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

Abstract

The present application relates to a compound, a material for an organic electroluminescent element, an organic electroluminescent element, and an electronic device. Provided is a compound represented by the following formula (1), a material for an organic electroluminescent element containing the compound, an organic electroluminescent element containing the aforementioned compound, and an electronic device containing such an organic electroluminescent element. The definitions of the symbols in the formula are the same as the definitions 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 1-5 disclose compounds used as materials for organic electroluminescent elements (hereinafter sometimes referred to as "materials for organic EL elements").

[0004] Existing technical documents

[0005] Patent documents

[0006] Patent Document 1: International Publication No. 2014 / 015935

[0007] Patent Document 2: Korean Patent Application Publication No. 10-2018-0042944

[0008] Patent Document 3: Description of Chinese Patent Application Publication No. 114989021

[0009] Patent Document 4: International Publication No. 2021 / 090932

[0010] Patent Document 5: International Publication No. 2020 / 226298 Summary of the Invention

[0011] The problem the invention aims to solve

[0012] 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.

[0013] The present invention was made to solve the above-mentioned problems, and aims to provide compounds that further improve the performance of organic EL elements, materials for organic electroluminescent elements that further improve the performance of organic EL elements, organic EL elements with further improved element performance, and electronic devices comprising such organic EL elements.

[0014] means for solving problems

[0015] The inventors have repeatedly conducted in-depth studies on the performance of organic EL elements containing compounds described in Patent Documents 1 to 5, and found that the performance of organic EL elements containing compounds represented by the following formula (1) is further improved.

[0016] In one embodiment, the present invention provides a compound represented by the following formula (1).

[0017]

Chemical Formula 1

[0018]

[0019] In equation (1),

[0020] N ＊ The central nitrogen atom.

[0021] R 1 ~R 7 Each is independently a hydrogen atom or an unsubstituted phenyl group. (Selected from R) 1 ~R 7 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0022] R c and R d Each is an independent protium atom, or a methyl group having three protium atoms. R c With R d They do not bond with each other and therefore do not form a ring.

[0023] L 1 and L 2 Each is an arylene group that is either a single bond or an unsubstituted cyclic carbon group with 6 to 12 carbon atoms.

[0024] Ar 1 and Ar 2 Each is independently represented by the following formulas (2A), (2B), (2C), (2D), or (2E).

[0025] R c and R d At least one of the hydrogen atoms other than the hydrogen atom in the sample is a deuterium atom.

[0026] [Chemical Formula 2]

[0027]

[0028] In equation (2A),

[0029] *21 indicates the relationship with L 1 or L 2 The bond.

[0030] Selected from R101 ~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.

[0031] R is not the single bond mentioned above. 101 ~R 105 And R, which is not one of the above single bonds 106 ~R 110 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 9 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0032] R 111 ~R 115 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 9 carbon atoms, or a substituted or unsubstituted aryl group having 7 to 11 carbon atoms.

[0033] 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.

[0034] 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.

[0035] 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.

[0036] j is 0 or 1, k is 0 or 1. When j = 1 and k = 1, the L bonded to *21... 1 or L 2 Not unsubstituted phenylene, in the case of j=1, k=0, L bonded to *21 1 or L 2 The divalent group, not derived by removing one hydrogen atom from an unsubstituted biphenyl group, is bonded to *21 when j=0 and k=1. 1 or L 2 It is not a divalent group derived by removing one hydrogen atom from an unsubstituted biphenyl group.

[0037] When j=0 and k=0, *23 means *21.

[0038] When j=0 and k=1, *22 means *21.

[0039] When j=1 and k=0, *23 represents *22.

[0040]

Chemical Formula 3

[0041]

[0042] In equation (2B),

[0043] *24 indicates the relationship with L 1 or L 2 The bond.

[0044] Selected from R 121 ~R 128 One of them is a single bond that bonds with *25.

[0045] R is not the single bond mentioned above. 121 ~R 128 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 9 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0046] 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.

[0047] Among them, L bonded to the above *24 1 or L 2 When it is an unsubstituted phenylene, (i) is not the R of the single bond mentioned above. 121 ~R 128 All are hydrogen atoms, or (ii) are not the single bonds mentioned above. 121 ~R 128 One of them is an unsubstituted phenyl group, and it is not the single bond mentioned above or the R of the unsubstituted phenyl group mentioned above. 121 ~R 128 All are hydrogen atoms.

[0048] [Chemical Formula 4]

[0049]

[0050] In equation (2C),

[0051] *26 indicates the relationship with L 1 or L 2 The bond.

[0052] Selected from R 131 ~R 140 One of them is a single bond that bonds with *27.

[0053] R is not the single bond mentioned above. 131 ~R140 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 9 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0054] Selected from R that is not one of the above single bonds 131 ~R 140 Two adjacent elements in the [structure] do not bond with each other and therefore do not form a ring.

[0055] [Chemical Formula 5]

[0056]

[0057] In equation (2D),

[0058] *28 indicates the relationship with L 1 or L 2 The bond.

[0059] X 1 For oxygen atoms, or CR a R b .

[0060] p is either 0 or 1. Where, in X... 1 When the atom is oxygen, p is 1.

[0061] R a and R b Each is independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted cyclic aryl group having 6 to 12 carbon atoms. In R a and R b When at least one of them is methyl, R a and R b In at least one of the methyl groups, all hydrogen atoms are protium atoms. R a and R b They do not bond with each other and therefore do not form a ring.

[0062] When p is 0, the selection is from R. 141 ~R 148 One of them is a single bond that bonds with *29.

[0063] When p is 1, R 145 With R 146 R 146 With R 147 Or R 147 With R 148 When one of the bonds is a single bond bonded to *e and the other is a single bond bonded to *f, the R bond is selected from the single bond that is not bonded to either *e or *f. 145 ~R 148 R 141 ~R 144and R 200 ~R 203 One of them is a single bond that bonds with *29.

[0064] R is not the single bond mentioned above. 141 ~R 148 And R, which is not one of the above single bonds 200 ~R 203 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 9 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 carbon atoms.

[0065] In X 1 For CR a R b And R 141 Or R 148 When R is a single bond that bonds with *29, a and R b At least one of them is a substituted or unsubstituted aryl group with 6 to 12 carbon atoms in a cyclic ring.

[0066] 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 [structure] do not bond with each other and therefore do not form a ring.

[0067]

Chemical Formula 6

[0068]

[0069] In equation (2E),

[0070] *30 indicates the relationship with L 1 or L 2 The bond.

[0071] 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.

[0072] R is not the single bond mentioned above. 151 ~R 155 R 161 ~R 165 and R 171 ~R 175Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 9 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0073] 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.

[0074] Selected from R 161 ~R 165 At least one pair of adjacent 2 elements in the ring do not bond to each other and do not form a ring.

[0075] Selected from R 171 ~R 175 At least one pair of adjacent pairs in the [structure] are not bonded to each other and therefore do not form a loop.

[0076] In another embodiment, the present invention provides a material for an organic EL element comprising the compound shown in formula (1) above.

[0077] 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 comprising a light-emitting layer, and at least one layer of the organic layer comprising the aforementioned compound.

[0078] In another embodiment, the present invention provides an electronic device comprising the above-described organic electroluminescent element.

[0079] The effects of the invention

[0080] Organic EL elements containing the compound shown in formula (1) above exhibit improved element performance. Attached Figure Description

[0081] 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.

[0082] 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.

[0083] Figure 3 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. Detailed Implementation

[0084] [definition]

[0085] In this specification, a hydrogen atom means an isotope containing different numbers of neutrons, namely protium, deuterium, and tritium.

[0086] 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.

[0087] 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.

[0088] 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.

[0089] 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.

[0090] 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.

[0091] 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.

[0092] In this specification, "unsubstituted ZZ group" means "substituted or unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".

[0093] 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.

[0094] 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.

[0095] Substituents described in this specification

[0096] The substituents described in this specification are explained below.

[0097] 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.

[0098] 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.

[0099] 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.

[0100] 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.

[0101] 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.

[0102] 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.

[0103] 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.

[0104] Unless otherwise specified 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.

[0105] 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.

[0106] • "Substituted or unsubstituted aryl groups"

[0107] 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.

[0108] "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.

[0109] • Unsubstituted aryl groups (specific example group G1A):

[0110] phenyl,

[0111] p-phenyl,

[0112] metaphenyl,

[0113] o-phenyl,

[0114] p-terphenyl-4-yl,

[0115] p-terphenyl-3-yl,

[0116] p-terphenyl-2-yl,

[0117] m-terphenyl-4-yl,

[0118] m-terphenyl-3-yl,

[0119] m-terphenyl-2-yl,

[0120] o-terphenyl-4-yl

[0121] o-terphenyl-3-yl

[0122] o-terphenyl-2-yl,

[0123] 1-Naphthyl,

[0124] 2-Naphthyl,

[0125] anthracene,

[0126] Benzanthracene,

[0127] Fiki,

[0128] Benzphenanthrene,

[0129] Finadenyl,

[0130] Pyrene

[0131] chrysenyl group,

[0132] benzochrysenyl group,

[0133] triphenylenyl group,

[0134] benzo[triphenylenyl] group,

[0135] tetracenyl group,

[0136] pentacenyl group,

[0137] fluorenyl group,

[0138] 9,9'-spirobifluorenyl group,

[0139] benzofluorenyl group,

[0140] dibenzofluorenyl group,

[0141] fluoranthenyl group,

[0142] benzofluoranthenyl group,

[0143] perylenyl group, and

[0144] a monovalent aryl group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0145] [Chemical Formula 2]

[0146]

[0147] [Chemical Formula 3]

[0148]

[0149] ·Substituted aryl groups (specific example group G1B):

[0150] o-tolyl group,

[0151] m-tolyl group,

[0152] p-tolyl group,

[0153] p-xylyl group,

[0154] m-xylyl group,

[0155] o-xylyl group,

[0156] p-isopropylphenyl group,

[0157] m-isopropylphenyl group,

[0158] o-isopropylphenyl group,

[0159] p-tert-butylphenyl group,

[0160] m-tert-butylphenyl,

[0161] o-tert-butylphenyl,

[0162] 3,4,5-Trimethylphenyl

[0163] 9,9-Dimethylfluorenyl,

[0164] 9,9-Diphenylfluorenyl

[0165] 9,9-Bis(4-methylphenyl)fluorenyl,

[0166] 9,9-Bis(4-isopropylphenyl)fluorenyl,

[0167] 9,9-Bis(4-tert-butylphenyl)fluorenyl,

[0168] cyanophenyl,

[0169] Triphenylsilylphenyl

[0170] Trimethylsilylphenyl

[0171] Phenynaphthyl,

[0172] Naphthylphenyl, and

[0173] 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.

