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

Abstract

Provided are a compound represented by formula (1), an organic electroluminescent element comprising the compound, and an electronic device comprising the organic electroluminescent element. Each symbol in formula (1) is the same as defined in the description. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a compound, a material for an organic electroluminescent element, an organic electroluminescent element, and an electronic device including the organic electroluminescent element. Background Art

[0002] Generally, an organic electroluminescent element (hereinafter sometimes also referred to as "organic EL element") is composed of an anode, a cathode, and an organic layer sandwiched between the anode and the cathode. When a voltage is applied between the two electrodes, electrons are injected from the cathode side into the light-emitting region, and holes are injected from the anode side into the light-emitting region. The injected electrons and holes recombine in the light-emitting region to generate an excited state, and light is emitted when the excited state returns to the ground state. Therefore, it is important to find a material combination that can efficiently transport electrons or holes to the light-emitting region and facilitate the recombination of electrons and holes so that excitons can emit light efficiently in obtaining a high-performance organic EL element.

[0003] Compounds used as materials for organic electroluminescent elements are disclosed in Patent Documents 1 to 5.

[0004] Prior Art Documents

[0005] Patent Documents

[0006] Patent Document 1: US Patent Application Publication No. 2012 / 0292576

[0007] Patent Document 2: US Patent Application Publication No. 2022 / 0199912

[0008] Patent Document 3: Korean Patent Publication No. 10-2017-0116974

[0009] Patent Document 4: Korean Patent Publication No. 10-2020-0136713

[0010] Patent Document 5: Korean Patent Publication No. 10-2020-0095104 Summary of the Invention

[0011] Problems to be Solved by the Invention

[0012] In the past, a large number of compounds for organic EL elements have been reported, but there is still a need to further improve the performance of organic EL elements.

[0013] The present invention has been made to solve the above problems, and an object thereof is to provide a compound that further improves the performance of an organic EL element, an organic EL element whose element performance is further improved, and an electronic device including such an organic EL element.

[0014] Means for Solving the Problems

[0015] The inventors of the present invention have repeatedly and deeply studied the performance of organic EL elements containing the compounds described in Patent Documents 1 to 5, and as a result, it has been found that the performance of organic EL elements containing the compound represented by the following formula (1) is further improved.

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

[0017] [Chemical formula 1]

[0018]

[0019] (In formula (1),

[0020] N* is a central nitrogen atom.

[0021] Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0022] L 1 and L 2 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[0023] L 3 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[0024] R 1 ~R 10 are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms, a group represented by -Si(R 901 )(R 902 )(R 903 ), a group represented by -O-(R 904 ), or a group represented by -S-(R 905 ),

[0025] R 901 ~R 905Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0026] In R 901 When there are two or more, two or more Rs 901 Are the same as or different from each other.

[0027] In R 902 When there are two or more, two or more Rs 902 Are the same as or different from each other.

[0028] In R 903 When there are two or more, two or more Rs 903 Are the same as or different from each other.

[0029] In R 904 When there are two or more, two or more Rs 904 Are the same as or different from each other.

[0030] In R 905 When there are two or more, two or more Rs 905 Are the same as or different from each other.

[0031] Among them, two adjacent ones selected from R2 to R 10 Can be bonded to each other to form a substituted or unsubstituted benzene ring, or may not be bonded to each other and thus do not form a ring.

[0032] X 1 Is an oxygen atom or a sulfur atom.)

[0033] In another aspect, the present invention provides a material for an organic EL element containing the compound represented by the above formula (1).

[0034] In yet another aspect, the present invention provides an organic electroluminescent element including a cathode, an anode, and an organic layer located between the cathode and the anode, the organic layer including a light-emitting layer, and at least one layer of the organic layer containing the compound represented by the above formula (1).

[0035] In yet another aspect, the present invention provides an electronic device including the above organic electroluminescent element.

[0036] Effects of the Invention

[0037] The organic EL element containing the compound represented by the above formula (1) exhibits improved element performance. Brief Description of the Drawings

[0038] Figure 1It is a schematic diagram showing an example of the layer structure of an organic EL element related to one aspect of the present invention.

[0039] Figure 2 It is a schematic diagram showing another example of the layer structure of an organic EL element related to one aspect of the present invention.

[0040] Figure 3 It is a schematic diagram showing yet another example of the layer structure of an organic EL element related to one aspect of the present invention. Detailed Description

[0041] [Definition]

[0042] In this specification, a hydrogen atom means an isotope containing a different number of neutrons, namely protium, deuterium, and tritium.

[0043] In this specification, in a chemical structural formula, when the bonding positions of symbols such as "R" and "D" representing deuterium atoms are not clearly shown, they are assumed to be bonded to a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom.

[0044] In this specification, the number of ring-forming carbon atoms refers to the number of carbon atoms among the atoms constituting the ring itself in a compound whose atoms are bonded in a ring structure (such as a monocyclic compound, a polycyclic compound, a bridged-ring compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbon atoms. The "number of ring-forming carbon atoms" described below is set in the same way unless otherwise specified. For example, the number of ring-forming carbon atoms of a benzene ring is 6, the number of ring-forming carbon atoms of a naphthalene ring is 10, the number of ring-forming carbon atoms of a pyridine ring is 5, and the number of ring-forming carbon atoms of a furan ring is 4. In addition, for example, the number of ring-forming carbon atoms of 9,9-diphenylfluorenyl is 13, and the number of ring-forming carbon atoms of 9,9'-spirobifluorenyl is 25.

[0045] In addition, when an alkyl group is substituted as a substituent on a benzene ring, for example, the number of carbon atoms of the alkyl group is not included in the number of ring-forming carbon atoms of the benzene ring. Therefore, the number of ring-forming carbon atoms of a benzene ring substituted with an alkyl group is 6. In addition, when an alkyl group is substituted as a substituent on a naphthalene ring, for example, the number of carbon atoms of the alkyl group is not included in the number of ring-forming carbon atoms of the naphthalene ring. Therefore, the number of ring-forming carbon atoms of a naphthalene ring substituted with an alkyl group is 10.

[0046] In this specification, the number of ring-forming atoms refers to the number of atoms that form a ring structure (such as single rings, fused rings, and ring assemblies) in compounds (such as monocyclic compounds, fused-ring compounds, bridged-ring compounds, carbocyclic compounds, and heterocyclic compounds). Atoms that do not form a ring (such as hydrogen atoms that cap the bonds of ring-forming atoms) and atoms contained in substituents when the ring is substituted are not included in the number of ring-forming atoms. The "number of ring-forming atoms" described below is set in the same way unless otherwise noted. For example, the number of ring-forming atoms in a pyridine ring is 6, the number of ring-forming atoms in a quinazoline ring is 10, and the number of ring-forming atoms in a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or the number of atoms that make up a substituent is not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms in a pyridine ring bonded with a hydrogen atom or a substituent is 6. Additionally, for example, hydrogen atoms bonded to carbon atoms in a quinazoline ring or atoms that make up a substituent are not included in the number of quinazoline ring-forming atoms. Therefore, the number of ring-forming atoms in a quinazoline ring bonded with a hydrogen atom or a substituent is 10.

[0047] In this specification, in the expression "ZZ group having XX to YY carbon atoms, which may be substituted or unsubstituted", "XX to YY carbon atoms" represents the number of carbon atoms when the ZZ group is unsubstituted, and the number of carbon atoms of the substituent when substitution occurs is not included. Here, "YY" is greater than "XX", "XX" refers to an integer of 1 or more, and "YY" refers to an integer of 2 or more.

[0048] In this specification, in the expression "ZZ group having XX to YY atoms, which may be substituted or unsubstituted", "XX to YY atoms" represents the number of atoms when the ZZ group is unsubstituted, and the number of atoms of the substituent when substitution occurs is not included. Here, "YY" is greater than "XX", "XX" refers to an integer of 1 or more, and "YY" refers to an integer of 2 or more.

[0049] In this specification, an unsubstituted ZZ group means the case where "ZZ group which may be substituted or unsubstituted" is an "unsubstituted ZZ group", and a substituted ZZ group means the case where "ZZ group which may be substituted or unsubstituted" is a "substituted ZZ group".

[0050] In this specification, when it is expressed as "ZZ group which may be substituted or unsubstituted", "unsubstituted" means that the hydrogen atoms in the ZZ group are not replaced by substituents. The hydrogen atoms in the "unsubstituted ZZ group" are protium atoms, deuterium atoms, or tritium atoms.

[0051] Additionally, in this specification, when it is expressed as "ZZ group which may be substituted or unsubstituted", "substituted" means that one or more hydrogen atoms in the ZZ group are replaced by substituents. When it is expressed as "BB group substituted by AA group", "substituted" also means that one or more hydrogen atoms in the BB group are replaced by the AA group.

[0052] "Substituents described in this specification"

[0053] The substituents described in this specification are described below.

[0054] The number of ring-forming carbon atoms of the "unsubstituted aryl" described in this specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified in this specification.

[0055] The number of ring-forming atoms of the "unsubstituted heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified in this specification.

[0056] The number of carbon atoms of the "unsubstituted alkyl" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified in this specification.

[0057] The number of carbon atoms of the "unsubstituted alkenyl" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified in this specification.

[0058] The number of carbon atoms of the "unsubstituted alkynyl" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified in this specification.

[0059] The number of ring-forming carbon atoms of the "unsubstituted cycloalkyl" described in this specification is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified in this specification.

[0060] The number of ring-forming carbon atoms of the "unsubstituted arylene" described in this specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified in this specification.

[0061] The number of ring-forming atoms of the "unsubstituted divalent heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified in this specification.

[0062] The number of carbon atoms of the "unsubstituted alkylene" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified in this specification.

[0063] · "Substituted or unsubstituted aryl"

[0064] As specific examples (specific example group G1) of the "substituted or unsubstituted aryl" described in this specification, the following unsubstituted aryls (specific example group G1A) and substituted aryls (specific example group G1B) etc. can be cited. (Here, the unsubstituted aryl means the case where the "substituted or unsubstituted aryl" is an "unsubstituted aryl", and the substituted aryl means the case where the "substituted or unsubstituted aryl" is a "substituted aryl".) In this specification, when only "aryl" is expressed, it includes both "unsubstituted aryl" and "substituted aryl".

[0065] The "substituted aryl" refers to a group in which one or more hydrogen atoms of the "unsubstituted aryl" have been replaced by substituents. As the "substituted aryl", for example, groups in which one or more hydrogen atoms of the "unsubstituted aryl" in the following specific example group G1A have been replaced by substituents, and examples of the substituted aryls in the following specific example group G1B etc. can be cited. It should be noted that the examples of the "unsubstituted aryl" and the "substituted aryl" listed here are only examples, and the "substituted aryl" described in this specification also includes groups in which the hydrogen atoms bonded to the carbon atoms of the aryl itself in the "substituted aryl" in the following specific example group G1B have been further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted aryl" in the following specific example group G1B have been further replaced by substituents.

[0066] · Unsubstituted aryl (specific example group G1A):

[0067] Phenyl,

[0068] p - Biphenylyl,

[0069] m - Biphenylyl,

[0070] o - Biphenylyl,

[0071] 4 - p - Terphenyl - yl,

[0072] 3 - p - Terphenyl - yl,

[0073] 2 - p - Terphenyl - yl,

[0074] 4 - m - Terphenyl - yl,

[0075] 3 - m - Terphenyl - yl,

[0076] 2 - m - Terphenyl - yl,

[0077] 4 - o - Terphenyl - yl,

[0078] 3 - o - Terphenyl - yl,

[0079] 2 - o - Terphenyl - yl,

[0080] 1 - Naphthyl,

[0081] 2-naphthyl

[0082] anthryl

[0083] benzoanthryl

[0084] phenanthryl

[0085] benzophenanthryl

[0086] phenalenyl

[0087] pyrenyl

[0088] -yl

[0089] benzo -yl

[0090] triphenylenyl

[0091] benzotriphenylenyl

[0092] tetracenyl

[0093] pentacenyl

[0094] fluorenyl

[0095] 9,9'-spirobifluorenyl

[0096] benzofluorenyl

[0097] dibenzofluorenyl

[0098] fluoranthenyl

[0099] benzofluoranthenyl

[0100] perylenyl, and

[0101] a monovalent aryl group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-1) to (TEMP-15).

[0102] [Chemical formula 2]

[0103]

[0104] [Chemical formula 3]

[0105]

[0106] · Substituted aryl (specific example group G1B): o-tolyl

[0107] m-tolyl

[0108] p-tolyl

[0109] p-xylyl

[0110] m - Xylyl

[0111] o - Xylyl

[0112] p - Isopropylphenyl

[0113] m - Isopropylphenyl

[0114] o - Isopropylphenyl

[0115] p - tert - Butylphenyl

[0116] m - tert - Butylphenyl

[0117] o - tert - Butylphenyl

[0118] 3,4,5 - Trimethylphenyl

[0119] 9,9 - Dimethylfluorenyl

[0120] 9,9 - Diphenylfluorenyl

[0121] 9,9 - Bis(4 - methylphenyl)fluorenyl

[0122] 9,9 - Bis(4 - isopropylphenyl)fluorenyl

[0123] 9,9 - Bis(4 - tert - butylphenyl)fluorenyl

[0124] Cyano - phenyl

[0125] Triphenylsilylphenyl

[0126] Trimethylsilylphenyl

[0127] Phenylnaphthyl

[0128] Naphthylphenyl, and

[0129] a group in which one or more hydrogen atoms of a monovalent group derived from the ring structures represented by the above general formulas (TEMP - 1) to (TEMP - 15) are replaced with substituents.

[0130] · “substituted or unsubstituted heterocyclic group”

[0131] The “heterocyclic group” described in this specification is a cyclic group containing at least one heteroatom in the ring - forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.

[0132] The “heterocyclic group” described in this specification is a monocyclic group or a polycyclic group.

[0133] The “heterocyclic group” described in this specification is an aromatic heterocyclic group or a non - aromatic heterocyclic group.

[0134] As specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification, the following unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B) can be cited. (Here, the unsubstituted heterocyclic group means the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group means the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when only "heterocyclic group" is expressed, it includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".

[0135] The "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of the "unsubstituted heterocyclic group" have been replaced by substituents. Specific examples of the "substituted heterocyclic group" can include groups in which the hydrogen atoms of the "unsubstituted heterocyclic group" in the following specific example group G2A have been substituted, and examples of the substituted heterocyclic group in the following specific example group G2B, etc. It should be noted that the examples of the "unsubstituted heterocyclic group" and the "substituted heterocyclic group" listed here are only examples, and the "substituted heterocyclic group" described in this specification also includes groups in which the hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself in the "substituted heterocyclic group" of specific example group G2B have been further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted heterocyclic group" of specific example group G2B have been further replaced by substituents.

[0136] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0137] Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of the monovalent heterocyclic groups derived from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) have been replaced by substituents (specific example group G2B4).

[0138] · Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):

[0139] Pyrrolyl,

[0140] Imidazolyl,

[0141] Pyrazolyl,

[0142] Triazolyl,

[0143] Tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, indazolyl, quinazolinyl, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, indazolyl, phenanthrolinyl, phenanthridinyl, acridinyl, phenazinyl, carbazolyl, benzocarbazolyl, morpholinyl,

[0144] Phenoxazinyl,

[0145] Phenothiazinyl,

[0146] Aza-carbazolyl, and diaza-carbazolyl.

[0147] · Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): Furyl,

[0148] Oxazolyl,

[0149] Isoxazolyl,

[0150] Oxadiazolyl,

[0151] Xanthenyl,

[0152] Benzofuryl,

[0153] Isobenzofuryl,

[0154] Dibenzofuryl,

[0155] Naphthobenzofuryl,

[0156] Benzoxazolyl,

[0157] Benzisoxazolyl,

[0158] Phenoxazinyl,

[0159] Morpholinyl,

[0160] Dinaphthofuryl,

[0161] Aza-dibenzofuryl,

[0162] Diaza-dibenzofuryl,

[0163] Aza-naphthobenzofuryl, and

[0164] Diaza-naphthobenzofuryl.

[0165] · Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): Thienyl,

[0166] Thiazolyl,

[0167] isothiazolyl,

[0168] thiadiazolyl,

[0169] benzothienyl,

[0170] isobenzothienyl,

[0171] dibenzothienyl,

[0172] naphthobenzothienyl,

[0173] benzothiazolyl,

[0174] benzoisothiazolyl,

[0175] phenothiazinyl,

[0176] dinaphthothienyl,

[0177] azadibenzothienyl,

[0178] diazadibenzothienyl,

[0179] azanaphthobenzothienyl and

[0180] diazanaphthobenzothienyl.

