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

Abstract

A compound represented by the following formula (1) (each symbol in the formula is as defined in the specification), an organic electroluminescent element containing the compound, and an electronic device containing such an organic electroluminescent element.

Description

Technical Field

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

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

[0003] Patent Documents 1 to 8 disclose compounds used as materials for organic electroluminescent elements.

[0004] Prior Art Documents

[0005] Patent Documents

[0006] Patent Document 1: KR2018-0042943A Gazette

[0007] Patent Document 2: KR2018-0096458A Gazette

[0008] Patent Document 3: WO2014 / 163228A1 Gazette

[0009] Patent Document 4: WO2013 / 13183851A1 Gazette

[0010] Patent Document 5: KR1395080B1

[0011] Patent Document 6: KR2015-0138105A Gazette

[0012] Patent Document 7: KR2017-0094021A Gazette

[0013] Patent Document 8: US2016 / 0365515A1 Gazette Summary of the Invention

[0014] Problems to be Solved by the Invention

[0015] Conventionally, many compounds for organic EL elements have been reported, but there is still a need for compounds that further improve the performance of organic EL elements.

[0016] The present invention has been completed to solve the above problems, and an object thereof is to provide a compound that further improves the performance of an organic EL element, an organic EL element having further improved element performance, and an electronic device including the organic EL element.

[0017] Means for solving the problems

[0018] The present inventors have repeatedly and intensively studied the performance of organic EL elements containing the compounds described in Patent Documents 1 to 8 and other compounds, and as a result, it has been found that a monoamine in which one of the amino groups has a 4-carbazolyl group via a meta-phenylene linking group and the other has an aryl group containing only 6-membered rings provides an organic EL element in which the element performance is further improved.

[0019] In one aspect, the present invention provides a compound represented by the following formula (1).

[0020] [Chemical formula 1]

[0021]

[0022] (In the formula,

[0023] Ar 1 and Ar 2 each independently represent an aryl group containing only 6-membered rings having 6 to 50 ring-constituting carbon atoms, which may be substituted or unsubstituted.

[0024] Ar 3 represents an alkyl group having 1 to 50 carbon atoms, which may be substituted or unsubstituted, an aryl group having 6 to 50 ring-constituting carbon atoms, which may be substituted or unsubstituted, or a heterocyclic group having 5 to 50 ring atoms, which may be substituted or unsubstituted.

[0025] L 1 and L 2 each independently represent a single bond or an arylene group containing only 6-membered rings having 6 to 50 ring-constituting carbon atoms, which may be substituted or unsubstituted.

[0026] R 1 ~R 7 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, which may be substituted or unsubstituted, or an aryl group having 6 to 50 ring-constituting carbon atoms, which may be substituted or unsubstituted.

[0027] Among them, among the groups selected from R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , and R 6 and R 7In one or more of the groups, two adjacent ones can be bonded to each other to form a substituted or unsubstituted ring structure.

[0028] *a is bonded to carbon atom *1 or *2.

[0029] n is 0 or 1.

[0030] The above-mentioned Ar 1 、the above-mentioned Ar 2 、the above-mentioned L 1 and the above-mentioned L 2 In the above-mentioned "substituted or unsubstituted" cases, the substituents are each independently selected from unsubstituted alkyl groups having 1 to 50 carbon atoms, unsubstituted alkenyl groups having 2 to 50 carbon atoms, unsubstituted alkynyl groups having 2 to 50 carbon atoms, unsubstituted cycloalkyl groups having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), halogen atoms, cyano groups, nitro groups, and unsubstituted aryl groups having 6 to 50 ring carbon atoms that contain only 6-membered rings.

[0031] Among them, R 901 ~R 907 and two or more R 901 ~two or more R 907 are each independently selected from hydrogen atoms, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 50 ring carbon atoms, and substituted or unsubstituted aryl groups having 6 to 50 ring carbon atoms.

[0032] The substituents in the above-mentioned "substituted or unsubstituted" cases of the above-mentioned Ar 3 are selected from unsubstituted alkyl groups having 1 to 50 carbon atoms, unsubstituted alkenyl groups having 2 to 50 carbon atoms, unsubstituted alkynyl groups having 2 to 50 carbon atoms, unsubstituted cycloalkyl groups having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), cyano groups, nitro groups, unsubstituted aryl groups having 6 to 50 ring carbon atoms, and unsubstituted heterocyclic groups having 5 to 50 ring atoms.

[0033] Among them, R 901 ~R 907 and two or more R 901 ~two or more R 907Same as above.

[0034] The above-mentioned R 1 ~R 7 、the above-mentioned R 901 ~R 907 and the substituents in the above-mentioned "substituted or unsubstituted" cases in the above-mentioned ring structure are selected from unsubstituted alkyl groups having 1 to 50 carbon atoms, unsubstituted alkenyl groups having 2 to 50 carbon atoms, unsubstituted alkynyl groups having 2 to 50 carbon atoms, unsubstituted cycloalkyl groups having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), halogen atoms, cyano groups, nitro groups, unsubstituted aryl groups having 6 to 50 ring carbon atoms, and unsubstituted heterocyclic groups having 5 to 50 ring atoms.

[0035] Among them, R 901 ~R 907 and two or more R 901 ~two or more R 907 are the same as above.)

[0036] In another aspect, the present invention provides a material for an organic EL element containing the compound represented by the above formula (1).

[0037] In another aspect, the present invention provides an organic electroluminescent element having 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).

[0038] In another aspect, the present invention provides an electronic device including the above organic electroluminescent element.

[0039] Advantages of the Invention

[0040] The organic EL element containing the compound represented by the above formula (1) shows improved element performance. Brief Description of the Drawings

[0041] Figure 1 is a schematic diagram showing an example of the layer structure of an organic EL element according to one aspect of the present invention.

[0042] Figure 2 is a schematic diagram showing an example of the layer structure of another organic EL element according to one aspect of the present invention. Detailed Description

[0043] [Definitions]

[0044] In this specification, a hydrogen atom includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0045] In this specification, in a chemical structural formula, when no symbols such as "R" or the bondable position of "D" representing a deuterium atom are explicitly shown, a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom, is bonded.

[0046] In this specification, the number of ring-forming carbon atoms represents the number of carbon atoms among the atoms constituting the ring itself in a compound in which atoms are bonded to form a ring structure (e.g., a monocyclic compound, a fused-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 same applies to the "number of ring-forming carbon atoms" described below. For example, the number of ring-forming carbon atoms in a benzene ring is 6, the number of ring-forming carbon atoms in a naphthalene ring is 10, the number of ring-forming carbon atoms in a pyridine ring is 5, and the number of ring-forming carbon atoms in a furan ring is 4. Additionally, for example, the number of ring-forming carbon atoms in 9,9-diphenylfluorenyl is 13, and the number of ring-forming carbon atoms in 9,9'-spirobifluorenyl is 25.

[0047] Furthermore, when an alkyl group, for example, is substituted on a benzene ring as a substituent, 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 in a benzene ring substituted with an alkyl group is 6. Additionally, when an alkyl group, for example, is substituted on a naphthalene ring as a substituent, 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 in a naphthalene ring substituted with an alkyl group is 10.

[0048] In this specification, the number of ring-forming atoms represents the number of atoms constituting the ring itself in a compound in which atoms are bonded to form a ring structure (e.g., a monocyclic ring, a fused-ring, and a ring assembly) (e.g., 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 (e.g., hydrogen atoms that cap the bonds of atoms forming the ring) and atoms contained in the substituent when the ring is substituted with a substituent are not included in the number of ring-forming atoms. The same applies to the "number of ring-forming atoms" described below. For example, the number of ring-forming atoms in a pyridine ring is 6, the number of ring-forming atoms in a quinazoline ring is 10, and the number of ring-forming atoms in a furan ring is 5. For example, the hydrogen atoms bonded to the pyridine ring or the number of atoms constituting the substituent are not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms in a pyridine ring bonded with a hydrogen atom or a substituent is 6. Additionally, for example, the hydrogen atoms bonded to the carbon atoms of the quinazoline ring or the atoms constituting the substituent are not included in the number of quinazoline ring-forming atoms. Therefore, the number of ring-forming atoms in a quinazoline ring bonded with a hydrogen atom or a substituent is 10.

[0049] In this specification, in the expression "a ZZ group having XX to YY carbon atoms, which may be substituted or unsubstituted", "XX to YY carbon atoms" represents the number of carbon atoms of the ZZ group when it is unsubstituted, excluding the carbon atoms of the substituents when it is substituted. 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.

[0050] In this specification, in the expression "a ZZ group having XX to YY atoms, which may be substituted or unsubstituted", "XX to YY atoms" represents the number of atoms of the ZZ group when it is unsubstituted, excluding the atoms of the substituents when it is substituted. 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.

[0051] In this specification, an unsubstituted ZZ group means the case where "a ZZ group which may be substituted or unsubstituted" is an "unsubstituted ZZ group", and a substituted ZZ group means the case where "a ZZ group which may be substituted or unsubstituted" is a "substituted ZZ group".

[0052] In this specification, "unsubstituted" in the expression "a ZZ group which may be substituted or unsubstituted" means that the hydrogen atoms in the ZZ group are not replaced by substituents. The hydrogen atoms in the "unsubstituted ZZ group" are protium atoms, deuterium atoms or tritium atoms.

[0053] In addition, in this specification, "substituted" in the expression "a ZZ group which may be substituted or unsubstituted" means that one or more hydrogen atoms in the ZZ group are replaced by substituents. Similarly, "substituted" in the expression "a BB group substituted by an AA group" also means that one or more hydrogen atoms in the BB group are replaced by an AA group.

[0054] "Substituents described in this specification"

[0055] Hereinafter, the substituents described in this specification will be described.

[0056] Unless otherwise specified in this specification, the number of ring-forming carbon atoms of the "unsubstituted aryl" described in this specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18.

[0057] 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, more preferably 5 to 18.

[0058] 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, more preferably 1 to 6.

[0059] The number of carbon atoms of the "unsubstituted alkenyl" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified in this specification.

[0060] The number of carbon atoms of the "unsubstituted alkynyl" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified in this specification.

[0061] The number of ring-forming carbon atoms of the "unsubstituted cycloalkyl" described in this specification is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified in this specification.

[0062] The number of ring-forming carbon atoms of the "unsubstituted arylene" described in this specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified in this specification.

[0063] The number of ring-forming atoms of the "unsubstituted divalent heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified in this specification.

[0064] The number of carbon atoms of the "unsubstituted alkylene" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified in this specification.

[0065] · "substituted or unsubstituted aryl"

[0066] As specific examples (specific example group G1) of the "substituted or unsubstituted aryl" described in this specification, the following unsubstituted aryls (specific example group G1A) and substituted aryls (specific example group G1B) can be cited, etc. (Here, the unsubstituted aryl means the case where the "substituted or unsubstituted aryl" is "unsubstituted aryl", and the substituted aryl means the case where the "substituted or unsubstituted aryl" is "substituted aryl".) In this invention book, when only "aryl" is indicated, it includes both "unsubstituted aryl" and "substituted aryl".

[0067] "Substituted aryl" means a group in which one or more hydrogen atoms of "unsubstituted aryl" are replaced by substituents. Examples of "substituted aryl" include groups in which one or more hydrogen atoms of the "unsubstituted aryl" in the following specific example group G1A are replaced by substituents, and examples of the substituted aryl in the following specific example group G1B, etc. It should be noted that the examples of "unsubstituted aryl" and "substituted aryl" listed here are only for illustration, and the "substituted aryl" described in this specification also includes groups in which the hydrogen atoms bonded to the carbon atoms of the aryl itself in the "substituted aryl" of the following specific example group G1B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted aryl" of the following specific example group G1B are further replaced by substituents.

[0068] · Unsubstituted aryl (specific example group G1A):

[0069] Phenyl,

[0070] p - Biphenylyl,

[0071] m - Biphenylyl,

[0072] o - Biphenylyl,

[0073] p - Terphenyl - 4 - yl,

[0074] p - Terphenyl - 3 - yl,

[0075] p - Terphenyl - 2 - yl,

[0076] m - Terphenyl - 4 - yl,

[0077] m - Terphenyl - 3 - yl,

[0078] m - Terphenyl - 2 - yl,

[0079] o - Terphenyl - 4 - yl,

[0080] o - Terphenyl - 3 - yl,

[0081] o - Terphenyl - 2 - yl,

[0082] 1 - Naphthyl,

[0083] 2 - Naphthyl,

[0084] Anthracenyl,

[0085] Benzoanthracenyl,

[0086] Phenanthryl,

[0087] Benzo[a]phenanthryl,

[0088] Phenalenyl,

[0089] Pyrenyl,

[0090] Group,

[0091] Benzene, Group,

[0092] Triphenylene,

[0093] Benzotriphenylene,

[0094] Tetracenyl,

[0095] Pentacenyl,

[0096] Fluorenyl,

[0097] 9,9'-Spirobi(fluorenyl),

[0098] Benzofluorenyl,

[0099] Dibenzofluorenyl,

[0100] Fluoranthenyl,

[0101] Benzo(fluoranthenyl),

[0102] Perylenyl, and

[0103] 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).

[0104] [Chemical formula 2]

[0105]

[0106] [Chemical formula 3]

[0107]

[0108] · Substituted aryl group (specific example group G1B):

[0109] o-Tolyl,

[0110] m-Tolyl,

[0111] p-Tolyl,

[0112] p-Xylyl,

[0113] m-Xylyl,

[0114] o-Xylyl,

[0115] p-Isopropylphenyl,

[0116] m-Isopropylphenyl,

[0117] o-Isopropylphenyl,

[0118] p-tert-Butylphenyl,

[0119] m-tert-butylphenyl,

[0120] o-tert-butylphenyl,

[0121] 3,4,5-trimethylphenyl,

[0122] 9,9-dimethylfluorenyl,

[0123] 9,9-diphenylfluorenyl

[0124] 9,9-bis(4-methylphenyl)fluorenyl,

[0125] 9,9-bis(4-isopropylphenyl)fluorenyl,

[0126] 9,9-bis(4-tert-butylphenyl)fluorenyl,

[0127] cyanophenyl,

[0128] triphenylsilylphenyl,

[0129] trimethylsilylphenyl,

[0130] phenylnaphthyl,

[0131] naphthylphenyl, and

[0132] a group in which one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the above general formulas (TEMP-1) to (TEMP-15) are replaced with substituents.