[0174] • "Substituted or unsubstituted heterocyclic groups"

[0175] 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.

[0176] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.

[0177] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0178] 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".

[0179] "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.

[0180] 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 from the ring structures shown in the following general formulas (TEMP-16) to (TEMP-33) by removing one hydrogen atom (specific example group G2A4).

[0181] 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).

[0182] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1):

[0183] pyrrole,

[0184] Imidazole group,

[0185] Pyrazolyl,

[0186] Triazole group,

[0187] Tetrazolyl,

[0188] Oxazolyl,

[0189] Isoxazolyl,

[0190] Oxadiazole group,

[0191] Thiazole group,

[0192] Isothiazolyl,

[0193] Thiadiazole group,

[0194] pyridyl,

[0195] pyridazinyl,

[0196] Pyrimidine group,

[0197] Pyrazinyl,

[0198] Triazine group

[0199] Indole,

[0200] Isoindolyl,

[0201] Indazine group

[0202] Quinazine-based

[0203] Quinoline,

[0204] Isoquinoline,

[0205] Crenoline group

[0206] Phthaloazine

[0207] Quinazolinyl,

[0208] Quinoxaloyl,

[0209] Benzimidazole group,

[0210] Indazole group,

[0211] phenanthroline,

[0212] phenanthridine,

[0213] acridine group,

[0214] Phenazine group,

[0215] Carbazole group,

[0216] Benzocarbazolyl,

[0217] Morpholinyl

[0218] phenoxazine group,

[0219] phenothiazine group,

[0220] Azacarbazolyl and diazacarbazolyl.

[0221] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2):

[0222] furanyl,

[0223] Oxazolyl,

[0224] Isoxazolyl,

[0225] Oxadiazole group,

[0226] Xuton base,

[0227] Benzofuranyl,

[0228] Isobenzofuranyl,

[0229] Dibenzofuranyl,

[0230] Naphthobenzofuranyl,

[0231] Benzoxazolyl,

[0232] Benzisoxazole group,

[0233] phenoxazine group,

[0234] Morpholinyl

[0235] Dinaphthylfuranyl,

[0236] Azadibenzofuranyl,

[0237] diazadibenzofuranyl,

[0238] Azanaphthalenebenzofuranyl, and

[0239] Diazanaphthenebenzofuranyl.

[0240] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3):

[0241] Thiophene group

[0242] Thiazole group,

[0243] Isothiazolyl,

[0244] Thiadiazole group,

[0245] benzothienyl

[0246] isobenzothienyl

[0247] dibenzothienyl

[0248] Naphthobenzothienyl

[0249] Benzothiazolyl,

[0250] Benzisothiazolyl,

[0251] phenothiazine group,

[0252] dinaphthothienyl

[0253] azadibenzothienyl

[0254] diazadibenzothienyl

[0255] azanaphthobenzothienyl and

[0256] diazanaphthobenzothienyl.

[0257] • The monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures shown in the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0258] [Chemical Formula 4]

[0259]

[0260] [Chemical Formula 5]

[0261]

[0262] 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.

[0263] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A When at least one of them is NH or CH2, the monovalent heterocyclic group derived from the ring structure shown in the above general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0264] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1):

[0265] (9-phenyl)carbazole group,

[0266] (9-Biphenyl)carbazolyl,

[0267] (9-Phenyl)phenylcarbazolyl,

[0268] (9-Naphthyl)carbazole,

[0269] Diphenylcarbazole-9-yl,

[0270] Phenylexacarbazole-9-yl,

[0271] Methylbenzimidazole,

[0272] Ethylbenzimidazole,

[0273] Phenylacetyl,

[0274] Biphenyltriazine

[0275] diphenyltriazine group,

[0276] phenylquinazolinyl, and

[0277] Biphenylquinazolinyl.

[0278] • Heterocyclic groups containing oxygen atoms (specific example group G2B2):

[0279] Phenyl dibenzofuranyl,

[0280] Methyldibenzofuranyl,

[0281] tert-butyldibenzofuranyl, and

[0282] The monovalent residue of [9H-xanton-9,9'-[9H]fluorene].

[0283] • Heterocyclic groups containing sulfur atoms (specific example group G2B3):

[0284] Phenyl dibenzothiophene,

[0285] Methyldibenzothiophene,

[0286] tert-butyldibenzothiophene, and

[0287] The monovalent residue of [9H-thiophene-9,9'-[9H]fluorene].

[0288] • 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):

[0289] 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.

[0290] • "Substituted or unsubstituted alkyl groups"

[0291] 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.

[0292] "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.

[0293] • Unsubstituted alkyl groups (specific example group G3A):

[0294] methyl,

[0295] Ethyl,

[0296] n-propyl,

[0297] Isopropyl,

[0298] n-Butyl,

[0299] Isobutyl,

[0300] sec-butyl, and

[0301] tert-butyl.

[0302] • Substituted alkyl groups (specific example group G3B):

[0303] Heptafluoropropyl (including isomers),

[0304] Pentafluoroethyl,

[0305] 2,2,2-Trifluoroethyl, and

[0306] Trifluoromethyl

[0307] • "Substituted or unsubstituted alkenyl groups"

[0308] 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.

[0309] "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.

[0310] • Unsubstituted alkenyl groups (specific example group G4A):

[0311] vinyl,

[0312] Allyl

[0313] 1-Butenyl,

[0314] 2-Butenyl, and

[0315] 3-Butenyl.

[0316] • Substituted alkenyl groups (specific example group G4B):

[0317] 1,3-Butadienyl,

[0318] 1-Methylvinyl

[0319] 1-Methylallyl,

[0320] 1,1-Dimethylallyl,

[0321] 2-Methylallyl, and

[0322] 1,2-Dimethylallyl.

[0323] • "Substituted or unsubstituted alkynyl groups"

[0324] 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".

[0325] "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.

[0326] • Unsubstituted alkynyl group (specific example group G5A):

[0327] Acetylene

[0328] • "Substituted or unsubstituted cycloalkyl groups"

[0329] 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.

[0330] "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.

[0331] • Unsubstituted cycloalkyl groups (specific example group G6A):

[0332] Cyclopropyl

[0333] Cyclobutyl,

[0334] Cyclopentyl,

[0335] Cyclohexyl,

[0336] 1-Adamantyl,

[0337] 2-Adamantyl,

[0338] 1-norborneol, and

[0339] 2-norborneol.

[0340] • Substituted cycloalkyl groups (specific example group G6B):

[0341] 4-Methylcyclohexyl.

[0342] ·"-Si(R 901 (R) 902 (R) 903 The group shown in the figure”

[0343] 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:

[0344] -Si(G1)(G1)(G1),

[0345] -Si(G1)(G2)(G2),

[0346] -Si(G1)(G1)(G2),

[0347] -Si(G2)(G2)(G2),

[0348] -Si(G3)(G3)(G3) and

[0349] -Si(G6)(G6)(G6). Here,

[0350] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0351] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0352] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0353] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0354] In -Si(G1)(G1)(G1), multiple G1s may be the same or different from each other.

[0355] In -Si(G1)(G2)(G2), multiple G2s may be the same or different from each other.

[0356] In -Si(G1)(G1)(G2), multiple G1s may be the same or different from each other.

[0357] In -Si(G2)(G2)(G2), multiple G2s may be the same or different from each other.

[0358] In -Si(G3)(G3)(G3), multiple G3s may be the same or different from each other.

[0359] In -Si(G6)(G6)(G6), multiple G6s may be the same or different from each other.

[0360] ·“-O-(R 904 The group shown in the figure”

[0361] 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:

[0362] -O(G1)

[0363] -O(G2),

[0364] -O(G3) and

[0365] -O(G6).

[0366] Here,

[0367] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0368] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0369] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0370] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0371] ·“-S-(R 905 The group shown in the figure”

[0372] 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:

[0373] -S(G1),

[0374] -S(G2),

[0375] -S(G3) and

[0376] -S(G6).

[0377] Here,

[0378] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0379] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0380] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0381] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0382] ·"-N(R 906 (R) 907 The group shown in the figure”

[0383] 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:

[0384] -N(G1)(G1),

[0385] -N(G2)(G2),

[0386] -N(G1)(G2),

[0387] -N(G3)(G3) and

[0388] -N(G6)(G6).

[0389] Here,

[0390] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0391] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0392] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0393] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0394] In -N(G1)(G1), multiple G1s may be the same or different from each other.

[0395] In -N(G2)(G2), multiple G2 values ​​may be the same or different from each other.

[0396] In -N(G3)(G3), multiple G3s may be the same or different from each other.

[0397] In -N(G6)(G6), multiple G6 values ​​may be the same or different from each other.

[0398] • "Halogen atom"

[0399] Specific examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0400] • "Substituted or unsubstituted fluoroalkyl groups"

[0401] 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.

[0402] • "Substituted or unsubstituted haloalkyl groups"

[0403] 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.

[0404] • "Substituted or unsubstituted alkoxy groups"

[0405] 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.

[0406] • "Substituted or unsubstituted alkylthio groups"

[0407] 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.

[0408] • "Substituted or unsubstituted aryloxy groups"

[0409] 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.

[0410] • "Substituted or unsubstituted arylthio groups"

[0411] 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.

[0412] • "Substituted or unsubstituted trialkylsilyl groups"

[0413] 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.

[0414] • "Substituted or unsubstituted aralkyl groups"

[0415] 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.

[0416] 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.

[0417] 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.

[0418] 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.

[0419] In this specification, the carbazoyl group, unless otherwise specified herein, specifically refers to any one of the following groups.

[0420] [Chemical Formula 6]

[0421]

[0422] In this specification, (9-phenyl)carbazolyl refers specifically to any one of the following groups unless otherwise stated herein.

[0423] [Chemical Formula 7]

[0424]

[0425] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.

[0426] In this specification, dibenzofuranyl and dibenzothiopheneyl are specifically any one of the following groups unless otherwise stated in this specification.

[0427] [Chemical Formula 8]

[0428]

[0429] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.

[0430] 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.

[0431] • "Substituted or unsubstituted aryl groups"

[0432] Unless otherwise stated, the "substituted or unsubstituted aryl group" described in this specification refers to 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.

[0433] • "Substituted or unsubstituted divalent heterocyclic groups"

[0434] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification refers to 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.

