Organic electroluminescent element and electronic device

Abstract

An organic electroluminescent element (1) comprising an anode (3), a cathode (4), a light-emitting layer (5) disposed between the anode (3) and the cathode (4), and a first hole-transporting layer (71) disposed between the anode (3) and the light-emitting layer (5), the first hole-transporting layer (71) being directly adjacent to the light-emitting layer (5), the first hole-transporting layer (71) comprising a first compound represented by General Formula (1) below, the first compound having at least one group represented by General Formula (11) below.

Description

TECHNICAL FIELD

[0001] The present application relates to an organic electroluminescent element and an electronic device. BACKGROUND

[0002] An organic electroluminescent element (hereinafter sometimes referred to as "organic EL element") is applied to a full-color display of a mobile phone, a television, and the like. If a voltage is applied to the organic EL element, holes are injected from an anode to a light-emitting layer, and electrons are injected from a cathode to the light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons are recombined to form an exciton. At this time, according to the statistical rule of electron spin, a singlet exciton is generated at a ratio of 25%, and a triplet exciton is generated at a ratio of 75%.

[0003] In order to achieve improvement in performance of the organic EL element, various studies have been made on a compound used for the organic EL element (for example, refer to Patent Document 1 and Patent Document 2). Patent Document 1 and Patent Document 2 describe an organic electroluminescent element including a hole transport layer containing a compound having an amine skeleton.

[0004] As the performance of the organic EL element, for example, luminance, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime can be given.

[0005] PRIOR ART DOCUMENTS

[0006] PATENT DOCUMENTS

[0007] Patent Document 1: International Publication No. 2009 / 145016

[0008] Patent Document 2: International Publication No. 2010 / 061824

[0009] Patent Document 3: International Publication No. 2016 / 133058 SUMMARY

[0010] PROBLEMS TO BE SOLVED BY THE INVENTION

[0011] An object of the present application is to provide an organic electroluminescent element in which a driving voltage is decreased, and to provide an electronic device in which the organic electroluminescent element is mounted.

[0012] MEANS FOR SOLVING THE PROBLEMS

[0013] According to one aspect of the present application, there is provided an organic electroluminescent element including an anode, a cathode, a light-emitting layer disposed between the anode and the cathode, and a first hole transport layer disposed between the anode and the light-emitting layer, the first hole transport layer being directly adjacent to the light-emitting layer, the first hole transport layer including a first compound represented by the following general formula (1), the first compound having at least one group represented by the following general formula (11).

[0014] [Chemical Formula 1]

[0015]

[0016] (In the above general formula (1),

[0017] R 101 ~R 110 each independently is

[0018] a hydrogen atom,

[0019] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,

[0020] a substituted or unsubstituted haloalkyl group having a carbon number of 1 to 50,

[0021] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,

[0022] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,

[0023] a substituted or unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 50,

[0024] a group represented by -Si(R 901 )(R 902 )(R 903 ),

[0025] a group represented by -O-(R 904 ),

[0026] a group represented by -S-(R 905 ),

[0027] a substituted or unsubstituted aralkyl group having a carbon number of 7 to 50,

[0028] a group represented by -C(=O)R 801 ,

[0029] a group represented by -COOR 802 ,

[0030] a halogen atom,

[0031] a cyano group,

[0032] a nitro group,

[0033] a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50,

[0034] a substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50, or

[0035] a group represented by the above general formula (11),

[0036] wherein R101 ~R 110 at least one of R1to R4in the above general formula (11) is a group represented by the above general formula (11),

[0037] in the case where a plurality of groups represented by the above general formula (11) are present, the plurality of groups represented by the above general formula (11) are the same as or different from each other,

[0038] L 101 is

[0039] a single bond,

[0040] a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or

[0041] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms,

[0042] Ar 101 is

[0043] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or

[0044] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,

[0045] mxis 0, 1, 2, 3, 4, or 5,

[0046] in the case where two or more L's are present, the two or more L's are the same as or different from each other, 101 101

[0047] in the case where two or more Ar's are present, the two or more Ar's are the same as or different from each other, 101 101

[0048] * in the above general formula (11) represents a bonding position to the pyrene ring in the above general formula (1),

[0049] in the above first compound, the substituent in the expression "substituted or unsubstituted" is selected from the group consisting of

[0050] an unsubstituted alkyl group having 1 to 50 carbon atoms,

[0051] an unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0052] an unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0053] an unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[0054] -Si(R 901 )(R 902 )(R 903 ), and ​​​​

[0055] -O-(R 904 ),

[0056] -S-(R 905 ),

[0057] Halogen atoms,

[0058] cyano,

[0059] Nitro,

[0060] Unsubstituted aryl groups with 6 to 50 carbon atoms, and

[0061] At least one group from the group consisting of unsubstituted heterocyclic groups having 5 to 50 cyclic atoms.

[0062] In the first compound represented by the above general formula (1), R 901 R 902 R 903 R 904 R 905 R 801 and R 802 Each independently

[0063] hydrogen atom,

[0064] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0065] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0066] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0067] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0068] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.

[0069] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.

[0070] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.

[0071] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.

[0072] In R 905 In the case of multiple Rs, multiple Rs 905They are the same or different.

[0073] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[0074] In R 802 In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)

[0075] According to one aspect of the present invention, an electronic device is provided, which is equipped with the organic electroluminescent element described above.

[0076] According to one aspect of the present invention, an organic electroluminescent element with a reduced driving voltage can be provided. Furthermore, according to another aspect of the present invention, an electronic device incorporating the organic electroluminescent element can be provided. Attached Figure Description

[0077] Figure 1 This is a diagram illustrating the general configuration of an example of an organic electroluminescent element according to one embodiment of the present invention.

[0078] Figure 2 This is a diagram illustrating the general configuration of an example of an organic electroluminescent element according to one embodiment of the present invention.

[0079] Figure 3 This is a diagram illustrating the general configuration of an example of an organic electroluminescent element according to one embodiment of the present invention.

[0080] Figure 4 This is a diagram illustrating the general configuration of an example of an organic electroluminescent element according to one embodiment of the present invention. Detailed Implementation

[0081] [definition]

[0082] In this specification, a hydrogen atom means an isotope containing different numbers of neutrons, namely protium, deuterium, and tritium.

[0083] In this specification, the chemical structural formula does not explicitly show that the bonding positions of symbols such as "R" and "D" representing deuterium atoms are set to be bonded to hydrogen atoms, i.e., protium atoms, deuterium atoms, or tritium atoms.

[0084] In this specification, the number of carbon atoms forming a ring refers to the number of carbon atoms in the ring itself of a compound whose atoms are bonded in a ring (e.g., monocyclic compounds, fused-ring compounds, bridged-ring compounds, carbocyclic compounds, and heterocyclic compounds). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of carbon atoms forming the ring. The term "number of carbon atoms forming a ring" is used as described below unless otherwise specified. For example, the number of carbon atoms forming a ring is 6 for a benzene ring, 10 for a naphthalene ring, 5 for a pyridine ring, and 4 for a furan ring. Additionally, for example, the number of carbon atoms forming a ring is 13 for 9,9-diphenylfluoreneyl and 25 for 9,9'-spirobifluoreneyl.

[0085] Furthermore, when a benzene ring is substituted with an alkyl group, the carbon number of the alkyl group is not included in the number of carbon atoms in the ring-forming process of the benzene ring. Therefore, the number of carbon atoms in the cyclic benzene ring substituted with an alkyl group is 6. Similarly, when a naphthalene ring is substituted with an alkyl group, the carbon number of the alkyl group is not included in the number of carbon atoms in the ring-forming process of the naphthalene ring. Therefore, the number of carbon atoms in the cyclic naphthalene ring substituted with an alkyl group is 10.

[0086] In this specification, the number of cyclic atoms refers to the number of atoms constituting the ring itself in compounds (e.g., monocyclic compounds, fused-ring compounds, bridged-ring compounds, carbocyclic compounds, and heterocyclic compounds) where atoms are bonded in a ring structure (e.g., monocyclic, fused-ring, and aggregated-ring). Atoms that do not constitute a ring (e.g., hydrogen atoms that end the bonds of the ring-forming atoms) and atoms contained in substituents when the ring is substituted are not included in the number of cyclic atoms. The term "number of cyclic atoms" as used below is the same unless otherwise stated. For example, the number of cyclic atoms in a pyridine ring is 6, in a quinazoline ring it is 10, and in a furan ring it is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or atoms constituting substituents are not included in the number of cyclic atoms in pyridine. Therefore, the number of cyclic atoms in a pyridine ring bonded with hydrogen atoms or substituents is 6. Furthermore, hydrogen atoms bonded to the carbon atoms of the quinazoline ring, or atoms constituting substituents, are not included in the number of cyclic atoms of the quinazoline ring. Therefore, the number of cyclic atoms in a quinazoline ring with bonded hydrogen atoms or substituents is 10.

[0087] In this specification, the phrase "ZZ group with substituted or unsubstituted carbon numbers of XX to YY" indicates the number of carbons when the ZZ group is unsubstituted; the number of carbons in substituents is not included. Here, "YY" is greater than "XX," where "XX" refers to an integer greater than 1, and "YY" refers to an integer greater than 2.

[0088] In this specification, the phrase "ZZ group with substituted or unsubstituted atoms of XX to YY" refers to the number of atoms when the ZZ group is unsubstituted, excluding the number of atoms of substituents when substitution has occurred. Here, "YY" is greater than "XX", where "XX" is an integer greater than or equal to 1, and "YY" is an integer greater than or equal to 2.

[0089] In this specification, "unsubstituted ZZ group" means "substituted or unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".

[0090] In this specification, "unsubstituted" when referred to as "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group has not been substituted with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0091] Furthermore, in this specification, "substitution" when expressed as "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group have been replaced by a substituent. Similarly, "substitution" when expressed as "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group have been replaced by an AA group.

[0092] Substituents described in this specification

[0093] The substituents described in this specification are explained below.

[0094] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted aryl group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0095] Unless otherwise stated in this specification, the number of cyclic atoms in the "unsubstituted heterocyclic group" is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0096] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0097] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkenyl group" is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0098] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkynyl group" is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0099] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted cycloalkyl group" is 3 to 50, preferably 3 to 20, and more preferably 3 to 6.

[0100] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted aryl group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0101] Unless otherwise stated in this specification, the number of cyclic atoms in the "unsubstituted divalent heterocyclic group" is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0102] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkylene group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0103] • "Substituted or unsubstituted aryl groups"

[0104] Specific examples of "substituted or unsubstituted aryl" as described in this specification (specific example group G1) include unsubstituted aryl (specific example group G1A) and substituted aryl (specific example group G1B), etc. (Here, unsubstituted aryl refers to the case where "substituted or unsubstituted aryl" is "unsubstituted aryl", and substituted aryl refers to the case where "substituted or unsubstituted aryl" is "substituted aryl".) In this specification, when referred to only as "aryl", both "unsubstituted aryl" and "substituted aryl" are included.

[0105] "Substituted aryl" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl" group have been substituted with a substituent. Examples of "substituted aryl" include the group in Specific Example Group G1A below in which one or more hydrogen atoms of an "unsubstituted aryl" group have been substituted with a substituent, and the substituted aryl group in Specific Example Group G1B below. It should be noted that the examples of "unsubstituted aryl" and "substituted aryl" listed here are only examples. The "substituted aryl" described in this specification also includes the group in Specific Example Group G1B below in which hydrogen atoms bonded to the carbon atom of the aryl group itself have been further substituted with a substituent, and the group in Specific Example Group G1B below in which hydrogen atoms of the substituent have been further substituted with a substituent.

