-phenyl-9-anthrayl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCPA).

[1262] As green fluorescent materials that can be used in the luminescent layer, aromatic amine derivatives can be used. Specifically, examples include N-(9,10-diphenyl-2-anthrayl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthrayl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCABPhA), and N-(9,10-diphenyl-2-anthrayl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPA). PA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthrayl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviated as: 2YGABPhA), N,N,9-triphenylanthracene-9-amine (abbreviated as: DPhAPhA), etc.

[1263] As red-based fluorescent materials that can be used in the luminescent layer, tetraphenyl derivatives, diamine derivatives, etc., can be used. Specifically, examples include N,N,N',N'-tetra(4-methylphenyl)tetraphenyl-5,11-diamine (abbreviated as p-mPhTD) and 7,14-diphenyl-N,N,N',N'-tetra(4-methylphenyl)acenaphthene[1,2-a]fluoranthene-3,10-diamine (abbreviated as p-mPhAFD).

[1264] In one embodiment of the present invention, the light-emitting layer preferably comprises a fluorescent light-emitting material (fluorescent dopant material).

[1265] As blue phosphorescent materials that can be used in the luminescent layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes can be used. Specifically, examples include bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)tetra(1-pyrazolyl)borate (abbreviated as Fir6), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)pyridinecarboxylate (abbreviated as Firpic), bis[2-(3',5'-bistrifluoromethylphenyl)pyridine-N,C2']iridium(III)pyridinecarboxylate (abbreviated as Ir(CF3ppy)2(pic)), and bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)acetylacetone (abbreviated as Firacac).

[1266] As a green phosphorescent material that can be used in the luminescent layer, iridium complexes can be used. Examples include tris(2-phenylpyridine-N,C2')iridium(III) (abbreviated as Ir(ppy)3), bis(2-phenylpyridine-N,C2')iridium(III)acetylacetonate (abbreviated as Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazole)iridium(III)acetylacetonate (abbreviated as Ir(pbi)2(acac)), and bis(benzo[h]quinoline)iridium(III)acetylacetonate (abbreviated as Ir(bzq)2(acac)).

[1267] As red phosphorescent materials that can be used in the luminescent layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes can be used. Specifically, organometallic complexes such as bis[2-(2'-benzo[4,5-α]thienyl)pyridine-N,C3']iridium(III)acetylacetonate (abbreviated as Ir(btp)2(acac)), bis(1-phenylisoquinoline-N,C2')iridium(III)acetylacetonate (abbreviated as Ir(piq)2(acac)), (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviated as Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as PtOEP) can be used.

[1268] In addition, rare earth metal complexes such as tri(acetylacetonyl)(monophenanthrene)terbium(III) (abbreviated as Tb(acac)3(Phen)), tri(1,3-diphenyl-1,3-propanedione)(monophenanthrene)eupium(III) (abbreviated as Eu(DBM)3(Phen)), and tri[1-(2-thiophenecarboxyl)-3,3,3-trifluoroacetone](monophenanthrene)eupium(III) (abbreviated as Eu(TTA)3(Phen)) can be used as phosphorescent materials because their luminescence originates from the luminescence of rare earth metal ions (electronic transitions between different multiplicity levels).

[1269] The main material of the light-emitting layer

[1270] The light-emitting layer can be configured by dispersing the aforementioned dopant material within other materials (the host material). Preferably, a material with a lower unoccupied orbital level (LUMO level) higher than that of the dopant material and a higher occupied orbital level (HOMO level) lower than that of the dopant material is used.

[1271] As the main material, use, for example

[1272] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes;

[1273] (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives;

[1274] (3) Carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or pyroxene derivatives, etc., fused aromatic compounds

[1275] (4) Aromatic amine compounds such as triarylamine derivatives or fused polycyclic aromatic amine derivatives.

[1276] In this invention, as an option, it is preferred that the light-emitting layer comprises anthracene derivative, wherein at least one hydrogen atom on a benzene ring of the anthracene derivative is deuterated.

[1277] Specific examples of anthracene derivatives are described below.

[1278] For example, metal complexes such as tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-hydroxyquinoline)aluminum(III) (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium(II) (abbreviated as BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO), and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ) can be used;

[1279] Heterocyclic compounds such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2',2''-(1,3,5-phenyltriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), phenanthroline (abbreviation: BPhen), and copper bath (abbreviation: BCP);

[1280] 9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-bis(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (abbreviation: t-BuDN) A) fused aromatic compounds such as 9,9'-bianthracite (BANT), 9,9'-(bruhn-3,3'-diyl)diphenanthrene (DPNS), 9,9'-(bruhn-4,4'-diyl)diphenanthrene (DPNS2), 3,3',3''-(benzene-1,3,5-triyl)tripyrene (TPB3), 9,10-diphenylanthracene (DPAnth), and 6,12-dimethoxy-5,11-diphenylanthracene; and,

[1281] N,N-Diphenyl-9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthrayl)triphenylamine (abbreviation: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthrayl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthrayl)-N,9-diphenyl- Aromatic amine compounds such as 9H-carbazole-3-amine (abbreviated as 2PCAPA), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as DFLDPBi), and 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB) can be used as the main material.

[1282] In particular, in the case of blue fluorescent elements, the following anthracene derivatives are preferred as the host material.

