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

Abstract

A compound represented by formula (1). # imgabs0 #

Description

Technical Field

[0001] The present invention relates to novel compounds, materials for organic electroluminescent elements, organic electroluminescent elements, and electronic devices. Background Art

[0002] When a voltage is applied to an organic electroluminescent element (hereinafter also referred to as an organic EL element), holes are injected from the anode and electrons are injected from the cathode into the light-emitting layer, respectively. Subsequently, in the light-emitting layer, the injected holes and electrons recombine to form excitons.

[0003] The element performance of conventional organic EL elements is not yet sufficient. In order to improve the element performance, the materials used in organic EL elements have been gradually improved, but further high performance is still required.

[0004] Prior Art Documents

[0005] Patent Documents

[0006] Patent Document 1: U.S. Patent Application Publication No. 2021 / 0147375

[0007] Patent Document 2: Korean Patent Publication No. 2019-136802

[0008] Patent Document 3: International Publication No. 2021 / 25372

[0009] Patent Document 4: Korean Patent Publication No. 2017-136391 Summary of the Invention

[0010] An object of the present invention is to provide a high-performance organic EL element and a compound capable of realizing the organic EL element.

[0011] According to the present invention, the following compounds and the like are provided.

[0012] 1. A compound represented by the following formula (1),

[0013] [Chemical Formula 1]

[0014]

[0015] In formula (1),

[0016] X 11 is an oxygen atom or a sulfur atom.

[0017] One or more groups each composed of two or more adjacent ones of R 11 to R 17 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other.

[0018] R that do not bond to each other 11 ~R 17 Each is independently a hydrogen atom or substituent R.

[0019] One or more groups of two or more adjacent ones among R1 to R4 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.

[0020] R1 to R4 that do not bond to each other are each independently:[[]]

[0021] A hydrogen atom,[[]]

[0022] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[0023] A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.

[0024] From R 21 ~R 27 One or more groups 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.

[0025] R that do not bond to each other 21 ~R 27 Each is independently a hydrogen atom or substituent R.

[0026] R 28 and R 29 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. Among them, when R 28 and R 29 bond to each other to form a substituted or unsubstituted fused ring, there is no case where a 9,9-spirobifluorene ring is formed together with the fluorene ring to which R 28 and R 29 are bonded.

[0027] At least one of R 28 and R 29 that do not bond to each other is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0028] R 28 and R 29 that do not bond to each other and are not the aforementioned substituted or unsubstituted alkyl group having 1 to 50 carbon atoms are each independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0029] From R 31 ~R 37One or more groups each composed of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.

[0030] R that are not bonded to each other 31 ~R 37 Each independently is a hydrogen atom or a substituent R.

[0031] R 38 and R 39 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other. Among them, when R 38 and R 39 are bonded to each other to form a substituted or unsubstituted fused ring, there is no case where a 9,9-spirobifluorene ring is formed together with the fluorene ring to which R 38 and R 39 are bonded.

[0032] R that are not bonded to each other 38 and R 39 At least one of them is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0033] R that are not bonded to each other and are not the aforementioned substituted or unsubstituted alkyl group having 1 to 50 carbon atoms 38 and R 39 Each independently is a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

[0034] L 11 、L 21 and L 31 Each independently is:

[0035] A single bond, or

[0036] A substituted or unsubstituted arylene group having 6 to 12 ring-forming carbon atoms.

[0037] n11 is an integer from 0 to 3.

[0038] When n11 is 0, (L 11 ) n11 is a single bond.

[0039] When n11 is 2 or 3, multiple L 11 are connected in series with each other, and the tricyclic fused skeleton is bonded to the L 11 farthest from the benzene skeleton. Multiple L 11 can be the same or different.

[0040] n21 is an integer from 0 to 3.

[0041] When n21 is 0, (L 21 )n21 is a single bond.

[0042] When n21 is 2 or 3, multiple Ls 21 are connected in series with each other, and the fluorene skeleton is bonded to the L farthest from the nitrogen atom. 21 Multiple Ls 21 may be the same or different.

[0043] n31 is an integer from 0 to 3.

[0044] When n31 is 0, (L 31 ) n31 is a single bond.

[0045] When n31 is 2 or 3, multiple Ls 31 are connected in series with each other, and the fluorene skeleton is bonded to the L farthest from the nitrogen atom. 31 Multiple Ls 31 may be the same or different.

[0046] The substituent R is selected from:

[0047] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0048] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0049] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0050] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0051] -Si(R 901 )(R 902 )(R 903 ),

[0052] -O-(R 904 ),

[0053] -S-(R 905 ),

[0054] -N(R 906 )(R 907 ),

[0055] a halogen atom, a cyano group, a nitro group,

[0056] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0057] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0058] When there are two or more substituents R, the two or more substituents R may be the same or different from each other.

[0059] R 901 ~R 907 Each independently represents:

[0060] a hydrogen atom,

[0061] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0062] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0063] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0064] a monovalent heterocyclic group having 5 to 50 ring atoms which may be substituted or unsubstituted.

[0065] R 901 ~R 907 When there are two or more of each, two or more Rs 901 ~R 907 each may be the same or different.

[0066] According to the present invention, a high-performance organic EL element and a compound capable of realizing the organic EL element can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0067] Figure 1 : A diagram showing a schematic configuration of an organic EL element according to one aspect of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0068] [Definitions]

[0069] In the present specification, the hydrogen atom includes isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

[0070] In the present specification, in a chemical structural formula, at a bondable position where symbols such as "R" and "D" representing a deuterium atom are not explicitly shown, a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is bonded.

[0071] 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., monocyclic compounds, polycyclic compounds, crosslinked compounds, carbocyclic compounds, and heterocyclic compounds). When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbon atoms. The "number of ring-forming carbon atoms" described below is the same unless otherwise specified. For example, the number of ring-forming carbon atoms in a benzene ring is 6, the number of ring-forming carbon atoms in a naphthalene ring is 10, the number of ring-forming carbon atoms in a pyridine ring is 5, and the number of ring-forming carbon atoms in a furan ring is 4. Additionally, for example, the number of ring-forming carbon atoms in 9,9-diphenylfluorenyl is 13, and the number of ring-forming carbon atoms in 9,9'-spirobifluorenyl is 25.

[0072] In addition, when, for example, an alkyl group is substituted as a substituent on a benzene ring, the number of carbon atoms in the alkyl group is not included in the number of ring-forming carbon atoms of the benzene ring. Therefore, the number of ring-forming carbon atoms in a benzene ring substituted with an alkyl group is 6. Additionally, when, for example, an alkyl group is substituted as a substituent on a naphthalene ring, the number of carbon atoms in the alkyl group is not included in the number of ring-forming carbon atoms of the naphthalene ring. Therefore, the number of ring-forming carbon atoms in a naphthalene ring substituted with an alkyl group is 10.

[0073] 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., monocyclic, polycyclic, and ring assemblies). Atoms that do not form a ring (e.g., hydrogen atoms that cap the bonds of atoms forming the ring) and atoms contained in the substituent when the ring is substituted with a substituent are not included in the number of ring-forming atoms. The "number of ring-forming atoms" described below is the same unless otherwise specified. For example, the number of ring-forming atoms in a pyridine ring is 6, the number of ring-forming atoms in a quinazoline ring is 10, and the number of ring-forming atoms in a furan ring is 5. For example, the hydrogen atoms bonded to a pyridine ring or the number of atoms constituting a substituent are not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms in a pyridine ring bonded with a hydrogen atom or a substituent is 6. Additionally, for example, the hydrogen atoms bonded to the carbon atoms of a quinoline ring or the atoms constituting a substituent are not included in the number of quinoline ring-forming atoms. Therefore, the number of ring-forming atoms in a quinoline ring bonded with a hydrogen atom or a substituent is 10.

[0074] In this specification, in the expression "ZZ group having XX to YY carbon atoms, which may be substituted or unsubstituted", "XX to YY carbon atoms" represents the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms in the substituent when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0075] In this specification, the "number of atoms XX to YY in the substituted or unsubstituted ZZ group" in the expression means the number of atoms in the ZZ group when it is unsubstituted, and does not include the number of atoms in the substituent when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0076] In this specification, an unsubstituted ZZ group means the case where the "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group means the case where the "substituted or unsubstituted ZZ group" is a "substituted ZZ group".

[0077] In this specification, "unsubstituted" in the case of the "substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom or a tritium atom.

[0078] In addition, in this specification, "substituted" in the case of the "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. "Substituted" in the case of the "BB group substituted by the AA group" also means that one or more hydrogen atoms in the BB group are replaced by the AA group.

[0079] "Substituents described in this specification"

[0080] Hereinafter, the substituents described in this specification will be described.

[0081] Unless otherwise specified in this specification, the number of ring-forming carbon atoms of the "unsubstituted aryl" described in this specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18.

[0082] Unless otherwise specified in this specification, the number of ring-forming atoms of the "unsubstituted heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18.

[0083] Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkyl" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6.

[0084] Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkenyl" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6.

[0085] Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkynyl" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6.

[0086] Unless otherwise specified in this specification, the number of ring-forming carbon atoms of the "unsubstituted cycloalkyl" described in this specification is 3 to 50, preferably 3 to 20, more preferably 3 to 6.

[0087] Unless otherwise specified in this specification, the number of ring-forming carbon atoms of the "unsubstituted arylene" described in this specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18.

[0088] Unless otherwise specified in this specification, the number of ring-forming atoms of the "unsubstituted divalent heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18.

[0089] Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkylene" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6.

[0090] · "Substituted or unsubstituted aryl"

[0091] As specific examples (specific example group G1) of the "substituted or unsubstituted aryl" described in this specification, the following unsubstituted aryls (specific example group G1A) and substituted aryls (specific example group G1B) can be cited, etc. (In this text, the unsubstituted aryl means the case where the "substituted or unsubstituted aryl" is "unsubstituted aryl", and the substituted aryl means the case where the "substituted or unsubstituted aryl" is "substituted aryl".) In this specification, when only "aryl" is mentioned, it includes both "unsubstituted aryl" and "substituted aryl".

[0092] "Substituted aryl" means that one or more hydrogen atoms of the "unsubstituted aryl" are replaced by substituents. As the "substituted aryl", 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 can be cited, etc. It should be noted that the examples of the "unsubstituted aryl" and the "substituted aryl" listed here are only examples, and the "substituted aryl" described in this specification also includes groups in which the hydrogen atoms bonded to the carbon atoms of the aryl itself in the "substituted aryl" in the following specific example group G1B 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.

[0093] · Unsubstituted aryl (specific example group G1A):

[0094] Phenyl,

[0095] p - Biphenyl,

[0096] m - Biphenyl,

[0097] o - Biphenyl,

[0098] p - terphenyl - 4 - yl,

[0099] p - terphenyl - 3 - yl,

[0100] p - terphenyl - 2 - yl,

[0101] m - terphenyl - 4 - yl,

[0102] m - terphenyl - 3 - yl,

[0103] m - terphenyl - 2 - yl,

[0104] o - terphenyl - 4 - yl,

[0105] o - terphenyl - 3 - yl,

[0106] o - terphenyl - 2 - yl,

[0107] 1 - naphthyl,

[0108] 2 - naphthyl,

[0109] anthryl,

[0110] benzoanthryl,

[0111] phenanthryl,

[0112] benzophenanthryl,

[0113] phenalenyl,

[0114] pyrenyl,

[0115] - yl,

[0116] benzo - yl,

[0117] triphenylenyl,

[0118] benzotriphenylenyl,

[0119] tetracenyl,

[0120] pentacenyl,

[0121] fluorenyl,

[0122] 9,9’ - spirobifluorenyl,

[0123] benzofluorenyl,

[0124] dibenzofluorenyl,

[0125] fluoranthenyl,

[0126] benzofluoranthenyl,

[0127] perylenyl, and

[0128] 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).

[0129] [Chemical formula 2]

[0130]

[0131] · Substituted aryl group (specific example group G1B): o-tolyl,

[0132] m-tolyl,

[0133] p-tolyl,

[0134] p-xylyl,

[0135] m-xylyl,

[0136] o-xylyl,

[0137] p-isopropylphenyl,

[0138] m-isopropylphenyl,

[0139] o-isopropylphenyl,

[0140] p-tert-butylphenyl,

[0141] m-tert-butylphenyl,

[0142] o-tert-butylphenyl,

[0143] 3,4,5-trimethylphenyl,

[0144] 9,9-dimethylfluorenyl,

[0145] 9,9-diphenylfluorenyl

[0146] 9,9-bis(4-methylphenyl)fluorenyl,

[0147] 9,9-bis(4-isopropylphenyl)fluorenyl,

[0148] 9,9-bis(4-tert-butylphenyl)fluorenyl,

[0149] cyanophenyl,

[0150] triphenylsilylphenyl,

[0151] trimethylsilylphenyl,

[0152] phenylnaphthyl,

[0153] naphthylphenyl, and

[0154] A group in which one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the aforementioned general formulas (TEMP-1) to (TEMP-15) are replaced by substituents.

[0155] · "Substituted or unsubstituted heterocyclic group"

[0156] The "heterocyclic group" described in this specification is a cyclic group containing at least one heteroatom among 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.

[0157] The "heterocyclic group" described in this specification is a monocyclic group or a fused-ring group.

[0158] The "heterocyclic group" described in this specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0159] 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. (In this text, an unsubstituted heterocyclic group means the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and a substituted heterocyclic group means the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when simply referring to a "heterocyclic group", it includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group".

[0160] A "substituted heterocyclic group" means a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by 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 replaced, 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 examples of the "substituted heterocyclic group" listed here are only examples, and the "substituted heterocyclic group" described in this specification includes groups in which hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself in the "substituted heterocyclic group" of specific example group G2B are further replaced by substituents, and groups in which hydrogen atoms of the substituents in the "substituted heterocyclic group" of specific example group G2B are further replaced by substituents.

[0161] 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).

[0162] The specific example group G2B includes, for example, a substituted heterocyclic group containing a nitrogen atom (specific example group G2B1), a substituted heterocyclic group containing an oxygen atom (specific example group G2B2), a substituted heterocyclic group containing a sulfur atom (specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) are replaced with substituents (specific example group G2B4).

[0163] · Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):

[0164] Pyrrolyl,

[0165] Imidazolyl,

[0166] Pyrazolyl,

[0167] Triazolyl,

[0168] Tetrazolyl,

[0169] Oxazolyl,

[0170] Isoxazolyl,

[0171] Oxadiazolyl,

[0172] Thiazolyl,

[0173] Isothiazolyl,

[0174] Thiadiazolyl,

[0175] Pyridyl,

[0176] Pyridazinyl,

[0177] Pyrimidinyl,

[0178] Pyrazinyl,

[0179] Triazinyl,

[0180] Indolyl,

[0181] Isoindolyl,

[0182] Indolizinyl,

[0183] Quinolizinyl,

[0184] Quinolyl,

[0185] Isoquinolyl,

[0186] Cinnolinyl,

[0187] Phthalazinyl,

[0188] Quinazolinyl,

[0189] Quinoxalinyl,

[0190] benzimidazolyl,

[0191] indazolyl,

[0192] phenanthrolinyl,

[0193] phenanthridinyl,

[0194] acridinyl,

[0195] phenoxazinyl,

[0196] carbazolyl,

[0197] benzocarbazolyl,

[0198] morpholinyl,

[0199] phenoxazinyl,

[0200] phenothiazinyl,

[0201] azacarbazolyl, and diazacarbazolyl.

[0202] · Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): furyl,

[0203] oxazolyl,

[0204] isoxazolyl,

[0205] oxadiazolyl,

[0206] xanthenyl,

[0207] benzofuryl,

[0208] isobenzofuryl,

[0209] dibenzofuryl,

[0210] naphthobenzofuryl,

[0211] benzoxazolyl,

[0212] benzoisoxazolyl,

[0213] phenoxazinyl,

[0214] morpholinyl,

[0215] dinaphthofuryl,

[0216] azadibenzofuryl,

[0217] diazadibenzofuryl,

[0218] azanonaphthobenzofuryl, and

[0219] diazanonaphthobenzofuryl.

