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

Abstract

The present application relates to a compound, a material for an organic electroluminescent element, an organic electroluminescent element, and an electronic device. Provided are a compound represented by formula (1), an organic electroluminescent element comprising the compound, and an electronic device comprising the organic electroluminescent element. The symbols in the formula are as defined in the specification. # imgabs0 #

Description

[0001] This application is a divisional application of the application with the filing date of March 29, 2021, the application number of 202180004849.4, and the invention title of "Compound, Material for Organic Electroluminescent Element, Organic Electroluminescent Element, and Electronic Device". Technical Field

[0002] 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

[0003] 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.

[0004] Patent Documents 1 to 13 disclose compounds used as materials for organic electroluminescent elements.

[0005] Prior Art Documents

[0006] Patent Documents

[0007] Patent Document 1: KR2018-0082124A

[0008] Patent Document 2: US2015 / 0236267A1

[0009] Patent Document 3: WO2009 / 145016A1

[0010] Patent Document 4: CN109485577A

[0011] Patent Document 5: KR2019-0003329A

[0012] Patent Document 6: KR2017-0088313A

[0013] Patent Document 7: WO2019 / 206292A1

[0014] Patent Document 8: WO2019 / 185060A1

[0015] Patent Document 9: US2019 / 0140177A1

[0016] Patent Document 10: WO2019 / 168367A1

[0017] Patent Document 11: US2019 / 0165273A1

[0018] Patent Document 12: WO2012 / 079678A1

[0019] Patent Document 13: WO2020004235A1 Summary of the Invention

[0020] Problems to be Solved by the Invention

[0021] 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.

[0022] 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.

[0023] Means for Solving the Problems

[0024] The present inventors have repeatedly and intensively studied the performance of organic EL elements containing the compounds described in the above patent documents and other compounds, and as a result, have found that a monoamine represented by the following formula (1) provides an organic EL element with further improved element performance.

[0025] In one aspect, the present invention provides a compound represented by the following formula (1).

[0026] [Chemical Formula 1]

[0027]

[0028] (In the formula,

[0029] Ar 1 and Ar 2 are each independently a group represented by any of formulas (10) to (14).

[0030] [Chemical Formula 2]

[0031] [[ID=5T]]

[0032] (In the formula,

[0033] R 11 ~R 15 、R 21 ~R 26 、R 41 ~R 48 、R 51~R 62 and R 71 ~R 78 Each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a halogen atom, a cyano group, a nitro group, 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.

[0034] R 31 ~R 35 Each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0035] X is an oxygen atom, a sulfur atom or NR 81 ,

[0036] R 81 is a hydrogen atom, 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.

[0037] Among them,

[0038] One selected from R 11 ~R 15 is a single bond bonded to *c,

[0039] One selected from R 21 ~R 26 is a single bond bonded to *d, and one selected from R 21 ~R 26 is a single bond bonded to *e,

[0040] One selected from R 45 ~R 48 is a single bond bonded to *f,

[0041] One selected from R 59 ~R 62 is a single bond bonded to *g,

[0042] One selected from R 75 ~R 78 and R 81 is a single bond bonded to *i,

[0043] *h is bonded to one selected from carbon atoms *4 to *8,

[0044] ** represents the bonding position to the central nitrogen atom,

[0045] m is 0 or 1, n is 0 or 1,

[0046] In Formulas (10) to (12) and (14), when m is 0 and n is 0, *e is bonded to the central nitrogen atom; when m is 0 and n is 1, *c is bonded to the central nitrogen atom; when m is 1 and n is 0, *e is bonded to one selected from R 11 ~R 15 ;

[0047] In Formula (13), when m is 0 and n is 1, *c is bonded to the central nitrogen atom; when m is 1 and n is 0, *e is bonded to one selected from R 11 ~R 15 ; excluding the case where m is 0 and n is 0,

[0048] In Formula (14), when m is 0 and n is 1, and when m is 1 and n is 0, one selected from R 75 ~R 78 is a single bond bonded to *i,

[0049] Two adjacent ones selected from R 11 ~R 15 that are not the above single bond, two adjacent ones selected from R 21 ~R 26 that are not the above single bond, two adjacent ones selected from R 31 ~R 35 that are not the above single bond, two adjacent ones selected from R 41 ~R 48 that are not the above single bond, two adjacent ones selected from R 51 ~R 62 that are not the above single bond, and two adjacent ones selected from R 71 ~R 78 that are not the above single bond do not bond to each other, and thus do not form a ring structure,

[0050] Benzene ring A and benzene ring B, benzene ring A and benzene ring C, benzene ring B and benzene ring C, benzene ring A and naphthalene ring, and benzene ring B and naphthalene ring are not crosslinked.

[0051] *a is bonded to one selected from carbon atoms *1 to *3.

[0052] R 1 ~R 4 are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0053] Among them,

[0054] One selected from R 1 ~R 4 is a single bond bonded to *b,

[0055] R selected from single bonds other than those bonded to *b 1 ~R 4 Two adjacent ones among them are not bonded to each other, and thus no ring structure is formed.

[0056] R 5 ~R 9 Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted phenyl group.

[0057] Among them,

[0058] Two adjacent ones selected from R 5 ~R 9 can be independently bonded to each other to form a substituted or unsubstituted ring structure, or can be not bonded to each other, and thus no ring structure is formed. )

[0059] In another aspect, the present invention provides a material for an organic EL element containing the compound represented by the above formula (1).

[0060] In yet another aspect, the present invention provides an organic electroluminescent element including an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer including a light-emitting layer, and at least one layer of the organic layer containing the compound represented by the above formula (1).

[0061] In yet another aspect, the present invention provides an electronic device including the above organic electroluminescent element.

[0062] Advantages of the Invention

[0063] The organic EL element containing the compound represented by the above formula (1) exhibits improved element performance. BRIEF DESCRIPTION OF THE DRAWINGS

[0064] 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.

[0065] 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

[0066] [Definitions]

[0067] In this specification, the hydrogen atom includes isotopes having different numbers of neutrons, namely protium, deuterium, and tritium.

[0068] In this specification, in a chemical structural formula, when the bondable positions of symbols such as "R" and "D" representing deuterium atoms are not explicitly shown, a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom, is bonded.

[0069] In this specification, the number of ring-forming carbon atoms refers to the number of carbon atoms among the atoms constituting the ring itself in a compound 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. For the "number of ring-forming carbon atoms" described below, the same applies unless otherwise specified. For example, the number of ring-forming carbon atoms of a benzene ring is 6, the number of ring-forming carbon atoms of a naphthalene ring is 10, the number of ring-forming carbon atoms of a pyridine ring is 5, and the number of ring-forming carbon atoms of a furan ring is 4. In addition, for example, the number of ring-forming carbon atoms of 9,9-diphenylfluorenyl is 13, and the number of ring-forming carbon atoms of 9,9'-spirobifluorenyl is 25.

[0070] In addition, when an alkyl group, for example, is substituted on a benzene ring as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring-forming carbon atoms of the benzene ring. Therefore, the number of ring-forming carbon atoms of a benzene ring substituted with an alkyl group is 6. In addition, when an alkyl group, for example, is substituted on a naphthalene ring as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring-forming carbon atoms of the naphthalene ring. Therefore, the number of ring-forming carbon atoms of a naphthalene ring substituted with an alkyl group is 10.

[0071] In this specification, the number of ring-forming atoms refers to 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. For the "number of ring-forming atoms" described below, the same applies unless otherwise specified. For example, the number of ring-forming atoms of a pyridine ring is 6, the number of ring-forming atoms of a quinazoline ring is 10, and the number of ring-forming atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or the number of atoms constituting a substituent is not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms of a pyridine ring bonded with a hydrogen atom or a substituent is 6. In addition, for example, the number of hydrogen atoms bonded to a carbon atom of a quinazoline ring or atoms constituting a substituent are not included in the number of ring-forming atoms of the quinazoline ring. Therefore, the number of ring-forming atoms of a quinazoline ring bonded with a hydrogen atom or a substituent is 10.

[0072] In this specification, in the expression "ZZ group having a carbon number of XX to YY, which may be substituted or unsubstituted", "carbon number of XX to YY" represents the carbon number when the ZZ group is unsubstituted, and does not include the carbon number of the substituent 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.

[0073] In this specification, in the expression "ZZ group having XX to YY atoms, which may or may not be substituted", the "XX to YY atoms" indicates the number of atoms of the ZZ group when it is unsubstituted, and does not include the atoms of the substituent 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.

[0074] In this specification, an unsubstituted ZZ group means the case where the "ZZ group which may or may not be substituted" is an "unsubstituted ZZ group", and a substituted ZZ group means the case where the "ZZ group which may or may not be substituted" is a "substituted ZZ group".

[0075] In this specification, "unsubstituted" in the expression "ZZ group which may or may not be substituted" means that the hydrogen atom in the ZZ group is not replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom or a tritium atom.

[0076] In addition, in this specification, "substituted" in the expression "ZZ group which may or may not be substituted" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. Similarly, "substituted" in the expression "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group are replaced by the AA group.

[0077] "Substituents described in this specification"

[0078] Hereinafter, the substituents described in this specification will be described. Unless otherwise specified, each substituent described in this specification is defined as follows.

[0079] The number of ring-forming carbon atoms of the "unsubstituted aryl" described in this specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified in this specification.

[0080] The number of ring-forming atoms of the "unsubstituted heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified in this specification.

[0081] The number of carbon atoms of the "unsubstituted alkyl" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified in this specification.

[0082] 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.

[0083] The carbon number 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.

[0084] The ring-forming carbon number 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.

[0085] The ring-forming carbon number 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.

[0086] The ring-forming atom number 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.

[0087] The carbon number 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.

[0088] - "substituted or unsubstituted aryl"

[0089] As specific examples (specific example group G1) of the "substituted or unsubstituted aryl" described in this specification, the following unsubstituted aryls (specific example group G1A) and substituted aryls (specific example group G1B) etc. can be cited. (Here, the unsubstituted aryl means the case where the "substituted or unsubstituted aryl" is an "unsubstituted aryl", and the substituted aryl means the case where the "substituted or unsubstituted aryl" is a "substituted aryl".) In this invention book, when only "aryl" is indicated, it includes both "unsubstituted aryl" and "substituted aryl".

[0090] "Substituted aryl" means a group in which one or more hydrogen atoms of the "unsubstituted aryl" are replaced by substituents. As the "substituted aryl", examples 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 the "unsubstituted aryl" and the examples of the "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" in 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" in the following specific example group G1B are further replaced by substituents.

[0091] - Unsubstituted aryl (specific example group G1A):

[0092] phenyl

[0093] p - terphenyl - 4 - yl

[0094] m - terphenyl - 4 - yl

[0095] o - terphenyl - 4 - yl

[0096] p - terphenyl - 4 - yl

[0097] p - terphenyl - 3 - yl

[0098] p - terphenyl - 2 - yl

[0099] m - terphenyl - 4 - yl

[0100] m - terphenyl - 3 - yl

[0101] m - terphenyl - 2 - yl

[0102] m - terphenyl - 3’ - yl

[0103] o - terphenyl - 4 - yl

[0104] o - terphenyl - 3 - yl

[0105] o - terphenyl - 2 - yl

[0106] 1 - naphthyl

[0107] 2 - naphthyl

[0108] anthryl

[0109] benzanthryl

[0110] phenanthryl

[0111] benzophenanthryl

[0112] phenalenyl

[0113] pyrenyl

[0114] chrysenyl

[0115] benzchrysenyl

[0116] triphenylenyl

[0117] benzotriphenylenyl

[0118] tetracenyl

[0119] pentacenyl

[0120] fluorenyl

[0121] 9,9’ - spirobifluorenyl

[0122] benzofluorenyl

[0123] Dibenzofluorenyl,

[0124] Fluorenyl,

[0125] Benzo[a]fluorenyl,

[0126] Peryleneyl, and

[0127] 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).

[0128] [Chemical formula 3]

[0129]

[0130] [Chemical formula 4]

[0131]

[0132] ・Substituted aryl group (specific example group G1B):

[0133] o-Tolyl,

[0134] m-Tolyl,

[0135] p-Tolyl,

[0136] p-Xylyl,

[0137] m-Xylyl,

[0138] o-Xylyl,

[0139] p-Isopropylphenyl,

[0140] m-Isopropylphenyl,

[0141] o-Isopropylphenyl,

[0142] p-tert-Butylphenyl,

[0143] m-tert-Butylphenyl,

[0144] o-tert-Butylphenyl,

[0145] 3,4,5-Trimethylphenyl,

[0146] 9,9-Dimethylfluorenyl,

[0147] 9,9-Diphenylfluorenyl

[0148] 9,9-Bis(4-methylphenyl)fluorenyl,

[0149] 9,9-Bis(4-isopropylphenyl)fluorenyl,

[0150] 9,9-Bis(4-tert-butylphenyl)fluorenyl,

[0151] cyanophenyl,

[0152] triphenylsilylphenyl,

[0153] trimethylsilylphenyl,

[0154] phenylnaphthyl,

[0155] naphthylphenyl, and

[0156] a group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by the above general formulas (TEMP-1) to (TEMP-15) are replaced with substituents.

[0157] ・"substituted or unsubstituted heterocyclic group"

[0158] 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.

[0159] The "heterocyclic group" described in this specification is a monocyclic group or a fused-ring group.

[0160] The "heterocyclic group" described in this specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0161] 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 invention book, when only expressed as "heterocyclic group", it includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".

[0162] The "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of the "unsubstituted heterocyclic group" are replaced with substituents. Specific examples of the "substituted heterocyclic group" can include groups in which 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 hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself in the "substituted heterocyclic group" in specific example group G2B are further replaced with substituents, and groups in which hydrogen atoms of the substituents in the "substituted heterocyclic group" in specific example group G2B are further replaced with substituents.

[0163] The 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).

[0164] The 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).

