Compound, Material for Organic Electroluminescent Element, Organic Electroluminescent Element, and Electronic Device

Abstract

The compound represented by the following formula (1), a material for an organic electroluminescent element containing the compound, an organic electroluminescent element containing the compound, and an electronic device containing the organic electroluminescent element. In the formula, R 1 ~R 10 、R 11 ~R 14 、L and Ar are the same as defined in the specification.

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 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 into the light-emitting region from the cathode side, and holes are injected into the light-emitting region from the anode side. 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, the development of materials that can efficiently transport electrons or holes to the light-emitting region and facilitate the recombination of electrons and holes is important for obtaining high-performance organic EL elements.

[0003] Compounds used as materials for organic electroluminescent elements are disclosed in Patent Documents 1 and 2.

[0004] Prior Art Documents

[0005] Patent Documents

[0006] Patent Document 1: WO2004 / 063159A1

[0007] Patent Document 2: WO2017 / 131380A1 Summary of the Invention

[0008] Problems to be Solved by the Invention

[0009] Conventionally, a large number of compounds for organic EL elements have been reported, but there is still a need for compounds that can further improve the performance of organic EL elements.

[0010] The present invention has been made to solve the above problems, and an object thereof is to provide a compound that can further improve 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.

[0011] Means for Solving the Problems

[0012] The present inventors repeatedly conducted in-depth studies on the performance of organic EL elements containing the compounds described in Patent Documents 1 and 2, and as a result, found that organic EL elements containing the compound represented by the following formula (1) exhibit higher performance.

[0013] In one aspect, the present invention provides a compound represented by the following formula (1).

[0014] [Chemical Formula 1]

[0015]

[0016] (In the formula, R 1 ~R 10 are each independently a hydrogen atom, a fluorine atom, a cyano group, 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, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms;

[0017] Two adjacent ones selected from R 1 ~R 10 can 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 substituted or unsubstituted ring structure;

[0018] R 11 ~R 14 are each independently a hydrogen atom, a fluorine atom, a cyano group, 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, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms;

[0019] Two adjacent ones selected from R 11 ~R 14 can 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 substituted or unsubstituted ring structure;

[0020] Ar is a substituted or unsubstituted non-fused aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted fused aryl group having 10 to 16 ring carbon atoms;

[0021] L is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and containing only six-membered rings;

[0022] Ar and L do not crosslink;

[0023] In the presence of optional substituents, the optional substituents represented by "substituted or unsubstituted" are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.)

[0024] In another aspect, the present invention provides a material for an organic EL element containing the compound represented by the above formula (1).

[0025] In another aspect, the present invention provides an organic electroluminescent element including an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer contains the compound represented by the above formula (1).

[0026] In another aspect, the present invention provides an electronic device including the above organic electroluminescent element.

[0027] Effects of the Invention

[0028] The organic EL element containing the compound represented by the above formula (1) exhibits high element performance. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] Figure 1 It is a schematic diagram showing an example of the layer structure of the organic EL element according to one aspect of the present invention.

[0030] Figure 2 It is a schematic diagram showing another example of the layer structure of the organic EL element according to one aspect of the present invention. DETAILED DESCRIPTION

[0031] [Definitions]

[0032] In the present specification, a hydrogen atom means an isotope having a different number of neutrons, that is, protium, deuterium, and tritium.

[0033] In the present specification, in a chemical structural formula, when the bonding positions of symbols such as "R" and "D" representing deuterium atoms are not clearly shown, it is assumed that a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is bonded.

[0034] In the present 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 having a structure in which atoms are bonded in a ring (for example, a monocyclic compound, a condensed ring 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 manner unless otherwise noted. 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.

[0035] In addition, when an alkyl group is substituted as a substituent on a benzene ring, for example, the number of carbon atoms in 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 in 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.

[0036] In this specification, the number of ring-forming atoms refers to the number of atoms that constitute the ring itself in a compound having a structure in which atoms are bonded in a ring (such as a monocyclic, fused-ring, and spiro-ring), such as a monocyclic compound, a fused-ring compound, a bridged-ring compound, a carbocyclic compound, and a heterocyclic compound. Atoms that do not form a ring (such as hydrogen atoms that cap the bonds of the atoms forming the ring) and atoms contained in the 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 of a pyridine ring is 6, the number of ring-forming atoms of a quinazoline ring is 10, and the number of ring-forming atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or the number of atoms constituting a substituent is not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms of a pyridine ring bonded with a hydrogen atom or a substituent is 6. In addition, for example, the number of hydrogen atoms bonded to the carbon atoms of a quinazoline ring or the atoms constituting a substituent are not included in the number of quinazoline ring-forming atoms. Therefore, the number of ring-forming atoms of a quinazoline ring bonded with a hydrogen atom or a substituent is 10.

[0037] In this specification, in the expression "ZZ group having a carbon number of XX to YY, which may be substituted or unsubstituted", the "carbon number of XX to YY" represents the carbon number of the ZZ group when it is unsubstituted, and the carbon number 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.

[0038] In this specification, in the expression "ZZ group having an atom number of XX to YY, which may be substituted or unsubstituted", the "atom number of XX to YY" represents the atom number of the ZZ group when it is unsubstituted, and the atom number 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.

[0039] 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".

[0040] In this specification, when it is described as "substituted or unsubstituted ZZ group", "unsubstituted" means that the hydrogen atom in the ZZ group is not replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom or a tritium atom.

[0041] In addition, in this specification, when it is described as "substituted or unsubstituted ZZ group", "substituted" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. Similarly, when it is described 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.

[0042] "Substituents described in this specification"

[0043] The substituents described in this specification are described below. Unless otherwise specified, each substituent described in this specification is defined as follows.

[0044] Unless otherwise specified in this specification, the ring-forming carbon number of the "unsubstituted aryl" described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0045] Unless otherwise specified in this specification, the number of ring-forming atoms of the "unsubstituted heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0046] Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkyl" described in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0047] Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkenyl" described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0048] Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkynyl" described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0049] Unless otherwise specified in this specification, the ring-forming carbon number of the "unsubstituted cycloalkyl" described in this specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6.

[0050] Unless otherwise specified in this specification, the ring-forming carbon number of the "unsubstituted arylene" described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0051] Unless otherwise specified in this specification, the number of ring-forming atoms of the "unsubstituted divalent heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0052] The number of carbon atoms of the "unsubstituted alkylene group" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified in this specification.

[0053] · "Substituted or unsubstituted aryl group"

[0054] As specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification, the following unsubstituted aryl groups (specific example group G1A) and substituted aryl groups (specific example group G1B) can be cited. (Here, the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group", and the substituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is a "substituted aryl group".) In this specification, when only "aryl group" is expressed, it includes both "unsubstituted aryl group" and "substituted aryl group".

[0055] The "substituted aryl group" refers to a group in which one or more hydrogen atoms of the "unsubstituted aryl group" have been replaced by substituents. As the "substituted aryl group", for example, groups in which one or more hydrogen atoms of the "unsubstituted aryl group" in the following specific example group G1A have been replaced by substituents, and examples of the substituted aryl groups in the following specific example group G1B can be cited. It should be noted that the examples of the "unsubstituted aryl group" and the "substituted aryl group" listed here are only examples, and the "substituted aryl group" described in this specification also includes groups in which the hydrogen atom bonded to the carbon atom of the aryl group itself in the "substituted aryl group" in the following specific example group G1B has been further replaced by a substituent, and groups in which the hydrogen atom of the substituent in the "substituted aryl group" in the following specific example group G1B has been further replaced by a substituent.

[0056] · Unsubstituted aryl group (specific example group G1A):

[0057] Phenyl,

[0058] p - Biphenylyl,

[0059] m - Biphenylyl,

[0060] o - Biphenylyl,

[0061] 4 - p - Terphenyl - yl,

[0062] 3 - p - Terphenyl - yl,

[0063] 2 - p - Terphenyl - yl,

[0064] 4 - m - Terphenyl - yl,

[0065] 3 - m - Terphenyl - yl,

[0066] 2 - m - Terphenyl - yl,

[0067] o - terphenyl - 4 - yl,

[0068] o - terphenyl - 3 - yl,

[0069] o - terphenyl - 2 - yl,

[0070] 1 - naphthyl,

[0071] 2 - naphthyl,

[0072] anthryl,

[0073] benzanthryl,

[0074] phenanthryl,

[0075] benzophenanthryl, phenalenyl,

[0076] pyrenyl,

[0077] - yl,

[0078] benzopyrenyl,

[0079] triphenylenyl,

[0080] benzotriphenylenyl,

[0081] tetraphenylenyl,

[0082] pentaphenylenyl,

[0083] fluorenyl,

[0084] 9,9’ - spirobifluorenyl,

[0085] benzofluorenyl,

[0086] dibenzofluorenyl,

[0087] fluoranthenyl,

[0088] benzofluoranthenyl,

[0089] perylenyl, and

[0090] 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).

[0091] [Chemical formula 2]

[0092]

[0093] [Chemical formula 3]

[0094]

[0095] · Substituted aryl group (specific example group G1B):

[0096] o-Tolyl,

[0097] m-Tolyl,

[0098] p-Tolyl,

[0099] p-Xylyl,

[0100] m-Xylyl,

[0101] o-Xylyl,

[0102] p-Isopropylphenyl,

[0103] m-Isopropylphenyl,

[0104] o-Isopropylphenyl,

[0105] p-tert-Butylphenyl,

[0106] m-tert-Butylphenyl,

[0107] o-tert-Butylphenyl,

[0108] 3,4,5-Trimethylphenyl,

[0109] 9,9-Dimethylfluorenyl,

[0110] 9,9-Diphenylfluorenyl

[0111] 9,9-Bis(4-methylphenyl)fluorenyl,

[0112] 9,9-Bis(4-isopropylphenyl)fluorenyl,

[0113] 9,9-Bis(4-tert-butylphenyl)fluorenyl,

[0114] Cyano-phenyl,

[0115] Triphenylsilylphenyl,

[0116] Trimethylsilylphenyl,

[0117] Phenylnaphthyl,

[0118] Naphthylphenyl, and

[0119] 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.

[0120] · "substituted or unsubstituted heterocyclic group"

[0121] The "heterocyclic group" described in this specification is a cyclic group containing at least 1 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. The "heterocyclic group" described in this specification is a monocyclic group or a polycyclic group.

[0122] The "heterocyclic group" described in this specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0123] 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".

[0124] The "substituted heterocyclic group" means 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. 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" in 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" in specific example group G2B have been further replaced by substituents.

[0125] 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).

[0126] 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 a monovalent heterocyclic group derived from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) are replaced with substituents (specific example group G2B4).