[0181] · A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0182] [Chemical formula 4]

[0183]

[0184] [Chemical formula 5]

[0185]

[0186] In the above general formulas (TEMP-16) to (TEMP-33), X A and YA are each independently an oxygen atom, a sulfur atom, NH or CH 2 . Among them, X A and Y AAt least one of them is an oxygen atom, a sulfur atom or NH.

[0187] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A at least any one of them is NH or CH 2 When this is the case, the monovalent heterocyclic group derived from the ring structure represented by the above general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH 2 · Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):

[0188] (9-Phenyl)carbazolyl,

[0189] (9-Biphenyl)carbazolyl,

[0190] (9-Phenyl)phenylcarbazolyl,

[0191] (9-Naphthyl)carbazolyl,

[0192] Diphenylcarbazol-9-yl,

[0193] Phenylcarbazol-9-yl,

[0194] Methylbenzimidazolyl,

[0195] Ethylbenzimidazolyl,

[0196] Phenyltriazinyl,

[0197] Biphenyltriazinyl,

[0198] Diphenyltriazinyl,

[0199] Phenylquinazolinyl, and

[0200] Biphenylquinazolinyl.

[0201] · Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0202] Phenyldibenzofuranyl,

[0203] Methyldibenzofuranyl,

[0204] tert-Butyldibenzofuranyl, and

[0205] The monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0206] · Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

[0207] Phenyldibenzothienyl,

[0208] ​

[0209] Methyldibenzothienyl,

[0210] tert-Butyldibenzothienyl, and

[0211] a monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0212] · A group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structures represented by the above general formulas (TEMP-16) to (TEMP-33) are replaced with substituents (specific example group G2B4):

[0213] The above "one or more hydrogen atoms of a monovalent heterocyclic group" refers to hydrogen atoms bonded to ring-forming carbon atoms of the monovalent heterocyclic group, hydrogen atoms bonded to nitrogen atoms when at least any one of X A and Y A is NH, and one or more hydrogen atoms of methylene hydrogen atoms when one of X A and Y A is CH 2 at that time.

[0214] · "Substituted or unsubstituted alkyl"

[0215] As specific examples (specific example group G3) of the "substituted or unsubstituted alkyl" described in this specification, the following unsubstituted alkyls (specific example group G3A) and substituted alkyls (specific example group G3B) can be cited. (Here, the unsubstituted alkyl refers to the case where the "substituted or unsubstituted alkyl" is an "unsubstituted alkyl", and the substituted alkyl refers to the case where the "substituted or unsubstituted alkyl" is a "substituted alkyl".) Hereinafter, when only "alkyl" is mentioned, it includes both "unsubstituted alkyl" and "substituted alkyl".

[0216] "Substituted alkyl" means a group in which one or more hydrogen atoms in "unsubstituted alkyl" have been replaced by substituents. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl" (specific example group G3A) have been replaced by substituents, examples of substituted alkyl (specific example group G3B), and the like. In this specification, the alkyl in "unsubstituted alkyl" refers to a linear alkyl. Therefore, "unsubstituted alkyl" includes "unsubstituted alkyl" as a straight chain and "unsubstituted alkyl" as a branched chain. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples, and the "substituted alkyl" described in this specification also includes groups in which the hydrogen atoms of the alkyl itself in the "substituted alkyl" of specific example group G3B have been further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted alkyl" of specific example group G3B have been further replaced by substituents.

[0217] · Unsubstituted alkyl (specific example group G3A):

[0218] Methyl,

[0219] Ethyl,

[0220] n-Propyl,

[0221] Isopropyl,

[0222] n-Butyl,

[0223] Isobutyl,

[0224] sec-Butyl, and

[0225] tert-Butyl.

[0226] · Substituted alkyl (specific example group G3B):

[0227] Heptafluoropropyl (including isomers),

[0228] Pentafluoroethyl,

[0229] 2,2,2-Trifluoroethyl, and

[0230] Trifluoromethyl.

[0231] · "Substituted or unsubstituted alkenyl"

[0232] As specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl" described in this specification, the following unsubstituted alkenyls (specific example group G4A) and substituted alkenyls (specific example group G4B) can be cited. (Here, the unsubstituted alkenyl refers to the case where the "substituted or unsubstituted alkenyl" is an "unsubstituted alkenyl", and the "substituted alkenyl" refers to the case where the "substituted or unsubstituted alkenyl" is a "substituted alkenyl".) In this specification, when only "alkenyl" is stated, it includes both "unsubstituted alkenyl" and "substituted alkenyl".

[0233] The "substituted alkenyl" refers to a group in which one or more hydrogen atoms in the "unsubstituted alkenyl" are replaced by substituents. As specific examples of the "substituted alkenyl", examples include groups in which the following "unsubstituted alkenyls" (specific example group G4A) have substituents and examples of substituted alkenyls (specific example group G4B). It should be noted that the examples of the "unsubstituted alkenyl" and the "substituted alkenyl" listed here are only examples, and the "substituted alkenyl" described in this specification also includes groups in which the hydrogen atoms of the alkenyl itself in the "substituted alkenyl" of specific example group G4B are further replaced by substituents and groups in which the hydrogen atoms of the substituents in the "substituted alkenyl" of specific example group G4B are further replaced by substituents.

[0234] · Unsubstituted alkenyl (specific example group G4A):

[0235] Vinyl,

[0236] Allyl,

[0237] 1-Butenyl,

[0238] 2-Butenyl, and

[0239] 3-Butenyl.

[0240] · Substituted alkenyl (specific example group G4B):

[0241] 1,3-Butadienyl,

[0242] 1-Methylvinyl,

[0243] 1-Methylallyl,

[0244] 1,1-Dimethylallyl,

[0245] 2-Methylallyl, and

[0246] 1,2-Dimethylallyl.

[0247] · "Substituted or unsubstituted alkynyl"

[0248] As a specific example (specific example group G5) of the "substituted or unsubstituted alkynyl" described in this specification, the following unsubstituted alkynyl (specific example group G5A) etc. can be cited. (Here, the unsubstituted alkynyl means the case where the "substituted or unsubstituted alkynyl" is an "unsubstituted alkynyl".) When only expressed as "alkynyl" hereinafter, both "unsubstituted alkynyl" and "substituted alkynyl" are included.

[0249] "Substituted alkynyl" means a group in which one or more hydrogen atoms in the "unsubstituted alkynyl" are replaced by substituents. As a specific example of the "substituted alkynyl", a group in which one or more hydrogen atoms in the following "unsubstituted alkynyl" (specific example group G5A) are replaced by substituents etc. can be cited.

[0250] · Unsubstituted alkynyl (specific example group G5A):

[0251] Ethynyl

[0252] · "Substituted or unsubstituted cycloalkyl"

[0253] As a specific example (specific example group G6) of the "substituted or unsubstituted cycloalkyl" described in this specification, the following unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B) etc. can be cited. (Here, the unsubstituted cycloalkyl means the case where the "substituted or unsubstituted cycloalkyl" is an "unsubstituted cycloalkyl", and the substituted cycloalkyl means the case where the "substituted or unsubstituted cycloalkyl" is a "substituted cycloalkyl".) In this specification, when only expressed as "cycloalkyl", both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.

[0254] "Substituted cycloalkyl" means a group in which one or more hydrogen atoms in the "unsubstituted cycloalkyl" are replaced by substituents. As a specific example of the "substituted cycloalkyl", a group in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl" (specific example group G6A) are replaced by substituents and examples of the substituted cycloalkyl (specific example group G6B) etc. can be cited. It should be noted that the examples of the "unsubstituted cycloalkyl" and the examples of the "substituted cycloalkyl" listed here are only one example, and the "substituted cycloalkyl" described in this specification also includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the cycloalkyl itself in the "substituted cycloalkyl" of the specific example group G6B are replaced by substituents and a group in which the hydrogen atoms of the substituents in the "substituted cycloalkyl" of the specific example group G6B are further replaced by substituents.

[0255] · Unsubstituted cycloalkyl (specific example group G6A):

[0256] Cyclopropyl,

[0257] Cyclobutyl,

[0258] Cyclopentyl,

[0259] Cyclohexyl,

[0260] 1 - Adamantyl,

[0261] 2 - Adamantyl,

[0262] 1 - Norbornyl, and

[0263] 2 - Norbornyl.

[0264] · Substituted cycloalkyl (specific example group G6B):

[0265] 4 - Methylcyclohexyl.

[0266] · The group represented by “-Si(R 901 )(R 902 )(R 903 )”

[0267] As specific examples (specific example group G7) of the group represented by -Si(R 901 )(R 902 )(R 903 ) described in this specification, there can be cited

[0268] -Si(G1)(G1)(G1),

[0269] -Si(G1)(G2)(G2),

[0270] -Si(G1)(G1)(G2),

[0271] -Si(G2)(G2)(G2),

[0272] -Si(G3)(G3)(G3) and

[0273] -Si(G6)(G6)(G6). Here,

[0274] G1 is the “substituted or unsubstituted aryl” described in specific example group G1.

[0275] G2 is the “substituted or unsubstituted heterocyclic group” described in specific example group G2.

[0276] G3 is the “substituted or unsubstituted alkyl” described in specific example group G3.

[0277] G6 is the “substituted or unsubstituted cycloalkyl” described in specific example group G6.

[0278] The multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other.

[0279] - The multiple G2s in -Si(G1)(G2)(G2) are the same as or different from each other.

[0280] - The multiple G1s in -Si(G1)(G1)(G2) are the same as or different from each other.

[0281] - The multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other.

[0282] - The multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other.

[0283] - The multiple G6s in -Si(G6)(G6)(G6) are the same as or different from each other.

[0284] · "The group represented by -O-(R 904 )"

[0285] As specific examples (specific example group G8) of the group represented by -O-(R 904 ) described in this specification, there can be cited

[0286] -O(G1),

[0287] -O(G2),

[0288] -O(G3) and

[0289] -O(G6).

[0290] Here,

[0291] G1 is the "substituted or unsubstituted aryl" described in specific example group G1.

[0292] G2 is the "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0293] G3 is the "substituted or unsubstituted alkyl" described in specific example group G3.

[0294] G6 is the "substituted or unsubstituted cycloalkyl" described in specific example group G6.

[0295] · "The group represented by -S-(R 905 )"

[0296] As specific examples (specific example group G9) of the group represented by -S-(R 905 ) described in this specification, there can be cited

[0297] -S(G1),

[0298] -S(G2),

[0299] -S(G3) and

[0300] -S(G6).

[0301] Here,

[0302] G1 is the "substituted or unsubstituted aryl" described in Specific Example Group G1.

[0303] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0304] G3 is the "substituted or unsubstituted alkyl" described in Specific Example Group G3.

[0305] G6 is the "substituted or unsubstituted cycloalkyl" described in Specific Example Group G6.

[0306] · The group represented by "-N(R 906 )(R 907 )"

[0307] As specific examples (Specific Example Group G10) of the group represented by -N(R 906 )(R 907 ) described in this specification, there can be cited

[0308] -N(G1)(G1),

[0309] -N(G2)(G2),

[0310] -N(G1)(G2),

[0311] -N(G3)(G3) and

[0312] -N(G6)(G6).

[0313] Here,

[0314] G1 is the "substituted or unsubstituted aryl" described in Specific Example Group G1.

[0315] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0316] G3 is the "substituted or unsubstituted alkyl" described in Specific Example Group G3.

[0317] G6 is the "substituted or unsubstituted cycloalkyl" described in Specific Example Group G6.

[0318] Multiple G1s in -N(G1)(G1) are the same as or different from each other.

[0319] Multiple G2s in -N(G2)(G2) are the same as or different from each other.

[0320] Multiple G3s in -N(G3)(G3) are the same as or different from each other.

[0321] - The multiple G6s in -N(G6)(G6) are the same as or different from each other.

[0322] · "Halogen atom"

[0323] As specific examples (specific example group G11) of the "halogen atom" described in this specification, fluorine atom, chlorine atom, bromine atom, iodine atom, etc. can be cited.

[0324] · "Substituted or unsubstituted fluoroalkyl"

[0325] The "substituted or unsubstituted fluoroalkyl" described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl" is replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl" are replaced by fluorine atoms (perfluoro group). The carbon number of the "unsubstituted fluoroalkyl" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. The "substituted fluoroalkyl" refers to a group in which one or more hydrogen atoms of the "fluoroalkyl" are replaced by substituents. It should be noted that the "substituted fluoroalkyl" described in this specification also includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the "substituted fluoroalkyl" are further replaced by substituents and a group in which one or more hydrogen atoms of the substituents in the "substituted fluoroalkyl" are further replaced by substituents. As specific examples of the "unsubstituted fluoroalkyl", examples of groups in which one or more hydrogen atoms in the above-mentioned "alkyl" (specific example group G3) are replaced by fluorine atoms can be cited.

[0326] · "Substituted or unsubstituted haloalkyl"

[0327] The "substituted or unsubstituted haloalkyl" described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl" is replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl" are replaced by halogen atoms. The carbon number of the "unsubstituted haloalkyl" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. The "substituted haloalkyl" refers to a group in which one or more hydrogen atoms of the "haloalkyl" are replaced by substituents. It should be noted that the "substituted haloalkyl" described in this specification also includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the "substituted haloalkyl" are further replaced by substituents, and a group in which one or more hydrogen atoms of the substituents in the "substituted haloalkyl" are further replaced by substituents. As a specific example of the "unsubstituted haloalkyl", examples include groups in which one or more hydrogen atoms in the above-mentioned "alkyl" (specific example group G3) are replaced by halogen atoms. Haloalkyl is sometimes referred to as haloalkyl group.

[0328] · "Substituted or unsubstituted alkoxy"

[0329] As a specific example of the "substituted or unsubstituted alkoxy" described in this specification, it is a group represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl" described in specific example group G3. The carbon number of the "unsubstituted alkoxy" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0330] · "Substituted or unsubstituted alkylthio"

[0331] As a specific example of the "substituted or unsubstituted alkylthio" described in this specification, it is a group represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl" described in specific example group G3. The carbon number of the "unsubstituted alkylthio" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0332] · "Substituted or unsubstituted aryloxy"

[0333] As a specific example of the "substituted or unsubstituted aryloxy" described in this specification, it is a group represented by -O(G1), where G1 is the "substituted or unsubstituted aryl" described in specific example group G1. The ring-forming carbon number of the "unsubstituted aryloxy" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0334] · "Substituted or unsubstituted arylthio"

[0335] As a specific example of the "substituted or unsubstituted arylthio group" described in this specification, it is a group represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. The ring-forming carbon number 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.

[0336] · "Substituted or unsubstituted trialkylsilyl"

[0337] As a specific example of the "trialkylsilyl" described in this specification, it is a group represented by -Si(G3)(G3)(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The plurality of G3 in -Si(G3)(G3)(G3) are the same as or different from each other. The carbon number of each alkyl group of the "trialkylsilyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.

[0338] · "Substituted or unsubstituted aralkyl"

[0339] As a specific example of the "substituted or unsubstituted aralkyl" described in this specification, it is a group represented by -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. Therefore, the "aralkyl" is a group in which a hydrogen atom of the "alkyl" is replaced by the "aryl" as a substituent, and is a scheme of the "substituted alkyl". The "unsubstituted aralkyl" is an "unsubstituted alkyl" substituted with an "unsubstituted aryl group". The carbon number of the "unsubstituted aralkyl" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.

[0340] As specific examples of the "substituted or unsubstituted aralkyl", 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 can be cited.

[0341] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group is preferably phenyl, p-biphenylyl, m-biphenylyl, o-biphenylyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, pyrenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, etc.

[0342] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic group is preferably pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, phenanthrolinyl, carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl or 9-carbazolyl), benzocarbazolyl, azacarbazolyl, diazacarbazolyl, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, azadibenzothiophenyl, diazadibenzothiophenyl, (9-phenyl)carbazolyl ((9-phenyl)carbazol-1-yl, (9-phenyl)carbazol-2-yl, (9-phenyl)carbazol-3-yl or (9-phenyl)carbazol-4-yl), (9-biphenylyl)carbazolyl, (9-phenyl)phenylcarbazolyl, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl, and phenyldibenzothiophenyl, etc.

[0343] In this specification, unless otherwise specified, the carbazolyl group is specifically any one of the following groups.

[0344] [Chemical formula 6]

[0345]

[0346] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically any one of the following groups.

[0347] [Chemical formula 7]

[0348]

[0349] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents the bonding position.

[0350] In this specification, unless otherwise specified, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any one of the following groups.

[0351] [Chemical Formula 8]

[0352]

[0353] In the above general formulas (TEMP-34) to (TEMP-41), * represents the bonding position.

[0354] Unless otherwise specified in this specification, the substituted or unsubstituted alkyl groups are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.