[0106] • Unsubstituted aryl groups (specific example group G1A):

[0107] phenyl,

[0108] p-phenyl,

[0109] metaphenyl,

[0110] o-phenyl,

[0111] p-terphenyl-4-yl,

[0112] p-terphenyl-3-yl,

[0113] p-terphenyl-2-yl,

[0114] m-terphenyl-4-yl,

[0115] m-terphenyl-3-yl,

[0116] m-terphenyl-2-yl,

[0117] o-terphenyl-4-yl

[0118] o-terphenyl-3-yl

[0119] o-terphenyl-2-yl,

[0120] 1-Naphthyl,

[0121] 2-Naphthyl,

[0122] anthracene,

[0123] Benzanthracene,

[0124] Fiki,

[0125] Benzphenanthrene,

[0126] Finadenyl,

[0127] Pyrene

[0128] base,

[0129] benzo[a] base,

[0130] Tri-phenylene,

[0131] Benzotrimethylene

[0132] phenylene,

[0133] Pentaphenyl,

[0134] Fluorine

[0135] 9,9'-spirobisfluorene,

[0136] benzo[f]fluorenyl,

[0137] Dibenzofluorene,

[0138] Fluoranthene group,

[0139] Benzofluoranthyl,

[0140] Perylene and monovalent aryl groups derived from the ring structures shown in the following general formulas (TEMP-1) to (TEMP-15) by removing one hydrogen atom.

[0141]

Chemical Formula 2

[0142]

[0143]

Chemical Formula 3

[0144]

[0145] • Substituted aryl groups (specific example group G1B):

[0146] o-Tolyl,

[0147] m-Tolyl,

[0148] p-Tolyl,

[0149] p-Xylyl,

[0150] m-Xylyl,

[0151] o-xylyl,

[0152] p-isopropylphenyl,

[0153] m-Isopropylphenyl,

[0154] o-isopropylphenyl,

[0155] p-tert-butylphenyl,

[0156] m-tert-butylphenyl,

[0157] o-tert-butylphenyl,

[0158] 3,4,5-Trimethylphenyl,

[0159] 9,9-Dimethylfluorenyl,

[0160] 9,9-Diphenylfluorenyl,

[0161] 9,9-bis(4-methylphenyl)fluorenyl,

[0162] 9,9-Bis(4-isopropylphenyl)fluorenyl,

[0163] 9,9-Bis(4-tert-butylphenyl)fluorenyl,

[0164] cyanophenyl,

[0165] Triphenylsilylphenyl

[0166] Trimethylsilylphenyl

[0167] Phenynaphthyl,

[0168] Naphthylphenyl and groups in which one or more hydrogen atoms of a monovalent group derived from the ring structure shown in the above general formulas (TEMP-1) to (TEMP-15) have been replaced by substituents.

[0169] • "Substituted or unsubstituted heterocyclic groups"

[0170] The term "heterocyclic group" as used in this specification refers to a cyclic group whose cyclic atoms contain at least one heteroatom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.

[0171] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.

[0172] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0173] Specific examples of "substituted or unsubstituted heterocyclic groups" described in this specification (specific example group G2) include unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B), etc. (Here, unsubstituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group", and substituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group".) In this specification, the term "heterocyclic group" includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".

[0174] "Substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" have been substituted with a substituent. Specific examples of "substituted heterocyclic groups" include the group in Example Group G2A below where the hydrogen atoms of the "unsubstituted heterocyclic group" have been substituted, and the example of a substituted heterocyclic group in Example Group G2B below. It should be noted that the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are only examples. The "substituted heterocyclic groups" described in this specification also include the group in Example Group G2B where the hydrogen atoms bonded to the cyclic atoms of the heterocyclic group itself have been further substituted with a substituent, and the group in Example Group G2B where the hydrogen atoms of the substituent have been further substituted with a substituent.

[0175] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1), unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2), unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3), and monovalent heterocyclic groups derived from the ring structures shown in the following general formulas (TEMP-16) to (TEMP-33) by removing one hydrogen atom (specific example group G2A4).

[0176] Specific example group G2B includes, for example, the following: a nitrogen-containing substituted heterocyclic group (specific example group G2B1), an oxygen-containing substituted heterocyclic group (specific example group G2B2), a sulfur-containing substituted heterocyclic group (specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) have been substituted with a substituent (specific example group G2B4).

[0177] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1):

[0178] pyrrole,

[0179] Imidazole group,

[0180] Pyrazolyl,

[0181] Triazole group,

[0182] Tetrazolyl,

[0183] Oxazolyl,

[0184] Isoxazolyl,

[0185] Oxadiazole group,

[0186] Thiazole group,

[0187] Isothiazolyl,

[0188] Thiadiazole group,

[0189] pyridyl,

[0190] pyridazinyl,

[0191] Pyrimidinyl,

[0192] Pyrazinyl,

[0193] Triazine group

[0194] Indole,

[0195] Isoindolyl,

[0196] Indazine-based

[0197] Quinazine-based

[0198] Quinoline,

[0199] Isoquinoline,

[0200] Crenoline group

[0201] Phthaloazine

[0202] Quinazolinyl,

[0203] Quinoxaloyl,

[0204] Benzimidazole group,

[0205] Indazole group,

[0206] phenanthroline,

[0207] phenanthridine,

[0208] acridine group,

[0209] Phenazine group,

[0210] Carbazole group,

[0211] Benzocarbazolyl,

[0212] Morpholinyl

[0213] phenoxazine group,

[0214] phenothiazine group,

[0215] Azacarbazolyl and diazacarbazolyl.

[0216] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2):

[0217] furanyl,

[0218] Oxazolyl,

[0219] Isoxazolyl,

[0220] Oxadiazole group,

[0221] Xuton base,

[0222] Benzofuranyl,

[0223] Isobenzofuranyl,

[0224] Dibenzofuranyl,

[0225] Naphthobenzofuranyl,

[0226] Benzoxazolyl,

[0227] Benzisoxazole group,

[0228] phenoxazine group,

[0229] Morpholinyl

[0230] Dinaphthylfuranyl,

[0231] Azadibenzofuranyl,

[0232] diazadibenzofuranyl,

[0233] Azanaphthobenzofuranyl and diazanaphthobenzofuranyl.

[0234] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3):

[0235] Thiophene group

[0236] Thiazole group,

[0237] Isothiazolyl,

[0238] Thiadiazole group,

[0239] benzothienyl

[0240] isobenzothienyl

[0241] dibenzothienyl

[0242] Naphthobenzothienyl

[0243] Benzothiazolyl,

[0244] Benzisothiazolyl,

[0245] phenothiazine group,

[0246] dinaphthothienyl

[0247] azadibenzothienyl

[0248] diazadibenzothienyl

[0249] Azanaphthobenzothienyl and diazanaphthobenzothienyl.

[0250] • The monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures shown in the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0251] [Chemical Formula 4]

[0252]

[0253] [Chemical Formula 5]

[0254]

[0255] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each can be independently composed of an oxygen atom, a sulfur atom, NH, or CH2. Among them, X... A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH.

[0256] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A When at least one of them is NH or CH2, the monovalent heterocyclic group derived from the ring structure shown in the above general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0257] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1):

[0258] (9-phenyl)carbazole group,

[0259] (9-Biphenyl)carbazolyl,

[0260] (9-Phenyl)phenylcarbazolyl,

[0261] (9-Naphthyl)carbazole,

[0262] Diphenylcarbazole-9-yl,

[0263] Phenylexacarbazole-9-yl,

[0264] Methylbenzimidazole,

[0265] Ethylbenzimidazole,

[0266] Phenylacetyl,

[0267] Biphenyltriazine

[0268] diphenyltriazine group,

[0269] Phenylacetinyl and biphenylquinazolinyl.

[0270] • Heterocyclic groups containing oxygen atoms (specific example group G2B2):

[0271] Phenyl dibenzofuranyl,

[0272] Methyldibenzofuranyl,

[0273] The monovalent residues of tert-butyldibenzofuranyl and spiro[9H-xanton-9,9'-[9H]fluorene].

[0274] • Heterocyclic groups containing sulfur atoms (specific example group G2B3):

[0275] Phenyl dibenzothiophene,

[0276] Methyldibenzothiophene,

[0277] The monovalent residues of tert-butyldibenzothiophene and spiro[9H-thiophene-9,9'-[9H]fluorene].

[0278] • Groups derived from the ring structures shown in the above general formulas (TEMP-16) to (TEMP-33) in which one or more hydrogen atoms of a monovalent heterocyclic group have been substituted with substituents (specific example group G2B4):

[0279] The aforementioned "one or more hydrogen atoms of a monovalent heterocyclic group" refers to one or more hydrogen atoms selected from the following: hydrogen atoms bonded to the cyclic carbon atom of the monovalent heterocyclic group, hydrogen atoms bonded to the nitrogen atom when at least one of XA and YA is NH, and hydrogen atoms of the methylene group when one of XA and YA is CH2.

[0280] • "Substituted or unsubstituted alkyl groups"

[0281] As specific examples of "substituted or unsubstituted alkyl" described in this specification (specific example group G3), the following unsubstituted alkyl (specific example group G3A) and substituted alkyl (specific example group G3B) can be cited. (Here, unsubstituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when referred to as "alkyl", both "unsubstituted alkyl" and "substituted alkyl" are included.

[0282] "Substituted alkyl" refers to a group in which one or more hydrogen atoms of an "unsubstituted alkyl" have been substituted with a substituent. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms of an "unsubstituted alkyl" (specific example group G3A) have been substituted with a substituent, and examples of substituted alkyl (specific example group G3B). In this specification, "unsubstituted alkyl" refers to a chain-like alkyl group. Therefore, "unsubstituted alkyl" includes both straight-chain and branched-chain unsubstituted alkyl groups. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples; the "substituted alkyl" described in this specification also includes groups in which the hydrogen atoms of the alkyl group in specific example group G3B have been further substituted with a substituent, and groups in which the hydrogen atoms of the substituents in specific example group G3B have been further substituted with a substituent.

[0283] • Unsubstituted alkyl groups (specific example group G3A):

[0284] methyl,

[0285] Ethyl,

[0286] n-propyl,

[0287] Isopropyl,

[0288] n-Butyl,

[0289] Isobutyl,

[0290] Sec-butyl and tert-butyl.

[0291] • Substituted alkyl groups (specific example group G3B):

[0292] Heptafluoropropyl (including isomers),

[0293] Pentafluoroethyl,

[0294] 2,2,2-Trifluoroethyl and trifluoromethyl.

[0295] • "Substituted or unsubstituted alkenyl groups"

[0296] Specific examples of "substituted or unsubstituted alkenyl groups" (specific example group G4) described in this specification include unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "substituted alkenyl group".) In this specification, when simply referred to as "alkenyl group", both "unsubstituted alkenyl group" and "substituted alkenyl group" are included.

[0297] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" group have been substituted with a substituent. Specific examples of "substituted alkenyl" include the "unsubstituted alkenyl" group (specific example group G4A) having a substituent and examples of substituted alkenyl groups (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples; the "substituted alkenyl" described in this specification also includes groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the alkenyl itself have been further substituted with a substituent, and groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the substituent have been further substituted with a substituent.

[0298] • Unsubstituted alkenyl groups (specific example group G4A):

[0299] vinyl,

[0300] Allyl

[0301] 1-Butenyl,

[0302] 2-Butenyl and 3-Butenyl.

[0303] • Substituted alkenyl groups (specific example group G4B):

[0304] 1,3-Butadienyl,

[0305] 1-Methylvinyl

[0306] 1-Methylallyl,

[0307] 1,1-Dimethylallyl,

[0308] 2-Methylallyl and 1,2-dimethylallyl.

[0309] • "Substituted or unsubstituted alkynyl groups"

[0310] As specific examples of "substituted or unsubstituted alkynyl groups" described in this specification (specific example group G5), the following unsubstituted alkynyl groups (specific example group G5A) can be cited. (Here, unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group".) The following description of "alkynyl group" includes both "unsubstituted alkynyl group" and "substituted alkynyl group".