[0127] · Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1):

[0128] Pyrrolyl,

[0129] Imidazolyl,

[0130] Pyrazolyl,

[0131] Triazolyl,

[0132] Tetrazolyl,

[0133] Oxazolyl,

[0134] Isoxazolyl,

[0135] Oxadiazolyl,

[0136] Thiazolyl,

[0137] Isothiazolyl,

[0138] Thiadiazolyl,

[0139] Pyridyl,

[0140] Pyridazinyl,

[0141] Pyrimidinyl,

[0142] Pyrazinyl,

[0143] Triazinyl,

[0144] Indolyl,

[0145] Isoindolyl,

[0146] Indazolyl, quinazolinyl,

[0147] Quinolyl,

[0148] Isoquinolyl,

[0149] Cinnolinyl,

[0150] Phthalazinyl,

[0151] Quinazolinyl,

[0152] Quinoxalinyl,

[0153] Benzimidazolyl,

[0154] Indazolyl,

[0155] Phenanthrolinyl,

[0156] Phenidinyl,

[0157] Acridinyl,

[0158] Phenazinyl,

[0159] Carbazoyl,

[0160] Benzo[h]carbazolyl,

[0161] Morpholinyl,

[0162] Phenoxazinyl,

[0163] Phenothiazinyl,

[0164] Aza-carbazolyl, and diaza-carbazolyl.

[0165] · Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2):

[0166] Furyl,

[0167] Oxazolyl,

[0168] Isoxazolyl,

[0169] Oxadiazolyl,

[0170] Xanthenyl,

[0171] Benzofuryl,

[0172] Isobenzofuryl,

[0173] Dibenzofuryl,

[0174] Naphtho[2,3-b]benzofuryl,

[0175] Benzoxazolyl,

[0176] Benzisoxazolyl,

[0177] Phenoxazinyl,

[0178] Morpholinyl,

[0179] Dinaphtho[2,3-b:2',3'-d]furyl,

[0180] Aza-dibenzofuryl,

[0181] Diaza-dibenzofuryl,

[0182] Aza-naphtho[2,3-b]benzofuryl, and

[0183] Diaza-naphtho[2,3-b]benzofuryl.

[0184] · Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3):

[0185] Thienyl,

[0186] Thiazolyl,

[0187] Isothiazolyl,

[0188] Thiadiazolyl,

[0189] Benzothienyl,

[0190] Isobenzothienyl,

[0191] Dibenzothienyl,

[0192] Naphthobenzothienyl,

[0193] Benzothiazolyl, benzisothiazolyl,

[0194] Phenothiazinyl,

[0195] Dinaphthothienyl,

[0196] Azadibenzothienyl,

[0197] Diazadibenzothienyl,

[0198] Azanaphthobenzothienyl, and

[0199] Diazanaphthobenzothienyl.

[0200] · 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):

[0201] [Chemical formula 4]

[0202]

[0203] [Chemical formula 5]

[0204]

[0205] In the above general formulas (TEMP-16) to (TEMP-33), XA and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH 2 . Among them, X A and Y A at least one of them is an oxygen atom, a sulfur atom, or NH.

[0206] In the above general formulas (TEMP-16) to (TEMP-33), when at least any one of X A and Y A is NH or CH 2 , 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 .

[0207] · Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1):

[0208] (9-Phenyl)carbazolyl,

[0209] (9-Biphenyl)carbazolyl,

[0210] (9-Phenyl)phenylcarbazolyl,

[0211] (9-Naphthyl)carbazolyl,

[0212] Diphenylcarbazol-9-yl,

[0213] Phenylcarbazol-9-yl,

[0214] Methylbenzimidazolyl,

[0215] Ethylbenzimidazolyl,

[0216] Phenyltriazinyl,

[0217] Biphenyltriazinyl,

[0218] Diphenyltriazinyl,

[0219] Phenylquinazolinyl, and biphenylquinazolinyl.

[0220] · Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2):

[0221] Phenyldibenzofuranyl,

[0222] Methyldibenzofuranyl,

[0223] tert-Butyldibenzofuranyl, and

[0224] The monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0225] · Substituted heterocyclic groups containing a sulfur atom (specific example group G2B3):

[0226] Phenyldibenzothienyl,

[0227] Methyldibenzothienyl,

[0228] tert-Butyldibenzothienyl, and

[0229] The monovalent residue of spiro[9H-thioxanthene-9,9’-[9H]fluorene].

[0230] · A group in which one or more hydrogen atoms of the monovalent heterocyclic group derived from the ring structures represented by the above general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific example group G2B4).

[0231] The above-mentioned "one or more hydrogen atoms of the monovalent heterocyclic group" refers to one or more hydrogen atoms selected from the hydrogen atoms bonded to the ring-forming carbon atoms of the monovalent heterocyclic group, the hydrogen atoms bonded to the nitrogen atoms when at least one of XA and YA is NH, and the hydrogen atoms of the methylene group when one of XA and YA is CH2.

[0232] · "Substituted or unsubstituted alkyl"

[0233] As specific examples of the "substituted or unsubstituted alkyl" described in this specification (specific example group G3), 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 "unsubstituted alkyl", and the substituted alkyl refers to the case where the "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when only expressed as "alkyl", it includes both "unsubstituted alkyl" and "substituted alkyl".

[0234] "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 both linear "unsubstituted alkyl" and branched "unsubstituted alkyl". 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.

[0235] · Unsubstituted alkyl (specific example group G3A):

[0236] Methyl,

[0237] Ethyl,

[0238] n-Propyl,

[0239] Isopropyl,

[0240] n-Butyl,

[0241] Isobutyl,

[0242] sec-Butyl, and

[0243] tert-Butyl.

[0244] · Substituted alkyl (specific example group G3B):

[0245] Heptafluoropropyl (including isomers),

[0246] Pentafluoroethyl,

[0247] 2,2,2-Trifluoroethyl, and

[0248] Trifluoromethyl.

[0249] · "Substituted or unsubstituted alkenyl"

[0250] As a specific example (specific example group G4) of the "substituted or unsubstituted alkenyl" described in this specification, the following unsubstituted alkenyl (specific example group G4A) and substituted alkenyl (specific example group G4B) etc. can be cited. (Here, the unsubstituted alkenyl means the case where the "substituted or unsubstituted alkenyl" is an "unsubstituted alkenyl", and the "substituted alkenyl" means the case where the "substituted or unsubstituted alkenyl" is a "substituted alkenyl".) In this specification, when only "alkenyl" is expressed, both "unsubstituted alkenyl" and "substituted alkenyl" are included.

[0251] 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 such as groups in which the following "unsubstituted alkenyl" (specific example group G4A) has substituents and substituted alkenyl (specific example group G4B) can be cited. 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 a group in which a hydrogen atom of the alkenyl itself in the "substituted alkenyl" of specific example group G4B is further replaced by a substituent and a group in which a hydrogen atom of the substituent in the "substituted alkenyl" of specific example group G4B is further replaced by a substituent.

[0252] · Unsubstituted alkenyl (specific example group G4A):

[0253] Vinyl,

[0254] Allyl,

[0255] 1-Butenyl,

[0256] 2-Butenyl, and

[0257] 3-Butenyl.

[0258] · Substituted alkenyl (specific example group G4B):

[0259] 1,3-Butadienyl,

[0260] 1-Methylvinyl,

[0261] 1-Methylallyl,

[0262] 1,1-Dimethylallyl,

[0263] 2-Methylallyl, and

[0264] 1,2-Dimethylallyl.

[0265] · "Substituted or unsubstituted alkynyl"

[0266] 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 referred to as "alkynyl" hereinafter, it includes both "unsubstituted alkynyl" and "substituted alkynyl".

[0267] "Substituted alkynyl" means a group in which one or more hydrogen atoms in the "unsubstituted alkynyl" are replaced by substituents. As specific examples of the "substituted alkynyl", groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl" (specific example group G5A) are replaced by substituents etc. can be cited.

[0268] · Unsubstituted alkynyl (specific example group G5A):

[0269] Ethynyl

[0270] · "Substituted or unsubstituted cycloalkyl"

[0271] As specific examples (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 referred to as "cycloalkyl", it includes both "unsubstituted cycloalkyl" and "substituted cycloalkyl".

[0272] "Substituted cycloalkyl" means a group in which one or more hydrogen atoms in the "unsubstituted cycloalkyl" are replaced by substituents. As specific examples of the "substituted cycloalkyl", groups in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl" (specific example group G6A) are replaced by substituents and examples of 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 groups in which one or more hydrogen atoms bonded to the carbon atoms of the cycloalkyl itself in the "substituted cycloalkyl" of specific example group G6B are replaced by substituents and groups in which the hydrogen atoms of the substituents in the "substituted cycloalkyl" of specific example group G6B are further replaced by substituents.

[0273] · Unsubstituted cycloalkyl (specific example group G6A):

[0274] Cyclopropyl,

[0275] Cyclobutyl,

[0276] Cyclopentyl,

[0277] Cyclohexyl,

[0278] 1 - Adamantyl,

[0279] 2 - Adamantyl,

[0280] 1 - Norbornyl, and

[0281] 2 - Norbornyl.

[0282] · Substituted cycloalkyl (specific example group G6B):

[0283] 4 - Methylcyclohexyl.

[0284] · "A group represented by -Si(R 901 )(R 902 )(R 903 )"

[0285] 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

[0286] -Si(G1)(G1)(G1),

[0287] -Si(G1)(G2)(G2),

[0288] -Si(G1)(G1)(G2),

[0289] -Si(G2)(G2)(G2),

[0290] -Si(G3)(G3)(G3), and

[0291] -Si(G6)(G6)(G6). Here,

[0292] G1 is "substituted or unsubstituted aryl" described in specific example group G1.

[0293] G2 is "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0294] G3 is "substituted or unsubstituted alkyl" described in specific example group G3.

[0295] G6 is "substituted or unsubstituted cycloalkyl" described in specific example group G6. The plurality of G1s in -Si(G1)(G1)(G1) are the same as or different from each other.

[0296] - The multiple G2s in -Si(G1)(G2)(G2) are the same as or different from each other.

[0297] - The multiple G1s in -Si(G1)(G1)(G2) are the same as or different from each other.

[0298] - The multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other.

[0299] - The multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other.

[0300] - The multiple G6s in -Si(G6)(G6)(G6) are the same as or different from each other.

[0301] · "The group represented by -O-(R 904 )"

[0302] As specific examples (specific example group G8) of the group represented by -O-(R 904 ) described in this specification, there can be cited

[0303] -O(G1),

[0304] -O(G2),

[0305] -O(G3), and

[0306] -O(G6).