[0133] · "substituted or unsubstituted heterocyclic group"

[0134] The "heterocyclic group" described in this specification is a cyclic group containing at least one heteroatom in the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.

[0135] The "heterocyclic group" described in this specification is a monocyclic group or a fused-ring group.

[0136] The "heterocyclic group" described in this specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0137] 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), substituted heterocyclic groups (specific example group G2B), etc. can be cited. (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to 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".

[0138] The "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of the "unsubstituted heterocyclic group" are 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 are substituted, and examples of the substituted heterocyclic group in the following specific example group G2B, etc. It should be noted that the examples of the "unsubstituted heterocyclic group" and the "substituted heterocyclic group" listed here are only for illustration, and the "substituted heterocyclic group" described in this specification also includes groups in which the hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself in the "substituted heterocyclic group" of specific example group G2B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted heterocyclic group" of specific example group G2B are further replaced by substituents.

[0139] 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).

[0140] Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of the monovalent heterocyclic groups derived from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific example group G2B4).

[0141] · Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):

[0142] Pyrrolyl,

[0143] Imidazolyl,

[0144] Pyrazolyl,

[0145] Triazolyl,

[0146] tetrazolyl,

[0147] oxazolyl,

[0148] isoxazolyl,

[0149] oxadiazolyl,

[0150] thiazolyl,

[0151] isothiazolyl,

[0152] thiadiazolyl,

[0153] pyridyl,

[0154] pyridazinyl,

[0155] pyrimidinyl,

[0156] pyrazinyl,

[0157] triazinyl,

[0158] indolyl,

[0159] isoindolyl,

[0160] indazolyl,

[0161] quinazolinyl,

[0162] quinolyl,

[0163] isoquinolyl,

[0164] cinnolinyl,

[0165] phthalazinyl,

[0166] quinazolinyl,

[0167] quinoxalinyl,

[0168] benzimidazolyl,

[0169] indazolyl,

[0170] phenanthrolinyl,

[0171] phenanthridinyl,

[0172] acridinyl,

[0173] phenazinyl,

[0174] carbazolyl,

[0175] benzocarbazolyl,

[0176] morpholinyl,

[0177] phenoxazinyl,

[0178] Phenothiazinyl,

[0179] Aza-carbazolyl, and diaza-carbazolyl.

[0180] · Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2):

[0181] Furyl,

[0182] Oxazolyl,

[0183] Isoxazolyl,

[0184] Oxadiazolyl,

[0185] Xanthenyl,

[0186] Benzofuryl,

[0187] Isobenzofuryl,

[0188] Dibenzofuryl,

[0189] Naphthobenzofuryl,

[0190] Benzoxazolyl,

[0191] Benzisoxazolyl,

[0192] Phenoxazinyl,

[0193] Morpholinyl,

[0194] Dinaphthofuryl,

[0195] Aza-dibenzofuryl,

[0196] Diaza-dibenzofuryl,

[0197] Aza-naphthobenzofuryl, and

[0198] Diaza-naphthobenzofuryl.

[0199] · Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3):

[0200] Thienyl,

[0201] Thiazolyl,

[0202] Isothiazolyl,

[0203] Thiadiazolyl,

[0204] Benzothienyl,

[0205] Isobenzothienyl,

[0206] dibenzothienyl,

[0207] naphthobenzothienyl,

[0208] benzothiazolyl,

[0209] benzoisothiazolyl,

[0210] phenothiazinyl,

[0211] dinaphthothienyl,

[0212] azadibenzothienyl,

[0213] diazadibenzothienyl,

[0214] azanaphthobenzothienyl, and

[0215] diazanaphthobenzothienyl.

[0216] · A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0217] [Chemical formula 4]

[0218]

[0219] [Chemical formula 5]

[0220]

[0221] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH 2 . Among them, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.

[0222] In the above general formulas (TEMP-16) to (TEMP-33), when at least one of X A and Y A is NH or CH 2In the case where, the monovalent heterocyclic group derived from the ring structure represented by the above general formulas (TEMP-16) to (TEMP-33) includes those obtained by removing one hydrogen atom from these NH or CH 2 a monovalent group obtained by removing one hydrogen atom.

[0223] · Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1):

[0224] (9-Phenyl)carbazolyl,

[0225] (9-Biphenyl)carbazolyl,

[0226] (9-Phenyl)phenylcarbazolyl,

[0227] (9-Naphthyl)carbazolyl,

[0228] Diphenylcarbazol-9-yl,

[0229] Phenylcarbazol-9-yl,

[0230] Methylbenzimidazolyl,

[0231] Ethylbenzimidazolyl,

[0232] Phenyltriazinyl,

[0233] Biphenyltriazinyl,

[0234] Diphenyltriazinyl,

[0235] Phenylquinazolinyl, and

[0236] Biphenylquinazolinyl.

[0237] · Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2):

[0238] Phenyldibenzofuranyl,

[0239] Methyldibenzofuranyl,

[0240] tert-Butyldibenzofuranyl, and

[0241] The monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0242] · Substituted heterocyclic groups containing a sulfur atom (specific example group G2B3):

[0243] Phenyldibenzothiophenyl,

[0244] Methyldibenzothiophenyl,

[0245] tert-Butyldibenzothiophenyl, and

[0246] The monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0247] · A group in which one or more hydrogen atoms of the monovalent heterocyclic group derived from the ring structure represented by the above general formulas (TEMP-16) to (TEMP-33) are replaced with substituents (specific example group G2B4):

[0248] The above "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 atom 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 CH 2 in the case of.

[0249] · "Substituted or unsubstituted alkyl"

[0250] As specific examples (specific example group G3) of the "substituted or unsubstituted alkyl" described in this specification, the following unsubstituted alkyls (specific example group G3A) and substituted alkyls (specific example group G3B) can be cited. (Here, the unsubstituted alkyl refers to the case where the "substituted or unsubstituted alkyl" is an "unsubstituted alkyl", and the substituted alkyl refers to the case where the "substituted or unsubstituted alkyl" is a "substituted alkyl".) Hereinafter, when only "alkyl" is mentioned, it includes both "unsubstituted alkyl" and "substituted alkyl".

[0251] "Substituted alkyl" refers to a group in which one or more hydrogen atoms in the "unsubstituted alkyl" are replaced with substituents. As specific examples of the "substituted alkyl", examples include groups in which one or more hydrogen atoms in the following "unsubstituted alkyls" (specific example group G3A) are replaced with substituents, and examples of the substituted alkyls (specific example group G3B). In this specification, the alkyl in the "unsubstituted alkyl" refers to a chain-like alkyl. Therefore, the "unsubstituted alkyl" includes a straight-chain "unsubstituted alkyl" and a branched-chain "unsubstituted alkyl". It should be noted that the examples of the "unsubstituted alkyl" and the examples of the "substituted alkyl" listed here are only for illustration, 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 the specific example group G3B are further replaced with substituents, and groups in which the hydrogen atoms of the substituents in the "substituted alkyl" of the specific example group G3B are further replaced with substituents.

[0252] · Unsubstituted alkyl (specific example group G3A):

[0253] Methyl,

[0254] Ethyl,

[0255] n-Propyl,

[0256] Isopropyl,

[0257] n-butyl,

[0258] isobutyl,

[0259] sec-butyl, and

[0260] tert-butyl.

[0261] · Substituted alkyl (specific example group G3B):

[0262] heptafluoropropyl (including isomers),

[0263] pentafluoroethyl,

[0264] 2,2,2-trifluoroethyl, and

[0265] trifluoromethyl.

[0266] · "Substituted or unsubstituted alkenyl"

[0267] As specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl" described in this specification, the following unsubstituted alkenyl (specific example group G4A), 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 the present invention, when only "alkenyl" is expressed, it includes both "unsubstituted alkenyl" and "substituted alkenyl".

[0268] The "substituted alkenyl" means a group in which one or more hydrogen atoms in the "unsubstituted alkenyl" are replaced by substituents. As specific examples of the "substituted alkenyl", groups having substituents of the following "unsubstituted alkenyl" (specific example group G4A), examples of the substituted alkenyl (specific example group G4B), etc. can be cited. It should be noted that the examples of the "unsubstituted alkenyl" and the examples of the "substituted alkenyl" listed here are only for illustration, 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 the 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 the specific example group G4B is further replaced by a substituent.

[0269] · Unsubstituted alkenyl (specific example group G4A):

[0270] vinyl,

[0271] allyl,

[0272] 1-butenyl,

[0273] 2-butenyl, and

[0274] 3-butenyl.

[0275] · Substituted alkenyl (specific example group G4B):

[0276] 1,3 - butadienyl,

[0277] 1 - methylvinyl,

[0278] 1 - methylallyl,

[0279] 1,1 - dimethylallyl,

[0280] 2 - methylallyl, and

[0281] 1,2 - dimethylallyl.

[0282] · "Substituted or unsubstituted alkynyl"

[0283] As specific examples (specific example group G5) of "substituted or unsubstituted alkynyl" described in this specification, the following unsubstituted alkynyls (specific example group G5A) etc. can be cited. (Here, the unsubstituted alkynyl means the case where "substituted or unsubstituted alkynyl" is "unsubstituted alkynyl".) Hereinafter, when only expressed as "alkynyl", it includes both "unsubstituted alkynyl" and "substituted alkynyl".

[0284] "Substituted alkynyl" means a group in which one or more hydrogen atoms in the "unsubstituted alkynyl" are replaced by substituents. As specific examples of "substituted alkynyl", groups in which one or more hydrogen atoms in the following "unsubstituted alkynyls" (specific example group G5A) are replaced by substituents etc. can be cited.

[0285] · Unsubstituted alkynyl (specific example group G5A):

[0286] Ethynyl

[0287] · "Substituted or unsubstituted cycloalkyl"

[0288] As specific examples (specific example group G6) of "substituted or unsubstituted cycloalkyl" described in this specification, the following unsubstituted cycloalkyls (specific example group G6A) and substituted cycloalkyls (specific example group G6B) etc. can be cited. (Here, the unsubstituted cycloalkyl means the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and the substituted cycloalkyl means the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl".) In this invention book, when only expressed as "cycloalkyl", it includes both "unsubstituted cycloalkyl" and "substituted cycloalkyl".

[0289] "Substituted cycloalkyl" means a group in which one or more hydrogen atoms in "unsubstituted cycloalkyl" are replaced by substituents. As specific examples of "substituted cycloalkyl", there may be mentioned groups in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl" (specific example group G6A) are replaced by substituents, examples of substituted cycloalkyl (specific example group G6B), and the like. It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only for illustration purposes, 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.

[0290] · Unsubstituted cycloalkyl (specific example group G6A):

[0291] Cyclopropyl,

[0292] Cyclobutyl,

[0293] Cyclopentyl,

[0294] Cyclohexyl,

[0295] 1-Adamantyl,

[0296] 2-Adamantyl,

[0297] 1-Norbornanyl, and

[0298] 2-Norbornanyl.

[0299] · Substituted cycloalkyl (specific example group G6B):

[0300] 4-Methylcyclohexyl.

[0301] · The group represented by "-Si(R 901 )(R 902 )(R 903 )"

[0302] As specific examples (specific example group G7) of the group represented by -Si(R 901 )(R 902 )(R 903 ) described in this specification, there may be mentioned

[0303] -Si(G1)(G1)(G1),

[0304] -Si(G1)(G2)(G2),

[0305] -Si(G1)(G1)(G2),

[0306] -Si(G2)(G2)(G2),

[0307] -Si(G3)(G3)(G3), and

[0308] -Si(G6)(G6)(G6).

[0309] Here,

[0310] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0311] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0312] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0313] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6. The multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other.

[0314] The multiple G2s in -Si(G1)(G2)(G2) are the same as or different from each other.

[0315] The multiple G1s in -Si(G1)(G1)(G2) are the same as or different from each other.

[0316] The multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other.

[0317] The multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other.

[0318] The multiple G6s in -Si(G6)(G6)(G6) are the same as or different from each other.

[0319] · The group represented by "-O-(R 904 )"

[0320] As a specific example (Specific Example Group G8) of the group represented by -O-(R 904 ) described in this specification, there can be cited

[0321] -O(G1),

[0322] -O(G2),

[0323] -O(G3), and

[0324] -O(G6).

[0325] Here,

[0326] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0327] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0328] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0329] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0330] · The group represented by "-S-(R 905 )"

[0331] As specific examples (Specific Example Group G9) of the group represented by -S-(R 905 ) described in this specification, there can be cited

[0332] -S(G1),

[0333] -S(G2),

[0334] -S(G3), and

[0335] -S(G6).

[0336] Here,

[0337] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0338] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0339] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0340] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0341] · The group represented by "-N(R 906 )(R 907 )"

[0342] 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

[0343] -N(G1)(G1),

[0344] -N(G2)(G2),

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

[0346] -N(G3)(G3), and

[0347] -N(G6)(G6).

[0348] Herein,

[0349] G1 is the "substituted or unsubstituted aryl" described in Specific Example Group G1.

[0350] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0351] G3 is the "substituted or unsubstituted alkyl" described in Specific Example Group G3.

[0352] G6 is the "substituted or unsubstituted cycloalkyl" described in Specific Example Group G6.

[0353] Multiple G1s in -N(G1)(G1) are the same as or different from each other.

[0354] Multiple G2s in -N(G2)(G2) are the same as or different from each other.

[0355] Multiple G3s in -N(G3)(G3) are the same as or different from each other.

[0356] Multiple G6s in -N(G6)(G6) are the same as or different from each other

[0357] · "Halogen atom"

[0358] 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.

[0359] · "Substituted or unsubstituted fluoroalkyl"

[0360] The "substituted or unsubstituted fluoroalkyl" described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl" is replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl" are replaced by fluorine atoms (perfluoro group). The carbon number of the "unsubstituted fluoroalkyl" is 1 to 50, preferably 1 to 30, more preferably 1 to 18, unless otherwise specified in this specification. The "substituted fluoroalkyl" is a group in which one or more hydrogen atoms of the "fluoroalkyl" are replaced by substituents. It should be noted that the "substituted fluoroalkyl" described in this specification also includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the "substituted fluoroalkyl" are further replaced by substituents, and a group in which one or more hydrogen atoms of the substituents in the "substituted fluoroalkyl" are further replaced by substituents. As specific examples of the "unsubstituted fluoroalkyl", examples of groups in which one or more hydrogen atoms in the above-mentioned "alkyl" (Specific Example Group G3) are replaced by fluorine atoms can be cited.