[0311] "Substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" have been replaced by a substituent. Specific examples of "substituted alkynyl group" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl group" (specific example group G5A) have been replaced by a substituent.

[0312] • Unsubstituted alkynyl group (specific example group G5A): ethynyl group.

[0313] • "Substituted or unsubstituted cycloalkyl groups"

[0314] Specific examples of "substituted or unsubstituted cycloalkyl" described in this specification (specific example group G6) include unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B), etc. (Here, unsubstituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl".) In this specification, when referred to only as "cycloalkyl", both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.

[0315] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group have been substituted with a substituent. Specific examples of "substituted cycloalkyl" include the group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group (specific example group G6A) have been substituted with a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples. The "substituted cycloalkyl" described in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl" group of specific example group G6B have been substituted with a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted cycloalkyl" group of specific example group G6B have been further substituted with a substituent.

[0316] • Unsubstituted cycloalkyl groups (specific example group G6A):

[0317] Cyclopropyl

[0318] Cyclobutyl,

[0319] Cyclopentyl,

[0320] Cyclohexyl,

[0321] 1-Adamantyl,

[0322] 2-Adamantyl,

[0323] 1-norborneol and 2-norborneol.

[0324] • Substituted cycloalkyl group (specific example group G6B): 4-methylcyclohexyl.

[0325] ·"-Si(R 901 (R) 902 (R)903 The group shown in the figure”

[0326] As described in this specification, -Si(R) 901 (R) 902 (R) 903 Specific examples of the group shown in the figure (specific example group G7) can be given as follows:

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

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

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

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

[0331] -Si(G3)(G3)(G3) and -Si(G6)(G6)(G6). Here,

[0332] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0333] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0334] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0335] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0336] In -Si(G1)(G1)(G1), multiple G1s may be the same or different from each other.

[0337] In -Si(G1)(G2)(G2), multiple G2s may be the same or different from each other.

[0338] In -Si(G1)(G1)(G2), multiple G1s may be the same or different from each other.

[0339] In -Si(G2)(G2)(G2), multiple G2s may be the same or different from each other.

[0340] In -Si(G3)(G3)(G3), multiple G3s may be the same or different from each other.

[0341] In -Si(G6)(G6)(G6), multiple G6s may be the same or different from each other.

[0342] ·“-O-(R 904 The group shown in the figure”

[0343] As described in this specification, -O-(R)904 Specific examples of the group shown (specific example group G8) can be given as follows:

[0344] -O(G1)

[0345] -O(G2),

[0346] -O(G3) and -O(G6).

[0347] Here,

[0348] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0349] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0350] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0351] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0352] ·“-S-(R 905 The group shown in the figure”

[0353] As described in this specification, -S-(R) 905 Specific examples of the group shown (specific example group G9) can be given as follows:

[0354] -S(G1)

[0355] -S(G2),

[0356] -S(G3) and -S(G6).

[0357] Here,

[0358] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0359] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0360] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0361] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0362] ·"-N(R 906 (R) 907 The group shown in the figure”

[0363] As described in this specification, -N(R) 906 (R) 907Specific examples of the group shown (specific example group G10) can be given as follows:

[0364] -N(G1)(G1),

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

[0366] -N(G1)(G2),

[0367] -N(G3)(G3) and -N(G6)(G6).

[0368] Here,

[0369] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0370] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0371] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0372] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0373] In -N(G1)(G1), multiple G1s may be the same or different from each other.

[0374] In -N(G2)(G2), multiple G2 values ​​may be the same or different from each other.

[0375] In -N(G3)(G3), multiple G3s may be the same or different from each other.

[0376] In -N(G6)(G6), multiple G6 values ​​may be the same or different from each other.

[0377] • "Halogen atom"

[0378] Specific examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0379] • "Substituted or unsubstituted fluoroalkyl groups"

[0380] The term "substituted or unsubstituted fluoroalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group has been replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group have been replaced by fluorine atoms (perfluorinated groups). Unless otherwise specified in this specification, the number of carbon atoms in an "unsubstituted fluoroalkyl" group is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted fluoroalkyl" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl" group have been replaced by a substituent. It should be noted that the term "substituted fluoroalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in a "substituted fluoroalkyl" group have been further replaced by a substituent, and groups in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl" group have been further replaced by a substituent. As a specific example of "unsubstituted fluoroalkyl", examples can be given of groups in which one or more hydrogen atoms in the above-mentioned "alkyl" (specific example group G3) have been replaced by fluorine atoms.

[0381] • "Substituted or unsubstituted haloalkyl groups"

[0382] The term "substituted or unsubstituted haloalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group has been replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group have been replaced by halogen atoms. Unless otherwise specified in this specification, the number of carbon atoms in an "unsubstituted haloalkyl" group is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted haloalkyl" refers to a group in which one or more hydrogen atoms of a "haloalkyl" group have been replaced by a substituent. It should be noted that "substituted haloalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in a "substituted haloalkyl" group have been further replaced by a substituent, and groups in which one or more hydrogen atoms of a substituent in a "substituted haloalkyl" group have been further replaced by a substituent. As a specific example of "unsubstituted haloalkyl", examples can be given of groups in which one or more hydrogen atoms of the above-mentioned "alkyl" (specific example group G3) have been substituted with halogen atoms. Haloalkyl is sometimes called haloalkyl.

[0383] • "Substituted or unsubstituted alkoxy groups"

[0384] As a specific example of "substituted or unsubstituted alkoxy group" as described in this specification, it is the group indicated by -O (G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0385] • "Substituted or unsubstituted alkylthio groups"

[0386] As a specific example of "substituted or unsubstituted alkylthio group" as described in this specification, it is the group indicated by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0387] • "Substituted or unsubstituted aryloxy groups"

[0388] As a specific example of "substituted or unsubstituted aryloxy group" as described in this specification, it is the group indicated by -O (G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of carbon atoms in the ring of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0389] • "Substituted or unsubstituted arylthio groups"

[0390] As a specific example of "substituted or unsubstituted arylthio group" as described in this specification, it is the group indicated by -S(G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of carbon atoms in the ring of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0391] • "Substituted or unsubstituted trialkylsilyl groups"

[0392] As a specific example of "trialkylsilyl" as described in this specification, it is the group represented by -Si(G3)(G3)(G3), where G3 refers to the "substituted or unsubstituted alkyl" described in the specific example group G3. The plurality of G3s in -Si(G3)(G3)(G3) may be identical or different from each other. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the "trialkylsilyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0393] • "Substituted or unsubstituted aralkyl groups"

[0394] As a specific example of "substituted or unsubstituted aralkyl" as described in this specification, it is the group shown as -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl" described in specific example group G3, and G1 is the "substituted or unsubstituted aryl" described in specific example group G1. Therefore, "aralkyl" is a group in which the hydrogen atom of "alkyl" is replaced by "aryl" as a substituent, and is one embodiment of "substituted alkyl". "Unsubstituted aralkyl" is an "unsubstituted alkyl" that is substituted with "unsubstituted aryl", and the number of carbon atoms of "unsubstituted aralkyl" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.

[0395] Specific examples of "substituted or unsubstituted aralkyl groups" 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.

[0396] Unless otherwise specified in this specification, the substituted or unsubstituted aryl groups described herein are preferably phenyl, p-phenyl, meta-phenyl, o-phenyl, 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, anthraceneyl, phenanthryl, pyreneyl, etc. It includes methyl, triphenyl, fluorenyl, 9,9'-spirobisfluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl, etc.

[0397] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic groups described herein are preferably pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, phenanthrolinel, carbazole (1-carbazole, 2-carbazole, 3-carbazole, 4-carbazole, or 9-carbazole), benzocarbazole, azacarbazole, diazacarbazole, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophene, and naphtho-benzofuranyl. Benzothiophene, azadibenzothiophene, diazadibenzothiophene, (9-phenyl)carbazoyl ((9-phenyl)carbazo-1-yl, (9-phenyl)carbazo-2-yl, (9-phenyl)carbazo-3-yl, or (9-phenyl)carbazo-4-yl), (9-biphenyl)carbazoyl, (9-phenyl)phenylcarbazoyl, diphenylcarbazo-9-yl, phenylcarbazo-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl, and phenyldibenzothiophene, etc.

[0398] In this specification, the carbazoyl group, unless otherwise specified herein, specifically refers to any one of the following groups.

[0399]

Chemical Formula 6

[0400]

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

[0402] [Chemical Formula 7]

[0403]

[0404] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.

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

[0406] [Chemical Formula 8]

[0407]

[0408] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.

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

[0410] • "Substituted or unsubstituted aryl groups"

[0411] Unless otherwise stated, the "substituted or unsubstituted aryl group" described in this specification refers to a divalent group derived from the "substituted or unsubstituted aryl group" by removing one hydrogen atom from the aryl ring. Specific examples of "substituted or unsubstituted aryl group" (specific example group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in specific example group G1 by removing one hydrogen atom from the aryl ring.

[0412] • "Substituted or unsubstituted divalent heterocyclic groups"

[0413] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification refers to a divalent group derived from the aforementioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom from the heterocycle. Specific examples of "substituted or unsubstituted divalent heterocyclic groups" (specific example group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in specific example group G2 by removing one hydrogen atom from the heterocycle.

[0414] • "Substituted or unsubstituted alkylene compounds"

[0415] Unless otherwise stated, "substituted or unsubstituted alkylene" as described in this specification refers to a divalent group derived from the aforementioned "substituted or unsubstituted alkyl" by removing one hydrogen atom from the alkyl chain. Specific examples of "substituted or unsubstituted alkylene" (Specific Example Group G14) include divalent groups derived from the "substituted or unsubstituted alkyl" described in Specific Example Group G3 by removing one hydrogen atom from the alkyl chain.

[0416] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described herein is preferably any one of the groups in 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 10 Each can be a hydrogen atom or a substituent independently.

[0422] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.

[0423]

Chemical Formula 11

[0424]

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

[0426] Formulas Q9 and Q 10 They can form rings by bonding with each other via single bonds.

[0427] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.

[0428]

Chemical Formula 12

[0429]

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

[0431] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.

[0432] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described herein 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 above 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 an explanation of "substituents described in this specification".

[0450] • "Cases where bonds form rings"

[0451] In this specification, the description of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring, or bonded together to form a substituted or unsubstituted fused ring, or not bonded together" refers to the cases of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring", "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted fused ring", and "one or more groups of two or more adjacent elements not bonded together".

[0452] The following description addresses the cases where "one or more groups of two or more adjacent rings are bonded together to form a substituted or unsubstituted monocyclic ring" and "one or more groups of two or more adjacent rings are bonded together to form a substituted or unsubstituted fused ring" (hereinafter, these cases are sometimes collectively referred to as "the case of forming a ring by bonding"). The case of anthracene compounds with the following general formula (TEMP-103) whose parent skeleton is anthracene ring will be used as an example.

[0453]

Chemical Formula 20

[0454]

[0455] For example, in R 921 ~R 930 In the case of "one or more groups of two or more adjacent elements bonded together to form a loop", the group consisting of two adjacent elements as a group refers to R. 921 With R 922 group, R 922 With R 923 group, R 923 With R 924 group, R 924 With R 930 group, R930 With R 925 group, R 925 With R 926 group, R 926 With R 927 group, R 927 With R 928 group, R 928 With R 929 The group and R 929 With R 921 The group.

[0456] The phrase "one or more groups" refers to the fact that two or more of the aforementioned adjacent groups can simultaneously form a loop. For example, in R... 921 With R 922 They bond together to form a ring Q A Moreover, R 925 With R 926 They bond together to form a ring Q B When the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104), it is also represented by the following general formula (TEMP-104).