[0165] - Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1):

[0166] Pyrrolyl,

[0167] Imidazolyl,

[0168] Pyrazolyl,

[0169] Triazolyl,

[0170] Tetrazolyl,

[0171] Oxazolyl,

[0172] Isoxazolyl,

[0173] Oxadiazolyl,

[0174] Thiazolyl,

[0175] Isothiazolyl,

[0176] Thiadiazolyl,

[0177] Pyridyl,

[0178] Pyridazinyl,

[0179] Pyrimidinyl,

[0180] Pyrazinyl,

[0181] Triazinyl,

[0182] Indolyl,

[0183] Isoindolyl,

[0184] Indazolyl,

[0185] Quinolizinyl,

[0186] quinolyl,

[0187] isoquinolyl,

[0188] cinnolinyl,

[0189] phthalazinyl,

[0190] quinazolinyl,

[0191] quinoxalinyl,

[0192] benzimidazolyl,

[0193] indazolyl,

[0194] phenanthrolinyl,

[0195] phenanthridinyl,

[0196] acridinyl,

[0197] phenazinyl,

[0198] carbazolyl,

[0199] benzocarbazolyl,

[0200] morpholinyl,

[0201] phenoxazinyl,

[0202] phenothiazinyl,

[0203] azacarbazolyl, and diazacarbazolyl.

[0204] ・Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2):

[0205] furyl,

[0206] oxazolyl,

[0207] isoxazolyl,

[0208] oxadiazolyl,

[0209] xanthenyl,

[0210] benzofuryl,

[0211] isobenzofuryl,

[0212] dibenzofuryl,

[0213] naphthobenzofuryl,

[0214] benzoxazolyl,

[0215] benzoisoxazolyl,

[0216] phenoxazinyl,

[0217] morpholinyl,

[0218] dinaphthofuranyl,

[0219] azadibenzofuranyl,

[0220] diazadibenzofuranyl,

[0221] azanaphthobenzofuranyl, and

[0222] diazanaphthobenzofuranyl.

[0223] ・Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3):

[0224] thienyl,

[0225] thiazolyl,

[0226] isothiazolyl,

[0227] thiadiazolyl,

[0228] benzothienyl,

[0229] isobenzothienyl,

[0230] dibenzothienyl,

[0231] naphthobenzothienyl,

[0232] benzothiazolyl,

[0233] benzoisothiazolyl,

[0234] phenothiazinyl,

[0235] dinaphthothienyl,

[0236] azadibenzothienyl,

[0237] diazadibenzothienyl,

[0238] azanaphthobenzothienyl, and

[0239] diazanaphthobenzothienyl.

[0240] ・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):

[0241] [Chemical formula 5]

[0242]

[0243] [Chemical formula 6]

[0244]

[0245] 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 CH2. Among them, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.

[0246] In the above general formulas (TEMP-16) to (TEMP-33), when at least one of X A and Y A is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the above general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0247] ・A substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):

[0248] (9-Phenyl)carbazolyl,

[0249] (9-Biphenyl)carbazolyl,

[0250] (9-Phenyl)phenylcarbazolyl,

[0251] (9-Naphthyl)carbazolyl,

[0252] Diphenylcarbazol-9-yl,

[0253] Phenylcarbazol-9-yl,

[0254] Methylbenzimidazolyl,

[0255] Ethylbenzimidazolyl,

[0256] Phenyltriazinyl,

[0257] Biphenyltriazinyl,

[0258] Diphenyltriazinyl,

[0259] Phenylquinazolinyl, and

[0260] Biphenylquinazolinyl

[0261] ・Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0262] Phenyldibenzofuranyl

[0263] Methyldibenzofuranyl

[0264] tert-Butyldibenzofuranyl, and

[0265] Monovalent residue of spiro[9H-xanthene-9,9’-[9H]fluorene]

[0266] ・Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

[0267] Phenyldibenzothiophenyl

[0268] Methyldibenzothiophenyl

[0269] tert-Butyldibenzothiophenyl, and

[0270] Monovalent residue of spiro[9H-thioxanthene-9,9’-[9H]fluorene]

[0271] ・Group in which one or more hydrogen atoms of the monovalent heterocyclic group derived from the ring structures represented by the above general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific example group G2B4):

[0272] The above "one or more hydrogen atoms of the monovalent heterocyclic group" means: 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 CH2.

[0273] ・"Substituted or unsubstituted alkyl"

[0274] 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 means the case where the "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and the substituted alkyl means the case where the "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when only expressed as "alkyl", it includes both "unsubstituted alkyl" and "substituted alkyl".

[0275] "Substituted alkyl" means a group in which one or more hydrogen atoms in "unsubstituted alkyl" are replaced by substituents. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl" (specific example group G3A) are replaced by substituents, examples of substituted alkyl (specific example group G3B), and the like. In this specification, the alkyl in "unsubstituted alkyl" refers to a chain-like alkyl. Therefore, "unsubstituted alkyl" includes "unsubstituted alkyl" that is straight-chain and "unsubstituted alkyl" that is branched-chain. It should be noted that the examples of "unsubstituted alkyl" and "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 specific example group G3B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted alkyl" of specific example group G3B are further replaced by substituents.

[0276] - Unsubstituted alkyl (specific example group G3A):

[0277] Methyl,

[0278] Ethyl,

[0279] n-Propyl,

[0280] Isopropyl,

[0281] n-Butyl,

[0282] Isobutyl,

[0283] sec-Butyl, and

[0284] tert-Butyl.

[0285] - Substituted alkyl (specific example group G3B):

[0286] Heptafluoropropyl (including isomers),

[0287] Pentafluoroethyl,

[0288] 2,2,2-Trifluoroethyl, and

[0289] Trifluoromethyl.

[0290] - "Substituted or unsubstituted alkenyl"

[0291] As a specific example (specific example group G4) of the "substituted or unsubstituted alkenyl" described in this specification, the following unsubstituted alkenyl (specific example group G4A), substituted alkenyl (specific example group G4B), etc. can be cited. (Here, the unsubstituted alkenyl refers to the case where the "substituted or unsubstituted alkenyl" is an "unsubstituted alkenyl", and the "substituted alkenyl" refers to the case where the "substituted or unsubstituted alkenyl" is a "substituted alkenyl".) In the present invention, when only "alkenyl" is expressed, it includes both "unsubstituted alkenyl" and "substituted alkenyl".

[0292] The "substituted alkenyl" refers to a group in which one or more hydrogen atoms in the "unsubstituted alkenyl" are replaced by substituents. As specific examples of the "substituted alkenyl", the following groups in which the "unsubstituted alkenyl" (specific example group G4A) has substituents, and 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 "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.

[0293] - Unsubstituted alkenyl (specific example group G4A):

[0294] Vinyl,[[]]

[0295] Allyl,[[]]

[0296] 1-Butenyl,[[]]

[0297] 2-Butenyl, and

[0298] 3-Butenyl.

[0299] - Substituted alkenyl (specific example group G4B):

[0300] 1,3-Butadienyl,[[]]

[0301] 1-Methylvinyl,[[]]

[0302] 1-Methylallyl,[[]]

[0303] 1,1-Dimethylallyl,[[]]

[0304] 2-Methylallyl, and

[0305] 1,2-Dimethylallyl.[[]]

[0306] - "Substituted or unsubstituted alkynyl"

[0307] As a specific example (specific example group G5) of the "substituted or unsubstituted alkynyl" described in this specification, the following unsubstituted alkynyl (specific example group G5A) etc. can be cited. (Here, the unsubstituted alkynyl means the case where the "substituted or unsubstituted alkynyl" is an "unsubstituted alkynyl".) Hereinafter, when only expressed as "alkynyl", it includes both "unsubstituted alkynyl" and "substituted alkynyl".

[0308] "Substituted alkynyl" means a group in which one or more hydrogen atoms in the "unsubstituted alkynyl" are replaced by substituents. As specific examples of the "substituted alkynyl", groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl" (specific example group G5A) are replaced by substituents etc. can be cited.

[0309] ・ Unsubstituted alkynyl (specific example group G5A):

[0310] Ethynyl

[0311] ・ "Substituted or unsubstituted cycloalkyl"

[0312] As specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl" described in this specification, the following unsubstituted cycloalkyl (specific example group G6A), substituted cycloalkyl (specific example group G6B) etc. can be cited. (Here, the unsubstituted cycloalkyl means the case where the "substituted or unsubstituted cycloalkyl" is an "unsubstituted cycloalkyl", and the substituted cycloalkyl means the case where the "substituted or unsubstituted cycloalkyl" is a "substituted cycloalkyl".) In this specification, when only expressed as "cycloalkyl", it includes both "unsubstituted cycloalkyl" and "substituted cycloalkyl".

[0313] "Substituted cycloalkyl" means a group in which one or more hydrogen atoms in the "unsubstituted cycloalkyl" are replaced by substituents. As specific examples of the "substituted cycloalkyl", groups in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl" (specific example group G6A) are replaced by substituents, and examples of substituted cycloalkyl (specific example group G6B) etc. can be cited. It should be noted that the examples of the "unsubstituted cycloalkyl" and the examples of the "substituted cycloalkyl" listed here are only for illustration, 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.

[0314] ・ Unsubstituted cycloalkyl (specific example group G6A):

[0315] Cyclopropyl,

[0316] Cyclobutyl,

[0317] Cyclopentyl,

[0318] Cyclohexyl,

[0319] 1 - Adamantyl,

[0320] 2 - Adamantyl,

[0321] 1 - Norbornyl, and

[0322] 2 - Norbornyl.

[0323] - Substituted cycloalkyl (specific example group G6B):

[0324] 4 - Methylcyclohexyl.

[0325] - “The group represented by -Si(R 901 )(R 902 )(R 903 )”

[0326] As specific examples (specific example group G7) of the group represented by -Si(R 901 )(R 902 )(R 903 ) described in this specification, there can be cited

[0327] -Si(G1)(G1)(G1),

[0328] -Si(G1)(G2)(G2),

[0329] -Si(G1)(G1)(G2),

[0330] -Si(G2)(G2)(G2),

[0331] -Si(G3)(G3)(G3), and

[0332] -Si(G6)(G6)(G6).

[0333] Here,

[0334] G1 is “substituted or unsubstituted aryl” described in specific example group G1.

[0335] G2 is “substituted or unsubstituted heterocyclic group” described in specific example group G2.

[0336] G3 is “substituted or unsubstituted alkyl” described in specific example group G3.

[0337] G6 is “substituted or unsubstituted cycloalkyl” described in specific example group G6.

[0338] Multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other.

[0339] - In -Si(G1)(G2)(G2), the plurality of G2s are the same as or different from each other.

[0340] - In -Si(G1)(G1)(G2), the plurality of G1s are the same as or different from each other.

[0341] - In -Si(G2)(G2)(G2), the plurality of G2s are the same as or different from each other.

[0342] - In -Si(G3)(G3)(G3), the plurality of G3s are the same as or different from each other.

[0343] - In -Si(G6)(G6)(G6), the plurality of G6s are the same as or different from each other.

[0344] ・ “-O-(R 904 ) group as shown”

[0345] As a specific example (specific example group G8) of the -O-(R 904 ) group as shown in this specification, there can be cited

[0346] -O(G1),

[0347] -O(G2),

[0348] -O(G3), and

[0349] -O(G6).

[0350] Here,

[0351] G1 is the “substituted or unsubstituted aryl” described in specific example group G1.

[0352] G2 is the “substituted or unsubstituted heterocyclic group” described in specific example group G2.

[0353] G3 is the “substituted or unsubstituted alkyl” described in specific example group G3.

[0354] G6 is the “substituted or unsubstituted cycloalkyl” described in specific example group G6.

[0355] ・ “-S-(R 905 ) group as shown”

[0356] As a specific example (specific example group G9) of the -S-(R 905 ) group as shown in this specification, there can be cited

[0357] -S(G1),

[0358] -S(G2),

[0359] -S(G3), and

[0360] -S(G6).

[0361] Herein,

[0362] G1 is the "substituted or unsubstituted aryl" described in Specific Example Group G1.

[0363] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0364] G3 is the "substituted or unsubstituted alkyl" described in Specific Example Group G3.

[0365] G6 is the "substituted or unsubstituted cycloalkyl" described in Specific Example Group G6.

[0366] ・The group represented by "-N(R 906 )(R 907 )"

[0367] 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

[0368] -N(G1)(G1),

[0369] -N(G2)(G2),

[0370] -N(G1)(G2),

[0371] -N(G3)(G3), and

[0372] -N(G6)(G6).

[0373] Herein,

[0374] G1 is the "substituted or unsubstituted aryl" described in Specific Example Group G1.

[0375] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0376] G3 is the "substituted or unsubstituted alkyl" described in Specific Example Group G3.

[0377] G6 is the "substituted or unsubstituted cycloalkyl" described in Specific Example Group G6.

[0378] The multiple G1s in -N(G1)(G1) are the same as or different from each other.

[0379] The multiple G2s in -N(G2)(G2) are the same as or different from each other.

[0380] The multiple G3s in -N(G3)(G3) are the same as or different from each other.

[0381] - The plurality of G6 in -N(G6)(G6) are the same as or different from each other

[0382] - "Halogen atom"

[0383] 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.

[0384] - "Substituted or unsubstituted fluoroalkyl"

[0385] 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" refers to a group in which one or more hydrogen atoms of the "fluoroalkyl" are replaced by substituents. It should be noted that the "substituted fluoroalkyl" described in this specification also includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the "substituted fluoroalkyl" are further replaced by substituents, and a group in which one or more hydrogen atoms of the substituents in the "substituted fluoroalkyl" are further replaced by substituents. As specific examples of the "unsubstituted fluoroalkyl", examples of groups in which one or more hydrogen atoms in the above-mentioned "alkyl" (specific example group G3) are replaced by fluorine atoms can be cited.

[0386] - "Substituted or unsubstituted haloalkyl"

[0387] As used herein, the term "substituted or unsubstituted haloalkyl" refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in "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 "substituted or unsubstituted alkyl" are replaced by halogen atoms. The carbon number of "unsubstituted haloalkyl" is 1 to 50, preferably 1 to 30, more preferably 1 to 18, unless otherwise specified herein. "Substituted haloalkyl" refers to a group in which one or more hydrogen atoms of "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 "substituted haloalkyl" are further replaced by substituents, and a group in which one or more hydrogen atoms of the substituents in "substituted haloalkyl" are further replaced by substituents. Specific examples of "unsubstituted haloalkyl" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl" (specific example group G3) are replaced by halogen atoms, etc. Haloalkyl is sometimes also referred to as haloalkyl group.