[0435] • "Substituted or unsubstituted alkylene compounds"

[0436] Unless otherwise stated, "substituted or unsubstituted alkylene" as described in this specification refers to a divalent group derived from the aforementioned "substituted or unsubstituted alkyl" by removing one hydrogen atom from the alkyl chain. Specific examples of "substituted or unsubstituted alkylene" (Specific Example Group G14) include divalent groups derived from the "substituted or unsubstituted alkyl" described in Specific Example Group G3 by removing one hydrogen atom from the alkyl chain.

[0437] 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).

[0438] [Chemical Formula 9]

[0439]

[0440] [Chemical Formula 10]

[0441]

[0442] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0443] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.

[0444] [Chemical Formula 11]

[0445]

[0446] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0447] Formulas Q9 and Q 10 They can form rings by bonding with each other via single bonds.

[0448] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.

[0449] [Chemical Formula 12]

[0450]

[0451] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0452] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.

[0453] 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).

[0454] [Chemical Formula 13]

[0455]

[0456] [Chemical Formula 14]

[0457]

[0458] [Chemical Formula 15]

[0459]

[0460] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0461] [Chemical Formula 16]

[0462]

[0463] [Chemical Formula 17]

[0464]

[0465] [Chemical Formula 18]

[0466]

[0467] [Chemical Formula 19]

[0468]

[0469] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0470] The above is an explanation of "substituents described in this specification".

[0471] • "Cases where bonds form rings"

[0472] 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".

[0473] 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.

[0474] [Chemical Formula 20]

[0475]

[0476] 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", the group consisting of two adjacent elements that form a group refers to 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.

[0477] The phrase "one or more groups" refers to the fact that two or more 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 QA 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).

[0478] [Chemical Formula 21]

[0479]

[0480] 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, this 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 923 When 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 .

[0481] [Chemical Formula 22]

[0482]

[0483] In the formed "single ring" or "fused ring", the ring itself can be either a saturated or unsaturated ring. Even when a "single ring" or "fused ring" is formed from "one of two adjacent groups", it can still be either a saturated or 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 CFusing 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.

[0484] "Unsaturated rings" refer to aromatic hydrocarbon rings or aromatic heterocycles. "Saturated rings" refer to aliphatic hydrocarbon rings or non-aromatic heterocycles.

[0485] 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.

[0486] 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.

[0487] 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.

[0488] "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.

[0489] 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.

[0490] 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.

[0491] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".

[0492] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".

[0493] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.

[0494] Unless otherwise stated in this specification, the "unsaturated ring" is preferably a benzene ring.

[0495] In the case of "one or more groups consisting of two or more adjacent atoms" or "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 atoms form an "unsaturated ring" formed by mutual bonding of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0496] 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.

[0497] 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.

[0498] The above explains the cases of "a single ring formed by bonding one or more groups of two or more adjacent elements together, whether substituted or unsubstituted" and "a fused ring formed by bonding one or more groups of two or more adjacent elements together, whether substituted or unsubstituted" ("the case of forming a ring by bonding").

[0499] Substituents when described as "substituted or unsubstituted"

[0500] 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...

[0501] Unsubstituted alkyl groups having 1 to 50 carbon atoms

[0502] Unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0503] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms

[0504] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0505] -Si(R 901 (R) 902 (R) 903 ),

[0506] -O-(R 904 ),

[0507] -S-(R 905 ),

[0508] -N(R 906 (R) 907 ),

[0509] Halogen atom, cyano group, nitro group,

[0510] Unsubstituted aryl groups with 6 to 50 carbon atoms, and

[0511] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms

[0512] Groups, etc., in the composition group

[0513] Here, R 901 ~R 907 Each independently

[0514] hydrogen atom,

[0515] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0516] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0517] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0518] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0519] In R 901 In the case of two or more R, two or more R 901 They are the same or different.

[0520] In R902 In the case of two or more R, two or more R 902 They are the same or different.

[0521] In R 903 In the case of two or more R, two or more R 903 They are the same or different.

[0522] In R 904 In the case of two or more R, two or more R 904 They are the same or different.

[0523] In R 905 In the case of two or more R, two or more R 905 They are the same or different.

[0524] In R 906 In the case of two or more R, two or more R 906 They are the same or different.

[0525] In R 907 In the case of two or more R, two or more R 907 They are the same or different.

[0526] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.

[0527] Alkyl groups with 1 to 50 carbon atoms

[0528] aryl groups with 6 to 50 carbon atoms, and

[0529] Heterocyclic groups with 5 to 50 cyclic atoms

[0530] The groups that make up the group.

[0531] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.

[0532] Alkyl groups having 1 to 18 carbon atoms

[0533] aryl groups with 6 to 18 carbon atoms, and

[0534] Heterocyclic groups with 5 to 18 cyclic atoms

[0535] The groups that make up the group.

[0536] Specific examples of the substituents mentioned above are those described in the section "Substituents as set forth in this specification".

[0537] 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.

[0538] 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.

[0539] 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.

[0540] The compounds of the present invention will be described below.

[0541] The compounds of the present invention are represented by the following formula (1). Hereinafter, the compounds of the present invention represented by formula (1) will sometimes be referred to simply as "inventive compounds".

[0542]

Chemical Formula 23

[0543]

[0544] The symbols in equation (1) will be explained below. It should be noted that the same symbols have the same meaning.

[0545] In equation (1), N ＊ The central nitrogen atom.

[0546] In equation (1), R 1 ~R 7 There are no particular limitations as long as each atom is an independent hydrogen atom or an unsubstituted phenyl group; however, from the viewpoint of material manufacturing cost, hydrogen atoms are preferred.

[0547] In equation (1), the values ​​selected from R 1 ~R 7 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0548] In equation (1), R c and R d There are no particular limitations as long as each is an independent protium atom or a methyl group having 3 protium atoms. From the viewpoint of molecular electrostability, a methyl group having 3 protium atoms is preferred.

[0549] In equation (1), R c With R dThey do not bond with each other and therefore do not form a ring.

[0550] In equation (1), L 1 and L 2 There are no particular limitations as long as each is an independent single bond or an unsubstituted arylene group with 6 to 12 carbon atoms in the cyclic group. From the viewpoint of heat resistance and excitation stability, single bonds or unsubstituted phenylene groups are preferred, and unsubstituted phenylene groups are more preferred.

[0551] It should be noted that in L 1 or L 2 In the case of a single bond, Ar 1 Or Ar 2 This refers to direct bonding with the central nitrogen, such as Ar. 1 Or Ar 2 For equations (2A), (2B), (2C), (2D), or (2E), in L 1 or L 2 In the case of single bonds, *21, *24, *26, *28, and *30 in formulas (2A), (2B), (2C), (2D), or (2E) are directly bonded to the central nitrogen.

[0552] In L 1 and L 2 The substituted or unsubstituted aryl group having 6 to 12 carbon atoms is not particularly limited in its unsubstituted form; examples include phenylene, biphenylene, and naphthylene. Among these, phenylene is preferred from the viewpoint of heat resistance and activation stability.

[0553] In equation (1), Ar 1 and Ar 2 There are no particular limitations as long as each is independently represented by the following formulas (2A), (2B), (2C), (2D) or (2E). From the viewpoint of stimulating stability, it is preferred to represent them by the following formulas (2A), (2B) or (2D), and more preferably by the following formulas (2A) or (2B).

[0554] In addition, Ar is preferred. 1 and Ar 2 At least one of them is represented by the following formula (2A).

[0555] [Chemical Formula 24]

[0556]

[0557] In equation (2A), *21 represents the relationship with L. 1 or L 2 The bond.

[0558] 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.

[0559] R is not a single bond 101 ~R 105 And R, which is not a single bond. 106 ~R 110 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 9 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, preferably a hydrogen atom.

[0560] In equation (2A), R 111 ~R 115 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 2 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 9 carbon atoms, or a substituted or unsubstituted aryl group having 7 to 11 carbon atoms, preferably a hydrogen atom.

[0561] In R, which is not a single bond 101 ~R 105 R is not a single bond 106 ~R 110 and R 111 ~R 115 The substituted or unsubstituted alkyl group having 2 to 10 carbon atoms is not particularly limited in its choice of unsubstituted alkyl group having 2 to 10 carbon atoms; examples include ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, etc. Among these, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl are preferred, more preferably ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, and particularly preferably tert-butyl.

[0562] In R, which is not a single bond 101 ~R 105 R is not a single bond 106 ~R 110 and R 111 ~R 115 The unsubstituted or unsubstituted cycloalkyl group having 3 to 9 carbon atoms is not particularly limited, and examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-norbornyl, and 2-norbornyl. Among these, cyclopropyl, cyclobutyl, cyclohexyl, and 1-norbornyl are preferred.

[0563] In R, which is not a single bond 101~R 105 And R which is not a single bond 106 ~R 110 The substituted or unsubstituted aryl group having 6 to 12 carbon atoms is not particularly limited in its composition. Examples of unsubstituted aryl groups having 6 to 12 carbon atoms include phenyl, biphenyl, and naphthyl. Among these, phenyl, 2-biphenyl, 3-biphenyl, or 4-biphenyl (biphenyl), 1-naphthyl, or 2-naphthyl are preferred, more preferably phenyl, 1-naphthyl, or 2-naphthyl, and particularly preferably phenyl.

[0564] In R 111 ~R 115 The substituted or unsubstituted aryl group having 7 to 11 carbon atoms is not particularly limited in its composition; examples include indole and naphthyl. Among these, naphthyl is preferred.

[0565] In equation (2A), R is selected from bonds that are not single bonds. 101 ~R 105 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0566] In equation (2A), R is selected from bonds that are not single bonds. 106 ~R 110 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0567] In equation (2A), the values ​​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.

[0568] In equation (2A), j is 0 or 1, and k is 0 or 1. When j = 1 and k = 1, the L bonded to *21... 1 or L 2 Not unsubstituted phenylene, in the case of j=1, k=0, L bonded to *21 1 or L 2 The divalent group, not derived by removing one hydrogen atom from an unsubstituted biphenyl group, is bonded to *21 when j=0 and k=1. 1 or L 2 It is not a divalent group derived by removing one hydrogen atom from an unsubstituted biphenyl group.

[0569] When j=0 and k=0, *23 means *21.

[0570] When j=0 and k=1, *22 means *21.

[0571] When j=1 and k=0, *23 means *22.

[0572] 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.

[0573] [Chemical Formula 25]

[0574]

[0575] 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.

[0576]

Chemical Formula 26

[0577]

[0578] 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.