[1283]

Chemical Formula 223

[1284]

[1285] [Chemical Formula 224]

[1286]

[1287] [Chemical Formula 225]

[1288]

[1289]

Chemical Formula 226

[1290]

[1291] In one embodiment of the organic EL element of the present invention, it is preferred that the light-emitting layer is formed by stacking multiple layers. When the light-emitting layer is formed by stacking multiple layers, for example, including a first light-emitting layer and a second light-emitting layer, at least one component constituting the first light-emitting layer is different from the component constituting the second light-emitting layer. For example, embodiments in which the dopant material contained in the first light-emitting layer is different from the dopant material contained in the second light-emitting layer, or embodiments in which the host material contained in the first light-emitting layer is different from the host material contained in the second light-emitting layer, can be cited.

[1292] In the organic EL element involved in this embodiment, the light-emitting layer may contain a luminescent compound that exhibits fluorescence emission with a main peak wavelength of less than 500 nm.

[1293] The method for determining the peak wavelength of the main peak of the compound is as follows. A 5 μmol / L toluene solution of the compound to be measured is prepared and added to a quartz cuvette. The emission spectrum of the sample is measured at room temperature (300 K) (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 spectroscopy measuring device is not limited to the device used here.

[1294] In the emission spectrum, the peak wavelength at which the emission intensity reaches its maximum is defined as the main peak wavelength. It should be noted that, in this specification, the main peak wavelength is sometimes referred to as the fluorescence emission main peak wavelength (FL-peak).

[1295] The luminescent compound exhibiting fluorescence with a main peak wavelength below 500 nm can be either the dopant material or the host material mentioned above.

[1296] When the luminescent layer is a single layer, either the dopant material or the host material can be a luminescent compound exhibiting fluorescence with a main peak wavelength below 500 nm, or both materials can be luminescent compounds exhibiting fluorescence with a main peak wavelength below 500 nm.

[1297] Furthermore, when the luminescent layer comprises a first luminescent layer and a second luminescent layer, only one of the first and second luminescent layers may contain a luminescent compound exhibiting fluorescence with a main peak wavelength of 500 nm or less, or both luminescent layers may contain a luminescent compound exhibiting fluorescence with a main peak wavelength of 500 nm or less. Moreover, when the first luminescent layer contains a luminescent compound exhibiting fluorescence with a main peak wavelength of 500 nm or less, only one of the dopant material and the host material contained in the first luminescent layer may be a luminescent compound exhibiting fluorescence with a main peak wavelength of 500 nm or less, or both materials may be luminescent compounds exhibiting fluorescence with a main peak wavelength of 500 nm or less. Alternatively, if the second luminescent layer contains a luminescent compound that exhibits fluorescence emission with a main peak wavelength of less than 500 nm, either the dopant material or the host material contained in the second luminescent layer may be a luminescent compound that exhibits fluorescence emission with a main peak wavelength of less than 500 nm, or both materials may be luminescent compounds that exhibit fluorescence emission with a main peak wavelength of less than 500 nm.

[1298] Electron transport layer

[1299] An electron transport layer is a layer containing a material with high electron transport properties (electron transport material), which is formed between the light-emitting layer and the cathode, or between the electron injection layer and the light-emitting layer in the presence of an electron injection layer.

[1300] The electron transport layer can be a single-layer structure or a multi-layer structure containing two or more layers. For example, the electron transport layer can be a two-layer structure containing a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one aspect of the invention, the electron transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, or the electron transport layer closest to the anode in the multi-layer structure, such as the first electron transport layer in the two-layer structure, is preferably adjacent to the light-emitting layer. In another aspect of the invention, a hole-blocking layer, as described later, may be sandwiched between the electron transport layer and the light-emitting layer in the single-layer structure, or between the electron transport layer closest to the light-emitting layer in the multi-layer structure.

[1301] For example, an electron transport layer can be used

[1302] (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes;

[1303] (2) Imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives, and other heteroaromatic compounds.

[1304] (3) Polymer compounds.

[1305] Examples of metal complexes include: tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-hydroxyquinoline)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (abbreviated as BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO), bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ), and (8-hydroxyquinoline)lithium (abbreviated as Liq).

[1306] Examples of heteroaromatic compounds include: 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviated as p-EtTAZ), phenanthroline (abbreviated as BPhen), copper hydroxide (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)zirconia (abbreviated as BzOs).

[1307] Examples of high molecular weight compounds include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy).

[1308] The above material has 10 -6 cm 2 Materials with an electron mobility of / Vs or higher. It should be noted that any material with electron transport capacity higher than hole transport capacity can be used for the electron transport layer, even if it is not mentioned above. Furthermore, the electron transport layer can be a single layer or a stack of two or more layers, each containing the aforementioned materials. When the electron transport layer is a two-layer structure, the layer on the anode side is called the first electron transport layer, and the layer on the cathode side is called the second electron transport layer.

[1309] Electron injection layer

[1310] An electron injection layer is a layer containing materials with high electron injection capability. The electron injection layer can use alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), rare earth metals such as europium (Eu) and ytterbium (Yb), and compounds containing these metals. Examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes such as (8-hydroxyquinoline)lithium (Liq), alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, rare earth metal oxides, rare earth metal halides, and rare earth metal-containing organic complexes. Furthermore, multiple such compounds can be used in combination.