[0457]

Chemical Formula 21

[0458]

[0459] The formation of rings from "groups of two or more adjacent elements" includes not only the case of bonds formed by groups of "two" adjacent elements, as in the previous example, but also the case of bonds formed by groups of "three or more" adjacent elements. For example, it refers to R... 921 With R 922 They bond together to form a ring Q A And R 922 With R 923 They bond together to form a ring Q C , consisting of 3 adjacent (R) 921 R 922 and R 923 When the groups of components Q bond together to form a ring and fuse to the anthracene matrix, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q... A and ring Q C There are a total of R 922 .

[0460]

Chemical Formula 22

[0461]

[0462] In the formed "single ring" or "fused ring," the structure of the ring alone can be either a saturated ring or an unsaturated ring. Even when "one of the groups of two adjacent rings" forms a "single ring" or "fused ring," that "single ring" or "fused ring" can form either a saturated ring or an unsaturated ring. For example, the ring Q formed in the above general formula (TEMP-104) A and ring Q B Each is either a "single ring" or a "fused ring". Additionally, the ring Q formed in the above general formula (TEMP-105) A and Q ring C It is a "fused ring". The ring Q of the above general formula (TEMP-105) A With ring Q C Through ring Q A With ring Q C Fusing occurs, forming a fused ring. If the ring Q of the above general formula (TMEP-104) A If it is a benzene ring, then ring Q A It is a single ring. If the ring Q of the above general formula (TMEP-104) is... A If it is a naphthalene ring, then ring Q A It is a fused ring.

[0463] "Unsaturated rings" refer to aromatic hydrocarbon rings or aromatic heterocycles. "Saturated rings" refer to aliphatic hydrocarbon rings or non-aromatic heterocycles.

[0464] As a specific example of an aromatic hydrocarbon ring, the structure formed by the hydrogen atom-terminated group in specific example group G1 can be cited.

[0465] As a specific example of an aromatic heterocycle, one can cite the structure formed by end-capping an aromatic heterocycle group with hydrogen atoms in specific example group G2.

[0466] As a specific example of an aliphatic hydrocarbon ring, the structure formed by the hydrogen atom-terminated group in specific example group G6 can be cited.

[0467] "Ring formation" refers to the formation of a ring solely by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton forming a ring with one or more other optional elements. For example, R shown in the above general formula (TEMP-104) 921 With R 922 The ring Q formed by mutual bonding A It refers to R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 The carbon atoms of the bonded anthracene framework form rings with one or more optional elements. As a specific example, in the case of R... 921 With R 922 Forming ring Q A In the case of R921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 When the bonded anthracene skeleton carbon atoms and 4 carbon atoms form a monocyclic unsaturated ring, R 921 With R 922 The resulting ring is a benzene ring.

[0468] Here, "optional element" is preferably selected from at least one element chosen from the group consisting of carbon, nitrogen, oxygen, and sulfur, unless otherwise specified in this specification. In the case of optional elements (e.g., carbon or nitrogen), non-ring bonds can be capped by hydrogen atoms or replaced by "optional substituents" described later. When optional elements other than carbon are included, the resulting ring is a heterocycle.

[0469] Unless otherwise specified in this specification, the "one or more optional elements" constituting a monocyclic or fused ring are preferably two or more and 15 or less, more preferably three or more and 12 or less, and even more preferably three or more and 5 or less.

[0470] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".

[0471] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".

[0472] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.

[0473] Unless otherwise stated in this specification, the "unsaturated ring" is preferably a benzene ring.

[0474] In the case of "one or more groups of two or more adjacent atoms forming a substituted or unsubstituted monocyclic ring" or "a substituted or unsubstituted fused ring formed by mutual bonding", unless otherwise stated in this specification, it is preferred that one or more groups of two or more adjacent atoms form an unsaturated ring formed by mutual bonding of a plurality of atoms of a parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0475] When the aforementioned "monocyclic" or "fused-ring" rings have substituents, the substituents are, for example, the "optional substituents" described later. Specific examples of substituents when the aforementioned "monocyclic" or "fused-ring" rings have substituents are the substituents described in the section "Substituents Represented in This Specification" above.

[0476] When the aforementioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of substituents when the aforementioned "monocyclic" or "fused ring" has a substituent are the substituents described in the section "Substituents Represented in This Specification" above.

[0477] The above explains the cases of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring" and "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted fused ring" ("the case of bonding to form a ring").

[0478] Substituents when described as "substituted or unsubstituted"

[0479] In one embodiment of this specification, the substituents described above as "substituted or unsubstituted" (sometimes referred to as "optional substituents" in this specification) are, for example, selected from unsubstituted alkyl groups having 1 to 50 carbon atoms.

[0480] Unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0481] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms

[0482] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0483] -Si(R 901 (R) 902 (R) 903 ),

[0484] -O-(R 904 ),

[0485] -S-(R 905 ),

[0486] -N(R 906 (R) 907 ),

[0487] Halogen atom, cyano group, nitro group,

[0488] Groups in the group consisting of unsubstituted aryl groups with 6 to 50 carbon atoms and unsubstituted heterocyclic groups with 5 to 50 atoms.

[0489] Here, R 901 ~R 907 Each independently

[0490] hydrogen atom,

[0491] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0492] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0493] A substituted or unsubstituted aryl group with 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms.

[0494] In R 901 In cases where there are two or more R's, there are two or more R's. 901 They are the same or different.

[0495] In R 902 In cases where there are two or more R's, there are two or more R's. 902 They are the same or different.

[0496] In R 903 In cases where there are two or more R's, there are two or more R's. 903 They are the same or different.

[0497] In R 904 In cases where there are two or more R's, there are two or more R's. 904 They are the same or different.

[0498] In R 905 In cases where there are two or more R's, there are two or more R's. 905 They are the same or different.

[0499] In R 906 In cases where there are two or more R's, there are two or more R's. 906 They are the same or different.

[0500] In R 907 In cases where there are two or more R's, there are two or more R's. 907 They are the same or different.

[0501] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.

[0502] Alkyl groups with 1 to 50 carbon atoms

[0503] Groups in the group consisting of aryl groups with 6 to 50 carbon atoms and heterocyclic groups with 5 to 50 atoms.

[0504] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.

[0505] Alkyl groups having 1 to 18 carbon atoms

[0506] Groups in the group consisting of aryl groups with 6 to 18 carbon atoms and heterocyclic groups with 5 to 18 atoms.

[0507] Specific examples of each of the optional substituents are those described in the section "Substituents as described in this specification" above.

[0508] Unless otherwise stated in this specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring" with each other, preferably forming a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably forming a benzene ring.

[0509] Unless otherwise stated in this specification, optional substituents may also have other substituents. Any further substituents that may be present as optional substituents are the same as those described above.

[0510] In this specification, the numerical range referred to as "AA~BB" refers to the range included by taking the value AA recorded before "AA~BB" as the lower limit and the value BB recorded after "AA~BB" as the upper limit.

[0511] [First Implementation]

[0512] (Organic electroluminescent device)

[0513] The organic electroluminescent element according to this embodiment includes an anode, a cathode, a light-emitting layer disposed between the anode and the cathode, and a first hole transport layer disposed between the anode and the light-emitting layer. The first hole transport layer is directly adjacent to the light-emitting layer. The first hole transport layer contains a first compound represented by the following general formula (1). The first compound has at least one group represented by the following general formula (11).

[0514] (Emitting wavelength of organic EL devices)

[0515] The organic electroluminescent element involved in this embodiment preferably emits light with a maximum peak wavelength of 430 nm or more and 480 nm or less when the element is driven.

[0516] The maximum peak wavelength of light emitted by the organic EL element during element driving was determined as follows. A voltage was applied to the organic EL element such that the current density was 10 mA / cm². 2 The spectroradiance spectrum at that time was measured using a CS-2000 spectroradiometer (manufactured by Konica Minolta). The peak wavelength of the emission spectrum with the highest luminous intensity was determined from the obtained spectroradiance spectrum and taken as the maximum peak wavelength (unit: nm).

[0517] In addition to the light-emitting layer and the first hole transport layer, the organic EL element according to this embodiment may have one or more organic layers. Examples of organic layers include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, an electron transport layer, a hole blocking layer, and an electron blocking layer.

[0518] In the organic EL element of this embodiment, the organic layer may consist only of a light-emitting layer and a first hole transport layer, or it may also have at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole blocking layer, and an electron blocking layer.

[0519] (Electron transport layer)

[0520] In the organic EL element of this embodiment, it is preferable to have an electron transport layer between the cathode and the light-emitting layer.

[0521] Figure 1 The diagram shows a general configuration of an example of an organic EL element involved in this embodiment.

[0522] The organic EL element 1 includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is formed by stacking a hole injection layer 6, a first hole transport layer 71, a light-emitting layer 5, an electron transport layer 8, and an electron injection layer 9 in sequence from the anode 3 side.

[0523] (First hole transport layer)

[0524] The first hole transport layer is directly adjacent to the light-emitting layer. The first hole transport layer contains a first compound represented by the following general formula (1).

[0525] The thickness of the first hole transport layer is preferably less than 15 nm.

[0526] The thickness of the first hole transport layer is preferably 2 nm or more.

[0527] The thickness of the first hole transport layer is more preferably 2 nm or more and 10 nm or less, and even more preferably 2 nm or more and 5 nm or less.

[0528] ·First compound

[0529] The first compound is a compound represented by the following general formula (1). The first compound has at least one group represented by the following general formula (11).

[0530]

Chemical Formula 23

[0531]

[0532] In the above general formula (1),

[0533] R 101 ~R 110 Each independently

[0534] hydrogen atom,

[0535] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0536] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0537] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0538] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0539] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0540] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0541] -O-(R 904 The groups shown in the figure,

[0542] -S-(R 905 The groups shown in the figure,

[0543] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0544] -C(=O)R 801 The groups shown

[0545] -COOR 802 The groups shown

[0546] Halogen atoms,

[0547] cyano,

[0548] Nitro,

[0549] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms

[0550] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or

[0551] The groups represented by the above general formula (11),

[0552] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11) above.

[0553] When there are multiple groups represented by the above general formula (11), the multiple groups represented by the above general formula (11) may be the same as or different from each other.

[0554] L 101 for

[0555] single bond,

[0556] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[0557] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0558] Ar 101 for

[0559] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0560] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0561] mx is 0, 1, 2, 3, 4, or 5.

[0562] In L 101 When there are more than two, more than two L 101 They are the same or different.

[0563] In Ar 101 In the case of two or more Ar, two or more Ar 101 They are the same or different.

[0564] In the above general formula (11), * indicates the bonding position with the pyrene ring in the above general formula (1).

[0565] In the first compound, the substituents, when described as "substituted or unsubstituted," are selected freely.

[0566] Unsubstituted alkyl groups with 1 to 50 carbon atoms

[0567] Unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0568] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms

[0569] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0570] -Si(R 901 (R) 902 (R) 903 ),

[0571] -O-(R 904 ),

[0572] -S-(R 905 ),

[0573] Halogen atoms,

[0574] cyano,

[0575] Nitro,

[0576] Unsubstituted aryl groups with 6 to 50 carbon atoms, and

[0577] At least one group from the group consisting of unsubstituted heterocyclic groups with 5 to 50 cyclic atoms.

[0578] In the first compound represented by the above general formula (1), R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently

[0579] hydrogen atom,

[0580] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0581] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0582] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0583] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0584] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.

[0585] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.

[0586] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.

[0587] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.

[0588] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.

[0589] In R 906In the case of multiple Rs, multiple Rs 906 They are the same or different.

[0590] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.

[0591] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[0592] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.