[0355] · "Substituted or unsubstituted arylene"

[0356] Unless otherwise specified in this specification, the "substituted or unsubstituted arylene" is a divalent group derived by removing one hydrogen atom from the aromatic ring of the above "substituted or unsubstituted aryl". As specific examples (specific example group G12) of the "substituted or unsubstituted arylene", divalent groups derived by removing one hydrogen atom from the aromatic ring of the "substituted or unsubstituted aryl" described in specific example group G1 can be cited, etc.

[0357] · "Substituted or unsubstituted divalent heterocyclic group"

[0358] Unless otherwise specified in this specification, the "substituted or unsubstituted divalent heterocyclic group" is a divalent group derived by removing one hydrogen atom from the heterocyclic ring of the above "substituted or unsubstituted heterocyclic group". As specific examples (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group", divalent groups derived by removing one hydrogen atom from the heterocyclic ring of the "substituted or unsubstituted heterocyclic group" described in specific example group G2 can be cited, etc.

[0359] · "Substituted or unsubstituted alkylene"

[0360] Unless otherwise specified in this specification, the "substituted or unsubstituted alkylene" is a divalent group derived by removing one hydrogen atom from the alkyl chain of the above "substituted or unsubstituted alkyl". As specific examples (specific example group G14) of the "substituted or unsubstituted alkylene", divalent groups derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl" described in specific example group G3 can be cited, etc.

[0361] Unless otherwise specified in this specification, the substituted or unsubstituted arylene is preferably any group in the following general formulas (TEMP-42) to (TEMP-68).

[0362] [Chemical Formula 9]

[0363]

[0364] [Chemical Formula 10]

[0365]

[0366] In the above general formulas (TEMP-42) to (TEMP-52), Q 1 ~Q 10 are each independently a hydrogen atom or a substituent.

[0367] In the above general formulas (TEMP-42) to (TEMP-52), * represents the bonding position.

[0368] [Chemical Formula 11]

[0369]

[0370] In the above general formulas (TEMP-53) to (TEMP-62), Q 1 ~Q 10 are each independently a hydrogen atom or a substituent.

[0371] The group Q 9 and Q 10 can be bonded to each other via a single bond to form a ring.

[0372] In the above general formulas (TEMP-53) to (TEMP-62), * represents the bonding position.

[0373] [Chemical Formula 12]

[0374]

[0375] In the above general formulas (TEMP-63) to (TEMP-68), Q 1 ~Q 8 are each independently a hydrogen atom or a substituent.

[0376] In the above general formulas (TEMP-63) to (TEMP-68), * represents the bonding position.

[0377] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any one of the following general formulas (TEMP-69) to (TEMP-102).

[0378] [Chemical Formula 13]

[0379]

[0380] [Chemical Formula 14]

[0381]

[0382] [Chemical Formula 15]

[0383]

[0384] In the above general formulas (TEMP-69) to (TEMP-82), Q 1 to Q 9 are each independently a hydrogen atom or a substituent.

[0385] [Chemical Formula 16]

[0386]

[0387] [Chemical Formula 17]

[0388]

[0389] [Chemical Formula 18]

[0390]

[0391] [Chemical Formula 19]

[0392]

[0393] In the above general formulas (TEMP-83) to (TEMP-102), Q 1 to Q 8 are each independently a hydrogen atom or a substituent.

[0394] The above is the description of "substituents described in this specification".

[0395] · "The case of forming a ring by bonding"

[0396] In this specification, the case described as "one or more groups selected from groups consisting of two or more adjacent... bond to each other to form a substituted or unsubstituted monocyclic ring, or bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other" means the case of "one or more groups selected from groups consisting of two or more adjacent... bond to each other to form a substituted or unsubstituted monocyclic ring", the case of "one or more groups selected from groups consisting of two or more adjacent... bond to each other to form a substituted or unsubstituted fused ring", and the case of "one or more groups selected from groups consisting of two or more adjacent... do not bond to each other".

[0397] Hereinafter, the cases of "forming a substituted or unsubstituted monocyclic ring by bonding one or more of the groups composed of two or more adjacent ones" and "forming a substituted or unsubstituted fused ring by bonding one or more of the groups composed of two or more adjacent ones" in this specification (hereinafter sometimes collectively referred to as "the case of forming a ring by bonding".) will be described. Taking the case of an anthracene compound represented by the following general formula (TEMP-103) with an anthracene ring as the mother skeleton as an example for description.

[0398] [Chemical formula 20]

[0399]

[0400] For example, in the case of "forming a ring by bonding one or more of the groups composed of two or more adjacent ones" among R 921 ~R 930 , the group composed of two adjacent ones that form one group refers to the group of R 921 and R 922 , the group of R 922 and R 923 , the group of R 923 and R 924 , the group of R 924 and R 930 , the group of R 930 and R 925 , the group of R 925 and R 926 , the group of R 926 and R 927 , the group of R 927 and R 928 , the group of R 928 and R 929 , the group of R 929 and R 921 , the group of R 921 and R 922 , the group of R A and R 925 , and the group of R 926 and R B .

[0401] The above "one or more groups" means that two or more of the groups composed of the above two or more adjacent ones can form rings simultaneously. For example, when R 921 and R 922 bond to each other to form ring Q A and at the same time R 925 and R 926 bond to each other to form ring Q B , the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0402] [Chemical formula 21]

[0403]

[0404] The case where a "group consisting of two or more adjacent members" forms a ring includes not only the case where a group consisting of "two" adjacent members bonds as in the aforementioned example, but also the case where a group consisting of "three or more" adjacent members bonds. For example, it means that R 921 bonds with R 922 to form ring Q A , and R 922 bonds with R 923 to form ring Q C . The case where a group consisting of three mutually adjacent ones (R 921 , R 922 , and R 923 ) bonds with each other to form a ring and is fused to the anthracene parent skeleton. In this case, 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 share R 922 .

[0405] [Chemical formula 22]

[0406]

[0407] In the "monocyclic" or "fused ring" formed, as the structure of the formed ring itself, it can be a saturated ring or an unsaturated ring. Even in the case where "one group among the groups consisting of two adjacent members" forms a "monocyclic" or "fused ring", the "monocyclic" or "fused ring" can also form a saturated ring or an unsaturated ring. For example, in the above general formula (TEMP-104), the formed ring Q A and ring Q B are each a "monocyclic" or "fused ring". Additionally, in the above general formula (TEMP-105), the formed ring Q A and ring Q C are "fused rings". The ring Q A of the above general formula (TEMP-105) and ring Q C form a fused ring by fusing through ring Q A and ring Q C . If the ring Q A in the above general formula (TEMP-104) is a benzene ring, then ring Q A is a monocyclic ring. If the ring Q A in the above general formula (TEMP-104) is a naphthalene ring, then ring Q A is a fused ring.

[0408] "Unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. "Saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.

[0409] As a specific example of the aromatic hydrocarbon ring, a structure in which the group exemplified as a specific example in the specific example group G1 is capped with a hydrogen atom can be cited.

[0410] As a specific example of the aromatic heterocyclic ring, a structure in which the aromatic heterocyclic group exemplified as a specific example in the specific example group G2 is capped with a hydrogen atom can be cited.

[0411] As a specific example of the aliphatic hydrocarbon ring, a structure in which the group exemplified as a specific example in the specific example group G6 is capped with a hydrogen atom can be cited.

[0412] "Forming a ring" means forming a ring only by a plurality of atoms of the parent skeleton or forming a ring by a plurality of atoms of the parent skeleton and one or more optional elements. For example, R shown in the above general formula (TEMP-104) 921 and R 922 bond to each other to form a ring Q A means that a ring is formed by the carbon atoms of the anthracene skeleton to which R 921 is bonded, the carbon atoms of the anthracene skeleton to which R 922 is bonded, and one or more optional elements. As a specific example, in the case where a ring Q 921 is formed by R 922 and R A , in the case where a single-ring unsaturated ring is formed by the carbon atoms of the anthracene skeleton to which R 921 is bonded, the carbon atoms of the anthracene skeleton to which R 922 is bonded, and 4 carbon atoms, the ring formed by R 921 and R 922 is a benzene ring.

[0413] Here, the "optional element" is preferably at least one element selected from the group consisting of a carbon element, a nitrogen element, an oxygen element, and a sulfur element unless otherwise specified in this specification. In the case of an optional element such as a carbon element or a nitrogen element), the bond that does not form a ring can be capped with a hydrogen atom or the like, or can be substituted with an "optional substituent" described later. When an optional element other than a carbon element is included, the formed ring is a heterocyclic ring.

[0414] Unless otherwise specified in this specification, the "one or more optional elements" constituting a single ring or a fused ring are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and still more preferably 3 or more and 5 or less.

[0415] Unless otherwise specified in this specification, among the "single ring" and the "fused ring", the "single ring" is preferred.

[0416] Unless otherwise specified in this specification, among the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred.

[0417] In this specification, unless otherwise specified, the "monocyclic ring" is preferably a benzene ring.

[0418] In this specification, unless otherwise specified, the "unsaturated ring" is preferably a benzene ring.

[0419] In the case of "one or more groups among groups composed of two or more adjacent ones" "bonded to each other to form a substituted or unsubstituted monocyclic ring" or "bonded to each other to form a substituted or unsubstituted fused ring", in this specification, unless otherwise specified, it is preferably one or more groups among groups composed of two or more adjacent ones bonded to each other to form a substituted or unsubstituted "unsaturated ring" formed by a plurality of atoms of the mother skeleton and at least one element selected from the group consisting of carbon element, nitrogen element, oxygen element, and sulfur element and having 1 or more and 15 or less.

[0420] When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "fused ring" has a substituent are the substituents described in the item of "substituents described in this specification" above.

[0421] When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "fused ring" has a substituent are the substituents described in the item of "substituents described in this specification" above.

[0422] The above is the description of the case of "one or more groups among groups composed of two or more adjacent ones bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case of "one or more groups among groups composed of two or more adjacent ones bonded to each other to form a substituted or unsubstituted fused ring" (the case of "bonded to form a ring").

[0423] · Substituents when expressed as "substituted or unsubstituted"

[0424] In one embodiment of this specification, the substituents when the above is expressed as "substituted or unsubstituted" (in this specification, sometimes referred to as "optional substituents") are, for example, selected from

[0425] unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0426] unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0427] unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0428] unsubstituted cycloalkyl groups having 3 to 50 ring carbon atoms,

[0429] -Si(R 901)(R 902 )(R 903 )、

[0430] -O-(R 904 )、

[0431] -S-(R 905 )、

[0432] -N(R 906 )(R 907 )、

[0433] a halogen atom, a cyano group, a nitro group,

[0434] an unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0435] an unsubstituted heterocyclic group having 5 to 50 ring atoms

[0436] and groups in the group consisting of,

[0437] Here, R 901 to R 907 are each independently

[0438] a hydrogen atom,

[0439] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0440] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0441] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0442] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0443] When there are two or more R 901 s, the two or more R 901 s may be the same or different from each other,

[0444] When there are two or more R 902 s, the two or more R 902 s may be the same or different from each other,

[0445] When there are two or more R 903 s, the two or more R 903 s may be the same or different from each other,

[0446] When there are two or more R 904 s, the two or more R 904 s may be the same or different from each other,

[0447] When there are two or more R 905 s, the two or more R905 Each is the same as or different from each other,

[0448] In the case of R 906 When there are two or more Rs, the two or more Rs 906 Each is the same as or different from each other,

[0449] In the case of R 907 When there are two or more Rs, the two or more Rs 907 Each is the same as or different from each other.

[0450] In one embodiment, when the above expression is "substituted or unsubstituted", the substituent is selected from the group consisting of

[0451] an alkyl group having 1 to 50 carbon atoms,

[0452] an aryl group having 6 to 50 ring carbon atoms, and

[0453] a heterocyclic group having 5 to 50 ring atoms

[0454] groups in the group.

[0455] In one embodiment, when the above expression is "substituted or unsubstituted", the substituent is selected from the group consisting of

[0456] an alkyl group having 1 to 18 carbon atoms,

[0457] an aryl group having 6 to 18 ring carbon atoms, and

[0458] a heterocyclic group having 5 to 18 ring atoms

[0459] groups in the group.

[0460] Specific examples of each group of the above optional substituents are the specific examples of the substituents described in the item of "substituents described in this specification" above.

[0461] In this specification, unless otherwise noted, "saturated rings" or "unsaturated rings" can be formed between adjacent optional substituents, preferably 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, and more preferably a benzene ring.

[0462] In this specification, unless otherwise noted, the optional substituent may further have a substituent. The substituent further possessed by the optional substituent is the same as the above optional substituent.

[0463] In this specification, the numerical range represented by "AA to BB" means the range including the numerical value AA described before "AA to BB" as the lower limit value and the numerical value BB described after "AA to BB" as the upper limit value.

[0464] Hereinafter, the compounds of the present invention will be described.

[0465] The compounds of the present invention are represented by the above formula (1). Hereinafter, the symbols in formula (1) and each of the following formulas included in formula (1) will be described. Unless otherwise stated, the same symbols have the same meanings.

[0466] The compounds of the present invention represented by formula (1) and the following formulas included in formula (1) are sometimes referred to as "invention compounds".

[0467] [Chemical formula 23]

[0468]

[0469] In formula (1),

[0470] N* is a central nitrogen atom.

[0471] Ar 1 and Ar 2 Each independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, preferably 6 to 25 ring carbon atoms, more preferably 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, preferably 5 to 18 ring atoms, more preferably 5 to 13 ring atoms.

[0472] The above-mentioned Ar 1 and Ar 2 Examples of the unsubstituted aryl group having 6 to 30 ring carbon atoms represented include phenyl, biphenyl, terphenyl, benzallenyl, naphthyl, anthracenyl, benzoanthracenyl, phenanthryl, benzophenanthryl, phenalenyl, chrysenyl, pentaphenyl, pyrenyl, yl, benzo yl, fluorenyl, fluoranthenyl, perylenyl, or triphenylene. Preferably, it is phenyl, biphenyl, terphenyl, or naphthyl. More preferably, it is phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, 2-o-terphenyl, 3-o-terphenyl or 4-o-terphenyl, 2-m-terphenyl, 3-m-terphenyl or 4-m-terphenyl, 2-p-terphenyl, 3-p-terphenyl or 4-p-terphenyl, or 1-naphthyl or 2-naphthyl. Further preferably, it is phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, or 1-naphthyl or 2-naphthyl. Particularly preferably, it is phenyl.

[0473] The above-mentioned Ar 1 and Ar 2The heterocyclic group having 5 to 30 unsubstituted ring-forming atoms, such as pyrrolyl, furyl, thienyl, pyridyl, imidazopyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, indolyl, isoindolyl, indazolyl, quinazolinyl, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, indazolyl, benzisoxazolyl, benzisothiazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, xanthenyl, benzofuryl, isobenzofuryl, naphthobenzofuryl, dibenzofuryl, benzothienyl (benzothienyl, the same below), isobenzothienyl (isobenzothienyl, the same below), naphthobenzothienyl (naphthobenzothienyl, the same below), dibenzothienyl (dibenzothienyl, the same below), or carbazolyl, preferably benzofuryl, isobenzofuryl, naphthobenzofuryl, dibenzofuryl, benzothienyl, isobenzothienyl, naphthobenzothienyl, dibenzothienyl, or carbazolyl (9-carbazolyl, or 1-carbazolyl, 2-carbazolyl, 3-carbazolyl or 4-carbazolyl).

[0474] Ar 1 and Ar 2 Each independently is preferably represented by the following formula (2A), (2B), (2C), (2D), (2E), (2F), or (2G).

[0475] [Chemical formula 24]

[0476]

[0477] In formula (2A),

[0478] *21 is the bonding position with L 1 or L 2 The bonding position of.

[0479] One selected from R 101 ~R 105 is a single bond bonded to *22, and one selected from R 106 ~R 110 is a single bond bonded to *23.

[0480] R that is not the above single bond 101 ~R 105 and R 106 ~R 110 Each independently is a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms.

[0481] R selected from those other than the above-mentioned single bond 101 ~R 105 Two adjacent ones among them do not bond to each other and do not form a ring.

[0482] R selected from those other than the above-mentioned single bond 106 ~R 110 Two adjacent ones among them do not bond to each other and do not form a ring.

[0483] R other than the above-mentioned single bond 101 ~R 105 and R 106 ~R 110 The unsubstituted alkyl group having 1 to 10 carbon atoms represented by, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, or decyl, preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl, more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, further preferably methyl or tert-butyl, and particularly preferably tert-butyl.

[0484] R1 other than the above-mentioned single bond 01 ~R 105 and R 106 ~R 110 The unsubstituted aryl group having 6 to 12 ring-constituting carbon atoms represented by, for example, phenyl, biphenyl, or naphthyl, preferably phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, or 1-naphthyl or 2-naphthyl, more preferably phenyl, or 1-naphthyl or 2-naphthyl, and particularly preferably phenyl.