[1311] Furthermore, materials containing alkali metals, alkaline earth metals, or their compounds in an electron-transporting material can be used; specifically, materials containing magnesium (Mg) in Alq can be used. It should be noted that electron injection from the cathode can be performed more efficiently in this case.

[1312] Alternatively, the electron injection layer can be a composite material made by mixing an organic compound and an electron donor. Such a composite material exhibits excellent electron injection and electron transport properties because the organic compound accepts electrons from the electron donor. In this case, the organic compound is preferably a material that excels in the transport of the accepted electrons; specifically, materials constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) as described above can be used. The electron donor can be any material that exhibits electron-donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Additionally, alkali metal oxides and alkaline earth metal oxides are preferred, such as lithium oxides, calcium oxides, and barium oxides. Furthermore, Lewis bases such as magnesium oxide can also be used. Additionally, organic compounds such as tetrathiofulvalene (TTF) can also be used.

[1313] cathode

[1314] The cathode preferably uses metals, alloys, conductive compounds, and mixtures thereof with low work functions (specifically below 3.8 eV). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr) and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb) and alloys containing them.

[1315] It should be noted that when using alkali metals, alkaline earth metals, or alloys containing them to form the cathode, vacuum evaporation or sputtering methods can be used. Additionally, when using silver paste, coating or inkjet printing methods can be used.

[1316] It should be noted that by setting an electron injection layer, a wide variety of conductive materials, such as Al, Ag, ITO, graphene, and indium tin oxide containing silicon or silicon oxide, can be used to form cathodes regardless of the work function. These conductive materials can be deposited using methods such as sputtering, inkjet printing, and spin coating.

[1317] Insulation layer

[1318] Organic EL elements are prone to pixel defects due to leakage and short circuits because an electric field is applied to the ultrathin film. To prevent this, an insulating layer formed by an insulating thin film can be inserted between a pair of electrodes.

[1319] Examples of materials that can be used as insulating layers include alumina, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide. It should be noted that mixtures or laminates of these materials can also be used.

[1320] Spacer layer

[1321] In the case of a stacked fluorescent and phosphorescent layer, the spacer layer refers to a layer disposed between the fluorescent and phosphorescent layers to prevent excitons generated in the phosphorescent layer from diffusing to the fluorescent layer or to adjust carrier balance. Alternatively, the spacer layer may be disposed between multiple phosphorescent layers.

[1322] Since the spacer layer is disposed between the light-emitting layers, it is preferably made of a material that has both electron transport and hole transport properties. Furthermore, to prevent the diffusion of triplet energy within adjacent phosphorescent light-emitting layers, the triplet energy is preferably 2.6 eV or higher. Materials similar to those used for the hole transport layer can be used as examples of materials for the spacer layer.

[1323] Barrier layer

[1324] Electron blocking layers, hole blocking layers, exciton blocking layers, and other blocking layers can also be placed adjacent to the light-emitting layer. An electron blocking layer prevents electrons from leaking from the light-emitting layer to the hole transport layer, while a hole blocking layer prevents holes from leaking from the light-emitting layer to the electron transport layer. An exciton blocking layer prevents excitons generated in the light-emitting layer from diffusing to surrounding layers, thus confining the excitons within the light-emitting layer.

[1325] The layers of the aforementioned organic EL element can be formed using conventional vapor deposition or coating methods. For example, they can be formed using vapor deposition methods such as vacuum vapor deposition or molecular beam vapor deposition (MBE), or using known coating methods based on solutions of the compound forming the layer, such as dip coating, spin coating, casting, rod coating, and roll coating.

[1326] There are no particular restrictions on the thickness of each layer. Generally speaking, if the film thickness is too thin, defects such as pinholes are likely to occur. Conversely, if the film thickness is too thick, a high driving voltage is required and the efficiency will be reduced. Therefore, the thickness is usually 5nm to 10μm, and more preferably 10nm to 0.2μm.

[1327] In one embodiment of the organic EL element of the present invention, the combined thickness of the first hole transport layer and the second hole transport layer is 30 nm or more and 150 nm or less. In this case, it is preferably 40 nm or more and 130 nm or less.

[1328] Furthermore, in one embodiment of the organic EL element of the present invention, the thickness of the second hole transport layer is 20 nm or more. Preferably, it is 25 nm or more, more preferably 35 nm or more, and further preferably 100 nm or less.

[1329] Furthermore, in one embodiment of the organic EL element of the present invention, the hole transport layer adjacent to the light-emitting layer is 20 nm or more. Preferably, it is 25 nm or more, more preferably 30 nm or more, and further preferably 100 nm or less.

[1330] Furthermore, in one embodiment of the organic EL element of the present invention, the film thickness D1 of the first hole transport layer and the film thickness D2 of the second hole transport layer satisfy the relationship 0.3 < D2 / D1 < 4.0. Preferably, the relationship is 0.5 < D2 / D1 < 3.5, and more preferably, the relationship is 0.75 < D2 / D1 < 3.0.