[0220] · Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): Thienyl,

[0221] Thiazolyl,

[0222] Isothiazolyl,

[0223] Thiadiazolyl,

[0224] Benzothienyl,

[0225] Isobenzothienyl,

[0226] Dibenzothienyl,

[0227] Naphthobenzothienyl, benzothiazolyl,

[0228] Benzisothiazolyl,

[0229] Phenothiazinyl,

[0230] Dinaphthothiophenyl,

[0231] Azadibenzothienyl,

[0232] Diazadibenzothienyl,

[0233] Azanaphthobenzothienyl, and

[0234] Diazanaphthobenzothienyl.

[0235] · 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):

[0236] [Chemical formula 4]

[0237]

[0238] [Chemical formula 5]

[0239]

[0240] In the aforementioned general formulas (TEMP-16) to (TEMP-33), X A and Y AEach independently represents an oxygen atom, a sulfur atom, NH, or CH2. Among them, X A and Y A at least one of which is an oxygen atom, a sulfur atom, or NH.

[0241] In the aforementioned 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 aforementioned general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0242] · Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1):

[0243] (9-Phenyl)carbazolyl,

[0244] (9-Biphenyl)carbazolyl,

[0245] (9-Phenyl)phenylcarbazolyl,

[0246] (9-Naphthyl)carbazolyl,

[0247] Diphenylcarbazol-9-yl,

[0248] Phenylcarbazol-9-yl,

[0249] Methylbenzimidazolyl,

[0250] Ethylbenzimidazolyl,

[0251] Phenyltriazinyl,

[0252] Biphenyltriazinyl,

[0253] Diphenyltriazinyl,

[0254] Phenylquinazolinyl, and

[0255] Biphenylquinazolinyl.

[0256] · Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2):

[0257] Phenyldibenzofuranyl,

[0258] Methyldibenzofuranyl,

[0259] tert-Butyldibenzofuranyl, and

[0260] A monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0261] · Substituted heterocyclic groups containing a sulfur atom (specific example group G2B3):

[0262] Phenyldibenzothienyl,

[0263] Methyldibenzothienyl,

[0264] tert-Butyldibenzothienyl, and

[0265] A monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0266] · A group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structures represented by the aforementioned general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific example group G2B4):

[0267] The aforementioned "one or more hydrogen atoms of the monovalent heterocyclic group" means a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, X A and Y A when at least any one of them is NH, a hydrogen atom bonded to the nitrogen atom, and X A and Y A when one of them is CH2, one or more hydrogen atoms of the methylene group.

[0268] · "Substituted or unsubstituted alkyl"

[0269] 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. (In this article, unsubstituted alkyl means the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl means the case where "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when simply referring to "alkyl", it includes both "unsubstituted alkyl" and "substituted alkyl".

[0270] "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, and examples of substituted alkyl (specific example group G3B), etc. In this specification, the alkyl in "unsubstituted alkyl" means a chain-like alkyl. Therefore, "unsubstituted alkyl" includes straight-chain "unsubstituted alkyl" and branched-chain "unsubstituted alkyl". It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples, and the "substituted alkyl" described in this specification also includes groups in which the hydrogen atoms of the alkyl itself in the "substituted alkyl" of specific example group G3B 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.

[0271] · Unsubstituted alkyl (specific example group G3A):

[0272] Methyl,

[0273] Ethyl,

[0274] n-Propyl,

[0275] Isopropyl,

[0276] n-Butyl,

[0277] Isobutyl,

[0278] sec-Butyl, and

[0279] tert-Butyl.

[0280] · Substituted alkyl (specific example group G3B):

[0281] Heptafluoropropyl (including isomers),

[0282] Pentafluoroethyl,

[0283] 2,2,2-Trifluoroethyl, and

[0284] Trifluoromethyl.

[0285] · "Substituted or unsubstituted alkenyl"

[0286] 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 this specification, when simply referring to "alkenyl", it includes both "unsubstituted alkenyl" and "substituted alkenyl".

[0287] "Substituted alkenyl" means a group in which one or more hydrogen atoms in the "unsubstituted alkenyl" are replaced by substituents. As specific examples of the "substituted alkenyl", 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 examples, and the "substituted alkenyl" described in this specification also includes a group in which a hydrogen atom of the alkenyl itself in the "substituted alkenyl" of 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.

[0288] · Unsubstituted alkenyl (specific example group G4A):

[0289] Vinyl,

[0290] Allyl,

[0291] 1-Butenyl,

[0292] 2-Butenyl, and

[0293] 3-Butenyl.

[0294] · Substituted alkenyl (specific example group G4B):

[0295] 1,3-Butadienyl,

[0296] 1-Methylvinyl,

[0297] 1-Methylallyl,

[0298] 1,1-Dimethylallyl,

[0299] 2-Methylallyl, and

[0300] 1,2-Dimethylallyl.

[0301] · "Substituted or unsubstituted alkynyl"

[0302] 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 simply referring to "alkynyl", it includes both "unsubstituted alkynyl" and "substituted alkynyl".

[0303] "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.

[0304] · Unsubstituted alkynyl (specific example group G5A):

[0305] Ethynyl

[0306] · "Substituted or unsubstituted cycloalkyl"

[0307] As a specific example (specific example group G6) of the "substituted or unsubstituted cycloalkyl" described in this specification, the following unsubstituted cycloalkyl (specific example group G6A), 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 simply referring to "cycloalkyl", it includes both "unsubstituted cycloalkyl" and "substituted cycloalkyl".

[0308] "Substituted cycloalkyl" means a group in which one or more hydrogen atoms in the "unsubstituted cycloalkyl" are replaced by substituents. As specific examples of the "substituted cycloalkyl", groups in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl" (specific example group G6A) are replaced by substituents, and examples of substituted cycloalkyl (specific example group G6B) etc. can be cited. It should be noted that the examples of the "unsubstituted cycloalkyl" and the examples of the "substituted cycloalkyl" listed here are only one example, and the "substituted cycloalkyl" described in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atoms of the cycloalkyl itself in the "substituted cycloalkyl" of specific example group G6B are replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted cycloalkyl" of specific example group G6B are further replaced by substituents.

[0309] · Unsubstituted cycloalkyl (specific example group G6A):

[0310] Cyclopropyl,

[0311] Cyclobutyl,

[0312] Cyclopentyl,

[0313] Cyclohexyl,

[0314] 1 - Adamantyl,

[0315] 2 - Adamantyl,

[0316] 1 - Norbornyl, and

[0317] 2 - Norbornyl.

[0318] · Substituted cycloalkyl (specific example group G6B):

[0319] 4 - Methylcyclohexyl.

[0320] · "A group represented by -Si(R 901 )(R 902 )(R 903 )"

[0321] As specific examples (specific example group G7) of the group represented by -Si(R 901 )(R 902 )(R 903 ) described in this specification, the following can be cited:

[0322] -Si(G1)(G1)(G1),

[0323] -Si(G1)(G2)(G2),

[0324] -Si(G1)(G1)(G2),

[0325] -Si(G2)(G2)(G2),

[0326] -Si(G3)(G3)(G3), and

[0327] -Si(G6)(G6)(G6).

[0328] Here,

[0329] G1 is "substituted or unsubstituted aryl" described in specific example group G1.

[0330] G2 is "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0331] G3 is "substituted or unsubstituted alkyl" described in specific example group G3.

[0332] G6 is "substituted or unsubstituted cycloalkyl" described in specific example group G6.

[0333] The multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other.

[0334] - The plurality of G2s in -Si(G1)(G2)(G2) are the same as or different from each other.

[0335] - The plurality of G1s in -Si(G1)(G1)(G2) are the same as or different from each other.

[0336] - The plurality of G2s in -Si(G2)(G2)(G2) are the same as or different from each other.

[0337] - The plurality of G3s in -Si(G3)(G3)(G3) are the same as or different from each other.

[0338] - The plurality of G6s in -Si(G6)(G6)(G6) are the same as or different from each other.

[0339] · “-O-(R 904 ) group”

[0340] As a specific example (specific example group G8) of the -O-(R 904 ) group described in this specification, the following can be cited:

[0341] -O(G1),

[0342] -O(G2),

[0343] -O(G3), and

[0344] -O(G6).

[0345] Here,

[0346] G1 is the “substituted or unsubstituted aryl group” described in specific example group G1.

[0347] G2 is the “substituted or unsubstituted heterocyclic group” described in specific example group G2.

[0348] G3 is the “substituted or unsubstituted alkyl group” described in specific example group G3.

[0349] G6 is the “substituted or unsubstituted cycloalkyl group” described in specific example group G6.

[0350] · “-S-(R 905 ) group”

[0351] As a specific example (specific example group G9) of the -S-(R 905 ) group described in this specification, the following can be cited:

[0352] -S(G1),

[0353] -S(G2),

[0354] -S(G3), and

[0355] -S(G6).

[0356] Here,

[0357] G1 is the "substituted or unsubstituted aryl" described in Specific Example Group G1.

[0358] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0359] G3 is the "substituted or unsubstituted alkyl" described in Specific Example Group G3.

[0360] G6 is the "substituted or unsubstituted cycloalkyl" described in Specific Example Group G6.

[0361] · The group represented by "-N(R 906 )(R 907 )"

[0362] As specific examples (Specific Example Group G10) of the group represented by -N(R 906 )(R 907 ) described in this specification, the following can be cited:

[0363] -N(G1)(G1),

[0364] -N(G2)(G2),

[0365] -N(G1)(G2),

[0366] -N(G3)(G3), and

[0367] -N(G6)(G6).

[0368] Here,

[0369] G1 is the "substituted or unsubstituted aryl" described in Specific Example Group G1.

[0370] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0371] G3 is the "substituted or unsubstituted alkyl" described in Specific Example Group G3.

[0372] G6 is the "substituted or unsubstituted cycloalkyl" described in Specific Example Group G6.

[0373] The multiple G1s in -N(G1)(G1) are the same as or different from each other.

[0374] The multiple G2s in -N(G2)(G2) are the same as or different from each other.

[0375] The multiple G3s in -N(G3)(G3) are the same as or different from each other.

[0376] The plurality of G6 in -N(G6)(G6) are the same as or different from each other.

[0377] · "halogen atom"

[0378] 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.

[0379] · "substituted or unsubstituted fluoroalkyl"

[0380] The "substituted or unsubstituted fluoroalkyl" described in this specification means a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in the "substituted or unsubstituted alkyl" is replaced by a 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). Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted fluoroalkyl" is 1 to 50, preferably 1 to 30, more preferably 1 to 18. The "substituted fluoroalkyl" means 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 aforementioned "alkyl" (specific example group G3) are replaced by fluorine atoms can be cited.

[0381] · "substituted or unsubstituted haloalkyl"

[0382] As used herein, "substituted or unsubstituted haloalkyl" means 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. Unless otherwise specified herein, the number of carbon atoms in "unsubstituted haloalkyl" is 1 to 50, preferably 1 to 30, more preferably 1 to 18. "Substituted haloalkyl" means a group in which one or more hydrogen atoms of "haloalkyl" are replaced by substituents. It should be noted that "substituted haloalkyl" as described herein 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 examples of groups in which one or more hydrogen atoms in the aforementioned "alkyl" (specific example group G3) are replaced by halogen atoms. Haloalkyl is sometimes referred to as halogenated alkyl.

[0383] · "substituted or unsubstituted alkoxy"

[0384] Specific examples of "substituted or unsubstituted alkoxy" as described herein are groups represented by -O(G3), where G3 is "substituted or unsubstituted alkyl" described in specific example group G3. Unless otherwise specified herein, the number of carbon atoms in "unsubstituted alkoxy" is 1 to 50, preferably 1 to 30, more preferably 1 to 18.

[0385] · "substituted or unsubstituted alkylthio"

[0386] Specific examples of "substituted or unsubstituted alkylthio" as described herein are groups represented by -S(G3), where G3 is "substituted or unsubstituted alkyl" described in specific example group G3. Unless otherwise specified herein, the number of carbon atoms in "unsubstituted alkylthio" is 1 to 50, preferably 1 to 30, more preferably 1 to 18.

[0387] · "substituted or unsubstituted aryloxy"

[0388] Specific examples of "substituted or unsubstituted aryloxy" as described herein are groups represented by -O(G1), where G1 is "substituted or unsubstituted aryl" described in specific example group G1. Unless otherwise specified herein, the number of ring-constituting carbon atoms in "unsubstituted aryloxy" is 6 to 50, preferably 6 to 30, more preferably 6 to 18.

[0389] · "substituted or unsubstituted arylthio"

[0390] Specific examples of the "substituted or unsubstituted arylthio group" described in this specification are groups represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1. Unless otherwise specified in this specification, the ring-forming carbon atoms of the "unsubstituted arylthio group" are 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0391] · "Substituted or unsubstituted trialkylsilyl"

[0392] Specific examples of the "trialkylsilyl group" described in this specification are groups represented by -Si(G3)(G3)(G3), where G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3. The plurality of G3 in -Si(G3)(G3)(G3) are the same as or different from each other. Unless otherwise specified in this specification, the carbon atoms of each alkyl group of the "trialkylsilyl group" are 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0393] · "Substituted or unsubstituted aralkyl"

[0394] Specific examples of the "substituted or unsubstituted aralkyl" described in this specification are groups represented by -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3, and G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1. Therefore, "aralkyl" is a group in which a hydrogen atom of "alkyl" is replaced by an "aryl group" as a substituent, and is a form of "substituted alkyl". "Unsubstituted aralkyl" is "unsubstituted alkyl" substituted by "unsubstituted aryl", and the carbon atoms of "unsubstituted aralkyl" are 7 to 50, preferably 7 to 30, and more preferably 7 to 18 unless otherwise specified in this specification.

[0395] Specific examples of the "substituted or unsubstituted aralkyl" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl, etc.

[0396] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described in this specification is preferably phenyl, p-biphenylyl, m-biphenylyl, o-biphenylyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, pyrenyl, Groups such as a base, a triphenylene group, a fluorene group, a 9,9'-spirobifluorene group, a 9,9-dimethylfluorene group, and a 9,9-diphenylfluorene group.

[0397] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic groups described in this specification are preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an azadibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazol-4-yl group), a (9-biphenyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenyltriazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, and a phenyldibenzothiophenyl group, etc.

[0398] In this specification, unless otherwise specified in this specification, the carbazolyl group is specifically any one of the following groups.

[0399] [Chemical formula 6]

[0400]

[0401] In this specification, unless otherwise specified in this specification, the (9-phenyl)carbazolyl group is specifically any one of the following groups.

[0402] [Chemical formula 7]

[0403]

[0404] In the aforementioned general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents the bonding site.

[0405] In this specification, unless otherwise specified in this specification, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any one of the following groups.

[0406] [Chemical formula 8]

[0407]

[0408] In the aforementioned general formulas (TEMP-34) to (TEMP-41), * represents the bonding site.

[0409] Unless otherwise specified in this specification, the substituted or unsubstituted alkyl groups described in this specification are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.

[0410] · "Substituted or unsubstituted arylene"

[0411] Unless otherwise specified in this specification, the "substituted or unsubstituted arylene" described in this specification is a divalent group derived by removing one hydrogen atom from the aromatic ring of the above-mentioned "substituted or unsubstituted aryl". As specific examples (specific example group G12) of the "substituted or unsubstituted arylene", divalent groups derived by removing one hydrogen atom from the aromatic ring of the "substituted or unsubstituted aryl" described in specific example group G1 can be cited, etc.

[0412] · "Substituted or unsubstituted divalent heterocyclic group"

[0413] Unless otherwise specified in this specification, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom from the heterocyclic ring of the above-mentioned "substituted or unsubstituted heterocyclic group". As specific examples (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group", divalent groups derived by removing one hydrogen atom from the heterocyclic ring of the "substituted or unsubstituted heterocyclic group" described in specific example group G2 can be cited, etc.

[0414] · "Substituted or unsubstituted alkylene"

[0415] Unless otherwise specified in this specification, the "substituted or unsubstituted alkylene" described in this specification is a divalent group derived by removing one hydrogen atom from the alkyl chain of the above-mentioned "substituted or unsubstituted alkyl". As specific examples (specific example group G14) of the "substituted or unsubstituted alkylene", divalent groups derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl" described in specific example group G3 can be cited, etc.

[0416] Unless otherwise specified in this specification, the substituted or unsubstituted arylene described in this specification is preferably any group of the following general formulas (TEMP-42) to (TEMP-68).