[0388] - "substituted or unsubstituted alkoxy"

[0389] Specific examples of "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 "unsubstituted alkoxy" is 1 to 50, preferably 1 to 30, more preferably 1 to 18, unless otherwise specified herein.

[0390] - "substituted or unsubstituted alkylthio"

[0391] Specific examples of "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 "unsubstituted alkylthio" is 1 to 50, preferably 1 to 30, more preferably 1 to 18, unless otherwise specified herein.

[0392] - "substituted or unsubstituted aryloxy"

[0393] Specific examples of "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 "unsubstituted aryloxy" is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified herein.

[0394] - "substituted or unsubstituted arylthio"

[0395] 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.

[0396] - "substituted or unsubstituted trialkylsilyl"

[0397] As a specific example of the "trialkylsilyl" described in this specification, it is a group represented by -Si(G3)(G3)(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The plurality of G3 in -Si(G3)(G3)(G3) are the same as or different from each other. The carbon number of each alkyl group of the "trialkylsilyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.

[0398] - "substituted or unsubstituted aralkyl"

[0399] As a specific example of the "substituted or unsubstituted aralkyl" described in this specification, it is a group represented by -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. Therefore, the "aralkyl" is a group in which a hydrogen atom of the "alkyl" is replaced by an "aryl" as a substituent, and is a form of the "substituted alkyl". The "unsubstituted aralkyl" is an "unsubstituted alkyl" substituted by an "unsubstituted aryl", and the carbon number of the "unsubstituted aralkyl" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.

[0400] As specific examples of the "substituted or unsubstituted aralkyl", benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl can be cited.

[0401] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group is preferably phenyl, p-biphenylyl, m-biphenylyl, o-biphenylyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, pyrenyl, chrysenyl, triphenylenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl, etc.

[0402] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic group is preferably pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, phenanthrolinyl, carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, or 9-carbazolyl), benzocarbazolyl, azacarbazolyl, diazacarbazolyl, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, azadibenzothiophenyl, diazadibenzothiophenyl, (9-phenyl)carbazolyl ((9-phenyl)carbazol-1-yl, (9-phenyl)carbazol-2-yl, (9-phenyl)carbazol-3-yl, or (9-phenyl)carbazol-4-yl), (9-biphenylyl)carbazolyl, (9-phenyl)phenylcarbazolyl, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl, and phenyldibenzothiophenyl, etc.

[0403] In this specification, unless otherwise specified, the carbazolyl group is specifically any of the following groups.

[0404] [Chemical formula 7]

[0405]

[0406] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically any of the following groups.

[0407] [Chemical formula 8]

[0408]

[0409] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents the bonding position.

[0410] In this specification, unless otherwise specified, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups.

[0411] [Chemical Formula 9]

[0412]

[0413] In the above general formulas (TEMP-34) to (TEMP-41), * represents the bonding position.

[0414] Unless otherwise specified in this specification, the substituted or unsubstituted alkyl groups are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.

[0415] ・ "Substituted or unsubstituted arylene group"

[0416] Unless otherwise specified in this specification, the "substituted or unsubstituted arylene group" is a divalent group derived by removing one hydrogen atom from the aryl ring of the above "substituted or unsubstituted aryl group". As specific examples (specific example group G12) of the "substituted or unsubstituted arylene group", divalent groups derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described in specific example group G1 can be cited, etc.

[0417] ・ "Substituted or unsubstituted divalent heterocyclic group"

[0418] Unless otherwise specified in this specification, the "substituted or unsubstituted divalent heterocyclic group" is a divalent group derived by removing one hydrogen atom from the heterocyclic ring of the above "substituted or unsubstituted heterocyclic group". As specific examples (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group", divalent groups derived by removing one hydrogen atom from the heterocyclic ring of the "substituted or unsubstituted heterocyclic group" described in specific example group G2 can be cited, etc.

[0419] ・ "Substituted or unsubstituted alkylene group"

[0420] Unless otherwise specified in this specification, the "substituted or unsubstituted alkylene group" is a divalent group derived by removing one hydrogen atom from the alkyl chain of the above "substituted or unsubstituted alkyl group". As specific examples (specific example group G14) of the "substituted or unsubstituted alkylene group", divalent groups derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl group" described in specific example group G3 can be cited, etc.

[0421] Unless otherwise specified in this specification, the substituted or unsubstituted arylene group is preferably any group in the following general formulas (TEMP-42) to (TEMP-68).

[0422] [Chemical Formula 10]

[0423]

[0424] [Chemical Formula 11]

[0425]

[0426] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent.

[0427] In the above general formulas (TEMP-42) to (TEMP-52), * represents the bonding position.

[0428] [Chemical Formula 12]

[0429]

[0430] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent.

[0431] The groups Q9 and Q 10 can be bonded to each other via a single bond to form a ring.

[0432] In the above general formulas (TEMP-53) to (TEMP-62), * represents the bonding position.

[0433] [Chemical Formula 13]

[0434]

[0435] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0436] In the above general formulas (TEMP-63) to (TEMP-68), * represents the bonding position.

[0437] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any of the groups represented by the following general formulas (TEMP-69) to (TEMP-102).

[0438] [Chemical Formula 14]

[0439]

[0440] [Chemical Formula 15]

[0441]

[0442] [Chemical Formula 16]

[0443]

[0444] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0445] [Chemical formula 17]

[0446]

[0447] [Chemical formula 18]

[0448]

[0449] [Chemical formula 19]

[0450]

[0451] [Chemical formula 20]

[0452]

[0453] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0454] The above is the description of "substituents described in this specification".

[0455] ・"When bonding to form a ring"

[0456] In this specification, when it is described that "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".

[0457] For 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" and 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" in this specification (hereinafter, these cases may sometimes be collectively referred to as "when bonding to form a ring"), 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 parent skeleton as an example.

[0458] [Chemical formula 21]

[0459]

[0460] For example, R 921 ~R 930 When "one or more of the groups composed of two or more adjacent ones are bonded to each other to form a ring", the group composed of two adjacent ones that forms one group refers to R 921 and R 922 's group, R 922 and R 923 's group, R 923 and R 924 's group, R 924 and R 930 's group, R 930 and R 925 's group, R 925 and R 926 's group, R 926 and R 927 's group, R 927 and R 928 's group, R 928 and R 929 's group, and R 929 and R 921 's group.

[0461] The above "one or more" means that two or more of the above groups composed of two or more adjacent ones can form a ring simultaneously. For example, 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 When this happens, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0462] [Chemical formula 22]

[0463]

[0464] The case where the "group composed of two or more adjacent ones" forms a ring means that it includes not only the case where the group composed of "two" adjacent ones as shown in the above example is bonded, but also the case where the group composed of "three or more" adjacent ones is bonded. For example, it means that R 921 and R 922 are bonded to each other to form ring Q A and R 922 and R 923 are bonded to each other to form ring Q C , and the three adjacent ones (R 921 , R 922 and R 923When the groups that make up the group are bonded to each other to form a ring and are fused to the anthracene mother skeleton, 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 .

[0465] [Chemical formula 23]

[0466]

[0467] The "monocyclic ring" or "fused ring" formed by to

[0467] can be a saturated ring or an unsaturated ring only in terms of the structure of the formed ring. When "one of the two adjacent groups that make up the group" 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 are fused through ring Q A and ring Q C to form a fused ring. 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.

[0468] "Unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. "Saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.

[0469] As a specific example of an 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.

[0470] As a specific example of an 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.

[0471] As a specific example of an 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.

[0472] "Forming a ring" means forming a ring only with multiple atoms of the parent skeleton, or forming a ring with multiple 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 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, when forming ring Q 921 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.

[0473] Here, the "optional element" is preferably at least one element selected from the group consisting of carbon element, nitrogen element, oxygen element and 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 the carbon element is included, the formed ring is a heterocyclic ring.

[0474] Unless otherwise specified in this specification, the "one or more optional elements" constituting a single ring or a fused ring are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and further preferably 3 or more and 5 or less.

[0475] Unless otherwise specified in this specification, among the "single ring" and the "fused ring", the "single ring" is preferred.

[0476] Unless otherwise specified in this specification, among the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred.

[0477] Unless otherwise specified in this specification, the "single ring" is preferably a benzene ring.

[0478] Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring.

[0479] When "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", unless otherwise specified in this specification, it is preferred that: one or more of the groups composed of two or more adjacent ones 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 the number of elements being one or more and 15 or less.

[0480] 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.

[0481] When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "fused ring" has a substituent are the substituents described in the item of "substituents described in this specification" above.

[0482] The above is the description of the case of "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" and the case of "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" (the case of "bonding to form a ring").

[0483] ・Substituents when expressed as "substituted or unsubstituted"

[0484] In one embodiment of this specification, the substituents when expressed as "substituted or unsubstituted" (in this specification, sometimes referred to as "optional substituents") are, for example, selected from

[0485] unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0486] unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0487] unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0488] unsubstituted cycloalkyl groups having 3 to 50 ring carbon atoms,

[0489] -Si(R 901 )(R 902 )(R 903 ),

[0490] -O-(R 904 ),

[0491] -S-(R905 ),

[0492] -N(R 906 )(R 907 ),

[0493] a halogen atom, a cyano group, a nitro group,

[0494] an unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0495] an unsubstituted heterocyclic group having 5 to 50 ring atoms

[0496] and the like in the group consisting of,

[0497] Here, R 901 to R 907 are each independently

[0498] a hydrogen atom,

[0499] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0500] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0501] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0502] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0503] When there are two or more R 901 s, two or more R 901 s may be the same or different from each other,

[0504] When there are two or more R 902 s, two or more R 902 s may be the same or different from each other,

[0505] When there are two or more R 903 s, two or more R 903 s may be the same or different from each other,

[0506] When there are two or more R 904 s, two or more R 904 s may be the same or different from each other,

[0507] When there are two or more R 905 s, two or more R 905 s may be the same or different from each other,

[0508] When there are two or more R 906 s, two or more R 906 s may be the same or different from each other,

[0509] When there are two or more R907 When there are two or more, two or more Rs 907 are the same as or different from each other.

[0510] In one embodiment, when the above expression is "substituted or unsubstituted", the substituents are selected from the group consisting of

[0511] an alkyl group having 1 to 50 carbon atoms,

[0512] an aryl group having 6 to 50 ring carbon atoms, and

[0513] a heterocyclic group having 5 to 50 ring atoms

[0514] in the group consisting of.

[0515] In one embodiment, when the above expression is "substituted or unsubstituted", the substituents are selected from the group consisting of

[0516] an alkyl group having 1 to 18 carbon atoms,

[0517] an aryl group having 6 to 18 ring carbon atoms, and

[0518] a heterocyclic group having 5 to 18 ring atoms

[0519] in the group consisting of.

[0520] Specific examples of each of the above optional substituents are the specific examples of the substituents described in the item of "substituents described in this specification" above.

[0521] In this specification, unless otherwise noted, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring" with each other, preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, and more preferably a benzene ring.

[0522] In this specification, unless otherwise noted, an optional substituent may further have a substituent. The substituent further possessed by the optional substituent is the same as the above optional substituent.

[0523] In this specification, the numerical range represented by "AA to BB" means the range including the numerical value AA described before "AA to BB" as the lower limit value and the numerical value BB described after "AA to BB" as the upper limit value.

[0524] Hereinafter, the compounds of the present invention will be described.

[0525] 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 following various formulas may sometimes be simply referred to as "invention compounds".

[0526] [Chemical formula 24]

[0527]

[0528] Hereinafter, the symbols in formula (1) and the following various formulas will be described. It should be noted that as long as there is no special description, the same symbols in the following formulas have the same meaning.

[0529] Ar 1 and Ar 2 Each independently represents a group represented by any one of formulas (10) to (14).

[0530] [Chemical formula 25]

[0531]

[0532] R 11 ~R 15 、R 21 ~R 26 、R 41 ~R 48 、R 51 ~R 62 and R 71 ~R 78 Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a halogen atom, a cyano group, a nitro group, 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.

[0533] R 31 ~R 35 Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0534] X is an oxygen atom, a sulfur atom or NR 81 , R 81 is a hydrogen atom, 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.

[0535] X is preferably an oxygen atom.

[0536] R 81 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, more preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and further preferably a phenyl group.

[0537] Among them, selected from R 11 ~R 15 One of them is a single bond to *c, selected from R 21 ~R 26 One of them is a single bond to *d, selected from R 21 ~R 26 The other one is a single bond bonded to *e, selected from R 45 ~R 48 One of them is a single bond bonded to *f, selected from R 59 ~R 62 One of them is a single bond bonded to *g, selected from R 75 ~R 78 and R 81 One of them is a single bond bonded to *i, and *h is bonded to one selected from carbon atoms *4 to *8.

[0538] R 45 or R 46 Preferably, it is a single bond bonded to *f, R 45 More preferably, it is a single bond bonded to *f.

[0539] R 60 or R 61 It is preferably a single bond bonded to *g.

[0540] In one embodiment of the present invention, R 75 ~R 78 It is preferably a single bond bonded to *i, R 75 More preferably, it is a single bond bonded to *i.

[0541] In another embodiment of the present invention, when m is 0 and n is 0, or when m is 1 and n is 1, R 81 It is preferably a single bond bonded to *i.

[0542] *h is preferably bonded to the carbon atom *8.

[0543] R is selected from the group consisting of 11 ~R 15 Two adjacent R 21 ~R 26 Two adjacent ones in R 31 ~R 35 Two adjacent R 41 ~R 48 Two adjacent R 51 ~R 62 Two adjacent ones of 71 ~R78 Two adjacent ones in [] do not bond to each other, and thus do not form a ring structure.