[0361] · "Substituted or unsubstituted haloalkyl"

[0362] 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 an 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. Specific examples of the "unsubstituted haloalkyl" include, for example, 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 also referred to as haloalkane.

[0363] · "Substituted or unsubstituted alkoxy"

[0364] Specific examples of the "substituted or unsubstituted alkoxy" described in this specification are groups 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.

[0365] · "Substituted or unsubstituted alkylthio"

[0366] Specific examples of the "substituted or unsubstituted alkylthio" described in this specification are groups 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.

[0367] · "Substituted or unsubstituted aryloxy"

[0368] Specific examples of the "substituted or unsubstituted aryloxy" described in this specification are groups 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.

[0369] · "Substituted or unsubstituted arylthio group"

[0370] 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.

[0371] · "Substituted or unsubstituted trialkylsilyl group"

[0372] 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 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.

[0373] · "Substituted or unsubstituted aralkyl group"

[0374] As a specific example of the "substituted or unsubstituted aralkyl group" 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 group" is a group in which a hydrogen atom of the "alkyl group" is replaced by an "aryl group" as a substituent, and it is a form of the "substituted alkyl group". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted by an "unsubstituted aryl group". The carbon number of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.

[0375] As specific examples of the "substituted or unsubstituted aralkyl group", 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. can be cited.

[0376] The substituted or unsubstituted aryl group described in this specification 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, -yl, triphenylenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl, etc., as long as it is not otherwise described in this specification.

[0377] The substituted or unsubstituted heterocyclic group described in this specification 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., as long as it is not otherwise described in this specification.

[0378] In this specification, the carbazolyl group is specifically any one of the following groups as long as it is not otherwise described in this specification.

[0379] [Chemical formula 6]

[0380]

[0381] In this specification, the (9-phenyl)carbazolyl group is specifically any one of the following groups as long as it is not otherwise described in this specification.

[0382] [Chemical formula 7]

[0383]

[0384] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents the bonding position.

[0385] In this specification, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any one of the following groups as long as it is not otherwise described in this specification.

[0386] [Chemical Formula 8]

[0387]

[0388] In the above general formulas (TEMP-34) to (TEMP-41), * represents the bonding position.

[0389] Unless otherwise specified in this specification, the substituted or unsubstituted alkyl groups are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.

[0390] · "Substituted or unsubstituted arylene"

[0391] Unless otherwise specified in this specification, the "substituted or unsubstituted arylene" is a divalent group derived by removing one hydrogen atom from the aryl ring of the above-mentioned "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.

[0392] · "Substituted or unsubstituted divalent heterocyclic group"

[0393] Unless otherwise specified in this specification, the "substituted or unsubstituted divalent heterocyclic group" is a divalent group derived by removing one hydrogen atom from the heterocyclic ring of the above-mentioned "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.

[0394] · "Substituted or unsubstituted alkylene"

[0395] Unless otherwise specified in this specification, the "substituted or unsubstituted alkylene" is a divalent group derived by removing one hydrogen atom from the alkyl chain of the above-mentioned "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.

[0396] 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).

[0397] [Chemical Formula 9]

[0398]

[0399] [Chemical Formula 10]

[0400]

[0401] In the above general formulas (TEMP-42) to (TEMP-52), Q 1 ~Q 10 are each independently a hydrogen atom or a substituent.

[0402] In the above general formulas (TEMP-42) to (TEMP-52), * represents the bonding position.

[0403] [Chemical Formula 11]

[0404]

[0405] In the above general formulas (TEMP-53) to (TEMP-62), Q 1 ~Q 10 are each independently a hydrogen atom or a substituent.

[0406] The group Q 9 and Q 10 can be bonded to each other via a single bond to form a ring.

[0407] In the above general formulas (TEMP-53) to (TEMP-62), * represents the bonding position.

[0408] [Chemical Formula 12]

[0409]

[0410] In the above general formulas (TEMP-63) to (TEMP-68), Q 1 ~Q 8 are each independently a hydrogen atom or a substituent.

[0411] In the above general formulas (TEMP-63) to (TEMP-68), * represents the bonding position.

[0412] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any group in the following general formulas (TEMP-69) to (TEMP-102).

[0413] [Chemical Formula 13]

[0414]

[0415] [Chemical Formula 14]

[0416]

[0417] [Chemical formula 15]

[0418]

[0419] In the above general formulas (TEMP-69) to (TEMP-82), Q 1 ~Q 9 are each independently a hydrogen atom or a substituent.

[0420] [Chemical formula 16]

[0421]

[0422] [Chemical formula 17]

[0423]

[0424] [Chemical formula 18]

[0425]

[0426] [Chemical formula 19]

[0427]

[0428] In the above general formulas (TEMP-83) to (TEMP-102), Q 1 ~Q 8 are each independently a hydrogen atom or a substituent.

[0429] The above is the description of "substituents described in this specification".

[0430] · "When bonding to form a ring"

[0431] In this specification, when it is described as "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", it 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".

[0432] For the cases of "one or more groups among two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring" and "one or more groups among 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 "forming a ring by bonding"), the following description is given. 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.

[0433] [Chemical formula 20]

[0434]

[0435] For example, when "one or more groups among two or more adjacent groups are bonded to each other to form a ring" among R 921 ~R 930 the group consisting of two adjacent ones that form one group refers to the group of R 921 and R 922 , the group of R 922 and R 923 , the group of R 923 and R 924 , the group of R 924 and R 930 , the group of R 930 and R 925 , the group of R 925 and R 926 , the group of R 926 and R 927 , the group of R 927 and R 928 , the group of R 928 and R 929 , and the group of R 929 and R 921 .

[0436] The above "one or more groups" means that two or more of the above groups consisting of two or more adjacent ones 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).

[0437] [Chemical formula 21]

[0438]

[0439] The case where a "group consisting of two or more adjacent ones" forms a ring means not only the case where a group consisting of "two" adjacent ones bonds as described above, but also the case where a group consisting of "three or more" adjacent ones bonds. For example, it means that R 921 and R 922 bond to each other to form ring Q A and R 922 and R 923 bond to each other to form ring Q C , and the case where a group consisting of three mutually adjacent ones (R 921 , R 922 and R 923 ) bonds to each other to form a ring and is fused to the anthracene parent skeleton. At this time, 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 .

[0440] [Chemical formula 22]

[0441]

[0442] The "monocyclic ring" or "fused ring" formed can be a saturated ring or an unsaturated ring only in terms of the structure of the formed ring. When "one group in the group consisting of two adjacent ones" forms a "monocyclic ring" or "fused ring", the "monocyclic ring" or "fused ring" can form a saturated ring or an unsaturated ring. For example, ring Q A and ring Q B formed in the above general formula (TEMP-104) are each a "monocyclic ring" or "fused ring". In addition, ring Q A and ring Q C formed in the above general formula (TEMP-105) are "fused rings". Ring Q A of the above general formula (TEMP-105) and ring Q C become a fused ring by fusing through ring Q A and ring Q C . If ring Q A of the above general formula (TMEP-104) is a benzene ring, then ring Q A is a monocyclic ring. If ring Q A of the above general formula (TMEP-104) is a naphthalene ring, then ring Q A is a fused ring.

[0443] "Unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. "Saturated ring" means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.

[0444] As a specific example of the aromatic hydrocarbon ring, a structure in which the group cited as a specific example in the specific example group G1 is capped with a hydrogen atom can be cited.

[0445] As a specific example of the aromatic heterocyclic ring, a structure in which the aromatic heterocyclic group cited as a specific example in the specific example group G2 is capped with a hydrogen atom can be cited.

[0446] As a specific example of the aliphatic hydrocarbon ring, a structure in which the group cited as a specific example in the specific example group G6 is capped with a hydrogen atom can be cited.

[0447] "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 that a ring is formed by the carbon atoms of the anthracene skeleton bonded by R 921 , the carbon atoms of the anthracene skeleton bonded by R 922 and one or more optional elements. As a specific example, in the case where a ring Q 921 is formed by R 922 and R A , when a single-ring unsaturated ring is formed by the carbon atoms of the anthracene skeleton bonded by R 921 , the carbon atoms of the anthracene skeleton bonded by R 922 and 4 carbon atoms, the ring formed by R 921 and R 922 is a benzene ring.

[0448] Here, the "optional element" is preferably at least one element selected from the group consisting of a carbon element, a nitrogen element, an oxygen element, and a sulfur element, unless otherwise specified in this specification. In the optional element (for example, when it is a carbon element or a nitrogen element), the bond that does not form a ring can be capped with a hydrogen atom or the like, or can be substituted with an "optional substituent" described later. When an optional element other than a carbon element is included, the formed ring is a heterocyclic ring.

[0449] 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 further preferably 3 or more and 5 or less, unless otherwise specified in this specification.

[0450] Unless otherwise specified in this specification, "single ring" is preferred over "fused ring".

[0451] Unless otherwise specified in this specification, "unsaturated ring" is preferred over "saturated ring".

[0452] Unless otherwise specified in this specification, the "monocyclic ring" is preferably a benzene ring.

[0453] Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring.

[0454] When "one or more of the groups composed of two or more adjacent groups" "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", unless otherwise specified in this specification, it is preferably: one or more of the groups composed of two or more adjacent groups bond 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, nitrogen, oxygen, and sulfur, with one or more and 15 or less.

[0455] 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.

[0456] 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 "saturated ring" or "unsaturated ring" has a substituent are the substituents described in the item of "substituents described in this specification" above.

[0457] The above is the description of the case of "one or more of the groups composed of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocyclic ring" and the case of "one or more of the groups composed of two or more adjacent groups bond to each other to form a substituted or unsubstituted fused ring" ("the case of bonding to form a ring").

[0458] · Substituents in the case of being expressed as "substituted or unsubstituted"

[0459] In one embodiment of this specification, the substituents in the case of being expressed as "substituted or unsubstituted" (in this specification, sometimes referred to as "optional substituents"), for example, are selected from

[0460] unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0461] unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0462] unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0463] unsubstituted cycloalkyl groups having 3 to 50 ring carbon atoms,

[0464] -Si(R 901)(R 902 )(R 903 )、

[0465] -O-(R 904 )、

[0466] -S-(R 905 )、

[0467] -N(R 906 )(R 907 )、

[0468] a halogen atom, a cyano group, a nitro group,

[0469] an unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0470] an unsubstituted heterocyclic group having 5 to 50 ring atoms

[0471] and groups in the group consisting of, etc.,

[0472] Herein, R 901 to R 907 are each independently

[0473] a hydrogen atom,

[0474] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0475] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0476] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0477] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0478] 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,

[0479] 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,

[0480] 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,

[0481] 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,

[0482] When there are two or more R 905 s, the two or more R 905Same as or different from each other,

[0483] At R 906 When there are two or more, two or more Rs 906 Same as or different from each other,

[0484] At R 907 When there are two or more, two or more Rs 907 Same as or different from each other.

[0485] In one embodiment, the substituent in the case where the above expression is "substituted or unsubstituted" is selected from

[0486] An alkyl group having 1 to 50 carbon atoms,

[0487] An aryl group having 6 to 50 ring carbon atoms, and

[0488] A heterocyclic group having 5 to 50 ring atoms

[0489] Groups in the group consisting of.

[0490] In one embodiment, the substituent in the case where the above expression is "substituted or unsubstituted" is selected from

[0491] An alkyl group having 1 to 18 carbon atoms,

[0492] An aryl group having 6 to 18 ring carbon atoms, and

[0493] A heterocyclic group having 5 to 18 ring atoms

[0494] Groups in the group consisting of.

[0495] Specific examples of each group of the above optional substituents are the specific examples of the substituents described in the item of "substituents described in this specification" above.

[0496] In this specification, unless otherwise noted, adjacent optional substituents can form a "saturated ring", or an "unsaturated ring" with each other, preferably form 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 form a benzene ring.

[0497] In this specification, unless otherwise noted, the optional substituent can further have a substituent. The substituent further had by the optional substituent is the same as the above optional substituent.

[0498] 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.

[0499] The compounds of the present invention will be described below.

[0500] 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 formulas included in formula (1) to be described later may be simply referred to as "invention compounds".

[0501] [Chemical formula 23]

[0502]

[0503] Hereinafter, the symbols in formula (1) and the formulas included in formula (1) to be described later will be described. It should be noted that the same symbols have the same meanings.

[0504] Ar 1 and Ar 2 Each independently represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and containing only 6-membered rings. It should be noted that fluorene is not included.

[0505] Examples of the above-mentioned substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and containing only 6-membered rings include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, benzoanthracenyl, phenanthryl, benzophenanthryl, phenalenyl, pyrenyl, group, or triphenylene, preferably phenyl, biphenyl, terphenyl, naphthyl, or phenanthryl, more preferably p-biphenyl, m-biphenyl, o-biphenyl, 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, 2-phenanthryl, or 9-phenanthryl, and further preferably phenyl, p-biphenyl, o-biphenyl, or p-terphenyl-4-yl.

[0506] Ar 3 is selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0507] Preferably, it is 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, and more preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0508] Details of the above-mentioned substituted or unsubstituted alkyl group having 1 to 50 carbon atoms are as described in "Substituents described in this specification".

[0509] The substituted or 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 further preferably ethyl.

[0510] Details of the above-mentioned substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms are as described in the above "Substituents described in this specification".

[0511] The above-mentioned substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms is preferably phenyl, 1-naphthyl, 2-naphthyl, biphenylyl, 2-phenanthryl, 9-phenanthryl, 9,9-dimethylfluoren-1-yl, or 9,9-dimethylfluoren-2-yl, more preferably phenyl, 1-naphthyl, or 2-naphthyl, and particularly preferably phenyl.

[0512] In one aspect of the present invention, Ar 3 is preferably unsubstituted phenyl, unsubstituted 1-naphthyl, or unsubstituted 2-naphthyl, and more preferably unsubstituted phenyl.

[0513] Details of the above-mentioned substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms are as described in the above "Substituents described in this specification".

[0514] The above-mentioned substituted or unsubstituted heterocyclic group is preferably 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, or 4-dibenzothiophenyl.

[0515] L 1 and L 2 each independently selected from a single bond and a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and containing only 6-membered rings. It should be noted that fluorene is not included.

[0516] The above-mentioned substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and containing only 6-membered rings is, for example, phenylene, biphenylene, terphenylenyl, naphthylene, anthrylene, benzanthrylene, phenanthrylene, benzophenanthrylene, aceanthrenyl, picenyl, pyrenylene, yl, benzo yl, perylenyl, or trisperylenyl, and is preferably phenylene or biphenylene.