[0579] [Chemical Formula 27]

[0580]

[0581] In another embodiment of the invention, j is 1 and k is 1. In this case, equation (2A) is represented by the following equation.

[0582] [Chemical Formula 28]

[0583]

[0584] The group represented by formula (2A) is preferably represented by the following formula. In the following formula, R is omitted for simplification.

[0585] [Chemical Formula 29]

[0586]

[0587] 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.

[0588]

Chemical Formula 30

[0589]

[0590] In equation (2B), *24 represents L 1 or L 2 The bond.

[0591] In equation (2B), the values ​​selected from R 121 ~R 128 One of them is a single bond that bonds with *25.

[0592] In equation (2B), R is not a single bond. 121 ~R 128 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 9 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0593] In equation (2B), R is selected from bonds that are not single bonds. 121 ~R 128 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0594] In equation (2B), in L bonded with *24 1 or L 2 When it is an unsubstituted phenylene, (i) is not a single bond R 121 ~R 128 All are hydrogen atoms; or (ii) R is not a single bond. 121 ~R 128 One of them is an unsubstituted phenyl group, and it is not a single bond or R of the unsubstituted phenyl group. 121 ~R 128 All are hydrogen atoms.

[0595] R 121 ~R 128 Details and preferred examples of substituted or unsubstituted alkyl groups having 2 to 10 carbon atoms, and for the purposes of the above-mentioned R 101 ~R 105 The records are the same.

[0596] R 121 ~R 128 Details and preferred examples of substituted or unsubstituted cycloalkyl groups with 3 to 9 carbon atoms, and related to the above-mentioned R 101 ~R 105 The records are the same.

[0597] R 121 ~R 128 Details and preferred examples of substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, and related to the above-mentioned R 101 ~R 105 The records are the same.

[0598] 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.

[0599] R is not a single bond that bonds with *25 121 ~R 128 Both can be hydrogen atoms.

[0600]

Chemical Formula 31

[0601]

[0602] In equation (2C), *26 represents L 1 or L 2 The bond.

[0603] In equation (2C), the values ​​selected from R 131 ~R 140 One of them is a single bond that bonds with *27.

[0604] In equation (2C), R is not a single bond. 131 ~R 140 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 9 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0605] In equation (2C), R is selected from bonds that are not single bonds. 131 ~R 140 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0606] R 131 ~R 140 Details and preferred examples of substituted or unsubstituted alkyl groups having 2 to 10 carbon atoms, and for the purposes of the above-mentioned R 101 ~R 105 The records are the same.

[0607] R 131 ~R 140 Details and preferred examples of substituted or unsubstituted cycloalkyl groups with 3 to 9 carbon atoms, and related to the above-mentioned R 101 ~R 105 The records are the same.

[0608] R 131 ~R 140 Details and preferred examples of substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, and related to the above-mentioned R 101 ~R 105 The records are the same.

[0609] 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 137It is a single bond that bonds with *27.

[0610] R is not a single bond that bonds with *27 131 ~R 140 Both can be hydrogen atoms.

[0611]

Chemical Formula 32

[0612]

[0613] In equation (2D), *28 represents the relationship with L. 1 or L 2 The bond.

[0614] In equation (2D), X 1 For oxygen atoms, or CR a R b CR is preferred a R b .

[0615] In equation (2D), p is either 0 or 1. Wherein, in X... 1 When the atom is oxygen, p is 1.

[0616] In equation (2D), R a and R b Each is independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted cyclic aryl group having 6 to 12 carbon atoms, preferably, (i)R a and R b Both of these are unsubstituted methyl groups (e.g., see “Compound Inv-7” described later), (ii)R a and R b Both of these are unsubstituted phenyl groups (e.g., see “Compound Inv-5” described later), (iii)R a and R b One of them is an unsubstituted methyl group and R a and R b The other one is an unsubstituted phenyl group (see, for example, “Compound Inv-6” described later).

[0617] In equation (2D), in R a and R b When at least one of them is an unsubstituted methyl group, R a and R b All hydrogen atoms in the unsubstituted methyl group represented by at least one of the terms are protium atoms.

[0618] In equation (2D), R a With R b They do not bond with each other and therefore do not form a ring.

[0619] In Ra and R b The substituted or unsubstituted alkyl group having 1 to 10 carbon atoms is not particularly limited in its choice of unsubstituted alkyl group having 1 to 10 carbon atoms; examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, etc. Among these, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl are preferred, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl are more preferred, and methyl or tert-butyl are particularly preferred.

[0620] R a and R b Details and preferred examples of substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, and related to the above-mentioned R 101 ~R 105 The records are the same.

[0621] In equation (2D), when p is 0, the value selected from R is... 141 ~R 148 One of them is a single bond that bonds with *29.

[0622] In equation (2D), when p is 1 and R is 1, 145 With R 146 R 146 With R 147 Or R 147 With R 148 When one of the bonds is a single bond bonded to *e and the other is a single bond bonded to *f, the R bond is selected from the single bond that is not bonded to either *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.

[0623] In equation (2D), R is not a single bond. 141 ~R 148 And R, which is not a single bond. 200 ~R 203 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 9 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 carbon atoms.

[0624] In equation (2D), R is selected from bonds that are not single bonds. 141 ~R 148 And R which is not a single bond 200 ~R203 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0625] R 141 ~R 148 and R 200 ~R 203 Details and preferred examples of substituted or unsubstituted alkyl groups having 2 to 10 carbon atoms, and for the purposes of the above-mentioned R 101 ~R 105 The records are the same.

[0626] R 141 ~R 148 and R 200 ~R 203 Details and preferred examples of substituted or unsubstituted cycloalkyl groups with 3 to 9 carbon atoms, and related to the above-mentioned R 101 ~R 105 The records are the same.

[0627] R 141 ~R 148 and R 200 ~R 203 Details and preferred examples of substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, and related to the above-mentioned R 101 ~R 105 The records are the same.

[0628] In R 141 ~R 148 and R 200 ~R 203The substituted or unsubstituted heteroaryl group having 5 to 13 cyclic atoms is not particularly limited in its choice of unsubstituted heteroaryl group; examples include pyrrole, furanyl, thiophene, pyridinyl, imidazopyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiazolyl, triazolyl, tetrazolyl, indole, isoindole, indazinyl, quinazinyl, and quinoline. The group includes: α-hydroxyl, isoquinolinyl, cyclophosphinyl, phthalazinyl, quinazolinyl, quinoxolinyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, indazole, benzoisoxazolyl, benzoisothiazolyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothienyl, isobenzothienyl, dibenzothienyl, carbazolyl, etc. Among them, furanyl, thiophene, pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothiophene, isobenzothiophene, dibenzothiophene, or carbazoleyl are preferred, and more preferably benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothiophene, isobenzothiophene, dibenzothiophene, or carbazoleyl (9-carbazoleyl, 1-carbazoleyl, 2-carbazoleyl, 3-carbazoleyl, or 4-carbazoleyl).

[0629] As R 141 ~R 148 and R 200 ~R 203 The substituted heteroaryl group with 5 to 13 cyclic atoms is not particularly limited, and examples include 9-phenylcarbazolyl, 9-biphenylcarbazolyl, 9-phenylphenylcarbazolyl, 9-naphthylcarbazolyl, phenyldibenzofuranyl, phenyldibenzothienyl (hereinafter the same), etc.

[0630] The aforementioned heteroaryl groups with 5 to 13 cyclic atoms, whether substituted or unsubstituted, also include isomer groups in the presence of isomer groups.

[0631] In equation (2D), at X 1 For CR a R b And R 141 Or R 148 When R is a single bond that bonds with *29, a and R b At least one of them is a substituted or unsubstituted aryl group with 6 to 12 carbon atoms in a cyclic ring.

[0632] R a and R bDetails and preferred examples of substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, and related to the above-mentioned R 101 ~R 105 The records are the same.

[0633]

Chemical Formula 33

[0634]

[0635] In equation (2E), *30 represents L 1 or L 2 The bond.

[0636] 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.

[0637] In equation (2E), R is not a single bond. 151 ~R 155 R 161 ~R 165 and R 171 ~R 175 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 cycloalkyl group having 3 to 9 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0638] In equation (2E), R is selected from bonds that are not single bonds. 151 ~R 155 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0639] In equation (2E), the values ​​selected from R 161 ~R 165 At least one pair of adjacent 2 elements in the ring do not bond to each other and do not form a ring.

[0640] In equation (2E), the values ​​selected from R 171 ~R 175 At least one pair of adjacent 2 elements in the ring do not bond to each other and do not form a ring.

[0641] In R 151 ~R 155 R 161 ~R 165 and R 171 ~R 175The substituted or unsubstituted alkyl group having 1 to 10 carbon atoms is not particularly limited in its choice of unsubstituted alkyl group having 1 to 10 carbon atoms; examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, etc. Among these, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl are preferred; methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl are more preferred; methyl or tert-butyl are even more preferred; and tert-butyl is particularly preferred.

[0642] R 151 ~R 155 R 161 ~R 165 and R 171 ~R 175 Details and preferred examples of substituted or unsubstituted cycloalkyl groups with 3 to 9 carbon atoms, and related to the above-mentioned R 101 ~R 105 The records are the same.

[0643] R 151 ~R 155 R 161 ~R 165 and R 171 ~R 175 Details and preferred examples of substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, and related to the above-mentioned R 101 ~R 105 The records are the same.

[0644] R is not a single bond 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.

[0645] 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.

[0646] 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 is the compound shown in formula (1), wherein the R contained in the compound... c and R d At least one of the hydrogen atoms other than the hydrogen atom in the atom is a deuterium atom.

[0647] In the compound shown in formula (1) L 1 and L 2 When the two phenylene atoms are unsubstituted, at least one of the hydrogen atoms in one of the unsubstituted phenylene atoms may be a deuterium atom (see, for example, "Compound Inv-1" to "Compound Inv-4" and "Compound Inv-8" to "Compound Inv-11" described below).

[0648] In the compound shown in formula (1) L 1 and L 2 When the two phenylene groups are unsubstituted, the hydrogen atoms in one of the unsubstituted phenylene groups can both be deuterium atoms (see, for example, "Compound Inv-2" and "Compound Inv-10" described later).

[0649] In the compound shown in formula (1) L 1 and L 2 When the phenylene atoms are unsubstituted, the hydrogen atoms in these two phenylene atoms can both be deuterium atoms (see, for example, "Compound Inv-3", "Compound Inv-4", "Compound Inv-8", "Compound Inv-9", and "Compound Inv-11" described below).