[0544] R of the above single bond is not 11 ~R 15 can all be hydrogen atoms, and R of the above any single bond is not 21 ~R 26 can all be hydrogen atoms, and R 31 ~R 35 can all be hydrogen atoms, and R of the above single bond is not 41 ~R 48 can all be hydrogen atoms, and R of the above single bond is not 51 ~R 62 can all be hydrogen atoms, and R of the above single bond is not 71 ~R 78 can all be hydrogen atoms.

[0545] ** represents the bonding position with the central nitrogen atom, m is 0 or 1, and n is 0 or 1.

[0546] In formulas (10) to (12) and (14), when m is 0 and n is 0, *e bonds to the central nitrogen atom; when m is 0 and n is 1, *c bonds to the central nitrogen atom; when m is 1 and n is 0, *e bonds to one selected from R 11 ~R 15 among them.

[0547] In formula (13), when m is 0 and n is 1, *c bonds to the central nitrogen atom; when m is 1 and n is 0, *e bonds to one selected from R 11 ~R 15 among them, excluding the case where m is 0 and n is 0.

[0548] In formula (14), when m is 0 and n is 1, and when m is 1 and n is 0, one selected from R 75 ~R 78 among them is a single bond bonding to *i.

[0549] In one embodiment of the present invention, in formulas (10) to (12) and (14), m is 0 and n is 0. In another embodiment of the present invention, in formulas (10) to (13) and (14), m is 1 and n is 1. In yet another embodiment, in formulas (10) to (13), m is 0 and n is 1.

[0550] Benzene ring A is not crosslinked with benzene ring B, benzene ring A is not crosslinked with benzene ring C, benzene ring B is not crosslinked with benzene ring C, benzene ring A is not crosslinked with the naphthalene ring, and benzene ring B is not crosslinked with the naphthalene ring.

[0551] The group represented by formula (10) is preferably a substituted or unsubstituted group selected from the following formulas.

[0552] [Chemical Formula 26]

[0553]

[0554] (In the formula, optional substituents are omitted.)

[0555] The group represented by formula (11) is preferably a substituted or unsubstituted group selected from the following formulae.

[0556] [Chemical Formula 27]

[0557]

[0558] (In the formula, optional substituents are omitted.)

[0559] The group represented by formula (12) is preferably a substituted or unsubstituted group selected from the following formulae.

[0560] [Chemical Formula 28]

[0561]

[0562] (In the formula, optional substituents are omitted.)

[0563] The group represented by formula (13) is preferably an unsubstituted group selected from the following formulae.

[0564] [Chemical Formula 29]

[0565]

[0566] (In the formula, optional substituents are omitted.)

[0567] In one embodiment of the present invention, the group represented by formula (14) is preferably a group represented by formula (14-1).

[0568] In another embodiment of the present invention, the group represented by formula (14) is preferably a group represented by formula (14-2).

[0569] [Chemical formula 30]

[0570]

[0571] (Where,

[0572] R 11 ~R 15 、R 21 ~R 26 、R 71 ~R 78 , *c, *d, *e, X, **, m, n, benzene ring A, and benzene ring B are as defined in formula (1).

[0573] Selected from R 75 ~R 78 One of them is a single bond to *j. )

[0574] In formula (14-1), R 75 It is preferably a single bond bonded to *i.

[0575] In one embodiment of the present invention, the group represented by formula (14) is preferably a group represented by formula (14-1-1).

[0576] [Chemical Formula 31]

[0577]

[0578] (Where,

[0579] R 11 ~R 15 、R 71 ~R 78 , *c, X, **, m, and the benzene ring A are as defined in formula (1).

[0580] Selected from R 75 ~R 78 One of them is a single bond to *j. )

[0581] In formula (14-1-1), R 75 It is preferably a single bond bonded to *i.

[0582] The group represented by formula (14) is preferably a substituted or unsubstituted group selected from the following formulae.

[0583] [Chemical Formula 32]

[0584]

[0585] (In the formula, optional substituents are omitted.)

[0586] Ar 1 and Ar 2 Each is independently preferably a group represented by any of the formulae (10), (11) and (14), and more preferably Ar 1 and Ar 2 At least one of them is a group represented by formula (11).

[0587] Ar 1 and Ar 2 Preferably, each independently represents a group represented by any of formulae (20) to (24).

[0588] [Chemical Formula 33]

[0589]

[0590] (In the formula,

[0591] R 11 ~R 15 、R 21 、R 22 、R 24 、R 25 、R 31 ~R 35 、R 41 ~R 48 、R 51 ~R 62 、R 71 ~R 78 、*f, *g, *h, *i, X, **, m, n, benzene ring A, benzene ring B and benzene ring C are as defined in formula (1).)

[0592] In one embodiment of the present invention, in formulas (20) to (22) and (24), m is 0 and n is 0. In another embodiment of the present invention, in formulas (20) to (24), m is 1 and n is 1. In yet another embodiment, in formulas (20) to (24), m is 0 and n is 1.

[0593] In one embodiment of the present invention, the group represented by formula (24) is preferably the group represented by formula (24-1).

[0594] In another embodiment of the present invention, the group represented by formula (24) is preferably the group represented by formula (24-2).

[0595] [Chemical formula 34]

[0596]

[0597] (In the formula,

[0598] R 11 、R 12 、R 14 、R 15 、R 21 、R 22 、R 24 、R 25 、R 71 ~R 78 、X, **, m, n, benzene ring A and benzene ring B are as defined in formula (1).

[0599] Selected from R 75 ~R 78 One of them is a single bond bonded to *j.)

[0600] In formula (24-1), R 75 is preferably a single bond bonded to *i.

[0601] In one embodiment of the present invention, the group represented by formula (24) is preferably the group represented by formula (24-1-1).

[0602] [Chemical formula 35]

[0603]

[0604] (wherein,

[0605] R 11 , R 12 , R 14 , R 15 , R 71 ~R 78 , X, **, m, and benzene ring A are as defined in formula (1).

[0606] One selected from R 75 ~R 78 is a single bond bonded to *j.)

[0607] *a is bonded to one selected from carbon atoms *1 to *3.

[0608] *a is preferably bonded to carbon atom *2 or *3, more preferably bonded to *3.

[0609] R 1 ~R 4 are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0610] Among them, one selected from R 1 ~R 4 , preferably R 2 and R 3 are single bonds bonded to *b.

[0611] Two adjacent ones selected from R 1 ~R 4 that are not single bonds bonded to *b do not bond to each other, and thus do not form a ring structure.

[0612] R 1 ~R 4 that are not single bonds bonded to *b can all be hydrogen atoms.

[0613] R 5 ~R 9 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted phenyl group.

[0614] Among them, one selected from R 5 ~R 9Two adjacent ones among them can each independently bond to each other to form a substituted or unsubstituted ring structure, or they may not bond to each other, thus not forming a ring structure.

[0615] Among those selected from R 5 ~R 9 When two adjacent ones among them each independently bond to each other to form a substituted or unsubstituted ring structure, the following formula is preferred.

[0616] [Chemical formula 36]

[0617]

[0618] R 5 ~R 9 can all be hydrogen atoms.

[0619] The details of the substituted or unsubstituted alkyl group with 1 to 50 carbon atoms as described in the definitions of the above formulas are as described in "Substituents described in this specification".

[0620] 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, tert-butyl, and further preferably methyl, tert-butyl.

[0621] The details of the substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms as described in the definitions of the above formulas are as described in "Substituents described in this specification".

[0622] The above-mentioned substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms is preferably selected from phenyl, 1-naphthyl, 2-naphthyl, 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, m-terphenyl-3'-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, and o-terphenyl-2-yl.

[0623] The details of any substituted or unsubstituted ring structure formed by two adjacent ones as described in the definitions of the above formulas are as described in "Substituents described in this specification", and are selected from substituted or unsubstituted aromatic hydrocarbon rings, substituted or unsubstituted aliphatic hydrocarbon rings, substituted or unsubstituted aromatic heterocycles, and substituted or unsubstituted non-aromatic heterocycles.

[0624] The above-mentioned aromatic hydrocarbon ring is, for example, a benzene ring, a biphenylene ring, a naphthalene ring, or a fluorene ring, and is preferably a naphthalene ring or a fluorene ring.

[0625] The above-mentioned aliphatic hydrocarbon ring is, for example, a cyclopentene ring, a cyclopentadiene ring, a cyclohexene ring, a cyclohexadiene ring, or a hydrocarbon ring obtained by partial hydrogenation of the above-mentioned aromatic hydrocarbon ring.

[0626] The above aromatic heterocycles are, for example, a pyrrole ring, a furan ring, a thiophene ring, a pyridine ring, an imidazole ring, a pyrazole ring, an indole ring, an isoindole ring, a benzofuran ring, an isobenzofuran ring, a benzothiophene ring, a benzimidazole ring, an indazole ring, a dibenzofuran ring, a naphthobenzofuran ring, a dibenzothiophene ring, a naphthobenzothiophene ring, a carbazole ring, or a benzocarbazole ring, preferably a dibenzofuran ring, a dibenzothiophene ring or a carbazolyl ring.

[0627] The above non-aromatic heterocycles are, for example, heterocycles obtained by partial hydrogenation of the above aromatic heterocycles.

[0628] When each group in the definitions of the above formulas has an optional substituent, the details of the optional substituent represented by "substituted or unsubstituted" are as described in "substituents when expressed as'substituted or unsubstituted'". The optional substituent is preferably an alkyl group having 1 to 50 carbon atoms or an aryl group having 6 to 50 ring carbon atoms, and the details of the alkyl group and the aryl group are as described above.

[0629] As described above, the "hydrogen atom" used in this specification includes a protium atom, a deuterium atom, and a tritium atom. Therefore, the inventive compound may contain deuterium atoms of natural origin.

[0630] In addition, by using a compound in which part or all of the raw material compound is deuterated, deuterium atoms can be intentionally introduced into the inventive compound. Therefore, in one aspect of the present invention, the inventive compound contains at least 1 deuterium atom. That is, the inventive compound may be a compound represented by formula (1), and at least one of the hydrogen atoms contained in the compound is a deuterium atom.

[0631] Selected from the following hydrogen atoms, namely

[0632] R 1 ~R 4 Any of the hydrogen atoms represented; R 1 ~R 4 Any of the hydrogen atoms of the substituted or unsubstituted alkyl group represented;

[0633] R 5 ~R 9 Any of the hydrogen atoms represented; R 5 ~R 9 Any of the hydrogen atoms of the substituted or unsubstituted alkyl group or the substituted or unsubstituted phenyl group represented;

[0634] R 11 ~R 15 、R 21 ~R 26 、R 31 ~R 35 、R41 ~R 48 、R 51 ~R 62 and R 71 ~R 78 A hydrogen atom represented by any of R 11 ~R 15 、R 21 ~R 26 、R 31 ~R 35 、R 41 ~R 48 、R 51 ~R 62 and R 71 ~R 78 a hydrogen atom possessed by a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group represented by any of ;

[0635] R 81 The hydrogen atom shown; R 81 a hydrogen atom possessed by the substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heterocyclic group;

[0636] a hydrogen atom possessed by the phenylene group bonded to the central nitrogen atom clearly described in formula (1) (i.e., a hydrogen atom possessed by ring D in the following formula (1D));

[0637] A hydrogen atom not bonded to the central nitrogen atom explicitly described in formula (1) and possessed by an unsubstituted phenyl group (i.e., a hydrogen atom possessed by ring E in formula (1D) below);

[0638] At least one hydrogen atom in may be a deuterium atom.

[0639] [Chemical Formula 37]

[0640]

[0641] In formula (1D), Ar 1 、Ar 2 、R 1 ~R 9 , *a, *b and *1 to *3 are as defined in formula (1).

[0642] The deuteration rate of the invention compound depends on the deuteration rate of the raw material compound used. Even when using raw materials with a specified deuteration rate, naturally occurring protium isotopes may be contained at a certain ratio. Therefore, the deuteration rate of the invention compound shown below includes a ratio that takes into account trace amounts of naturally occurring isotopes, compared to the ratio calculated by simply counting the number of deuterium atoms shown in the chemical formula.

[0643] The deuteration rate of the inventive compound is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and even more preferably 50% or more.

[0644] The inventive compound may be a mixture containing a deuterated compound and a non-deuterated compound, or a mixture of two or more compounds having different deuteration rates. The deuteration rate of such a mixture is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, further preferably 10% or more, further preferably 50% or more, and less than 100%.

[0645] In addition, the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the inventive compound is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, further preferably 10% or more, and 100% or less.

[0646] Those skilled in the art can easily manufacture the inventive compound with reference to the following synthesis examples and well-known synthesis methods.

[0647] Specific examples of the inventive compound are shown below, but are not limited to the exemplified compounds below.