[0517] In one aspect of the present invention, L 1 and L 2 are preferably a single bond.

[0518] Ar 1 and L 1 The adjacent aromatic hydrocarbon rings contained in do not crosslink, Ar 2 and L2 The adjacent aromatic hydrocarbon rings contained therein are not crosslinked.

[0519] R 1 ~R 7 Each independently represents 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-forming carbon atoms.

[0520] Among them, in one or more groups selected from R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , and R 6 and R 7 , two adjacent ones can be bonded to each other to form a substituted or unsubstituted ring structure.

[0521] The details of the above-mentioned substituted or unsubstituted alkyl group having 1 to 50 carbon atoms are as described in the above "Substituents described in this specification".

[0522] The 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 further preferably tert-butyl.

[0523] The details of the above-mentioned substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms are as described in the above "Substituents described in this specification".

[0524] The above-mentioned substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms is preferably phenyl, 1-naphthyl, 2-naphthyl, or biphenylyl, more preferably phenyl.

[0525] In one embodiment of the present invention, R 1 ~R 7 are preferably hydrogen atoms.

[0526] In one embodiment of the present invention, it is preferred that in one or more groups selected from R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , and R 6 and R 7 , two adjacent ones are bonded to each other without forming a substituted or unsubstituted ring structure.

[0527] *a is bonded to carbon atom *1 or *2.

[0528] In one embodiment of the present invention, *a is preferably bonded to carbon atom *2.

[0529] n is 0 or 1.

[0530] In one embodiment of the present invention, n is preferably 0.

[0531] The above-mentioned Ar 1 、the above-mentioned Ar 2 、the above-mentioned L 1 and the above-mentioned L 2 For the "substituted or unsubstituted" substituents in the above, they are each independently selected from unsubstituted alkyl groups having 1 to 50 carbon atoms, unsubstituted alkenyl groups having 2 to 50 carbon atoms, unsubstituted alkynyl groups having 2 to 50 carbon atoms, unsubstituted cycloalkyl groups having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), halogen atoms, cyano groups, nitro groups, and unsubstituted aryl groups having 6 to 50 ring carbon atoms containing only 6-membered rings.

[0532] Among them, R 901 ~R 907 and two or more R 901 ~two or more R 907 are each independently selected from hydrogen atoms, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 50 ring carbon atoms, and substituted or unsubstituted aryl groups having 6 to 50 ring carbon atoms.

[0533] The substituents in the above-mentioned "substituted or unsubstituted" case of the above-mentioned Ar 3 are selected from unsubstituted alkyl groups having 1 to 50 carbon atoms, unsubstituted alkenyl groups having 2 to 50 carbon atoms, unsubstituted alkynyl groups having 2 to 50 carbon atoms, unsubstituted cycloalkyl groups having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), cyano groups, nitro groups, unsubstituted aryl groups having 6 to 50 ring carbon atoms, and unsubstituted heterocyclic groups having 5 to 50 ring atoms.

[0534] Among them, R 901 ~R 907and two or more Rs 901 ~ two or more Rs 907 The same as above.

[0535] The above-mentioned R 1 ~R 7 、the above-mentioned R 901 ~R 907 、and the substituents in the above-mentioned "substituted or unsubstituted" case in the above-mentioned ring structure are selected from unsubstituted alkyl groups having 1 to 50 carbon atoms, unsubstituted alkenyl groups having 2 to 50 carbon atoms, unsubstituted alkynyl groups having 2 to 50 carbon atoms, unsubstituted cycloalkyl groups having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), halogen atoms, cyano groups, nitro groups, unsubstituted aryl groups having 6 to 50 ring carbon atoms, and unsubstituted heterocyclic groups having 5 to 50 ring atoms.

[0536] Among them, R 901 ~R 907 and two or more Rs 901 ~ two or more Rs 907 The same as above.

[0537] As described above, the "hydrogen atom" used in this specification includes protium atoms, deuterium atoms, and tritium atoms. Therefore, the inventive compounds may also include deuterium atoms of natural origin.

[0538] In addition, deuterium atoms can also be deliberately introduced into the inventive compounds by using deuterated compounds for a part or all of the starting compounds. Therefore, in one aspect of the present invention, the inventive compounds contain at least 1 deuterium atom. That is, the inventive compounds may be the compounds represented by formula (1) or a preferred form thereof, and at least 1 of the hydrogen atoms contained in the compound is a deuterium atom.

[0539] In addition, in one aspect of the present invention, in formula (1), the hydrogen atoms of the aryl group containing only 6-membered rings represented by Ar 1 and Ar 2 , the hydrogen atoms of the alkyl group, aryl group, or heterocyclic group represented by Ar 3 , the hydrogen atoms of the arylene group containing only 6-membered rings represented by L 1 and L 2 , and R 1 ~R 7At least one hydrogen atom among the hydrogen atoms of the hydrogen atom shown, the hydrogen atoms of an alkyl group or an aryl group, the hydrogen atoms of the meta-phenylene linking group bonded to the 4-carbazolyl group, and the hydrogen atoms of the phenylene group bonded to the meta-phenylene linking group and bonded to N is a deuterium atom.

[0540] In one aspect of the present invention, the inventive compound contains deuterium. In this case, the deuteration rate (the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the inventive compound) depends on the deuteration rate of the starting compounds used. It is generally difficult to make the deuteration rate of all the starting compounds used 100%. Therefore, the deuteration rate of the inventive compound is less than 100%, preferably 95% or less, more preferably 90% or less, and further preferably 80% or less.

[0541] When the inventive compound contains deuterium, the deuteration rate (the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the inventive compound) is 1% or more, preferably 3% or more, more preferably 5% or more, and further preferably 10% or more.

[0542] The inventive compound may also be a mixture of a deuterated compound and a non-deuterated compound, or a mixture of two or more compounds having different deuteration rates. The deuteration rate of such a mixture (the ratio of the number of deuterium atoms contained in the mixture to the total number of hydrogen atoms in the inventive compound) is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and less than 100%.

[0543] In one aspect of the present invention, the inventive compound contains deuterium, and at least one hydrogen atom among the hydrogen atoms of the aryl group composed only of 6-membered rings selected from Ar 1 and Ar 2 is a deuterium atom. The deuteration rate (the ratio of the number of deuterium atoms to the total number of hydrogen atoms of the aryl group shown by Ar 1 and Ar 2 is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and less than 100%.

[0544] In one aspect of the present invention, the inventive compound contains deuterium, and at least one hydrogen atom among the hydrogen atoms of the alkyl group or aryl group selected from Ar 3 is a deuterium atom. The deuteration rate (the ratio of the number of deuterium atoms to the total number of hydrogen atoms of the alkyl group or aryl group shown by Ar 3 is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and less than 100%.

[0545] In one aspect of the present invention, the inventive compound contains deuterium, and is selected from L 1 and L 2At least one of the hydrogen atoms of the arylene group containing only 6-membered rings shown has a deuterium atom. The deuteration rate (the ratio of the number of deuterium atoms to the total number of hydrogen atoms of the arylene group shown in L 1 and L 2 ) is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and less than 100%.

[0546] In one aspect of the present invention, the inventive compound contains deuterium, and at least one of the hydrogen atoms selected from the hydrogen atoms of the alkyl group, aryl group or heterocyclic group and the hydrogen atoms of R 1 ~R 7 shown is a deuterium atom. The deuteration rate (the ratio of the number of deuterium atoms to the total number of hydrogen atoms of R 1 ~R 7 shown and the total number of hydrogen atoms of the alkyl group or aryl group) is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and less than 100%.

[0547] In one aspect of the present invention, the inventive compound contains deuterium, and at least one of the hydrogen atoms selected from the hydrogen atoms of the m-phenylene linking group bonded to the 4-carbazolyl group is a deuterium atom. The deuteration rate (the ratio of the number of deuterium atoms to the total number of hydrogen atoms of the m-phenylene linking group bonded to the 4-carbazolyl group) is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and less than 100%.

[0548] In one aspect of the present invention, the inventive compound contains deuterium, and at least one of the hydrogen atoms selected from the hydrogen atoms of the phenyl group bonded to N and bonded to the m-phenylene linking group is a deuterium atom. The deuteration rate (the ratio of the number of deuterium atoms to the total number of hydrogen atoms of the phenyl group bonded to N and bonded to the m-phenylene linking group) is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and less than 100%.

[0549] The method for producing the inventive compound is not particularly limited, and those skilled in the art can easily produce it by the method described in the following examples or by a method obtained by changing the method by referring to known synthetic methods.

[0550] Specific examples of the inventive compound of the present invention are shown below, but are not limited thereto.

[0551] In the following specific examples, D represents a deuterium atom.

[0552] [Chemical formula 24]

[0553]

[0554] [Chemical formula 25]

[0555]

[0556] [Chemical Formula 26]

[0557]

[0558] [Chemical Formula 27]

[0559]

[0560] [Chemical Formula 28]

[0561]

[0562] [Chemical Formula 29]

[0563]

[0564] [Chemical Formula 30]

[0565]

[0566] [Chemical Formula 31]

[0567]

[0568] [Chemical Formula 32]

[0569]

[0570] [Chemical Formula 33]

[0571]

[0572] [Chemical Formula 34]

[0573]

[0574] [Chemical Formula 35]

[0575]

[0576] [Chemical Formula 36]

[0577]

[0578] [Chemical Formula 37]

[0579]

[0580] [Chemical Formula 38]

[0581]

[0582] [Chemical Formula 39]

[0583]

[0584] [Chemical Formula 40]

[0585]

[0586] [Chemical Formula 41]

[0587]

[0588] [Chemical Formula 42]

[0589]

[0590] [Chemical Formula 43]

[0591]

[0592] [Chemical Formula 44]

[0593]

[0594] [Chemical Formula 45]

[0595]

[0596] [Chemical Formula 46]

[0597]

[0598] [Chemical Formula 47]

[0599]

[0600] [Chemical Formula 48]

[0601]

[0602] [Chemical Formula 49]

[0603]

[0604] [Chemical Formula 50]

[0605]

[0606] [Chemical Formula 51]

[0607]

[0608] [Chemical Formula 52]

[0609]

[0610] [Chemical Formula 53]

[0611]

[0612] [Chemical Formula 54]

[0613]

[0614] [Chemical Formula 55]

[0615]

[0616] [Chemical Formula 56]

[0617]

[0618] [Chemical Formula 57]

[0619]

[0620] [Chemical Formula 58]

[0621]

[0622] [Chemical Formula 59]

[0623]

[0624] [Chemical Formula 60]

[0625]

[0626] [Chemical Formula 61]

[0627]

[0628] [Chemical Formula 62]

[0629]

[0630] [Chemical Formula 63]

[0631]

[0632] [Chemical Formula 64]

[0633]

[0634] [Chemical Formula 65]

[0635]

[0636] [Chemical Formula 66]

[0637]

[0638] [Chemical Formula 67]

[0639]

[0640] [Chemical Formula 68]

[0641]

[0642] [Chemical Formula 69]

[0643]

[0644] [Chemical Formula 70]

[0645]

[0646] [Chemical Formula 71]

[0647]

[0648] [Chemical Formula 72]

[0649]

[0650] [Chemical Formula 73]

[0651]

[0652] [Chemical Formula 74]

[0653]

[0654] [Chemical Formula 75]

[0655]

[0656] [Chemical Formula 76]

[0657]

[0658] [Chemical Formula 77]

[0659]

[0660] [Chemical Formula 78]

[0661]

[0662] [Chemical Formula 79]

[0663]

[0664] [Chemical Formula 80]

[0665]

[0666] [Chemical Formula 81]

[0667]

[0668] [Chemical Formula 82]

[0669]

[0670] [Chemical Formula 83]

[0671]

[0672] [Chemical Formula 84]

[0673]

[0674] [Chemical Formula 85]

[0675]

[0676] [Chemical Formula 86]

[0677]

[0678] [Chemical Formula 87]

[0679]

[0680] [Chemical Formula 88]

[0681]

[0682] [Chemical Formula 89]

[0683]

[0684] [Chemical Formula 90]

[0685]

[0686] [Chemical Formula 91]

[0687]

[0688] [Chemical Formula 92]

[0689]

[0690] [Chemical Formula 93]

[0691]

[0692] [Chemical Formula 94]

[0693]

[0694] [Chemical Formula 95]

[0695]

[0696] [Chemical Formula 96]

[0697]

[0698] [Chemical Formula 97]

[0699]

[0700] [Chemical Formula 98]

[0701]

[0702] [Chemical Formula 99]

[0703]

[0704] [Chemical Formula 100]

[0705]

[0706] [Chemical Formula 101]

[0707]

[0708] [Chemical Formula 102]

[0709]

[0710] [Chemical Formula 103]

[0711]

[0712] [Chemical Formula 104]

[0713]

[0714] [Chemical Formula 105]

[0715]

[0716] [Chemical Formula 106]

[0717]

[0718] [Chemical Formula 107]

[0719]

[0720] [Chemical Formula 108]

[0721]

[0722] [Chemical Formula 109]

[0723]

[0724] [Chemical Formula 110]

[0725]

[0726] [Chemical Formula 111]

[0727]

[0728] [Chemical Formula 112]

[0729]

[0730] [Chemical Formula 113]

[0731]

[0732] [Chemical Formula 114]

[0733]

[0734] [Chemical Formula 115]

[0735]

[0736] [Chemical Formula 116]

[0737]

[0738] [Chemical Formula 117]

[0739]

[0740] [Chemical Formula 118]

[0741]

[0742] [Chemical Formula 119]

[0743]

[0744] [Chemical Formula 120]

[0745]

[0746] [Chemical Formula 121]

[0747]

[0748] [Chemical Formula 122]

[0749]

[0750] [Chemical Formula 123]

[0751]

[0752] [Chemical Formula 124]

[0753]

[0754] [Chemical Formula 125]

[0755]

[0756] [Chemical Formula 126]

[0757]

[0758] [Chemical Formula 127]

[0759]

[0760] [Chemical Formula 128]

[0761]

[0762] [Chemical Formula 129]

[0763]

[0764] [Chemical Formula 130]

[0765]

[0766] [Chemical Formula 131]

[0767]

[0768] [Chemical Formula 132]

[0769]

[0770] [Chemical Formula 133]

[0771]

[0772] [Chemical Formula 134]

[0773]

[0774] [Chemical Formula 135]

[0775]

[0776] [Chemical Formula 136]

[0777]