[0485] R 111 ~R 115 Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-constituting carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.

[0486] Selected from R 111 ~R 115 Two adjacent ones among them do not bond to each other and do not form a ring.

[0487] The above-mentioned R 111 ~R 115 The details and preferred examples of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by the above-mentioned R 101 ~R 105 and R 106 ~R 110 are the same as those described above.

[0488] The above-mentioned R 111 ~R115 Details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented and its preferred examples are the same as those for R above 101 ~R 105 and R 106 ~R 110 are the same as the description.

[0489] R above 111 ~R 115 The unsubstituted heterocyclic group having 5 to 13 ring atoms represented is, for example, pyrrolyl, furyl, thienyl, pyridyl, imidazopyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, indolyl, isoindolyl, indolizinyl, quinazolinyl, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, indazolyl, benzoisoxazolyl, benzoisothiazolyl, benzofuryl, isobenzofuryl, dibenzofuryl, benzothienyl (benzothienyl, the same below), isobenzothienyl (isobenzothienyl, the same below), dibenzothienyl (dibenzothienyl, the same below), or carbazolyl, preferably pyrrolyl, furyl, thienyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, benzofuryl, isobenzofuryl, dibenzofuryl, benzothienyl, isobenzothienyl, dibenzothienyl, or carbazolyl, more preferably benzofuryl, isobenzofuryl, dibenzofuryl, benzothienyl, isobenzothienyl, dibenzothienyl, carbazolyl (9-carbazolyl, or 1-carbazolyl, 2-carbazolyl, 3-carbazolyl or 4-carbazolyl).

[0490] The substituted heterocyclic group having 5 to 13 ring atoms is, for example, 9-phenylcarbazolyl, 9-biphenylcarbazolyl, 9-phenylphenylcarbazolyl, 9-naphthylcarbazolyl, phenyldibenzofuryl, or phenyldibenzothienyl (phenyldibenzothienyl, the same below).

[0491] The above-mentioned substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms, when present, includes isomeric groups.

[0492] R in formula (2A) that is not a single bond 101 ~R 105 、R 106 ~R 110 and R 111 ~R 115 can all be hydrogen atoms.

[0493] m is 0, 1 or 2, and n is 0 or 1. The case where m is 2 and n is 0 is excluded.

[0494] When m = 0 and n = 0, *23 represents *21.

[0495] When m = 0 and n = 1, *22 represents *21.

[0496] When m = 1 and n = 0, *23 represents *22.

[0497] In one embodiment of the present invention, m is 0 and n is 0. In this case, *23 represents *21, and formula (2A) is represented by the following formula.

[0498] [Chemical formula 25]

[0499]

[0500] In another embodiment of the present invention, m is 0 and n is 1. In this case, *22 represents *21, and formula (2A) is represented by the following formula.

[0501] [Chemical formula 26]

[0502]

[0503] In another embodiment of the present invention, m is 1 and n is 0. In this case, *23 represents *22, and formula (2A) is represented by the following formula.

[0504] [Chemical formula 27]

[0505]

[0506] In another embodiment of the present invention, m is 1 and n is 1. In this case, formula (2A) is represented by the following formula.

[0507] [Chemical formula 28]

[0508]

[0509] In another embodiment of the present invention, m is 2 and n is 1. In this case, formula (2A) is represented by the following formula.

[0510] [Chemical formula 29]

[0511]

[0512] The group represented by formula (2A) is preferably represented by the following formula. In the following formula, R is omitted for simplicity.

[0513] R and the above R 101 ~R 105 and R 106 ~R 110 or R111 ~R 115 Same

[0514] [Chemical Formula 30]

[0515]

[0516] [Chemical Formula 31]

[0517]

[0518] In Formula (2B),

[0519] *24 is the bonding position with L 1 or L 2 The bonding position

[0520] One selected from R 121 ~R 128 is a single bond bonded to *25

[0521] R other than the above single bond 121 ~R 128 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms

[0522] Two adjacent ones selected from R other than the above single bond 121 ~R 128 do not bond to each other and do not form a ring

[0523] The above R 121 ~R 128 Details and preferred examples of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by are the same as those described for the above R 101 ~R 105 and R 106 ~R 110 The description is the same

[0524] The above R 121 ~R 128 Details and preferred examples of the unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by are the same as those described for the above R 101 ~R 105 and R 106 ~R 110 The description is the same

[0525] In one aspect of the present invention, preferably, one selected from R 121 , R 124 , R 125 and R 128 is a single bond bonded to *25

[0526] R which is not a single bond bonded to *25121 ~R 128 may all be hydrogen atoms.

[0527] [Chemical Formula 32]

[0528]

[0529] In formula (2C),

[0530] *26 is the bonding position with L 1 or L 2 of the bonding position.

[0531] Selected from R 131 ~R 140 One of them is a single bond bonded to *27.

[0532] R that is not the above single bond 131 ~R 140 Each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring-constituting carbon atoms.

[0533] Selected from R that is not the above single bond 131 ~R 140 Two adjacent ones do not bond to each other and do not form a ring.

[0534] The above R 131 ~R 140 Details and preferred examples of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by are the same as those described for the above R 101 ~R 105 and R 106 ~R 110 are the same.

[0535] The above R 131 ~R 140 Details and preferred examples of the unsubstituted aryl group having 6 to 12 ring-constituting carbon atoms represented by are the same as those described for the above R 101 ~R 105 and R 106 ~R 110 are the same.

[0536] In one aspect of the present invention, it is preferred that one selected from R 137 , R 138 and R 139 is a single bond bonded to *27, more preferably one selected from R 137 and R 139 is a single bond bonded to *27, and still more preferably R 139 is a single bond bonded to *27.

[0537] R that is not a single bond bonded to *27131 ~R 140 may all be hydrogen atoms.

[0538] [Chemical Formula 33]

[0539]

[0540] In formula (2D),

[0541] *28 is the bonding position with L 1 or L 2 bonding position.

[0542] X 11 is an oxygen atom, a sulfur atom, CR a R b , or NR c .

[0543] X 11 is preferably an oxygen atom, a sulfur atom, or CR a R b .

[0544] R a and R b each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 10 carbon atoms, and further preferably 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, preferably 3 to 18 ring carbon atoms, more preferably 3 to 10 ring carbon atoms, and further preferably 3 to 6 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, preferably 6 to 18 ring carbon atoms, and more preferably 6 to 12 ring carbon atoms, and may be bonded to each other to form a substituted or unsubstituted ring structure, or may not be bonded to each other and do not form a ring.

[0545] The above R a and R b The unsubstituted alkyl group having 1 to 30 carbon atoms represented, for example, is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, or dodecyl, preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, and further preferably methyl, ethyl, isopropyl, or tert-butyl, and particularly preferably methyl.

[0546] The above R a and R b The unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms represented, for example, is cyclopropyl, cyclopentyl, cyclohexyl, or cyclooctyl, preferably cyclohexyl or cyclooctyl.

[0547] The above R aand R b Details of the unsubstituted aryl group having 6 to 30 ring-forming carbon atoms represented by and its preferred examples are the same as those for the above-mentioned Ar 1 and Ar 2 are the same as the description.

[0548] The unsubstituted monocyclic ring formed by the above-mentioned R a and R b is, for example, a benzene ring, a cyclopentane ring, or a cyclohexane ring.

[0549] The unsubstituted fused ring formed by the above-mentioned R a and R b is, for example, a naphthalene ring or an anthracene ring.

[0550] In addition, when R a and R b are bonded to each other to form an unsubstituted monocyclic ring or an unsubstituted fused ring, R a and R b can form a spiro ring by cyclizing together with the fluorene skeleton to which these groups are bonded. The above spiro ring is a hydrocarbon ring or a heterocyclic ring and is selected from a monocyclic ring, a fused ring, a bicyclic bridged ring, and a tricyclic bridged ring. Examples of the substituted or unsubstituted spiro ring are shown below, but are not limited thereto. * indicates the bonding position to the benzene ring of the fluorene skeleton.

[0551] [Chemical formula 34]

[0552]

[0553] R c is a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, which may be substituted or unsubstituted, preferably 1 to 18, more preferably 1 to 10, and further preferably 1 to 6, an aryl group having 6 to 30 ring-forming carbon atoms, which may be substituted or unsubstituted, preferably 6 to 18, more preferably 6 to 12, or a heterocyclic group having 5 to 30 ring-forming atoms, which may be substituted or unsubstituted, preferably 5 to 18, more preferably 5 to 13.

[0554] Details of the unsubstituted alkyl group having 1 to 30 carbon atoms represented by the above R c and its preferred examples are the same as those for the above R a and R b are the same as the description.

[0555] Details of the unsubstituted aryl group having 6 to 30 ring-forming carbon atoms represented by the above R c and its preferred examples are the same as those for the above Ar 1 and Ar 2 are the same as the description.

[0556] Details of the unsubstituted heterocyclic group having 5 to 30 ring-forming atoms represented by the above R c and its preferred examples are the same as those for the above Ar 1 and Ar2 is the same as the description.

[0557] n is 0 or 1.

[0558] When n is 0, one selected from R a , R b , R c and R 141 ~R 148 is a single bond bonded to *29, or an aryl group with 6 to 30 ring-constituting carbon atoms, which may be substituted or unsubstituted, represented by R a or R b ; a ring structure which may be substituted or unsubstituted and formed by bonding R a or R b to each other; or an aryl group with 6 to 30 ring-constituting carbon atoms, which may be substituted or unsubstituted, represented by R c is bonded to *29 via a single bond.

[0559] When n is 1, one of R 141 and R 142 , R 142 and R 143 or R 143 and R 144 is a single bond bonded to *a, and the other is a single bond bonded to *b. One selected from R 141 ~R 144 , R 145 ~R 148 , Ra, Rb, Rc and R 200 ~R 203 is a single bond bonded to *29, or an aryl group with 6 to 30 ring-constituting carbon atoms, which may be substituted or unsubstituted, represented by Ra or Rb; a ring structure which may be substituted or unsubstituted and formed by bonding Ra or Rb to each other; or an aryl group with 6 to 30 ring-constituting carbon atoms, which may be substituted or unsubstituted, represented by R c is bonded to *29 via a single bond.

[0560] R 141 ~R 148 which is not the above single bond and R 200 ~R 203 each independently represents a hydrogen atom, an alkyl group with 1 to 10 carbon atoms which may be substituted or unsubstituted, an aryl group with 6 to 12 ring-constituting carbon atoms which may be substituted or unsubstituted, or a heterocyclic group with 5 to 13 ring-constituting atoms which may be substituted or unsubstituted.

[0561] Two adjacent ones selected from R 141 ~R 148 which is not the above single bond and R 200 ~R 203 do not bond to each other to form a ring.

[0562] The above R 141 ~R 148 and R 200 ~R 203 The details and preferred examples of the unsubstituted alkyl groups having 1 to 10 carbon atoms represented by are the same as those described for the above R 101 ~R 105 and R 106 ~R 110 are the same.

[0563] The above R 141 ~R 148 and R 200 ~R 203 The details and preferred examples of the unsubstituted aryl groups having 6 to 12 ring carbon atoms represented by are the same as those described for the above R 101 ~R 105 and R 106 ~R 110 are the same.

[0564] The above R 141 ~R 148 and R 200 ~R 203 The details and preferred examples of the unsubstituted heterocyclic groups having 5 to 13 ring atoms represented by are the same as those described for the above R 111 ~R 115 are the same.

[0565] R that is not the above single bond 141 ~R 148 and R that is not the above single bond 200 ~R 203 can both be hydrogen atoms.

[0566] [Chemical formula 35]

[0567]

[0568] In formula (2E),

[0569] *30 is the bonding position with L 1 or L 2 of.

[0570] One selected from R 151 ~R 155 is a single bond bonded to *31, and the other selected from R 151 ~R 155 is a single bond bonded to *32.

[0571] R that is not the above single bond 151 ~R 155Each independently represents a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group.

[0572] R is selected from the group consisting of 151 ~R 155 The two adjacent ones in the molecule are not bonded to each other and do not form a ring.

[0573] R 161 ~R 165 and R 171 ~R 175 Each is independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.

[0574] R is selected from R which is not a hydrogen atom 161 ~R 165 At least one pair of adjacent two of the above may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form no ring.

[0575] R is selected from R which is not a hydrogen atom 171 ~R 175 At least one pair of adjacent two of the above may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form no ring.

[0576] The above R 151 ~R 155 , R 161 ~R 165 and R 171 ~R 175 The details of the unsubstituted alkyl group having 1 to 10 carbon atoms and preferred examples thereof are the same as those for the above R 101 ~R 105 and R 106 ~R 110 The records are the same.

[0577] In one embodiment of the present invention, selected from R 161 ~R 165 In another embodiment of the present invention, two adjacent groups in are bonded to each other to form an unsubstituted benzene ring. 161 ~R 165 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring.

[0578] In one embodiment of the present invention, selected from R 171 ~R 175 In another embodiment of the present invention, two adjacent groups in are bonded to each other to form an unsubstituted benzene ring. 171 ~R 175 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring.

[0579] R is not a single bond as above151 ~R 155 may all be hydrogen atoms, R 161 ~R 165 may all be hydrogen atoms, R 171 ~R 175 may all be hydrogen atoms.

[0580] [Chemical formula 36]

[0581]

[0582] In formula (2F),

[0583] *32 is the bonding position with L 1 or L 2 of.

[0584] Selected from R 181 ~R 192 One of them is a single bond bonded to *33.

[0585] R other than the above single bond 181 ~R 192 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.

[0586] Selected from R other than the above single bond 181 ~R 192 Two adjacent ones of them do not bond to each other and do not form a ring.

[0587] The above R 181 ~R 192 The details and preferred examples of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by are the same as those described for the above R 101 ~R 105 and R 106 ~R 110 are the same.

[0588] The above R 181 ~R 192 The details and preferred examples of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by are the same as those described for the above R 101 ~R 105 and R 106 ~R 110 are the same.

[0589] In one aspect of the present invention, R 184 is a single bond bonded to *33, and in another aspect, R 183 is a single bond bonded to *33.

[0590] R other than the above single bond 181 ~R 192They can all be hydrogen atoms.

[0591] Ar 1 and Ar 2 Each is independently preferably represented by formula (2A) or (2D), and more preferably represented by formula (2A).

[0592] L 1 and L 2 Each is independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, preferably 6 to 18, more preferably 6 to 12, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, preferably 5 to 18, more preferably 5 to 13.

[0593] The above-mentioned L 1 and L 2 The unsubstituted arylene group having 6 to 30 ring carbon atoms represented refers to a divalent group obtained by removing one hydrogen atom from an unsubstituted aryl group having 6 to 30 ring carbon atoms. The details of the above-mentioned unsubstituted aryl group having 6 to 30 ring carbon atoms are the same as those described for the above-mentioned Ar 1 and Ar 2 The above-mentioned L 1 and L 2 The unsubstituted arylene group having 6 to 30 ring carbon atoms represented is preferably a phenylene group, a naphthylene group, or a biphenylene group, more preferably a phenylene group, and further preferably a 1,4-phenylene group.

[0594] The above-mentioned L 1 and L 2 The unsubstituted divalent heterocyclic group having 5 to 30 ring atoms represented refers to a divalent group obtained by removing one hydrogen atom from an unsubstituted heterocyclic group having 5 to 30 ring atoms. The details of the above-mentioned unsubstituted heterocyclic group having 5 to 30 ring atoms are the same as those described for the above-mentioned Ar l and Ar 2 The above-mentioned L 1 and L 2 The unsubstituted divalent heterocyclic group having 5 to 30 ring atoms represented is preferably a divalent group derived by removing one hydrogen atom on the heterocycle from a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

[0595] L 3 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, preferably 6 to 18, more preferably 6 to 12, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, preferably 5 to 18, more preferably 5 to 13.

[0596] The details and preferred examples of the unsubstituted arylene group having 6 to 30 ring carbon atoms represented by the above-mentioned L 3 are the same as those described for the above-mentioned L1 and L 2 above.

[0597] The above L 3 Details of the unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms represented thereby and preferred examples thereof are the same as those described for the above L 1 and L 2 are the same.

[0598] L 3 is preferably a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, more preferably a substituted or unsubstituted arylene group having 6 to 12 ring-forming carbon atoms, still more preferably a phenylene group, and particularly preferably a 1,4-phenylene group.