[0650] Ar in the compound shown in formula (1) 1 Or Ar 2 When expressed by “Equation (2A)(j=0,k=0)”, R 111 ~R 115 All of them can be deuterium atoms (see, for example, “Compound Inv-5” to “Compound Inv-7” described later).

[0651] 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.

[0652] 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 1–100%, 2–90%, 3–80%, 5–60%, 10–50%, or 20–30%.

[0653] 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%.

[0654] The proportion of deuterium atoms (specific deuteration rate) of the total hydrogen atoms (excluding hydrogen atoms in alkyl groups) in the aryl group of the inventive compound is not particularly limited, but is preferably 14.5% or more, more preferably 20.0% or more, and particularly preferably 25.0% or more.

[0655] The upper limit of the proportion of deuterium atoms (specific deuteration rate) of the total hydrogen atoms (excluding hydrogen atoms in alkyl groups) in the aryl group of the inventive compound can be 100%, 70.0%, or 60.0%.

[0656] The proportion of deuterium atoms (specific deuteration rate) of the total hydrogen atoms (excluding hydrogen atoms in alkyl groups) in the aryl group of the inventive compound can be 14.5–100.0%, 14.5–95.0%, 20.0–95.0%, 20.0–90.0%, 25.0–80.0%, 25.0–70.0%, or 25.0–60.0%.

[0657] If the proportion of deuterium atoms (specific deuteration rate) of the total hydrogen atoms (excluding hydrogen atoms in alkyl groups) in the invented compound is above the lower limit, the light-emitting element can achieve a sufficiently long lifetime effect relative to protium atoms.

[0658] It should be noted that the term "alkyl" as used above includes not only straight-chain or branched alkyl groups, but also cyclic alkyl groups (cycloalkyl groups).

[0659] 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 item “substituents described as “substituted or unsubstituted””.

[0660] Those skilled in the art can easily manufacture the inventive compounds by referring to the following synthetic examples and known synthetic methods.

[0661] The following examples of inventive compounds are shown, but are not limited to the illustrative compounds listed below. In addition to the compounds described in the illustrative compounds listed below, inventive compounds also include compounds in which a portion of the hydrogen is not deuterated in the synthetic technique.

[0662] In the specific examples below, D represents a deuterium atom.

[0663]

Chemical Formula 34

[0664]

[0665]

Chemical Formula 35

[0666]

[0667]

Chemical Formula 36

[0668]

[0669]

Chemical Formula 37

[0670]

[0671] [Chemical Formula 38]

[0672]

[0673] [Chemical Formula 39]

[0674]

[0675]

Chemical Formula 40

[0676]

[0677]

Chemical Formula 41

[0678]

[0679]

Chemical Formula 42

[0680]

[0681]

Chemical Formula 43

[0682]

[0683]

Chemical Formula 44

[0684]

[0685] [Chemical Formula 45]

[0686]

[0687]

Chemical Formula 46

[0688]

[0689] [Chemical Formula 47]

[0690]

[0691] [Chemical Formula 48]

[0692]

[0693] [Chemical Formula 49]

[0694]

[0695] [Chemical Formula 50]

[0696]

[0697]

Chemical Formula 51

[0698]

[0699]

Chemical Formula 52

[0700]

[0701]

Chemical Formula 53

[0702]

[0703] [Chemical Formula 54]

[0704]

[0705]

Chemical Formula 55

[0706]

[0707] [Chemical Formula 56]

[0708]

[0709] [Chemical Formula 57]

[0710]

[0711] [Chemical Formula 58]

[0712]

[0713] [Chemical Formula 59]

[0714]

[0715] [Chemical Formula 60]

[0716]

[0717]

Chemical Formula 61

[0718]

[0719]

Chemical Formula 62

[0720]

[0721]

Chemical Formula 63

[0722]

[0723]

Chemical Formula 64

[0724]

[0725]

Chemical Formula 65

[0726]

[0727]

Chemical Formula 66

[0728]

[0729] [Chemical Formula 67]

[0730]

[0731]

Chemical Formula 68

[0732]

[0733]

Chemical Formula 69

[0734]

[0735] [Chemical Formula 70]

[0736]

[0737]

Chemical Formula 71

[0738]

[0739]

Chemical Formula 72

[0740]

[0741]

Chemical Formula 73

[0742]

[0743] [Chemical Formula 74]

[0744]

[0745] [Chemical Formula 75]

[0746]

[0747] [Chemical Formula 76]

[0748]

[0749]

Chemical Formula 77

[0750]

[0751] [Chemical Formula 78]

[0752]

[0753] [Chemical Formula 79]

[0754]

[0755] [Chemical Formula 80]

[0756]

[0757]

Chemical Formula 81

[0758]

[0759]

Chemical Formula 82

[0760]

[0761]

Chemical Formula 83

[0762]

[0763]

Chemical Formula 84

[0764]

[0765]

Chemical Formula 85

[0766]

[0767]

Chemical Formula 86

[0768]

[0769] [Chemical Formula 87]

[0770]

[0771]

Chemical Formula 88

[0772]

[0773]

Chemical Formula 89

[0774]

[0775] [Chemical Formula 90]

[0776]

[0777]

Chemical Formula 91

[0778]

[0779]

Chemical Formula 92

[0780]

[0781] [Chemical Formula 93]

[0782]

[0783] [Chemical Formula 94]

[0784]

[0785] [Chemical Formula 95]

[0786]

[0787] [Chemical Formula 96]

[0788]

[0789] [Chemical Formula 97]

[0790]

[0791]

Chemical Formula 98

[0792]

[0793]

Chemical Formula 99

[0794]

[0795]

Chemical Formula 100

[0796]

[0797]

Chemical Formula 101

[0798]

[0799]

Chemical Formula 102

[0800]

[0801]

Chemical Formula 103

[0802]

[0803] [Chemical Formula 104]

[0804]

[0805] [Chemical Formula 105]

[0806]

[0807] [Chemical Formula 106]

[0808]

[0809] [Chemical Formula 107]

[0810]

[0811] [Chemical Formula 108]

[0812]

[0813] [Chemical Formula 109]

[0814]

[0815]

Chemical Formula 110

[0816]

[0817]

Chemical Formula 111

[0818]

[0819]

Chemical Formula 112

[0820]

[0821]

Chemical Formula 113

[0822]

[0823]

Chemical Formula 114

[0824]

[0825]

Chemical Formula 115

[0826]

[0827]

Chemical Formula 116

[0828]

[0829]

Chemical Formula 117

[0830]

[0831]

Chemical Formula 118

[0832]

[0833]

Chemical Formula 119

[0834]

[0835]

Chemical Formula 120

[0836]

[0837]

Chemical Formula 121

[0838]

[0839]

Chemical Formula 122

[0840]

[0841]

Chemical Formula 123

[0842]

[0843] [Chemical Formula 124]

[0844]

[0845] [Chemical Formula 125]

[0846]

[0847] [Chemical Formula 126]

[0848]

[0849] [Chemical Formula 127]

[0850]

[0851] [Chemical Formula 128]

[0852]

[0853] [Chemical Formula 129]

[0854]

[0855]

Chemical Formula 130

[0856]

[0857]

Chemical Formula 131

[0858]

[0859]

Chemical Formula 132

[0860]

[0861]

Chemical Formula 133

[0862]

[0863] [Chemical Formula 134]

[0864]

[0865] [Chemical Formula 135]

[0866]

[0867]

Chemical Formula 136

[0868]

[0869]

Chemical Formula 137

[0870]

[0871] [Chemical Formula 138]

[0872]

[0873]

Chemical Formula 139

[0874]

[0875] [Chemical Formula 140]

[0876]

[0877]

Chemical Formula 141

[0878]

[0879] [Chemical Formula 142]

[0880]

[0881] Materials for organic EL components

[0882] 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 not particularly limited, but 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%), more 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.

[0883] In one aspect of the present invention, the inventive compound is preferably a hole transport layer material.

[0884] One aspect of this invention relates to a hole transport layer material for organic electroluminescent devices.

[0885] Organic EL components

[0886] An organic EL element, as one aspect of the present invention, has an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer includes a light-emitting layer, and at least one layer of the organic layer contains the inventive compound.

[0887] 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 not particularly limited, but materials used as hole transport regions or light-emitting layers in fluorescent or phosphorescent EL elements are preferred, materials used as hole transport regions are more preferred, materials used as hole injection layers, hole transport layers, electron blocking layers, and exciton blocking layers are even more preferred, and materials used as hole injection layers and hole transport layers are particularly preferred.

[0888] 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. Among these, a fluorescent light-emitting element is preferred. Here, "light-emitting unit" refers to the smallest unit that includes an organic layer, wherein the organic layer is composed of a single layer or multiple layers, at least one of the single layer and multiple layers is a light-emitting layer, and emits light by recombination of injected holes and electrons.

[0889] For example, the following are typical component configurations for a simple organic EL element.

[0890] (1) Anode / Light-emitting unit / Cathode

[0891] 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.

[0892] (a)(hole injection layer / )hole transport layer / fluorescent layer / electron transport layer( / electron injection layer)

[0893] (b) (Hole injection layer / ) Hole transport layer / First fluorescent layer / Second fluorescent layer / Electron transport layer ( / Electron injection layer)

[0894] (c)(Hole injection layer / )Hole transport layer / phosphorescent layer / spacer layer / fluorescent layer / electron transport layer( / electron injection layer)

[0895] (d)(Hole injection layer / )Hole transport layer / First phosphorescent layer / Second phosphorescent layer / Spacer layer / Fluorescent layer / Electron transport layer( / Electron injection layer)

[0896] (e)(hole injection layer / )hole transport layer / phosphorescent layer / spacer layer / first fluorescent layer / second fluorescent layer / electron transport layer( / electron injection layer)

[0897] (f)(hole injection layer / )hole transport layer / electron blocking layer / fluorescent layer / electron transport layer( / electron injection layer)

[0898] (g)(hole injection layer / )hole transport layer / exciton blocking layer / fluorescent layer / electron transport layer( / electron injection layer)

[0899] (h)(Hole Injection Layer / )First Hole Transport Layer / Second Hole Transport Layer / Fluorescent Layer / Electron Transport Layer( / Electron Injection Layer)

[0900] (h1)(Hole Injection Layer / )First Hole Transport Layer / Second Hole Transport Layer / Third Hole Transport Layer / Fluorescent Layer / Electron Transport Layer( / Electron Injection Layer)

[0901] (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)

[0902] (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)

[0903] (j)(hole injection layer / )hole transport layer / fluorescent layer / hole blocking layer / electron transport layer( / electron injection layer)

[0904] (k)(hole injection layer / )hole transport layer / fluorescent layer / exciton blocking layer / electron transport layer( / electron injection layer)

[0905] 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.