[0307] Here,

[0308] G1 is the "substituted or unsubstituted aryl" described in specific example group G1.

[0309] G2 is the "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0310] G3 is the "substituted or unsubstituted alkyl" described in specific example group G3.

[0311] G6 is the "substituted or unsubstituted cycloalkyl" described in specific example group G6.

[0312] · "The group represented by -S-(R 905 )"

[0313] As specific examples (specific example group G9) of the group represented by -S-(R 905 ) described in this specification, there can be cited

[0314] -S(G1),

[0315] -S(G2),

[0316] -S(G3), and

[0317] -S(G6).

[0318] Here,

[0319] G1 is the "substituted or unsubstituted aryl" described in Specific Example Group G1.

[0320] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0321] G3 is the "substituted or unsubstituted alkyl" described in Specific Example Group G3.

[0322] G6 is the "substituted or unsubstituted cycloalkyl" described in Specific Example Group G6.

[0323] · The group represented by "-N(R 906 )(R 907 )"

[0324] 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

[0325] -N(G1)(G1),

[0326] -N(G2)(G2),

[0327] -N(G1)(G2),

[0328] -N(G3)(G3), and

[0329] -N(G6)(G6). Here,

[0330] G1 is the "substituted or unsubstituted aryl" described in Specific Example Group G1.

[0331] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0332] G3 is the "substituted or unsubstituted alkyl" described in Specific Example Group G3.

[0333] G6 is the "substituted or unsubstituted cycloalkyl" described in Specific Example Group G6.

[0334] The multiple G1s in -N(G1)(G1) are the same as or different from each other.

[0335] The multiple G2s in -N(G2)(G2) are the same as or different from each other.

[0336] The multiple G3s in -N(G3)(G3) are the same as or different from each other.

[0337] The multiple G6s in -N(G6)(G6) are the same as or different from each other.

[0338] · "Halogen atom"

[0339] 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.

[0340] · "Substituted or unsubstituted fluoroalkyl"

[0341] 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" has been 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" have been 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" have been 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" have been further replaced by substituents and a group in which one or more hydrogen atoms of the substituents in the "substituted fluoroalkyl" have been 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) have been replaced by fluorine atoms can be cited.

[0342] · "Substituted or unsubstituted haloalkyl"

[0343] 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, 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.

[0344] · "substituted or unsubstituted alkoxy"

[0345] 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, more preferably 1 to 18, unless otherwise specified in this specification.

[0346] · "substituted or unsubstituted alkylthio"

[0347] 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, more preferably 1 to 18, unless otherwise specified in this specification.

[0348] · "substituted or unsubstituted aryloxy"

[0349] 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, more preferably 6 to 18, unless otherwise specified in this specification.

[0350] · "substituted or unsubstituted arylthio"

[0351] 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.

[0352] · "Substituted or unsubstituted trialkylsilyl"

[0353] As a specific example of the "trialkylsilyl group" 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 group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.

[0354] · "Substituted or unsubstituted aralkyl"

[0355] 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.

[0356] As specific examples of the "substituted or unsubstituted aralkyl", there can be mentioned 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, etc.

[0357] In this specification, 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, chrysenyl, triphenylenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl, etc.

[0358] In this specification, 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.

[0359] In this specification, unless otherwise specified in this specification, the carbazolyl group is specifically any one of the following groups.

[0360] [Chemical formula 6]

[0361]

[0362] In this specification, unless otherwise specified in this specification, the (9-phenyl)carbazolyl group is specifically any one of the following groups.

[0363] [Chemical formula 7]

[0364]

[0365] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents the bonding position.

[0366] In this specification, unless otherwise specified in this specification, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any one of the following groups.

[0367] [Chemical Formula 8]

[0368]

[0369] In the above general formulas (TEMP-34) to (TEMP-41), * represents the bonding position.

[0370] Unless otherwise specified in this specification, the substituted or unsubstituted alkyl groups are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.

[0371] · "Substituted or unsubstituted arylene"

[0372] Unless otherwise specified in this specification, the "substituted or unsubstituted arylene" described in this specification is a divalent group derived by removing one hydrogen atom from the aryl 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 aryl ring of the "substituted or unsubstituted aryl" described in specific example group G1 can be cited, etc.

[0373] · "Substituted or unsubstituted divalent heterocyclic group"

[0374] Unless otherwise specified in this specification, the "substituted or unsubstituted divalent heterocyclic group" described in this specification 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.

[0375] · "Substituted or unsubstituted alkylene"

[0376] Unless otherwise specified in this specification, the "substituted or unsubstituted alkylene" described in this specification 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.

[0377] Unless otherwise specified in this specification, the substituted or unsubstituted arylene is preferably any one of the following general formulas (TEMP-42) to (TEMP-68).

[0378] [Chemical Formula 9]

[0379]

[0380] [Chemical Formula 10]

[0381]

[0382] In the above general formulas (TEMP-42) to (TEMP-52), Q 1 to Q 10 are each independently a hydrogen atom or a substituent.

[0383] In the above general formulas (TEMP-42) to (TEMP-52), * represents the bonding position.

[0384] [Chemical Formula 11]

[0385]

[0386] In the above general formulas (TEMP-53) to (TEMP-62), Q 1 to Q 10 are each independently a hydrogen atom or a substituent.

[0387] The group Q 9 and Q 10 can be bonded to each other via a single bond to form a ring.

[0388] In the above general formulas (TEMP-53) to (TEMP-62), * represents the bonding position.

[0389] [Chemical Formula 12]

[0390]

[0391] In the above general formulas (TEMP-63) to (TEMP-68), Q 1 to Q 8 are each independently a hydrogen atom or a substituent.

[0392] In the above general formulas (TEMP-63) to (TEMP-68), * represents the bonding position.

[0393] 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).

[0394] [Chemical Formula 13]

[0395]

[0396] [Chemical Formula 14]

[0397]

[0398] [Chemical Formula 15]

[0399]

[0400] In the above general formulas (TEMP-69) to (TEMP-82), Q 1 to Q 9 are each independently a hydrogen atom or a substituent.

[0401] [Chemical Formula 16]

[0402]

[0403] [Chemical Formula 17]

[0404]

[0405] [Chemical Formula 18]

[0406]

[0407] [Chemical Formula 19]

[0408]

[0409] In the above general formulas (TEMP-83) to (TEMP-102), Q 1 to Q 8 are each independently a hydrogen atom or a substituent.

[0410] The above is the description of "substituents described in this specification".

[0411] · "Case of bonding to form a ring"

[0412] In this specification, the case where "one or more of the groups composed of two or more adjacent ones 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 where "one or more of the groups composed of two or more adjacent ones bond to each other to form a substituted or unsubstituted monocyclic ring", the case where "one or more of the groups composed of two or more adjacent ones bond to each other to form a substituted or unsubstituted fused ring", and the case where "one or more of the groups composed of two or more adjacent ones do not bond to each other".

[0413] Hereinafter, the case where "one or more of the groups composed of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more of the groups composed of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted fused ring" in this specification (hereinafter, these cases may be 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.

[0414] [Chemical formula 20]

[0415]

[0416] For example, in the case of "one or more of the groups composed of two or more adjacent groups are bonded to each other to form a ring" among R 921 ~R 930 , the group composed of two adjacent groups as 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 , and the group of R 929 and R 921 .

[0417] The above "one or more" means that two or more of the groups composed of two or more adjacent groups can form rings simultaneously. For example, when R 921 and R 922 are bonded to each other to form ring Q A and at the same time R 925 and R 926 are bonded 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).

[0418] [Chemical formula 21]

[0419]

[0420] 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 is bonded as in the aforementioned example, but also the case where a group consisting of "three or more" adjacent members is bonded. For example, it means that R 921 is bonded to R 922 to form ring Q A , and R 922 is bonded to R 923 to form ring Q C . A case where a group consisting of three mutually adjacent members (R 921 , R 922 and R 923 ) is bonded to 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 .

[0421] [Chemical formula 22]

[0422]

[0423] In the "monocyclic ring" or "fused ring" formed, as the structure of only the formed ring, it can be a saturated ring or an unsaturated ring. Even when "one group in the group consisting of two adjacent members" forms a "monocyclic ring" or "fused ring", the "monocyclic ring" 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 ring" or "fused ring". In addition, the formed ring Q A and ring Q C in the above general formula (TEMP-105) are "fused rings". The ring Q A of the above general formula (TEMP-105) and ring Q C form a fused ring by the fusion of ring Q A and ring Q C . If the ring Q A in the above general formula (TMEP-104) is a benzene ring, then ring Q A is a monocyclic ring. If the ring Q A in the above general formula (TMEP-104) is a naphthalene ring, then ring Q A is a fused ring.

[0424] "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.

[0425] 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 terminated with a hydrogen atom can be cited.

[0426] 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 terminated with a hydrogen atom can be cited.

[0427] 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 terminated with a hydrogen atom can be cited.

[0428] "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 bonded to each other to form a ring Q A means a ring 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 R 921 and R 922 form a ring Q A , among the cases 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.

[0429] Herein, 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 optional element (for example, in the case of a carbon element or a nitrogen element), the bond that does not form a ring can be terminated 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.

[0430] 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.

[0431] Unless otherwise specified in this specification, among the "single ring" and the "fused ring", the "single ring" is preferred.

[0432] Unless otherwise specified in this specification, among the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred.

[0433] In this specification, unless otherwise specified, the "monocyclic ring" is preferably a benzene ring.

[0434] In this specification, unless otherwise specified, the "unsaturated ring" is preferably a benzene ring.

[0435] In the case of "one or more groups among two or more adjacent groups" "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 two or more adjacent groups bonded to each other to form a substituted or unsubstituted "unsaturated ring" formed by a plurality of atoms of the parent 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 atoms.

[0436] 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.

[0437] 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.

[0438] The above is the description of the case of "one or more groups among two or more adjacent groups bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case of "one or more groups among two or more adjacent groups bonded to each other to form a substituted or unsubstituted fused ring" (the case of "bonded to form a ring").

[0439] · Substituents when expressed as "substituted or unsubstituted"

[0440] In one embodiment of this specification, the substituents when expressed as "substituted or unsubstituted" (in this specification, sometimes referred to as "optional substituents") are, for example, selected from

[0441] unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0442] unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0443] unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0444] unsubstituted cycloalkyl groups having 3 to 50 ring carbon atoms,

[0445] -Si(R 901)(R 902 )(R 903 ),

[0446] -O-(R 904 ),

[0447] -S-(R 905 ),

[0448] -N(R 906 )(R 907 ),

[0449] a halogen atom, a cyano group, a nitro group,

[0450] an unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0451] an unsubstituted heterocyclic group having 5 to 50 ring atoms

[0452] and the like,

[0453] Here, R 901 to R 907 are each independently

[0454] a hydrogen atom,

[0455] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0456] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0457] 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.