[0417] [Chemical formula 9]

[0418]

[0419] [Chemical formula 10]

[0420]

[0421] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10Each is independently a hydrogen atom or a substituent.

[0422] In the aforementioned general formulas (TEMP-42) to (TEMP-52), * represents a bonding site.

[0423] [Chemical formula 11]

[0424]

[0425] In the aforementioned general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0426] The groups Q9 and Q 10 Can be bonded to each other via a single bond to form a ring.

[0427] In the aforementioned general formulas (TEMP-53) to (TEMP-62), * represents a bonding site.

[0428] [Chemical formula 12]

[0429]

[0430] In the aforementioned general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0431] In the aforementioned general formulas (TEMP-63) to (TEMP-68), * represents a bonding site.

[0432] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any group of the following general formulas (TEMP-69) to (TEMP-102).

[0433] [Chemical formula 13]

[0434]

[0435] [Chemical formula 14]

[0436]

[0437] [Chemical formula 15]

[0438]

[0439] In the aforementioned general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0440] [Chemical formula 16]

[0441]

[0442] [Chemical Formula 17]

[0443]

[0444] [Chemical Formula 18]

[0445]

[0446] [Chemical Formula 19]

[0447]

[0448] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0449] The above is the description of "substituents described in this specification".

[0450] · "The case of bonding to form a ring"

[0451] In this specification, the case of "one or more groups each consisting of two or more adjacent ones bonding to each other to form a substituted or unsubstituted monocyclic ring, or bonding to each other to form a substituted or unsubstituted fused ring, or not bonding to each other" means the case of "one or more groups each consisting of two or more adjacent ones bonding to each other to form a substituted or unsubstituted monocyclic ring", the case of "one or more groups each consisting of two or more adjacent ones bonding to each other to form a substituted or unsubstituted fused ring", and the case of "one or more groups each consisting of two or more adjacent ones not bonding to each other".

[0452] Hereinafter, the case of "one or more groups each consisting of two or more adjacent ones bonding to each other to form a substituted or unsubstituted monocyclic ring" and the case of "one or more groups each consisting of two or more adjacent ones bonding to each other to form a substituted or unsubstituted fused ring" in this specification (hereinafter, these cases are sometimes collectively referred to as "the case of bonding to form a ring") will be described. Taking the case of an anthracene compound represented by the following general formula (TEMP-103) having an anthracene ring as the parent skeleton as an example for description.

[0453] [Chemical Formula 20]

[0454]

[0455] For example, in the case of "one or more groups each consisting of two or more adjacent ones bonding to each other to form a ring" in R 921 ~R 930 , the group consisting of two adjacent ones as one group is the group of R 921 and R 922 , the group of R 922 and R 923 , the group of R 923 and R 924group, R 924 and R 930 group, R 930 and R 925 group, R 925 and R 926 group, R 926 and R 927 group, R 927 and R 928 group, R 928 and R 929 group, and R 929 and R 921 group.

[0456] The above "one or more groups" 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 bond to each other to form ring Q A and at the same time R 925 and R 926 bond to each other to form ring Q B In the case of, the anthracene compound represented by the foregoing general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0457] [Chemical formula 21]

[0458]

[0459] The case where a "group composed of two or more adjacent ones" forms a ring includes not only the case where groups composed of "two" adjacent ones bond as in the foregoing example, but also the case where groups composed of "three or more" adjacent ones bond. For example, it means that R 921 and R 922 bond to each other to form ring Q A and R 922 and R 923 bond to each other to form ring Q C , and a group composed of three mutually adjacent ones (R 921 , R 922 and R 923 ) bonds to each other to form a ring and condenses into an anthracene parent skeleton. At this time, the anthracene compound represented by the foregoing 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 .

[0460] [Chemical formula 22]

[0461]

[0462] The formed "monocyclic ring" or "fused ring", as the structure of the only formed ring, can be a saturated ring or an unsaturated ring. Even when "one group of the groups composed of 2 adjacent ones" forms a "monocyclic ring" or "fused ring", the "monocyclic ring" or "fused ring" can form a saturated ring or an unsaturated ring. For example, the ring Q formed in the aforementioned general formula (TEMP-104) A and the ring Q B are each a "monocyclic ring" or "fused ring". In addition, the ring Q formed in the aforementioned general formula (TEMP-105) A and the ring Q C are "fused rings". The ring Q A of the aforementioned general formula (TEMP-105) and the ring Q C form a fused ring by fusion through the ring Q A and the ring Q C If the ring Q A of the aforementioned general formula (TMEP-104) is a benzene ring, then the ring Q A is a monocyclic ring. If the ring Q A of the aforementioned general formula (TMEP-104) is a naphthalene ring, then the ring Q A is a fused ring.

[0463] In the "unsaturated ring", in addition to the aromatic hydrocarbon ring and the aromatic heterocyclic ring, it also includes an aliphatic hydrocarbon ring having an unsaturated bond, namely a double bond and / or a triple bond, in the ring structure (such as cyclohexene, cyclohexadiene, etc.), and a non-aromatic heterocyclic ring having an unsaturated bond (such as dihydropyran, imidazoline, pyrazoline, quinazine, indoline, isoindoline, etc.). The "saturated ring" includes an aliphatic hydrocarbon ring not having an unsaturated bond, or a non-aromatic heterocyclic ring not having an unsaturated bond.

[0464] As a specific example of the aromatic hydrocarbon ring, a structure in which the group listed as a specific example in the specific example group G1 is capped with a hydrogen atom can be cited.

[0465] As a specific example of the aromatic heterocyclic ring, a structure in which the aromatic heterocyclic group listed as a specific example in the specific example group G2 is capped with a hydrogen atom can be cited.

[0466] As a specific example of the aliphatic hydrocarbon ring, a structure in which the group listed as a specific example in the specific example group G6 is capped with a hydrogen atom can be cited.

[0467] "Forming a ring" means forming a ring only by a plurality of atoms of the mother skeleton, or by a plurality of atoms of the mother skeleton and further one or more arbitrary atoms. For example, the R 921 shown in the aforementioned general formula (TEMP-104) and the R 922 are bonded to each other to form the ring Q A which means the carbon atoms of the anthracene skeleton bonded by the R 921 , the R 922A carbon atom of a bonded anthracene skeleton and a ring formed with one or more arbitrary atoms. As a specific example, in the case of R 921 and R 922 forming ring Q A when, the carbon atoms of the anthracene skeleton bonded to R 921 and the carbon atoms of the anthracene skeleton bonded to R 922 form a monocyclic unsaturated ring with four carbon atoms, the ring formed by R 921 and R 922 is a benzene ring.

[0468] Here, the "arbitrary atom" is preferably at least one atom selected from carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms as long as not otherwise specified in this specification. For an arbitrary atom (for example, in the case of a carbon atom or a nitrogen atom), the bond that does not form a ring can be capped with a hydrogen atom or the like, or can be substituted with the "arbitrary substituent" described later. When an arbitrary atom other than a carbon atom is included, the formed ring is a heterocyclic ring.

[0469] The "one or more arbitrary atoms" constituting a monocyclic or fused ring are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and still more preferably 3 or more and 5 or less as long as not otherwise specified in this specification.

[0470] As long as not otherwise specified in this specification, "monocyclic" and "fused ring" preferably "monocyclic".

[0471] As long as not otherwise specified in this specification, "saturated ring" and "unsaturated ring" preferably "unsaturated ring".

[0472] As long as not otherwise specified in this specification, "monocyclic" is preferably a benzene ring.

[0473] As long as not otherwise specified in this specification, "unsaturated ring" is preferably a benzene ring.

[0474] In the case of "one or more groups composed of two or more adjacent ones" "bonding to each other to form a substituted or unsubstituted monocyclic ring", or "bonding to each other to form a substituted or unsubstituted fused ring", as long as not otherwise specified in this specification, it is preferably that one or more groups composed of two or more adjacent ones bond to each other to form a substituted or unsubstituted "unsaturated ring" composed of a plurality of atoms of the parent skeleton and one or more and 15 or less atoms selected from carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0475] The substituent when the above-mentioned "monocyclic" or "fused ring" has a substituent is, for example, the "arbitrary substituent" described later. Specific examples of the substituent when the above-mentioned "monocyclic" or "fused ring" has a substituent are the substituents described in the item "substituents described in this specification" above.

[0476] When the "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "arbitrary substituent" described below. Specific examples of the substituent when the "monocyclic ring" or "fused ring" has a substituent are the substituents described in the item "substituents described in this specification".

[0477] The above is the description of the case of "one or more groups each consisting of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case of "one or more groups each consisting of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted fused ring" (the case of "bonding to form a ring").

[0478] · Substituent in the case of "substituted or unsubstituted"

[0479] In one embodiment of the present specification, the substituent in the aforementioned "substituted or unsubstituted" case (sometimes referred to as "arbitrary substituent" in this specification) is selected from, for example, the following groups:

[0480] An unsubstituted alkyl group having 1 to 50 carbon atoms,

[0481] An unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0482] An unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0483] An unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[0484] -Si(R 901 )(R 902 )(R 903 ),

[0485] -O-(R 904 ),

[0486] -S-(R 905 ),

[0487] -N(R 906 )(R 907 ),

[0488] A halogen atom, a cyano group, a nitro group,

[0489] An unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and

[0490] An unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.

[0491] Here, each of R 901 to R 907 is independently:

[0492] A hydrogen atom,

[0493] An alkyl group having 1 to 50 carbon atoms, which may or may not be substituted,

[0494] A cycloalkyl group having 3 to 50 ring-forming carbon atoms, which may or may not be substituted,

[0495] An aryl group having 6 to 50 ring-forming carbon atoms, which may or may not be substituted, or

[0496] A heterocyclic group having 5 to 50 ring-forming atoms, which may or may not be substituted.

[0497] R 901 When there are two or more, two or more Rs 901 are the same as or different from each other,

[0498] R 902 When there are two or more, two or more Rs 902 are the same as or different from each other,

[0499] R 903 When there are two or more, two or more Rs 903 are the same as or different from each other,

[0500] R 904 When there are two or more, two or more Rs 904 are the same as or different from each other,

[0501] R 905 When there are two or more, two or more Rs 905 are the same as or different from each other,

[0502] R 906 When there are two or more, two or more Rs 906 are the same as or different from each other,

[0503] R 907 When there are two or more, two or more Rs 907 are the same as or different from each other.

[0504] In one embodiment, the substituent in the case of the aforementioned "substituted or unsubstituted" is a group selected from the following:

[0505] An alkyl group having 1 to 50 carbon atoms,

[0506] An aryl group having 6 to 50 ring-forming carbon atoms, and

[0507] A heterocyclic group having 5 to 50 ring-forming atoms.

[0508] In one embodiment, the substituent in the case of the aforementioned "substituted or unsubstituted" is a group selected from the following:

[0509] An alkyl group having 1 to 18 carbon atoms,

[0510] an aryl group having 6 to 18 ring carbon atoms, and

[0511] a heterocyclic group having 5 to 18 ring atoms.

[0512] Specific examples of each group of any of the above substituents are the specific examples of the substituents described in the item "Substituents described in this specification" above.

[0513] Unless otherwise specified in this specification, any adjacent substituents may form a "saturated ring" or an "unsaturated ring" with each other, preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, and more preferably a benzene ring.

[0514] Unless otherwise specified in this specification, any substituent may further have a substituent. The substituent further possessed by any substituent is the same as any of the above substituents.

[0515] In this specification, the numerical range of "AA to BB" means a 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.

[0516] [Compound of the new type]

[0517] The compound according to one aspect of the present invention is a compound represented by the following formula (1).

[0518] [Chemical formula 23]

[0519]

[0520] In formula (1),

[0521] X 11 is an oxygen atom or a sulfur atom.

[0522] One or more groups composed of two or more adjacent ones among R 11 ~R 17 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.

[0523] R 11 ~R 17 that are not bonded to each other are each independently a hydrogen atom or a substituent R.

[0524] One or more groups composed of two or more adjacent ones among R1 to R4 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.

[0525] R1 to R4, which do not bond to each other, are each independently:

[0526] a hydrogen atom,

[0527] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[0528] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.

[0529] One or more groups each composed of two or more adjacent ones of R 21 to R 27 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.

[0530] R 21 to R 27 are each independently a hydrogen atom or a substituent R.

[0531] R 28 and R 29 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. Among them, when R 28 and R 29 bond to each other to form a substituted or unsubstituted fused ring, there is no case where a 9,9-spirobifluorene ring is formed together with the fluorene ring to which R 28 and R 29 are bonded.

[0532] At least one of R 28 and R 29 that do not bond to each other is each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0533] R 28 and R 29 that do not bond to each other and are not the aforementioned substituted or unsubstituted alkyl group having 1 to 50 carbon atoms are each independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0534] One or more groups each composed of two or more adjacent ones of R 31 to R 37 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.

[0535] R 31 to R 37 are each independently a hydrogen atom or a substituent R.

[0536] R 38 and R 39Bond 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. Among them, R 38 and R 39 When bonding to each other to form a substituted or unsubstituted fused ring, there is no case where a fluorene ring bonded to R 38 and R 39 together forms a 9,9-spirobifluorene ring.

[0537] At least one of R 38 and R 39 that do not bond to each other is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0538] R 38 and R 39 that do not bond to each other and are not the aforementioned substituted or unsubstituted alkyl group having 1 to 50 carbon atoms are independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

[0539] L 11 、L 21 and L 31 are each independently:

[0540] A single bond, or

[0541] A substituted or unsubstituted arylene group having 6 to 12 ring-forming carbon atoms.

[0542] n11 is an integer from 0 to 3.

[0543] When n11 is 0, (L 11 ) n11 is a single bond.

[0544] When n11 is 2 or 3, multiple L 11 are connected in series with each other, and the tricyclic fused skeleton is bonded to the L 11 farthest from the benzene skeleton. Multiple L 11 can be the same or different.

[0545] n21 is an integer from 0 to 3.

[0546] When n21 is 0, (L 21 ) n21 is a single bond.

[0547] When n21 is 2 or 3, multiple L 21 are connected in series with each other, and the fluorene skeleton is bonded to the L 21 farthest from the nitrogen atom. Multiple L 21 can be the same or different.

[0548] n31 is an integer from 0 to 3.

[0549] When n31 is 0, (L 31 ) n31 is a single bond.

[0550] When n31 is 2 or 3, multiple Ls 31 are connected in series with each other, and the fluorene skeleton is bonded to the L 31 farthest from the nitrogen atom. Multiple Ls 31 can be the same or different.

[0551] The substituent R is selected from:

[0552] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0553] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0554] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0555] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0556] -Si(R 901 )(R 902 )(R 903 ),

[0557] -O-(R 904 ),

[0558] -S-(R 905 ),

[0559] -N(R 906 )(R 907 ),

[0560] a halogen atom, a cyano group, a nitro group,

[0561] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0562] a monovalent heterocyclic group having 5 to 50 ring atoms.

[0563] When there are two or more substituents R, the two or more substituents R can be the same or different from each other.

[0564] R 901 to R 907 are each independently:

[0565] a hydrogen atom,

[0566] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0567] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0568] Aryl having 6 to 50 ring-constituting carbon atoms, which may or may not be substituted, or

[0569] A monovalent heterocyclic group having 5 to 50 ring-constituting atoms, which may or may not be substituted.

[0570] R 901 ~R 907 When two or more of each exist, two or more R 901 ~R 907 may be the same or different from each other.

[0571] A compound according to one embodiment of the present invention has a specific structure represented by formula (1), and when used in an organic EL element, the element performance can be improved. Specifically, an organic EL device capable of being driven at a lower voltage and having high efficiency can be realized.

[0572] Regarding "wherein, when R 28 and R 29 are bonded to each other to form a substituted or unsubstituted condensed ring, there is no case where a 9,9-spirobifluorene ring is formed together with the fluorene ring to which R 28 and R 29 are bonded" in formula (1), an explanation is given.

[0573] R 28 and R 29 When bonded to each other to form a substituted or unsubstituted condensed ring, a carbon atom on the fluorene skeleton to which R 28 and R 29 are bonded forms a ring with an arbitrary atom (preferably at least one atom selected from carbon atom, nitrogen atom, oxygen atom, and sulfur atom). It is obvious from the definition that this ring is connected to the fluorene skeleton to which R 28 and R 29 are bonded by a spiro bond as shown in the following formula (E1). It should be noted that R 21 ~R 27 are omitted in the following formula.