[0778] [Chemical Formula 137]

[0779]

[0780] [Chemical Formula 138]

[0781]

[0782] [Chemical Formula 139]

[0783]

[0784] [Chemical Formula 140]

[0785]

[0786] [Chemical Formula 141]

[0787]

[0788] [Chemical Formula 142]

[0789]

[0790] [Chemical Formula 143]

[0791]

[0792] [Chemical Formula 144]

[0793]

[0794] [Chemical Formula 145]

[0795]

[0796] [Chemical Formula 146]

[0797]

[0798] [Chemical Formula 147]

[0799]

[0800] [Chemical Formula 148]

[0801]

[0802] [Chemical Formula 149]

[0803]

[0804] [Chemical Formula 150]

[0805]

[0806] [Chemical Formula 151]

[0807]

[0808] [Chemical Formula 152]

[0809]

[0810] [Chemical Formula 153]

[0811]

[0812] [Chemical Formula 154]

[0813]

[0814] [Chemical Formula 155]

[0815]

[0816] [Chemical Formula 156]

[0817]

[0818] [Chemical Formula 157]

[0819]

[0820] [Chemical Formula 158]

[0821]

[0822] [Chemical Formula 159]

[0823]

[0824] [Chemical Formula 160]

[0825]

[0826] [Chemical Formula 161]

[0827]

[0828] [Chemical Formula 162]

[0829]

[0830] [Chemical Formula 163]

[0831]

[0832] [Chemical Formula 164]

[0833]

[0834] [Chemical Formula 165]

[0835]

[0836] [Chemical Formula 166]

[0837]

[0838] [Chemical Formula 167]

[0839]

[0840] [Chemical Formula 168]

[0841]

[0842] [Chemical Formula 169]

[0843]

[0844] [Chemical Formula 170]

[0845]

[0846] [Chemical Formula 171]

[0847]

[0848] [Chemical Formula 172]

[0849]

[0850] [Chemical Formula 173]

[0851]

[0852] [Chemical Formula 174]

[0853]

[0854] [Chemical Formula 175]

[0855]

[0856] [Chemical Formula 176]

[0857]

[0858] [Chemical Formula 177]

[0859]

[0860] [Chemical Formula 178]

[0861]

[0862] [Chemical Formula 179]

[0863]

[0864] [Chemical Formula 180]

[0865]

[0866] [Chemical Formula 181]

[0867]

[0868] [Chemical Formula 182]

[0869]

[0870] [Chemical Formula 183]

[0871]

[0872] [Chemical Formula 184]

[0873]

[0874] [Chemical Formula 185]

[0875]

[0876] [Chemical Formula 186]

[0877]

[0878] [Chemical Formula 187]

[0879]

[0880] [Chemical Formula 188]

[0881]

[0882] [Chemical Formula 189]

[0883]

[0884] [Chemical Formula 190]

[0885]

[0886] [Chemical Formula 191]

[0887]

[0888] [Chemical Formula 192]

[0889]

[0890] [Chemical Formula 193]

[0891]

[0892] [Chemical Formula 194]

[0893]

[0894] [Chemical Formula 195]

[0895]

[0896] [Chemical Formula 196]

[0897]

[0898] [Chemical Formula 197]

[0899]

[0900] [Chemical Formula 198]

[0901]

[0902] [Chemical Formula 199]

[0903]

[0904] [Chemical Formula 200]

[0905]

[0906] [Chemical Formula 201]

[0907]

[0908] [Chemical Formula 202]

[0909]

[0910] [Chemical Formula 203]

[0911]

[0912] [Chemical formula 204]

[0913]

[0914] [Chemical formula 205]

[0915]

[0916] [Chemical formula 206]

[0917]

[0918] [Chemical formula 207]

[0919]

[0920] [Chemical formula 208]

[0921]

[0922] [Chemical formula 209]

[0923]

[0924] [Chemical formula 210]

[0925]

[0926] [Chemical formula 211]

[0927]

[0928] [Chemical formula 212]

[0929]

[0930] [Chemical formula 213]

[0931]

[0932] [Chemical formula 214]

[0933]

[0934] [Chemical formula 215]

[0935]

[0936] [Chemical formula 216]

[0937]

[0938] [Chemical formula 217]

[0939]

[0940] [Chemical formula 218]

[0941]

[0942] [Chemical formula 219]

[0943]

[0944] [Chemical formula 220]

[0945]

[0946] [Chemical formula 221]

[0947]

[0948] [Chemical formula 222]

[0949]

[0950] [Chemical formula 223]

[0951]

[0952] [Chemical formula 224]

[0953]

[0954] [Chemical formula 225]

[0955]

[0956] [Chemical formula 226]

[0957]

[0958] [Chemical formula 227]

[0959]

[0960] [Chemical formula 228]

[0961]

[0962] [Chemical formula 229]

[0963]

[0964] [Chemical formula 230]

[0965]

[0966] [Chemical formula 231]

[0967]

[0968] [Chemical formula 232]

[0969]

[0970] [Chemical formula 233]

[0971]

[0972] [Chemical formula 234]

[0973]

[0974] [Chemical formula 235]

[0975]

[0976] [Chemical formula 236]

[0977]

[0978] [Chemical formula 237]

[0979]

[0980] [Chemical formula 238]

[0981]

[0982] [Chemical formula 239]

[0983]

[0984] [Chemical formula 240]

[0985]

[0986] [Chemical formula 241]

[0987]

[0988] [Chemical formula 242]

[0989]

[0990] [Chemical formula 243]

[0991]

[0992] [Chemical formula 244]

[0993]

[0994] [Chemical Formula 245]

[0995]

[0996] Materials for Organic EL Devices

[0997] 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.

[0998] Organic EL Device

[0999] 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 the inventive compound.

[1000] 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.) disposed between the anode and the light-emitting layer, the light-emitting layer, a spacer layer, an electron transport region (electron injection layer, electron transport layer, hole blocking layer, etc.) disposed 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 hole transport region or the light-emitting layer of a fluorescent or phosphorescent EL device, more preferably used as a material for the hole transport region, still more preferably used as a material for the hole injection layer, hole transport layer, electron blocking layer, or exciton blocking layer, and particularly preferably used as a material for the hole injection layer or hole transport layer.

[1001] The organic EL device of the present invention may be a monochromatic light-emitting device of fluorescent or phosphorescent light-emitting type, or may be a white light-emitting device of fluorescent / phosphorescent hybrid type. It may be a simple type having a single light-emitting unit or a tandem type having a plurality of light-emitting units. Among them, a fluorescent light-emitting type device is preferred. Here, the "light-emitting unit" refers to the smallest unit that includes an organic layer, at least one layer of which is a light-emitting layer and emits light through recombination of the injected holes and electrons.

[1002] For example, as a representative device configuration of a simple organic EL device, the following device configurations can be cited.

[1003] (1) Anode / Light-emitting Unit / Cathode

[1004] In addition, the above light-emitting unit may also be a multi-layer type having a plurality of phosphorescent light-emitting layers and fluorescent light-emitting layers. In this case, an interlayer may also be provided between the respective light-emitting layers for the purpose of preventing excitons generated in the phosphorescent light-emitting layer from diffusing into the fluorescent light-emitting layer. The following shows the representative layer structures of the simple type light-emitting units. The layers in parentheses are optional.

[1005] (a) (Hole injection layer / ) Hole transport layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[1006] (b) (Hole injection layer / ) Hole transport layer / Phosphorescent light-emitting layer Electron transport layer ( / Electron injection layer)

[1007] (c) (Hole injection layer / ) Hole transport layer / First fluorescent light-emitting layer / Second fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[1008] (d) (Hole injection layer / ) Hole transport layer / First phosphorescent light-emitting layer / Second phosphorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[1009] (e) (Hole injection layer / ) Hole transport layer / Phosphorescent light-emitting layer / Interlayer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[1010] (f) (Hole injection layer / ) Hole transport layer / First phosphorescent light-emitting layer / Second phosphorescent light-emitting layer / Interlayer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[1011] (g) (Hole injection layer / ) Hole transport layer / First phosphorescent light-emitting layer / Interlayer / Second phosphorescent light-emitting layer / Interlayer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[1012] (h) (Hole injection layer / ) Hole transport layer / Phosphorescent light-emitting layer / Interlayer / First fluorescent light-emitting layer / Second fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[1013] (i) (Hole injection layer / ) Hole transport layer / Electron blocking layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[1014] (j) (Hole injection layer / ) Hole transport layer / Electron blocking layer / Phosphorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[1015] (k) (Hole injection layer / ) Hole transport layer / Exciton blocking layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[1016] (1) (Hole injection layer / ) Hole transport layer / Exciton blocking layer / Phosphorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[1017] (m) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Fluorescent emission layer / Electron transport layer ( / Electron injection layer)

[1018] (n) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Phosphorescent emission layer / Electron transport layer ( / Electron injection layer)

[1019] (o) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Fluorescent emission layer / First electron transport layer / Second electron transport layer ( / Electron injection layer)

[1020] (p) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Phosphorescent emission layer / First electron transport layer / Second electron transport layer ( / Electron injection layer)

[1021] (q) (Hole injection layer / ) Hole transport layer / Fluorescent emission layer / Hole blocking layer / Electron transport layer ( / Electron injection layer)

[1022] (r) (Hole injection layer / ) Hole transport layer / Phosphorescent emission layer / Hole blocking layer / Electron transport layer ( / Electron injection layer)

[1023] (s) (Hole injection layer / ) Hole transport layer / Fluorescent emission layer / Exciton blocking layer / Electron transport layer ( / Electron injection layer)

[1024] (t) (Hole injection layer / ) Hole transport layer / Phosphorescent emission layer / Exciton blocking layer / Electron transport layer ( / Electron injection layer)

[1025] Each of the above phosphorescent or fluorescent emission layers can be set as a layer showing mutually different emission colors. Specifically, in the above light-emitting unit (f), there can be cited 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, etc.

[1026] It should be noted that an electron blocking layer can be appropriately provided between each light-emitting layer and the hole transport layer or the spacer layer. In addition, a hole blocking layer can be appropriately provided between each light-emitting layer and the electron transport layer. By providing the electron blocking layer and the hole blocking layer, electrons or holes can be sealed in the light-emitting layer, increasing the recombination probability of charges in the light-emitting layer, thereby improving the light-emitting efficiency.

[1027] As a representative element structure of the tandem organic EL element, the following element structures can be cited.

[1028] (2) Anode / First light-emitting unit / Intermediate layer / Second light-emitting unit / Cathode

[1029] Here, as the above-described first light-emitting unit and second light-emitting unit, for example, they can be independently selected from the above-described light-emitting units.

[1030] Generally, the above-described intermediate layer is also referred to as an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, an intermediate insulating layer. The intermediate layer supplies electrons to the first light-emitting unit and holes to the second light-emitting unit, and can be formed of known materials.

[1031] Figure 1 It is a schematic diagram showing an example of the configuration of the organic EL element of the present invention. The organic EL element 1 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10 disposed between the anode 3 and the cathode 4. The light-emitting unit 10 has a light-emitting layer 5. A hole transport region 6 (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, thereby further improving the generation efficiency of excitons in the light-emitting layer 5.

[1032] Figure 2 It is a schematic diagram showing another configuration of the organic EL element of the present invention. The organic EL element 11 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 20 disposed between the anode 3 and the cathode 4. The light-emitting unit 20 has a light-emitting layer 5. The hole transport region disposed between the anode 3 and the light-emitting layer 5 is formed by a hole injection layer 6a, a first hole transport layer 6b, and a second hole transport layer 6c. In addition, the electron transport region disposed between the light-emitting layer 5 and the cathode 4 is formed by a first electron transport layer 7a and a second electron transport layer 7b.

[1033] 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 according to the molecular structure. That is, the phosphorescent host refers to a material that forms a phosphorescent light-emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material for forming a fluorescent light-emitting layer. The same applies to the fluorescent host.

[1034] Substrate

[1035] The substrate is used as a support for the organic EL element. As the substrate, for example, a plate such as glass, quartz, or plastic 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, or polyvinyl chloride can be cited. In addition, an inorganic vapor deposition film can also be used.

[1036] Anode

[1037] 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. 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.

[1038] These materials are usually formed by sputtering. For example, indium zinc oxide can be formed by sputtering using a target in which 1 to 10 wt% of zinc oxide is added to indium oxide; 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.

[1039] 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, as the electrode material, generally used 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.

[1040] Elements belonging to Group 1 or Group 2 of the periodic table, which are materials with a small work function, can also be used, that is, alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (such as MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them, etc. It should be noted that when using alkali metals, alkaline earth metals, and alloys containing them to form the anode, vacuum evaporation or sputtering can be used. In addition, when using silver paste, etc., coating, inkjet, etc. can be used.

[1041] Hole injection layer

[1042] 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.

[1043] As a hole injection material other than the inventive compound, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. can be used.

[1044] 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. as low molecular organic compounds can also be cited.

[1045] 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 an acid such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly(styrenesulfonic acid) (PAni / PSS), etc. can also be used.

[1046] Furthermore, acceptor materials such as hexaazatriphenylene (HAT) compounds represented by the following formula (K) are also preferably used.

[1047] [Chemical formula 246]

[1048]

[1049] (In the above formula, R 21 ~R 26Each 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, two adjacent ones selected from R 21 and R 22 , R 23 and R 24 , and R 25 and R 26 can be bonded to each other to form a group represented by -CO-O-CO-).

[1050] As R 27 , examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, etc.

[1051] Hole transport layer

[1052] The hole transport layer is a layer containing a material with high hole transportability (hole transport material), formed between the anode and the light-emitting layer, or formed between the hole injection layer and the light-emitting layer when present. The inventive compound can be used alone or in combination with the following compounds for the hole transport layer.

[1053] The hole transport layer can be a single-layer structure or a multi-layer structure including two or more layers. 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 embodiment of the present invention, the single-layer hole transport layer described above is preferably adjacent to the light-emitting layer. In addition, 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 embodiment of the present invention, an electron blocking layer or the like 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 and the light-emitting layer in the multi-layer structure.

[1054] In the two-layer hole transport layer described above, the inventive compound can be included in one of the first hole transport layer and the second hole transport layer, or can be included in both.

[1055] In one aspect of the present invention, it is preferred that the inventive compound is only included in the first hole transport layer. In another aspect, it is preferred that the inventive compound is only included in the second hole transport layer. In another aspect, it is preferred that the inventive compound is included in the first hole transport layer and the second hole transport layer.