[0458] 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,

[0459] 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,

[0460] 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,

[0461] 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,

[0462] When there are two or more R 905 s, the two or more R 905 s may be the same or different from each other,

[0463] In the case of R 906 When there are two or more, two or more Rs 906 are the same as or different from each other,

[0464] In the case of R 907 When there are two or more, two or more Rs 907 are the same as or different from each other.

[0465] In one embodiment, when the above expression is "substituted or unsubstituted", the substituents are selected from the group consisting of

[0466] alkyl groups having 1 to 50 carbon atoms,

[0467] aryl groups having 6 to 50 ring carbon atoms, and

[0468] heterocyclic groups having 5 to 50 ring atoms

[0469] groups in the group.

[0470] In one embodiment, when the above expression is "substituted or unsubstituted", the substituents are selected from the group consisting of

[0471] alkyl groups having 1 to 18 carbon atoms,

[0472] aryl groups having 6 to 18 ring carbon atoms, and

[0473] heterocyclic groups having 5 to 18 ring atoms

[0474] groups in the group.

[0475] Specific examples of each of the above optional substituents are the specific examples of the substituents described in the item of "substituents described in this specification" above.

[0476] 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.

[0477] In this specification, unless otherwise noted, the optional substituents may further have substituents. The substituents further possessed by the optional substituents are the same as the above optional substituents.

[0478] In this specification, the numerical range expressed 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.

[0479] Hereinafter, the compounds of the present invention will be described.

[0480] The compounds of the present invention are represented by the following formula (1). Hereinafter, the compounds of the present invention represented by formula (1) and the various formulas described later may sometimes be referred to simply as "invention compounds".

[0481] [Chemical formula 23]

[0482]

[0483] Hereinafter, the reference numerals in formula (1) and the various formulas described later will be explained. It should be noted that in the following formulas representing the invention compounds, the same reference numerals have the same meanings.

[0484] R 1 ~R 10 Each independently represents a hydrogen atom, a fluorine atom, a cyano group, 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, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms. Preferably, it is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. More preferably, it is a hydrogen atom.

[0485] R 1 ~R 10 may all be hydrogen atoms.

[0486] R 1 ~R 10 The details of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms represented are the same as those described in "Substituents Described in this Specification".

[0487] The above-mentioned unsubstituted aryl group is preferably phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, phenalenyl, pyrenyl, chrysenyl, triphenylenyl, tetraphenylenyl, pentaphenylenyl, fluorenyl, fluoranthenyl, or perylenyl. More preferably, it is phenyl, biphenyl, terphenyl, naphthyl, or phenanthryl. Further preferably, it is phenyl, biphenyl, or naphthyl. Particularly preferably, it is phenyl.

[0488] The above-mentioned substituted aryl group is preferably 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, or 9,9'-spirobifluorenyl.

[0489] R 1 ~R 10 The details of the substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms represented are the same as those described in "Substituents Described in this Specification".

[0490] The above unsubstituted heterocyclic group is preferably pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, phenanthrolinyl, carbazolyl, benzocarbazolyl, dibenzofuranyl, naphthobenzofuranyl, dibenzothiophenyl, or naphthobenzothiophenyl, more preferably pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, naphthobenzofuranyl, or dibenzothiophenyl, and still more preferably pyridyl, carbazolyl, dibenzofuranyl, naphthobenzofuranyl, or dibenzothiophenyl.

[0491] The above substituted heterocyclic group is preferably 9-phenylcarbazolyl, diphenylcarbazol-9-yl, or phenylcarbazol-9-yl.

[0492] R 1 ~R 10 The details of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms represented by are the same as those described in "Substituents Described in This Specification".

[0493] The above unsubstituted alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, or n-pentyl, more preferably methyl, ethyl, isopropyl, or tert-butyl, and still more preferably methyl or tert-butyl.

[0494] R 1 ~R 10 The details of the substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms represented by are the same as those described in "Substituents Described in This Specification".

[0495] The above unsubstituted cycloalkyl group is preferably cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, or norbornyl.

[0496] At least one group of two adjacent groups selected from R 1 ~R 10 , that is, two adjacent groups selected from R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , and R 9 and R 10 may be bonded to each other to form a substituted or unsubstituted ring structure, or may not be bonded to each other and thus do not form a substituted or unsubstituted ring structure.

[0497] The above-mentioned substituted or unsubstituted ring structures are, for example, selected from substituted or unsubstituted aromatic hydrocarbon rings, substituted or unsubstituted aliphatic hydrocarbon rings, substituted or unsubstituted aromatic heterocyclic rings, and substituted or unsubstituted aliphatic heterocyclic rings.

[0498] The above-mentioned aromatic hydrocarbon rings are, for example, benzene ring, biphenylene ring, naphthalene ring, anthracene ring, benzanthracene ring, phenanthrene ring, benzophenanthrene ring, phenalene ring, pyrene ring, chrysene ring, 1,1-dimethylindene ring, or triphenylene ring, preferably benzene ring or naphthalene ring, more preferably benzene ring.

[0499] The above-mentioned aliphatic hydrocarbon rings are, for example, cyclopentene ring, cyclopentadiene ring, cyclohexene ring, cyclohexadiene ring, or aliphatic hydrocarbon rings obtained by partial hydrogenation of the above-mentioned aromatic hydrocarbon rings.

[0500] The above-mentioned aromatic heterocyclic rings are, for example, pyrrole ring, furan ring, thiophene ring, pyridine ring, imidazole ring, pyrazole ring, indole ring, isoindole ring, benzofuran ring, isobenzofuran ring, benzothiophene ring, benzimidazole ring, indazole ring, dibenzofuran ring, naphthobenzofuran ring, dibenzothiophene ring, naphthobenzothiophene ring, carbazole ring, or benzocarbazole ring.

[0501] The above-mentioned aliphatic heterocyclic rings are, for example, aliphatic heterocyclic rings obtained by partial hydrogenation of the above-mentioned aromatic heterocyclic rings.

[0502] In one aspect of the present invention, preferably, a benzene ring is formed by bonding two adjacent ones selected from a group consisting of R 2 and R 3 , R 3 and R 4 , R 7 and R 8 , and R 8 and R 9 to each other.

[0503] In one aspect of the present invention, the diphenyltriazinyl structure represented by the following formula of the inventive compound is represented by the following formula (4) or (5).

[0504] [Chemical formula 24]

[0505]

[0506] [Chemical formula 25]

[0507]

[0508] In formula (4), R 2 to R 4 and R 7 to R 9 are the same as the definitions in formula (1).

[0509] Among them, R2 ~R 4 and R 7 ~R 9 At least one of them is a fluorine atom, a cyano group, 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, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.

[0510] The details of each group are the same as those described above for R 1 ~R 10 as described.

[0511] Selected from R 2 and R 3 , R 3 and R 4 , R 7 and R 8 , and R 8 and R 9 At least two adjacent ones of the groups can bond to each other to form a substituted or unsubstituted ring structure, or they can not bond to each other and do not form a substituted or unsubstituted ring structure.

[0512] The details of the substituted or unsubstituted ring structure are as described above.

[0513] In formula (5), R 3 and R 8 are defined the same as in formula (1).

[0514] Among them, at least one of R 3 and R 8 is a fluorine atom, a cyano group, 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, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.

[0515] The details of each group are the same as those described above for R 1 ~R 10 as described.

[0516] Therefore, the inventive compound represented by formula (1) includes the compound represented by the following formula (6) or (7).

[0517] [Chemical formula 26]

[0518]

[0519] In each formula representing the inventive compound,

[0520] R 11 ~R 14Each is independently a hydrogen atom, a fluorine atom, a cyano group, 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, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, more preferably a hydrogen atom.

[0521] Details of each group are the same as those described above for R 1 ~R 10 .

[0522] R 11 ~R 14 may all be hydrogen atoms.

[0523] Selected from R 11 ~R 14 , at least two adjacent ones, that is, selected from R 11 and R 12 , R 12 and R 13 , and R 13 and R 14 may be bonded to each other to form a substituted or unsubstituted ring structure, or may not be bonded to each other to not form a substituted or unsubstituted ring structure.

[0524] Details of the substituted or unsubstituted ring structure are as described above.

[0525] In each formula representing the inventive compound, Ar is a substituted or unsubstituted non-fused aryl group having 6 to 50 ring carbon atoms, preferably 6 to 30, more preferably 6 to 18, or a substituted or unsubstituted fused aryl group having 10 to 16 ring carbon atoms.

[0526] The above-mentioned unsubstituted non-fused aryl group is preferably phenyl, biphenyl, or terphenyl, preferably phenyl or biphenyl.

[0527] The above-mentioned biphenyl is selected from o-biphenyl, m-biphenyl, and p-biphenyl.

[0528] The above-mentioned terphenyl is preferably selected from the following formulae.

[0529] [Chemical formula 27]

[0530]

[0531] The above-mentioned unsubstituted fused aryl group is naphthyl, anthryl, phenanthryl, or fluoranthenyl.

[0532] The above-mentioned naphthyl is 1-naphthyl or 2-naphthyl.

[0533] The above-mentioned anthryl group is preferably 9-anthryl group.

[0534] The above-mentioned phenanthryl group is preferably 2-phenanthryl group or 9-phenanthryl group.

[0535] The above-mentioned fluoranthenyl group is preferably 3-fluoranthenyl group.

[0536] The above-mentioned substituted fused aryl group is preferably 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9'-spirobifluorenyl group, or phenylnaphthyl group.

[0537] The above-mentioned 9,9-dimethylfluorenyl group is preferably 9,9-dimethylfluoren-1-yl group, 9,9-dimethylfluoren-2-yl group, 9,9-dimethylfluoren-3-yl group, or 9,9-dimethylfluoren-4-yl group, more preferably 9,9-dimethylfluoren-2-yl group or 9,9-dimethylfluoren-4-yl group, and further preferably 9,9-dimethylfluoren-2-yl group.

[0538] The above-mentioned 9,9-diphenylfluorenyl group is preferably 9,9-diphenylfluoren-1-yl group, 9,9-diphenylfluoren-2-yl group, 9,9-diphenylfluoren-3-yl group, or 9,9-diphenylfluoren-4-yl group, more preferably 9,9-diphenylfluoren-2-yl group or 9,9-diphenylfluoren-4-yl group, and further preferably 9,9-diphenylfluoren-2-yl group.