[0574] [Chemical formula 24]

[0575]

[0576] Here, "there is no case where a 9,9-spirobifluorene ring is formed together with the fluorene ring to which R 28 and R 29 are bonded" means that R 28 and R 29 do not bond to each other to form a fluorene ring. That is, a compound in which a group represented by the following formula (E2) is bonded to a nitrogen atom via (L 21 ) n21 is not included in the compound represented by formula (1).

[0577] [Chemical formula 25]

[0578]

[0579] When the group represented by formula (E2) has a substituent (R 21 ~R 27 is the substituent R, and when R 28 and R 29 are bonded to each other to form a substituted fused ring), it is the same. The group represented by formula (E2) having a substituent is bonded to a nitrogen atom via (L 21 ) n21 , and the compound is not included in the compound represented by formula (1).

[0580] Regarding "wherein, when R 38 and R 39 are bonded to each other to form a substituted or unsubstituted fused ring, there is no case where a 9,9-spirobifluorene ring is formed together with the fluorene ring to which R 38 and R 39 are bonded", except that R 28 is replaced with R 38 , R 29 is replaced with R 39 , and (L 21 ) n21 is replaced with (L 31 ) n31 , the same explanation as above can be applied.

[0581] Regarding "when n11 is 2 or 3, a plurality of L 11 are connected in series with each other, and the tricyclic fused skeleton is bonded to the L 11 farthest from the benzene skeleton", "when n21 is 2 or 3, a plurality of L 21 are connected in series with each other, and the fluorene skeleton is bonded to the L 21 farthest from the nitrogen atom", and "when n31 is 2 or 3, a plurality of L 31 are connected in series with each other, and the fluorene skeleton is bonded to the L 31 farthest from the nitrogen atom" in formula (1), an explanation is given.

[0582] It is obvious from the definition that when n11 is 2 or 3, a plurality of L 11 are connected in series between the benzene skeleton and the tricyclic fused skeleton without branching. For L 21 and L 31 , similarly, they are connected in series between the nitrogen atom and the fluorene skeleton without branching.

[0583] For example, when n11 is 2, n12 is 3, and n13 is 2, the compound represented by formula (1) has the structure represented by the following formula (E3).

[0584] [Chemical formula 26]

[0585]

[0586] In one embodiment, R 28 and R 29 When they are bonded to each other to form a substituted or unsubstituted monocyclic or fused ring, the ring formed thereby, and R 38 and R 39 When they are bonded to each other to form a substituted or unsubstituted monocyclic or fused ring, the rings formed thereby are each independently selected from the rings represented by the following formulas (1a) to (1r).

[0587] [Chemical formula 27]

[0588]

[0589] In formulas (1a) to (1r),

[0590] C spiro represents the carbon atom of the fluorene ring to which R 28 and R 29 are bonded, or the carbon atom of the fluorene ring to which R 38 and R 39 are bonded.

[0591] The carbon atoms constituting the ring have a hydrogen atom or a substituent R at the position where bonding is possible.

[0592] The substituent R is defined as in the aforementioned formula (1).

[0593] Regarding "C spiro represents the carbon atom of the fluorene ring to which R 28 and R 29 are bonded, or the carbon atom of the fluorene ring to which R 38 and R 39 are bonded" in formulas (1a) to (1r), an explanation is given.

[0594] C spiro means a spiro carbon atom. That is, the rings represented by formulas (1a) to (1r) are bonded to the fluorene ring to form a spiro ring group.

[0595] For example, when R 28 and R 29 are bonded to each other to form the ring represented by formula (1a), the group bonded to the nitrogen atom via (L 21 )n21 is the spiro ring group (substituted or unsubstituted spiro[9H-fluorene-9,1'-cyclopentane]-2-yl) represented by the following formula (E4). It should be noted that R 21 to R 27 are omitted in the following formula.

[0596] [Chemical formula 28]

[0597]

[0598] It should be noted that, as is obvious from the definition, the rings represented by formulas (1a) to (1r) and the fluorene ring are bonded only through C spiro bonds and do not have crosslinking.

[0599] In one embodiment, R 28 and R 29 are bonded to each other to form a substituted or unsubstituted monocyclic or fused ring.

[0600] In one embodiment, R 28 and R 29 are not bonded to each other, R 28 is an alkyl group having 1 to 50 carbon atoms which may be substituted or unsubstituted, and R 29 is an alkyl group having 1 to 50 carbon atoms which may be substituted or unsubstituted or an aryl group having 6 to 50 ring-forming carbon atoms which may be substituted or unsubstituted.

[0601] In one embodiment, R 28 and R 29 are not bonded to each other, R 28 is an alkyl group having 1 to 5 carbon atoms which may be substituted or unsubstituted, and R 29 is an alkyl group having 1 to 5 carbon atoms which may be substituted or unsubstituted or an aryl group having 6 to 10 ring-forming carbon atoms which may be substituted or unsubstituted.

[0602] In one embodiment, R 38 and R 39 are bonded to each other to form a substituted or unsubstituted monocyclic or fused ring.

[0603] In one embodiment, R 38 and R 39 are not bonded to each other, R 38 is an alkyl group having 1 to 50 carbon atoms which may be substituted or unsubstituted, and R 39 is an alkyl group having 1 to 50 carbon atoms which may be substituted or unsubstituted or an aryl group having 6 to 50 ring-forming carbon atoms which may be substituted or unsubstituted.

[0604] In one embodiment, R 38 and R 39 are not bonded to each other, R 38 is an alkyl group having 1 to 5 carbon atoms which may be substituted or unsubstituted, and R 39 is an alkyl group having 1 to 5 carbon atoms which may be substituted or unsubstituted or an aryl group having 6 to 10 ring-forming carbon atoms which may be substituted or unsubstituted.

[0605] In one embodiment, R 28 and R 29 are not bonded to each other, R 28 is an alkyl group having 1 to 50 carbon atoms which may be substituted or unsubstituted, and R 29is an alkyl group having 1 to 50 carbon atoms which may be substituted or unsubstituted, or an aryl group having 6 to 50 ring-constituting carbon atoms which may be substituted or unsubstituted,

[0606] R 38 and R 39 do not bond to each other, R 38 is an alkyl group having 1 to 50 carbon atoms which may be substituted or unsubstituted, R 39 is an alkyl group having 1 to 50 carbon atoms which may be substituted or unsubstituted, or an aryl group having 6 to 50 ring-constituting carbon atoms which may be substituted or unsubstituted.

[0607] In one embodiment, R 28 and R 29 do not bond to each other, R 28 is an alkyl group having 1 to 5 carbon atoms which may be substituted or unsubstituted, R 29 is an alkyl group having 1 to 5 carbon atoms which may be substituted or unsubstituted, or an aryl group having 6 to 10 ring-constituting carbon atoms which may be substituted or unsubstituted,

[0608] R 38 and R 39 do not bond to each other, R 38 is an alkyl group having 1 to 5 carbon atoms which may be substituted or unsubstituted, R 39 is an alkyl group having 1 to 5 carbon atoms which may be substituted or unsubstituted, or an aryl group having 6 to 10 ring-constituting carbon atoms which may be substituted or unsubstituted.

[0609] In one embodiment, R 28 and R 29 do not bond to each other, R 28 is an alkyl group having 1 to 50 carbon atoms which may be substituted or unsubstituted, R 29 is an alkyl group having 1 to 50 carbon atoms which may be substituted or unsubstituted, or an aryl group having 6 to 50 ring-constituting carbon atoms which may be substituted or unsubstituted,

[0610] R 38 and R 39 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.

[0611] In one embodiment, R 28 and R 29 do not bond to each other, R 28 is an alkyl group having 1 to 5 carbon atoms which may be substituted or unsubstituted, R 29 is an alkyl group having 1 to 5 carbon atoms which may be substituted or unsubstituted, or an aryl group having 6 to 10 ring-constituting carbon atoms which may be substituted or unsubstituted,

[0612] R 38 and R 39 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.

[0613] In one embodiment, R 28 and R 29 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring,

[0614] R 38 and R 39 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring.

[0615] In one embodiment, R 21 ~R 27 and R 31 ~R 37 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0616] In one embodiment, R 21 ~R 27 is a hydrogen atom.

[0617] In one embodiment, R 31 ~R 37 is a hydrogen atom.

[0618] In one embodiment, R 21 ~R 27 and R 31 ~R 37 are hydrogen atoms.

[0619] In one embodiment, X 11 is an oxygen atom.

[0620] In one embodiment, R 11 ~R 17 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0621] In one embodiment, R 11 ~R 17 is a hydrogen atom.

[0622] In one embodiment, R1 to R4 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms.

[0623] In one embodiment, R1 to R4 are hydrogen atoms.

[0624] In one embodiment, L 11 , L 21 and L 31Each is independently a single bond or a substituted or unsubstituted phenylene group.

[0625] In one embodiment, L 11 is a single bond.

[0626] In one embodiment, L 21 is a single bond.

[0627] In one embodiment, L 31 is a single bond.

[0628] In one embodiment, L 11 , L 21 and L 31 are single bonds.

[0629] In one embodiment, the compound represented by the aforementioned formula (1) is the compound represented by the following formula (1-1).

[0630] [Chemical formula 29]

[0631]

[0632] In formula (1-1), X 11 , n11, n21, n31, L 11 , L 21 , L 31 , R 28 , R 29 , R 38 and R 39 are as defined in the aforementioned formula (1).

[0633] In one embodiment, the compound represented by the aforementioned formula (1) is the compound represented by the following formula (1-11).

[0634] [Chemical formula 30]

[0635]

[0636] In formula (1-11), X 11 , n11, n21, n31, L 11 , L 21 and L 31 are as defined in the aforementioned formula (1).

[0637] R 128 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0638] R 129 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0639] R 138is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0640] R 139 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

[0641] In one embodiment, the compound represented by the aforementioned formula (1) is the compound represented by the following formula (1-21).

[0642] [Chemical formula 31]

[0643]

[0644] In formula (1-21), X 11 , n11, n21, n31, L 11 , L 21 and L 31 are as defined in the aforementioned formula (1).

[0645] R 228 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0646] R 229 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

[0647] R 238 and R 239 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring. Among them, when R 238 and R 239 are bonded to each other to form a substituted or unsubstituted fused ring, there is no case where a 9,9-spirobifluorene ring is formed together with the fluorene ring to which R 238 and R 239 are bonded.

[0648] As described in [Definition], the "hydrogen atom" used in this specification includes protium atoms, deuterium atoms, and tritium atoms. Therefore, the inventive compounds may also contain deuterium atoms of natural origin.

[0649] In addition, by using a compound in which part or all of the starting compound is deuterated, deuterium atoms can be actively introduced into the inventive compounds.

[0650] In one embodiment, the compound represented by formula (1) contains at least 1 deuterium atom. That is, the compound of this embodiment may be the compound represented by formula (1) and at least one of the hydrogen atoms contained in the compound is a deuterium atom.

[0651] In the compound represented by formula (1), at least one hydrogen atom selected from the following may be a deuterium atom:

[0652] R 11 ~R 17 The hydrogen atoms of the ring formed when forming a ring;

[0653] R as a hydrogen atom 11 ~R 17 ;

[0654] R as a substituent R 11 ~R 17 The hydrogen atoms it has;

[0655] The hydrogen atoms of the ring formed when R1 to R4 form a ring;

[0656] R1 to R4 as hydrogen atoms;

[0657] The hydrogen atoms of R1 to R4 as an alkyl group;

[0658] The hydrogen atoms of R1 to R4 as a cycloalkyl group;

[0659] R 21 ~R 27 The hydrogen atoms of the ring formed when forming a ring;

[0660] R as a hydrogen atom 21 ~R 27 ;

[0661] R as a substituent R 21 ~R 27 The hydrogen atoms it has;

[0662] R 28 and R 29 The hydrogen atoms of the ring formed when forming a ring;

[0663] R as an alkyl group 28 and R 29 The hydrogen atoms it has;

[0664] R as an aryl group 28 and R 29 The hydrogen atoms it has;

[0665] R 31 ~R 37 The hydrogen atoms of the ring formed when forming a ring;

[0666] R as a hydrogen atom 31 ~R 37 ;

[0667] R as a substituent R 31 ~R 37Hydrogen atoms possessed;

[0668] R 38 and R 39 Hydrogen atoms possessed by the ring when forming a ring;

[0669] R as an alkyl group 38 and R 39 Hydrogen atoms possessed;

[0670] R as an aryl group 38 and R 39 Hydrogen atoms possessed;

[0671] L 11 Hydrogen atoms possessed;

[0672] L 21 Hydrogen atoms possessed; and

[0673] L 31 Hydrogen atoms possessed.

[0674] In the compound represented by formula (1), at least one hydrogen atom selected from the following may be a deuterium atom:

[0675] Hydrogen atoms possessed by the ring when R1 to R4 form a ring;

[0676] R1 to R4 as hydrogen atoms;

[0677] Hydrogen atoms possessed by R1 to R4 as alkyl groups; and

[0678] Hydrogen atoms possessed by R1 to R4 as cycloalkyl groups.

[0679] In the compound represented by formula (1), at least one hydrogen atom selected from R1 to R4 as hydrogen atoms may be a deuterium atom.

[0680] The deuteration rate of the compound depends on the deuteration rate of the starting compound used. Even when using a starting material with a specified deuteration rate, it is possible to contain protium isotopes in a constant ratio from natural sources. Therefore, the deuteration rate includes a ratio obtained by considering trace isotopes from natural sources with respect to the ratio calculated simply by counting the number of deuterium atoms shown in the chemical formula.

[0681] In one embodiment, the deuteration rate of the compound is, for example, 1% or more, 3% or more, 5% or more, 10% or more, or 50% or more.

[0682] The compound represented by formula (1) can be synthesized according to the examples by using known substitution reactions and starting materials corresponding to the target compound.

[0683] Hereinafter, although specific examples of the compound represented by formula (1) are described, they are merely illustrative, and the compound represented by formula (1) is not limited to the following specific examples.

[0684] [Chemical Formula 32]

[0685]

[0686] [Chemical Formula 33]

[0687]

[0688] [Chemical Formula 34]

[0689]

[0690] [Chemical Formula 35]

[0691]

[0692] [Chemical Formula 36]

[0693]

[0694] [Chemical Formula 37]

[0695]

[0696] [Chemical Formula 38]

[0697]

[0698] [Chemical Formula 39]

[0699]

[0700] [Chemical Formula 40]

[0701]

[0702] [Chemical Formula 41]

[0703]

[0704] [Materials for Organic Electroluminescent Devices]

[0705] The compound according to one embodiment of the present invention can be used as a material for an organic EL device. For example, it can be used as a material used in the hole transport region of an organic EL device.

[0706] [Organic EL Device]

[0707] An organic EL device according to one embodiment of the present invention will be described.

[0708] One aspect of the present invention relates to an organic EL element having a cathode, an anode, a light-emitting layer disposed between the cathode and the anode, and a first layer (also referred to as a "hole transport layer") disposed between the light-emitting layer and the anode, wherein the first layer contains a compound according to one aspect of the present invention (the compound represented by formula (1)).

[0709] In one embodiment, in the organic EL element according to one aspect of the present invention, the first layer has a first layer A and a first layer B from the anode side, and at least one of the first layer A and the first layer B contains a compound according to one aspect of the present invention (the compound represented by formula (1)).

[0710] In one embodiment, in the organic EL element according to one aspect of the present invention, the first layer has a first layer A and a first layer B from the anode side, and the first layer B contains a compound according to one aspect of the present invention (the compound represented by formula (1)).

[0711] In one embodiment, the ionization potential Ip of the first layer A A and the ionization potential Ip of the first layer B B satisfy the following formula (E1).

[0712] |Ip A - Ip B | < 0.20 [eV] ··· (E1)

[0713] When the above formula (E1) is satisfied, the hole injection property between the first layer A and the first layer B is easily improved. Thereby, it is expected that the driving voltage of the element becomes lower and the external quantum efficiency is improved.

[0714] In this specification, the ionization potential Ip of the first layer A A means the ionization potential of the material constituting the first layer A.