[0599] R 1 to R 10 are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms, a group represented by -Si(R 901 )(R 902 )(R 903 ), a group represented by -O-(R 904 ), or a group represented by -S-(R 905 ),

[0600] R 901 to R 905 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,

[0601] When there are two or more R 901 , the two or more R 901 are the same as or different from each other,

[0602] When there are two or more R 902 , the two or more R 902 are the same as or different from each other,

[0603] When there are two or more R 903 , the two or more R 903 are the same as or different from each other,

[0604] When there are two or more R 904When there are two or more, two or more Rs 904 are the same as or different from each other,

[0605] When there are two or more Rs 905 are the same as or different from each other. 905 Among them, two adjacent ones selected from R2 to R

[0606] can be bonded to each other to form a substituted or unsubstituted benzene ring, or may not be bonded to each other and thus do not form a ring. 10

[0607] The details of the unsubstituted alkyl group having 1 to 50 carbon atoms represented by the above Rs 1 to R 10 are the same as those described in the item of "Substituents described in this specification" above.

[0608] The details of the unsubstituted alkenyl group having 2 to 50 carbon atoms represented by the above Rs 1 to R 10 are the same as those described in the item of "Substituents described in this specification" above.

[0609] The details of the unsubstituted alkynyl group having 2 to 50 carbon atoms represented by the above Rs 1 to R 10 are the same as those described in the item of "Substituents described in this specification" above.

[0610] The details of the unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms represented by the above Rs 1 to R 10 are the same as those described in the item of "Substituents described in this specification" above.

[0611] The details of the unsubstituted aryl group having 6 to 50 ring carbon atoms represented by the above Rs 1 to R 10 are the same as those described in the item of "Substituents described in this specification" above.

[0612] The details of the aralkyl group having 7 to 50 carbon atoms represented by the above Rs 1 to R 10 are the same as those described in the item of "Substituents described in this specification" above.

[0613] The details of the unsubstituted heterocyclic group having 5 to 50 ring atoms represented by the above Rs 1 to R 10 are the same as those described in the item of "Substituents described in this specification" above.

[0614] The details of the above Rs 1 to R 10 ​Details of the unsubstituted haloalkyl group having 1 to 50 carbon atoms are the same as those described in the item of "Substituents described in this specification" above.

[0615] The above R 901 ~R 905 Details of the unsubstituted alkyl group having 1 to 50 carbon atoms are the same as those described in the item of "Substituents described in this specification" above.

[0616] The above R 901 ~R 905 Details of the unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms are the same as those described in the item of "Substituents described in this specification" above.

[0617] The above R 901 ~R 905 Details of the unsubstituted aryl group having 6 to 50 ring carbon atoms are the same as those described in the item of "Substituents described in this specification" above.

[0618] The above R 901 ~R 905 Details of the unsubstituted aryl group having 6 to 50 ring carbon atoms are the same as those described in the item of "Substituents described in this specification" above.

[0619] The above R 901 ~R 905 Details of the unsubstituted heterocyclic group having 5 to 50 ring atoms are the same as those described in the item of "Substituents described in this specification" above.

[0620] The above R 1 ~R 10 They may all be hydrogen atoms.

[0621] X 1 is an oxygen atom or a sulfur atom.

[0622] X 1 is preferably an oxygen atom.

[0623] As described above, the "hydrogen atom" used in this specification includes protium atom, deuterium atom and tritium atom. Therefore, the inventive compound may contain deuterium atoms of natural origin.

[0624] In addition, deuterium atoms can be deliberately introduced into the inventive compound by using a deuterated compound for a part or all of the starting compounds. Therefore, in one aspect of the present invention, the inventive compound contains at least 1 deuterium atom. That is, the inventive compound may be a compound represented by formula (1), and at least one of the hydrogen atoms contained in the compound is a deuterium atom.

[0625] At least one hydrogen atom selected from the following hydrogen atoms may be a deuterium atom. It should be noted that hereinafter, "substituted or unsubstituted", the number of carbon atoms and the number of atoms are omitted.

[0626] In the case where any one of Ar in formula (1) 1 and Ar 2 is an aryl group or a heterocyclic group, the hydrogen atoms of the aryl group or the heterocyclic group;

[0627] In the case where any one of L in formula (1) 1 ~L 3 is an arylene group or a divalent heterocyclic group, the hydrogen atoms of the arylene group or the divalent heterocyclic group;

[0628] The hydrogen atoms represented by any one of R in formula (1) 1 ~R 10 ;

[0629] In the case where any one of R in formula (1) 1 ~R 10 is an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, an aryl group, an aralkyl group, a heterocyclic group, a haloalkyl group, a haloalkoxy group, a group represented by -Si(R 901 )(R 902 )(R 903 ), a group represented by -O-(R 904 ), or a group represented by -S-(R 905 ), the hydrogen atoms of the alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the aryl group, the aralkyl group, the heterocyclic group, the haloalkyl group, the haloalkoxy group, the group represented by -Si(R 901 )(R 902 )(R 903 ), the group represented by -O-(R 904 ), or the group represented by -S-(R 905 );

[0630] The deuteration rate of the inventive compound depends on the deuteration rate of the starting compound used. Even when using a starting compound with a specified deuteration rate, it may contain a certain proportion of protium isotopes from natural sources. Therefore, for the form of the deuteration rate of the inventive compound, a ratio that takes into account trace amounts of isotopes from natural sources is included, as opposed to a ratio calculated by simply counting the number of deuterium atoms represented in the chemical formula.

[0631] The deuteration rate of the inventive compound is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, still further preferably 10% or more, and still further preferably 50% or more.

[0632] The inventive compound may be a mixture comprising a deuterated compound and a non-deuterated compound, or a mixture of two or more compounds having 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, still further preferably 10% or more, still further preferably 50% or more, and less than 100%.

[0633] In addition, the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the inventive compound is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, still further preferably 10% or more, and 100% or less.

[0634] When the "substituted or unsubstituted XX group" included in the definitions of the above formulas is a substituted XX group, the details of the substituent are the same as those described in "the substituent when expressed as'substituted or unsubstituted'", and are preferably an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring carbon atoms, or a heterocyclic group (heteroaryl) having 5 to 13 ring atoms, more preferably an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 12 ring carbon atoms. The details of each group (alkyl group, aryl group, heteroaryl) are the same as above.

[0635] The inventive compound can be easily manufactured by those skilled in the art with reference to the following synthesis examples and well-known synthesis methods.

[0636] Specific examples of the inventive compound are shown below, but are not limited to the following exemplified compounds.

[0637] In the following specific examples, D represents a deuterium atom.

[0638] [Chemical formula 37]

[0639]

[0640] [Chemical formula 38]

[0641]

[0642] [Chemical formula 39]

[0643]

[0644] [Chemical formula 40]

[0645]

[0646] [Chemical formula 41]

[0647]

[0648] [Chemical formula 42]

[0649]

[0650] [Chemical Formula 43]

[0651]

[0652] [Chemical Formula 44]

[0653]

[0654] [Chemical Formula 45]

[0655]

[0656] [Chemical Formula 46]

[0657]

[0658] [Chemical Formula 47]

[0659]

[0660] [Chemical Formula 48]

[0661]

[0662] [Chemical Formula 49]

[0663]

[0664] [Chemical Formula 50]

[0665]

[0666] [Chemical Formula 51]

[0667]

[0668] [Chemical Formula 52]

[0669]

[0670] [Chemical Formula 53]

[0671]

[0672] [Chemical Formula 54]

[0673]

[0674] [Chemical Formula 55]

[0675]

[0676] [Chemical Formula 56]

[0677]

[0678] [Chemical Formula 57]

[0679]

[0680] [Chemical Formula 58]

[0681]

[0682] [Chemical Formula 59]

[0683]

[0684] [Chemical Formula 60]

[0685]

[0686] [Chemical Formula 61]

[0687]

[0688] [Chemical Formula 62]

[0689]

[0690] [Chemical Formula 63]

[0691]

[0692] [Chemical Formula 64]

[0693]

[0694] [Chemical Formula 65]

[0695]

[0696] [Chemical Formula 66]

[0697]

[0698] [Chemical Formula 67]

[0699]

[0700] [Chemical Formula 68]

[0701]

[0702] [Chemical Formula 69]

[0703]

[0704] [Chemical Formula 70]

[0705]

[0706] [Chemical Formula 71]

[0707]

[0708] [Chemical Formula 72]

[0709]

[0710] [Chemical Formula 73]

[0711]

[0712] [Chemical Formula 74]

[0713]

[0714] [Chemical Formula 75]

[0715]

[0716] [Chemical Formula 76]

[0717]

[0718] [Chemical Formula 77]

[0719]

[0720] [Chemical Formula 78]

[0721]

[0722] [Chemical Formula 79]

[0723]

[0724] [Chemical Formula 80]

[0725]

[0726] [Chemical Formula 81]

[0727]

[0728] [Chemical Formula 82]

[0729]

[0730] [Chemical Formula 83]

[0731]

[0732] [Chemical Formula 84]

[0733]

[0734] [Chemical Formula 85]

[0735]

[0736] [Chemical Formula 86]

[0737]

[0738] [Chemical Formula 87]

[0739]

[0740] [Chemical Formula 88]

[0741]

[0742] [Chemical Formula 89]

[0743]

[0744] [Chemical Formula 90]

[0745]

[0746] [Chemical Formula 91]

[0747]

[0748] [Chemical Formula 92]

[0749]

[0750] [Chemical Formula 93]

[0751]

[0752] [Chemical Formula 94]

[0753]

[0754] [Chemical Formula 95]

[0755]

[0756] [Chemical Formula 96]

[0757]

[0758] [Chemical Formula 97]

[0759]

[0760] [Chemical Formula 98]

[0761]

[0762] [Chemical Formula 99]

[0763]

[0764] [Chemical Formula 100]

[0765]

[0766] [Chemical Formula 101]

[0767]

[0768] [Chemical Formula 102]

[0769]

[0770] [Chemical Formula 103]

[0771]

[0772] [Chemical Formula 104]

[0773]

[0774] [Chemical Formula 105]

[0775]

[0776] [Chemical Formula 106]

[0777]

[0778] [Chemical Formula 107]

[0779]

[0780] [Chemical Formula 108]

[0781]

[0782] [Chemical Formula 109]

[0783]

[0784] [Chemical Formula 110]

[0785]

[0786] [Chemical Formula 111]

[0787]

[0788] [Chemical formula 112]

[0789]

[0790] [Chemical formula 113]

[0791]

[0792] [Chemical formula 114]

[0793]

[0794] [Chemical formula 115]

[0795]

[0796] [Chemical formula 116]

[0797]

[0798] [Chemical formula 117]

[0799]

[0800] [Chemical formula 118]

[0801]

[0802] Materials for organic EL elements

[0803] The materials for organic EL elements of the present invention contain the inventive compounds. The content of the inventive compounds in the materials for organic EL elements is 1% by mass or more (including 100%), preferably 10% by mass or more (including 100%), more preferably 50% by mass or more (including 100%), still more preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%). The materials for organic EL elements of the present invention are useful for the manufacture of organic EL elements.

[0804] Organic EL element

[0805] The organic EL element of the present invention includes 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 compounds.

[0806] Examples of the organic layer containing the inventive compound include a hole transport region (hole injection layer, hole transport layer, electron blocking layer, exciton blocking layer, etc.) provided between the anode and the light-emitting layer, a light-emitting layer, a spacer layer, an electron transport region (electron injection layer, electron transport layer, hole blocking layer, etc.) provided between the cathode and the light-emitting layer, etc., and are not limited thereto. The inventive compound is preferably used as a material for the hole transport region or the light-emitting layer of a fluorescent or phosphorescent EL element, more preferably as a material for the hole transport region, and further preferably as a material for the hole injection layer, hole transport layer, electron blocking layer, or exciton blocking layer, and particularly preferably as a material for the hole injection layer or hole transport layer.

[0807] The organic EL element of the present invention can be a monochromatic light-emitting element of fluorescent or phosphorescent light emission type, or can be a white light-emitting element of fluorescent / phosphorescent hybrid type, and can be a simple type having a single light-emitting unit or a tandem type having a plurality of light-emitting units. Among them, a fluorescent light-emitting type element is preferred. Here, the "light-emitting unit" means the smallest unit that includes an organic layer, at least one of which is a light-emitting layer, and in which the injected holes and electrons recombine to emit light.

[0808] For example, as a typical element configuration of a simple type organic EL element, the following element configurations can be cited.

[0809] (1) Anode / Light-emitting unit / Cathode

[0810] In addition, the above light-emitting unit can also be a multi-layer type having a plurality of phosphorescent light-emitting layers or fluorescent light-emitting layers. In this case, a spacer layer can also be provided between the respective light-emitting layers for the purpose of preventing excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer. The following shows typical layer configurations of a simple type light-emitting unit. The layers in parentheses are optional.

[0811] (a) (Hole injection layer / ) Hole transport layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0812] (b) (Hole injection layer / ) Hole transport layer / First fluorescent light-emitting layer / Second fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0813] (c) (Hole injection layer / ) Hole transport layer / Phosphorescent light-emitting layer / Spacer layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0814] (d) (Hole injection layer / ) Hole transport layer / First phosphorescent light-emitting layer / Second phosphorescent light-emitting layer / Spacer layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0815] (e) (Hole injection layer / ) Hole transport layer / Phosphorescent light-emitting layer / Spacer layer / First fluorescent light-emitting layer / Second fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0816] (f) (Hole injection layer / ) Hole transport layer / Electron blocking layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0817] (g) (Hole injection layer / ) Hole transport layer / Exciton blocking layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0818] (h) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0819] (i) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Fluorescent light-emitting layer / First electron transport layer / Second electron transport layer ( / Electron injection layer)

[0820] (j) (Hole injection layer / ) Hole transport layer / Fluorescent light-emitting layer / Hole blocking layer / Electron transport layer ( / Electron injection layer)

[0821] (k) (Hole injection layer / ) Hole transport layer / Fluorescent light-emitting layer / Exciton blocking layer / Electron transport layer ( / Electron injection layer)

[0822] (1) (Hole injection layer / ) First hole transport layer / Second hole transport layer / First fluorescent light-emitting layer / Second fluorescent light-emitting layer / First electron transport layer / Second electron transport layer ( / Electron injection layer)

[0823] (m) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Third hole transport layer / First fluorescent light-emitting layer / Second fluorescent light-emitting layer / First electron transport layer / Second electron transport layer ( / Electron injection layer)

[0824] (n) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Third hole transport layer / Fluorescent light-emitting layer / First electron transport layer / Second electron transport layer ( / Electron injection layer)

[0825] Each of the above phosphorescent or fluorescent light-emitting layers may be provided as a light-emitting layer that emits mutually different light emission colors. Specifically, in the above light-emitting unit (f), a layer configuration such as (hole injection layer / ) hole transport layer / first phosphorescent light-emitting layer (red light emission) / second phosphorescent light-emitting layer (green light emission) / spacer layer / fluorescent light-emitting layer (blue light emission) / electron transport layer can be cited, etc.

[0826] It should be noted that an electron blocking layer (sometimes referred to as an electron hindering layer) can be appropriately provided between each light-emitting layer and the hole transport layer or the spacer layer. Additionally, a hole blocking layer can be appropriately provided between each light-emitting layer and the electron transport layer. By providing the electron blocking layer and the hole blocking layer, electrons or holes can be confined within the light-emitting layer, thereby increasing the recombination probability of charges in the light-emitting layer and improving the light-emitting efficiency.

[0827] Furthermore, the hole transport layer adjacent to the light-emitting layer in a multi-layer structure including two or more hole transport layers, such as the second hole transport layer in the above-described two-layer structure and the third hole transport layer in the above-described three-layer structure, can function as an electron blocking layer. That is, in the case where the hole transport layer is a multi-layer structure including two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer in the above multi-layer structure can also be used as an electron blocking layer.

[0828] As a typical element configuration of a tandem organic EL element, the following element configurations can be cited.

[0829] (2) Anode / First light-emitting unit / Intermediate layer / Second light-emitting unit / Cathode

[0830] Here, as the above first light-emitting unit and second light-emitting unit, for example, they can be independently selected from the above-described light-emitting units.

[0831] The above intermediate layer is generally also referred to as an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, an intermediate insulating layer, and can be formed of a known material that supplies electrons to the first light-emitting unit and holes to the second light-emitting unit.

[0832] Figure 1 It is a schematic diagram showing an example of the configuration of the organic EL element of the present invention. The organic EL element 1 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. Additionally, 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. Thereby, electrons and holes can be confined within the light-emitting layer 5, further improving the generation efficiency of excitons in the light-emitting layer 5.

[0833] Figure 2Schematic diagram showing another configuration of the organic EL element of the present invention. The organic EL element 11 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.

[0834] Figure 3 Schematic diagram showing another configuration of the organic EL element 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. 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.

[0835] It should be noted that in the present invention, the host combined with a fluorescent dopant material (fluorescent light-emitting material) is called a fluorescent host, and the host combined with a phosphorescent dopant material is called a phosphorescent host. The fluorescent host and the phosphorescent host are not distinguished only by the molecular structure. That is, the phosphorescent host refers to a material that forms a phosphorescent light-emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material for forming a fluorescent light-emitting layer. The same applies to the fluorescent host.