[0906] 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.

[0907] The following are typical component configurations for tandem organic EL elements.

[0908] (2) Anode / First Light-Emitting Unit / Intermediate Layer / Second Light-Emitting Unit / Cathode

[0909] Here, the first light-emitting unit and the second light-emitting unit are not particularly limited, and for example, they can be selected independently from the light-emitting units mentioned above.

[0910] 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.

[0911] 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.

[0912] 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 1 The 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.

[0913] 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.

[0914] Figure 3This 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.

[0915] 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.

[0916] It should be noted that in this invention, the host material combined with a fluorescent dopant material (fluorescent luminescent material) is called a fluorescent host, and the host material combined with a phosphorescent dopant material (phosphorescent luminescent material) is called a phosphorescent host. The distinction between fluorescent and phosphorescent hosts is not solely based on molecular structure. That is, a phosphorescent host refers to a material that forms a phosphorescent luminescent layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material to form a fluorescent luminescent layer. The same applies to fluorescent hosts.

[0917] substrate

[0918] The substrate serves as a support for the organic EL element. There are no particular limitations on the substrate; for example, plates made of glass, quartz, or plastic can be used. Flexible substrates can also be used. There are no particular limitations on the flexible substrate; examples include plastic substrates formed from polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. Inorganic vapor-deposited films can also be used.

[0919] anode

[0920] The anode formed on the substrate is not particularly limited, but metals, alloys, conductive compounds, or mixtures thereof with a high work function (specifically 4.0 eV or higher) are preferred. Specifically, examples 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. Furthermore, examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), and nitrides of the above metals (e.g., titanium nitride).

[0921] 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.

[0922] Hole transport region

[0923] 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.

[0924] 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.

[0925] 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 their alloys (e.g., MgAg, AlLi); rare earth metals such as europium (Eu) and ytterbium (Yb) and their alloys; and so on. 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.

[0926] Hole injection layer

[0927] 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.

[0928] The hole-injection material is not particularly limited to the inventive compound, and examples include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.

[0929] 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.

[0930] 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.

[0931] In addition, acceptor materials such as hexaazabenzophenanthrene (HAT) compounds represented by the following formula (K) are also preferred.

[0932] [Chemical Formula 143]

[0933]

[0934] (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 R223 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-.

[0935] As R 227 There are no specific limitations; examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, etc.

[0936] 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 a 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 not particularly limited, but is preferably 0.01% by mass or more and less than 50% by mass, more preferably 0.05% by mass to 30% by mass, even more preferably 0.10% by mass to 10% by mass, even more preferably 0.50% by mass to 5% by mass, and particularly preferably 1.0% by mass to 3% by mass.

[0937] Examples of first organic materials include the inventive compound or other hole-injecting materials mentioned above.

[0938] In one embodiment of the organic EL element, the second organic material is not particularly limited, and for example, it is a compound containing 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).

[0939] [Chemical Formula 144]

[0940]

[0941] (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.)

[0942] =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).

[0943] [Chemical Formula 145]

[0944]

[0945] [Chemical Formula 146]

[0946]

[0947] (In the above general formulas (11a), (11b), (11c), (11d), (11e), (11f), (11g), (11h), (11i), (11j), (11k) or (11m), R 11 ~R 14 and R 1101 ~R 1110 Each independently

[0948] hydrogen atom,

[0949] Halogen atoms,

[0950] hydroxyl,

[0951] cyano,

[0952] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0953] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0954] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0955] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0956] -O-(R 904 The groups shown in the figure,

[0957] -S-(R 905 The groups shown in the figure,

[0958] -N(R 906 (R) 907 The groups shown in the figure,

[0959] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms or

[0960] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[0961] (In the above general formula (P12), Z1 to Z5 are each independently...)

[0962] nitrogen atoms,

[0963] With R 15 Bonded carbon atoms, or

[0964] Carbon atoms bonded to other atoms in the molecule of the second organic material mentioned above,

[0965] 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.

[0966] R 15 Freedom of choice

[0967] hydrogen atom,

[0968] Halogen atoms,

[0969] cyano,

[0970] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0971] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0972] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0973] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms

[0974] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms

[0975] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0976] -O-(R 904 The groups shown in the figure,

[0977] -S-(R 905 The groups shown in the figure,

[0978] -N(R 906 (R) 907 The groups shown in the figure,

[0979] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0980] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0981] carboxyl,

[0982] Substituted or unsubstituted ester groups

[0983] Substituted or unsubstituted carbamoyl group,

[0984] Nitro, and

[0985] The group consisting of substituted or unsubstituted siloxanyl groups.

[0986] In R15 In the case of multiple Rs, multiple Rs 15 (They may be the same or different.)

[0987] (In the second organic material mentioned above, R) 901 ~R 907 Each independently

[0988] hydrogen atom,

[0989] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0990] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0991] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0992] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0993] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.

[0994] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.

[0995] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.

[0996] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.

[0997] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.

[0998] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.

[0999] In R 907 In the case of multiple Rs, multiple Rs 907 (They may be the same or different.)

[1000] 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.

[1001] As used in this specification, the alkyl ester group is not particularly limited, for example, it can be formed by -C(=O)OR E Indicated. As R EThere are no particular limitations; for example, substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms (preferably 1 to 10 carbon atoms) can be cited.

[1002] As used in this specification, aryl ester groups are not particularly limited, for example, those derived from -C(=O)OR Ar Indicated. As R Ar There are no particular limitations; for example, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms can be cited.

[1003] In this specification, siloxane refers to a silicon compound group containing an ether bond. There is no particular limitation on the type of siloxane; for example, trimethylsiloxane can be cited.

[1004] In this specification, the carbamoyl group is represented by -CONH2.

[1005] The substituted carbamoyl group used in this specification is not particularly limited, and for example, can be derived from -CONH-Ar C -CONH-R C etc. indicates. As Ar C There are no particular limitations; examples include aryl groups with 6 to 50 cyclic carbon atoms (preferably 6 to 10 cyclic carbon atoms) and heterocyclic groups with 5 to 50 cyclic atoms (preferably 5 to 14 cyclic atoms), whether substituted or unsubstituted. Additionally, Ar... 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.

[1006] As R C There are no particular limitations; for example, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms (preferably 1 to 6 carbon atoms) can be cited.

[1007] In the second organic material described above, it is preferred that the groups described as "substituted or unsubstituted" are all "unsubstituted" groups.

[1008] The second organic material is not particularly limited, and examples include the following compounds. However, the present invention is not limited to specific examples of these second organic materials.

[1009] [Chemical Formula 147]

[1010]

[1011] [Chemical Formula 148]

[1012]

[1013] Hole transport layer

[1014] 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.

[1015] 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.

[1016] 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.

[1017] In one embodiment of the organic electroluminescent device of the present invention, one or both of the first hole transport layer and the second hole transport layer contain 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 layer selected from the first to third hole transport layers contains 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.

[1018] 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.

[1019] There are no particular limitations on hole transport layer materials other than the inventive compound; for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be cited.

[1020] As aromatic amine compounds, there are no particular limitations; examples include: 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated as BAFLP), 4,4'-bis[N-(9,9]... [-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), etc. The above compounds have 10 -6 cm 2 Hole mobility above / Vs.

[1021] As a carbazole derivative, there are no particular limitations. Examples include 4,4'-bis(9-carbazolyl)biphenyl (abbreviated as CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviated as CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (abbreviated as PCzPA).

[1022] As anthracene derivatives, there are no particular limitations. Examples 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).

[1023] Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) can also be used.

[1024] Among them, any compound whose hole transport capability is higher than its electron transport capability can use compounds other than those mentioned above.

[1025] 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).

[1026] [Chemical Formula 149]

[1027]

[1028] In equations (21) and (22) above,

[1029] L A1 L B1 L C1 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.

[1030] k can be 1, 2, 3, or 4.

[1031] 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.

[1032] When k is 2, 3, or 4, multiple L E2 They are the same or different.

[1033] 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.

[1034] 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.

[1035] 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 ),

[1036] 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.

[1037] In R' 901In the case of multiple R's, multiple R's 901 They are the same or different.

[1038] In R' 902 In the case of multiple R's, multiple R's 902 They are the same or different.

[1039] In R' 903 In the case of multiple R's, multiple R's 903 They are the same or different.

[1040] 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).

[1041] In equations (21) and (22), A is... 1 B 1 C 1 A 2 B 2 C 2 and D 2 Without particular limitation, it is preferred that each is independently 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, or substituted or unsubstituted carbazoyl.

[1042] 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 terphenyl, 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.

[1043] A 1 B 1 C 1 A 2 B 2 C 2 and D 2The 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.

[1044] As L A1 L B1 L C1 L A2 L B2 L C2 and L D2 There are no particular limitations, but it is preferred that each of the aryl groups is a single bond, substituted or unsubstituted, and has 6 to 12 carbon atoms in the cyclic group.

[1045] As specific examples of the compounds shown in formulas (21) and (22), the following compounds can be cited.

[1046] [Chemical Formula 150]

[1047]

[1048] dopant material of the light-emitting layer

[1049] The luminescent layer is a layer containing a highly luminescent material (dopant material), and various materials can be used. For example, fluorescent and phosphorescent materials can be used as dopant materials. Fluorescent materials are compounds that emit light using a singlet excited state, while phosphorescent materials are compounds that emit light using a triplet excited state.

[1050] In one embodiment of the organic EL element involved in this invention, the light-emitting layer preferably comprises a fluorescent dopant material (fluorescent light-emitting material).

[1051] In addition, in one embodiment of the organic EL element of the present invention, the light-emitting layer preferably comprises a phosphorescent dopant material (phosphorescent luminescent material).

[1052] Furthermore, in one embodiment of the organic EL element involved in this invention, it is preferred that the light-emitting layer is a single layer.

[1053] 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.

[1054] There are no particular limitations on blue fluorescent luminescent materials that can be used in the luminescent layer. Examples include pyrene derivatives, styrylamine derivatives, α-pyrene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, azaborane derivatives, and arylborane derivatives. Specifically, examples include N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenyl zirconia-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).

[1055] As a green fluorescent material that can be used in the light-emitting layer, there are no particular limitations; for example, aromatic amine derivatives can be cited. 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.