[0715] In this specification, the ionization potential Ip of the first layer B A means the ionization potential of the material constituting the first layer B.

[0716] The ionization potential Ip of the first layer A A and the ionization potential Ip of the first layer B B can be measured separately by the methods described in the examples.

[0717] In one embodiment, the ionization potential Ip of the first layer A A and the ionization potential Ip of the first layer B B satisfy any one of the following formulas.

[0718] |Ip A - Ip B|< 0.15 [eV] ··· (E1-1)

[0719] |Ip A -Ip B |< 0.10 [eV] ··· (E1-2)

[0720] Ip A -Ip B < 0.20 [eV] ··· (E1-3)

[0721] Ip A -Ip B < 0.15 [eV] ··· (E1-4)

[0722] Ip A -Ip B < 0.10 [eV] ··· (E1-5)

[0723] In one embodiment, the refractive index n of the first layer A A and the refractive index n of the first layer B B satisfy the following formula (E2).

[0724] |n A -n B | > 0.05 ··· (E2)

[0725] When the above formula (E2) is satisfied, the light extraction efficiency of the device is likely to be improved. Accordingly, an improvement in the external quantum efficiency of the device can be expected.

[0726] In this specification, the refractive index n of the first layer A A means the refractive index of the material constituting the first layer A.

[0727] In this specification, the refractive index n of the first layer B B means the refractive index of the material constituting the first layer B.

[0728] The refractive index n of the first layer A A and the refractive index n of the first layer B B can be measured separately by the methods described in the examples.

[0729] It should be noted that when a layer contains a plurality of compounds, the refractive index of the constituent material of the layer can be measured by the methods described in the examples using a film formed by co-evaporating a plurality of compounds as the material to be measured on a glass substrate, or a film formed by evaporating a mixture containing a plurality of compounds as the material to be measured.

[0730] In one embodiment, the refractive index n of the first layer A A and the refractive index n of the first layer B B satisfy any one of the following formulas.

[0731] |n A -n B |>0.075 ··· (E2-1)

[0732] |n A -n B |>0.08 ··· (E2-2)

[0733] |n A -n B |>0.10 ··· (E2-3)

[0734] n A -n B >0.05 ··· (E2-4)

[0735] n A -n B >0.075 ··· (E2-5)

[0736] n A -n B >0.08 ··· (E2-6)

[0737] n A -n B >0.10 ··· (E2-7)

[0738] In one embodiment, the ionization potential Ip of the first layer A A and the ionization potential Ip of the first layer B B satisfy the following formula (E1),

[0739] The refractive index n of the first layer A A and the refractive index n of the first layer B B satisfy the following formula (E2).

[0740] |Ip A -Ip B |<0.20 [eV] ··· (E1)

[0741] |n A -n B |>0.05 ··· (E2)

[0742] In one embodiment, an organic EL element according to one aspect of the present invention has a second layer (also referred to as an "electron blocking layer") between the aforementioned first layer and the aforementioned light-emitting layer. As the second layer at this time, for example, the configuration of the hole transport layer described later can be applied.

[0743] In one embodiment, an organic EL element according to one aspect of the present invention has a third layer (also referred to as a "hole injection layer") between the anode and the first layer. As the third layer at this time, for example, the configuration of the hole injection layer described later can be applied.

[0744] In one embodiment, the third layer contains a compound according to one aspect of the present invention (the compound represented by formula (1)).

[0745] The third layer may further contain a material other than the compound according to one aspect of the present invention (for example, a doped compound).

[0746] As a material other than the compound according to one aspect of the present invention, the materials of the hole injection layer described later can be cited.

[0747] [Doped compound]

[0748] By containing a doped compound in the third layer, it is expected that the hole injection property from the anode to the first layer will be improved.

[0749] In one embodiment, the doped compound is a compound containing at least one of the first ring structure represented by the following formula (P11) and the second ring structure represented by the following formula (P12).

[0750] [Chemical formula 42]

[0751]

[0752] The first ring structure represented by formula (P11) is condensed with at least one of an aromatic hydrocarbon ring having 6 to 50 ring-constituting carbon atoms which may be substituted or unsubstituted and a heterocyclic ring having 5 to 50 ring-constituting atoms which may be substituted or unsubstituted in the molecule of the doped compound.

[0753] =Z 10 The structure shown is represented by the following formula (11a), (11b), (11c), (11d), (11e), (11f), (11g), (11h), (11i), (11j), (11k) or (11m).

[0754] [Chemical formula 43]

[0755]

[0756] [Chemical formula 44]

[0757]

[0758] In formula (11a), (11b), (11c), (11d), (11e), (11f), (11g), (11h), (11i), (11j), (11k) or (11m), R11 ~R 14 and R 1101 ~R 1110 Each independently is:

[0759] Hydrogen atoms,

[0760] Halogen atoms,

[0761] Hydroxyl,

[0762] Cyano,

[0763] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0764] a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms,

[0765] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0766] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0767] -O-(R 904 ) shown in the group,

[0768] -S-(R 905 ) shown in the group,

[0769] -N(R 906 )(R 907 ) shown in the group,

[0770] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0771] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0772] In formula (P12), Z1 to Z5 are each independently:

[0773] Nitrogen atoms,

[0774] With R 15 bonded carbon atoms, or

[0775] A carbon atom bonded to other atoms in the molecule of the aforementioned dopant compound.

[0776] Here, at least one of Z1 to Z5 is a carbon atom bonded to other atoms in the molecule of the dopant compound.

[0777] R 15 Selected from:

[0778] Hydrogen atoms,

[0779] a halogen atom,

[0780] a cyano group,

[0781] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0782] a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms,

[0783] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0784] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0785] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0786] -Si(R 901 )(R 902 )(R 903 ) group,

[0787] -O-(R 904 ) group,

[0788] -S-(R 905 ) group,

[0789] -N(R 906 )(R 907 ) group,

[0790] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0791] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0792] a carboxyl group,

[0793] a substituted or unsubstituted ester group,

[0794] a substituted or unsubstituted carbamoyl group,

[0795] a nitro group, and

[0796] a substituted or unsubstituted siloxanyl group.

[0797] R 15 When there are a plurality of R 15 may be the same or different from each other.

[0798] In the doping compound, R 901 to R 907 are each independently:

[0799] a hydrogen atom,

[0800] An alkyl group having 1 to 50 carbon atoms, which may be substituted or unsubstituted,

[0801] A cycloalkyl group having 3 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted,

[0802] An aryl group having 6 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, or

[0803] A heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted.

[0804] R 901 When there are a plurality of them, the plurality of Rs 901 May be the same or different from each other.

[0805] R 902 When there are a plurality of them, the plurality of Rs 902 May be the same or different from each other.

[0806] R 903 When there are a plurality of them, the plurality of Rs 903 May be the same or different from each other.

[0807] R 904 When there are a plurality of them, the plurality of Rs 904 May be the same or different from each other.

[0808] R 905 When there are a plurality of them, the plurality of Rs 905 May be the same or different from each other.

[0809] R 906 When there are a plurality of them, the plurality of Rs 906 May be the same or different from each other.

[0810] R 907 When there are a plurality of them, the plurality of Rs 907 May be the same or different from each other.

[0811] In the doping compound, the ester group is at least one group selected from an alkyl ester group and an aryl ester group.

[0812] The alkyl ester group is represented by, for example, -C(=O)OR E as shown. R E is, for example, an alkyl group having 1 to 50 carbon atoms (preferably 1 to 10 carbon atoms), which may be substituted or unsubstituted.

[0813] The aryl ester group is represented by, for example, -C(=O)OR Ar as shown. R Ar is, for example, an aryl group having 6 to 30 ring-forming carbon atoms, which may be substituted or unsubstituted.

[0814] In the doping compound, the siloxanyl group is a silicon compound group via an ether bond, for example, a trimethylsiloxanyl group.

[0815] The carbamoyl group is represented by -CONH2.

[0816] The substituted carbamoyl group is represented by, for example, -CONH-Ar C or -CONH-R C . Ar C is, for example, at least any group selected from an aryl group having 6 to 50 (preferably 6 to 10) ring-constituting carbon atoms and a heterocyclic group having 5 to 50 (preferably 5 to 14) ring-constituting atoms, which may be substituted or unsubstituted. Ar C may be a group formed by bonding a substituted or unsubstituted aryl group having 6 to 50 ring-constituting carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 50 ring-constituting atoms.

[0817] R C is, for example, a substituted or unsubstituted alkyl group having 1 to 50 (preferably 1 to 6) carbon atoms.

[0818] In the doping compound, the groups described as "substituted or unsubstituted" are preferably "unsubstituted" groups.

[0819] (Specific examples of the doping compound)

[0820] As specific examples of the doping compound, the following compounds can be cited, for example. However, the doping compound is not limited to these specific examples.

[0821] [Chemical formula 45]

[0822]

[0823] In one embodiment, the third layer contains 70% by mass or more, 80% by mass or more, 90% by mass or more, 95% by mass or more, or 98% by mass or more of the compound according to one aspect of the present invention based on the total mass of the third layer.

[0824] In one embodiment, the organic EL element according to one aspect of the present invention has an electron transport region between the cathode and the light-emitting layer.

[0825] As a representative element structure of the organic EL element, a structure in which the following structures are laminated on a substrate can be exemplified.

[0826] (1) Anode / hole transport region / light-emitting layer / cathode

[0827] (2) Anode / hole transport region / light-emitting layer / electron transport region / cathode

[0828] ( " / " indicates that the layers are adjacent and laminated. )

[0829] The hole transport region generally includes a hole transport layer, and may also include one or more layers selected from a hole injection layer and an electron blocking layer. The electron transport region generally includes one or more layers selected from an electron injection layer and an electron transport layer.

[0830] The hole transport region may include two or more hole transport layers.

[0831] The electron transport region may include two or more electron transport layers.

[0832] Refer to Figure 1 The schematic configuration of an organic EL element showing one embodiment of the present invention is described.

[0833] An organic EL element 1 according to one embodiment of the present invention includes: a substrate 2, an anode 3, a light-emitting layer 5, a cathode 10, a hole transport region 4 located between the anode 3 and the light-emitting layer 5, and an electron transport region 6 located between the light-emitting layer 5 and the cathode 10.

[0834] Hereinafter, members that can be used in the organic EL element according to one embodiment of the present invention, materials other than the above compounds constituting each layer, and the like will be described.

[0835] (Substrate)

[0836] The substrate serves as a support for the light-emitting element. As the substrate, for example, glass, quartz, plastic, etc. can be used. In addition, a flexible substrate can also be used. A flexible substrate refers to a substrate that can be bent (flexible), and examples include plastic substrates formed of polycarbonate and polyvinyl chloride.

[0837] (Anode)

[0838] The anode formed on the substrate preferably uses a metal, alloy, conductive compound, and a mixture 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, tungsten oxide, indium containing zinc oxide, and graphene. In addition, gold (Au), platinum (Pt), or nitrides of metal materials (for example, titanium nitride) can also be cited.

[0839] (Hole injection layer)

[0840] The hole injection layer is a layer containing a substance with high hole injection properties. As a substance with high hole injection properties, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, aromatic amine compounds, or polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used.

[0841] In one embodiment of the present invention, the hole injection layer may contain or not contain the above-mentioned other substances in addition to the compound (the compound represented by formula (1)) according to one embodiment of the present invention.

[0842] (Hole transport layer)

[0843] The hole transport layer is a layer containing a substance with high hole transportability. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used in the hole transport layer. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. Among them, as long as the substance has higher hole transportability than electron transportability, substances other than the above can be used. It should be noted that the layer containing a substance with high hole transportability can be not only a single-layer but also a layer formed by laminating two or more layers containing the above substances.

[0844] In one embodiment of the present invention, the hole transport layer may contain or not contain the above-mentioned other substances in addition to the compound (the compound represented by formula (1)) according to one embodiment of the present invention.

[0845] (Guest (dopant) material of the light-emitting layer)

[0846] The light-emitting layer is a layer containing a substance with high luminescence, and various materials can be used. For example, as the substance with high luminescence, a fluorescent compound that emits fluorescence and a phosphorescent compound that emits phosphorescence can be used. A fluorescent compound is a compound that can emit light from a singlet excited state, and a phosphorescent compound is a compound that can emit light from a triplet excited state.

[0847] As a blue fluorescent light-emitting material that can be used in the light-emitting layer, pyrene derivatives, styrylamine derivatives, derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, azaborinine derivatives, arylborane derivatives, triarylamine derivatives, etc. can be used. As a green fluorescent light-emitting material that can be used in the light-emitting layer, azaborinine derivatives, arylborane derivatives, aromatic amine derivatives, etc. can be used. As a red fluorescent light-emitting material that can be used in the light-emitting layer, bisanthracene derivatives, diamine derivatives, etc. can be used.

[0848] As a blue phosphorescent light-emitting material that can be used in the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used. As a green phosphorescent light-emitting material that can be used in the light-emitting layer, iridium complexes, etc. are used. As a red phosphorescent light-emitting 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.

[0849] In one embodiment, the light-emitting layer contains an azaborinine derivative.

[0850] In one embodiment, the light-emitting layer contains a compound represented by the following formula (D1).

[0851] [Chemical formula 46]

[0852]

[0853] In formula (D1),

[0854] ring a, ring b, and ring c are each independently:

[0855] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-constituting carbon atoms, or

[0856] a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-constituting atoms.

[0857] R D601 and R D602 each independently bond to the aforementioned ring a, ring b, or ring c to form a substituted or unsubstituted heterocyclic ring, or do not form a substituted or unsubstituted heterocyclic ring.

[0858] R D601 and R D602 that do not form the aforementioned substituted or unsubstituted heterocyclic ring are each independently:

[0859] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0860] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0861] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0862] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-constituting carbon atoms,

[0863] a substituted or unsubstituted aryl group having 6 to 50 ring-constituting carbon atoms, or

[0864] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-constituting atoms.

[0865] Ring a, ring b, and ring c are rings (substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring-constituting carbon atoms, or substituted or unsubstituted heterocyclic rings having 5 to 50 ring-constituting atoms) fused to the central fused bicyclic structure of formula (D1) composed of a boron atom and two nitrogen atoms.

[0866] The compound formed by introducing a hydrogen atom into the "aromatic hydrocarbon ring" and "aryl group" of ring a, ring b, and ring c has the same structure.

[0867] The "aromatic hydrocarbon ring" of ring a includes 3 carbon atoms on the fused bicyclic structure in the center of formula (D1) as ring-forming atoms.

[0868] The "aromatic hydrocarbon ring" of ring b and ring c includes 2 carbon atoms on the fused bicyclic structure in the center of formula (D1) as ring-forming atoms.

[0869] As a specific example of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms", compounds formed by introducing a hydrogen atom into the "aryl group" described in specific example group G1 can be cited, etc.

[0870] The "heterocyclic ring" of ring a, ring b and ring c has the same structure as the compound formed by introducing a hydrogen atom into the above-mentioned "heterocyclic group".

[0871] The "heterocyclic ring" of ring a includes 3 carbon atoms on the fused bicyclic structure in the center of formula (D1) as ring-forming atoms. The "heterocyclic ring" of ring b and ring c includes 2 carbon atoms on the fused bicyclic structure in the center of formula (D1) as ring-forming atoms. As a specific example of the "substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms", compounds formed by introducing a hydrogen atom into the "heterocyclic group" described in specific example group G2 can be cited, etc.

[0872] R D601 and R D602 can each independently bond to ring a, ring b or ring c to form a substituted or unsubstituted heterocyclic ring. The heterocyclic ring in this case includes a nitrogen atom on the fused bicyclic structure in the center of formula (D1). The heterocyclic ring in this case may further include heteroatoms other than the nitrogen atom. R D601 and R D602 bonding to ring a, ring b or ring c specifically means that the atoms constituting ring a, ring b or ring c bond to the atoms constituting R D601 and R D602 . For example, R D601 can bond to ring a to form a nitrogen-containing heterocyclic ring in which a ring containing R D601 is fused with ring a (or a tricyclic fusion or higher). As a specific example of this nitrogen-containing heterocyclic ring, compounds corresponding to the heterocyclic groups having a bicyclic fusion or higher containing nitrogen in specific example group G2 can be cited, etc.

[0873] R D601 bonding to ring b, the case of R D602 bonding to ring a, and the case of R D602 bonding to ring c are also the same as above.