[0593] The heterocyclic group in the first compound is preferably a group containing at least one of oxygen or sulfur atoms.

[0594] The group represented by the above general formula (11) is preferably the group represented by the following general formula (111).

[0595]

Chemical Formula 24

[0596]

[0597] (In the above general formula (111),

[0598] X1 is CR 123 R 124 oxygen atom, sulfur atom or NR 125 ,

[0599] L 111 and L 112 Each independently

[0600] single bond,

[0601] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[0602] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0603] ma is 0, 1, 2, 3 or 4.

[0604] mb can be 0, 1, 2, 3, or 4.

[0605] ma+mb is 0, 1, 2, 3 or 4.

[0606] Ar 101 Ar in the above general formula (11) 101 Same meaning

[0607] R 121 R 122R 123 R 124 and R 125 Each independently

[0608] hydrogen atom,

[0609] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0610] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0611] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0612] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0613] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0614] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0615] -O-(R 904 The groups shown in the figure,

[0616] -S-(R 905 The groups shown in the figure,

[0617] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0618] -C(=O)R 801 The groups shown

[0619] -COOR 802 The groups shown

[0620] Halogen atoms,

[0621] cyano,

[0622] Nitro,

[0623] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0624] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0625] mc is 3.

[0626] 3 Rs 121 They are the same or different.

[0627] md is 3

[0628] 3 Rs 122 (They may be the same or different.)

[0629] In the group represented by the above general formula (111), at positions *1 to *8 of the carbon atoms in the ring structure represented by the following general formula (111a), L 111 Bonded to any position from *1 to *4, R 121 Bonded to the remaining 3 positions in *1 to *4, L 112 Bonded to any position from *5 to *8, R 122 It is bonded to the other 3 positions in *5 to *8.

[0630] [Chemical Formula 25]

[0631]

[0632] For example, in the groups shown in the above general formula (111), in L 111 The position of the carbon atom *2 bonded to the ring structure shown in the above general formula (111a), L 112 When the carbon atom of *7 in the ring structure shown in the above general formula (111a) is bonded, the group shown in the above general formula (111) is represented by the following general formula (111b).

[0633]

Chemical Formula 26

[0634]

[0635] (In the above general formula (111b),

[0636] X1, L 111 L 112 ma, mb, Ar 101 R 121 R 122 R 123 R 124 and R 125 Each independently relates to X1 and L in the above general formula (111). 111 L 112 ma, mb, Ar 101 R 121 R 122 R 123 R 124 and R 125 Same meaning

[0637] Multiple R 121 They are the same or different.

[0638] Multiple R 122 (They may be the same or different.)

[0639] In the organic EL element of this embodiment, the group represented by the above general formula (111) is preferably the group represented by the above general formula (111b).

[0640] In the organic EL element involved in this embodiment, it is preferred that ma is 0, 1 or 2, and mb is 0, 1 or 2.

[0641] In the organic EL element involved in this embodiment, it is preferred that ma is 0 or 1 and mb is 0 or 1.

[0642] In the group represented by the above general formula (111), when ma is 0 and mb is 1, the group represented by the above general formula (111) is represented by the following general formula (111c).

[0643] [Chemical Formula 27]

[0644]

[0645] (In the above general formula (111c), X1, L 112 ,mc,md,Ar 101 R 121 and R 122 Each independently relates to X1 and L in the above general formula (111). 112 ,mc,md,Ar 101 R 121 and R 122 The meaning is the same.

[0646] In the organic EL element involved in this embodiment, Ar 101 Preferably, it is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[0647] In the organic EL element involved in this embodiment, Ar 101 Preferably, it is a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted pyrene, a substituted or unsubstituted phenanthryl, or a substituted or unsubstituted fluorene.

[0648] In the organic EL element involved in this embodiment, Ar 101 It is also preferred to use the groups shown in general formula (12), general formula (13) or general formula (14) below.

[0649] [Chemical Formula 28]

[0650]

[0651] (In the above general formulas (12), (13) and (14),

[0652] R111 ~R 120 Each independently

[0653] hydrogen atom,

[0654] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0655] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0656] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0657] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0658] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0659] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0660] -O-(R 904 The groups shown in the figure,

[0661] -S-(R 905 The groups shown in the figure,

[0662] -N(R 906 (R) 907 The groups shown in the figure,

[0663] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0664] -C(=O)R 124 The groups shown

[0665] -COOR 125 The groups shown

[0666] Halogen atoms,

[0667] cyano,

[0668] Nitro,

[0669] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0670] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0671] In the above general formulas (12), (13), and (14), * indicates the same as L in the above general formula (11). 101 The bonding position, or the L in the above general formulas (111), (111b), (111c) 112 (The bonding location.)

[0672] R in the above general formulas (12), (13) and (14) 124 and R 125 It is also preferable that each is independent of the aforementioned R. 801 and R 802 They have the same meaning.

[0673] The first compound is preferably represented by the following general formula (101).

[0674] [Chemical Formula 29]

[0675]

[0676] (In the above general formula (101),

[0677] R 101 ~R 120 Each independently

[0678] hydrogen atom,

[0679] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0680] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0681] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0682] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0683] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0684] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0685] -O-(R 904 The groups shown in the figure,

[0686] -S-(R 905 The groups shown in the figure,

[0687] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0688] -C(=O)R 801 The groups shown

[0689] -COOR 802 The groups shown

[0690] Halogen atoms,

[0691] cyano,

[0692] Nitro,

[0693] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0694] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0695] Among them, R 101 ~R 110 One of them represents L 101 The bonding position, R 111 ~R 120 One of them represents L 101 The bonding position,

[0696] L 101 for

[0697] single bond,

[0698] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[0699] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0700] mx is 0, 1, 2, 3, 4, or 5.

[0701] In L 101 When there are more than two, more than two L 101 (They may be the same or different.)

[0702] In the above general formula (101), R 103 To be with L 101 The bonding position, R 120 To be with L 101 In the case of the bonding positions, the compound represented by the above general formula (101) is represented by the following general formula (101A).

[0703]

Chemical Formula 30

[0704]

[0705] (In the above general formula (101A), R) 101 R 102 R 104 ~R 119 L 101 And mx are respectively related to R in the above general formula (101) 101 R 102 R 104 ~R 119 L 101 (Same meaning as mx)

[0706] In the organic EL element involved in this embodiment, L 101 Preferably, it is a single bond, or a cyclic aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[0707] In the organic EL element involved in this embodiment, the first compound is preferably represented by the following general formula (102).

[0708]

Chemical Formula 31

[0709]

[0710] (In the above general formula (102),

[0711] R 101 ~R 120 Each independently relates to R in the above general formula (101). 101 ~R 120 Same meaning

[0712] Among them, R 101 ~R 110 One of them represents L 111 The bonding position, R 111 ~R 120 One of them represents L 112 The bonding position,

[0713] X1 is CR 123 R 124 oxygen atom, sulfur atom or NR 125 ,

[0714] L 111 and L 112 Each independently

[0715] single bond,

[0716] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[0717] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0718] ma is 0, 1, 2, 3 or 4.

[0719] mb can be 0, 1, 2, 3, or 4.

[0720] ma+mb is 0, 1, 2, 3 or 4.

[0721] R 121 R 122 R 123 R 124 and R 125 Each independently

[0722] hydrogen atom,

[0723] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0724] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0725] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0726] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0727] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0728] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0729] -O-(R 904 The groups shown in the figure,

[0730] -S-(R 905 The groups shown in the figure,

[0731] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0732] -C(=O)R 801 The groups shown

[0733] -COOR 802 The groups shown

[0734] Halogen atoms,

[0735] cyano,

[0736] Nitro,

[0737] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0738] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0739] mc is 3.

[0740] 3 Rs 121 They are the same or different.

[0741] md is 3

[0742] 3 Rs 122 (They may be the same or different.)

[0743] In the compounds represented by the above general formula (102), preferably, ma is 0, 1 or 2, and mb is 0, 1 or 2.

[0744] In the compounds represented by the above general formula (102), preferably, ma is 0 or 1 and mb is 0 or 1.

[0745] In the organic EL element involved in this embodiment, R is preferred. 101 ~R 110 Two or more of them are groups represented by the general formula (11) above.

[0746] In the organic EL element involved in this embodiment, R is preferred. 101 ~R 110 Two or more of them are groups represented by the general formula (11) above, and Ar 101 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[0747] In the organic EL element involved in this embodiment, it is preferred that,

[0748] Ar 101 It is neither a substituted nor an unsubstituted pyrene group.

[0749] L 101 It is neither a replaced nor unreplaced pyrene group.

[0750] R, which is not a group represented by the above general formula (11) 101 ~R 110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is not a substituted or unsubstituted pyrene group.

[0751] In the organic EL element involved in this embodiment, it is preferred that,

[0752] R is not a group represented by the general formula (11) above. 101 ~R 110 Each independently

[0753] hydrogen atom,

[0754] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0755] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0756] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0757] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0758] In the organic EL element involved in this embodiment, it is preferred that,

[0759] R is not a group represented by the general formula (11) above. 101 ~R 110 Each independently

[0760] hydrogen atom,

[0761] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or

[0762] Cycloalkyl groups, substituted or unsubstituted, having 3 to 50 carbon atoms.

[0763] In the organic EL element involved in this embodiment, the R group is not the group shown in the above general formula (11). 101 ~R 110 Hydrogen atoms are preferred.

[0764] In the organic EL element involved in this embodiment, X1 is preferably CR. 123 R 124 For example, when X1 is CR 123 R 124 In the case of the above general formula (111), the group represented by the above general formula (111d) is represented by the following general formula (111d).

[0765]

Chemical Formula 32

[0766]

[0767] (In the above general formula (111d), L) 111 L 112 ,ma,mb,ma+mb,Ar 101 R 121 R 122 R 123 R 124 R 125 , mc and md are defined in the same way as in the general formula (111) above.

[0768] In the organic EL element involved in this embodiment, R is preferred. 123 With R 124 They do not bond with each other.

[0769] In the organic EL element involved in this embodiment, L is preferred. 111 and L 112 At least one of them is

[0770] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[0771] A divalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0772] In the first compound, when described as "substituted or unsubstituted", the substituents preferably do not contain substituted or unsubstituted pyrene groups.

[0773] In one embodiment, the first compound is a compound having only one pyrene ring in its molecule (sometimes referred to as a monopyrene compound).

[0774] In one embodiment, the first compound is a compound having only two pyrene rings in its molecule (sometimes referred to as a bispyrene compound).

[0775] In the first compound, groups described as "substituted or unsubstituted" are preferably "unsubstituted".

[0776] The first hole transport layer preferably does not contain compounds with amino groups.

[0777] The first hole transport layer preferably does not contain compounds containing nitrogen and boron atoms.

[0778] In the organic EL element of this embodiment, the content of the first compound in the first hole transport layer is preferably 90% by mass or more, and more preferably 99% by mass or more.

[0779] In the organic EL element of this embodiment, the first hole transport layer is further preferably formed only of the first compound described above.

[0780] In the organic EL element involved in this embodiment, the first hole transport layer preferably does not emit light with a maximum peak wavelength of 430 nm or more and 480 nm or less when the element is driven.

[0781] (Method for manufacturing the first compound)

[0782] The first compound can be manufactured using known methods. Alternatively, the first compound can also be manufactured by using known alternative reactions and starting materials corresponding to the target substance, following the known methods.

[0783] (Specific examples of the first compound)

[0784] Specific examples of the first compound include the following compounds. However, the present invention is not limited to these specific examples of the first compound.