[1056] In one aspect of the present invention, from the perspective of manufacturing cost, the inventive compound contained in one or both of the first hole transport layer and the second hole transport layer is preferably protium.

[1057] The above-mentioned protium compound refers to the inventive compound in which all hydrogen atoms in formula (1) are protium atoms.

[1058] Therefore, the present invention includes an organic EL element, wherein one or both of the above-mentioned first hole transport layer and the above-mentioned second hole transport layer contain an inventive compound consisting essentially of only the protium compound. The "inventive compound consisting essentially of only the protium compound" means that the content ratio of the protium compound is 90 mol% or more, preferably 95 mol% or more, more preferably 99 mol% or more (including 100% respectively) relative to the total amount of the compound represented by formula (1).

[1059] As a hole transport layer material other than the inventive compound, for example, an aromatic amine compound, a carbazole derivative, an anthracene derivative, etc. can be used.

[1060] 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'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) can be mentioned. The above compounds have a hole mobility of 10 -6 cm 2 / Vs or more.

[1061] As the carbazole derivative, 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 mentioned.

[1062] As the anthracene derivative, for example, 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth) can be mentioned.

[1063] It is also possible to use polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), etc.

[1064] Among them, as long as the hole transport property is higher than the electron transport property of the compound, compounds other than the above can also be used.

[1065] Dopant material for the light-emitting layer

[1066] The light-emitting layer is a layer containing a material with high luminescence (dopant material), and various materials can be used. For example, fluorescent luminescent materials and phosphorescent luminescent materials can be used as dopant materials. Fluorescent luminescent materials are compounds that emit light from the singlet excited state, and phosphorescent luminescent materials are compounds that emit light from the triplet excited state.

[1067] As the blue fluorescent luminescent material that can be used for the light-emitting layer, pyrene derivatives, styrylamine derivatives, derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. can be used. Specifically, N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), etc. can be cited.

[1068] As the green fluorescent luminescent material that can be used for the light-emitting layer, aromatic amine derivatives, etc. 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-benzenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-benzenediamine (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.

[1069] As a red fluorescent luminescent material that can be used in the light-emitting layer, tetracene derivatives, diamine derivatives, etc. 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.

[1070] 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 are 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(CF 3 ppy) 2 (pic)), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III) acetylacetonate (abbreviation: FIrracac), etc. can be cited.

[1071] As a green phosphorescent luminescent material that can be used in the light-emitting layer, iridium complexes, etc. are used. Tris(2-phenylpyridine-N,C2')iridium(III) (abbreviation: Ir(ppy) 3 ) and bis(2-phenylpyridine-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(ppy) 2 (acac)), bis(1,2-diphenyl-1H-benzimidazole)iridium(III) acetylacetonate (abbreviation: Ir(pbi) 2 (acac)), bis(benzo[h]quinoline)iridium(III) acetylacetonate (abbreviation: Ir(bzq) 2 (acac)), etc. can be cited.

[1072] As a red phosphorescent luminescent material that can be used in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used. Specifically, 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)), 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.

[1073] In addition, tris(acetylacetonato)(monophenanthroline) terbium(III) (abbreviation: Tb(acac) 3 (Phen)), tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline) europium(III) (abbreviation: Eu(DBM) 3 (Phen)), tris[1-(2-thienoyl)-3,3,3-trifluoroacetonato](monophenanthroline) europium(III) (abbreviation: Eu(TTA) 3 (Phen)) and other rare earth metal complexes can be used as phosphorescent materials because they emit light (electronic transitions between different multiplicities) from rare earth metal ions.

[1074] Host material of the light-emitting layer

[1075] The light-emitting layer can be configured to disperse the above dopant materials in other materials (host materials). It is preferable to use a material with a lowest unoccupied molecular orbital energy level (LUMO energy level) higher than that of the dopant material and a highest occupied molecular orbital energy level (HOMO energy level) lower than that of the dopant material.

[1076] As the host material, for example, the following can be used:

[1077] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes,

[1078] (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives,

[1079] (3) Condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or derivatives, etc.,

[1080] (4) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives.

[1081] For example, tris(8-hydroxyquinolinato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-hydroxyquinolinato)aluminum(III) (abbreviation: Almq 3 ) and bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq 2) Metal complexes such as 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);

[1082] Heterocyclic compounds such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2’,2”-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP);

[1083] Fused aromatic compounds such as 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9’-bianthracene (abbreviation: BANT), 9,9’-(stilbene-3,3’-diyl)diphenanthrene (abbreviation: DPNS), 9,9’-(stilbene-4,4’-diyl)diphenanthrene (abbreviation: DPNS2), 3,3’,3”-(benzene-1,3,5-triyl)tripyrene (abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenyl and

[1084] Aromatic amine compounds such as 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), etc. Two or more host materials can be used.

[1085] Especially in the case of a blue fluorescent element, the following anthracene compounds are preferably used as the host material.

[1086] [Chemical formula 247]

[1087]

[1088] [Chemical formula 248]

[1089]

[1090] [Chemical formula 249]

[1091]

[1092] Electron transport layer

[1093] The electron transport layer is a layer containing a material with high electron transport property (electron transport material), formed between the light-emitting layer and the cathode, or formed between the electron injection layer and the light-emitting layer when present.

[1094] The electron transport layer can be a single-layer structure or a multi-layer structure including more than two layers. 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 embodiment of the present invention, it is preferred that the single-layer electron transport layer is adjacent to the light-emitting layer. In addition, it is preferred that the electron transport layer closest to the anode in the multi-layer structure, for example, the first electron transport layer in the two-layer structure, is adjacent to the light-emitting layer. In another embodiment of the present invention, a hole blocking layer or the like described below can also 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 and the light-emitting layer in the multi-layer structure.

[1095] For example, the following can be used in the electron transport layer,

[1096] (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes,

[1097] (2) Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives,

[1098] (3) Polymer compounds.

[1099] Examples of the metal complex include tris(8-hydroxyquinoline)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-hydroxyquinoline)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (abbreviation: 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), and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviation: ZnBTZ).

[1100] Examples of the heteroaromatic compound 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), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs).

[1101] As the high molecular compound, for example, 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) can be cited.

[1102] 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 also be used for the electron transport layer.

[1103] Electron injection layer

[1104] The electron injection layer is a layer containing a material with high electron injectability. 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 mixed and used.

[1105] In addition, a material obtained by making a material having electron transportability contain an alkali metal, an alkaline earth metal, or a compound thereof can also be used. Specifically, a material obtained by making magnesium (Mg) contained in A1q can be used. It should be noted that at this time, electron injection from the cathode can be performed more efficiently.

[1106] Alternatively, a composite material obtained by mixing an organic compound and an electron donor (donor) can also be used for the electron injection layer. Since the organic compound accepts electrons from the electron donor, such a composite material has excellent electron injectability and electron transportability. At this time, as the organic compound, a material excellent in the transport of the accepted electrons is preferable. Specifically, for example, the above materials constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) can be used. As the electron donor, any material that exhibits electron-donating properties 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, and ytterbium. In addition, alkali metal oxides and alkaline earth metal oxides are preferable, and examples include lithium oxide, calcium oxide, and barium oxide. 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.

[1107] Cathode

[1108] The cathode preferably uses metals, alloys, conductive compounds, and mixtures thereof with a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them, etc.

[1109] It should be noted that in the case of using alkali metals, alkaline earth metals, and alloys containing them to form the cathode, vacuum evaporation or sputtering can be used. In addition, in the case of using silver paste or the like, coating methods, inkjet methods, etc. can be used.

[1110] It should be noted that by providing an electron injection layer, various conductive materials such as Al, Ag, ITO, graphene, indium tin oxide containing silicon or silicon oxide, etc. can be used to form the cathode regardless of the work function. These conductive materials can be formed into films using sputtering, inkjet, spin coating, etc.

[1111] Insulating layer

[1112] Since an electric field is applied to an ultrathin film in an organic EL element, pixel defects due to leakage and short circuit are likely to occur. To prevent such pixel defects, an insulating layer including an insulating thin film layer can be inserted between a pair of electrodes.

[1113] Examples of materials used in 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 and laminates thereof can be used.

[1114] Spacer layer

[1115] The above spacer layer refers to a layer provided between a fluorescent light-emitting layer and a phosphorescent light-emitting layer, for example, to prevent excitons generated in the phosphorescent light-emitting layer from diffusing into the fluorescent light-emitting layer or to adjust the carrier balance. In addition, the spacer layer can also be provided between multiple phosphorescent light-emitting layers.

[1116] Since the spacer layer is provided between light-emitting layers, a material having both electron-transporting properties and hole-transporting properties is preferred. In addition, in order to prevent the diffusion of triplet energy in adjacent phosphorescent light-emitting layers, the triplet energy is preferably 2.6 eV or more. Examples of materials for the spacer layer include the same materials as those for the hole-transporting layer described above.

[1117] Blocking layer

[1118] Blocking layers such as an electron blocking layer, a hole blocking layer, and an exciton blocking layer can be provided adjacent to the light-emitting layer. The electron blocking layer refers to a layer that prevents electrons from leaking from the light-emitting layer to the hole transport layer, and the hole blocking layer refers to a layer that prevents holes from leaking from the light-emitting layer to the electron transport 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.

[1119] 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, it can be formed by a vapor deposition method such as a vacuum vapor deposition method or a molecular beam epitaxy method (MBE method), or a conventionally known method such as a coating method including dip coating, spin coating, casting, bar coating, or roll coating using a solution of a compound for forming the layer.

[1120] There is no particular limitation on the film thickness of each layer. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur. On the contrary, if it is too thick, a high driving voltage is required and the efficiency deteriorates. Therefore, it is usually 5 nm to 10 μm, more preferably 10 nm to 0.2 μm.

[1121] 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 light-emitting devices such as lighting fixtures and vehicle-use lamps.

[1122] Examples

[1123] Hereinafter, the present invention will be described in more detail using examples, but the present invention is not limited to the following examples.

[1124] Inventive compounds used in the production of the organic EL elements of Examples 1 to 17

[1125] [Chemical formula 250]

[1126]

[1127] [Chemical formula 251]

[1128]

[1129] Comparative compounds used in the production of the organic EL elements of Comparative Examples 1 to 5

[1130] [Chemical formula 252]

[1131]

[1132] Other compounds used in the production of the organic EL elements of Examples 1 to 17 and Comparative Examples 1 to 5

[1133] [Chemical formula 253]

[1134]

[1135] Fabrication of Organic EL Element

[1136] Example 1

[1137] 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.

[1138] The above-mentioned glass substrate with a transparent electrode after cleaning was mounted on the substrate holder of a vacuum evaporation apparatus. First, compound HT-1 and compound HI-1 were co-evaporated on the surface of the side where the transparent electrode was formed so as to cover the transparent electrode, forming a hole injection layer with a film thickness of 10 nm. The mass ratio of compound HT-1 to compound HI-1 (HT-1:HI-1) was 97:3.

[1139] Next, compound HT-1 was evaporated on the hole injection layer, forming a first hole transport layer with a film thickness of 80 nm.

[1140] Next, compound Inv-1 was evaporated on this first hole transport layer, forming a second hole transport layer with a film thickness of 10 nm.

[1141] Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated on this second hole transport layer, forming a light-emitting layer with a film thickness of 25 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 96:4.

[1142] Next, compound ET-1 was evaporated on this light-emitting layer, forming a first electron transport layer with a film thickness of 5 nm.

[1143] Next, compound ET-2 and Liq were co-evaporated on this first electron transport layer, forming a second electron transport layer with a film thickness of 20 nm. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50.

[1144] Next, LiF was evaporated on this second electron transport layer, forming an electron injection electrode with a film thickness of 1 nm.

[1145] Then, metal Al was evaporated on this electron injection electrode to form a metal cathode with a film thickness of 50 nm.

[1146] The layer structure of the organic EL element of Example 1 obtained in this way is shown below.

[1147] ITO(130) / HT-1:HI-1 = 97:3(10) / HT-1(80) / Inv-1(10) / BH-1:BD-1 = 96:4(25) / ET-1(5) / ET-2:Liq = 50:50(20) / LiF(1) / Al(50)

[1148] In the above layer structure, the numbers in parentheses are film thickness (nm), and the ratios are mass ratios.

[1149] Comparative Example 1

[1150] Except for replacing the compound of the second hole transport layer with the compound described in Table 1, the same operations as in Example 1 were performed to fabricate each organic EL element.

[1151] Evaluation of Organic EL Elements

[1152] The external quantum efficiency of each fabricated organic EL element was evaluated. The evaluation results are shown in Table 1.

[1153] Measurement of External Quantum Efficiency (EQE)

[1154] The obtained organic EL element was subjected to direct current constant current drive at a current density of 10 mA / cm² at room temperature 2 and the luminance was measured using a spectro-radiance meter "CS-1000" (manufactured by Konica Minolta Inc.). The external quantum efficiency (%) was calculated from the measurement results.

[1155] [Table 1]

[1156] Table 1

[1157]

[1158] From the results in Table 1, it is clearly known that the inventive compound (Compound Inv-1) having a 4-carbazolyl group via a meta-phenylene linking group on one side of the amino group shows a significantly improved external quantum efficiency compared to the amine compound (Comparative Compound Ref-1) having a 3-carbazolyl group via a meta-phenylene linking group on one side of the amino group.

[1159] Example 2

[1160] A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then subjected to UV ozone cleaning for 30 minutes. The film thickness of ITO was set to 130 nm.

[1161] The above-mentioned glass substrate with a transparent electrode after cleaning is installed on the substrate holder of a vacuum evaporation device. First, the compound HT-1 and the compound HI-1 are co-evaporated in a manner that covers the transparent electrode on the surface of the side where the transparent electrode is formed, 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 (HT-1:HI-1) is 97:3.

[1162] Next, the compound HT-1 is evaporated on the hole injection layer, forming a first hole transport layer with a film thickness of 80 nm.

[1163] Next, the compound Inv-2 is evaporated on the first hole transport layer, forming a second hole transport layer with a film thickness of 10 nm.

[1164] Next, the compound BH-2 (host material) and the compound BD-1 (dopant material) are co-evaporated on the second hole transport layer, forming a light-emitting layer with a film thickness of 25 nm. The mass ratio of the compound BH-2 to the compound BD-1 (BH-2:BD-1) is 96:4.

[1165] Next, the compound ET-1 is evaporated on the light-emitting layer, forming a first electron transport layer with a film thickness of 5 nm.