[0836] Substrate

[0837] The substrate serves as a support for the organic EL element. As the substrate, for example, a plate of glass, quartz, plastic, etc. can be used. In addition, a flexible substrate can also be used. As the flexible substrate, for example, a plastic substrate formed of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, etc. can be cited. In addition, an inorganic vapor deposition film can also be used.

[0838] Anode

[0839] The anode formed on the substrate preferably uses metals, alloys, conductive compounds, and mixtures thereof, etc. with a large work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO: Indium Tin Oxide), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium oxide containing tungsten oxide and zinc oxide, graphene, etc. can be cited. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the above metals (such as titanium nitride), etc. can be cited.

[0840] These materials are usually formed into a film by sputtering. For example, indium zinc oxide can be formed by sputtering using a target formed by adding 1 to 10 wt% of zinc oxide to indium oxide, and indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5 to 5 wt% of tungsten oxide and 0.1 to 1 wt% of zinc oxide relative to indium oxide. In addition, it can also be produced by vacuum evaporation, coating, inkjet, spin coating, etc.

[0841] Hole transport region

[0842] As described above, the above organic layer may include a hole transport region located between the above anode and the above light-emitting layer. The hole transport region is composed of a hole injection layer, a hole transport layer, an electron blocking layer, etc. The hole transport region preferably contains the inventive compound. It is preferred to contain the inventive compound in at least one of these layers constituting the hole transport layer, and it is particularly more preferred to contain the inventive compound in the hole transport layer.

[0843] The hole injection layer formed adjacent to the anode is formed of a material that is easy to inject holes regardless of the work function of the anode. Therefore, materials commonly used as electrode materials (such as metals, alloys, conductive compounds and mixtures thereof, elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0844] Elements belonging to Group 1 or Group 2 of the periodic table, which are materials with a small work function, such as 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 (such as MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them, etc. can also be used. It should be noted that when forming the anode using alkali metals, alkaline earth metals, and alloys containing them, vacuum evaporation or sputtering can be used. In addition, when using silver paste, etc., coating, inkjet, etc. can be used.

[0845] Hole injection layer

[0846] The hole injection layer is a layer containing a material with high hole injection property (hole injection material), which is formed between the anode and the light-emitting layer, or between the hole transport layer and the anode when the hole transport layer exists.

[0847] As hole injection materials other than the inventive compounds, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. can be used.

[0848] As hole injection layer materials, aromatic amine compounds such as 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-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4’-bis(N-{4-[N’-(3-methylphenyl)-N’-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCAl), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), etc., which are low molecular organic compounds, can also be cited.

[0849] High molecular compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N’-[4-(4-diphenylamino)phenyl]phenyl-N’-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N’-bis(4-butylphenyl)-N,N’-bis(phenyl)benzidine] (abbreviation: Poly-TPD), etc. can be cited. In addition, acid-added high molecular compounds such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly(styrenesulfonic acid) (PAni / PSS), etc. can also be used.

[0850] In addition, acceptor materials such as hexaazatriphenylene (HAT) compounds represented by the following formula (K) are also preferably used.

[0851] [Chemical formula 119]

[0852]

[0853] (In the above formula, R 221 ~R 226 each independently represents a cyano group, -CONH 2 , a carboxyl group, or -COOR 227 (R 227 represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms). Further, two adjacent ones selected from R 221 and R 222 , R 223 and R 224 as well as R 225 and R 226 can be bonded to each other to form a group represented by -CO-O-CO-).

[0854] As R 227 , examples include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, a cyclopentyl group, a cyclohexyl group, etc.

[0855] Hole transport layer

[0856] The hole transport layer is a layer containing a material with high hole transport property (hole transport material), formed between the anode and the light-emitting layer, or formed between the hole injection layer and the light-emitting layer when the hole injection layer exists. The inventive compound can be used alone or in combination with the following compounds for the hole transport layer.

[0857] 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 containing a first hole transport layer (anode side) and a second hole transport layer (cathode side). That is, the above hole transport region can include the first hole transport layer on the anode side and the second hole transport layer on the cathode side. Further, the hole transport layer can be a three-layer structure sequentially including a first hole transport layer, a second hole transport layer, and a third hole transport layer from the anode side. That is, the third hole transport layer can be disposed between the second hole transport layer and the light-emitting layer.

[0858] In one aspect of the present invention, the above single-layer hole transport layer is preferably adjacent to the light-emitting layer. Further, the hole transport layer closest to the cathode in the above multi-layer structure, for example, the second hole transport layer in the above two-layer structure or the third hole transport layer in the above three-layer structure, is preferably adjacent to the light-emitting layer. In another aspect of the present invention, an electron blocking layer or the like described later can be interposed between the above single-layer hole transport layer and the light-emitting layer, or between the hole transport layer closest to the light-emitting layer in the above multi-layer structure and the light-emitting layer.

[0859] In the case where the hole transport layer has a two-layer structure, at least one of the first hole transport layer and the second hole transport layer contains the inventive compound. That is, the inventive compound is contained only in the first hole transport layer, only in the second hole transport layer, or in both the first hole transport layer and the second hole transport layer.

[0860] In one aspect of the present invention, the inventive compound is preferably contained in the second hole transport layer. That is, preferably, the inventive compound is contained only in the second hole transport layer, or the inventive compound is contained in both the first hole transport layer and the second hole transport layer.

[0861] In the case where the hole transport layer has a three-layer structure, at least one layer among the first to third hole transport layers contains the inventive compound. That is, the inventive compound is contained in only one layer selected from the first to third hole transport layers (only the first hole transport layer, only the second hole transport layer, or only the third hole transport layer), in only two layers selected from the first to third hole transport layers (only the first hole transport layer and the second hole transport layer, only the first hole transport layer and the third hole transport layer, or only the second hole transport layer and the third hole transport layer), or in all of the first to third hole transport layers.

[0862] In one aspect of the present invention, it is preferred that the inventive compound is contained in the third hole transport layer. That is, preferably, the inventive compound is contained only in the third hole transport layer, or the inventive compound is contained in the third hole transport layer and one or both of the first hole transport layer and the second hole transport layer.

[0863] In one aspect of the present invention, from the viewpoint of manufacturing cost, the inventive compound contained in each of the above hole transport layers is preferably protium. The protium refers to an inventive compound in which all hydrogen atoms in the inventive compound are protium atoms.

[0864] Therefore, the present invention includes: an organic EL element in which one or both of the first hole transport layer and the second hole transport layer (in the case of a two-layer structure) contain an inventive compound substantially formed only of protium, and an organic EL element in which at least one layer among the first to third hole transport layers contains an inventive compound substantially formed only of protium. The meaning of "an inventive compound substantially formed only of protium" means that the content ratio of protium is 90 mol% or more, preferably 95 mol% or more, more preferably 99 mol% or more (including 100% respectively) with respect to the total amount of the inventive compound.

[0865] As a hole transport layer material other than the inventive compound, for example, an aromatic amine compound, a carbazole derivative, an anthracene derivative, etc. can be used.

[0866] As aromatic amine compounds, for example, the following can be cited: 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-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), and 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The above compounds have a hole mobility of 10 -6 cm 2 / Vs or more.

[0867] As carbazole derivatives, for example, the following can be cited: 4,4'-bis(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA).

[0868] As anthracene derivatives, for example, the following can be cited: 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-bis(2-naphthyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth).

[0869] Polymeric compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.

[0870] Among them, compounds other than the above can be used as long as they have a higher hole transport property than the electron transport property.

[0871] In the organic EL element having the hole transport layer with the two-layer structure of the present invention, it is preferable that the first hole transport layer contains one or more compounds represented by the following formula (11) or formula (12).

[0872] In the organic EL element having the hole transport layer with the three-layer structure of the present invention, it is preferable that one or both of the first hole transport layer and the second hole transport layer contain one or more compounds represented by the following formula (11) or (12).

[0873] In an organic EL element having a hole transport layer with the n-layer structure (n is an integer of 4 or more) of the present invention, it is preferable that at least one layer of the first hole transport layer to the (n-1) hole transport layer contains one or more compounds represented by the following formula (11) or formula (12).

[0874] [Chemical formula 120]

[0875]

[0876] [In the above formula (11) and formula (12),

[0877] L A1 、L B1 、L C1 、L A2 、L B2 、L C2 and L D2 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[0878] k is 1, 2, 3 or 4,

[0879] When k is 1, L E2 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[0880] When k is 2, 3 or 4, 2, 3 or 4 L E2 are the same or different from each other,

[0881] When k is 2, 3 or 4, multiple L E2 are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,

[0882] L that does not form the above monocyclic ring and does not form the above condensed ring E2 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[0883] A 1 、B 1 、C 1 、A 2 、B 2 、C 2 and D 2 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or -Si(R’ 901 )(R’902 )(R' 903 ),

[0884] R' 901 , R' 902 and R' 903 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0885] In R' 901 When there are multiple R' 901 Same or different from each other,

[0886] In R' 902 When there are multiple R' 902 Same or different from each other,

[0887] In R' 903 When there are multiple R' 903 The same as or different from each other.]

[0888] In formula (11) and formula (12), preferably, A 1 , B 1 , C 1 , A 2 , B 2 , C 2 and D 2 Each is independently selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group and a substituted or unsubstituted carbazolyl group.

[0889] In addition, it is more preferred that A in formula (11) 1 , B 1 and C 1 At least one of them, and A2, B in formula (12) 2 , C 2 and D 2 At least one of them is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0890] A 1 , B 1 , C 1 , A 2 , B 2 , C 2 and D 2The selectable fluorenyl group may have a substituent at the 9-position, for example, it may be a 9,9-dimethylfluorenyl group or a 9,9-diphenylfluorenyl group. Additionally, the substituents at the 9-position may form a ring with each other, for example, a fluorene skeleton or a xanthene skeleton may be formed by the substituents at the 9-position with each other.

[0891] L A1 、L B1 、L C1 、L A2 、L B2 、L C2 and L D2 Preferably, each is independently a single bond, a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.

[0892] As specific examples of the compounds represented by formula (11) and formula (12), the following compounds can be cited, for example.

[0893] [Chemical formula 121]

[0894]

[0895] Dopant material for the light-emitting layer

[0896] The light-emitting layer is a layer containing a material with high luminescence (dopant material), and various materials can be used. For example, fluorescent luminescent materials and phosphorescent luminescent materials can be used as the dopant material. Fluorescent luminescent materials are compounds that emit light using singlet excited states, and phosphorescent luminescent materials are compounds that emit light using triplet excited states.

[0897] In one aspect of the organic EL element according to the present invention, the light-emitting layer is a single layer.

[0898] Additionally, in another aspect of the organic EL element according to the present invention, the light-emitting layer includes a first light-emitting layer and a second light-emitting layer.

[0899] As the blue fluorescent luminescent material that can be used for the light-emitting layer, pyrene derivatives, styrylamine derivatives, derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. can be used. Specifically, N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), etc. can be cited.

[0900] As a green fluorescent light-emitting material that can be used in the light-emitting layer, aromatic amine derivatives and the like can be used. Specifically, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), etc. can be cited.

[0901] As a red fluorescent light-emitting material that can be used in the light-emitting layer, tetracene derivatives, diamine derivatives and the like can be used. Specifically, N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), etc. can be cited.

[0902] In one aspect of the present invention, it is preferred that the light-emitting layer contains a fluorescent light-emitting material (fluorescent dopant material).

[0903] As a blue phosphorescent light-emitting material that can be used in the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes can be used. Specifically, bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III) picolinate (abbreviation: FIrpic), bis[2-(3',5'-bis(trifluoromethyl)phenyl)pyridine-N,C2']iridium(III) picolinate (abbreviation: Ir(CF3ppy)2(pic)), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III) acetylacetonate (abbreviation: FIracac), etc. can be cited.

[0904] As a green phosphorescent material that can be used in the light-emitting layer, iridium complexes or the like can be used. Examples include tris(2-phenylpyridine-N,C2’)iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridine-N,C2’)iridium(III) acetylacetonate (abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazole)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), bis(benzo[h]quinoline)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)), etc.

[0905] As a red phosphorescent material that can be used in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes can be used. Specifically, examples include bis[2-(2’-benzo[4,5-α]thienyl)pyridine-N,C3’]iridium(III) acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinoline-N,C2’)iridium(III) acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP), and other organometallic complexes.

[0906] In addition, rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: Eu(DBM)3(Phen)), tris[1-(2-thienoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: Eu(TTA)3(Phen)), etc. can be used as phosphorescent materials because they emit light from rare earth metal ions (electronic transitions between different multiplicities).

[0907] Host material of the light-emitting layer

[0908] The light-emitting layer can be configured to disperse the above dopant material in other materials (host materials). It is preferable to use a material with a lowest unoccupied molecular orbital energy level (LUMO energy level) higher than that of the dopant material and a highest occupied molecular orbital energy level (HOMO energy level) lower than that of the dopant material.

[0909] As the host material, for example,

[0910] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes,

[0911] (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives,

[0912] (3) Carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or condensed aromatic compounds such as derivatives,

[0913] (4) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives.

[0914] For example, the following can be used: tris(8-hydroxyquinoline)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-hydroxyquinoline)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviation: BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviation: ZnBTZ), etc. metal complexes;

[0915] 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2’,2”-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), etc. heterocyclic compounds;

[0916] 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9’-bianthracene (abbreviation: BANT), 9,9’-(stilbene-3,3’-diyl)diphenanthrene (abbreviation: DPNS), 9,9’-(stilbene-4,4’-diyl)diphenanthrene (abbreviation: DPNS2), 3,3’,3”-(benzene-1,3,5-triyl)tripyrene (abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenyl Equivalent fused aromatic compounds; and

[0917] N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: CzAlPA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazol-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) and other aromatic amine compounds. Two or more host materials can be used.

[0918] In particular, in the case of a blue fluorescent element, the following anthracene compounds are preferably used as the host material.

[0919] [Chemical formula 122]

[0920]

[0921] [Chemical formula 123]

[0922]

[0923] [Chemical formula 124]

[0924]

[0925] In one aspect of the organic EL element according to the present invention, when the light emitting layer includes a first light emitting layer and a second light emitting layer, at least one of the components constituting the first light emitting layer is different from the components constituting the second light emitting layer. For example, there can be mentioned a case where the dopant material contained in the first light emitting layer is different from the dopant material contained in the second light emitting layer, and a case where the host material contained in the first light emitting layer is different from the host material contained in the second light emitting layer.

[0926] In the organic EL element of the present invention, the light-emitting layer may contain a light-emitting compound that exhibits fluorescence emission with a main peak peak wavelength of 500 nm or less (hereinafter, sometimes simply referred to as "fluorescent light-emitting compound").

[0927] The method for measuring the main peak peak wavelength of the compound is as described below. Prepare a 5 μmol / L toluene solution of the compound to be measured and add it to a quartz cuvette, and measure the emission spectrum of the sample at room temperature (300 K) (the vertical axis is set as the emission intensity and the horizontal axis is set as the wavelength). The emission spectrum can be measured by a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Technologies Corporation. It should be noted that the emission spectrum measuring device is not limited to the device used here.

[0928] In the emission spectrum, the peak wavelength of the emission spectrum with the maximum emission intensity is defined as the main peak peak wavelength. It should be noted that in this specification, the main peak peak wavelength is sometimes referred to as the fluorescence emission main peak peak wavelength (FL-peak).

[0929] The above-mentioned fluorescent light-emitting compound may be the above-mentioned dopant material or the above-mentioned host material.

[0930] In the case where the light-emitting layer is a single layer, only one of the dopant material and the host material may be the above-mentioned fluorescent light-emitting compound, or both may be the above-mentioned fluorescent light-emitting compound.

[0931] In addition, in the case where the light-emitting layer includes a first light-emitting layer (anode side) and a second light-emitting layer (cathode side), only one of the first light-emitting layer and the second light-emitting layer may include the above-mentioned fluorescent light-emitting compound, or both of these light-emitting layers may include the above-mentioned fluorescent light-emitting compound. In the case where the first light-emitting layer includes the above-mentioned fluorescent light-emitting compound, only one of the dopant material and the host material included in the first light-emitting layer may be the above-mentioned fluorescent light-emitting compound, or both may be the above-mentioned fluorescent light-emitting compound. In addition, in the case where the second light-emitting layer includes the above-mentioned fluorescent light-emitting compound, only one of the dopant material and the host material included in the second light-emitting layer may be the above-mentioned fluorescent light-emitting compound, or both may be the above-mentioned fluorescent light-emitting compound.

[0932] Electron transport region

[0933] The electron transport region is composed of an electron injection layer, an electron transport layer, a hole blocking layer, etc. Any layer in the electron transport region, especially the electron transport layer, preferably contains one or more selected from alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes containing alkali metals, organic complexes containing alkaline earth metals, and organic complexes containing rare earth metals.