[0648] [Chemical formula 38]

[0649]

[0650] [Chemical formula 39]

[0651]

[0652] [Chemical formula 40]

[0653]

[0654] [Chemical formula 41]

[0655]

[0656] [Chemical formula 42]

[0657]

[0658] [Chemical formula 43]

[0659]

[0660] [Chemical formula 44]

[0661]

[0662] [Chemical formula 45]

[0663]

[0664] [Chemical Formula 46]

[0665]

[0666] [Chemical Formula 47]

[0667]

[0668] [Chemical Formula 48]

[0669]

[0670] [Chemical Formula 49]

[0671]

[0672] [Chemical Formula 50]

[0673]

[0674] [Chemical Formula 51]

[0675]

[0676] [Chemical Formula 52]

[0677]

[0678] [Chemical Formula 53]

[0679]

[0680] [Chemical Formula 54]

[0681]

[0682] [Chemical Formula 55]

[0683]

[0684] [Chemical Formula 56]

[0685]

[0686] [Chemical Formula 57]

[0687]

[0688] [Chemical Formula 58]

[0689]

[0690] [Chemical Formula 59]

[0691]

[0692] [Chemical Formula 60]

[0693]

[0694] [Chemical Formula 61]

[0695]

[0696] [Chemical Formula 62]

[0697]

[0698] [Chemical Formula 63]

[0699]

[0700] [Chemical Formula 64]

[0701]

[0702] [Chemical Formula 65]

[0703]

[0704] [Chemical Formula 66]

[0705]

[0706] [Chemical Formula 67]

[0707]

[0708] [Chemical Formula 68]

[0709]

[0710] [Chemical Formula 69]

[0711]

[0712] [Chemical Formula 70]

[0713]

[0714] [Chemical Formula 71]

[0715]

[0716] [Chemical Formula 72]

[0717]

[0718] [Chemical Formula 73]

[0719]

[0720] [Chemical Formula 74]

[0721]

[0722] [Chemical Formula 75]

[0723]

[0724] [Chemical Formula 76]

[0725]

[0726] [Chemical Formula 77]

[0727]

[0728] [Chemical Formula 78]

[0729]

[0730] [Chemical Formula 79]

[0731]

[0732] [Chemical Formula 80]

[0733]

[0734] [Chemical Formula 81]

[0735]

[0736] [Chemical Formula 82]

[0737]

[0738] [Chemical Formula 83]

[0739]

[0740] [Chemical Formula 84]

[0741]

[0742] [Chemical Formula 85]

[0743]

[0744] [Chemical Formula 86]

[0745]

[0746] [Chemical Formula 87]

[0747]

[0748] [Chemical Formula 88]

[0749]

[0750] [Chemical Formula 89]

[0751]

[0752] [Chemical formula 90]

[0753]

[0754] [Chemical Formula 91]

[0755]

[0756] [Chemical Formula 92]

[0757]

[0758] [Chemical Formula 93]

[0759]

[0760] [Chemical Formula 94]

[0761]

[0762] [Chemical Formula 95]

[0763]

[0764] [Chemical Formula 96]

[0765]

[0766] [Chemical Formula 97]

[0767]

[0768] [Chemical Formula 98]

[0769]

[0770] [Chemical Formula 99]

[0771]

[0772] [Chemical Formula 100]

[0773]

[0774] [Chemical Formula 101]

[0775]

[0776] [Chemical Formula 102]

[0777]

[0778] [Chemical Formula 103]

[0779]

[0780] Materials for Organic EL Elements

[0781] The materials for organic EL elements of the present invention contain the inventive compounds. The content of the inventive compounds in the materials for organic EL elements is 1% by mass or more (including 100%), preferably 10% by mass or more (including 100%), more preferably 50% by mass or more (including 100%), still more preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%). The materials for organic EL elements of the present invention are useful in the manufacture of organic EL elements.

[0782] Organic EL Element

[0783] The organic EL element of the present invention includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer includes a light-emitting layer, and at least one layer of the organic layer contains the inventive compounds.

[0784] Examples of the organic layer containing the inventive compounds 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, a 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 compounds are preferably used as materials for the hole transport region or the light-emitting layer of a fluorescent or phosphorescent EL element, more preferably used as materials for the hole transport region, still more preferably used as materials for the hole injection layer, hole transport layer, electron blocking layer, or exciton blocking layer, and particularly preferably used as materials for the hole injection layer or hole transport layer.

[0785] The organic EL element of the present invention can be a monochromatic light-emitting element of a fluorescent or phosphorescent light-emitting type, or can be a white light-emitting element of a fluorescent / phosphorescent hybrid type, and can be a simple type having a single light-emitting unit or a tandem type having a plurality of light-emitting units. Among them, a fluorescent light-emitting type element is preferred. Here, the "light-emitting unit" refers to the smallest unit that includes an organic layer, at least one layer of which is a light-emitting layer and emits light by recombination of the injected holes and electrons.

[0786] For example, as a representative element configuration of a simple organic EL element, the following element configurations can be cited.

[0787] (1) Anode / Light-emitting unit / Cathode

[0788] In addition, the above light-emitting unit may also be a multilayer type having a plurality of phosphorescent light-emitting layers and fluorescent light-emitting layers. In this case, a spacer layer 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 a representative layer configuration of a simple light-emitting unit. The layers in parentheses are optional.

[0789] (a) (Hole injection layer / )Hole transport layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0790] (b) (Hole injection layer / )Hole transport layer / Phosphorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0791] (c) (Hole injection layer / )Hole transport layer / First fluorescent light-emitting layer / Second fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0792] (d) (Hole injection layer / )Hole transport layer / First phosphorescent light-emitting layer / Second phosphorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0793] (e) (Hole injection layer / )Hole transport layer / Phosphorescent light-emitting layer / Spacer layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0794] (f) (Hole injection layer / )Hole transport layer / First phosphorescent light-emitting layer / Second phosphorescent light-emitting layer / Spacer layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0795] (g) (Hole injection layer / )Hole transport layer / First phosphorescent light-emitting layer / Spacer layer / Second phosphorescent light-emitting layer / Spacer layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0796] (h) (Hole injection layer / )Hole transport layer / Phosphorescent light-emitting layer / Spacer layer / First fluorescent light-emitting layer / Second fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0797] (i) (Hole injection layer / )Hole transport layer / Electron blocking layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0798] (j) (Hole injection layer / )Hole transport layer / Electron blocking layer / Phosphorescent light-emitting layer / Electron transport layer ( / Electron injection layer)

[0799] (k) (Hole injection layer / ) Hole transport layer / Exciton blocking layer / Fluorescent emission layer / Electron transport layer ( / Electron injection layer )

[0800] (l) (Hole injection layer / ) Hole transport layer / Exciton blocking layer / Phosphorescent emission layer / Electron transport layer ( / Electron injection layer )

[0801] (m) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Fluorescent emission layer / Electron transport layer ( / Electron injection layer )

[0802] (n) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Phosphorescent emission layer / Electron transport layer ( / Electron injection layer )

[0803] (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 )

[0804] (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 )

[0805] (q) (Hole injection layer / ) Hole transport layer / Fluorescent emission layer / Hole blocking layer / Electron transport layer ( / Electron injection layer )

[0806] (r) (Hole injection layer / ) Hole transport layer / Phosphorescent emission layer / Hole blocking layer / Electron transport layer ( / Electron injection layer )

[0807] (s) (Hole injection layer / ) Hole transport layer / Fluorescent emission layer / Exciton blocking layer / Electron transport layer ( / Electron injection layer )

[0808] (t) (Hole injection layer / ) Hole transport layer / Phosphorescent emission layer / Exciton blocking layer / Electron transport layer ( / Electron injection layer )

[0809] 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.

[0810] It should be noted that an electron blocking layer can be appropriately provided between each emission layer and the hole transport layer or the spacer layer. In addition, a hole blocking layer can be appropriately provided between each emission layer and the electron transport layer. By providing the electron blocking layer and the hole blocking layer, electrons or holes can be confined in the emission layer, increasing the probability of charge recombination in the emission layer and improving the emission efficiency.

[0811] As a representative element configuration of a tandem organic EL element, the following element configurations can be cited.

[0812] (2) Anode / First light-emitting unit / Intermediate layer / Second light-emitting unit / Cathode

[0813] Here, as the above-mentioned first light-emitting unit and second light-emitting unit, for example, they can be independently selected from the above-mentioned light-emitting units.

[0814] The above-mentioned intermediate layer is generally also called 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 a known material.

[0815] 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, respectively, 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. Thus, electrons and holes can be confined in the light-emitting layer 5 to further improve the exciton generation efficiency in the light-emitting layer 5.

[0816] 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.

[0817] 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 the material forming a phosphorescent light-emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as the material for forming a fluorescent light-emitting layer. The same applies to the fluorescent host.

[0818] Substrate

[0819] The substrate is used as a support for the organic EL element. As the substrate, for example, plates such as glass, quartz, and plastic can be used. In addition, a flexible substrate can also be used. As the flexible substrate, for example, plastic substrates formed of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride can be cited. In addition, an inorganic vapor deposition film can also be used.

[0820] Anode

[0821] For the anode formed on the substrate, it is preferable to use metals, alloys, conductive compounds, and mixtures thereof having a large work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO: Indium Tin Oxide); indium tin oxide containing silicon or silicon oxide; indium zinc oxide; indium containing tungsten oxide and zinc oxide; graphene, etc. can be cited. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the above metals (for example, titanium nitride), etc. can be cited.

[0822] These materials are generally 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 with respect to indium oxide. In addition, it can also be produced by vacuum evaporation, coating, inkjet, spin coating, etc.

[0823] The hole injection layer formed adjacent to the anode is formed of a material that is easy to inject holes regardless of the work function of the anode. Therefore, as the electrode material, generally used materials (for example, metals, alloys, conductive compounds, and mixtures thereof, elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0824] 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) and calcium (Ca), and alloys containing them (for example, 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.

[0825] Hole injection layer

[0826] The hole injection layer is a layer containing a material with high hole injection property (hole injection material), formed between the anode and the light-emitting layer, or formed between the hole transport layer and the anode if present.

[0827] As hole injection materials other than the inventive compounds, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. can be used.

[0828] As hole injection layer materials, aromatic amine compounds such as 4,4’,4’’-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4’,4’’-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4’-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4’-bis(N-{4-[N’-(3-methylphenyl)-N’-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), etc. can also be cited as low molecular organic compounds.

[0829] High molecular compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N’-[4-(4-diphenylamino)phenyl]phenyl-N’-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N’-bis(4-butylphenyl)-N,N’-bis(phenyl)benzidine] (abbreviation: Poly-TPD), etc. can be cited. In addition, acid-added high molecular compounds such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly(styrenesulfonic acid) (PAni / PSS), etc. can also be used.

[0830] Furthermore, acceptor materials such as hexaazatriphenylene (HAT) compounds represented by the following formula (K) are also preferably used.

[0831] [Chemical formula 104]

[0832]

[0833] (In the above formula, R 21 ~R 26 each independently represents a cyano group, -CONH2, 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). Further, 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-).

[0834] As R 27 , examples include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, a cyclopentyl group, a cyclohexyl group, etc.

[0835] Hole transport layer

[0836] The hole transport layer is a layer containing a material with high hole transport property (hole transport material), formed between the anode and the light-emitting layer, or formed between the hole injection layer and the light-emitting layer in the case of its existence. The inventive compound can be used alone or in combination with the following compounds for the hole transport layer.

[0837] The hole transport layer can be a single-layer structure or a multilayer 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 hole transport layer of the above single-layer structure is preferably adjacent to the light-emitting layer. Further, the hole transport layer closest to the cathode in the above multilayer structure, for example, the second hole transport layer of the above two-layer structure, 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 hole transport layer of the above single-layer structure and the light-emitting layer, or between the hole transport layer closest to the light-emitting layer in the above multilayer structure and the light-emitting layer.

[0838] In the hole transport layer of the above two-layer structure, the inventive compound can be contained in one of the first hole transport layer and the second hole transport layer, or can be contained in both.

[0839] In one aspect of the present invention, it is preferred that the inventive compound is only contained in the first hole transport layer. In another aspect, it is preferred that the inventive compound is only contained in the second hole transport layer. In yet another aspect, it is preferred that the inventive compound is contained in the first hole transport layer and the second hole transport layer.

[0840] In one embodiment of the present invention, from the perspective of manufacturing cost, the inventive compound contained in one or both of the above-described first hole transport layer and the second hole transport layer is preferably protium.

[0841] The above-mentioned protium refers to an inventive compound in which all hydrogen atoms in the inventive compound are protium atoms.

[0842] Therefore, the present invention includes an organic EL element, wherein one or both of the above-described first hole transport layer and the second hole transport layer contain an inventive compound consisting essentially of only protium. "An inventive compound consisting essentially of only protium" means that the content ratio of protium is 90 mol% or more, preferably 95 mol% or more, more preferably 99 mol% or more (including 100% respectively) relative to the total amount of the inventive compound.

[0843] 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.

[0844] As the aromatic amine compound, for example, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) can be mentioned. The above compounds have a hole mobility of 10 -6 cm 2 / Vs or more.

[0845] 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.

[0846] As anthracene derivatives, examples thereof include 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-bis(2-naphthyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth).

[0847] Polymeric compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.

[0848] Among them, as long as the compound has a higher hole transport property than the electron transport property, compounds other than the above can also be used.

[0849] Dopant material for the light-emitting layer

[0850] The light-emitting layer is a layer containing a highly luminescent material (dopant material), and various materials can be used. For example, fluorescent light-emitting materials and phosphorescent light-emitting materials can be used as the dopant material. The fluorescent light-emitting material is a compound that emits light from the singlet excited state, and the phosphorescent light-emitting material is a compound that emits light from the triplet excited state.

[0851] As the blue fluorescent light-emitting material that can be used for the light-emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. can be used. Specifically, examples thereof include 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.

[0852] As a green fluorescent light-emitting material that can be used in the light-emitting layer, an aromatic amine derivative or the like can be used. Specifically, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), etc. can be cited.

[0853] As a red fluorescent light-emitting material that can be used in the light-emitting layer, a tetracene derivative, a diamine derivative or the like can be used. Specifically, N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), etc. can be cited.

[0854] As a blue phosphorescent light-emitting material that can be used in the light-emitting layer, metal complexes such as an iridium complex, an osmium complex, and a platinum complex 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) pyridinecarboxylate (abbreviation: FIrpic), bis[2-(3',5'-bis(trifluoromethyl)phenyl)pyridine-N,C2']iridium(III) pyridinecarboxylate (abbreviation: Ir(CF3ppy)2(pic)), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III) acetylacetonate (abbreviation: FIracac), etc. can be cited.

[0855] As a green phosphorescent material that can be used in the light-emitting layer, an iridium complex or the like is used. Examples include tris(2-phenylpyridine-N,C2')iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridine-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazole)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), bis(benzo[h]quinoline)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)), and the like.

[0856] As a red phosphorescent material that can be used in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used. Specifically, examples include bis[2-(2'-benzo[4,5-α]thienyl)pyridine-N,C3']iridium(III) acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinoline-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP), and other organometallic complexes.

[0857] In addition, rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: Eu(DBM)3(Phen)), tris[1-(2-thienoyl)-3,3,3-trifluoroacetone](monophenanthroline)europium(III) (abbreviation: Eu(TTA)3(Phen)) can be used as phosphorescent materials because they emit light from rare earth metal ions (electronic transitions between different multiplicities).