[1166] Next, the compound ET-2 and Liq are co-evaporated on the first electron transport layer, forming a second electron transport layer with a film thickness of 20 nm. The mass ratio of the compound ET-2 to Liq (ET-2:Liq) is 50:50.

[1167] Next, LiF is evaporated on the second electron transport layer, forming an electron injection electrode with a film thickness of 1 nm.

[1168] Then, metal Al is evaporated on the electron injection electrode, forming a metal cathode with a film thickness of 50 nm.

[1169] The layer structure of the organic EL element of Example 1 obtained in this way is shown below.

[1170] ITO(130) / HT-1:HI-1 = 97:3(10) / HT-1(80) / Inv-2(10) / BH-2:BD-1 = 96:4(25) / ET-1(5) / ET-2:Liq = 50:50(20) / LiF(1) / Al(50)

[1171] In the above layer structure, the numbers in parentheses are the film thickness (nm), and the ratio is the mass ratio.

[1172] Examples 3 to 8, Comparative Examples 2 and 3

[1173] Except for replacing the compound of the second hole transport layer with the compound described in Table 2, each organic EL element was fabricated in the same manner as in Example 2.

[1174] Evaluation of Organic EL Element

[1175] The external quantum efficiency EQE of the fabricated organic EL element was evaluated by the same method as described above. The evaluation results are shown in Table 2.

[1176] [Table 2]

[1177] Table 2

[1178]

[1179] Example 9

[1180] A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then subjected to UV ozone cleaning for 30 minutes. The film thickness of ITO was set to 130 nm.

[1181] The cleaned glass substrate with the transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, compound HT-2 and compound HI-1 were co-evaporated on the surface of the side where the transparent electrode was formed so as to cover the transparent electrode, and a hole injection layer with a film thickness of 10 nm was formed. The mass ratio of compound HT-2 to compound HI-1 (HT-2:HI-1) was 97:3.

[1182] Next, compound HT-2 was evaporated on the hole injection layer to form a first hole transport layer with a film thickness of 80 nm.

[1183] Next, compound Inv-1 was evaporated on the first hole transport layer to form a second hole transport layer with a film thickness of 10 nm.

[1184] Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated on the second hole transport layer to form a light-emitting layer with a film thickness of 25 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 96:4.

[1185] Next, compound ET-3 was evaporated on the light-emitting layer to form a first electron transport layer with a film thickness of 10 nm.

[1186] Next, compound ET-4 was evaporated on the first electron transport layer to form a second electron transport layer with a film thickness of 15 nm.

[1187] Next, LiF was vapor-deposited on the second electron transport layer to form an electron injection electrode with a film thickness of 1 nm.

[1188] Then, metal Al was vapor-deposited on the electron injection electrode to form a metal cathode with a film thickness of 50 nm.

[1189] The layer structure of the organic EL element of Example 1 thus obtained is shown below.

[1190] ITO(130) / HT-2: HI-1 = 97:3(10) / HT-2(80) / Inv-1(10) / BH-1: BD-.1 = 96:4(25) / ET-3(10) / ET-4(15) / LiF(1) / Al(50)

[1191] In the above layer structure, the numbers in parentheses are the film thickness (nm), and the ratios are mass ratios.

[1192] Examples 10 to 17, Comparative Examples 4 and 5

[1193] Except that the compound of the second hole transport layer was replaced with the compound described in Table 3, each organic EL element was fabricated in the same manner as in Example 9.

[1194] Evaluation of organic EL elements

[1195] The external quantum efficiency EQE of the fabricated organic EL elements was evaluated by the same method as above. The evaluation results are shown in Table 3.

[1196] [Table 3]

[1197] Table 3

[1198]

[1199] From the results of Tables 1 to 3, it is clearly understood that the inventive compounds having a 4-carbazolyl group via a meta-phenylene linking group on one side of the amino group show significantly improved external quantum efficiency compared with the comparative compounds (Ref-1 to 3).

[1200] Compounds Inv-1 to Inv-18 synthesized in Synthesis Examples 1 to 18

[1201] [Chemical formula 254]

[1202]

[1203] [Chemical formula 255]

[1204]

[1205] Intermediate Synthesis Example 1: Synthesis of Intermediate A

[1206] [Chemical Formula 256]

[1207]

[1208] Under an argon atmosphere, a mixture of 4-bromo-9-phenyl-9H-carbazole (12.89 g, 40.0 mmol) synthesized in the same manner as the method described in Dyes and Pigments, 156, 369 - 378; 2018, 3-chlorophenylboronic acid (7.51 g, 48.0 mmol), bis(triphenylphosphine)palladium(II) dichloride (1.40 g, 2 mmol), potassium carbonate (16.58 g, 120 mmol), dimethoxyethane (DME) (200 mL), and water (60 mL) was stirred at 80 °C for 5 hours. The reaction solution was cooled to room temperature, water was added, and then filtration was carried out. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (11.32 g). The yield was 80%.

[1209] Intermediate Synthesis Example 2: Synthesis of Intermediate B

[1210] [Chemical Formula 257]

[1211]

[1212] Under an argon atmosphere, a mixture of [1,1'-biphenyl]-2-amine (5.08 g, 30.0 mmol), 2-(4-bromophenyl)phenanthrene (6.66 g, 20.0 mmol) synthesized in the same manner as the method described in International Publication No. WO2019 / 189033, tris(dibenzylideneacetone)dipalladium(0) (0.37 g, 0.4 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene (BINAP) (0.50 g, 0.8 mmol), sodium tert-butoxide (2.88 g, 30 mmol), and toluene (150 mL) was stirred at 100 °C for 5 hours. The reaction solution was cooled to room temperature, water was added, and then filtration was carried out. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (5.9 g). The yield was 70%.

[1213] Intermediate Synthesis Example 3: Synthesis of Intermediate D

[1214] [Chemical Formula 258]

[1215]

[1216] Under an argon atmosphere, a mixture of 4-bromo-9H-carbazole (7.38 g, 30.0 mmol), iodobenzene-d5 (7.53 g, 36.0 mmol), copper(I) iodide (0.29 g, 1.5 mmol), tripotassium phosphate (19.1 g, 90 mmol), 1,2-cyclohexanediamine (0.17 g, 1.5 mmol), and 1,4-dioxane (100 mL) was stirred at 100 °C for 7 hours. The reaction solution was cooled to room temperature, water was added, and then filtration was carried out. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (7.36 g). The yield was 75%. In addition, a mixture of the obtained intermediate C (7.36 g, 22.5 mmol), 3-chlorophenylboronic acid (4.22 g, 27.0 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.79 g, 1.13 mmol), potassium carbonate (9.33 g, 67.5 mmol), DME (150 mL), and water (34 mL) was stirred at 80 °C for 5 hours. The reaction solution was cooled to room temperature, water was added, and then filtration was carried out. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (6.7 g). The yield was 83%.

[1217] Intermediate Synthesis Example 4: Synthesis of Intermediate E

[1218] [Chemical Formula 259]

[1219]

[1220] Using 2-iodonaphthalene in place of iodobenzene-d5 used in Intermediate Synthesis Example 3, and otherwise performing the same operations as in Intermediate Synthesis Example 3, Intermediate E was obtained.

[1221] Intermediate Synthesis Example 5: Synthesis of Intermediate F

[1222] [Chemical Formula 260]

[1223]

[1224] Under an argon atmosphere, a mixture of N-([1,1'-biphenyl]-4-yl)-[1,1':4',1''-terphenyl]-4-amine (5.96 g, 15.0 mmol), 1-bromo-3-iodobenzene (6.37 g, 22.5 mmol), copper(I) iodide (0.286 g, 1.5 mmol), sodium tert-butoxide (3.6 g, 37.5 mmol), and tetrahydrofuran (150 mL) was stirred at 60 °C for 12 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (5.8 g). The yield was 70%.

[1225] Intermediate Synthesis Example 6: Synthesis of Intermediate H

[1226] [Chemical Formula 261]

[1227]

[1228] Under an argon atmosphere, a mixture of 1-bromo-4-iodobenzene-2,3,5,6-d4 (2.0 g, 6.97 mmol) synthesized by operating in the same manner as the method described in International Publication No. 2011 / 040939, phenylboronic acid (0.850 g, 6.97 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.098 g, 0.139 mmol), potassium carbonate (2.89 g, 20.91 mmol), DME (35 mL), and water (10.5 mL) was stirred at 80 °C for 5 hours. The reaction solution was cooled to room temperature, water was added, and then filtration was carried out. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain Intermediate G as a white solid (1.49 g). The yield was 90%. Next, a mixture of the obtained Intermediate G (1.49 g, 6.28 mmol), 4-amino-p-terphenyl (1.54 g, 6.28 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.115 g, 0.126 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) (0.156 g, 0.251 mmol), sodium tert-butoxide (0.845 g, 8.79 mmol), and toluene (45 mL) was stirred at 100 °C for 5 hours. The reaction solution was cooled to room temperature, water was added, and then filtration was carried out. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain Intermediate H as a white solid (2.01 g). The yield was 80%.

[1229] Intermediate Synthesis Example 7: Synthesis of Intermediate I

[1230] [Chemical Formula 262]

[1231]

[1232] Under an argon atmosphere, a mixture of 4-bromo-9-phenyl-9H-carbazole (9.67 g, 30.0 mmol), 3-aminophenylboronic acid monohydrate (5.58 g, 36.0 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.632 g, 0.9 mmol), potassium carbonate (12.44 g, 90 mmol), dimethoxyethane (DME) (150 mL), and water (45 mL) was stirred at 80 °C for 7 hours. The reaction solution was cooled to room temperature, water was added, and then filtration was carried out. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (10.03 g). The yield was 75%.

[1233] Synthesis Example 8 of Intermediate: Synthesis of Intermediate J

[1234] [Chemical Formula 263]

[1235]

[1236] Using 4-biphenylboronic acid to replace phenylboronic acid used in Intermediate Synthesis Example 6, and performing the same operations as in Intermediate Synthesis Example 6 otherwise, Intermediate J was obtained.

[1237] Synthesis Example 9 of Intermediate: Synthesis of Intermediate K

[1238] [Chemical Formula 264]

[1239]

[1240] Under an argon atmosphere, a mixture of Intermediate I (3 g, 8.97 mmol), Intermediate G (1.86 g, 5.26 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.246 g, 0.269 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) (0.335 g, 0.538 mmol), sodium tert-butoxide (1.207 g, 12.56 mmol), and toluene (90 mL) was stirred at 100 °C for 5 hours. After cooling the reaction solution to room temperature, it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (3.08 g). The yield was 70%.

[1241] Synthesis Example 10 of Intermediate: Synthesis of Intermediate L

[1242] [Chemical Formula 265]

[1243]

[1244] Using 4-bromobiphenyl to replace Intermediate G used in Intermediate Synthesis Example 9, and performing the same operations as in Intermediate Synthesis Example 9 otherwise, Intermediate L was obtained.

[1245] Synthesis Example 1: Synthesis of Compound Inv-1

[1246] [Chemical Formula 266]

[1247]

[1248] Under an argon atmosphere, a mixture of N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine (6.26 g, 15.75 mmol), intermediate A (5.31 g, 15.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.549 g, 0.60 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.545 g, 1.20 mmol), sodium tert-butoxide (2.02 g, 21.00 mmol) and xylene (100 mL) synthesized in the same manner as described in International Publication No. 2006 / 073059 was stirred at 140°C for 3.5 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (4.29 g). The yield was 40%.

[1249] The obtained substance was subjected to mass spectrometry analysis (m / e=714, relative to molecular weight 714.30). It was found to be compound Inv-1.

[1250] Synthesis Example 2: Synthesis of Compound Inv-2

[1251] [Chemical formula 267]

[1252]

[1253] Under an argon atmosphere, the same operation as in Synthesis Example 1 was performed, except that di([1,1'-biphenyl]-4-yl)amine synthesized by the same operation as the method described in International Publication No. 2006 / 073059 was used instead of N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine used in Synthesis Example 1 to obtain a white solid.

[1254] The obtained substance was subjected to mass spectrometry analysis (m / e=638 relative to molecular weight 638.27), indicating that it was compound Inv-2.

[1255] Synthesis Example 3: Synthesis of Compound Inv-3

[1256] [Chemical formula 268]

[1257]

[1258] Under an argon atmosphere, the same operations as in Synthesis Example 1 were performed, except that N-(4-(naphthalene-1-yl)phenyl)-[1,1'-biphenyl]-4-amine synthesized in the same manner as described in International Publication No. 2006 / 073059 was used instead of N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine used in Synthesis Example 1 to obtain a white solid.

[1259] The result of mass spectrometry of the obtained substance (m / e = 688 relative to molecular weight 688.29) was Compound Inv-3.

[1260] Synthesis Example 4: Synthesis of Compound Inv-4

[1261] [Chemical formula 269]

[1262]

[1263] Under an argon atmosphere, bis(4-(naphthalen-1-yl)phenyl)amine synthesized by the same operation as the method described in International Publication No. 2006 / 073059 was used instead of N-([1,1'-biphenyl]-4-yl)-[1,1':4',1''-terphenyl]-4-amine used in Synthesis Example 1, and otherwise, the same operations as in Synthesis Example 1 were carried out to obtain a white solid.

[1264] The result of mass spectrometry of the obtained substance (m / e = 790 relative to molecular weight 738.30) was Compound Inv-4.

[1265] Synthesis Example 5: Synthesis of Compound Inv-5

[1266] [Chemical formula 270]

[1267]

[1268] Under an argon atmosphere, N-([1,1'-biphenyl]-2-yl)-[1,1':4',1''-terphenyl]-4-amine synthesized by the same operation as the method described in International Publication No. 2015 / 053403 was used instead of N-([1,1'-biphenyl]-4-yl)-[1,1':4',1''-terphenyl]-4-amine used in Synthesis Example 1, and otherwise, the same operations as in Synthesis Example 1 were carried out to obtain a white solid.

[1269] The result of mass spectrometry of the obtained substance (m / e = 714 relative to molecular weight 714.30) was Compound Inv-5.

[1270] Synthesis Example 6: Synthesis of Compound Inv-6

[1271] [Chemical formula 271]

[1272]

[1273] Under an argon atmosphere, N-(4-(phenanthren-2-yl)phenyl)-[1,1'-biphenyl]-4-amine synthesized by operating in the same manner as the method described in International Publication No. 2018 / 038544 was used in place of N-([1,1'-biphenyl]-4-yl)-[1,1':4',1''-terphenyl]-4-amine used in Synthesis Example 1. Otherwise, the same operations as in Synthesis Example 1 were carried out to obtain a white solid.