[0934] Electron transport layer

[0935] The electron transport layer is a layer containing a material with high electron transport property (electron transport material), formed between the light-emitting layer and the cathode, or formed between the electron injection layer and the light-emitting layer when the electron injection layer exists.

[0936] 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 present invention, the above-mentioned single-layer electron transport layer is preferably adjacent to the light-emitting layer, or the electron transport layer closest to the anode in the above-mentioned multi-layer structure, for example, the first electron transport layer of the above-mentioned two-layer structure, is preferably adjacent to the light-emitting layer. In another aspect of the present invention, a hole blocking layer or the like described later can be interposed between the above-mentioned single-layer electron transport layer and the light-emitting layer, or between the electron transport layer closest to the light-emitting layer in the above-mentioned multi-layer structure and the light-emitting layer.

[0937] The electron transport layer can be used, for example,

[0938] (1) Metal complexes such as aluminum complexes, beryllium complexes, zinc complexes, etc.,

[0939] (2) Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives, etc.,

[0940] (3) Polymer compounds.

[0941] Examples of the metal complex include: tris(8-hydroxyquinoline)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-hydroxyquinoline)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (abbreviation: BeBq 2 )), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviation: BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviation: ZnBTZ).

[0942] As heteroaromatic compounds, examples thereof include: 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), 4,4'-bis(5-methylbenzooxazol-2-yl)stilbene (abbreviation: BzOs).

[0943] As polymer compounds, examples thereof include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).

[0944] The above materials are materials having an electron mobility of 10 -6 cm 2 / Vs or more. It should be noted that as long as the material has higher electron transportability than hole transportability, materials other than the above can be used for the electron transport layer.

[0945] Electron injection layer

[0946] The electron injection layer is a layer containing a material with high electron injection property. The electron injection layer can use alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), rare earth metals such as europium (Eu) and ytterbium (Yb), and compounds containing these metals. As such compounds, examples include: alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, rare earth metal oxides, rare earth metal halides, and rare earth metal-containing organic complexes. In addition, a plurality of these compounds can be used in combination.

[0947] In addition, a material obtained by containing an alkali metal, an alkaline earth metal, or a compound thereof in a material having electron transportability can be used. Specifically, a material obtained by containing magnesium (Mg) in Alq can be used, etc. It should be noted that at this time, electron injection from the cathode can be performed more efficiently.

[0948] Alternatively, a composite material formed by mixing an organic compound and a donor can also be used as the electron injection layer. Since the organic compound accepts electrons from the donor in such a composite material, the electron injection property and electron transport property are excellent. At this time, as the organic compound, a material excellent in the transport of the accepted electrons is preferable. Specifically, for example, the materials constituting the electron transport layer described above (metal complexes, heteroaromatic compounds, etc.) can be used. As the donor, any material that exhibits a donating property to the organic compound can be used. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and examples include lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. In addition, alkali metal oxides and alkaline earth metal oxides are preferable, and examples include lithium oxide, calcium oxide, barium oxide, etc. In addition, a Lewis base such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviation: TTF) can also be used.

[0949] Cathode

[0950] The cathode preferably uses a metal, alloy, conductive compound, and their mixture, etc. with a small work function (specifically, 3.8 eV or less). As specific examples of such cathode materials, elements belonging to Group 1 or Group 2 of the periodic table can be cited, that is, 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 (such as MgAg and AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them, etc.

[0951] It should be noted that when forming the cathode using an alkali metal, alkaline earth metal, or an alloy containing them, a vacuum evaporation method or a sputtering method can be used. In addition, when using silver paste, etc., a coating method, an inkjet method, etc. can be used.

[0952] It should be noted that by providing an electron injection layer, cathodes can be formed using various conductive materials such as Al, Ag, ITO, graphene, indium tin oxide containing silicon or silicon oxide, etc., regardless of the size of the work function. These conductive materials can be formed into films using a sputtering method, an inkjet method, a spin coating method, etc.

[0953] Insulating layer

[0954] Since an electric field is applied to an ultrathin film in an organic EL element, pixel defects due to leakage and short circuits are likely to occur. To prevent this, an insulating layer formed of an insulating thin film layer can also be inserted between a pair of electrodes.

[0955] As materials that can be used for the insulating layer, for example, 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, vanadium oxide, etc. can be cited. It should be noted that their mixtures and laminates can also be used.

[0956] Spacer layer

[0957] For the above spacer layer, for example, in the case where a fluorescent light-emitting layer and a phosphorescent light-emitting layer are laminated, it is a layer provided between the fluorescent light-emitting layer and the phosphorescent light-emitting layer for the purpose of preventing excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer or adjusting the carrier balance. In addition, the spacer layer can also be provided between multiple phosphorescent light-emitting layers.

[0958] Since the spacer layer is provided between the light-emitting layers, a material having both electron-transporting properties and hole-transporting properties is preferably used. In addition, in order to prevent the diffusion of triplet energy in adjacent phosphorescent light-emitting layers, the triplet energy is preferably 2.6 eV or more. As materials for the spacer layer, the same materials as those for the above hole-transporting layer can be cited.

[0959] Blocking layer

[0960] It is also possible to dispose blocking layers such as an electron blocking layer, a hole blocking layer, and an exciton blocking layer adjacent to the light-emitting layer. The electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole-transporting layer, and the hole blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron-transporting layer. The exciton blocking layer has a function of preventing excitons generated in the light-emitting layer from diffusing to the surrounding layers and thus confining the excitons within the light-emitting layer.

[0961] Each layer of the above organic EL element can be formed by a conventionally known vapor deposition method, coating method, etc. For example, vapor deposition methods such as vacuum vapor deposition method and molecular beam epitaxy (MBE method) can be used, or known methods based on coating methods such as dip coating method, spin coating method, casting method, bar coating method, roll coating method, etc. using a solution of a compound for forming the layer can be used.

[0962] There is no particular limitation on the film thickness of each layer. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur. On the contrary, if it is too thick, a high driving voltage is required and the efficiency deteriorates. Therefore, it is usually 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm.

[0963] In the organic EL element having a hole-transporting layer with a two-layer structure or a three-layer structure of the present invention, the total thickness of the thickness of the first hole-transporting layer and the thickness of the second hole-transporting layer is preferably 30 nm or more and 150 nm or less, and more preferably 40 nm or more and 130 nm or less.

[0964] In addition, in one embodiment of the present invention, the thickness of the second hole transport layer in the two-layer structure or three-layer structure is preferably 5 nm or more, more preferably 20 nm or more, further preferably 25 nm or more, particularly preferably 35 nm or more, and preferably 100 nm or less.

[0965] In addition, in one embodiment of the present invention, the thickness of the hole transport layer adjacent to the light-emitting layer is preferably 5 nm or more, more preferably 20 nm or more, further preferably 25 nm or more, particularly preferably 30 nm or more, and preferably 100 nm or less.

[0966] In addition, in the organic EL element having the two-layer structure or three-layer structure hole transport layer of the present invention, the ratio of the film thickness D2 of the second hole transport layer to the film thickness D1 of the first hole transport layer is preferably 0.3 < D2 / D1 < 4.0, more preferably 0.5 < D2 / D1 < 3.5, and further preferably 0.75 < D2 / D1 < 3.0.

[0967] As a preferred embodiment of the organic EL element of the present invention, for example, the following can be cited:

[0968] (1) An organic EL element having a two-layer structure hole transport layer

[0969] · The first embodiment in which the second hole transport layer contains the inventive compound and the first hole transport layer does not contain the inventive compound;

[0970] · The second embodiment in which both the first hole transport layer and the second hole transport layer contain the inventive compound;

[0971] · The third embodiment in which the first hole transport layer contains the inventive compound and the second hole transport layer does not contain the inventive compound;

[0972] (2) An organic EL element having a three-layer structure hole transport layer

[0973] · The fourth embodiment in which the first hole transport layer contains the inventive compound and the second hole transport layer and the third hole transport layer do not contain the inventive compound;

[0974] · The fifth embodiment in which the second hole transport layer contains the inventive compound and the first hole transport layer and the third hole transport layer do not contain the inventive compound;

[0975] · The sixth embodiment in which the third hole transport layer contains the inventive compound and the first hole transport layer and the second hole transport layer do not contain the inventive compound;

[0976] · The seventh embodiment in which the first hole transport layer and the second hole transport layer contain the inventive compound and the third hole transport layer does not contain the inventive compound;

[0977] ·Embodiment 8 in which the first hole transport layer and the third hole transport layer contain the inventive compound and the second hole transport layer does not contain the inventive compound;

[0978] ·Embodiment 9 in which the second hole transport layer and the third hole transport layer contain the inventive compound and the first hole transport layer does not contain the inventive compound;

[0979] ·Embodiment 10 in which the first to third hole transport layers all contain the inventive compound; and so on.

[0980] Electronic device

[0981] An organic EL element according to an embodiment of the present invention can be used in electronic devices such as display devices and light-emitting devices. As the display device, for example, display components such as an organic EL panel module, a television, a mobile phone, a tablet computer, or a personal computer can be cited. As the light-emitting device, for example, lighting or vehicle lamps can be cited.

[0982] The above organic EL element can be used in display devices such as display components such as an organic EL panel module, a television, a mobile phone, and a personal computer, and light-emitting devices such as lighting and vehicle lamps.

[0983] Examples

[0984] Hereinafter, the present invention will be described in further detail using examples, and the present invention is not limited to the following examples.

[0985] The inventive compound used in the production of the organic EL element (I) of Examples 1 and 2

[0986] [Chemical formula 125]

[0987]

[0988] The comparative compound used in the production of the organic EL element (I) of Comparative Example 1

[0989] [Chemical formula 126]

[0990]

[0991] Other compounds used in the production of the organic EL element (I) of Examples 1 and 2 and Comparative Example 1

[0992] [Chemical formula 127]

[0993]

[0994] Fabrication of the organic EL element (I)

[0995] Example 1

[0996] A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then subjected to UV ozone cleaning for 30 minutes. The film thickness of ITO was set to 130 nm.

[0997] The cleaned glass substrate with the ITO transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, Compound Inv-1 and Compound HA were co-evaporated on the side with the transparent electrode formed to cover the transparent electrode, forming a hole injection layer with a film thickness of 10 nm. The mass ratio of Compound Inv-1 to Compound HA (Compound Inv-1:HA) was 97:3.

[0998] Next, Compound Inv-1 was evaporated on the hole injection layer to form a first hole transport layer with a film thickness of 45 nm.

[0999] Next, Compound HT-1 was evaporated on the first hole transport layer to form a second hole transport layer with a film thickness of 40 nm.

[1000] Next, Compound HT-2 was evaporated on the second hole transport layer to form a third hole transport layer with a film thickness of 5 nm.

[1001] Next, Compound BH-1 (host material) and Compound BD-1 (dopant material) were co-evaporated on the third hole transport layer to form a light-emitting layer with a film thickness of 25 nm. The mass ratio of Compound BH-1 to Compound BD-1 (BH-1:BD-1) was 98:2.

[1002] Next, Compound ET-1 was evaporated on the light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

[1003] Next, Compound ET-2 was evaporated on the first electron transport layer to form a second electron transport layer with a film thickness of 25 nm.

[1004] Next, LiF was evaporated on the second electron transport layer to form an electron injection electrode with a film thickness of 1 nm.

[1005] Then, metal Al was evaporated on the electron injection electrode to form a metal cathode with a film thickness of 80 nm.

[1006] The layer structure of the organic EL element (I) obtained by such operations is shown below.

[1007] ITO(130) / Compound Inv-1: HA = 97:3(10) / Compound Inv-1(45) / HT-1(40) / HT-2(5) / BH-l: BD-1 = 98:2(25) / ET-1(5) / ET-2(25) / LiF(1) / Al(80)

[1008] In the above layer structure, the numbers in parentheses are the film thickness (nm), and the ratios are mass ratios.

[1009] Example 2 and Comparative Example 1

[1010] An organic EL element was fabricated in the same manner as in Example 1, except that Compound Inv-2 or Comparative Compound Ref-1 was used instead of Compound Inv-1.

[1011] Evaluation of the organic EL element

[1012] For the obtained organic EL element (I), the driving voltage and external quantum efficiency were measured.

[1013] (1) Measurement of the driving voltage

[1014] A voltage was applied to the organic EL element (I) such that the current density was 10 mA / cm 2 , and the voltage at this time (unit: V) was measured. The results are shown in Table 1.

[1015] (2) Measurement of the external quantum efficiency (EQE)

[1016] The obtained organic EL element (I) was driven at a constant DC current density of 10 mA / cm at room temperature 2 . The luminance was measured using a luminance meter (Minolta Spectral Luminance Radiometer CS-1000), and the external quantum efficiency (%) was calculated from the results. The results are shown in Table 1.

[1017] [Table 1]

[1018] Table 1

[1019]

[1020] From the results in Table 1, it is clearly understood that the organic EL elements (I) of Examples 1 and 2 have a lower driving voltage and a higher external quantum efficiency than the organic EL element (I) of Comparative Example 1.

[1021] The inventive compound used in the fabrication of the organic EL element (II) of Example 3

[1022] [Chemical formula 128]

[1023]

[1024] Comparative compound used in the production of the organic EL element (II) of Comparative Example 2

[1025] [Chemical formula 129]

[1026]

[1027] Other compounds used in the production of the organic EL element (II) of Example 3 and Comparative Example 2

[1028] [Chemical formula 130]

[1029]

[1030] Fabrication of the organic EL element (II)

[1031] Example 3

[1032] A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) having dimensions of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then subjected to UV ozone cleaning for 30 minutes. The film thickness of the ITO was set to 130 nm.

[1033] The cleaned glass substrate with the ITO transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, Compound Inv-2 and Compound HA were co-evaporated in a manner covering the transparent electrode on the side where the transparent electrode was formed to form a hole injection layer with a film thickness of 10 nm. The mass ratio of Compound Inv-2 to Compound HA (Compound Inv-2:HA) was 95:5.

[1034] Next, Compound Inv-2 was evaporated on the hole injection layer to form a first hole transport layer with a film thickness of 30 nm.

[1035] Next, Compound HT-3 was evaporated on the first hole transport layer to form a second hole transport layer with a film thickness of 40 nm.

[1036] Next, Compound HT-2 was evaporated on the second hole transport layer to form a third hole transport layer with a film thickness of 15 nm.

[1037] Next, Compound BH-2 (host material) and Compound BD-2 (dopant material) were co-evaporated on the third hole transport layer to form a light-emitting layer with a film thickness of 20 nm. The mass ratio of Compound BH-2 to Compound BD-2 (BH-2:BD-2) was 98:2.

[1038] Next, Compound ET-1 was evaporated on the light-emitting layer to form a first electron transport layer with a film thickness of 10 nm.

[1039] Next, compound ET-3 and Li were co-evaporated on the first electron transport layer to form a second electron transport layer with a thickness of 20 nm, which also served as an electron injection layer. The mass ratio of compound ET-3 to Li (ET-3:Li) was 96:4.

[1040] Then, metal Al was evaporated on the second electron transport layer to form a metal cathode with a thickness of 80 nm.

[1041] The layer structure of the organic EL element (II) obtained by such operations is shown below.

[1042] ITO(130) / Compound Inv-2:HA = 95:5(10) / Compound Inv-2(30) / HT-3(40) / HT-2(15) / BH-2:BD-2 = 98:2(20) / ET-1(10) / ET-3:Li == 96:4(20) / / A1(80)

[1043] In the above layer structure, the numbers in parentheses are the film thickness (nm), and the ratios are mass ratios.

[1044] Comparative Example 2

[1045] An organic EL element (II) was fabricated in the same manner as in Example 3, except that comparative compound Ref-1 was used instead of compound Inv-2.

[1046] Evaluation of the organic EL element (II)

[1047] For the obtained organic EL element (II), the driving voltage and external quantum efficiency (EQE) were measured using the same method as the evaluation of the organic EL element (I). The results are shown in Table 2.

[1048] [Table 2]

[1049] Table 2

[1050]

[1051] It is clearly understood from the results in Table 2 that the organic EL element (II) of Example 3 has a lower driving voltage and a higher external quantum efficiency than the organic EL element (II) of Comparative Example 2.

[1052] Inventive compounds used in the fabrication of the organic EL elements (III) of Examples 4 and 5

[1053] [Chemical formula 131]

[1054]

[1055] Comparative compound used in the fabrication of the organic EL element (III) of Comparative Example 3

[1056] [Chemical formula 132]

[1057]

[1058] Other compounds used in the manufacture of the organic EL element (III) of Example 4 and 5, and Comparative Example 3

[1059] [Chemical formula 133]

[1060]

[1061] Fabrication of the organic EL element (HI)

[1062] Example 4

[1063] A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then subjected to UV ozone cleaning for 30 minutes. The film thickness of ITO was set to 130 nm.