[1331] Examples of embodiments of the organic EL element of the present invention include:

[1332] As an organic EL element having the hole transport layer composed of the above two layers and

[1333] • A first embodiment in which the second hole transport layer contains the compound of the present invention and the first hole transport layer does not contain the compound of the present invention;

[1334] The first hole transport layer and the second hole transport layer both comprise the second embodiment of the compound of the present invention;

[1335] • A third embodiment in which the first hole transport layer contains the compound of the present invention and the second hole transport layer does not contain the compound of the present invention;

[1336] As an organic EL element having a hole transport layer consisting of the above three layers and

[1337] A fourth embodiment in which the first hole transport layer contains the compound of the present invention and the second and third hole transport layers do not contain the compound of the present invention;

[1338] A fifth embodiment in which the second hole transport layer contains the compound of the present invention and the first and third hole transport layers do not contain the compound of the present invention;

[1339] A sixth embodiment in which the third hole transport layer contains the compound of the present invention and the first and second hole transport layers do not contain the compound of the present invention;

[1340] • A seventh embodiment in which the first and second hole transport layers contain the compounds of the present invention and the third hole transport layer does not contain the compounds of the present invention;

[1341] • An eighth embodiment in which the first and third hole transport layers contain the compounds of the present invention and the second hole transport layer does not contain the compounds of the present invention;

[1342] • A ninth embodiment in which the second and third hole transport layers contain the compounds of the present invention and the first hole transport layer does not contain the compounds of the present invention;

[1343] • The first to third hole transport layers all contain the compound of the present invention in the tenth embodiment; etc.

[1344] electronic devices

[1345] The aforementioned organic EL elements can be used in display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, as well as electronic devices such as lighting and vehicle lamps.

[1346] Example

[1347] The present invention will be described in more detail below using examples, but the present invention is not limited to the following examples.

[1348] The inventive compounds used in the manufacture of the organic EL elements in Examples 1-9

[1349] [Chemical Formula 227]

[1350]

[1351] [Chemical Formula 228]

[1352]

[1353] [Chemical Formula 229]

[1354]

[1355] The comparative compounds used in the manufacture of organic EL elements in Comparative Examples 1 and 2

[1356]

Chemical Formula 230

[1357]

[1358] Other compounds used in the manufacture of organic EL elements in Examples 1-9 and Comparative Examples 1-2

[1359]

Chemical Formula 231

[1360]

[1361] Fabrication of organic EL components

[1362] Example 1

[1363] A 25mm × 75mm × 1.1mm glass substrate (manufactured by Geomatec Corporation) with an ITO transparent electrode (anode) was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was set to 130nm.

[1364] The cleaned glass substrate with the ITO transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, compound HT-1 and compound HA were co-deposited on the side where the transparent electrode was formed, covering the transparent electrode, to form a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-1 to compound HA (HT-1:HA) was 97:3.

[1365] Next, compound HT-1 was deposited on the hole injection layer to form the first hole transport layer with a thickness of 85 nm.

[1366] Next, compound HT-2 (compound 1) was deposited on the first hole transport layer to form a second hole transport layer with a film thickness of 5 nm.

[1367] Next, compounds BH-1 (the host material) and BD-1 (the dopant material) were co-deposited on the second hole transport layer to form a light-emitting layer with a thickness of 20 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 99:1.

[1368] Next, compound ET-1 was deposited on the light-emitting layer to form a first electron transport layer with a thickness of 5 nm.

[1369] Next, compounds ET-2 and Liq were co-deposited on the first electron transport layer to form a second electron transport layer with a thickness of 31 nm. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50.

[1370] Next, Liq was deposited on the second electron transport layer to form an electron injection electrode with a film thickness of 1 nm.

[1371] Then, metallic Al was deposited on the electron-injecting electrode to form a metal cathode with a film thickness of 80 nm.

[1372] The following shows the layer configuration of the organic EL element of Example 1 obtained by such operation.

[1373] ITO (130) / HT-1: HA=97: 3 (10) / HT-1 (85) / HT-2 (compound 1) (5) / BH-1: BD-1=99: 1 (20) / ET-1 (5) / ET-2: Liq=50: 50 (31) / Liq (1) / Al (80)

[1374] In the above layer composition, the numbers in parentheses are film thicknesses (nm), and the ratios are mass ratios.

[1375] Examples 2 to 9

[1376] The organic EL elements of Examples 2 to 9 were prepared in the same manner as in Example 1, except that compounds 2 to 9 were used in sequence instead of compound 1.

[1377] Comparative Example 1

[1378] Organic EL elements were fabricated in the same manner as in Example 1, except that comparative compound 1 was used instead of compound 1.

[1379] Comparative Example 2

[1380] Organic EL elements were fabricated in the same manner as in Example 1, except that comparative compound 2 was used instead of compound 1.

[1381] Evaluation of organic EL devices

[1382] Determination of Component Life (LT95)

[1383] The obtained organic EL element was subjected to a current density of 50 mA / cm². 2 DC drive was applied, and the time (h: hours) during which the brightness decreased to 95% of the initial brightness was measured. This time was taken as the 95% lifetime (LT95). The 95% lifetime (LT95) of Comparative Example 1 was set to 100, and the relative values ​​(%) are shown in Table 1.