[0539] The above-mentioned 9,9'-spirobifluorenyl group is preferably 9,9'-spirobifluoren-1-yl group, 9,9'-spirobifluoren-2-yl group, 9,9'-spirobifluoren-3-yl group, or 9,9'-spirobifluoren-4-yl group, more preferably 9,9'-spirobifluoren-2-yl group or 9,9'-spirobifluoren-4-yl group, and further preferably 9,9'-spirobifluoren-2-yl group.

[0540] The above-mentioned phenylnaphthyl group is preferably 4-phenylnaphth-1-yl group or 6-phenylnaphth-2-yl group.

[0541] In the formulas representing the inventive compounds, L is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and containing only six-membered rings.

[0542] The substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and containing only six-membered rings represented by L is selected from the arylene groups containing only six-membered rings described in "the substituents described in this specification".

[0543] The unsubstituted arylene group containing only six-membered rings is preferably phenylene group, biphenylene group, terphenylene group, naphthylene group, anthrylene group, phenanthrylene group, pyrenylene group, chrysenylene group, or tritophenylene group.

[0544] L is more preferably a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted anthrylene group, and further preferably a substituted or unsubstituted naphthylene group or a substituted or unsubstituted anthrylene group.

[0545] Therefore, the inventive compound comprises a compound represented by the following formula (2) or (3).

[0546] [Chemical formula 28]

[0547]

[0548] [Chemical formula 29]

[0549]

[0550] In formula (2), R 1 ~R 10 , R 11 ~R 14 and Ar are the same as defined in formula (1),

[0551] R 21 ~R 28 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.

[0552] Among them, one selected from R 21 ~R 28 is a single bond bonded to *a, and one selected from R 21 ~R 28 that is not a single bond bonded to *a is a single bond bonded to *b.

[0553] The details of the above groups are the same as the description for R 1 ~R 10 in the above text.

[0554] Two adjacent ones selected from R 21 ~R 28 that are not a single bond bonded to *a and also not a single bond bonded to *b preferably do not bond to each other and thus do not form a ring structure.

[0555] R 21 ~R 28 that are not a single bond bonded to *a and also not a single bond bonded to *b may all be hydrogen atoms.

[0556] In formula (3), R 1 ~R 10 , R 11 ~R 14 and Ar are the same as defined in formula (1),

[0557] R 31 ~R 40Each independently is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.

[0558] Among them, one selected from R 31 ~R 40 is a single bond bonded to *c, and one selected from R 31 ~R 40 that is not a single bond bonded to *c is a single bond bonded to *d.

[0559] The details of each of the above groups are the same as those described above for R 1 ~R 10 .

[0560] Two adjacent ones selected from R 31 ~R 40 that are not single bonds bonded to *c and are also not single bonds bonded to *d preferably do not bond to each other and thus do not form a ring structure.

[0561] R 31 ~R 40 that are not single bonds bonded to *c and are also not single bonds bonded to *d may all be hydrogen atoms.

[0562] The inventive compound represented by formula (2) preferably contains the compound represented by formula (2a).

[0563] [Chemical formula 30]

[0564]

[0565] The inventive compound represented by formula (3) preferably contains the compound represented by formula (3a).

[0566] [Chemical formula 31]

[0567]

[0568] As described above, the "hydrogen atom" used in this specification includes protium atoms, deuterium atoms, and tritium atoms. Therefore, the inventive compound may contain deuterium atoms of natural origin.

[0569] In addition, by using a compound in which part or all of the hydrogen atoms are deuterium atoms (hereinafter referred to as "deuterated compound") as a starting compound, deuterium atoms can be deliberately introduced into the inventive compound. Therefore, in one aspect of the present invention, the inventive compound contains at least 1 deuterium atom (hereinafter, the inventive compound containing at least 1 deuterium atom is referred to as "deuterated form"). That is, the inventive compound can be a compound represented by formula (1) or a formula as its preferred aspect, and at least 1 of the hydrogen atoms possessed by the inventive compound is a deuterium atom. In the compound represented by formula (1) or a formula as its preferred aspect, the hydrogen atom at any position can be a deuterium atom.

[0570] The deuteration rate of the above-mentioned deuterated form (the ratio of the number of deuterium atoms in the inventive compound to the total number of hydrogen atoms) depends on the deuteration rate of the starting compound used. It is generally difficult to make the deuteration rate of all the starting compounds used 100%, so the deuteration rate of the above-mentioned deuterated form is less than 100%.

[0571] The inventive compound can be a mixture containing a deuterated compound and an undeuterated compound, or a mixture of two or more compounds having different deuteration rates. The deuteration rate of such a mixture (the ratio of the number of deuterium atoms in the inventive compound contained in the mixture to the total number of hydrogen atoms) is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and less than 100%.

[0572] In the above-mentioned deuterated form, at least one of the hydrogen atoms selected from the hydrogen atoms represented by R 1 ~R 10 can be a deuterium atom. The deuteration rate (the ratio of the number of deuterium atoms represented by R 1 ~R 10 to the total number of hydrogen atoms) is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and less than 100%.

[0573] In the above-mentioned deuterated form, at least one of the hydrogen atoms selected from the hydrogen atoms represented by R 11 ~R 16 can be a deuterium atom. The deuteration rate (the ratio of the number of deuterium atoms represented by R 11 ~R 16 to the total number of hydrogen atoms) is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and less than 100%.

[0574] In the above-mentioned deuterated form, at least one of the hydrogen atoms in the arylene group represented by L can be a deuterium atom. The deuteration rate (the ratio of the number of deuterium atoms in the arylene group to the total number of hydrogen atoms) is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and less than 100%.

[0575] In the above deuterated body, at least one hydrogen atom among the hydrogen atoms of the aryl group represented by Ar may be a deuterium atom. The deuteration rate (the ratio of the number of deuterium atoms in the aryl group to the total number of hydrogen atoms) is 1% or more, preferably 3% or more, more preferably 5% or more, still more preferably 10% or more, and less than 100%.

[0576] When each of the above groups has a substituent, the optional substituents indicated by "substituted or unsubstituted" are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.

[0577] Details of each group are the same as those described above for R 1 ~R 10 .

[0578] Those skilled in the art can easily produce the inventive compounds by referring to the following synthesis examples and well-known synthesis methods.

[0579] Specific examples of the inventive compounds are shown below, but are not limited to the exemplified compounds below.

[0580] [Chemical formula 32]

[0581]

[0582] [Chemical formula 33]

[0583]

[0584] [Chemical formula 34]

[0585]

[0586] [Chemical formula 35]

[0587]

[0588] [Chemical formula 36]

[0589]

[0590] [Chemical formula 37]

[0591]

[0592] [Chemical formula 38]

[0593]

[0594] [Chemical formula 39]

[0595]

[0596] [Chemical formula 40]

[0597]

[0598] [Chemical formula 41]

[0599]

[0600] [Chemical formula 42]

[0601]

[0602] [Chemical formula 43]

[0603]

[0604] [Chemical formula 44]

[0605]

[0606] [Chemical formula 45]

[0607]

[0608] [Chemical formula 46]

[0609]

[0610] [Chemical formula 47]

[0611]

[0612] Materials for organic EL devices

[0613] The material for an organic EL device of the present invention contains an inventive compound. The content of the inventive compound in the material for an organic EL device 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 material for an organic EL device of the present invention is useful in the manufacture of organic EL devices.

[0614] Organic EL device

[0615] The organic EL device 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 an inventive compound.

[0616] 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., but are not limited thereto. The inventive compound is preferably used as a material for the electron transport region or the light-emitting layer of a fluorescent or phosphorescent EL element, more preferably as a material for the electron transport region, and further preferably as a material for the electron injection layer, electron transport layer, hole blocking layer, or exciton blocking layer, and still more preferably as a material for the electron injection layer or electron transport layer.

[0617] The organic EL element of the present invention can be a monochromatic light-emitting element of a fluorescent or phosphorescent light-emitting type, or can be a white light-emitting element of a fluorescent / phosphorescent hybrid type, and can be a simple type element having a single light-emitting unit or a tandem type element having a plurality of light-emitting units. 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 emits light by recombination of the injected holes and electrons.

[0618] For example, as a typical element configuration of a simple type organic EL element, the following element configurations can be cited.

[0619] (1) Anode / light-emitting unit / cathode

[0620] In addition, the above light-emitting unit can also be a multi-layer type having a plurality of phosphorescent light-emitting layers and 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.

[0621] (a) (Hole injection layer / ) Hole transport layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0622] (b) (Hole injection layer / ) Hole transport layer / Phosphorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0623] (c) (Hole injection layer / ) Hole transport layer / First fluorescent light-emitting layer / Second fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0624] (d) (Hole injection layer / ) Hole transport layer / First phosphorescent light-emitting layer / Second phosphorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0625] (e) (Hole injection layer / ) Hole transport layer / Phosphorescent light-emitting layer / Spacer layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0626] (f) (Hole injection layer / ) Hole transport layer / First phosphorescent emitting layer / Second phosphorescent emitting layer / Spacer layer / Fluorescent emitting layer / Electron transport layer ( / Electron injection layer)

[0627] (g) (Hole injection layer / ) Hole transport layer / First phosphorescent emitting layer / Spacer layer / Second phosphorescent emitting layer / Spacer layer / Fluorescent emitting layer / Electron transport layer ( / Electron injection layer)

[0628] (h) (Hole injection layer / ) Hole transport layer / Phosphorescent emitting layer / Spacer layer / First fluorescent emitting layer / Second fluorescent emitting layer / Electron transport layer ( / Electron injection layer)

[0629] (i) (Hole injection layer / ) Hole transport layer / Electron blocking layer / Fluorescent emitting layer / Electron transport layer ( / Electron injection layer)

[0630] (j) (Hole injection layer / ) Hole transport layer / Electron blocking layer / Phosphorescent emitting layer / Electron transport layer ( / Electron injection layer)

[0631] (k) (Hole injection layer / ) Hole transport layer / Exciton blocking layer / Fluorescent emitting layer / Electron transport layer ( / Electron injection layer)

[0632] (l) (Hole injection layer / ) Hole transport layer / Exciton blocking layer / Phosphorescent emitting layer / Electron transport layer ( / Electron injection layer)

[0633] (m) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Fluorescent emitting layer / Electron transport layer ( / Electron injection layer)

[0634] (n) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Phosphorescent emitting layer / Electron transport layer ( / Electron injection layer)

[0635] (o) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Fluorescent emitting layer / First electron transport layer / Second electron transport layer ( / Electron injection layer)

[0636] (p) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Phosphorescent emitting layer / First electron transport layer / Second electron transport layer ( / Electron injection layer)

[0637] (q) (Hole injection layer / ) Hole transport layer / Fluorescent emitting layer / Hole blocking layer / Electron transport layer ( / Electron injection layer)

[0638] (r) (Hole injection layer / ) Hole transport layer / Phosphorescent emitting layer / Hole blocking layer / Electron transport layer ( / Electron injection layer)

[0639] (s) (Hole injection layer / ) Hole transport layer / Fluorescent emission layer / Exciton blocking layer / Electron transport layer ( / Electron injection layer)

[0640] (t) (Hole injection layer / ) Hole transport layer / Phosphorescent emission layer / Exciton blocking layer / Electron transport layer ( / Electron injection layer)

[0641] (u) (Hole injection layer / ) Hole transport layer / Electron blocking layer / Phosphorescent emission layer / Hole blocking layer / Electron transport layer ( / Electron injection layer)

[0642] (v) (Hole injection layer / ) Hole transport layer / Electron blocking layer / Fluorescent emission layer / Hole blocking layer / Electron transport layer ( / Electron injection layer)

[0643] Each of the above phosphorescent or fluorescent emission layers may be provided as emission layers that respectively exhibit mutually different emission colors. Specifically, in the above light-emitting unit (f), a layer structure such as (hole injection layer / ) hole transport layer / first phosphorescent emission layer (red emission) / second phosphorescent emission layer (green emission) / spacer layer / fluorescent emission layer (blue emission) / electron transport layer can be cited, etc.