[1056] There are no particular limitations on red-based fluorescent materials that can be used in the luminescent layer; examples include tetraphenyl derivatives and diamine derivatives. 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).

[1057] In one embodiment of the present invention, the light-emitting layer preferably comprises a fluorescent light-emitting material (fluorescent dopant material).

[1058] There are no particular limitations on blue phosphorescent materials that can be used in the luminescent layer; examples include metal complexes such as iridium complexes, osmium complexes, and platinum complexes. 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).

[1059] As a green phosphorescent material that can be used in the light-emitting layer, there are no particular limitations; for example, iridium complexes can be cited. 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)).

[1060] As a red phosphorescent material that can be used in the luminescent layer, there are no particular limitations. For example, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes can be cited. 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 cited.

[1061] 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).

[1062] The main material of the light-emitting layer

[1063] 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 the dopant material and a higher occupied orbital level (HOMO level) lower than the dopant material is used.

[1064] As the main material, there are no particular limitations; for example, the following can be cited:

[1065] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes;

[1066] (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives;

[1067] (3) Carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or β-derived fused aromatic compounds;

[1068] (4) Aromatic amine compounds such as triarylamine derivatives and fused polycyclic aromatic amine derivatives; etc.

[1069] 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.

[1070] Specific examples of anthracene derivatives are described below.

[1071] Specific examples of anthracene derivatives include: 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), bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ), and other metal complexes.

[1072] 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), phenanthrene-rhein (abbreviation: BPhen), and copper bath (abbreviation: BCP);

[1073] 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,

[1074] 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-9 Aromatic amine compounds such as H-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); etc. Two or more host materials can be used.

[1075] In particular, in the case of blue fluorescent elements, the following anthracene derivatives are preferred as the main material.

[1076]

Chemical Formula 151

[1077]

[1078]

Chemical Formula 152

[1079]

[1080]

Chemical Formula 153

[1081]

[1082] [Chemical Formula 154]

[1083]

[1084] 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.

[1085] In the organic EL element of this embodiment, the light-emitting layer may include a layer containing a luminescent compound that exhibits fluorescence emission with a main peak wavelength of less than 500 nm.

[1086] 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.

[1087] 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).

[1088] 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.

[1089] 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.

[1090] 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. Then, 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.

[1091] Electron transport layer

[1092] 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.

[1093] 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.

[1094] As an electron transport layer, there are no particular limitations; for example, one could cite...

[1095] (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes;

[1096] (2) Imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, phenanthroline derivatives and other heteroaromatic compounds;

[1097] (3) Polymer compounds; etc.

[1098] As metal complexes, there are no particular limitations. Examples 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).

[1099] As heteroaromatic compounds, there are no particular limitations. Examples 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), etc.

[1100] As a polymer compound, there are no particular limitations. Examples 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).

[1101] 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.

[1102] Electron injection layer

[1103] An electron injection layer is a layer containing materials with high electron injection capability. 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 can be used in the electron injection layer. Such compounds are not particularly limited and can include, for example: alkali metal oxides; alkali metal halides; organic complexes containing alkali metals such as (8-hydroxyquinoline)lithium (Liq); alkaline earth metal oxides; alkaline earth metal halides; organic complexes containing alkaline earth metals; rare earth metal oxides; rare earth metal halides; organic complexes containing rare earth metals; and so on. Furthermore, multiple such compounds can be used in combination.

[1104] 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.

[1105] Alternatively, the electron injection layer can also be a composite material formed 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 not particularly limited, but materials that excel in the transport of the accepted electrons are preferred. Specifically, materials constituting the electron transport layer, such as those described above (metal complexes, heteroaromatic compounds, etc.), can be used. The electron donor is any material that exhibits electron-donating properties to the organic compound. The electron donor is not particularly limited, but alkali metals, alkaline earth metals, and rare earth metals are preferred, and alkali metal oxides and alkaline earth metal oxides are more preferred. The alkali metals, alkaline earth metals, and rare earth metals are not particularly limited, and examples include lithium, cesium, magnesium, calcium, erbium, and ytterbium. The alkali metal oxides and alkaline earth metal oxides are not particularly limited, and examples include lithium oxides, calcium oxides, and barium oxides. Additionally, Lewis bases such as magnesium oxide can also be used. Furthermore, organic compounds such as tetrathiofulvalene (TTF) can also be used.

[1106] cathode

[1107] There are no particular limitations on the cathode material, but metals, alloys, conductive compounds, and mixtures thereof with low work functions (specifically below 3.8 eV) are preferred. 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; and so on.

[1108] 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.

[1109] 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.

[1110] Insulation layer

[1111] 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.

[1112] There are no particular limitations on the materials that can be used in the insulating layer. Examples 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.

[1113] Spacer layer

[1114] 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.

[1115] 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.

[1116] Barrier layer

[1117] 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.

[1118] The layers of the aforementioned organic EL element can be formed using conventionally known methods such as vapor deposition and coating. Vapor deposition is not particularly limited; examples include known methods such as vacuum vapor deposition and molecular beam evaporation (MBE). Coating is also not particularly limited; examples include known methods such as dip coating, spin coating, casting, rod coating, and roll coating using a solution of the compound forming the layer.

[1119] 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, 5nm to 10μm is preferred, and 10nm to 0.2μm is more preferred.

[1120] 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, preferably 40 nm or more and 130 nm or less.

[1121] In addition, 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 25 nm or more, more preferably 35 nm or more, and preferably 100 nm or less.

[1122] In addition, 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 25 nm or more, more preferably 30 nm or more, and preferably 100 nm or less.

[1123] In addition, 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 0.5 < D2 / D1 < 3.5, and more preferably 0.75 < D2 / D1 < 3.0.

[1124] Examples of embodiments of the organic EL element of the present invention include:

[1125] As an organic EL element having the hole transport layer composed of the above two layers and

[1126] • 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;

[1127] The first hole transport layer and the second hole transport layer both comprise the second embodiment of the compound of the present invention;

[1128] • 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;

[1129] As an organic EL element having a hole transport layer consisting of the above three layers and

[1130] 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;

[1131] 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;

[1132] 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;

[1133] • 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;

[1134] • 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;

[1135] • 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;

[1136] • The first to third hole transport layers all contain the compound of the present invention in the tenth embodiment; etc.

[1137] electronic devices

[1138] 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.

[1139] In one aspect of the invention, it is preferred that the electronic device includes an organic electroluminescent element.

[1140] Example

[1141] The present invention will be described in more detail below using examples, but the present invention is not limited to the following examples.

[1142] The inventive compounds used in the manufacture of the organic EL elements in Examples 1-17

[1143]

Chemical Formula 155

[1144]

[1145] [Chemical Formula 156]

[1146]

[1147] [Chemical Formula 157]

[1148]

[1149] [Chemical Formula 158]

[1150]

[1151] The comparative compounds used in the manufacture of the organic EL elements in Comparative Examples 1-6

[1152] [Chemical Formula 159]

[1153]

[1154] [Chemical Formula 160]

[1155]

[1156]

Chemical Formula 161

[1157]

[1158]

Chemical Formula 162

[1159]

[1160] [Chemical Formula 163]

[1161]

[1162] Other compounds used in the manufacture of organic EL elements in Examples 1-17 and Comparative Examples 1-6

[1163] [Chemical Formula 164]

[1164]

[1165] [Chemical Formula 165]

[1166]

[1167] Fabrication of organic EL components

[1168] Example 1

[1169] 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.

[1170] 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.

[1171] Next, compound HT-1 was deposited on the hole injection layer to form the first hole transport layer with a thickness of 80 nm.

[1172] Next, compound HT-2 (compound Inv-1) was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 10 nm.

[1173] 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 25 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 96:4.

[1174] Next, compound ET-1 was deposited on the light-emitting layer to form a first electron transport layer with a thickness of 5 nm.

[1175] 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 20 nm. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50.

[1176] Next, LiF was deposited on the second electron transport layer to form an electron injection electrode with a film thickness of 1 nm.

[1177] Then, metallic Al was deposited on the electron-injecting electrode to form a metal cathode with a film thickness of 50 nm.

[1178] The following shows the layer configuration of the organic EL element of Example 1 obtained by such operation.

[1179] ITO(130) / HT-1:HA=97:3(10) / HT-1(80) / HT-2(10) / BH-1:BD-1=96:4(25) / ET-1(5) / ET-2:Liq=50:50(20) / LiF(1) / Al(50)

[1180] In the above layer composition, the numbers in parentheses are film thicknesses (nm), and the ratios are mass ratios.

[1181] Example 2

[1182] The organic EL element was fabricated in the same manner as in Example 1, except that compound Inv-2 was used instead of compound Inv-1.

[1183] Example 3

[1184] Organic EL elements were fabricated in the same manner as in Example 1, except that compound Inv-3 was used instead of compound Inv-1.

[1185] Example 4

[1186] The organic EL element was fabricated in the same manner as in Example 1, except that compound Inv-4 was used instead of compound Inv-1.

[1187] Example 5

[1188] Organic EL elements were fabricated in the same manner as in Example 1, except that compound Inv-5 was used instead of compound Inv-1.

[1189] Example 6

[1190] The organic EL element was fabricated in the same manner as in Example 1, except that compound Inv-6 was used instead of compound Inv-1.

[1191] Example 7

[1192] The organic EL element was fabricated in the same manner as in Example 1, except that compound Inv-7 was used instead of compound Inv-1.

[1193] Example 8

[1194] The organic EL element was fabricated in the same manner as in Example 1, except that compound Inv-8 was used instead of compound Inv-1.

[1195] Example 9

[1196] Organic EL elements were fabricated in the same manner as in Example 1, except that compound Inv-9 was used instead of compound Inv-1.

[1197] Example 10

[1198] Organic EL elements were fabricated in the same manner as in Example 1, except that compound Inv-10 was used instead of compound Inv-1.

[1199] Example 11

[1200] Organic EL elements were fabricated in the same manner as in Example 1, except that compound Inv-11 was used instead of compound Inv-1.

[1201] Example 12

[1202] Organic EL elements were fabricated in the same manner as in Example 1, except that compound Inv-12 was used instead of compound Inv-1.

[1203] Example 13

[1204] Organic EL elements were fabricated in the same manner as in Example 1, except that compound Inv-13 was used instead of compound Inv-1.

[1205] Example 14

[1206] Organic EL elements were fabricated in the same manner as in Example 1, except that compound Inv-14 was used instead of compound Inv-1.

[1207] Example 15

[1208] Organic EL elements were fabricated in the same manner as in Example 1, except that compound Inv-15 was used instead of compound Inv-1.