[1384] Table 1

[1385]

[1386] As can be clearly seen from the results in Table 1, the monoamines (compounds 1 to 9) that meet the requirements of this invention provide organic EL elements with significantly improved element life compared to the monoamines (comparative compound 1 and comparative compound 2) that do not meet the requirements of this invention.

[1387] The inventive compound synthesized in the synthetic example

[1388]

Chemical Formula 232

[1389]

[1390]

Chemical Formula 233

[1391]

[1392]

Chemical Formula 234

[1393]

[1394] Synthesis Example 1: Synthesis of Compound 1

[1395] [Chemical Formula 235]

[1396]

[1397] Under an argon atmosphere, a mixture of 9-(3-bromophenyl)-9H-carbazole (3.22 g, 10 mmol) (starting material 1 as described in Synthesis Example 1 of Table 2-1 below), N-([1,1'-biphenyl]-4-yl-2,3,5,6-d4)-[1,1':4',1''-terphenyl]-2,3,5,6-d4-4-amine (4.06 g, 10 mmol) (starting material 2 as described in Synthesis Example 1 of Table 2 below), tris(dibenzylideneacetone)dipalladium(0) (0.183 g, 0.2 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.232 g, 0.8 mmol), sodium tert-butoxide (1.44 g, 15 mmol), and xylene (50 mL) was refluxed at boiling point for 3 hours. After cooling the reaction solution to room temperature, it was concentrated under reduced pressure. The residue was purified by silica gel column chromatography and recrystallization to obtain 3.75 g of a white solid. The yield was 58%. Mass spectrometry analysis of the obtained substance identified it as compound 1, with a molecular weight of 646.86 and m / e = 647.

[1398] Synthesis Examples 2 to 5: Synthesis of Compounds 2 to 5

[1399] The raw materials 1 and 2 listed in Table 2-1 used in Synthesis Example 1 were changed to the raw materials 1 and 2 listed in Table 2-1 used in Synthesis Examples 2 to 5. Otherwise, compounds 2 to 5 were synthesized using the same method as in Synthesis Example 1.

[1400] Compounds 1–5 are shown together with starting materials 1 and 2 and yields in Table 2-1.

[1401] Synthesis Examples 6 to 9: Synthesis of Compounds 6 to 9

[1402] The raw materials 1 and 2 listed in Table 2-1 used in Synthesis Example 1 were changed to the raw materials 1 and 2 listed in Table 2-2 used in Synthesis Examples 6 to 9. Otherwise, compounds 6 to 9 were synthesized using the same method as in Synthesis Example 1.

[1403] Compounds 6–9, along with starting materials 1 and 2 and their yields, are shown in Table 2-2.

[1404] Table 2-1

[1405]

[1406] Table 2-2

[1407]

[1408] Symbol Explanation

[1409] 1, 11, 12 Organic EL elements

[1410] 2 substrate

[1411] 3 Anode

[1412] 4 Cathode

[1413] 5. Light-emitting layer

[1414] 6. Hole transport region (hole transport layer)

[1415] 6a Hole injection layer

[1416] 6b Hole Transport Layer 1

[1417] 6c Hole transport layer 2

[1418] 6d Third Hole Transport Layer

[1419] 7. Electron transport region (electron transport layer)