[0644] It should be noted that an electron blocking layer may be appropriately provided between each emission layer and the hole transport layer or the spacer layer. In addition, a hole blocking layer may be appropriately provided between each emission 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 emission layer, thereby increasing the recombination probability of charges in the emission layer and improving the luminous efficiency.

[0645] As a typical element structure of a tandem organic EL element, the following element structures can be cited. (2) Anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode

[0646] Here, as the above first light-emitting unit and second light-emitting unit, for example, they can be independently selected from the above light-emitting units.

[0647] The above intermediate layer is usually also referred to as an intermediate electrode, intermediate conductive layer, charge generation layer, electron extraction layer, connection layer, 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.

[0648] Figure 1It is a schematic diagram showing an example of the structure 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 (such as a hole injection layer, a hole transport layer, etc.) is provided between the light-emitting layer 5 and the anode 3, and an electron transport region 7 (such as an electron injection layer, an electron transport layer, etc.) is provided between the light-emitting layer 5 and the cathode 4. In addition, an electron blocking layer (not shown) can be provided on the anode 3 side of the light-emitting layer 5, and a hole blocking layer (not shown) can be provided on the cathode 4 side of the light-emitting layer 5. Thereby, electrons and holes can be confined in the light-emitting layer 5 to further improve the exciton generation efficiency in the light-emitting layer 5.

[0649] Figure 2 It is a schematic diagram showing another structure 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 hole transport layer 6b, and an electron blocking layer 6c. In addition, the electron transport region disposed between the light-emitting layer 5 and the cathode 4 is formed by a hole blocking layer 7a and an electron transport layer 7b.

[0650] It should be noted that in the present invention, the host combined with a fluorescent dopant (fluorescent light-emitting material) is called a fluorescent host, and the host combined with a phosphorescent dopant 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 the material forming the phosphorescent light-emitting layer containing the phosphorescent dopant, and does not mean that it cannot be used as the material for forming the fluorescent light-emitting layer. The same applies to the fluorescent host.

[0651] Substrate

[0652] 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.

[0653] Anode

[0654] The anode formed on the substrate preferably uses metals, alloys, conductive compounds, and mixtures thereof 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 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.

[0655] 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 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.

[0656] The hole injection layer formed adjacent to the anode is formed of a material that easily injects 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.

[0657] Elements belonging to Group 1 or Group 2 of the periodic table, which are materials with a small work function, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (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.

[0658] Hole injection layer

[0659] The hole injection layer is a layer containing a material with high hole injection properties (hole injection material), and is formed between the anode and the light-emitting layer, or between the hole transport layer and the anode when present.

[0660] As the hole injection material, 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.

[0661] As a hole injection layer material, 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: PCzPCA1), 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. can also be cited as low molecular weight organic compounds.

[0662] 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, high molecular compounds added with acids such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can also be used.

[0663] In addition, acceptor materials such as hexaazatriphenylene (HAT) compounds represented by the following formula (K) are also preferably used.

[0664] [Chemical formula 48]

[0665]

[0666] (In the above formula, R 21 ~R 26 each independently represents a cyano group, -CONH 2 , a carboxyl group, or -COOR 27 (R 27 represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms). In addition, selected from R 21 and R22 and R 23 and R 24 and, as well as R 25 and R 26 Among them, two adjacent ones can be bonded to each other to form a group represented by -CO-O-CO-.)

[0667] As R 27 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, etc. can be cited.

[0668] Hole transport layer

[0669] The hole transport layer is a layer containing a material with high hole transportability (hole transport material), which is formed between the anode and the light-emitting layer, or, if present, between the hole injection layer and the light-emitting layer.

[0670] The hole transport layer can be a single-layer structure or a multi-layer structure. For example, the hole transport layer can be a two-layer structure including a first hole transport layer (anode side) and a second hole transport layer (cathode side). In one aspect of the present invention, the single-layer hole transport layer described above is preferably adjacent to the light-emitting layer, or the hole transport layer closest to the cathode in the multi-layer structure, for example, the second hole transport layer in the two-layer structure described above, is preferably adjacent to the light-emitting layer. In another aspect of the present invention, an electron blocking layer described later can be interposed between the single-layer hole transport layer and the light-emitting layer, or between the hole transport layer closest to the light-emitting layer in the multi-layer structure and the light-emitting layer.

[0671] As the hole transport layer material, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used.

[0672] As the aromatic amine compound, for example, 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) can be cited. The above compounds have a hole mobility of 10 -6 cm 2 / Vs or more.

[0673] As carbazole derivatives, for example, 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) can be cited.

[0674] As anthracene derivatives, for example, 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) can be cited.

[0675] Poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA) and other polymer compounds can also be used.

[0676] Among them, as long as the hole transport property is higher than the electron transport property, compounds other than the above can be used.

[0677] Dopant materials for the light-emitting layer

[0678] The light-emitting layer is a layer containing a highly luminescent material (dopant material), and various materials can be used. For example, fluorescent light-emitting materials and phosphorescent light-emitting materials can be used as dopant materials. Fluorescent light-emitting materials are compounds that emit light using singlet excited states, and phosphorescent light-emitting materials are compounds that emit light using triplet excited states.

[0679] As blue fluorescent light-emitting materials that can be used for the light-emitting layer, pyrene derivatives, styrylamine derivatives, chrysene 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.

[0680] As a green fluorescent luminescent 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.

[0681] As a red fluorescent luminescent 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.

[0682] As a blue phosphorescent luminescent 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.

[0683] 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)), and the like.

[0684] 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.

[0685] 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-trifluoroacetone](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).

[0686] Host material of the light-emitting layer

[0687] The light-emitting layer can be configured to disperse the above dopant material in other materials (host material). 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.

[0688] As the host material, for example, use

[0689] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes,

[0690] (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives,

[0691] (3) Condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives,

[0692] (4) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives.

[0693] For example, metal complexes such as 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. can be used;

[0694] 2-(4-Biphenyl)-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-biphenyl)-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;

[0695] 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-diphenylchrysene, etc. condensed aromatic compounds; and

[0696] N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: CzA1PA), 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.

[0697] In particular, in the case of a blue fluorescent element, the following anthracene compounds are preferably used as host materials.

[0698] [Chemical formula 49]

[0699]

[0700] [Chemical formula 50]

[0701]

[0702] [Chemical formula 51]

[0703]

[0704] Electron transport layer

[0705] The electron transport layer is a layer containing a material with high electron transport properties (electron transport material), formed between the light-emitting layer and the cathode, or formed between the electron injection layer and the light-emitting layer if present.

[0706] The electron transport layer can be a single-layer structure or a multi-layer structure. For example, the electron transport layer can be a two-layer structure including a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one aspect of the present invention, the single-layer electron transport layer is preferably adjacent to the light-emitting layer, or the electron transport layer closest to the anode in the multi-layer structure, such as the first electron transport layer in the two-layer structure, is preferably adjacent to the light-emitting layer. In another aspect of the present invention, a hole blocking layer or the like described later may be interposed between the single-layer electron transport layer and the light-emitting layer, or between the electron transport layer closest to the light-emitting layer in the multi-layer structure and the light-emitting layer.

[0707] The inventive compound is used as a material for the electron transport region, preferably as a material for the electron injection layer, electron transport layer, hole blocking layer, or exciton blocking layer, more preferably as a material for the electron injection layer or electron transport layer, and further preferably as a material for the electron transport layer.

[0708] In the two-layer electron transport layer, the inventive compound may be included in one of the first electron transport layer and the second electron transport layer, or may be included in both. In one aspect of the present invention, the inventive compound is preferably included only in the first electron transport layer. In another aspect, the inventive compound is preferably included only in the second electron transport layer. In yet another aspect, the inventive compound is preferably included in both the first electron transport layer and the second electron transport layer.

[0709] In one aspect of the present invention, the inventive compound included in the organic EL element contains at least one deuterium atom. Additionally, the inventive compound may be a mixture of an inventive compound in which all hydrogen atoms are protium atoms (hereinafter referred to as "protium form") and an inventive compound in which at least one of all hydrogen atoms is a deuterium atom (deuterium form). Among them, the protium form may contain deuterium atoms in a proportion below the natural abundance.

[0710] In one aspect of the present invention, from the perspective of manufacturing cost, the inventive compound included in the electron injection layer, the electron transport layer (including the first electron transport layer, the second electron transport layer, etc.), the hole blocking layer, and the exciton blocking layer is preferably the protium form.

[0711] Therefore, the present invention includes an organic EL element in which at least one layer selected from the electron injection layer, the electron transport layer, the hole blocking layer, and the exciton blocking layer contains an inventive compound consisting essentially of only the protium form. "An inventive compound consisting essentially of only the protium form" means that the content ratio of the protium form to the total amount of the inventive compound is 90 mol% or more, preferably 95 mol% or more, and more preferably 99 mol% or more (each including 100%).

[0712] As an electron transport layer material other than the inventive compound, examples thereof include

[0713] (1) metal complexes such as aluminum complexes, beryllium complexes, zinc complexes,

[0714] (2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives,

[0715] (3) polymer compounds.

[0716] As metal complexes, examples thereof 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).

[0717] As heteroaromatic compounds, examples thereof include: 2-(4-biphenyl)-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-biphenyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs).

[0718] 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).

[0719] 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.