[0858] Host material of the light-emitting layer

[0859] The light-emitting layer can be configured to disperse the above dopant material in another material (host material). It is preferable to use a material with a lowest unoccupied molecular orbital energy level (LUMO energy level) higher than that of the dopant material and a highest occupied molecular orbital energy level (HOMO energy level) lower than that of the dopant material.

[0860] As the host material, for example, the following can be used:

[0861] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes,

[0862] (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives,

[0863] (3) Condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives,

[0864] (4) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives.

[0865] For example, the following metal complexes can be used: tris(8-hydroxyquinoline)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-hydroxyquinoline)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviation: BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviation: ZnBTZ), etc.;

[0866] 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2’,2’’-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), rubrene (abbreviation: BPhen), bathocuproine (abbreviation: BCP), etc. heterocyclic compounds;

[0867] 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9’-bianthracene (abbreviation: BANT), 9,9’-(stilbene-3,3’-diyl)diphenanthrene (abbreviation: DPNS), 9,9’-(stilbene-4,4’-diyl)diphenanthrene (abbreviation: DPNS2), 3,3’,3’’-(benzene-1,3,5-triyl)tripyrene (abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenylchrysene, etc. condensed aromatic compounds; and

[0868] 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.

[0869] Especially in the case of a blue fluorescent element, the following anthracene compounds are preferably used as the host material.

[0870] [Chemical formula 105]

[0871]

[0872] [Chemical formula 106]

[0873]

[0874] [Chemical formula 107]

[0875]

[0876] Electron transport layer

[0877] The electron transport layer is a layer containing a material with high electron transport properties (electron transport material), formed between the light-emitting layer and the cathode, or formed between the electron injection layer and the light-emitting layer when present.

[0878] 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 aspect 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 aspect of the present invention, a hole blocking layer described later may be interposed between the single-layer electron transport layer and the light-emitting layer, or between the electron transport layer closest to the light-emitting layer in the multi-layer structure and the light-emitting layer.

[0879] For example, the following can be used in the electron transport layer

[0880] (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes

[0881] (2) Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives

[0882] (3) Polymer compounds.

[0883] 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).

[0884] 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).

[0885] Examples of the polymer compound include poly[(9,9 - dihexylfluorene - 2,7 - diyl)-co-(pyridine - 3,5 - diyl)] (abbreviation: PF - Py), poly[(9,9 - dioctylfluorene - 2,7 - diyl)-co-(2,2'-bipyridine - 6,6'-diyl)] (abbreviation: PF - BPy).

[0886] 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.

[0887] Electron injection layer

[0888] The electron injection layer is a layer containing a material with high electron injection property. For the electron injection layer, alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), rare earth metals such as europium (Eu) and ytterbium (Yb), and compounds containing these metals can be used. Examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, rare earth metal oxides, rare earth metal halides, and rare earth metal-containing organic complexes. In addition, a mixture of multiple such compounds can also be used.

[0889] In addition, a material obtained by incorporating an alkali metal, an alkaline earth metal, or a compound thereof into a material having electron transportability can also be used. Specifically, a material obtained by incorporating magnesium (Mg) into Alq can be used, etc. It should be noted that at this time, electron injection from the cathode can be performed more efficiently.

[0890] Alternatively, a composite material obtained by mixing an organic compound and an electron donor can be used for the electron injection layer. Since the organic compound accepts electrons from the electron donor, such a composite material has excellent electron injection property and electron transportability. At this time, as the organic compound, a material with excellent transportability of the accepted electrons is preferred. Specifically, for example, the materials constituting the electron transport layer described above (metal complexes, heteroaromatic compounds, etc.) can be used. As the electron donor, any material that exhibits electron-donating property to the organic compound can be used. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples include lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. In addition, alkali metal oxides and alkaline earth metal oxides are preferred, and examples include lithium oxide, calcium oxide, barium oxide, etc. In addition, a Lewis base such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviation: TTF) can also be used.

[0891] Cathode

[0892] 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.

[0893] 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 or inkjet methods can be used.

[0894] 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 can be used to form the cathode regardless of the size of the work function. These conductive materials can be formed into films using sputtering, inkjet, spin coating, or other methods.

[0895] Insulating layer

[0896] Since an electric field is applied to an ultrathin film in an organic EL element, pixel defects due to leakage or short circuit are likely to occur. To prevent such pixel defects, an insulating layer including an insulating thin film layer can be inserted between a pair of electrodes.

[0897] 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 their mixtures or laminates can be used.

[0898] Spacer layer

[0899] The above-mentioned 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.

[0900] Since the spacer layer is provided between the 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 used for the spacer layer include the same materials as those used for the hole-transporting layer described above.

[0901] Blocking layer

[0902] 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.

[0903] 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 forming the layer.

[0904] The film thickness of each layer is not particularly limited. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur. On the contrary, if it is too thick, a high driving voltage is required and the efficiency deteriorates. Therefore, it is usually 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm.

[0905] 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-mounted lamps for electronic devices.

[0906] Examples

[0907] Hereinafter, the present invention will be described in more detail using examples, but the present invention is not limited to the following examples.

[0908] Invention compounds used in the production of the organic EL elements of Examples 1 to 22

[0909] [Chemical formula 108]

[0910]

[0911] [Chemical formula 109]

[0912]

[0913] Comparative compounds used in the production of the organic EL elements of Comparative Examples 1 to 4

[0914] [Chemical formula 110]

[0915]

[0916] Other compounds used in the production of the organic EL element

[0917] [Chemical formula 111]

[0918]

[0919] Fabrication of Organic EL Element

[0920] Example 1

[0921] 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.

[0922] The above-mentioned glass substrate with a transparent electrode after cleaning was mounted on the substrate holder of a vacuum evaporation apparatus. First, Compound HT1 and Compound HI1 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 HT1 to Compound HI1 (HT1:HI1) was 97:3.

[0923] Next, Compound HT1 was evaporated on the hole injection layer, forming a first hole transport layer with a film thickness of 80 nm.

[0924] Next, Compound Inv-2 was evaporated on the first hole transport layer, forming a second hole transport layer with a film thickness of 10 nm.

[0925] Next, Compound BH (host material) and Compound BD (dopant material) were co-evaporated on the second hole transport layer, forming a light-emitting layer with a film thickness of 25 nm. The mass ratio of Compound BH to Compound BD (BH:BD) was 96:4.

[0926] Next, Compound ET1 was evaporated on the light-emitting layer, forming a first electron transport layer with a film thickness of 10 nm.

[0927] Next, Compound ET2 and Liq were co-evaporated on the first electron transport layer, forming a second electron transport layer with a film thickness of 15 nm. The mass ratio of Compound ET2 to Liq was 50:50.

[0928] Next, LiF was evaporated on the second electron transport layer, forming an electron injection electrode with a film thickness of 1 nm.

[0929] Then, metal Al was evaporated on the electron injection electrode to form a metal cathode with a film thickness of 80 nm.

[0930] The layer structure of the organic EL element of Example 1 thus obtained is shown below.

[0931] ITO (130) / HT1:HI1 = 97:3 (10) / HT1 (80) / Compound Inv-2 (10) / BH:BD = 96:4 (25) / ET1 (10) / ET2:Liq = 50:50 (15) / LiF (1) / Al (80)

[0932] In the above layer configurations, the numbers in parentheses are film thicknesses (nm), and the ratios are mass ratios.

[0933] Comparative Example 1

[0934] Each organic EL device was produced in the same manner as in Example 1 except that the comparative compound Ref-1 was used instead of the compound Inv-2.

[0935] Examples 2 to 22, Comparative Examples 2 to 4

[0936] The organic EL elements of Examples 2 to 22 and Comparative Examples 2 to 4 were manufactured in the same manner as in Example 1, except that Compounds Inv-1, 3 to 22 and Comparative Compounds Ref-2 to 4 were used in sequence instead of Compound Inv-2, and HT2 was used instead of Compound HT1 of the hole injection layer and Compound HT1 of the first hole transport layer.

[0937] Determination of component life (LT90)

[0938] The obtained organic EL device was subjected to a current density of 50 mA / cm at room temperature. 2 The cells were driven with a constant DC current to emit light, and the time it took for the luminance to decrease to 90% of the initial luminance was measured, which was taken as the 90% lifetime (LT90). The results are shown in Tables 1 and 2.

[0939] Determination of External Quantum Efficiency (EQE)

[0940] The obtained organic EL device was subjected to a current density of 10 mA / cm at room temperature. 2 The device was driven with a DC constant current. The luminance was measured using a luminance meter (CS-1000, manufactured by Minolta Corporation), and the external quantum efficiency (%) was calculated based on the results. The results are shown in Table 1.

[0941] [Table 1]

[0942]

[0943] [Table 2]

[0944]

[0945] It is clearly known from the results of Tables 1 and 2 that the organic EL elements containing the inventive compounds (Compounds Inv-1 to 22) have a longer lifespan compared to the organic EL elements containing the comparative compounds (Ref-1 to 4). Additionally, it is clearly known from the results of Table 1 that the organic EL element containing the inventive compound (Compound Inv-2) exhibits a higher luminous efficiency compared to the organic EL element containing the comparative compound (Ref-1).

[0946] The inventive compounds synthesized in the synthesis examples

[0947] [Chemical formula 112]

[0948]

[0949] [Chemical formula 113]

[0950]

[0951] Synthesis Example 1: Synthesis of Compound Inv-1

[0952] [Chemical formula 114]

[0953]

[0954] Synthesis of Intermediate A

[0955] Under an argon atmosphere, 85.0 g of 3,4-dibromoaniline, 99.0 g of phenylboronic acid, 7.83 g of tetrakis(triphenylphosphine)palladium(0), 813 mL of 2M aqueous sodium carbonate solution, and 800 mL of 1,2-dimethoxyethane were mixed and stirred at 80 °C for 3 hours. Then, it was extracted with ethyl acetate. After drying the organic layer with anhydrous magnesium sulfate, it was concentrated, and the residue was purified by silica gel column chromatography to obtain 78.5 g of [1,1':2',1''-terphenyl]-4'-amine (Intermediate A). The yield was 94%.

[0956] Synthesis of Intermediate B

[0957] Under an argon atmosphere, 25.0 g of (1,1':2',1"-terphenyl)-4'-amine and 360 mL of acetonitrile were added to a flask and completely dissolved. 58.2 g of p-toluenesulfonic acid was added, and the mixture was then brought to 0°C. 180 mL of an aqueous solution containing 42.3 g of potassium iodide and 14.1 g of sodium nitrite was added dropwise to the mixture over 30 minutes. After stirring under ice-cooling for 30 minutes, 600 mL of water was added, the mixture was returned to room temperature, and stirred for a further 2 hours. Next, the generated solid was filtered, dissolved in 500 mL of toluene, and extracted with an aqueous sodium sulfate solution. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and washed with hexane to obtain 29.0 g of 4'-iodo-1,1':2',1"-terphenyl (Intermediate B). The yield was 80%.

[0958] Synthesis of intermediate C

[0959] Under an argon atmosphere, 22.5 g of Intermediate B, 9.88 g of 4-chlorophenylboronic acid, 1.34 g of dichlorobis(di-tert-butyl(4-dimethylaminophenyl)phosphine)palladium(II), 60 mL of a 2M aqueous sodium carbonate solution, and 240 mL of 1,2-dimethoxyethane were mixed and stirred at 80°C for 1.5 hours. Water was then added, and the precipitated solid was collected by filtration. The solid was recrystallized from a mixed solvent of toluene and hexane to obtain 18.3 g of 4'-(4-chlorophenyl)-1,1':2',1"-terphenyl (Intermediate C). The yield was 85%.

[0960] Synthesis of compound Inv-1

[0961] Under an argon atmosphere, 3.18 g of N-([1,1'-biphenyl]-4-yl)naphthalen-1-amine, 3.50 g of Intermediate C, 0.188 g of tris(dibenzylideneacetone)dipalladium(0), 0.238 g of tri-tert-butylphosphonium tetrafluoroborate, 1.48 g of sodium tert-butoxide, and 50 mL of toluene were mixed and stirred at 110°C for 5 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 3.36 g of a white solid. The yield was 55%.

[0962] The obtained substance was subjected to mass spectrometry analysis (m / e=600 relative to molecular weight 599.78), and was found to be compound Inv-1.

[0963] Synthesis Example 2: Synthesis of Compound Inv-2

[0964] [Chemical Formula 115]

[0965]

[0966] Under an argon atmosphere, 3.75 g of N-(4-(dibenzo[b,d]furan-4-yl)phenyl)naphthalene-1-amine, 3.25 g of Intermediate C, 0.175 g of tris(dibenzylideneacetone)dipalladium(0), 0.221 g of tri-tert-butylphosphonium tetrafluoroborate, 1.38 g of sodium tert-butoxide, and 53 mL of toluene were mixed and stirred at 110°C for 4 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 4.23 g of a white solid. The yield was 64%.

[0967] The obtained substance was subjected to mass spectrometry analysis (m / e=690 relative to molecular weight 689.86), and was identified as Compound Inv-2.

[0968] Synthesis Example 3: Synthesis of Compound Inv-3

[0969] [Chemical Formula 116]

[0970]

[0971] Synthesis of intermediate D

[0972] Under an argon atmosphere, 3.75 g of 1-naphthalene-2,3,4,5,6,7,8-d7-amine, 3.25 g of bromobenzene d5, 0.175 g of tris(dibenzylideneacetone)dipalladium(0), 0.221 g of tri-tert-butylphosphonium tetrafluoroborate, 5.24 g of sodium tert-butoxide, and 53 mL of toluene were mixed and stirred at 110°C for 4 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 8.75 g of Intermediate D as a white solid. The yield was 77%.

[0973] Synthesis of intermediate E

[0974] Under an argon atmosphere, 4.99 g of Intermediate D, 6.45 g of N-bromosuccinimide, and 180 mL of dehydrated dichloromethane were mixed and stirred at room temperature for 4 hours. Subsequently, 100 mL of water was added, and the mixture was stirred at room temperature for 1 hour. The mixture was then extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and concentrated, and the residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 6.78 g of Intermediate E as a yellow solid. The yield was 80%.