[1420] 7a First electron transport layer

[1421] 7b Second electron transport layer

[1422] 10, 20, 30 light-emitting units

Claims

1. The compound represented by formula (1) below, having at least one deuterium atom, In equation (1), N ＊ The central nitrogen atom, R 1 ~R 4 and R 11 ~R 18 Each is an independent hydrogen atom. Ar 1 It is an aryl group with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted, or a heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted. in, When a substituted or unsubstituted aryl group with 6 to 50 carbon atoms is described as "substituted or unsubstituted," the substituents are each independently a halogen, an unsubstituted alkyl group with 1 to 18 carbon atoms, an unsubstituted cycloalkyl group with 3 to 20 carbon atoms, or an unsubstituted aryl group with 6 to 18 carbon atoms, wherein the hydrogen atoms of the unsubstituted alkyl group are not deuterated. When a heterocyclic group with 5 to 50 cyclic atoms is described as "substituted or unsubstituted", the substituent is independently a halogen, an unsubstituted alkyl group with 1 to 18 carbon atoms, or an unsubstituted cycloalkyl group with 3 to 20 cyclic carbon atoms. Ar 2 Represented by the following formulas (2A), (2B), (2C), (2D), (2E), (2F), or (2G), In equation (2A), *21 indicates the relationship with L 2 The bond, Selected from R 101 ~R 105 One of them is a single bond bonded to *22, selected from R 106 ~R 110 One of them is a single bond that bonds with *23. Not the R of the single bond 101 ~R 105 and R 106 ~R 110 Each is independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms. Selected from R which is not the single bond described 101 ~R 105 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. Selected from R which is not the single bond described 106 ~R 110 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. R 111 ~R 115 Each of the following is independently composed of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms, or a substituted or unsubstituted cyclic group having 5 to 13 heteroaryl atoms. Selected from R 111 ~R 115 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. j is 0, 1, or 2, and k is 0 or 1, excluding the case where j is 2 and k is 0. When j=0 and k=0, *23 represents *21. When j=0 and k=1, *22 represents *21. When j=1 and k=0, *23 represents *22. In equation (2B), *24 indicates the relationship with L 2 The bond, Selected from R 121 ~R 128 One of them is a single bond that bonds with *25. Not the R of the single bond 121 ~R 128 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms. Selected from R which is not the single bond described 121 ~R 128 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. In equation (2C), *26 indicates the relationship with L 2 The bond, Selected from R 131 ~R 138 One of them is a single bond that bonds with *27. Not the R of the single bond 131 ~R 138 and R 139 ~R 140 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms. Selected from R which is not the single bond described 131 ~R 138 and R 139 ~R 140 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. In equation (2D), *28 indicates the relationship with L 2 The bond, X 1 For oxygen atoms, sulfur atoms, -CR a R b or -NR c , *29 and R 141 ~R 148 R 200 ~R 203 R a R b Or R c Any one of the bonds in, In *29 and R a and R b In the case of one of them being bonded, R a and R b One of them is a single bond bonded to *29 or a divalent group bonded to *29. p is 0 or 1, When p is 0, X 1 For oxygen atoms, sulfur atoms, -CR a R b or -NR c At that time, selected from R a R b R c and R 141 ~R 148 One of them is a single bond that bonds with *29. When p is 1, X 1 For -CR a R b or -NR c At that time, R 145 With R 146 R 146 With R 147 Or R 147 With R 148 One of them is a single bond bonded to *e, and the other is a single bond bonded to *f, selected from R bonds that are not bonded to *e or *f. 145 ~R 148 R 141 ~R 144 R 200 ~R 203 R a R b and R c One of them is a single bond that bonds with *29. When p is 1, X 1 When R is an oxygen atom or a sulfur atom 145 With R 146 R 146 With R 147 Or R 147 With R 148 One of them is a single bond bonded to *e, and the other is a single bond bonded to *f, selected from R bonds that are not bonded to *e or *f. 145 ~R 148 R 141 ~R 144 and R 200 ~R 203 One of them is a single bond that bonds with *29. Not the R of the single bond 141 ~R 148 R is not the single bond mentioned above. 200 ~R 203 R is neither the single bond nor the divalent group. a and R b and R c Each of the following is independently composed of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms, or a substituted or unsubstituted cyclic group having 5 to 13 heteroaryl atoms. Among them, R a and R b The unsubstituted alkyl group indicates that its hydrogen atoms are not deuterated. Selected from R which is not the single bond described 141 ~R 148 And R which is not the single bond 200 ~R 203 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. In equation (2E), *30 indicates the relationship with L 2 The bond, Selected from R 151 ~R 155 One of them is a single bond bonded to *31, selected from R 151 ~R 155 The other one is a single bond that bonds with *32. Not the R of the single bond 151 ~R 155 Each is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group. Selected from R which is not the single bond described 151 ~R 155 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. R 161 ~R 165 and R 171 ~R 175 Each is independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms. Selected from R which is not a hydrogen atom 161 ~R 165 At least one pair of adjacent two atoms in the form of a benzene ring are bonded to each other to form one or more unsubstituted benzene rings, or they are not bonded to each other and do not form a ring. Selected from R which is not a hydrogen atom 171 ~R 175 At least one pair of adjacent two atoms in the form are bonded to each other to form one or more unsubstituted benzene rings, or they are not bonded to each other and therefore do not form a ring. In equation (2F), *33 indicates the relationship with L 2 The bond, Selected from R 181 ~R 192 One of them is a single bond that bonds with *34. Not the R of the single bond 181 ~R 192 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms. Selected from R which is not the single bond described 181 ~R 192 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. In equation (2G), *35 indicates the relationship with L 2 The bond, R 301 ~R 308 Each of the following is independently composed of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms, or a substituted or unsubstituted cyclic group having 5 to 13 heteroaryl atoms. Selected from R 301 ~R 308 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. L 1 and L 2 Each is an arylene group that is independently either a single bond or substituted or unsubstituted, consisting of 6 to 30 carbon atoms in a cyclic structure. Among them, R selected from the A of the benzene ring 1 ~R 4 The group of hydrogen atoms represented by L 1 The hydrogen atom group represented by the unsubstituted benzene ring directly bonded to the central nitrogen atom in the arylene group, or the hydrogen atom group represented by the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, and L 2 The hydrogen atoms in at least one of the hydrogen atom groups of the unsubstituted benzene ring directly connected to the central nitrogen atom in the arylene group, or the unsubstituted fused benzene ring directly connected to the central nitrogen atom, are deuterated. In L 1 When it is a single bond, it is selected from L. 2 The hydrogen atom group represented by the unsubstituted benzene ring directly bonded to the central nitrogen atom in the arylene group, or the hydrogen atom group represented by the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, and Ar 1 The hydrogen atom group of the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aryl group, or the hydrogen atom group of the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, and Ar 1 The hydrogen atom group of the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the heterocyclic group, and the R on benzene ring A. 1 ~R 4 At least one hydrogen atom in the indicated hydrogen atom group is deuterated. In L 2 When it is a single bond, it is selected from L. 1 The hydrogen atom group represented by the unsubstituted benzene ring directly bonded to the central nitrogen atom in the arylene group, or the hydrogen atom group represented by the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, and Ar 2 The hydrogen atom group of the unsubstituted benzene ring directly attached to the central nitrogen atom in the aryl group of formulas (2A) to (2G), or the hydrogen atom group of the unsubstituted fused benzene ring directly attached to the central nitrogen atom, and Ar 2 The hydrogen atom groups of the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the heterocyclic group represented in formulas (2A) to (2G), and the R on benzene ring A 1 ~R 4 At least one hydrogen atom in the indicated hydrogen atom group is deuterated. In L 1 and L 2 When it is a single bond, it is selected from Ar 1 The hydrogen atom group of the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aryl group, or the hydrogen atom group of the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, and Ar 1 The hydrogen atom group and Ar atom group of the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the heterocyclic group are indicated. 2 The hydrogen atom group of the unsubstituted benzene ring directly attached to the central nitrogen atom in the aryl group of formulas (2A) to (2G), or the hydrogen atom group of the unsubstituted fused benzene ring directly attached to the central nitrogen atom, and Ar 2 The hydrogen atom groups of the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the heterocyclic group represented in formulas (2A) to (2G), and the R on benzene ring A 1 ~R 4 At least one hydrogen atom in the indicated hydrogen atom group is deuterated. Ar 1 With L 1 No cross-linking, and Ar 2 With L 2 It does not crosslink.