[1274] As a result of subjecting the obtained substance to mass spectrometry (m / e = 738 relative to a molecular weight of 738.30), it was Compound Inv-6.

[1275] Synthesis Example 7: Synthesis of Compound Inv-7

[1276] [Chemical formula 272]

[1277]

[1278] Under an argon atmosphere, N-([1,1'-biphenyl]-4-yl)-4'-(naphthalen-1-yl)-[1,1'-biphenyl]-4-amine synthesized by operating in the same manner as the method described in International Publication No. 2006 / 073059 was used in place of N-([1,1'-biphenyl]-4-yl)-[1,1':4',1''-terphenyl]-4-amine used in Synthesis Example 1. Otherwise, the same operations as in Synthesis Example 1 were carried out to obtain a white solid.

[1279] As a result of subjecting the obtained substance to mass spectrometry (m / e = 764 relative to a molecular weight of 764.32), it was Compound Inv-7.

[1280] Synthesis Example 8: Synthesis of Compound Inv-8

[1281] [Chemical formula 273]

[1282]

[1283] Under an argon atmosphere, Intermediate B was used in place of N-([1,1'-biphenyl]-4-yl)-[1,1':4',1''-terphenyl]-4-amine used in Synthesis Example 1. Otherwise, the same operations as in Synthesis Example 1 were carried out to obtain a white solid.

[1284] As a result of subjecting the obtained substance to mass spectrometry (m / e = 738 relative to a molecular weight of 738.30), it was Compound Inv-8.

[1285] Synthesis Example 9: Synthesis of Compound Inv-9

[1286] [Chemical formula 274]

[1287]

[1288] Under an argon atmosphere, using intermediate D in place of intermediate A used in Synthesis Example 2, the same operations as in Synthesis Example 2 were carried out to obtain a white solid.

[1289] As a result of subjecting the obtained substance to mass spectrometry (m / e = 643 relative to a molecular weight of 643.30), it was Compound Inv-9.

[1290] Synthesis Example 10: Synthesis of Compound Inv-10

[1291] [Chemical formula 275]

[1292]

[1293] Under an argon atmosphere, using intermediate E in place of intermediate A used in Synthesis Example 1, otherwise, the same operations as in Synthesis Example 1 were carried out to obtain a white solid.

[1294] As a result of subjecting the obtained substance to mass spectrometry (m / e = 764 relative to a molecular weight of 764.32), it was Compound Inv-10.

[1295] Synthesis Example 11: Synthesis of Compound Inv-11

[1296] [Chemical formula 276]

[1297]

[1298] Under an argon atmosphere, a mixture of intermediate F (5.8 g, 10.5 mmol) and tetrahydrofuran (105 mL) was cooled to -78 °C, and then a hexane solution of n-butyllithium (6.56 mL, 10.5 mmol) was added dropwise. The resulting mixture was stirred at -78 °C for 1 hour. Further, a tetrahydrofuran solution of zinc chloride (25.2 mL, 12.6 mmol) was added dropwise to the reaction solution, and the resulting mixture was stirred at 0 °C for 1 hour. Intermediate A (4.46 g, 12.6 mmol) and [1,1'-bis(diphenylphosphino)ferrocene] dichloropalladium(II) dichloromethane adduct (0.429 g, 0.525 mmol) were added to the reaction solution, and the mixture was stirred at 60 °C for 6 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (2.49 g). The yield was 30%.

[1299] As a result of subjecting the obtained substance to mass spectrometry (m / e = 790 relative to a molecular weight of 790.33), it was Compound Inv-11.

[1300] Synthesis Example 12: Synthesis of Compound Inv-12

[1301] [Chemical formula 277]

[1302]

[1303] Under an argon atmosphere, a mixture of N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-2-amine (5 g, 12.58 mmol), intermediate A (4.67 g, 13.2 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.230 g, 0.252 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.292 g, 1.01 mmol), sodium tert-butoxide (1.69 g, 17.6 mmol), and xylene (84 mL) synthesized in the same manner as described in International Publication No. 2014 / 203541 was stirred at 140°C for 7 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (4.05 g). The yield was 45%.

[1304] The obtained substance was subjected to mass spectrometry analysis (m / e=714, relative to molecular weight 714.30). It was found to be compound Inv-12.

[1305] Synthesis Example 13: Synthesis of Compound Inv-13

[1306] [Chemical formula 278]

[1307]

[1308] Under argon atmosphere, a mixture of N-(4-(naphthalene-1-yl)phenyl)naphthalene-1-amine (5g, 14.47mmol), intermediate A (5.38g, 15.20mmol), tris(dibenzylideneacetone)dipalladium (0) (0.265g, 0.289mmol), tri-tert-butylphosphonium tetrafluoroborate (0.336g, 1.158mmol), sodium tert-butoxide (1.947g, 20.26mmol), and xylene (96mL) synthesized by the same operation as described in Japanese Patent Application Laid-Open No. 20160-74625 was stirred at 140°C for 7 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (5.76g). The yield was 60%.

[1309] The obtained substance was subjected to mass spectrometry analysis (m / e=662, relative molecular weight 662.27). It was found to be compound Inv-13.

[1310] Synthesis Example 14: Synthesis of Compound Inv-14

[1311] [Chemical formula 279]

[1312]

[1313] Under argon atmosphere, a mixture of N-(4-(naphthalene-1-yl)phenyl)naphthalene-1-amine (5g, 14.47mmol), intermediate E (6.14g, 15.20mmol), tris(dibenzylideneacetone)dipalladium (0) (0.265g, 0.289mmol), tri-tert-butylphosphonium tetrafluoroborate (0.336g, 1.158mmol), sodium tert-butoxide (1.947g, 20.26mmol), and xylene (96mL) synthesized by the same operation as described in Japanese Patent Laid-Open No. 2016-074625 was stirred at 140°C for 7 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (4.13g). The yield was 40%.

[1314] The obtained substance was subjected to mass spectrometry analysis (m / e=712, relative molecular weight 712.29). It was found to be compound Inv-14.

[1315] Synthesis Example 15: Synthesis of Compound Inv-15

[1316] [Chemical formula 280]

[1317]

[1318] Under argon atmosphere, a mixture of N-([1,1'-biphenyl]-4-yl)-[1,1':4',1'-terphenyl]-4-amine (5 g, 12.58 mmol), intermediate D (4.74 g, 13.21 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.230 g, 0.252 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.292 g, 1.00 mmol), sodium tert-butoxide (1.69 g, 17.6 mmol), and xylene (84 mL) synthesized by the same method as described in International Publication No. 2006 / 073059 was stirred at 140° C. for 4 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (6.34 g). The yield was 70%.

[1319] The obtained substance was subjected to mass spectrometry analysis (m / e=719, relative molecular weight 719.33). The substance was identified as compound Inv-15.

[1320] Synthesis Example 16: Synthesis of Compound Inv-16

[1321] [Chemical formula 281]

[1322]

[1323] Under argon atmosphere, a mixture of intermediate H (2.01 g, 5.01 mmol), intermediate A (1.86 g, 5.26 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.092 g, 0.100 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.116 g, 0.400 mmol), sodium tert-butoxide (0.673 g, 7.01 mmol), and xylene (33 mL) was stirred at 140° C. for 4 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (2.34 g). The yield was 65%.

[1324] The obtained substance was subjected to mass spectrometry analysis (m / e=718, relative molecular weight 718.33). The substance was identified as compound Inv-16.

[1325] Synthesis Example 17: Synthesis of Compound Inv-17

[1326] [Chemical formula 282]

[1327]

[1328] Under argon atmosphere, a mixture of intermediate K (3.08 g, 6.28 mmol), intermediate J (2.065 g, 6.59 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.230 g, 0.251 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.146 g, 0.502 mmol), sodium tert-butoxide (0.845 g, 8.79 mmol), and toluene (42 mL) was stirred at 100 ° C for 5 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (2.04 g). The yield was 45%.

[1329] The obtained substance was subjected to mass spectrometry analysis (m / e=722, relative to molecular weight 722.35). It was found to be compound Inv-17.

[1330] Synthesis Example 18: Synthesis of Compound Inv-18

[1331] [Chemical formula 283]

[1332]

[1333] Under an argon atmosphere, in Synthesis Example 17, intermediate L was used instead of intermediate K, and otherwise, the same operations as in Synthesis Example 17 were carried out to obtain a white solid. As a result of subjecting the obtained substance to mass spectrometry (m / e = 718 relative to a molecular weight of 718.33), the compound was Inv-18.

[1334] Explanation of Reference Numerals

[1335] 1, 11: Organic EL element

[1336] 2: Substrate

[1337] 3: Anode

[1338] 4: Cathode

[1339] 5: Light-emitting layer

[1340] 6: Hole transport region (hole transport layer)

[1341] 6a: Hole injection layer

[1342] 6b: First hole transport layer

[1343] 6c: Second hole transport layer

[1344] 7: Electron transport region (electron transport layer)

[1345] 7a: First electron transport layer

[1346] 7b: Second electron transport layer

[1347] 10, 20: Light-emitting unit

Claims

1. A compound represented by the following formula (1), In formula (1), Ar 1 and Ar 2 each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted phenanthryl, Ar 3 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted 1-naphthyl group, or a substituted or unsubstituted 2-naphthyl group, L 1 and L 2 each independently represents a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, R 1 ~R 7 is a hydrogen atom, n is 0, The Ar 1 、the Ar 2 、the L 1 and the L 2 in the "substituted or unsubstituted" cases, the substituents are each independently selected from unsubstituted alkyl groups having 1 to 6 carbon atoms, unsubstituted cycloalkyl groups having 3 to 6 ring carbon atoms, unsubstituted phenyl groups, unsubstituted biphenyl groups, unsubstituted terphenyl groups, unsubstituted naphthyl groups, and unsubstituted phenanthryl groups. The said Ar 3 in the said "substituted or unsubstituted" case, the substituents are selected from unsubstituted alkyl groups having 1 to 6 carbon atoms, unsubstituted cycloalkyl groups having 3 to 6 ring carbon atoms, unsubstituted phenyl groups, unsubstituted biphenyl groups, unsubstituted terphenyl groups, unsubstituted naphthyl groups, and unsubstituted phenanthryl groups. It should be noted that the hydrogen atoms contained in the compound include the meanings of protium, deuterium, and tritium.

2. The compound according to claim 1, wherein, Ar 1 and Ar 2 each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted p - terphenyl, substituted or unsubstituted o - terphenyl, and substituted or unsubstituted p - quaterphenyl - 4 - yl.

3. The compound according to claim 1, wherein, In the substituted or unsubstituted biphenyl, the biphenyl is p-biphenyl, m-biphenyl, or o-biphenyl.

4. The compound according to claim 1, wherein, In the substituted or unsubstituted biphenyl, the biphenyl is p-biphenyl or o-biphenyl.

5. The compound according to claim 1, wherein, In the substituted or unsubstituted terphenyl, the terphenyl is p-terphenyl-4-yl, p-terphenyl-3-yl, or p-terphenyl-2-yl.

6. The compound according to claim 1, wherein, In the substituted or unsubstituted terphenyl, the terphenyl is p-terphenyl-4-yl.

7. The compound according to claim 1, wherein, In the substituted or unsubstituted naphthyl, the naphthyl is 1-naphthyl or 2-naphthyl.

8. The compound according to claim 1, wherein, In the substituted or unsubstituted phenanthryl, the phenanthryl is 2-phenanthryl or 9-phenanthryl.

9. The compound according to claim 1, wherein, Ar 3 is an unsubstituted phenyl, an unsubstituted 1-naphthyl or an unsubstituted 2-naphthyl.

10. The compound according to claim 1, wherein, Ar 3 is an unsubstituted phenyl group.

11. The compound according to claim 1, wherein, L 1 and L 2 each independently represents a single bond, an unsubstituted phenylene group, or an unsubstituted biphenylene group.

12. The compound according to claim 1, wherein, L 1 and L 2 each independently represents a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

13. The compound according to claim 1, wherein, L 1 and L 2 is a single bond.

14. The compound according to any one of claims 1 to 13, wherein, The substituents in the "substituted or unsubstituted" case are selected from unsubstituted alkyl groups having 1 to 6 carbon atoms, unsubstituted phenyl groups, unsubstituted biphenyl groups, unsubstituted terphenyl groups, unsubstituted naphthyl groups, and unsubstituted phenanthryl groups.

15. The compound according to any one of claims 1 to 13, wherein, The substituents in the "substituted or unsubstituted" case are selected from unsubstituted alkyl groups having 1 to 6 carbon atoms and unsubstituted cycloalkyl groups having 3 to 6 ring carbon atoms.

16. The compound according to any one of claims 1 to 13, wherein, The "substituted or unsubstituted" case is unsubstituted.

17. The compound according to any one of claims 1 to 13, wherein, The compound has at least 1 deuterium atom.

18. The compound according to any one of claims 1 to 8 and 11 to 13, wherein, The said Ar 3 In the said substituted or unsubstituted phenyl group, the phenyl group contains at least 1 deuterium atom.

19. A compound, which is any one of the following, 。 20. A compound, which is any one of the following, 。 21. A material for an organic electroluminescent element, which comprises the compound according to any one of claims 1 to 20.

22. An organic electroluminescent element, which has a cathode, an anode, and an organic layer located between the cathode and the anode, the organic layer includes a light-emitting layer, and at least 1 layer of the organic layer contains the compound according to any one of claims 1 to 20.

23. The organic electroluminescent element according to claim 22, wherein, The organic layer includes a hole transport region between the anode and the light-emitting layer, and the hole transport region contains the compound.

24. The organic electroluminescent device according to claim 23, wherein, the hole transport region includes a first hole transport layer on the anode side and a second hole transport layer on the cathode side, and the first hole transport layer, the second hole transport layer, or both the first hole transport layer and the second hole transport layer contain the compound.

25. The organic electroluminescent device according to claim 24, wherein, the second hole transport layer contains the compound.

26. The organic electroluminescent device according to claim 24, wherein, the second hole transport layer is adjacent to the light-emitting layer.

27. The organic electroluminescent device according to any one of claims 22 to 26, wherein, the light-emitting layer contains a fluorescent dopant.

28. The organic electroluminescent device according to any one of claims 22 to 26, wherein, the light-emitting layer contains a phosphorescent dopant.

29. An electronic device comprising the organic electroluminescent device according to any one of claims 22 to 28.

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