[0874] R D601 and R D602 can each independently not bond to ring a, ring b or ring c.

[0875] In one embodiment, each of the a-ring, b-ring, and c-ring in formula (D1) is independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms.

[0876] In one embodiment, each of the a-ring, b-ring, and c-ring in formula (D1) is independently a substituted or unsubstituted benzene ring or naphthalene ring.

[0877] In one embodiment, R in formula (D1) D601 and R D602 are each independently:

[0878] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or

[0879] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,

[0880] preferably a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

[0881] In one embodiment, the compound represented by formula (D1) is a compound represented by the following formula (D1-1) or formula (D1-2).

[0882] [Chemical formula 47]

[0883]

[0884] In formula (D1-1),

[0885] R D601A bonds with one or more selected from R D611 and R D622 to form a substituted or unsubstituted heterocyclic ring, or does not form the aforementioned heterocyclic ring.

[0886] R D602A bonds with one or more selected from R D613 and R D614 to form a substituted or unsubstituted heterocyclic ring, or does not form the aforementioned heterocyclic ring.

[0887] When R D601A and R D602A do not form the aforementioned heterocyclic ring, they are each independently:

[0888] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0889] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0890] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0891] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[0892] Aryl having 6 to 50 ring-forming carbon atoms, which may or may not be substituted, or

[0893] Heterocyclic group having 5 to 50 ring-forming atoms, which may or may not be substituted.

[0894] One or more groups each composed of two or more adjacent ones among R D611 ~R D622 are bonded to each other to form an unsubstituted or substituted monocyclic ring, or are bonded to each other to form an unsubstituted or substituted fused ring, or are not bonded to each other.

[0895] R D611 、R D613 、R D614 and R D622 、and R D612 and R D615 ~R D621 are each independently a hydrogen atom or a substituent R.

[0896] In formula (D1-2),

[0897] X D601 is an oxygen atom or a sulfur atom.

[0898] R D602A bonds to one or more selected from R D613 and R D614 to form an unsubstituted or substituted heterocyclic ring, or does not form the aforementioned heterocyclic ring.

[0899] R D603A bonds to one or more selected from R D611 and R D634 to form an unsubstituted or substituted heterocyclic ring, or does not form the aforementioned heterocyclic ring.

[0900] R D602A and R D603A that do not form the aforementioned heterocyclic ring are each independently:

[0901] An alkyl group having 1 to 50 carbon atoms, which may or may not be substituted,

[0902] An alkenyl group having 2 to 50 carbon atoms, which may or may not be substituted,

[0903] An alkynyl group having 2 to 50 carbon atoms, which may or may not be substituted,

[0904] A cycloalkyl group having 3 to 50 ring-forming carbon atoms, which may or may not be substituted,

[0905] An aryl group having 6 to 50 ring-forming carbon atoms, which may or may not be substituted, or

[0906] A heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted.

[0907] Composed of R D611 ~R D617 and R D631 ~R D634 One or more groups, each composed of two or more adjacent ones among them, are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.

[0908] R D611 , R D613 , R D614 and R D634 , and R D612 , R D615 ~R D617 and R D631 ~R D633 are each independently a hydrogen atom or a substituent R.

[0909] The substituent R is selected from:

[0910] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0911] A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0912] A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0913] A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[0914] -Si(R 901 )(R 902 )(R 903 ),

[0915] -O-(R 904 ),

[0916] -S-(R 905 ),

[0917] -N(R 906 )(R 907 ),

[0918] A halogen atom, a cyano group, a nitro group,

[0919] A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and

[0920] A monovalent heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted.

[0921] When there are two or more substituents R, the two or more substituents R may be the same or different from each other.

[0922] R 901 ~R 907 Each independently is:

[0923] a hydrogen atom,

[0924] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0925] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0926] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0927] a monovalent heterocyclic group having 5 to 50 ring atoms which may be substituted or unsubstituted.

[0928] R 901 ~R 907 When there are two or more of each, the two or more Rs 901 ~R 907 each may be the same or different.

[0929] In one embodiment, the compound represented by formula (D1) is a compound represented by the following formula (D1-1-1) or formula (D1-2-1).

[0930] [Chemical formula 48]

[0931]

[0932] In formula (D1-1-1) and formula (D1-2-1),

[0933] R D601B and R D602B each independently is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0934] R D612A , R D616A , R D619A and R D633A each independently is:

[0935] a hydrogen atom,

[0936] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[0937] -N(R 906 )(R 907 ).

[0938] R 906 and R 907 each independently is:

[0939] a hydrogen atom,

[0940] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0941] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0942] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0943] a monovalent heterocyclic group having 5 to 50 ring atoms which may be substituted or unsubstituted.

[0944] R 906 and R 907 When there are two or more of each, two or more R's 906 and R 907 each may be the same or different.

[0945] As specific examples of the compound represented by formula (D1), the following compounds can be cited, for example. However, the compound represented by formula (D1) is not limited to these specific examples.

[0946] [Chemical formula 49]

[0947]

[0948] (Host material of the light-emitting layer)

[0949] As the light-emitting layer, a structure can be adopted in which the above-mentioned highly luminescent substance (guest material) is dispersed in another substance (host material). As the substance for dispersing the highly luminescent substance, various substances can be used, and a substance having a higher lowest unoccupied molecular orbital energy level (LUMO energy level) and a lower highest occupied molecular orbital energy level (HOMO energy level) than the highly luminescent substance is preferably used.

[0950] As the substance (host material) for dispersing the highly luminescent substance, 1) metal complexes such as aluminum complexes, beryllium complexes or zinc complexes, 2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives or phenanthroline derivatives, 3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives or derivatives, 4) aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives are used.

[0951] In one embodiment, the light-emitting layer contains an anthracene derivative having a heterocyclic group.

[0952] As specific examples of the heterocyclic group, the above-mentioned specific example group G2 can be cited.

[0953] In one embodiment, the light-emitting layer contains a compound represented by the following formula (H1).

[0954] [Chemical 50]

[0955]

[0956] In formula (H1),

[0957] X H11 is an oxygen atom, a sulfur atom or NR H100 .

[0958] L H1 and L H2 each independently is:

[0959] a single bond,

[0960] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[0961] a divalent heterocyclic group having 5 to 30 ring atoms which is substituted or unsubstituted.

[0962] Ar H1 is:

[0963] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[0964] a monovalent heterocyclic group having 5 to 30 ring atoms which is substituted or unsubstituted.

[0965] R H11 ~R H18 and R H100 any one of them represents a bond with L H2 (* indicates the bonding position of any one of R H11 ~R H18 and R H100的 with L H2 ).

[0966] One or more groups composed of two or more adjacent ones among R H2 that do not represent a bond with L H11 ~R H18 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.

[0967] R H1 ~R H8 , and R H2 that do not represent a bond with L H11 ~R H18 and R H100 each independently is a hydrogen atom or a substituent A.

[0968] The substituent A is:

[0969] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[0970] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

[0971] In one embodiment, R that does not represent a bond to L H2 through R H11 to R H18 and R H100 are each a hydrogen atom.

[0972] In one embodiment, only any one of R that does not represent a bond to L H2 through R H11 to R H18 and R H100 is a substituent A.

[0973] In one embodiment, Ar H1 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

[0974] In one embodiment, Ar H1 is selected from the groups represented by the following formulas (Ha1) to (Ha4).

[0975] [Chemical formula 51]

[0976]

[0977] In formulas (Ha1) to (Ha4), * represents the bonding position to L H1 .

[0978] bH1 is an integer of 0 to 4.

[0979] bH2 is an integer of 0 to 5.

[0980] bH3 is an integer of 0 to 7.

[0981] When each of bH1 to bH3 is 2 or more, the plurality of Rs H110 may be the same or different from each other.

[0982] When each of bH1 to bH3 is 2 or more, one or more groups each composed of two or more adjacent ones of the plurality of Rs H110 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.

[0983] The Rs H110 that do not bond to each other are each independently:

[0984] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0985] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0986] An alkynyl group having 2 to 50 carbon atoms, which may be substituted or unsubstituted,

[0987] A cycloalkyl group having 3 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted,

[0988] -Si(R 901 )(R 902 )(R 903 ),

[0989] -O-(R 904 ),

[0990] -S-(R 905 ),

[0991] -N(R 906 )(R 907 ),

[0992] A halogen atom, a cyano group, a nitro group,

[0993] An aryl group having 6 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, or

[0994] A monovalent heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted.

[0995] R 901 to R 907 are as defined in the aforementioned formula (1).

[0996] In one embodiment, L H1 and L H2 are each independently a single bond, or a substituted or unsubstituted arylene group having 6 to 14 ring-forming carbon atoms.

[0997] In one embodiment, at least one of L H1 and L H2 is a single bond.

[0998] In one embodiment, the compound represented by formula (H1) is a compound represented by the following formula (H1-1) or formula (H1-2).

[0999] [Chemical formula 52]

[1000]

[1001] L H1 、L H2 、Ar H1 and R H1 to R H8 are as defined in formula (H1).

[1002] X H21 is an oxygen atom, a sulfur atom or NRH100 .

[1003] R H21 ~R H30 and R H100 Any one of the expressions is consistent with L H2 Key (* indicates R H21 ~R H30 and R H100 Any one of them and L H2 bonding position).

[1004] By not indicating and L H2 The key of R H21 ~R H30 In the above, one or more adjacent groups of two or more are not bonded to each other, and do not form a substituted or unsubstituted monocyclic ring or condensed ring.

[1005] Not indicated with L H2 The key of R H21 ~R H30 and R H100 Each is independently a hydrogen atom or a substituent A.

[1006] In formula (H1-2),

[1007] L H1 , L H2 ,Ar H1 and R H1 ~R H8 As defined in formula (H1).

[1008] X H21 is an oxygen atom, a sulfur atom or NR H100 .

[1009] R H31 ~R H40 and R H100 Any one of the expressions is consistent with L H2 Key (* indicates R H31 ~R H40 and R H100 Any one of them and L H2 bonding position).

[1010] By not indicating and L H2 The key of R H31 ~R H40 In the above, one or more adjacent groups of two or more are not bonded to each other, and do not form a substituted or unsubstituted monocyclic ring or condensed ring.

[1011] Not indicated with L H2 The key of R H31 ~R H40 and R H100Each is independently a hydrogen atom or substituent A.

[1012] Substituent A is defined as in formula (H1).

[1013] In one embodiment, the compound represented by formula (H1) is a compound represented by the following formula (H1-1-1) or formula (H1-2-1).

[1014] [Chemical formula 53]

[1015]

[1016] In formula (H1-1-1) and formula (H1-2-1),

[1017] L H1 、L H2 、Ar H1 and R H1 ~R H8 are defined as in formula (H1).

[1018] In the structure within parentheses, one of the carbon atoms constituting the naphthofuran skeleton is bonded to L H2 by a single bond. When L H2 is a single bond, one of the carbon atoms constituting the naphthofuran skeleton is bonded to the anthracene skeleton by a single bond.

[1019] In one embodiment, the compound represented by formula (H1) is a compound represented by the following formula (H1-1-2) or formula (H1-2-2).

[1020] [Chemical formula 54]

[1021]

[1022] In formula (H1-1-2) and formula (H1-2-2),

[1023] L H1 、L H2 and Ar H1 are defined as in formula (H1).

[1024] In the structure within parentheses, one of the carbon atoms constituting the naphthofuran skeleton is bonded to L H2 by a single bond. When L H2 is a single bond, one of the carbon atoms constituting the naphthofuran skeleton is bonded to the anthracene skeleton by a single bond.

[1025] As specific examples of the compound represented by formula (H1), for example, the following compounds can be cited. However, the compound represented by formula (H1) is not limited to this specific example.

[1026] [Chemical formula 55]

[1027]

[1028] (Electron transport layer)

[1029] The electron transport layer is a layer containing a substance with high electron transportability. In the electron transport layer, the following can be used: 1) metal complexes such as aluminum complexes, beryllium complexes, zinc complexes, etc.; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, oxazine derivatives, carbazole derivatives, phenanthroline derivatives, etc.; 3) polymer compounds.

[1030] (Electron injection layer)

[1031] The electron injection layer is a layer containing a substance with high electron injectability. In the electron injection layer, metal complex compounds such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium 8-hydroxyquinoline (Liq), etc., and alkali metals, alkaline earth metals, or their compounds such as lithium oxide (LiO x ) can be used.

[1032] (Cathode)

[1033] Preferably, the cathode uses a metal, alloy, conductive compound, or a mixture 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.

[1034] The cathode is usually formed by a vacuum evaporation method or a sputtering method. In addition, when using silver paste or the like, a coating method, an inkjet method, etc. can be used.

[1035] In addition, when an electron injection layer is provided, regardless of the size of the work function, various conductive materials such as aluminum, silver, ITO, graphene, indium tin oxide containing silicon or silicon oxide can be used to form the cathode.

[1036] In the organic EL element according to one embodiment of the present invention, the film thickness of each layer is not particularly limited. Generally, in order to suppress defects such as pinholes, suppress the applied voltage to a low level, and achieve good luminous efficiency, it is usually preferably in the range of several nm to 1 μm.

[1037] In the organic EL element according to one embodiment of the present invention, the method for forming each layer is not particularly limited. Known formation methods based on vacuum evaporation, spin coating, etc. can be used. Each layer such as the light-emitting layer can be formed by a known method such as vacuum evaporation, molecular beam epitaxy (MBE method), or coating methods such as dip coating, spin coating, casting, bar coating, and roll coating of a solution dissolved in a solvent.

[1038] [Electronic device]

[1039] The electronic device according to one embodiment of the present invention is characterized by including the organic EL element according to one embodiment of the present invention.

[1040] As specific examples of the electronic device, display components such as organic EL panel assemblies; display devices such as televisions, mobile phones, or personal computers; and light-emitting devices such as lighting or vehicle lamps can be cited.

[1041] Examples

[1042] <Compound>

[1043] The compound represented by formula (1) used in the production of the organic EL element of the example is as follows.

[1044] [Chemical formula 56]

[1045]

[1046] The compounds used in the production of the organic EL element of the comparative example are as follows.

[1047] [Chemical formula 57]

[1048]

[1049] The structures of other compounds used in the production of the organic EL elements of the examples and comparative examples are as follows.

[1050] [Chemical formula 58]

[1051]

[1052] [Chemical formula 59]

[1053]

[1054] [Chemical formula 60]

[1055]

[1056] [Chemical formula 61]

[1057]

[1058] Example 1

[1059] <Fabrication of Organic EL Element>

[1060] An organic EL element was fabricated as follows.

[1061] A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 1.1 mm, a length of 25 mm, and a width of 75 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then subjected to UV-ozone cleaning for 30 minutes. The film thickness of the ITO was 130 nm.

[1062] The cleaned glass substrate with the transparent electrode was mounted on a substrate holder of a vacuum evaporation apparatus. First, on the surface where the transparent electrode was formed, Compound 1 and HI-1 were co-evaporated in such a manner that the proportion of Compound HI-1 reached 1% by mass to form a first hole transport layer (hole injection layer) with a film thickness of 10 nm so as to cover the transparent electrode.

[1063] Compound 1 was evaporated on the first hole transport layer to form a second hole transport layer (hole transport layer) with a film thickness of 77.5 nm.

[1064] Compound HT-1 was evaporated on the second hole transport layer to form a third hole transport layer (electron blocking layer) with a film thickness of 7.5 nm.

[1065] On the third hole transport layer, Compound BH-1 (host material), Compound BH-2 (host material), and Compound BD-1 (dopant material) were co-evaporated in a ratio (parts by mass) of 60:40:2 to form a light-emitting layer with a film thickness of 20 nm.

[1066] Compound ET-1 was evaporated on the light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

[1067] On the first electron transport layer, Compound ET-2 and Liq were co-evaporated in such a manner that the proportion of Liq reached 33% by mass to form a second electron transport layer with a film thickness of 25 nm.

[1068] Metal Yb was evaporated on the second electron transport layer to form an electron injection layer with a film thickness of 1 nm.

[1069] Metal Al was evaporated on the electron injection layer to form a cathode with a film thickness of 80 nm.

[1070] The element configuration of the organic EL element of Example 1 is briefly shown below.