[0975] Synthesis of intermediate F

[0976] Under an argon atmosphere, 4.42 g of Intermediate E, 5.39 g of bis(pinacolato)diboron, 0.064 g of palladium(II) acetate, 0.270 g of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos), 7.55 g of potassium acetate, and 80 mL of 1,4-dioxane (anhydrous) were mixed and stirred at 100 °C for 4 hours. Next, 50 mL of water was added and stirred at room temperature for 1 hour. Then, extraction was performed with dichloromethane. After drying the organic layer with anhydrous magnesium sulfate, concentration under reduced pressure was carried out. The resulting residue was purified by silica gel column chromatography to obtain 6.44 g of Intermediate F as a white solid. The yield was 81%.

[0977] Synthesis of Intermediate G

[0978] Under an argon atmosphere, 3.99 g of Intermediate F, 0.74 mL of bromobenzene, 0.164 g of tetrakis(triphenylphosphine)palladium(0), 40 mL of 2M aqueous sodium carbonate solution, and 100 mL of 1,2-dimethoxyethane were mixed and stirred at 80 °C for 3 hours. Then, extraction was performed with toluene. After drying the organic layer with anhydrous magnesium sulfate, concentration was carried out, and the residue was purified by silica gel column chromatography to obtain 2.26 g of Intermediate G. The yield was 62%.

[0979] Synthesis of Compound Inv-3

[0980] Under an argon atmosphere, 2.53 g of Intermediate G, 1.76 g of 4'-iodo-1,1':2',1''-terphenyl, 0.114 g of tetrakis(triphenylphosphine)palladium(0), 14 mL of 2M aqueous sodium carbonate solution, and 40 mL of 1,2-dimethoxyethane were mixed and stirred at 80 °C for 3 hours. Then, extraction was performed with toluene. After drying the organic layer with anhydrous magnesium sulfate, concentration was carried out, and the residue was purified by silica gel column chromatography to obtain 2.09 g of a white solid. The yield was 69%.

[0981] As a result of mass spectrometry analysis of the obtained substance (m / e = 615 relative to a molecular weight of 614.87), it was Compound Inv-3.

[0982] Synthesis Example 4: Synthesis of Compound Inv-4

[0983] [Chemical formula 117]

[0984]

[0985] Under an argon atmosphere, 3.33 g of di([1,1'-biphenyl]-4-yl)amine, 3.54 g of Intermediate C, 0.196 g of tris(dibenzylideneacetone)dipalladium(0), 0.240 g of tri-tert-butylphosphonium tetrafluoroborate, 2.99 g of sodium tert-butoxide, and 58 mL of toluene were mixed and stirred at 110°C for 4 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 4.67 g of a white solid. The yield was 72%.

[0986] The obtained substance was subjected to mass spectrometry analysis (m / e=626 relative to molecular weight 625.82), and was identified as Compound Inv-4.

[0987] Synthesis Example 5: Synthesis of Compound Inv-5

[0988] [Chemical Formula 118]

[0989]

[0990] Under an argon atmosphere, 3.21 g of N-(4-(naphthalen-1-yl)phenyl)naphthalen-1-amine, 3.25 g of Intermediate C, 0.170 g of tris(dibenzylideneacetone)dipalladium(0), 0.216 g of tri-tert-butylphosphonium tetrafluoroborate, 2.68 g of sodium tert-butoxide, and 53 mL of toluene were mixed and stirred at 110°C for 4 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 6.04 g of a white solid. The yield was 68%.

[0991] The obtained substance was subjected to mass spectrometry analysis (m / e=650 relative to molecular weight 649.84), and was identified as Compound Inv-5.

[0992] Synthesis Example 6: Synthesis of Compound Inv-6

[0993] [Chemical Formula 119]

[0994]

[0995] Under an argon atmosphere, 3.01 g of N-(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1'-biphenyl]-4-amine, 2.97 g of Intermediate C, 0.160 g of tris(dibenzylideneacetone)dipalladium(0), 0.202 g of tri-tert-butylphosphonium tetrafluoroborate, 2.51 g of sodium tert-butoxide, and 48 mL of toluene were mixed and stirred at 110°C for 4 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 4.42 g of a white solid. The yield was 78%.

[0996] The obtained substance was subjected to mass spectrometry analysis (m / e=650 relative to molecular weight 649.84), and was identified as Compound Inv-6.

[0997] Synthesis Example 7: Synthesis of Compound Inv-7

[0998] [Chemical Formula 120]

[0999]

[1000] Under an argon atmosphere, 3.61 g of 4-(dibenzo[b,d]furan-4-yl)-N-phenylaniline, 3.67 g of intermediate C, 0.197 g of tris(dibenzylideneacetone)dipalladium(0), 0.250 g of tri-tert-butylphosphonium tetrafluoroborate, 3.10 g of sodium tert-butoxide, and 60 mL of toluene were mixed and stirred at 110°C for 4 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 5.58 g of a white solid. The yield was 81%.

[1001] The obtained substance was subjected to mass spectrometry analysis (m / e=690 relative to molecular weight 689.86), and was identified as Compound Inv-7.

[1002] Synthesis Example 8: Synthesis of Compound Inv-8

[1003] [Chemical Formula 121]

[1004]

[1005] Under an argon atmosphere, 2.85 g of N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]furan-1-amine, 2.89 g of Intermediate C, 0.155 g of tris(dibenzylideneacetone)dipalladium(0), 0.201 g of tri-tert-butylphosphonium tetrafluoroborate, 2.45 g of sodium tert-butoxide, and 47 mL of toluene were mixed and stirred at 110°C for 4 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 3.69 g of a white solid. The yield was 68%.

[1006] The obtained substance was subjected to mass spectrometry analysis (m / e=639, relative to molecular weight 639.26), and was identified as Compound Inv-8.

[1007] Synthesis Example 9: Synthesis of Compound Inv-9

[1008] [Chemical Formula 122]

[1009]

[1010] Under an argon atmosphere, 5.86 g of N-([1,1'-biphenyl]-4-yl)-9,9-biphenyl-9H-fluoren-4-amine, 4.10 g of Intermediate C, 0.220 g of tris(dibenzylideneacetone)dipalladium(0), 0.285 g of tri-tert-butylphosphonium tetrafluoroborate, 3.48 g of sodium tert-butoxide, and 67 mL of toluene were mixed and stirred at 110°C for 4 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 5.23 g of a white solid. The yield was 55%.

[1011] The obtained substance was subjected to mass spectrometry analysis (m / e=789, relative to molecular weight 789.34), and was found to be compound Inv-9.

[1012] Synthesis Example 10: Synthesis of Compound Inv-10

[1013] [Chemical formula 123]

[1014]

[1015] Under an argon atmosphere, 2.73 g of 4-(naphthalen-1-yl)-N-[4-(naphthalen-1-yl)phenyl]aniline, 2.20 g of Intermediate C, 0.118 g of tris(dibenzylideneacetone)dipalladium(0), 0.153 g of tri-tert-butylphosphonium tetrafluoroborate, 1.87 g of sodium tert-butoxide, and 36 mL of toluene were mixed and stirred at 110°C for 4 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 3.84 g of a white solid. The yield was 82%.

[1016] The obtained substance was subjected to mass spectrometry analysis (m / e=725 relative to molecular weight 725.31), and was identified as Compound Inv-10.

[1017] Synthesis Example 11: Synthesis of Compound Inv-11

[1018] [Chemical Formula 124]

[1019]

[1020] Under an argon atmosphere, 3.51 g of N-[4-(naphthalen-1-yl)phenyl][1,1'-biphenyl]-4-amine, 3.21 g of Intermediate C, 0.172 g of tris(dibenzylideneacetone)dipalladium(0), 0.223 g of tri-tert-butylphosphonium tetrafluoroborate, 2.72 g of sodium tert-butoxide, and 52 mL of toluene were mixed and stirred at 110°C for 4 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 4.65 g of a white solid. The yield was 73%.

[1021] The obtained substance was subjected to mass spectrometry analysis (m / e=675 relative to molecular weight 675.29), and was identified as compound Inv-11.

[1022] Synthesis Example 12: Synthesis of Compound Inv-12

[1023] [Chemical Formula 125]

[1024]

[1025] Under an argon atmosphere, 5.33 g of N-[4-(dibenzo[b,d]furan-1-yl)phenyl][1,1'-biphenyl]-4-amine, 4.40 g of Intermediate C, 0.236 g of tris(dibenzylideneacetone)dipalladium(0), 0.306 g of tri-tert-butylphosphonium tetrafluoroborate, 3.73 g of sodium tert-butoxide, and 72 mL of toluene were mixed and stirred at 110°C for 4 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 6.93 g of a white solid. The yield was 75%.

[1026] The obtained substance was subjected to mass spectrometry analysis (m / e=715 relative to molecular weight 715.29), and was identified as Compound Inv-12.

[1027] Synthesis Example 13: Synthesis of Compound Inv-13

[1028] [Chemical Formula 126]

[1029]

[1030] Under an argon atmosphere, 4.14 g of 4-(naphthalen-2-yl)-N-[4-(naphthalen-2-yl)phenyl]aniline, 3.34 g of Intermediate C, 0.179 g of tris(dibenzylideneacetone)dipalladium(0), 0.232 g of tri-tert-butylphosphonium tetrafluoroborate, 2.83 g of sodium tert-butoxide, and 54 mL of toluene were mixed and stirred at 110°C for 4 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 4.91 g of a white solid. The yield was 69%.

[1031] The obtained substance was subjected to mass spectrometry analysis (m / e=725 relative to molecular weight 725.31), and was identified as Compound Inv-13.

[1032] Synthesis Example 14: Synthesis of Compound Inv-14

[1033] [Chemical Formula 127]

[1034]

[1035] Under an argon atmosphere, 3.63 g of N-[4-(phenanthren-9-yl)phenyl]naphthalene-1-amine, 3.12 g of intermediate C, 0.168 g of tris(dibenzylideneacetone)dipalladium(0), 0.217 g of tri-tert-butylphosphonium tetrafluoroborate, 2.65 g of sodium tert-butoxide, and 51 mL of toluene were mixed and stirred at 110°C for 4 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 5.32 g of a white solid. The yield was 82%.

[1036] The obtained substance was subjected to mass spectrometry analysis (m / e=699, relative to a molecular weight of 699.29), and was identified as Compound Inv-14.

[1037] Synthesis Example 15: Synthesis of Compound Inv-15

[1038] [Chemical Formula 128]

[1039]

[1040] Under an argon atmosphere, 4.28 g of N-([1,1'-biphenyl]-4-yl)-3'-(9H-carbazol-9-yl)[1,1'-biphenyl]-4-amine, 2.99 g of Intermediate C, 0.161 g of tris(dibenzylideneacetone)dipalladium(0), 0.208 g of tri-tert-butylphosphonium tetrafluoroborate, 2.54 g of sodium tert-butoxide, and 48 mL of toluene were mixed and stirred at 110°C for 4 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 5.90 g of a white solid. The yield was 85%.

[1041] The obtained substance was subjected to mass spectrometry analysis (m / e=790, relative to molecular weight 790.33), and was identified as Compound Inv-15.

[1042] Synthesis Example 16: Synthesis of Compound Inv-16

[1043] [Chemical Formula 129]

[1044]

[1045] Under an argon atmosphere, 3.96 g of N-([1,1'-biphenyl]-4-yl)-2'-(9H-carbazol-9-yl)[1,1'-biphenyl]-4-amine, 2.77 g of Intermediate C, 0.148 g of tris(dibenzylideneacetone)dipalladium(0), 0.192 g of tri-tert-butylphosphonium tetrafluoroborate, 2.35 g of sodium tert-butoxide, and 45 mL of toluene were mixed and stirred at 110°C for 4 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 4.89 g of a white solid. The yield was 76%.

[1046] The obtained substance was subjected to mass spectrometry analysis (m / e=790, relative to molecular weight 790.33), and was identified as Compound Inv-16.

[1047] Synthesis Example 17: Synthesis of Compound Inv-17

[1048] [Chemical Formula 130]

[1049]

[1050] Under an argon atmosphere, 5.39 g of N-[4-(dibenzo[b,d]furan-4-yl)phenyl]dibenzo[b,d]furan-1-amine, 4.31 g of Intermediate C, 0.232 g of tris(dibenzylideneacetone)dipalladium(0), 0.299 g of tri-tert-butylphosphonium tetrafluoroborate, 3.66 g of sodium tert-butoxide, and 70 mL of toluene were mixed and stirred at 110°C for 4 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 5.45 g of a white solid. The yield was 59%.

[1051] The obtained substance was subjected to mass spectrometry analysis (m / e=729, relative to molecular weight 729.27), and was identified as Compound Inv-17.

[1052] Synthesis Example 18: Synthesis of Compound Inv-18

[1053] [Chemical Formula 131]

[1054]

[1055] Synthesis of intermediate H

[1056] Under an argon atmosphere, 5.68 g (25.9 mmol) of 3-(naphthalene-1-yl)aniline, 6.58 g (25.9 mmol) of 1-iodonaphthalene, 474 mg (0.51 mmol) of tris(dibenzylideneacetone)dipalladium(0), 645 mg (1.03 mmol) of BINAP, 2.74 g (28.5 mmol) of sodium tert-butoxide, and 130 ml of toluene were added, and the mixture was heated and stirred at 110°C for 7 hours. After cooling, the mixture was filtered, and the resulting residue was purified by column chromatography to obtain 7.49 g of Intermediate H. The yield was 84%.

[1057] Synthesis of compound Inv-18

[1058] Under an argon atmosphere, 3.2 g of Intermediate H, 3.27 g of Intermediate C, 0.176 g of tris(dibenzylideneacetone)dipalladium (0), 0.222 g of tri-tert-butylphosphonium tetrafluoroborate, 2.70 g of sodium tert-butoxide, and 54 mL of toluene were mixed and stirred at 110°C for 4 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 6.05 g of a white solid. The yield was 68%.