[0785]

Chemical Formula 33

[0786]

[0787] [Chemical Formula 34]

[0788]

[0789]

Chemical Formula 35

[0790]

[0791]

Chemical Formula 36

[0792]

[0793]

Chemical Formula 37

[0794]

[0795] [Chemical Formula 38]

[0796]

[0797] [Chemical Formula 39]

[0798]

[0799]

Chemical Formula 40

[0800]

[0801]

Chemical Formula 41

[0802]

[0803]

Chemical Formula 42

[0804]

[0805]

Chemical Formula 43

[0806]

[0807]

Chemical Formula 44

[0808]

[0809] [Chemical Formula 45]

[0810]

[0811]

Chemical Formula 46

[0812]

[0813] [Chemical Formula 47]

[0814]

[0815] [Chemical Formula 48]

[0816]

[0817] [Chemical Formula 49]

[0818]

[0819] [Chemical Formula 50]

[0820]

[0821]

Chemical Formula 51

[0822]

[0823]

Chemical Formula 52

[0824]

[0825]

Chemical Formula 53

[0826]

[0827] [Chemical Formula 54]

[0828]

[0829]

Chemical Formula 55

[0830]

[0831] [Chemical Formula 56]

[0832]

[0833] [Chemical Formula 57]

[0834]

[0835] (Emitting layer)

[0836] In the organic EL element of this embodiment, the light-emitting layer preferably contains a second compound with fluorescent properties.

[0837] In the organic EL element of this embodiment, when the light-emitting layer contains a second compound and a third compound, the third compound is preferably a host material (sometimes also called a matrix material), and the second compound is preferably a dopant material (sometimes also called a guest material, emitter, or light-emitting material).

[0838] In this specification, "main material" refers to a material, for example, comprising "50% by mass or more of the layer". Therefore, for example, the light-emitting layer contains, as an example, the third compound represented by the above-described general formula (1) or the following general formula (2) comprising 50% by mass or more of the total mass of the light-emitting layer. Furthermore, for example, the content of the "main material" may be 60% by mass or more of the layer, 70% by mass or more of the layer, 80% by mass or more of the layer, 90% by mass or more of the layer, or 95% by mass or more of the layer.

[0839] In the organic EL element involved in this embodiment, the light-emitting layer preferably contains a pyrene derivative, and more preferably contains a pyrene derivative as the main material.

[0840] In the organic EL element involved in this embodiment, the light-emitting layer preferably contains anthracene derivatives, and more preferably contains anthracene derivatives as the main material.

[0841] The light-emitting layer preferably does not contain phosphorescent materials as dopants.

[0842] Furthermore, the light-emitting layer preferably does not contain heavy metal complexes or phosphorescent rare-earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.

[0843] In addition, the light-emitting layer preferably does not contain metal complexes.

[0844] (Multiple light-emitting layers)

[0845] In one embodiment, the light-emitting layer of the organic EL element may also be composed of multiple light-emitting layers.

[0846] One embodiment of the organic EL element includes, for example, a first light-emitting layer and a second light-emitting layer disposed between the first light-emitting layer and a cathode. In this case, the organic EL element sequentially includes a first hole transport layer, a first light-emitting layer, and a second light-emitting layer from the anode side, with the first hole transport layer directly connected to the first light-emitting layer. Preferably, the first light-emitting layer and the second light-emitting layer are directly connected.

[0847] Figure 3 The diagram shows the general configuration of another example of the organic EL element involved in this embodiment.

[0848] The organic EL element 1B includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is formed by stacking a hole injection layer 6, a first hole transport layer 71, a light-emitting layer 5, an electron transport layer 8, and an electron injection layer 9 in sequence from the anode 3 side. The light-emitting layer 5 further includes a first light-emitting layer 51 and a second light-emitting layer 52.

[0849] The first and second light-emitting layers preferably each independently contain fluorescent compounds.

[0850] The fluorescent compounds contained in the first and second light-emitting layers are preferably compounds that exhibit luminescence with a maximum peak wavelength of 430 nm or more and 480 nm or less.

[0851] The first luminescent layer preferably contains a second and a third compound that exhibit fluorescence. In this case, the third compound in the first luminescent layer is preferably a host material (sometimes also called a matrix material), and the second compound is preferably a dopant material (sometimes also called a guest material, emitter, or luminescent material).

[0852] The second luminescent layer preferably contains a fourth and a fifth fluorescent compound. In this case, the fifth compound in the second luminescent layer is preferably a host material (sometimes also called a matrix material), and the fourth compound is preferably a dopant material (sometimes also called a guest material, emitter, or luminescent material). The fourth fluorescent compound in the second luminescent layer can be the same compound as the second compound described above. The second fluorescent compound in the first luminescent layer may be the same as or different from the fourth fluorescent compound in the second luminescent layer. The fifth compound in the second luminescent layer can be the same compound as the third compound described above. The third compound in the first luminescent layer may be the same as or different from the fifth compound in the second luminescent layer.

[0853] The first light-emitting layer preferably contains a pyrene derivative, and more preferably contains a pyrene derivative as the main material.

[0854] The second light-emitting layer preferably contains anthracene derivatives, and more preferably contains anthracene derivatives as the main material.

[0855] More preferably, the first light-emitting layer contains a pyrene derivative as the main material, and the second light-emitting layer contains an anthracene derivative as the main material.

[0856] The first and second light-emitting layers preferably do not contain phosphorescent materials as dopants.

[0857] Furthermore, the first and second light-emitting layers preferably do not contain heavy metal complexes or phosphorescent rare-earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.

[0858] In addition, the first and second light-emitting layers preferably do not contain metal complexes.

[0859] Compound 2 and Compound 4

[0860] The second compound and the fourth compound are each independently one or more compounds selected from the group consisting of the compound represented by general formula (3), the compound represented by general formula (4), the compound represented by general formula (5), the compound represented by general formula (6), the compound represented by general formula (7), the compound represented by general formula (8), the compound represented by general formula (9), and the compound represented by general formula (10).

[0861] (The compound represented by general formula (3))

[0862] The compounds represented by general formula (3) will be described.

[0863] [Chemical Formula 58]

[0864]

[0865] (In the above general formula (3),

[0866] R 301 ~R 310 One or more of the groups consisting of two or more adjacent elements.

[0867] They bond together to form substituted or unsubstituted monocyclic rings.

[0868] They bond together to form substituted or unsubstituted fused rings, or

[0869] They do not bond with each other.

[0870] R 301 ~R 310 At least one of them is a monovalent group represented by the following general formula (31),

[0871] R that does not form the above-mentioned monocyclic ring, does not form the above-mentioned fused ring, and is not a monovalent group represented by the following general formula (31) 301 ~R 310 Each independently

[0872] hydrogen atom,

[0873] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0874] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0875] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0876] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0877] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0878] -O-(R 904 The groups shown in the figure,

[0879] -S-(R 905 The groups shown in the figure,

[0880] -N(R 906 (R) 907 The groups shown in the figure,

[0881] Halogen atoms,

[0882] cyano,

[0883] Nitro,

[0884] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0885] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[0886] [Chemical Formula 59]

[0887]

[0888] (In the above general formula (31),

[0889] Ar 301 and Ar 302 Each independently

[0890] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0891] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0892] L 301 ~L 303 Each independently

[0893] single bond,

[0894] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or

[0895] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.

[0896] * indicates the bonding position in the pyrene ring in the above general formula (3).

[0897] In the second compound, R 901 R 902 R 903 R 904 R 905 R 906 and R 907 Each independently

[0898] hydrogen atom,

[0899] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0900] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0901] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0902] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0903] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or

[0904] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.

[0905] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.

[0906] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.

[0907] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.

[0908] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.

[0909] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.

[0910] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.

[0911] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.

[0912] In the above general formula (3), R is preferred. 301 ~R 310 Two of them are groups represented by the general formula (31) above.

[0913] In one embodiment, the compound represented by the above general formula (3) is the compound represented by the following general formula (33).

[0914] [Chemical Formula 60]

[0915]

[0916] (In the above general formula (33),

[0917] R 311 ~R 318 Each independently interacts with the R group in the above general formula (3) that is not a monovalent group represented by the above general formula (31). 301~R 310 Same meaning

[0918] L 311 ~L 316 Each independently

[0919] single bond,

[0920] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or

[0921] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.

[0922] Ar 312 Ar 313 Ar 315 and Ar 316 Each independently

[0923] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0924] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[0925] In the above general formula (31), L 301 Preferably a single bond, L 302 and L 303 Single bonds are preferred.

[0926] In one embodiment, the compound represented by the above general formula (3) is represented by the following general formula (34) or general formula (35).

[0927]

Chemical Formula 61

[0928]

[0929] (In the above general formula (34),

[0930] R 311 ~R 318 Each independently relates to the R301~R group in the above general formula (3) that is not a monovalent group represented by the above general formula (31). 310 Same meaning

[0931] L 312 L 313 L 315 and L 316 Each independently relates to L in the above general formula (33) 312 L 313 L 315 and L 316 Same meaning

[0932] Ar 312 Ar 313 Ar315 and Ar 316 Each independently relates to Ar in the above general formula (33) 312 Ar 313 Ar 315 and Ar 316 The meaning is the same.

[0933]

Chemical Formula 62

[0934]

[0935] (In the above general formula (35),

[0936] R 311 ~R 318 Each independently interacts with the R group in the above general formula (3) that is not a monovalent group represented by the above general formula (31). 301 ~R 310 Same meaning

[0937] Ar 312 Ar 313 Ar 315 and Ar 316 Each independently relates to Ar in the above general formula (33) 312 Ar 313 Ar 315 and Ar 316 The meaning is the same.

[0938] In the above general formula (31), Ar is preferred. 301 and Ar 302 At least one of them is a group represented by the following general formula (36).

[0939] In the above general formulas (33) to (35), Ar is preferred. 312 and Ar 313 At least one of them is a group represented by the following general formula (36).

[0940] In the above general formulas (33) to (35), Ar is preferred. 315 and Ar 316 At least one of them is a group represented by the following general formula (36).

[0941]

Chemical Formula 63

[0942]

[0943] (In the above general formula (36),

[0944] X3 represents an oxygen atom or a sulfur atom.

[0945] R 321 ~R327 One or more of the groups consisting of two or more adjacent elements.

[0946] They bond together to form substituted or unsubstituted monocyclic rings.

[0947] They bond together to form substituted or unsubstituted fused rings, or

[0948] They do not bond with each other.

[0949] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 321 ~R 327 Each independently

[0950] hydrogen atom,

[0951] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0952] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0953] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0954] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0955] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0956] -O-(R 904 The groups shown in the figure,

[0957] -S-(R 905 The groups shown in the figure,

[0958] -N(R 906 (R) 907 The groups shown in the figure,

[0959] Halogen atoms,

[0960] cyano,

[0961] Nitro,

[0962] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0963] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0964] * indicates that L 302 L 303 L 312 L 313 L 315 or L 316 (The bonding location.)

[0965] X3 is preferably an oxygen atom.

[0966] Preferred R 321 ~R 327 At least one of them is

[0967] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0968] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0969] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0970] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0971] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0972] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0973] In the above general formula (31), Ar is preferred. 301 For the group represented by the above general formula (36), Ar 302 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[0974] In the above general formulas (33) to (35), Ar is preferred. 312 For the group represented by the above general formula (36), Ar 313 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[0975] In the above general formulas (33) to (35), Ar is preferred. 315 For the group represented by the above general formula (36), Ar 316 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[0976] In one embodiment, the compound represented by the above general formula (3) is represented by the following general formula (37).

[0977]

Chemical Formula 64

[0978]

[0979] (In the above general formula (37),

[0980] R 311 ~R 318 Each independently interacts with the R group in the above general formula (3) that is not a monovalent group represented by the above general formula (31). 301 ~R 310 Same meaning

[0981] R 321 ~R 327 One or more of the groups consisting of two or more adjacent elements.

[0982] They bond together to form substituted or unsubstituted monocyclic rings.

[0983] They bond together to form substituted or unsubstituted fused rings, or

[0984] They do not bond with each other.