[1071] ITO(130) / Compound 1:HI-1(10:1%) / Compound 1(77.5) / HT-1(7.5) / BH-1:BH-2:BD-1 = 60:40:2(20) / ET-1(5) / ET-2:Liq(25:33%) / Yb(1) / Al(80)

[1072] The numbers in parentheses represent the film thickness (unit: nm). In addition, within the parentheses, the numbers expressed as percentages represent the proportion (mass %) of the latter compound in that layer. BH-1:BH-2:BD-1 = 60:40:2 indicates that the proportions (parts by mass) of BH-1, BH-2, and BD-1 in that layer are 60:40:2, respectively.

[1073] <Evaluation of Organic EL Element>

[1074] The fabricated organic EL element was evaluated as follows. The results are shown in Table 1.

[1075] · Driving voltage

[1076] At room temperature, the initial characteristics of the organic EL element were measured by driving with a DC (direct current) constant current of 10 mA / cm 2

[1077] · External quantum efficiency

[1078] The organic EL element was applied with a voltage such that the current density reached 10 mA / cm 2 , and the EL emission spectrum was measured using a spectro-radiance meter CS-2000 (manufactured by Konica Minolta Inc.). The external quantum efficiency EQE (%) was calculated from the obtained spectro-radiance spectrum.

[1079] Example 2

[1080] In the formation of the first hole transport layer and the second hole transport layer, the compounds shown in Table 1 were used instead of Compound 1. Otherwise, an organic EL element was fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 1.

[1081] Comparative Examples 1 - 2

[1082] In the formation of the first hole transport layer and the second hole transport layer, the compounds shown in Table 1 were used instead of Compound 1. Otherwise, an organic EL element was fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 1.

[1083] [Table 1]

[1084] First hole transport layer Second hole transport layer Voltage (V) EQE (%) Example 1 Compound 1: HI-1 Compound 1 4.29 10.7 Example 2 Compound 4: HI-1 Compound 4 4.30 10.8 Comparative Example 1 HT-Ref1: HI-1 HT-Ref1 5.26 9.57 Comparative Example 2 HT-Ref2: HI-1 HT-Ref2 4.48 9.81

[1085] Example 3 ​

[1086] <Fabrication of Organic EL Element>

[1087] The organic EL element is fabricated as described below.

[1088] A glass substrate (manufactured by Jomatec Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 1.1 mm, a length of 25 mm, and a width of 75 mm is ultrasonically cleaned in isopropyl alcohol for 5 minutes and then subjected to UV ozone cleaning for 30 minutes. The film thickness of the ITO is 130 nm.

[1089] The cleaned glass substrate with the transparent electrode is mounted on the substrate holder of a vacuum evaporation apparatus. First, on the surface where the transparent electrode is formed, Compound 1 and HI-1 are co-evaporated in such a way that the proportion of Compound HI-1 reaches 2% by mass to form a first hole transport layer (hole injection layer) with a film thickness of 10 nm so as to cover the transparent electrode.

[1090] Compound 1 is evaporated on the first hole transport layer to form a second hole transport layer (hole transport layer) with a film thickness of 77.5 nm.

[1091] Compound HT-1 is evaporated on the second hole transport layer to form a third hole transport layer (electron blocking layer) with a film thickness of 7.5 nm.

[1092] On the third hole transport layer, Compound BH-1 (host material), Compound BH-2 (host material), and Compound BD-1 (dopant material) are co-evaporated in a ratio (parts by mass) of 60:40:2 to form a light-emitting layer with a film thickness of 20 nm.

[1093] Compound ET-1 is evaporated on the light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

[1094] On the first electron transport layer, Compound ET-2 and Liq are co-evaporated in such a way that the proportion of Liq reaches 33% by mass to form a second electron transport layer with a film thickness of 25 nm.

[1095] Metal Yb is evaporated on the second electron transport layer to form an electron injection layer with a film thickness of 1 nm.

[1096] Metal Al is evaporated on the electron injection layer to form a cathode with a film thickness of 80 nm.

[1097] The element configuration of the organic EL element of Example 3 is briefly shown below.

[1098] ITO(130) / Compound 1: HI-1(10:2%) / Compound 1(77.5) / HT-1(7.5) / BH-1:BH-2:BD-1 = 60:40:2(20) / ET-1(5) / ET-2:Liq(25:33%) / Yb(1) / Al(80)

[1099] The numbers in parentheses represent the film thickness (unit: nm). Additionally, within the parentheses, the numbers expressed as percentages represent the proportion (mass %) of the latter compound in that layer. BH-1:BH-2:BD-1 = 60:40:2 indicates that the proportions (parts by mass) of BH-1, BH-2, and BD-1 in that layer are 60:40:2, respectively.

[1100] <Evaluation of Organic EL Element>

[1101] The fabricated organic EL element was evaluated in the same manner as in Example 1. The results are shown in Table 2.

[1102] Example 4

[1103] In the formation of the first hole transport layer and the second hole transport layer, the compounds shown in Table 2 were used in place of Compound 1. Otherwise, an organic EL element was fabricated and evaluated in the same manner as in Example 3. The results are shown in Table 2.

[1104] Comparative Examples 3 - 4

[1105] In the formation of the first hole transport layer and the second hole transport layer, the compounds shown in Table 2 were used in place of Compound 1. Otherwise, an organic EL element was fabricated and evaluated in the same manner as in Example 3. The results are shown in Table 2.

[1106] [Table 2]

[1107] First hole transport layer Second hole transport layer Voltage (V) EQE (%) Example 3 Compound 1: HI-1 Compound 1 4.00 10.8 Example 4 Compound 2: HI-1 Compound 2 3.85 11.1 Comparative Example 3 HT-Ref3: HI-1 HT-Ref3 5.00 10.0 Comparative Example 4 HT-Ref4: HI-1 HT-Ref4 4.81 10.5

[1108] Example 5

[1109] <Fabrication of Organic EL Element>

[1110] An organic EL element was fabricated as described below.

[1111] A glass substrate (manufactured by Jomatec Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 1.1 mm, a length of 25 mm, and a width of 75 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 made 130 nm.

[1112] The cleaned glass substrate with a transparent electrode is mounted on the substrate holder of a vacuum evaporation apparatus. First, on the surface where the transparent electrode is formed, the compound 1 and HI-1 are co-evaporated in such a way that the proportion of the compound HI-1 reaches 2% by mass to cover the transparent electrode, forming a first hole transport layer (hole injection layer) with a film thickness of 10 nm.

[1113] Compound 1 is evaporated on the first hole transport layer to form a second hole transport layer (hole transport layer) with a film thickness of 80 nm.

[1114] Compound HT-2 is evaporated on the second hole transport layer to form a third hole transport layer (electron blocking layer) with a film thickness of 7.5 nm.

[1115] On the third hole transport layer, the compound BH-1 (host material) and the compound BD-2 (dopant material) are co-evaporated in such a way that the proportion of the compound BD-2 reaches 1% by mass, forming a light-emitting layer with a film thickness of 20 nm nm.

[1116] Compound ET-3 is evaporated on the light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

[1117] On the first electron transport layer, the compound ET-4 and Liq are co-evaporated in such a way that the proportion of Liq reaches 50% by mass, forming a second electron transport layer with a film thickness of 30 nm.

[1118] Metal Yb is evaporated on the second electron transport layer to form an electron injection layer with a film thickness of 1 nm.

[1119] Metal Al is evaporated on the electron injection layer to form a cathode with a film thickness of 50 nm.

[1120] The element structure of the organic EL element of Example 5 is briefly shown as follows.

[1121] ITO(130) / Compound 1:HI-1(10:2%) / Compound 1(80) / HT-2(7.5) / BH-1:BD-2(20:1%) / ET-3(5) / ET-4:Liq(30:50%) / Yb(1) / Al(50)

[1122] The numbers in parentheses represent the film thickness (unit: nm). In addition, in the parentheses, the numbers expressed as percentages represent the proportion of the latter compound in the layer (mass%).

[1123] The fabricated organic EL element is evaluated as follows. The results are shown in Table 3.

[1124] · Refractive index

[1125] The refractive index (n2) of the material (compound) constituting the second hole transport layer was measured as described below.

[1126] The material to be measured was vacuum-evaporated on a glass substrate to a film thickness of about 50 nm. Using a spectroscopic ellipsometer device (“M-2000UI”, manufactured by J.A. Woollam Co., Ltd.), incident light (ultraviolet to visible light to near-infrared) was irradiated at intervals of 5° in the range of measurement angles from 45° to 75°, and the change in the deflection state of the light reflected from the sample surface was measured. In order to improve the measurement accuracy of the extinction coefficient, the transmission spectrum in the substrate normal direction (the direction perpendicular to the plane of the organic EL element substrate) was also measured using this device. Similarly, the same measurement was performed only on the glass substrate without evaporating the material to be measured. The obtained measurement information was fitted using the analysis software (Complete EASE) manufactured by J.A. Woollam Co., Ltd.

[1127] As the fitting condition, a uniaxial rotationally symmetric anisotropic model was used, and in this software, the refractive index in the in-plane direction and the normal direction of the organic film formed on the substrate, the extinction coefficient in the in-plane direction and the normal direction, and the order parameter were calculated in such a way that the parameter MSE representing the mean square error was 3.0 or less. The peak on the long wavelength side of the extinction coefficient (in-plane direction) was designated as S1, and the order parameter was calculated from the peak wavelength of S1. As the fitting condition for the glass substrate, an isotropic model was used.

[1128] The film of the low-molecular material vacuum-evaporated on the substrate usually has a uniaxial rotational symmetry with the substrate normal direction as the axis of rotation. When the angle formed by the molecular axis in the thin film formed on the substrate and the substrate normal direction is θ, and the extinction coefficients in the substrate parallel direction (Ordinary direction) and the perpendicular direction (Extra-Ordinary direction) measured by the spectroscopic ellipsometer with multiple incident angles of the thin film are ko and ke, respectively, S’ shown in the following formula is the order parameter.

[1129] S’ = 1 - <cos2θ> = 2ko / (ke + 2ko) = 2 / 3(1 - S)

[1130] S = (1 / 2)<3cos2θ - 1> = (ke - ko) / (ke + 2ko)

[1131] This method for evaluating the molecular orientation is a well-known method, and the detailed content is described in the journal Organic Electronics, 2009, Vol. 10, page 127. In addition, the method for forming the thin film was the vacuum evaporation method.

[1132] The order parameter S' measured by a multi-angle-of-incidence spectroscopic ellipsometer is 1.0 when all molecules are oriented in a direction parallel to the substrate. Additionally, it is 0.66 when the molecules are not oriented and are random.

[1133] In this specification, the refractive index value at 2.7 eV in the substrate parallel direction (Ordinary direction) of the value measured as described above is set as the refractive index of the material to be measured. The refractive index at 2.7 eV corresponds to the refractive index at 460 nm.

[1134] · Element lifetime

[1135] At room temperature, a voltage is applied to the organic EL element such that the current density reaches 50 mA / cm 2 and the time (LT95 (unit: h)) until the luminance reaches 95% of the initial luminance is measured. In Table 3, the element lifetime represents the relative value when Comparative Example 5 is set to 100.

[1136] Examples 6, 8

[1137] In the formation of the light-emitting layer, the compound shown in Table 3 is used instead of compound BH-1, and except for this, an organic EL element is fabricated and evaluated in the same manner as in Example 5. The results are shown in Table 3.

[1138] Example 7

[1139] In the formation of the light-emitting layer, compound BH-1 and compound BH-3 (host material) are used in a ratio (parts by mass) of 50:50 instead of compound BH-1, and except for this, an organic EL element is fabricated and evaluated in the same manner as in Example 5. The results are shown in Table 3.

[1140] Comparative Example 5

[1141] In the formation of the first hole transport layer and the second hole transport layer, the compound shown in Table 3 is used instead of compound 1, and except for this, an organic EL element is fabricated and evaluated in the same manner as in Example 5. The results are shown in Table 3.

[1142] [Table 3]

[1143]

[1144] Example 9

[1145] <Fabrication of organic EL element>

[1146] An organic EL element is fabricated as described below.

[1147] A glass substrate (manufactured by Geomatic Corporation) with an ITO transparent electrode (anode) having a thickness 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 130 nm.

[1148] The cleaned glass substrate with a transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, on the surface where the transparent electrode was formed, compounds HT-3 and HI-1 were co-evaporated in such a way that the proportion of compound HI-1 reached 1% by mass to cover the transparent electrode, forming a first hole transport layer (hole injection layer) with a film thickness of 10 nm.

[1149] Compound HT-3 was evaporated on the first hole transport layer to form a second hole transport layer (hole transport layer) with a film thickness of 30 nm.

[1150] Compound 1 was evaporated on the second hole transport layer to form a third hole transport layer (hole transport layer) with a film thickness of 40 nm.

[1151] Compound HT-4 was evaporated on the third hole transport layer to form a fourth hole transport layer (electron blocking layer) with a film thickness of 15 nm.

[1152] On the third hole transport layer, compounds BH-5 (host material) and BD-3 (dopant material) were co-evaporated in such a way that the proportion of compound BD-3 reached 2% by mass to form a light-emitting layer with a film thickness of 20 nm.

[1153] Compound ET-5 was evaporated on the light-emitting layer to form a first electron transport layer with a film thickness of 10 nm.

[1154] On the first electron transport layer, compounds ET-6 and metal Li were co-evaporated in such a way that the proportion of metal Li reached 4% by mass to form a second electron transport layer with a film thickness of 20 nm.

[1155] Metal Al was evaporated on the second electron transport layer to form a cathode with a film thickness of 80 nm.

[1156] The element structure of the organic EL element of Example 8 is briefly shown as follows.

[1157] ITO(130) / HT-3:HI-1=99:1(10) / HT-3(30) / Compound 1(40) / HT-4(15) / BH-5:BD-3=98:2(20) / ET-5(10) / ET-6:Li=96:4(20) / Al(80)

[1158] The numbers in parentheses indicate the film thickness (unit: nm). Additionally, within the parentheses, the numbers expressed as percentages represent the proportion (mass %) of the latter compound in the layer.

[1159] The fabricated organic EL elements were evaluated as follows. The results are shown in Table 4.

[1160] · Ionization potential difference

[1161] Under atmospheric conditions, the ionization potential was measured using a photoelectron spectrometer ("AC-3" manufactured by Riken Keiki Co., Ltd.). Specifically, light was irradiated onto the compound to be measured, and the amount of electrons generated by charge separation at this time was measured to perform the measurement. The difference (ΔIp 2-3 = |Ip2 - Ip3|) between the ionization potential (Ip2) of the second hole transport layer material (compound HT-3) and the ionization potential (Ip3) of the third hole transport layer material (compound 1) is shown in Table 4.

[1162] · Refractive index difference

[1163] The refractive index (n2) of the material (compound) constituting the second hole transport layer and the refractive index (n3) of the material (compound) constituting the third hole transport layer were measured in the same manner as in Example 5, and the difference (Δn 2-3 = |n2 - n3|) was calculated.

[1164] · Driving voltage

[1165] At room temperature, the initial characteristics of the organic EL element were measured by driving with a DC (direct current) constant current of 10 mA / cm 2 ·

[1166] · External quantum efficiency

[1167] A voltage was applied to the organic EL element such that the current density reached 10 mA / cm 2 , and the EL emission spectrum was measured using a spectro-radiance meter CS-2000 (manufactured by Konica Minolta Inc.). The external quantum efficiency EQE (%) was calculated from the obtained spectro-radiance spectrum.

[1168] Comparative Examples 6 - 8

[1169] In the formation of the third hole transport layer, the compounds shown in Table 4 were used instead of compound 1, and otherwise, organic EL elements were fabricated and evaluated in the same manner as in Example 9. The results are shown in Table 4.

[1170] [Table 4]

[1171] Comparing the device of Example 9 with that of Comparative Example 6, it can be seen that the device of Example 9 has a lower driving voltage and a higher external quantum efficiency. This is considered to be because the difference in ionization potential (ΔIp 2-3 ) between the material constituting the second hole transport layer and the material constituting the third hole transport layer is small in the device of Example 9, resulting in improved hole injection as compared with the device of Comparative Example 6 where ΔIp 2-3 is large.