[1059] The obtained substance was subjected to mass spectrometry analysis (m / e=650 relative to molecular weight 649.84), and was identified as compound Inv-18.

[1060] Synthesis Example 19: Synthesis of Compound Inv-19

[1061] [Chemical Formula 132]

[1062]

[1063] Synthesis of Intermediate I

[1064] Under an argon atmosphere, 2.19 g of aniline-2,3,4,5,6-d5 (22.33 mmol), 3.29 g (20.3 mmol) of bromobenzene-d5, 372 mg (0.41 mmol) of tris(dibenzylideneacetone)dipalladium(0), 506 mg of BINAP (0.812 mmol), 2.15 g (22.33 mmol) of sodium tert-butoxide, and 200 ml of toluene were added, and the mixture was heated and stirred at 100°C for 3 hours. After cooling, the mixture was filtered, and the resulting residue was purified by column chromatography to obtain 3.59 g of Intermediate I. The yield was 99%.

[1065] Synthesis of intermediates J and K

[1066] Under an argon atmosphere, 2.9 g of Intermediate I (16.18 mmol) and 55 ml of DMF were mixed, and 5.76 g (32.4 mmol) of N-bromosuccinimide was added at 0°C. Water and ethyl acetate were added for extraction, and the resulting organic layer was distilled off under reduced pressure to obtain Intermediate J. Intermediate J was used in the next reaction without purification.

[1067] Under an argon atmosphere, 6.41 g (19.12 mmol) of Intermediate J, 5.83 g (47.8 mmol) of phenylboronic acid, 406 mg (0.574 mmol) of bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)palladium(II) dichloride, and 1,4-dioxane (100 ml) were mixed, and an aqueous potassium phosphate solution was added. After heating and stirring at 110°C for 5 hours and cooling, the mixture was filtered and purified by column chromatography and recrystallization to obtain 3.9 g of Intermediate K. The yield of Intermediate K obtained via Intermediate J was 62% (two steps).

[1068] Synthesis of compound Inv-19

[1069] Under an argon atmosphere, 2.64 g of Intermediate J, 2.86 g of Intermediate C, 0.147 g of tris(dibenzylideneacetone)dipalladium (0), 0.186 g of tri-tert-butylphosphonium tetrafluoroborate, 1.08 g of sodium tert-butoxide, and 80 mL of toluene were mixed and stirred at 110°C for 7 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 3.29 g of a white solid. The yield was 65%.

[1070] The obtained substance was subjected to mass spectrometry analysis (m / e=633, relative to molecular weight 633.33), and was identified as compound Inv-19.

[1071] Synthesis Example 20: Synthesis of Compound Inv-20

[1072] [Chemical Formula 133]

[1073]

[1074] Synthesis of intermediate L

[1075] Under an argon atmosphere, 8.61 g of 1-bromo-4-iodobenzene-2,3,5,6-d4 (30 mmol), 8.63 g (31.5 mmol) of [1,1':2',1''-terphenyl]-4'-ylboronic acid, 1.39 g (1.2 mmol) of tetrakis(triphenylphosphine)palladium(0), 30 mL of a 2M aqueous solution of tripotassium phosphate, and 150 mL of dioxane were added, and the mixture was heated and stirred at 80°C for 7 hours. Water was added to precipitate the resulting solid, which was extracted with dichloromethane and washed. The solvent was distilled off, and the resulting residue was purified by column chromatography to obtain Intermediate L (7.3 g). The yield was 63%.

[1076] Synthesis of compound Inv-20

[1077] Under an argon atmosphere, 2.64 g of Intermediate K, 3.27 g of Intermediate L, 0.147 g of tris(dibenzylideneacetone)dipalladium (0), 0.186 g of tri-tert-butylphosphonium tetrafluoroborate, 1.08 g of sodium tert-butoxide, and 80 mL of toluene were mixed and stirred at 110°C for 7 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 4.11 g of a white solid. The yield was 80%.

[1078] The obtained substance was subjected to mass spectrometry analysis (m / e=637 relative to molecular weight 637.35), and was found to be compound Inv-20.

[1079] Synthesis Example 21: Synthesis of Compound Inv-21

[1080] [Chemical Formula 134]

[1081]

[1082] Synthesis of intermediate M

[1083] Under an argon atmosphere, 6.0 g (15.41 mmol) of Intermediate L, 23.12 mL of a 1M LiHMDS toluene solution, 282 mg (0.31 mmol) of tris(dibenzylideneacetone)dipalladium(0), 179 mg (0.62 mmol) of tri-tert-butylphosphonium tetrafluoroborate, and 77 mL of toluene were added, and the mixture was heated and stirred at 110°C for 7 hours. Hydrochloric acid was added, and the mixture was extracted with toluene. The resulting residue was purified by column chromatography to obtain 3.45 g of Intermediate M. The yield was 69%.

[1084] Synthesis of intermediate N

[1085] Under an argon atmosphere, 3.45 g of Intermediate M (10.6 mmol), 2.69 g (10.6 mmol) of 1-iodonaphthalene, 194 mg (0.212 mmol) of tris(dibenzylideneacetone)dipalladium(0), 264 mg (0.424 mmol) of BINAP, 1.12 g (11.6 mmol) of sodium tert-butoxide, and 53 ml of toluene were added, and the mixture was heated and stirred at 100°C for 8 hours. The residue was purified by column chromatography to obtain 3.8 g of Intermediate N. The yield was 80%.

[1086] Synthesis of intermediate O

[1087] Under an argon atmosphere, 2.87 g (10 mmol) of 1-bromo-4-iodobenzene-2,3,5,6-d4, 1.81 g (10.5 mmol) of 1-naphthaleneboronic acid, 462 mg (0.4 mmol) of tetrakis(triphenylphosphine)palladium(0), 10 mL of a 2M aqueous solution of tripotassium phosphate, and 50 mL of dioxane were added, and the mixture was heated and stirred at 80°C for 7 hours. The reaction solution was purified by column chromatography to obtain Intermediate O (2.87 g). The yield was 99%.

[1088] Synthesis of compound Inv-21

[1089] Under an argon atmosphere, 1.82 g of Intermediate N, 1.39 g of Intermediate O, 0.074 g of tris(dibenzylideneacetone)dipalladium (0), 0.094 g of tri-tert-butylphosphonium tetrafluoroborate, 0.542 g of sodium tert-butoxide, and 40 mL of toluene were mixed and stirred at 110°C for 7 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 1.70 g of a white solid. The yield was 64%.

[1090] The obtained substance was subjected to mass spectrometry analysis (m / e=657, relative to molecular weight 657.33), and was found to be compound Inv-21.

[1091] Synthesis Example 22: Synthesis of Compound Inv-22

[1092] [Chemical Formula 135]

[1093]

[1094] Synthesis of intermediate P

[1095] In the synthesis of intermediate O, 1-naphthaleneboronic acid was replaced with phenylboronic acid, and intermediate P was obtained by the same operation. The yield was 97%.

[1096] Synthesis of compound Inv-22

[1097] Under an argon atmosphere, 2.03 g of Intermediate N, 1.28 g of Intermediate P, 0.082 g of tris(dibenzylideneacetone)dipalladium (0), 0.104 g of tri-tert-butylphosphonium tetrafluoroborate, 0.61 g of sodium tert-butoxide, and 45 mL of toluene were mixed and stirred at 110°C for 7 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization from a mixed solvent of toluene and hexane to obtain 2.00 g of a white solid. The yield was 73%.

[1098] The obtained substance was subjected to mass spectrometry analysis (m / e=607, relative to molecular weight 607.31), and was found to be compound Inv-22.

[1099] Description of Reference Numerals

[1100] 1.11: Organic EL components

[1101] 2: Substrate

[1102] 3: Anode

[1103] 4: cathode

[1104] 5: Luminous layer

[1105] 6: Hole transport region (hole transport layer)

[1106] 6a: Hole injection layer

[1107] 6b: 1st hole transport layer

[1108] 6c: Second hole transport layer

[1109] 7: Electron transport region (electron transport layer)

[1110] 7a: 1st electron transport layer

[1111] 7b: Second electron transport layer

[1112] 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 represents a group represented by any one of formulas (10) to (14), In the formula, R 11 ~R 15 、R 21 ~R 26 、R 41 ~R 48 、R 51 ~R 62 and R 71 ~R 78 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a halogen atom, a cyano group, a nitro group, 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, R 31 ~R 35 Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, X is an oxygen atom, a sulfur atom or NR 81 , R 81 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. Wherein, Selected from R 11 to R 15 One of them is a single bond bonded to *c, Selected from R 21 ~R 26 One of them is a single bond bonded to *d, and the other selected from R 21 ~R 26 is a single bond bonded to *e Selected from R 45 to R 48 One of them is a single bond bonded to *f, Selected from R 59 to R 62 One of them is a single bond bonded to *g, Selected from R 75 ~R 78 and R 81 One of them is a single bond bonded to the *i *h is bonded to one selected from carbon atoms *4 to *8, ** represents the bonding position to the central nitrogen atom, m is 0 or 1, and n is 0 or 1, In formulas (10) to (12) and (14), when m is 0 and n is 0, *e is bonded to the central nitrogen atom; when m is 0 and n is 1, *c is bonded to the central nitrogen atom; when m is 1 and n is 0, *e is bonded to one selected from R 11 ~R 15 and is bonded to one of them. In formula (13), when m is 0 and n is 1, *c is bonded to the central nitrogen atom, and when m is 1 and n is 0, *e is bonded to one selected from R 11 ~R 15 , excluding the case where m is 0 and n is 0 In formula (14), when m is 0 and n is 1, and when m is 1 and n is 0, one selected from R 75 ~R 78 is a single bond bonded to the *i key, R selected from those other than the said single bond 11 ~R 15 Two adjacent ones selected from R other than any of the above single bonds 21 ~R 26 Two adjacent ones selected from R 31 ~R 35 Two adjacent ones selected from R other than the said single bond 41 ~R 48 Two adjacent ones selected from R other than the said single bond 51 ~R 62 Two adjacent ones selected from R other than the said single bond 71 ~R 78 Two adjacent ones among them do not bond to each other and thus do not form a ring structure Benzene ring A is not crosslinked with benzene ring B, benzene ring A with benzene ring C, benzene ring B with benzene ring C, benzene ring A with the naphthalene ring, and benzene ring B with the naphthalene ring, *a is bonded to one selected from carbon atoms *1 to *3, R 1 ~R 4 Each independently represents a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Wherein, Selected from R 1 ~R 4 One of them is a single bond bonded to *b, R selected from single bonds that are not bonded to *b 1 ~R 4 Two adjacent ones among them are not bonded to each other, so no ring structure is formed R 5 to R 9 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted phenyl group Wherein, Selected from R 5 to R 9 Two adjacent ones selected therefrom may each independently bond to each other to form a substituted or unsubstituted ring structure, or may also not bond to each other, thus not forming a ring structure.

2. The compound according to claim 1, wherein Ar 1 and Ar 2 each independently represents a group represented by any one of formulas (20) to (24), In the formula, R 11 to R 15 , R 21 , R 22 , R 24 , R 25 , R 31 to R 35 , R 41 to R 48 , R 51 to R 62 , R 71 to R 78 , *f, *g, *h, *i, X, **, m, n, benzene ring A, benzene ring B and benzene ring C are as defined in formula (1).

3. The compound according to claim 1 or 2, wherein, R 45 or R 46 is a single bond bonded to *f, R 60 or R 61 is a single bond bonded to *g *h is bonded to carbon atom *8.

4. The compound according to any one of claims 1 to 3, wherein In formulas (10) to (12) and (14), m is 0 and n is 0.

5. The compound according to any one of claims 1 to 3, wherein m is 1 and n is 1.

6. The compound according to any one of claims 1 to 3, wherein m is 0 and n is 1.

7. The compound according to any one of claims 1 to 6, wherein Ar 1 and Ar 2 each independently represents a group represented by any of formulas (10), (11) and (14).

8. The compound according to any one of claims 1 to 7, wherein, Ar 1 and Ar 2 At least one of them is a group represented by the formula (11).

9. The compound according to any one of claims 1 to 8, wherein X is an oxygen atom.

10. The compound according to any one of claims 1 to 9, wherein, R 45 is a single bond bonded to *f.

11. The compound according to any one of claims 1 to 10, wherein, R 75 is a single bond bonded to *i.

12. The compound according to any one of claims 1 to 11, wherein, *a is bonded to carbon atom *3.

13. The compound according to any one of claims 1 to 12, wherein, R 2 or R 3 is a single bond bonded to *b.

14. The compound according to any one of claims 1 to 13, wherein, R which is not a single bond bonded to *b 1 ~R 4 All are hydrogen atoms.

15. The compound according to any one of claims 1 to 14, wherein, R 5 ~R 9 All are hydrogen atoms.

16. The compound according to any one of claims 1 to 15, wherein, The compound contains at least one deuterium atom.

17. A material for an organic electroluminescent element, which has the compound according to any one of claims 1 to 16.

18. An organic electroluminescent element, which has a cathode, an anode, and an organic layer located between the cathode and the anode, the organic layer contains a light-emitting layer, and at least one layer of the organic layer contains the compound according to any one of claims 1 to 16.

19. The organic electroluminescent element according to claim 18, wherein, The organic layer contains a hole transport region between the anode and the light-emitting layer, and the hole transport region contains the compound.

20. The organic electroluminescent element according to claim 19, wherein, The hole transport region contains 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.

21. The organic electroluminescent element according to claim 20, wherein, The second hole transport layer contains the compound.

22. The organic electroluminescent element according to claim 20 or 21, wherein, The second hole transport layer is adjacent to the light-emitting layer.

23. The organic electroluminescent element according to any one of claims 18 to 22, wherein The light-emitting layer contains a fluorescent dopant.

24. The organic electroluminescent element according to any one of claims 18 to 22, wherein, The light-emitting layer contains a phosphorescent dopant.

25. An electronic device, which has the organic electroluminescent element according to any one of claims 18 to 24.

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