[0985] R 341 ~R 347 One or more of the groups consisting of two or more adjacent elements.

[0986] They bond together to form substituted or unsubstituted monocyclic rings.

[0987] They bond together to form substituted or unsubstituted fused rings, or

[0988] They do not bond with each other.

[0989] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 321 ~R 327 and R 341 ~R 347 Each independently

[0990] hydrogen atom,

[0991] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0992] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0993] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0994] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0995] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0996] -O-(R 904 The groups shown in the figure,

[0997] -S-(R 905 The groups shown in the figure,

[0998] -N(R 906 (R) 907 The groups shown in the figure,

[0999] Halogen atoms,

[1000] cyano,

[1001] Nitro,

[1002] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1003] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1004] R 331 ~R 335 and R 351 ~R 355 Each independently

[1005] hydrogen atom,

[1006] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1007] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1008] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1009] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1010] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1011] -O-(R 904 The groups shown in the figure,

[1012] -S-(R 905 The groups shown in the figure,

[1013] -N(R 906 (R) 907 The groups shown in the figure,

[1014] Halogen atom, cyano group, nitro group,

[1015] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1016] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1017] As a compound represented by the above general formula (3), the following compounds can be cited as specific examples.

[1018]

Chemical Formula 65

[1019]

[1020]

Chemical Formula 66

[1021]

[1022] [Chemical Formula 67]

[1023]

[1024]

Chemical Formula 68

[1025]

[1026]

Chemical Formula 69

[1027]

[1028] (The compound represented by general formula (4))

[1029] The compounds represented by general formula (4) will be described.

[1030] [Chemical Formula 70]

[1031]

[1032] (In the above general formula (4),

[1033] Z can be independently represented by CRa or nitrogen atoms.

[1034] Rings A1 and A2 are each independent of each other.

[1035] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or

[1036] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1037] When there are multiple Ra, one or more groups consisting of two or more adjacent Ra are selected.

[1038] They bond together to form substituted or unsubstituted monocyclic rings.

[1039] They bond together to form substituted or unsubstituted fused rings, or

[1040] They do not bond with each other.

[1041] n21 and n22 are each independently 0, 1, 2, 3 or 4.

[1042] When there are multiple Rb, one or more groups consisting of two or more adjacent Rb are considered.

[1043] They bond together to form substituted or unsubstituted monocyclic rings.

[1044] They bond together to form substituted or unsubstituted fused rings, or

[1045] They do not bond with each other.

[1046] When there are multiple Rc, one or more groups are formed by two or more adjacent Rc.

[1047] They bond together to form substituted or unsubstituted monocyclic rings.

[1048] They bond together to form substituted or unsubstituted fused rings, or

[1049] They do not bond with each other.

[1050] Ra, Rb, and Rc, which do not form the aforementioned single rings and do not form the aforementioned fused rings, are each independently...

[1051] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1052] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1053] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1054] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1055] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1056] -O-(R 904 The groups shown in the figure,

[1057] -S-(R 905 The groups shown in the figure,

[1058] -N(R 906 (R) 907 The groups shown in the figure,

[1059] Halogen atoms,

[1060] cyano,

[1061] Nitro,

[1062] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1063] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1064] The "aromatic hydrocarbon rings" of the A1 and A2 rings have the same structure as compounds formed by introducing hydrogen atoms into the aforementioned "aryl" group.

[1065] The "aromatic hydrocarbon rings" of A1 and A2 rings contain two carbon atoms on the fused 2-ring structure in the center of the above general formula (4) as cyclic atoms.

[1066] As a specific example of "a cyclic aromatic hydrocarbon ring with 6 to 50 carbon atoms, whether substituted or unsubstituted", compounds formed by introducing hydrogen atoms into the "aryl" group described in Specific Example Group G1 can be cited.

[1067] The "heterocyclic" rings A1 and A2 have the same structure as compounds formed by introducing hydrogen atoms into the aforementioned "heterocyclic group".

[1068] The "heterocyclic" rings A1 and A2 contain two carbon atoms from the fused 2-ring structure in the center of the above general formula (4) as cyclic atoms.

[1069] As a specific example of "a heterocycle with 5 to 50 cyclic atoms, whether substituted or unsubstituted", one can cite compounds formed by introducing hydrogen atoms into the "heterocyclic group" described in Specific Example Group G2.

[1070] Rb is bonded to any of the carbon atoms that form an aromatic hydrocarbon ring as an Al ring, or to any of the atoms that form a heterocycle as an Al ring.

[1071] Rc is bonded to any one of the carbon atoms that form an aromatic hydrocarbon ring as an A2 ring, or to any one of the atoms that form a heterocycle as an A2 ring.

[1072] Among Ra, Rb and Rc, at least one is preferably a group represented by the following general formula (4a), and more preferably at least two are groups represented by the following general formula (4a).

[1073]

Chemical Formula 71

[1074] *-L 401 -Ar 401 (4a)

[1075] (In the above general formula (4a),

[1076] L 401 for

[1077] single bond,

[1078] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or

[1079] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.

[1080] Ar 401 for

[1081] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms

[1082] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or

[1083] The group represented by the following general formula (4b).

[1084]

Chemical Formula 72

[1085]

[1086] (In the above general formula (4b),

[1087] L 402 and L 403 Each independently

[1088] single bond,

[1089] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or

[1090] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.

[1091] Ar 402 and Ar 403 The group formed

[1092] They bond together to form substituted or unsubstituted monocyclic rings.

[1093] They bond together to form substituted or unsubstituted fused rings, or

[1094] They do not bond with each other.

[1095] Ar does not form the aforementioned single ring and does not form the aforementioned fused ring 402 and Ar 403 Each independently

[1096] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1097] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1098] In one embodiment, the compound represented by the above general formula (4) is represented by the following general formula (42).

[1099]

Chemical Formula 73

[1100]

[1101] (In the above general formula (42),

[1102] R 401 ~R 411 One or more of the groups consisting of two or more adjacent elements.

[1103] They bond together to form substituted or unsubstituted monocyclic rings.

[1104] They bond together to form substituted or unsubstituted fused rings, or

[1105] They do not bond with each other.

[1106] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 401 ~R 411 Each independently

[1107] hydrogen atom,

[1108] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1109] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1110] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1111] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1112] -Si(R 901 (R902)(R) 903 The groups shown in the figure,

[1113] -O-(R 904 The groups shown in the figure,

[1114] -S-(R 905 The groups shown in the figure,

[1115] -N(R 906 (R) 907 The groups shown in the figure,

[1116] Halogen atoms,

[1117] cyano,

[1118] Nitro,

[1119] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1120] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1121] R 401 ~R 411 Preferably, at least one of them is a group represented by the above general formula (4a), and more preferably at least two of them are groups represented by the above general formula (4a).

[1122] R 404 and R 411 Preferably, it is a group represented by the above general formula (4a).

[1123] In one embodiment, the compound represented by the above general formula (4) is a compound formed by bonding the structure represented by the following general formula (4-1) or general formula (4-2) onto the A1 ring.

[1124] Additionally, in one embodiment, the compound represented by the above general formula (42) is in R 404 ~R 407 Compounds formed by bonding the following general formula (4-1) or general formula (4-2) to the bonded ring.

[1125] [Chemical Formula 74]

[1126]

[1127] In the above general formula (4-1), each of the two * is independently bonded to the cyclic carbon atom of the aromatic hydrocarbon ring or the cyclic atom of the heterocycle in the above general formula (4), or to the R in the above general formula (42). 404 ~R 407 Any one of the bonds in,

[1128] The three asterisks in the above general formula (4-2) are each independently bonded to the cyclic carbon atom of the aromatic hydrocarbon ring or the cyclic atom of the heterocycle in the above general formula (4), or to the R in the above general formula (42). 404 ~R 407 Any one of the bonds in,

[1129] R 421 ~R 427 One or more of the groups consisting of two or more adjacent elements.

[1130] They bond together to form substituted or unsubstituted monocyclic rings.

[1131] They bond together to form substituted or unsubstituted fused rings, or

[1132] They do not bond with each other.

[1133] R 431 ~R 438 One or more of the groups consisting of two or more adjacent elements.

[1134] They bond together to form substituted or unsubstituted monocyclic rings.

[1135] They bond together to form substituted or unsubstituted fused rings, or

[1136] They do not bond with each other.

[1137] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 421 ~R 427 and R 431 ~R438 Each independently

[1138] hydrogen atom,

[1139] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1140] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1141] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1142] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1143] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1144] -O-(R 904 The groups shown in the figure,

[1145] -S-(R 905 The groups shown in the figure,

[1146] -N(R 906 (R) 907 The groups shown in the figure,

[1147] Halogen atoms,

[1148] cyano,

[1149] Nitro,

[1150] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1151] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1152] In one embodiment, the compound represented by the above general formula (4) is a compound represented by the following general formula (41-3), general formula (41-4) or general formula (41-5).

[1153] [Chemical Formula 75]

[1154]

[1155] [Chemical Formula 76]

[1156]

[1157]

Chemical Formula 77

[1158]

[1159] (In the above general formulas (41-3), (41-4), and (41-5),

[1160] Ring A1 is defined in the same way as in general formula (4) above.

[1161] R 421 ~R 427 Each independently relates to R in the above general formula (4-1) 421 ~R 427 Same meaning

[1162] R 440 ~R 448 Each independently relates to R in the above general formula (42) 401 ~R 411 The meaning is the same.

[1163] In one embodiment, the aromatic hydrocarbon ring of the above general formula (41-5) with 6 to 50 carbon atoms, either substituted or unsubstituted for the A1 ring, is...

[1164] Substituted or unsubstituted naphthalene ring, or

[1165] Substituted or unsubstituted fluorene ring.

[1166] In one embodiment, the heterocycle of the above general formula (41-5), which has 5 to 50 cyclic atoms and is either substituted or unsubstituted for the A1 ring, is...

[1167] Substituted or unsubstituted dibenzofuran rings,

[1168] Substituted or unsubstituted carbazole ring, or

[1169] Substituted or unsubstituted dibenzothiophene ring.

[1170] In one embodiment, the compound represented by the above general formula (4) or the above general formula (42) is selected from the group consisting of the compounds represented by the following general formulas (461) to (467).

[1171] [Chemical Formula 78]

[1172]

[1173] [Chemical Formula 79]

[1174]

[1175] [Chemical Formula 80]

[1176]

[1177]

Chemical Formula 81

[1178]

[1179]

Chemical Formula 82

[1180]

[1181] (In the above general formulas (461), (462), (463), (464), (465), (466), and (467),

[1182] R 421 ~R 427 Each independently relates to R in the above general formula (4-1) 421 ~R 427 Same meaning

[1183] R 431 ~R 438 Each independently relates to R in the above general formula (4-2) 431 ~R 438 Same meaning

[1184] R 440 ~R 448 and R 451 ~R 454 Each independently relates to R in the above general formula (42) 401 ~R 411 Same meaning

[1185] X4 represents an oxygen atom, NR 801 or C(R) 802 (R) 803 ),

[1186] R 801 R 802 and R 803 Each independently

[1187] hydrogen atom,

[1188] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1189] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1190] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1191] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1192] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or

[1193] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.

[1194] In R801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[1195] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.

[1196] In R 803 In the case of multiple Rs, multiple Rs 803 (They may be the same or different.)

[1197] In one embodiment, for the compound represented by the above general formula (42), R 401 ~R 411 The compounds in this embodiment are described in detail as compounds represented by the following general formula (45), in which two or more adjacent groups are bonded to each other to form substituted or unsubstituted monocyclic rings or substituted or unsubstituted fused rings.

[1198] (The compound represented by general formula (45))

[1199] The compounds represented by general formula (45) will be described.