[1172] Comparing the device of Example 9 with that of Comparative Example 7, it can be seen that the device of Example 9 has a higher external quantum efficiency. This is considered to be because the difference in refractive index (Δn 2-3 ) between the material constituting the second hole transport layer and the material constituting the third hole transport layer is large in the device of Example 9, resulting in improved light extraction efficiency as compared with the device of Comparative Example 7 where Δn 2-3 is small.

[1173] <Synthesis of Compounds>

[1174] (Synthesis Example 1) Synthesis of Compound 1

[1175] Compound 1 was synthesized through the following synthetic route.

[1176] · Intermediate Synthesis Example 1: Synthesis of Intermediate A

[1177] [Chemical Formula 62]

[1178]

[1179] Under an argon atmosphere, a mixture of 2-(dibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (8 g, 27.2 mmol), 2-bromoaniline (4.68 g, 27.2 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.249 g, 0.272 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (Xphos) (0.519 g, 1.08 mmol), aqueous potassium phosphate solution (40.8 mL, 82 mmol), and 1,4-dioxane (181 mL) was stirred at 100 °C for 5 hours. The reaction solution was cooled to room temperature, water was added, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain Intermediate A as a pale yellow liquid (6.74 g). The yield was 96%.

[1180] · Intermediate Synthesis Example 2: Synthesis of Intermediate B

[1181] [Chemical Formula 63]

[1182]

[1183] Under argon atmosphere, a mixture of 1-dibenzothiophene (5 g, 19 mmol), 2-bromoaniline (4.16 g, 19 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.174 g, 0.19 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (Xphos) (0.362 g, 0.76 mmol), a potassium phosphate aqueous solution (28.5 mL, 57 mmol) and 1,4-dioxane (95 mL) was stirred at 100°C for 5 hours. The reaction solution was cooled to room temperature, water was added, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain intermediate B as a light yellow liquid (4 g). The yield was 76%.

[1184] Synthesis Example 1: Synthesis of Compound 1

[1185] [Chemistry 64]

[1186]

[1187] A mixture of intermediate A (6.7 g, 25.8 mmol), 2-bromo-9,9-dimethylfluorene (14.82 g, 54.3 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.473 g, 0.517 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.600 g, 2.067 mmol), sodium tert-butoxide (6.950 g, 72.3 mmol) and xylene (172 mL) was stirred at 120 ° C for 5 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 9.54 g of a white solid. The yield was 57%. The obtained substance was subjected to spectral analysis, and the result was compound 1, with a molecular weight of 643.83 and m / e=643.

[1188] Synthesis Example 2: Synthesis of Compound 2

[1189] [Chemistry 65]

[1190]

[1191] A mixture of intermediate B (4 g, 14.53 mmol), 2-bromo-9,9-dimethylfluorene (8.73 g, 32.0 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.266 g, 0.291 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.337 g, 1.162 mmol), sodium tert-butoxide (3.91 g, 40.7 mmol) and xylene (97 mL) was stirred at 120 ° C for 5 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 7.01 g of a white solid. The yield was 73%. The obtained substance was subjected to spectral analysis, and the result was compound 2, with a molecular weight of 659.89 and m / e=659.

[1192] Synthesis Example 3: Synthesis of Compound 3

[1193] [Chemistry 66]

[1194]

[1195] A mixture of intermediate A (10 g, 38.6 mmol), 2-bromo-9-methyl-9-phenylfluorene (26.5 g, 79 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.706 g, 0.771 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.895 g, 3.09 mmol), sodium tert-butoxide (10.4 g, 108 mmol) and xylene (250 mL) was stirred at 120°C for 5 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 13.78 g of a white solid. The yield was 46%. The obtained substance was subjected to spectral analysis, and the result was compound 3, with a molecular weight of 767.97 and m / e=768.

[1196] Synthesis Example 4: Synthesis of Compound 4

[1197] [Chemistry 67]

[1198]

[1199] A mixture of intermediate C (5.0 g, 12.5 mmol), intermediate D (3.5 g, 12.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (228 mg, 0.249 mmol), SPhos (409 mg, 0.996 mmol), sodium tert-butoxide (1.7 g, 17.4 mmol) and xylene (80 mL) was stirred at 120 °C for 5 hours. After cooling the reaction mixture to room temperature, it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to obtain 4.3 g of a white solid. The yield was 53%. The resulting substance was subjected to spectroscopic analysis, and the result was compound 4, with m / e = 648 relative to the molecular weight of 647.85.

[1200] · Synthesis Example 5: Synthesis of Compound 5

[1201] [Chemical Formula 68]

[1202]

[1203] A mixture of intermediate E (10.0 g, 18.5 mmol), intermediate F (5.2 g, 18.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (339 mg, 0.371 mmol), SPhos (609 mg, 1.5 mmol), sodium tert-butoxide (2.5 g, 25.9 mmol) and xylene (120 mL) was stirred at 120 °C for 10 hours. After cooling the reaction mixture to room temperature, it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to obtain 11.7 g of a white solid. The yield was 81%. The resulting substance was subjected to spectroscopic analysis, and the result was compound 5, with m / e = 782 relative to the molecular weight of 782.00.

[1204] · Synthesis Example 6: Synthesis of Compound 6

[1205] [Chemical Formula 69]

[1206]

[1207] A mixture of intermediate G (10 g, 19.5 mmol), 2-bromo-9,9-dimethylfluorene (5.58 g, 20.4 mmol), tris(dibenzylideneacetone)dipalladium (0) (357 mg, 0.389 mmol), tri-tert-butylphosphonium tetrafluoroborate (452 ​​mg, 1.6 mmol), sodium tert-butoxide (2.6 g, 27.3 mmol) and xylene (125 mL) was stirred at 120 ° C for 3 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 8.9 g of a white solid. The yield was 65%. The obtained substance was subjected to spectral analysis, and the result was compound 6, with a molecular weight of 705.90 and m / e=706.

[1208] Synthesis Example 7: Synthesis of Compound 7

[1209] [Chemistry 70]

[1210]

[1211] A mixture of intermediate H (10 g, 22.2 mmol), intermediate I (6.7 g, 22.2 mmol), tris(dibenzylideneacetone)dipalladium (0) (406 mg, 0.443 mmol), tri-tert-butylphosphonium tetrafluoroborate (514 mg, 1.8 mmol), sodium tert-butoxide (3.0 g, 31.0 mmol) and xylene (125 mL) was stirred at 120° C. for 5 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to obtain 12.2 g of a white solid. The yield was 77%. The resulting substance was subjected to spectral analysis, and the result was compound 7, with a molecular weight of 717.91 and m / e=718.

[1212] Several embodiments and / or examples of the present invention are described in detail above, but it is easy for those skilled in the art to make many changes to these illustrative embodiments and / or examples without actually departing from the novel teachings and effects of the present invention. Therefore, these many changes are also included in the scope of the present invention.

[1213] The contents of the documents described in this specification and the applications serving as the basis for the Paris Convention priority claim of the present application are incorporated herein by reference in their entirety.

Claims

1. The compound represented by the following formula (1), [Chemical formula 71] In formula (1), X 11 is an oxygen atom or a sulfur atom; Consisting of R 11 ~R 17 One or more groups, each group consisting of two or more adjacent ones among them, are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other; R that do not bond to each other 11 ~R 17 Each independently represents a hydrogen atom or a substituent R; One or more groups, each consisting of two or more adjacent ones among R1 to R4, are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other; When R1 to R4 are not bonded to each other, they are each independently: A hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms; Consisting of R 21 ~R 27 One or more groups each consisting of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other; R that do not bond to each other 21 ~R 27 Each independently represents a hydrogen atom or a substituent R; R 28 and R 29 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other; wherein, R 28 and R 29 When they are bonded to each other to form a substituted or unsubstituted fused ring, there is no case where a 9,9-spirobifluorene ring is formed together with the fluorene ring bonded to R 28 and R 29 ; R that do not bond to each other 28 and R 29 at least one of which is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; R that does not bond to each other and is not a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms 28 and R 29 each independently represents a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms; Composed of R 31 ~R 37 One or more groups each composed of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other; R that do not bond to each other 31 ~R 37 Each independently represents a hydrogen atom or a substituent R; R 38 and R 39 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other; wherein, R 38 and R 39 when they are bonded to each other to form a substituted or unsubstituted fused ring, there is no case where a 9,9-spirobifluorene ring is formed together with the fluorene ring to which R 38 and R 39 are bonded; R that do not bond to each other 38 and R 39 at least one of each independently is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; R which does not bond to each other and is not a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms 38 and R 39 are each independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms; L 11 , L 21 and L 31 Each independently is: A single bond, or A substituted or unsubstituted arylene group having 6 to 12 ring-forming carbon atoms; n11 is an integer from 0 to 3; When n11 is 0, (L 11 ) n11 is a single bond; When n11 is 2 or 3, multiple Ls 11 are connected in series with each other, and the tricyclic fused skeleton is bonded to the L farthest from the benzene skeleton 11 ; multiple Ls 11 can be the same or different; n21 is an integer from 0 to 3; When n21 is 0, (L 21 ) n21 is a single bond; When n21 is 2 or 3, multiple Ls 21 are connected in series with each other, and the fluorene skeleton is bonded to the L farthest from the nitrogen atom 21 ; The multiple Ls 21 can be the same or different; n31 is an integer from 0 to 3; When n31 is 0, (L 31 ) n31 is a single bond; When n31 is 2 or 3, multiple Ls 31 are connected in series with each other, and the fluorene skeleton is bonded to the L farthest from the nitrogen atom 31 ; the multiple Ls 31 can be the same or different; The substituent R is selected from: A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )、 -O-(R 904 )、 -S-(R 905 )、 -N(R 906 )(R 907 )、 A halogen atom, a cyano group, a nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms; When there are two or more substituents R, the two or more substituents R may be the same or different from each other; R 901 ~R 907 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-forming carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms; R 901 ~R 907 When there are two or more of each, two or more Rs 901 ~R 907 Each may be the same or different.

2. The compound according to claim 1, wherein R 28 and R 29 When they are bonded to each other to form a substituted or unsubstituted monocyclic or fused ring, the rings, and R 38 and R 39 When they are bonded to each other to form a substituted or unsubstituted monocyclic or fused ring, the rings are each independently selected from the rings represented by the following formulas (1a) to (1r), [Chemical formula 72] In formulas (1a) to (1r), C spiro represents R 28 and R 29 the carbon atom of the fluorene ring to which R 38 and R 39 are bonded; The carbon atoms constituting the ring have a hydrogen atom or a substituent R at the bondable positions; The substituent R is as defined in the above formula (1).

3. The compound according to claim 1, wherein R 28 and R 29 do not bond to each other, and R 28 is an alkyl group having 1 to 50 carbon atoms which may be substituted or unsubstituted, and R 29 is an alkyl group having 1 to 50 carbon atoms which may be substituted or unsubstituted or an aryl group having 6 to 50 ring-forming carbon atoms which may be substituted or unsubstituted, R 38 and R 39 do not bond to each other, and R 38 is an alkyl group having 1 to 50 carbon atoms which may be substituted or unsubstituted, and R 39 is an alkyl group having 1 to 50 carbon atoms which may be substituted or unsubstituted or an aryl group having 6 to 50 ring-forming carbon atoms which may be substituted or unsubstituted.

4. The compound according to claim 1, wherein R 28 and R 29 do not bond to each other, R 28 is an alkyl group having 1 to 5 carbon atoms which is substituted or unsubstituted, R 29 is an alkyl group having 1 to 5 carbon atoms which is substituted or unsubstituted or an aryl group having 6 to 10 ring-forming carbon atoms which is substituted or unsubstituted, R 38 and R 39 do not bond to each other, and R 38 is an alkyl group having 1 to 5 carbon atoms which is substituted or unsubstituted, and R 39 is an alkyl group having 1 to 5 carbon atoms which is substituted or unsubstituted or an aryl group having 6 to 10 ring-forming carbon atoms which is substituted or unsubstituted.

5. The compound according to claim 1 or 2, wherein, R 28 and R 29 do not bond to each other, and R 28 is an alkyl group having 1 to 50 carbon atoms which may be substituted or unsubstituted, and R 29 is an alkyl group having 1 to 50 carbon atoms which may be substituted or unsubstituted or an aryl group having 6 to 50 ring-forming carbon atoms which may be substituted or unsubstituted. R 38 and R 39 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring.

6. The compound according to claim 1 or 2, wherein, R 28 and R 29 do not bond to each other, and R 28 is an alkyl group having 1 to 5 carbon atoms which is substituted or unsubstituted, and R 29 is an alkyl group having 1 to 5 carbon atoms which is substituted or unsubstituted or an aryl group having 6 to 10 ring-forming carbon atoms which is substituted or unsubstituted. R 38 and R 39 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring.

7. The compound according to any one of claims 1 to 6, wherein R 21 ~R 27 and R 31 ~R 37 Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

8. The compound according to any one of claims 1 to 7, wherein R 21 ~R 27 and R 31 ~R 37 is a hydrogen atom.

9. The compound according to any one of claims 1 to 8, wherein, X 11 is an oxygen atom.

10. The compound according to any one of claims 1 to 9, wherein, R 11 ~R 17 Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

11. The compound according to any one of claims 1 to 10, wherein R 11 ~R 17 is a hydrogen atom.

12. The compound according to any one of claims 1 to 11, wherein, R1 to R4 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms.

13. The compound according to any one of claims 1 to 12, wherein, R1 to R4 are hydrogen atoms.

14. The compound according to any one of claims 1 to 13, wherein, L 11 、L 21 and L 31 each independently represents a single bond, or a substituted or unsubstituted phenylene group.

15. The compound according to any one of claims 1 to 14, wherein, L 11 、L 21 and L 31 are single bonds.

16. The compound according to any one of claims 1 to 7, wherein The compound represented by the above formula (1) is the compound represented by the following formula (1-1), [Chemical formula 73] In formula (1-1), X 11 , n11, n21, n31, L 11 , L 21 , L 31 , R 28 , R 29 , R 38 and R 39 are defined as in said formula (1).

17. The compound according to claim 1, wherein The compound represented by the above formula (1) is the compound represented by the following formula (1-11), [Chemical formula 74] In formula (1-11), X 11 , n11, n21, n31, L 11 , L 21 and L 31 are defined as in the said formula (1); R 128 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; R 129 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms; R 138 is an alkyl group having 1 to 50 carbon atoms which may or may not be substituted; R 139 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

18. The compound according to claim 1 or 2, wherein The compound represented by the above formula (1) is the compound represented by the following formula (1-21), [Chemical formula 75] In formula (1-21), X 11 , n11, n21, n31, L 11 , L 21 and L 31 are defined as in said formula (1); R 228 is an alkyl group having 1 to 50 carbon atoms which may or may not be substituted; R 229 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms; R 238 and R 239 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring; wherein, R 238 and R 239 when they are bonded to each other to form a substituted or unsubstituted fused ring, there is no case where a 9,9-spirobifluorene ring is formed together with the fluorene ring to which R 238 and R 239 are bonded.

19. The compound according to any one of claims 1 to 18, wherein, The compound represented by the above formula (1) contains at least one deuterium atom.

20. An organic electroluminescent element, which has: A cathode, An anode, A light-emitting layer disposed between the cathode and the anode, and A first layer disposed between the light-emitting layer and the anode; The first layer contains the compound according to any one of claims 1 to 19.

21. The organic electroluminescent element according to claim 20, which has a second layer between the first layer and the light-emitting layer.

22. The organic electroluminescent element according to claim 20 or 21, which has a third layer between the anode and the first layer.

23. The organic electroluminescent element according to claim 22, wherein, The third layer contains the compound according to any one of claims 1 to 19.

24. The organic electroluminescent element according to any one of claims 20 to 23, wherein The first layer has a first layer A and a first layer B starting from the anode side, The ionization potential Ip of the first layer A A and the ionization potential Ip of the first layer B B satisfy the following formula (E1), The refractive index n of the first layer A A and the refractive index n of the first layer B B satisfy the following formula (E2), |Ip A -Ip B |<0.20 [eV] ···(E1) |n A -n B | > 0.05 ··· (E2).

25. The organic electroluminescent element according to any one of claims 20 to 24, which has an electron transport region between the cathode and the light emitting layer.

26. An electronic device having the organic electroluminescent element according to any one of claims 20 to 25.

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