[1209] Example 16

[1210] Organic EL elements were fabricated in the same manner as in Example 1, except that compound Inv-16 was used instead of compound Inv-1.

[1211] Example 17

[1212] Organic EL elements were fabricated in the same manner as in Example 1, except that compound Inv-17 was used instead of compound Inv-1.

[1213] Comparative Example 1

[1214] The organic EL element was fabricated in the same manner as in Example 1, except that compound Ref-1 was used instead of compound Inv-1.

[1215] Comparative Example 2

[1216] The organic EL element was fabricated in the same manner as in Example 1, except that compound Ref-2 was used instead of compound Inv-1.

[1217] Comparative Example 3

[1218] The organic EL element was fabricated in the same manner as in Example 1, except that compound Ref-3 was used instead of compound Inv-1.

[1219] Comparative Example 4

[1220] Organic EL elements were fabricated in the same manner as in Example 1, except that compound Ref-4 was used instead of compound Inv-1.

[1221] Comparative Example 5

[1222] The organic EL element was fabricated in the same manner as in Example 1, except that compound Ref-5 was used instead of compound Inv-1.

[1223] Comparative Example 6

[1224] The organic EL element was fabricated in the same manner as in Example 1, except that compound Ref-6 was used instead of compound Inv-1.

[1225] Evaluation of organic EL devices

[1226] Determination of Component Life (LT95)

[1227] The obtained organic EL device was subjected to a current density of 50 mA / cm². 2 DC drive is used to measure the time (h) until the brightness drops to 95% of the initial brightness, and this time is taken as the 95% lifetime (LT95).

[1228] The results are shown in Tables 1 and 2.

[1229] Specific deuteration rate

[1230] Calculation of a specific deuteration rate

[1231] The proportion of deuterium atoms in the total hydrogen atoms (excluding hydrogen atoms in alkyl groups) of the inventive compound is calculated using the structural formula of the inventive compound and the following formula.

[1232] Specific deuteration rate = (Total number of D atoms - D atoms excluding methyl groups) / {(Total number of H atoms - H atoms excluding methyl groups) + (Total number of D atoms - D atoms excluding methyl groups)}

[1233] The results are shown in Tables 1 and 2.

[1234] Table 1

[1235]

[1236] Table 2

[1237]

[1238] As can be clearly seen from the results in Tables 1 and 2, the compounds that meet the requirements of this invention (compounds Inv-1 to Inv-17) provide organic EL devices with significantly improved device lifetime compared to the compounds that do not meet the requirements of this invention (compounds Ref-1 to Ref-6).

[1239] It should be noted that Tables 1 and 2 show the relative values ​​(%) of the 95% lifetime (LT95) of Examples 1-17 and Comparative Examples 2-6 relative to the 95% lifetime (LT95) of Comparative Example 1 when 100 is taken as 100.

[1240] The inventive compound synthesized in the synthetic example

[1241]

Chemical Formula 166

[1242]

[1243] [Chemical Formula 167]

[1244]

[1245] [Chemical Formula 168]

[1246]

[1247] Synthesis Example 1: Synthesis of Inv-1

[1248] [Chemical Formula 169]

[1249]

[1250] Under an argon atmosphere, 1-chloro-9,9-dimethyl-9H-fluorene (2.29 g, 10.0 mmol) as raw material 1 and N-[4-(1-naphthyl)(2,5- fluorene] as raw material 2 were used. 2 [H2]phenyl][1,1'-biphenyl]-4-amine (3.73 g, 10.0 mmol), tris(dibenzylacetone)dipalladium(0)(Pd2(dba)3) (0.183 g, 0.2 mmol) as catalyst, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos) (0.381 g, 0.8 mmol) as ligand, and xylene (50 mL) were added to the flask. Then, a 1M xylene solution of lithium bis(trimethylsilyl)amide (LHMDS) (10 mmol, 10 mL) as base was slowly added to the system. The mixture was then heated under reflux with stirring for 8 hours. After cooling to room temperature (25 °C) after stirring, the solvent was removed by distillation. The residue was purified by silica gel column chromatography and recrystallization to give 1.0 g of a white solid (yield 18%).

[1251] The white solid was identified as compound Inv-1 by LC-MS (liquid chromatography-mass spectrometry).

[1252] Synthesis Examples 2-17: Synthesis of Inv-2 to Inv-17

[1253] Inv-2 to Inv-17 were synthesized using the same method as in Synthesis Example 1, except that raw materials 1 and 2 in Synthesis Example 1 were replaced with the compounds shown in Tables 3 and 4 below.

[1254] Table 3

[1255]

[1256] Table 4

[1257]

[1258] Symbol Explanation

[1259] 1, 11, 12 Organic EL elements

[1260] 2 substrate

[1261] 3 Anode

[1262] 4 Cathode

[1263] 5. Light-emitting layer

[1264] 6. Hole transport region (hole transport layer)

[1265] 6a Hole injection layer

[1266] 6b Hole Transport Layer 1

[1267] 6c Hole transport layer 2

[1268] 6d Third Hole Transport Layer

[1269] 7. Electron transport region (electron transport layer)

[1270] 7a First electron transport layer

[1271] 7b Second electron transport layer

[1272] 10, 20, 30 light-emitting units

Claims

1. The compound represented by the following formula (1), wherein, In equation (1), N ＊ The central nitrogen atom, R 1 ~R 7 Each is independently a hydrogen atom or an unsubstituted phenyl group, selected from R 1 ~R 7 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. R c and R d Each is independently a protium atom, or a methyl group having three protium atoms, R c With R d They do not bond with each other and therefore do not form a ring. L 1 and L 2 Each is an independent single bond or an unsubstituted aryl group with 6 to 12 carbon atoms in a cyclic formation. Ar 1 and Ar 2 Each can be independently represented by the following formulas (2A), (2B), (2C), (2D), or (2E). Except R c and R d At least one of the hydrogen atoms other than the hydrogen atom in the atom is a deuterium atom. In equation (2A), *21 indicates the relationship with L 1 or 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, which is not the single bond mentioned above. 106 ~R 110 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 9 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms. R 111 ~R 115 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 9 carbon atoms, or a substituted or unsubstituted aryl group having 7 to 11 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. 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 or 1, k is 0 or 1, and when j = 1 and k = 1, L is bonded to *21. 1 or L 2 Not unsubstituted phenylene, in the case of j=1, k=0, L bonded to *21 1 or L 2 The divalent group, not derived by removing one hydrogen atom from an unsubstituted biphenyl group, is bonded to *21 when j=0 and k=1. 1 or L 2 It is not a divalent group derived by removing one hydrogen atom from an unsubstituted biphenyl group. 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 1 or 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 of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 9 carbon atoms, or a substituted or unsubstituted aryl 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. Among them, L bonded to *24 1 or L 2 When it is an unsubstituted phenylene, (i) is not the R of the single bond. 121 ~R 128 All are hydrogen atoms, or (ii) are not the single bonds described above. 121 ~R 128 One of them is an unsubstituted phenyl group and is not the single bond and the R of the unsubstituted phenyl group. 121 ~R 128 All are hydrogen atoms. In equation (2C), *26 indicates the relationship with L 1 or L 2 The bond, Selected from R 131 ~R 140 One of them is a single bond that bonds with *27. Not the R of the single bond 131 ~R 140 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 9 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms. Selected from R which is not the single bond described 131 ~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 1 or L 2 The bond, X 1 For oxygen atoms, or CR a R b , p is 0 or 1, where in X 1 When the atom is oxygen, p is 1. R a and R b Each is independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted cyclic aryl group having 6 to 12 carbon atoms, in R a and R b When at least one of them is methyl, R a and R b In at least one of the methyl groups, all hydrogen atoms are protium atoms, R a With R b They do not bond with each other and therefore do not form a ring. When p is 0, the selection is from R. 141 ~R 148 One of them is a single bond that bonds with *29. When p is 1, R 145 With R 146 R 146 With R 147 Or R 147 With R 148 When one of the bonds is a single bond bonded to *e and the other is a single bond bonded to *f, the R bond is selected from the single bond that is not bonded to either *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 And R, which is not the single bond mentioned above. 200 ~R 203 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 9 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 carbon atoms. In X 1 For CR a R b And R 141 Or R 148 When R is a single bond that bonds with *29, a and R b At least one of them is a substituted or unsubstituted aryl group with 6 to 12 carbon atoms in a cyclic ring. 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 1 or 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 R 161 ~R 165 and R 171 ~R 175 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 cycloalkyl group having 3 to 9 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms. 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. Selected from R 161 ~R 165 At least one pair of adjacent 2 elements in the structure do not bond to each other and therefore do not form a loop. Selected from R 171 ~R 175 At least one pair of adjacent 2 elements in the ring do not bond to each other and do not form a ring.

2. The compound according to claim 1, wherein, Ar 1 and Ar 2 Each is independently represented by the formulas (2A), (2B) or (2D).

3. The compound according to claim 1 or 2, wherein, Ar 1 and Ar 2 Each is independently represented by equation (2A) or (2B).

4. The compound according to any one of claims 1 to 3, wherein, Ar 1 and Ar 2 X in any of the expressions (2D) 1 For CR a R b .

5. The compound according to any one of claims 1 to 4, wherein, L 1 It is an unsubstituted phenylene.

6. The compound according to any one of claims 1 to 5, wherein, L 2 It is an unsubstituted phenylene.

7. The compound according to any one of claims 1 to 6, wherein, The compound represented by formula (1) has a total hydrogen atom content of more than 14.5% deuterium atoms in its aryl group, and the total hydrogen atoms do not include hydrogen atoms in the alkyl group.

8. A material for an organic electroluminescent element comprising any one of claims 1 to 7.

9. An organic electroluminescent element having a cathode, an anode, and an organic layer disposed between the cathode and the anode, the organic layer comprising a light-emitting layer, at least one layer of the organic layer comprising a compound according to any one of claims 1 to 8.

10. The organic electroluminescent element according to claim 9, wherein, The organic layer includes a hole transport region located between the anode and the light-emitting layer, and the hole transport region contains the compound.

11. The organic electroluminescent element according to claim 10, 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. One or both of the first hole transport layer and the second hole transport layer contain the compound.

12. The organic electroluminescent element according to any one of claims 9 to 11, wherein, The light-emitting layer contains fluorescent dopant material.

13. The organic electroluminescent element according to any one of claims 9 to 11, wherein, The light-emitting layer contains phosphorescent dopant material.

14. An electronic device comprising an organic electroluminescent element according to any one of claims 9 to 13.

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