[0720] Electron injection layer

[0721] The electron injection layer is a layer containing a material with high electron injection property. For the electron injection layer, alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), rare earth metals such as europium (Eu) and ytterbium (Yb), and compounds containing these metals can be used. As such compounds, for example, 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 can be cited. In addition, a plurality of these compounds can be used in combination.

[0722] In addition, a material obtained by containing an alkali metal, an alkaline earth metal, or a compound thereof in a material having electron transport property can be used. Specifically, a material obtained by containing magnesium (Mg) in Alq can be used. It should be noted that in this case, electron injection from the cathode can be performed more efficiently.

[0723] Alternatively, the electron injection layer can use a composite material obtained by mixing an organic compound and an electron donor (donor). Since the organic compound in such a composite material accepts electrons from the electron donor, the electron injection property and the 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 (metal complexes, heteroaromatic compounds, etc.) described above can be used. As the electron donor, any material that exhibits electron-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.

[0724] Cathode

[0725] The cathode is preferably a metal, an alloy, a conductive compound, and a mixture thereof having 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, 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 (for example, MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them can be cited.

[0726] It should be noted that when forming a cathode using an alkali metal, an alkaline earth metal, or an alloy containing them, a vacuum evaporation method or a sputtering method can be used. Additionally, when using silver paste or the like, a coating method, an inkjet method, or the like can be used.

[0727] It should be noted that by providing an electron injection layer, a cathode 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 work function value. These conductive materials can be formed into a film using a sputtering method, an inkjet method, a spin coating method, or the like.

[0728] Insulating layer

[0729] Since an electric field is applied to an ultrathin film in an organic EL element, pixel defects due to leakage or short circuit 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.

[0730] Examples of materials that can be used for the insulating layer include aluminum oxide, 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. It should be noted that mixtures or laminates of them can also be used.

[0731] Spacer layer

[0732] Regarding the above spacer layer, for example, in the case of laminating a fluorescent light-emitting layer and a phosphorescent light-emitting layer, 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. Additionally, a spacer layer can also be provided between multiple phosphorescent light-emitting layers.

[0733] Since the spacer layer is provided between light-emitting layers, a material having both electron-transporting properties and hole-transporting properties is preferably used. Additionally, 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. Examples of materials used for the spacer layer include the same materials as those used for the hole-transporting layer described above.

[0734] Blocking layer

[0735] A blocking layer such as an electron blocking layer, a hole blocking layer, or an exciton blocking layer can be provided adjacent to the light-emitting layer. An electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole-transporting layer, and a 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 confining the excitons within the light-emitting layer.

[0736] Each layer of the above organic EL element can be formed by a conventionally known vapor deposition method, coating method, or the like. For example, vapor deposition methods such as vacuum vapor deposition method and molecular beam epitaxy (MBE method), 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 forming the layer can be used to form it.

[0737] 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 preferably 5 nm to 10 μm, more preferably 10 nm to 0.2 μm.

[0738] The above organic EL element can be used in display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and electronic devices such as lighting and light-emitting devices for vehicle lamps.

[0739] Examples

[0740] Hereinafter, the present invention will be further described in detail using examples. The present invention is not limited to the following examples.

[0741] Inventive compounds used in the production of organic EL elements of Examples 1 to 20

[0742] [Chemical formula 52]

[0743]

[0744] Comparative compounds used in the production of organic EL elements of Comparative Examples 1 to 4

[0745] [Chemical formula 53]

[0746]

[0747] Comparative compound Ref-2 is compound 6-9 described in Patent Document 1.

[0748] Other compounds used in the production of organic EL elements of Examples 1 to 10 and Comparative Examples 1 to 2

[0749] [Chemical formula 54]

[0750]

[0751] Other compounds used in the production of organic EL elements of Examples 11 to 20 and Comparative Examples 3 to 4

[0752] [Chemical formula 55]

[0753]

[0754] Each organic EL element was fabricated as follows, and the EL element performance of each element was evaluated.

[0755] Example 1

[0756] Fabrication of Organic EL Element

[0757] 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 ITO was set to 130 nm.

[0758] The cleaned glass substrate with the transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, a hole injection layer with a film thickness of 10 nm was formed by co-evaporating Compound HT-1 and Compound HI-1 on the surface of the side where the transparent electrode was formed so as to cover the transparent electrode. The mass ratio of Compound HT-1 to Compound HI-1 was 97:3.

[0759] Next, Compound HT-1 was evaporated on the hole injection layer to form a hole transport layer with a film thickness of 80 nm.

[0760] Compound EBL-1 was evaporated on the hole transport layer to form an electron blocking layer with a film thickness of 5 nm.

[0761] Next, Compound BH-1 (host material) and Compound BD-1 (dopant material) were co-evaporated on the electron blocking 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 was 96:4.

[0762] Next, Compound HBL-1 was evaporated on the light-emitting layer to form a hole blocking layer with a film thickness of 5 nm.

[0763] Compound Inv-1 and Liq were co-evaporated on the hole blocking layer to form an electron transport layer with a film thickness of 20 nm. The mass ratio of Compound Inv-1 to Liq was 50:50.

[0764] LiF was evaporated on the electron injection layer to form an electron injection electrode with a film thickness of 1 nm.

[0765] Finally, metal Al was evaporated on the electron injection electrode to form a metal cathode with a film thickness of 80 nm.

[0766] The layer structure of the organic EL element of Example 1 is shown below. The numbers in parentheses are the film thicknesses (nm), and the ratio is the mass ratio.

[0767] ITO(130) / HT-1:HI-1 = 97:3(10) / HT-1(80) / EBL-1(5) / BH-1:BD-1 = 96:4(25) / HBL-1(5) / Inv-1:Liq = 50:50(20) / LiF(1) / Al(80)

[0768] Evaluation of Organic EL Device

[0769] External Quantum Efficiency (EQE)

[0770] The obtained organic EL device was driven at a constant direct current density of 10 mA / cm² at room temperature. 2 The luminance was measured using a luminance meter (Spectro Luminance Meter CS-1000, manufactured by Minolta Co., Ltd.), and the external quantum efficiency (%) was calculated based on the results. The results are shown in Table 1.

[0771] 95% Lifetime (LT95)

[0772] The obtained organic EL device was driven at a constant direct current density of 50 mA / cm² 2 The time until the luminance decreased to 95% of the initial luminance was measured and defined as the 95% lifetime (LT95). The results are shown in Table 1.

[0773] Examples 2 to 10 and Comparative Examples 1 to 2

[0774] Each compound described in Table 1 below was used in place of compound Inv-1, and each organic EL device was fabricated in the same manner as in Example 1 except for this.

[0775] For the external quantum efficiency (EQE) and 95% lifetime (LT95) of each obtained organic EL device, they were calculated in the same manner as in Example 1. The results are shown in Table 1.

[0776] [Table 1]

[0777] Table 1

[0778]

[0779] Fabrication of Organic EL Device

[0780] Example 11

[0781] A glass substrate (manufactured by Geomatec Co., Ltd.) with a 25 mm × 75 mm × 1.1 mm ITO transparent electrode (anode) 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.

[0782] The cleaned glass substrate with a transparent electrode is mounted on the substrate holder of a vacuum evaporation apparatus. First, the compound HT-2 and the compound HI-1 are co-evaporated on the surface of the side where the transparent electrode is formed so as to cover the transparent electrode, thereby forming a hole injection layer with a film thickness of 10 nm. The mass ratio of the compound HT-1 to the compound HI-1 is 97:3.

[0783] Next, the compound HT-2 is evaporated on the hole injection layer to form a hole transport layer with a film thickness of 80 nm.

[0784] The compound EBL-2 is evaporated on the hole transport layer to form an electron blocking layer with a film thickness of 5 nm.

[0785] Next, the compound BH-2 (host material) and the compound BD-1 (dopant material) are co-evaporated on the electron blocking layer to form a light-emitting layer with a film thickness of 25 nm. The mass ratio of the compound BH-2 to the compound BD-1 is 96:4.

[0786] Next, the compound HBL-1 is evaporated on the light-emitting layer to form a hole blocking layer with a film thickness of 5 nm.

[0787] The compound Inv-1 and Liq are co-evaporated on the hole blocking layer to form an electron transport layer with a film thickness of 20 nm. The mass ratio of the compound Inv-1 to Liq is 50:50.

[0788] LiF is evaporated on the electron injection layer to form an electron injection electrode with a film thickness of 1 nm.

[0789] Finally, metal Al is evaporated on the electron injection electrode to form a metal cathode with a film thickness of 80 nm.

[0790] The layer structure of the organic EL element of Example 11 is shown below. The numbers in parentheses are the film thicknesses (nm), and the ratios are mass ratios.

[0791] ITO(130) / HT-2:HI-1 = 97:3(10) / HT-2(80) / EBL-2(5) / BH-2:BD-1 = 96:4(25) / HBL-1(5) / Inv-1:Liq = 50:50(20) / LiF(1) / Al(80)

[0792] Examples 12 to 20 and Comparative Examples 3 to 4

[0793] Instead of the compound Inv-1, each compound described in Table 2 below was used, and except for this, each organic EL element was fabricated in the same manner as in Example 11.

[0794] Evaluation of organic EL elements

[0795] For the external quantum efficiency (EQE) and 95% lifetime (LT95) of each organic EL element, they were determined in the same manner as in Example 1. The results are shown in Table 2.

[0796] [Table 2]

[0797] Table 2

[0798]

[0799] From the results of Tables 1 and 2, it can be seen that compared with Comparative Compound Ref-1 and Comparative Compound Ref-2, Compounds Inv-1 to Inv-10 of the present invention provide organic EL elements with higher efficiency and longer lifetime.

[0800] Compounds Inv-1 to Inv-10 synthesized in Synthesis Examples 1 to 10

[0801] [Chemical Formula 56]

[0802]

[0803] Synthesis of Compound Inv-1 in Synthesis Example 1

[0804] [Chemical Formula 57]

[0805]

[0806] Intermediate A (3.9 g) and Intermediate B (4.9 g) were added to a mixed solvent of toluene (45 mL) and 1,2-dimethoxyethane (45 mL), and argon was introduced into the resulting solution for 5 minutes. Pd(Amphos) 2 Cl 2 (0.25 g) and an aqueous sodium carbonate solution (2 M, 12 mL) were added, and the mixture was heated at 75 °C for 6 hours while stirring under an argon atmosphere. The solvent was distilled off from the reaction solution, and the resulting solid was purified by silica gel column chromatography and further by recrystallization using toluene to obtain Compound Inv-1 (1.7 g, yield 27%).

[0807] As a result of mass spectrometry analysis, m / e = 687, confirming it as the target substance.