2. The compound according to claim 1, wherein, R selected from the benzene ring A directly bonded to the central nitrogen atom 1 ~R 4 The group of hydrogen atoms is represented. L 1 The hydrogen atom group represented by the unsubstituted benzene ring directly bonded to the central nitrogen atom in the arylene group, or the hydrogen atom group represented by the unsubstituted fused benzene ring directly bonded to the central nitrogen atom. L 2 The hydrogen atom group represented by the unsubstituted benzene ring directly bonded to the central nitrogen atom in the arylene group, or the hydrogen atom group represented by the unsubstituted fused benzene ring directly bonded to the central nitrogen atom. Ar 1 The hydrogen atom group represented by the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aryl group, or the hydrogen atom group represented by the unsubstituted fused benzene ring directly bonded to the central nitrogen atom. Ar 1 The group of hydrogen atoms in the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the heterocyclic group represents the group of hydrogen atoms in the heterocyclic group. Ar 2 The hydrogen atom groups of the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aryl group of formulas (2A) to (2G), or the hydrogen atom groups of the unsubstituted fused benzene ring directly bonded to the central nitrogen atom. as well as Ar 2 In the heterocyclic group represented by formulas (2A) to (2G), at least one of the hydrogen atom groups of the unsubstituted fused benzene ring directly connected to the central nitrogen atom is present. The total number of deuterated hydrogen atoms accounts for more than 65% of the total number of hydrogen atoms in the group of hydrogen atoms.

3. The compound according to claim 1 or 2, wherein, In L 1 and L 2 In the substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, the unsubstituted arylene groups are each independently selected from the group consisting of phenylene, biphenylene, naphthylene, and terphenylene.

4. The compound according to claim 1 or 2, wherein, L 1 and L 2 Each can be independently a substituted or unsubstituted meta-phenylene or a substituted or unsubstituted p-phenylene.

5. The compound according to any one of claims 1 to 4, wherein, In Ar 1 The unsubstituted or unsubstituted aryl group with 6 to 50 carbon atoms is selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl and phenanthrene.

6. The compound according to any one of claims 1 to 4, wherein, In Ar 1 The unsubstituted heterocyclic group, representing a number of 5 to 50 cyclic atoms, is selected from the group consisting of benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, and carbazole.

7. The compound according to any one of claims 1 to 6, wherein, Ar 2 It can be represented by any one of the formulas (2A) to (2G).

8. The compound according to any one of claims 1 to 6, wherein, Ar 2 It is represented by the formula (2A) or (2B).

9. The compound according to claim 1, wherein, In L 2 For substituted or unsubstituted phenylene, Ar 2 As indicated by the above formula (2D), when p is 1, *28 is interpositional or adjacent to L. 2 The substituted or unsubstituted phenylene bonds indicated, and In L 1 For substituted or unsubstituted phenylene, Ar 1 When the substituted or unsubstituted heterocyclic group with 5 to 50 cyclic atoms is a substituted or unsubstituted naphthobenzofuran group, the naphthobenzofuran group is meta- or ortho-linked with L 1 The substituted or unsubstituted phenylene bond is represented.

10. The compound according to any one of claims 1 to 8, wherein, In L 1 and L 2 In the case of substituted or unsubstituted arylene groups with 6 to 30 carbon atoms in the cyclic formation, L 1 and L 2 All hydrogen atoms in the unsubstituted benzene ring directly connected to the central nitrogen atom or in the unsubstituted fused benzene ring directly connected to the central nitrogen atom of at least one of the arylene groups are deuterated.

11. The compound according to any one of claims 1 and 3 to 8, wherein, In L 1 and L 2 In the case of a single key, Ar 1 The hydrogen atom group represented by the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aryl group, or the hydrogen atom group represented by the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, or Ar 1 The statement indicates that more than 50% of the hydrogen atoms in the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the heterocyclic group are deuterated. Ar 2 The hydrogen atom group of the unsubstituted benzene ring directly attached to the central nitrogen atom in the aryl group of formulas (2A) to (2G), or the hydrogen atom group of the unsubstituted fused benzene ring directly attached to the central nitrogen atom, or Ar 2 More than 50% of the hydrogen atoms in the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the heterocyclic group represented by formulas (2A) to (2G) are deuterated.