[1064] The cleaned glass substrate with the ITO transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, Compound Inv-1 and Compound HA were co-evaporated in a manner to cover the transparent electrode on the side where the transparent electrode was formed, forming a hole injection layer with a film thickness of 10 nm. The mass ratio of Compound Inv-1 to Compound HA (Compound Inv-1:HA) was 99:1.

[1065] Next, Compound Inv-1 was evaporated on the hole injection layer to form a first hole transport layer with a film thickness of 77.5 nm.

[1066] Next, Compound HT-4 was evaporated on this first hole transport layer to form a second hole transport layer with a film thickness of 7.5 nm.

[1067] Next, a BH (host material):BD-3 (dopant material) film with a film thickness of 20 nm was formed on this second hole transport layer. This BH:BD-3 film functioned as a light-emitting layer. The BH [compounds BH-3 and BH-4 (both host materials)] contained in the light-emitting layer was 60:40 by mass ratio, and the concentration of BD-3 was 2% by mass relative to the entire light-emitting layer.

[1068] Next, Compound ET-4 was evaporated on this light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

[1069] Next, the compound ET-5 and Liq were co-evaporated on the first electron transport layer to form a second electron transport layer with a film thickness of 25 nm. The mass ratio of the compound ET-5 to Liq (ET-5:Liq) was 67:33.

[1070] Next, Yb was evaporated on the second electron transport layer to form an electron injection electrode with a film thickness of 1 nm.

[1071] Then, metal Al was evaporated on the electron injection electrode to form a metal cathode with a film thickness of 80 nm.

[1072] The layer structure of the organic EL element (III) obtained by such operations is shown below.

[1073] ITO(130) / Compound Inv-1:HA = 99:1(10) / Compound Inv-1(77.5) / HT-4(7.5) / BH-3:BH-4:BD-3 = 60:40:2(20) / ET-4(5) / ET-5:

[1074] Liq = 67:33(25) / Yb(1) / Al(80)

[1075] In the above layer structure, the numbers in parentheses are the film thickness (nm), and the ratios are mass ratios.

[1076] Example 5 and Comparative Example 3

[1077] Instead of the compound Inv-1, the compound Inv-2 or the comparative compound Ref-1 was used, and an organic EL element (III) was produced in the same manner as in Example 4 except for this.

[1078] Evaluation of the organic EL element (III)

[1079] For the obtained organic EL element (III), the driving voltage and the external quantum efficiency (EQE) were measured by the same method as the evaluation of the organic EL element (I). The results are shown in Table 3.

[1080] [Table 3]

[1081] Table 3

[1082]

[1083] It is clearly understood from the results in Table 3 that the organic EL elements (III) of Examples 4 and 5 have a lower driving voltage and a higher external quantum efficiency than the organic EL element (III) of Comparative Example 3.

[1084] Inventive compounds used in the production of the organic EL elements (IV) of Examples 6 and 7

[1085] [Chemical Formula 134]

[1086]

[1087] Comparative compound used in the production of the organic EL element (IV) of Comparative Example 4

[1088] [Chemical Formula 135]

[1089]

[1090] Other compounds used in the production of the organic EL elements (IV) of Examples 6 and 7, and Comparative Example 4

[1091] [Chemical Formula 136]

[1092]

[1093] Fabrication of the organic EL element (IV)

[1094] Example 6

[1095] A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) having dimensions of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then subjected to UV-ozone cleaning for 30 minutes. The film thickness of the ITO was set to 130 nm.

[1096] The cleaned glass substrate with the ITO transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, Compound Inv-1 and Compound HA were co-evaporated in a manner that covered the transparent electrode on the side where the transparent electrode was formed to form a hole injection layer with a film thickness of 10 nm. The mass ratio of Compound Inv-1 to Compound HA (Compound Inv-1:HA) was 99:1.

[1097] Next, Compound Inv-1 was evaporated on the hole injection layer to form a first hole transport layer with a film thickness of 37.5 nm.

[1098] Next, Compound HT-5 was evaporated on the first hole transport layer to form a second hole transport layer with a film thickness of 40 nm.

[1099] Next, Compound HT-4 was evaporated on the second hole transport layer to form a third hole transport layer with a film thickness of 7.5 nm.

[1100] Next, a film of BH (host material): BD-3 (dopant material) with a film thickness of 20 nm was formed on the second hole transport layer. This BH:BD-3 film functions as a light-emitting layer. The BH [chemical compounds BH-3 and BH-4 (both host materials)] contained in the light-emitting layer is 60:40 by mass ratio, and the concentration of BD-3 is 2% by mass relative to the entire light-emitting layer.

[1101] Next, the compound ET-4 was evaporated on this light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

[1102] Next, the compounds ET-5 and Liq were co-evaporated on the first electron transport layer to form a second electron transport layer with a film thickness of 25 nm. The mass ratio of compound ET-5 to Liq (ET-5:Liq) is 67:33.

[1103] Next, Yb was evaporated on the second electron transport layer to form an electron injection electrode with a film thickness of 1 nm.

[1104] Then, metal Al was evaporated on this electron injection electrode to form a metal cathode with a film thickness of 80 nm.

[1105] The layer structure of the organic EL element (IV) obtained by such operations is shown below.

[1106] ITO (130) / Compound Inv-1:HA = 99:1 (10) / Compound Inv-1 (37.5) / HT-5 (40) / HT-4 (7.5) / BH-3:BH-4:BD-3 = 60:40:

[1107] 2 (20) / ET-4 (5) / ET-5:Liq = 67:33 (25) / Yb (1) / Al (80)

[1108] In the above layer structure, the numbers in parentheses are film thicknesses (nm), and the ratios are mass ratios.

[1109] Example 7 and Comparative Example 4

[1110] An organic EL element (IV) was fabricated in the same manner as in Example 6, except that compound Inv-2 or comparative compound Ref-1 was used instead of compound Inv-1.

[1111] Evaluation of the organic EL element (IV)

[1112] For the obtained organic EL element (IV), the driving voltage and external quantum efficiency (EQE) were measured using the same method as the evaluation of the organic EL element (I). The results are shown in Table 4.

[1113] [Table 4]

[1114] Table 4

[1115]

[1116] It is clearly known from the results in Table 4 that the organic EL element (IV) of Examples 6 and 7 has a higher external quantum efficiency than the organic EL element (IV) of Comparative Example 4.

[1117] The inventive compound synthesized in the synthesis example

[1118] [Chemical formula 137]

[1119]

[1120] Intermediate Synthesis Example 1: Synthesis of Intermediate A

[1121] [Chemical formula 138]

[1122]

[1123] Under an argon atmosphere, a mixture of 10 g (54.6 mmol) of 10H-phenoxazine, 6.57 mL (54.6 mmol) of 2-bromo-4-chloro-1-fluorobenzene, 35.6 g (109 mmol) of cesium carbonate, and 109 mL of DMF was stirred under reflux at the boiling point for 7 hours. After cooling the reaction solution to room temperature, it was concentrated under reduced pressure. The residue was extracted with toluene, washed with saturated brine, dehydrated with magnesium sulfate for the organic layer, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 10.2 g of a white solid (Intermediate A-1). The yield was 50%.

[1124] Under an argon atmosphere, a mixture of 10 g (26.8 mmol) of Intermediate A-1, 0.30 g (1.34 mmol) of palladium acetate, 1.98 g (5.37 mmol) of tricyclohexylphosphonium tetrafluoroborate, 7.42 g (53.7 mmol) of potassium carbonate, and 500 mL of dimethylacetamide was stirred at 150 °C for 7 hours. After cooling the reaction solution to room temperature, it was concentrated under reduced pressure. The residue was extracted with toluene and washed with saturated brine. The organic layer was dehydrated with magnesium sulfate, concentrated under reduced pressure, and the precipitated solid was filtered to obtain 5.47 g of a pale yellow solid (Intermediate A). The yield was 70%.

[1125] Synthesis Example 1: Synthesis of Compound Inv-1

[1126] [Chemical formula 139]

[1127]

[1128] Under an argon atmosphere, a mixture of 8.31 g (13.9 mmol) of N-(biphenyl-4-yl)-N-{4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl}-N-(1,1':4',1''-terphenyl-4-yl)amine, 3.37 g (11.6 mmol) of Intermediate A, 0.212 g (0.23 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.4410.267 g (0.92 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos), 17.3 mL of 2M aqueous potassium phosphate solution, and 116 mL of 1,4-dioxane was stirred at 90 °C for 6.5 hours. After cooling the reaction solution to room temperature, it was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 2.89 g of a white solid. The yield was 34%.

[1129] The obtained substance was subjected to mass spectrometry, and the result was Compound Inv-1, with m / e = 729 relative to a molecular weight of 728.90.

[1130] Synthesis Example 2: Synthesis of Compound Inv-2

[1131] [Chemical Formula 140]

[1132]

[1133] In Synthesis Example 1, 2-[4-[bis(4-biphenylyl)amino]phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of N-(biphenyl-4-yl)-N-{4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl}-N-(1,1':4',1''-terphenyl-4-yl)amine, and the same operations were carried out otherwise to obtain 3.29 g of a white solid. The yield was 72%.

[1134] The obtained substance was subjected to mass spectrometry, and the result was Compound Inv-2, with m / e = 653 relative to a molecular weight of 652.80.

[1135] Symbol Explanation

[1136] 1, 11, 12 Organic EL element

[1137] 2 Substrate

[1138] 3 Anode

[1139] 4 Cathode

[1140] 5 Light-emitting layer

[1141] 6 Hole transport region (hole transport layer)

[1142] 6a Hole injection layer

[1143] 6b First hole transport layer

[1144] 6c Second hole transport layer

[1145] 6d Third hole transport layer

[1146] 7 Electron transport region (electron transport layer)

[1147] 7a First electron transport layer

[1148] 7b Second electron transport layer

[1149] 10, 20, 30 Light-emitting units

Claims

1. A compound represented by the following formula (1), In formula (1), N * is the central nitrogen atom, Ar 1 and Ar 2 each independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, L 1 and L 2 each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms, L 3 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, R 1 ~R 10 Each independently represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms, a group represented by -Si(R 901 )(R 902 )(R 903 ), a group represented by -O-(R 904 ), or a group represented by -S-(R 905 ). R 901 ~R 905 Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In R 901 When there are two or more, two or more Rs 901 are the same as or different from each other In R 902 When there are two or more, two or more Rs 902 are the same as or different from each other In R 903 When there are two or more, two or more Rs 903 are the same as or different from each other, In R 904 When there are two or more, two or more Rs 904 are the same as or different from each other In R 905 When there are two or more, two or more Rs 905 are the same as or different from each other, wherein, Selected from R 2 to R 10 Two adjacent ones among them are optionally bonded to each other to form a substituted or unsubstituted benzene ring, or are not bonded to each other and thus do not form a ring. X 1 is an oxygen atom or a sulfur atom.

2. The compound according to claim 1, wherein, L 3 is a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms.

3. The compound according to claim 1 or 2, wherein, L 3 is a substituted or unsubstituted arylene group having 6 to 12 ring-forming carbon atoms.

4. The compound according to any one of claims 1 to 3, wherein, X 1 is an oxygen atom.

5. The compound according to any one of claims 1 to 4, wherein, Ar 1 and Ar 2 are each independently represented by the following formula (2A), (2B), (2C), (2D), (2E), (2F), or (2G): In formula (2A), * 21 is the bonding position with L 1 or L 2 ​ 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 bonded to *23 Not R of the single bond 101 ~R 105 and R 106 ~R 110 Each independently represents a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms, R selected from those other than said single bond 101 ~R 105 Two adjacent ones among them do not bond to each other and do not form a ring R selected from those other than said single bond 106 ~R 110 Two adjacent ones among them do not bond to each other and do not form a ring, R 111 ~R 115 Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. Selected from R 111 to R 115 Two adjacent ones among them do not bond to each other and do not form a ring m is 0, 1 or 2, n is 0 or 1, excluding the case where m is 2 and n is 0, When m = 0 and n = 0, *23 represents *21, When m = 0 and n = 1, *22 represents *21, When m = 1 and n = 0, *23 represents *22, In formula (2B), * 24 is the bonding position with L 1 or L 2 of Selected from R 121 ~R 128 One of them is a single bond bonded to *25 Not R of the single bond 121 ~R 128 Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. R selected from those other than the single bond 121 ~R 128 Two adjacent ones among them do not bond to each other and do not form a ring In formula (2C), * 26 is the bonding position with L 1 or L 2 of the bonding position Selected from R 131 to R 140 One of them is a single bond bonded to *27 Not R of the single bond 131 ~R 140 Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. R selected from those other than the single bond 131 ~R 140 Two adjacent ones among them do not bond to each other and do not form a ring In formula (2D), *28 is the bonding position with L 1 or L 2 and X 11 is an oxygen atom, a sulfur atom, CR a R b or NR c , R a and R b each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and optionally bond to each other to form a substituted or unsubstituted ring structure, or do not bond to each other and do not form a ring R c is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms. n is 0 or 1, When n is 0, one selected from R a , R b , R c and R 141 ~R 148 is a single bond bonded to *29, or R a or R b may represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, R a or R b a substituted or unsubstituted ring structure that may be bonded to each other to form, or R c a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that may be represented is bonded to *29 via a single bond, When n is 1, R 141 and R 142 , R 142 and R 143 , or R 143 and R 144 One of them is a single bond bonded to *a, and the other is a single bond bonded to *b. R selected from single bonds not bonded to *a and *b 141 ~R 144 , R 145 ~R 148 , R a , R b , R c , and R 200 ~R 203 One of them is a single bond bonded to *29, or R a or R b may represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or R a or R b a substituted or unsubstituted ring structure that may be bonded to each other to form, or R c a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that may be represented is bonded to *29 via a single bond, Not R of the single bond 141 ~R 148 and not R of the single bond 200 ~R 203 Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms, R selected from those other than the said single bond 141 ~R 148 and R other than the said single bond 200 ~R 203 Among them, two adjacent ones do not bond to each other and do not form a ring In formula (2E), * 30 is the bonding position with L 1 or L 2 of Selected from R 151 to R 155 One of them is a single bond bonded to *31, and the other selected from R 151 to R 155 is a single bond bonded to *32 Not R of the single bond 151 ~R 155 Each independently represents a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group. R selected from those other than the said single bond 151 ~R 155 Two adjacent ones among them do not bond to each other and do not form a ring R 161 ~R 165 and R 171 ~R 175 Each independently represents a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms, R selected from other than a hydrogen atom 161 ~R 165 in which at least one pair of two adjacent ones are optionally bonded to each other to form one or more unsubstituted benzene rings, or are not bonded to each other to form no ring R selected from other than a hydrogen atom 171 ~R 175 in which at least one pair of two adjacent ones are optionally bonded to each other to form one or more unsubstituted benzene rings, or are not bonded to each other and thus do not form a ring In formula (2F), * 32 is the bonding position with L 1 or L 2 ​ Selected from R 181 to R 192 One of them is a single bond bonded to *33, Not R of the single bond 181 ~R 192 Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. R selected from those other than the said single bond 181 ~R 192 Two adjacent ones among them do not bond to each other and do not form a ring.

6. The compound according to claim 5, wherein, Ar 1 and Ar 2 are each independently represented by formula (2A) or (2D).

7. The compound according to claim 5 or 6, wherein, Ar 1 and Ar 2 are each independently represented by formula (2A).

8. The compound according to any one of claims 1 to 7, wherein, contains at least 1 deuterium atom.

9. A material for an organic electroluminescent element, which contains the compound according to any one of claims 1 to 8.

10. An organic electroluminescent element, which has a cathode, an anode, and an organic layer located between the cathode and the anode, the organic layer includes a light-emitting layer, and at least 1 layer of the organic layer contains the compound according to any one of claims 1 to 8.

11. The organic electroluminescent element according to claim 10, 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.

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

13. The organic electroluminescent element according to claim 12, wherein, the light-emitting layer is directly in contact with the second hole transport layer.

14. The organic electroluminescent element according to claim 12 or 13, wherein, the total thickness of the thickness of the first hole transport layer and the thickness of the second hole transport layer is 30 nm or more and 150 nm or less.

15. The organic electroluminescent element according to any one of claims 10 to 14, wherein, the light-emitting layer is a single layer.

16. The organic electroluminescent element according to any one of claims 10 to 15, wherein, the light-emitting layer contains a light-emitting compound that exhibits fluorescence emission with a main peak peak wavelength of 500 nm or less.

17. The organic electroluminescent element according to any one of claims 10 to 16, wherein, the light-emitting layer contains a fluorescent dopant material.

18. An electronic device, which contains the organic electroluminescent element according to any one of claims 10 to 17.

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