[0808] Synthesis of Compound Inv-2 in Synthesis Example 2

[0809] [Chemical Formula 58]

[0810]

[0811] Intermediate C (4.7 g) was used instead of Intermediate B, and otherwise the same operations as in Synthesis Example 1 were carried out to obtain Compound Inv-2 (5.0 g, yield 84%).

[0812] The result of mass spectrometry, m / e = 661, was confirmed as the target substance.

[0813] Synthesis of Compound Inv-3 in Synthesis Example 3

[0814] [Chemical Formula 59]

[0815]

[0816] Using 4.0 g of Intermediate A and replacing Intermediate B with Intermediate D (5.6 g), the same operations as in Synthesis Example 1 were carried out except for this, to obtain Compound Inv-3 (4.5 g, yield 65%).

[0817] The result of mass spectrometry, m / e = 687, was confirmed as the target substance.

[0818] Synthesis of Compound Inv-4 in Synthesis Example 4

[0819] [Chemical Formula 60]

[0820]

[0821] Intermediate A (7.0 g) and Intermediate E (4.4 g) were added to 1,4-dioxane (105 mL), and argon was bubbled through the resulting solution for 5 minutes. Pd(PPh 3 ) 4 (0.9 g) and an aqueous solution of tripotassium phosphate (2 M, 20 mL) were added thereto, and the mixture was heated under reflux for 7 hours while stirring under an argon atmosphere. The solvent was distilled off from the reaction solution, and the resulting solid was purified by silica gel column chromatography and then by suspension washing with acetone to obtain Compound Inv-4 (5.5 g, yield 55%).

[0822] The result of mass spectrometry, m / e = 561, was confirmed as the target substance.

[0823] Synthesis of Compound Inv-5 in Synthesis Example 5

[0824] [Chemical Formula 61]

[0825]

[0826] Intermediate A (6.0 g) and Intermediate F (4.1 g) were added to 1,2-dimethoxyethane (145 mL), and argon was bubbled through the resulting solution for 5 minutes. Pd(Amphos) 2 Cl 2(0.19 g) and an aqueous sodium carbonate solution (2 M, 20 mL) were heated at 75 °C for 7 hours while stirring under an argon atmosphere. The solvent was distilled off from the reaction solution, and the resulting solid was purified by silica gel column chromatography and further by recrystallization using toluene to obtain Compound Inv-5 (4.0 g, yield 52%).

[0827] As a result of mass spectrometry analysis, m / e = 561, confirming it as the target substance.

[0828] Synthesis Example 6 Synthesis of Compound Inv-6

[0829] [Chemical Formula 62]

[0830]

[0831] Intermediate G (4.0 g) was used in place of Intermediate F, and the same operations as in Synthesis Example 5 were performed to obtain Compound Inv-6 (4.1 g, yield 75%).

[0832] As a result of mass spectrometry analysis, m / e = 611, confirming it as the target substance.

[0833] Synthesis Example 7 Synthesis of Compound Inv-7

[0834] [Chemical Formula 63]

[0835]

[0836] Intermediate H (2.9 g) synthesized by the method described in KR2015-131998 and Intermediate I (4.1 g) were added to 1,2-dimethoxyethane (100 mL), and argon gas was passed through the resulting solution for 5 minutes. Pd(Amphos) 2 Cl 2 (0.12 g) and an aqueous sodium carbonate solution (2 M, 12 mL) were heated at 75 °C for 7 hours while stirring under an argon atmosphere. The solvent was distilled off from the reaction solution, and the resulting solid was purified by silica gel column chromatography and further by recrystallization using toluene to obtain Compound Inv-7 (4.0 g, yield 80%).

[0837] As a result of mass spectrometry analysis, m / e = 587, confirming it as the target substance.

[0838] Synthesis Example 8 Synthesis of Inv-8

[0839] [Chemical Formula 64]

[0840]

[0841] Intermediate J (5.4 g) was used instead of intermediate I, and the same procedure as in Synthesis Example 7 was carried out to obtain Compound Inv-8 (4.6 g, yield 79%).

[0842] As a result of mass spectrometry analysis, m / e = 687, and it was confirmed to be the target substance.

[0843] Synthesis of Compound Inv-9 in Synthesis Example 9

[0844] [Chemical Formula 65]

[0845]

[0846] Intermediate K (2.8 g) was used instead of intermediate H, and intermediate J (4.5 g) was used instead of intermediate I, and the same procedure as in Synthesis Example 7 was carried out to obtain Inv-9 (3.4 g, yield 55%).

[0847] As a result of mass spectrometry analysis, m / e = 621, and it was confirmed to be the target substance.

[0848] Synthesis of Compound Inv-10 in Synthesis Example 10

[0849] [Chemical Formula 66]

[0850]

[0851] Intermediate K (5.0 g) was used instead of intermediate F, and the same procedure as in Synthesis Example 5 was carried out to obtain Compound Inv-10 (6.1 g, yield 72%).

[0852] As a result of mass spectrometry analysis, m / e = 616, and it was confirmed to be the target substance.

[0853] Symbol Explanation

[0854] 1, 11 Organic EL Element

[0855] 2 Substrate

[0856] 3 Anode

[0857] 4 Cathode

[0858] 5 Light Emitting Layer

[0859] 6 Hole Transport Region (Hole Transport Layer)

[0860] 6a Hole Injection Layer

[0861] 6b Hole Transport Layer

[0862] 6c Electron Blocking Layer

[0863] 7 Electron Transport Region (Electron Transport Layer)

[0864] 7a hole blocking layer

[0865] 7b electron transport layer

[0866] 10, 20 light-emitting units

Claims

1. A compound represented by the following formula (3), wherein, R 1 to R 10 each independently represents a hydrogen atom, a fluorine atom, a cyano group, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted biphenyl group, an unsubstituted methyl group, an unsubstituted ethyl group, an unsubstituted n-propyl group, an unsubstituted isopropyl group, an unsubstituted n-butyl group, an unsubstituted isobutyl group, an unsubstituted sec-butyl group, an unsubstituted tert-butyl group, an unsubstituted dibenzofuranyl group or an unsubstituted dibenzothiophenyl group, Selected from R 1 ~R 10 Two adjacent ones among them do not bond to each other and thus do not form a ring structure; R 11 ~R 14 are all hydrogen atoms, Selected from R 11 to R 14 Two adjacent ones of them do not bond to each other and thus do not form a ring structure; Ar is an unsubstituted phenyl, unsubstituted biphenyl, unsubstituted terphenyl, unsubstituted naphthyl, unsubstituted phenanthryl, unsubstituted fluoranthenyl, unsubstituted 9,9-dimethylfluorenyl, unsubstituted 9,9-diphenylfluorenyl, or unsubstituted phenylnaphthyl; R 31 ~R 34 and R 36 ~R 39 are all hydrogen atoms Selected from R 31 ~R 34 and R 36 ~R 39 Among the two adjacent ones, none of them are bonded to each other, so no ring structure is formed. R 40 is a single bond bonded to *c, R 35 is a single bond bonded to *d.

2. The compound according to claim 1, wherein, Ar is an unsubstituted phenyl, unsubstituted biphenyl, or unsubstituted terphenyl.

3. The compound according to claim 1, wherein, Ar is an unsubstituted phenyl, unsubstituted biphenyl, or unsubstituted naphthyl.

4. The compound according to any one of claims 1 to 3, wherein, the diphenyltriazinyl structure of the formula (3) is represented by the following formula (4), wherein, R 2 ~R 4 and R 7 ~R 9 are the same as defined in formula (3). Among them, R 2 ~R 4 and R 7 ~R 9 at least one of which is a fluorine atom, a cyano group, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted biphenyl group, an unsubstituted methyl group, an unsubstituted ethyl group, an unsubstituted n-propyl group, an unsubstituted isopropyl group, an unsubstituted n-butyl group, an unsubstituted isobutyl group, an unsubstituted sec-butyl group, an unsubstituted tert-butyl group, an unsubstituted dibenzofuranyl group or an unsubstituted dibenzothiophenyl group. Selected from R 2 And R 3 , R 3 And R 4 , R 7 And R 8 , and R 8 And R 9 Among them, any two adjacent ones do not bond to each other and thus do not form a ring structure.

5. The compound according to any one of claims 1 to 3, wherein, the diphenyltriazinyl structure of the formula (3) is represented by the following formula (5), wherein, R 3 and R 8 are the same as defined in formula (3). Among them, R 3 and R 8 at least one of which is a fluorine atom, a cyano group, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted biphenyl group, an unsubstituted methyl group, an unsubstituted ethyl group, an unsubstituted n-propyl group, an unsubstituted isopropyl group, an unsubstituted n-butyl group, an unsubstituted isobutyl group, an unsubstituted sec-butyl group, an unsubstituted tert-butyl group, an unsubstituted dibenzofuranyl group or an unsubstituted dibenzothiophenyl group.

6. The compound according to claim 1, wherein, R 1 ~R 10 Each independently represents a hydrogen atom, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted biphenyl group, an unsubstituted methyl group, an unsubstituted ethyl group, an unsubstituted n-propyl group, an unsubstituted isopropyl group, an unsubstituted n-butyl group, an unsubstituted isobutyl group, an unsubstituted sec-butyl group or an unsubstituted tert-butyl group.

7. The compound according to claim 1, wherein, R 1 ~R 10 Each independently represents a hydrogen atom, an unsubstituted phenyl group, or an unsubstituted biphenyl group.

8. The compound according to claim 1, wherein, R 1 ~R 10 are all hydrogen atoms.

9. The compound according to claim 1, which is any one of the following, 。 10. The compound according to claim 1, which is any one of the following, 。 11. The compound according to claim 1, wherein, the compound contains at least 1 deuterium atom.

12. A material for an organic electroluminescent element, which contains the compound according to any one of claims 1 to 11.

13. An organic electroluminescent element having 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 contains the compound according to any one of claims 1 to 11.

14. The organic electroluminescent element according to claim 13, wherein, the compound contains at least 1 deuterium atom.

15. The organic electroluminescent element according to claim 13, wherein, the organic layer includes an electron transport region between the light-emitting layer and the cathode, and the electron transport region contains the compound.

16. The organic electroluminescent element according to claim 15, wherein, the electron transport region includes an electron transport layer, and the electron transport layer contains the compound.

17. The organic electroluminescent element according to any one of claims 13 to 16, wherein, the light-emitting layer contains a phosphorescent dopant material.

18. The organic electroluminescent element according to any one of claims 13 to 16, wherein, the light-emitting layer contains a fluorescent dopant material.

19. An electronic device, which contains the organic electroluminescent element according to any one of claims 13 to 18.

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