12. The compound according to any one of claims 1 and 3 to 8, wherein, In L 1 In the case of a single bond, Ar 1 The hydrogen atom group represented by the unsubstituted benzene ring directly bonded to the central nitrogen atom in the aryl group, or the hydrogen atom group represented by the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, or Ar 1 More than 50% of the hydrogen atoms in the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the heterocyclic group are deuterated.

13. The compound according to any one of claims 1 and 3 to 8, wherein, In L 2 In the case of a single bond, Ar 2 The hydrogen atom group of the unsubstituted benzene ring directly attached to the central nitrogen atom in the aryl group of formulas (2A) to (2G), or the hydrogen atom group of the unsubstituted fused benzene ring directly attached to the central nitrogen atom, or Ar 2 More than 50% of the hydrogen atoms in the unsubstituted fused benzene ring directly connected to the central nitrogen atom in the heterocyclic group represented by formulas (2A) to (2G) are deuterated.

14. The compound according to any one of claims 1 to 8, wherein, R on the benzene ring A directly bonded to the central nitrogen atom 1 ~R 4 The group of hydrogen atoms and L 1 The hydrogen atoms in each group of hydrogen atoms in the unsubstituted benzene ring directly connected to the central nitrogen atom in the arylene group, or in each group of hydrogen atoms in the unsubstituted fused benzene ring directly connected to the central nitrogen atom, are deuterated.

15. The compound according to any one of claims 1 to 8, wherein, R on the benzene ring A directly bonded to the central nitrogen atom 1 ~R 4 The group of hydrogen atoms and L 2 The hydrogen atoms in each group of hydrogen atoms in the unsubstituted benzene ring directly connected to the central nitrogen atom in the arylene group, or in each group of hydrogen atoms in the unsubstituted fused benzene ring directly connected to the central nitrogen atom, are deuterated.

16. The compound according to any one of claims 1 to 8, wherein, R on the benzene ring A directly bonded to the central nitrogen atom 1 ~R 4 The group of hydrogen atoms represented by L 1 The hydrogen atom group represented by the unsubstituted benzene ring directly bonded to the central nitrogen atom in the arylene group, or the hydrogen atom group represented by the unsubstituted fused benzene ring directly bonded to the central nitrogen atom, and L 2 The hydrogen atoms in the unsubstituted benzene ring directly connected to the central nitrogen atom in the arylene group, or in each group of unsubstituted fused benzene ring directly connected to the central nitrogen atom, are deuterated by more than 75%.

17. The compound according to any one of claims 1 to 8, wherein, R on the benzene ring A directly bonded to the central nitrogen atom 1 ~R 4 The hydrogen atoms in the group represented are all deuterated.

18. A material for an organic electroluminescent device comprising any one of claims 1 to 17.

19. The material for organic electroluminescent devices according to claim 18, in, The compound according to any one of claims 1 to 17 is a hole transport layer material.

20. An organic electroluminescent element having a cathode, an anode, and an organic layer located between the cathode and the anode, the organic layer being composed of a single layer or multiple layers including a light-emitting layer, wherein at least one layer selected from the group consisting of a single layer and multiple layers comprising the organic layer comprises a compound according to any one of claims 1 to 17.

21. The organic electroluminescent element according to claim 19, wherein, The organic layer includes a hole transport region located between the anode and the light-emitting layer, the hole transport region comprising any one of claims 1 to 17.

22. The organic electroluminescent element according to claim 21, wherein, The hole transport region includes a first hole transport layer on the anode side and a second hole transport layer on the cathode side. At least one of the first hole transport layer and the second hole transport layer comprises the compound according to any one of claims 1 to 17.

23. The organic electroluminescent element according to claim 22, wherein, The second hole transport layer comprises the compound according to any one of claims 1 to 17.

24. The organic electroluminescent element according to claim 21 or 22, wherein, The hole transport region includes a hole injection layer located between the anode and the first hole transport layer on the anode side. The hole injection layer comprises a first organic material and a second organic material, wherein the first organic material and the second organic material are different from each other, and the content of the second organic material in the hole injection layer is more than 0.01% by mass and less than 50% by mass.

25. The organic electroluminescent element according to any one of claims 22 to 24, wherein, The light-emitting layer is directly connected to the second hole transport layer.

26. The organic electroluminescent element according to any one of claims 22 to 25, wherein, The combined thickness of the first hole transport layer and the second hole transport layer is more than 30 nm and less than 150 nm.

27. The organic electroluminescent element according to any one of claims 20 to 26, wherein, The luminescent layer comprises a layer containing a luminescent compound exhibiting fluorescence with a main peak wavelength below 500 nm.

28. The organic electroluminescent element according to any one of claims 20 to 27, wherein, The light-emitting layer is composed of multiple layers stacked together.

29. The organic electroluminescent element according to any one of claims 20 to 28, wherein, The luminescent layer comprises an anthracene derivative, wherein at least one hydrogen atom on a benzene ring in the anthracene derivative is deuterated.

30. An electronic device comprising an organic electroluminescent element according to any one of claims 20 to 29.

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