[1200]

Chemical Formula 83

[1201]

[1202] (In the above general formula (45),

[1203] Choose freely R 461 With R4 62 The group formed, R 462 With R 463 The group formed, R 464 With R 465 The group formed, R 465 With R 466 The group formed, R 466 With R 467 The group formed, R 468 With R 469 The group formed, R 469 With R 470 The groups formed and R 470 With R 471 Within a larger group, two or more groups are bonded together to form substituted or unsubstituted monocyclic rings or substituted or unsubstituted fused rings.

[1204] in,

[1205] R 461 With R 462The groups formed and R 462 With R 463 The groups do not simultaneously form a ring;

[1206] R 464 With R 465 The groups formed and R 465 With R 466 The groups do not simultaneously form a ring;

[1207] R 465 With R 466 The groups formed and R 466 With R 467 The groups do not simultaneously form a ring;

[1208] R 468 With R 469 The groups formed and R 469 With R 470 The groups do not simultaneously form a ring; and

[1209] R 469 With R 470 The groups formed and R 470 With R 471 The groups formed do not simultaneously form a ring.

[1210] R 461 ~R 471 Two or more rings are formed that are identical or different from each other.

[1211] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 461 ~R 471 Each independently

[1212] hydrogen atom,

[1213] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1214] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1215] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1216] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1217] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1218] -O-(R 904 The groups shown in the figure,

[1219] -S-(R 905 ), -N(R906 (R) 907 The groups shown in the figure,

[1220] Halogen atoms,

[1221] cyano,

[1222] Nitro,

[1223] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1224] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1225] In the above general formula (45), R n With R n+1 (n represents an integer selected from 461, 462, 464-466 and 468-470) mutually bonded with R n and R n+1 The two bonded cyclic carbon atoms together form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring. The ring is preferably composed of atoms selected from carbon, oxygen, sulfur and nitrogen, and the number of atoms in the ring is preferably 3 to 7, more preferably 5 or 6.

[1226] The compound represented by the above general formula (45) may have, for example, two, three, or four ring structures. Two or more ring structures may each reside on the same benzene ring in the parent skeleton of the above general formula (45), or they may reside on different benzene rings. For example, in the case of three ring structures, one ring structure may reside on each of the three benzene rings in the above general formula (45).

[1227] Examples of the ring structures in the compounds represented by the general formula (45) above include those represented by the general formulas (451) to (460).

[1228]

Chemical Formula 84

[1229]

[1230] (In the above general formulas (451) to (457),

[1231] *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14 represent R respectively. n and Rn +1 The two cyclic carbon atoms bonded above,

[1232] The cyclic carbon atoms bonded to Rn can be any one of the two cyclic carbon atoms represented by *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14.

[1233] X 45 For C(R) 4512 (R) 4513 ), NR 4514 oxygen or sulfur atoms

[1234] R 4501 ~R 4506 and R 4512 ~R 4513 One or more of the groups consisting of two or more adjacent elements.

[1235] They bond together to form substituted or unsubstituted monocyclic rings.

[1236] They bond together to form substituted or unsubstituted fused rings, or

[1237] They do not bond with each other.

[1238] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 4501 ~R 4514 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.

[1239]

Chemical Formula 85

[1240]

[1241] (In the above general formulas (458) to (460),

[1242] *1 and *2, and *3 and *4 respectively represent R n and R n+1 The two cyclic carbon atoms bonded above,

[1243] R n The bonded cyclic carbon atoms can be any one of the two cyclic carbon atoms represented by *1 and *2 or *3 and *4.

[1244] X 45 For C(R) 4512 (R) 4513 ), NR 4514 oxygen or sulfur atoms

[1245] R 4512 ~R 4513 and R 4515 ~R 4525One or more of the groups consisting of two or more adjacent elements.

[1246] They bond together to form substituted or unsubstituted monocyclic rings.

[1247] They bond together to form substituted or unsubstituted fused rings, or

[1248] They do not bond with each other.

[1249] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 4512 ~R 4513 R 4515 ~R 4521 and R 4522 ~R 4525 and R 4514 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.

[1250] In the above general formula (45), R is preferred. 462 R 464 R 465 R 470 and R 471 At least one of them (preferably R) 462 R 465 and R 470 At least one of them, further preferred R 462 () are groups that do not form ring structures.

[1251] (i) In the above general formula (45), R n With R n+1 When the formed ring structure has substituents, the substituents,

[1252] (ii) R in the above general formula (45) that does not form a ring structure 461 ~R 471 as well as

[1253] (iii) R in equations (451) to (460) 4501 ~R 4514 R 4515 ~R 4525 Each is preferred to be independent of the other.

[1254] hydrogen atom,

[1255] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1256] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1257] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1258] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1259] -N(R 906 (R) 907 The groups shown in the figure,

[1260] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms

[1261] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or

[1262] Any group in the group consisting of the groups represented by the following general formulas (461) to (464).

[1263]

Chemical Formula 86

[1264]

[1265] (In the above general formulas (461) to (464),

[1266] R d Each independently

[1267] hydrogen atom,

[1268] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1269] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1270] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1271] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1272] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1273] -O-(R 904 The groups shown in the figure,

[1274] -S-(R 905 The groups shown in the figure,

[1275] -N(R 906 (R) 907 The groups shown in the figure,

[1276] Halogen atoms,

[1277] cyano,

[1278] Nitro,

[1279] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1280] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1281] X 46 For C(R) 801 (R) 802 ), NR 803 oxygen or sulfur atoms

[1282] R 801 R 802 and R 803 Each independently

[1283] hydrogen atom,

[1284] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1285] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1286] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1287] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1288] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or

[1289] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.

[1290] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[1291] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.

[1292] In R 803 In the case of multiple Rs, multiple Rs 803 They are the same or different.

[1293] p1 is 5.

[1294] p2 is 4.

[1295] p3 is 3.

[1296] p4 is 7.

[1297] In the above general formulas (461) to (464), each * independently represents a bonding position with the ring structure.

[1298] In the second compound, R901 ~R 907 Same as defined above.

[1299] In one embodiment, the compound represented by the above general formula (45) is represented by any one of the following general formulas (45-1) to (45-6).

[1300] [Chemical Formula 87]

[1301]

[1302]

Chemical Formula 88

[1303]

[1304] (In the above general formulas (45-1) to (45-6),

[1305] Each of the rings d to i is independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.

[1306] R 461 ~R 471 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.

[1307] In one embodiment, the compound represented by the above general formula (45) is represented by any one of the following general formulas (45-7) to (45-12).

[1308]

Chemical Formula 89

[1309]

[1310] [Chemical Formula 90]

[1311]

[1312] (In the above general formulas (45-7) to (45-12),

[1313] Rings d to f, k, and j are each independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.

[1314] R 461 ~R 471 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.

[1315] In one embodiment, the compound represented by the above general formula (45) is represented by any one of the following general formulas (45-13) to (45-21).

[1316]

Chemical Formula 91

[1317]

[1318]

Chemical Formula 92

[1319]

[1320] [Chemical Formula 93]

[1321]

[1322] (In the above general formulas (45-13) to (45-21),

[1323] Each of the rings d to k is independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.

[1324] R 461 ~R 471 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.

[1325] Substituents that further have substituents, such as those found in the above-mentioned ring g or ring h, can be exemplified by...

[1326] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1327] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms

[1328] The groups represented by the above general formula (461),

[1329] The groups represented by the above general formula (463), or

[1330] The group represented by the above general formula (464).

[1331] In one embodiment, the compound represented by the above general formula (45) is represented by any one of the following general formulas (45-22) to (45-25).

[1332] [Chemical Formula 94]

[1333]

[1334] (In the above general formulas (45-22) to (45-25),

[1335] X 46 and X 47 Each independently is C(R) 801 (R) 802 ), NR 803 oxygen or sulfur atoms

[1336] R 461 ~R 471 and R 481 ~R 488 Each independently relates to R in the above general formula (45) 461 ~R 471 They have the same meaning.

[1337] R 801 R 802 and R 803 Each independently

[1338] hydrogen atom,

[1339] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1340] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1341] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1342] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1343] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or

[1344] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.

[1345] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[1346] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.

[1347] In R 803 In the case of multiple Rs, multiple Rs 803 (They may be the same or different.)

[1348] In one embodiment, the compound represented by the above general formula (45) is represented by the following general formulas (45-26).

[1349] [Chemical Formula 95]

[1350]

[1351] (In the above general formula (45-26),

[1352] X 46 For C(R) 801 (R) 802 ), NR 803oxygen or sulfur atoms

[1353] R 463 R 464 R 467 R 468 R 471 and R 481 ~R 492 Each independently relates to R in the above general formula (45) 461 ~R 471 They have the same meaning.

[1354] R 801 R 802 and R 803 Each independently

[1355] hydrogen atom,

[1356] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1357] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1358] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1359] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1360] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or

[1361] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.

[1362] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[1363] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.

[1364] In R 803 In the case of multiple Rs, multiple Rs 803 (They may be the same or different.)

[1365] As a compound represented by the general formula (4) above, specific examples can be given as the following compounds. In the following specific examples, Ph represents a phenyl group and D represents a deuterium atom.

[1366]

Chemical Formula 96

[1367]

[1368] [Chemical Formula 97]

[1369]

[1370] [Chemical Formula 98]

[1371]

[1372]

Chemical Formula 99

[1373]

[1374]

Chemical Formula 100

[1375]

[1376]

Chemical Formula 101

[1377]

[1378]

Chemical Formula 102

[1379]

[1380]

Chemical Formula 103

[1381]

[1382] [Chemical Formula 104]

[1383]

[1384] [Chemical Formula 105]

[1385]

[1386] (The compound represented by general formula (5))

[1387] The compounds represented by general formula (5) will be described. The compounds represented by general formula (5) are the compounds corresponding to the compounds represented by general formula (41-3) above.

[1388] [Chemical Formula 106]

[1389]

[1390] (In the above general formula (5),

[1391] R 501 ~R 507 and R 511 ~R 517 One or more of the groups consisting of two or more adjacent elements.

[1392] They bond together to form substituted or unsubstituted monocyclic rings.

[1393] They bond together to form substituted or unsubstituted fused rings, or

[1394] They do not bond with each other.

[1395] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 501 ~R 507 and R 511 ~R 517 Each independently

[1396] hydrogen atom,

[1397] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1398] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1399] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1400] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1401] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1402] -O-(R 904 The groups shown in the figure,

[1403] -S-(R 905 The groups shown in the figure,

[1404] -N(R 906 (R) 907 The groups shown in the figure,

[1405] Halogen atoms,

[1406] cyano,

[1407] Nitro,

[1408] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1409] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[1410] R 521 and R 522 Each independently

[1411] hydrogen atom,

[1412] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1413] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1414] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1415] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1416] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1417] -O-(R 904 The groups shown in the figure,

[1418] -S-(R 905 The groups shown in the figure,

[1419] -N(R 906 (R) 907 The groups shown in the figure,

[1420] Halogen atoms,

[1421] cyano,

[1422] Nitro,

[1423] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1424] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1425] “R 501 ~R 507 and R 511 ~R 517 "One of the groups consisting of two or more adjacent elements" is, for example, R. 501 With R 502 The group formed, R 502 With R 503 The group formed, R 503 With R 504 The group formed, R 505 With R 506 The group formed, R 506 With R 507 The group formed, R 501 With R 502 With R 503 The groups and combinations formed by them.

[1426] In one implementation, R 501 ~R 507 and R 511 ~R 517 At least one, preferably two, of them are -N(R) 906 (R) 907 The group shown is ).

[1427] In one implementation, R 501 ~R 507 and R 511 ~R 517 Each independently

[1428] hydrogen atom,

[1429] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1430] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[1431] In one embodiment, the compound represented by the above general formula (5) is the compound represented by the following general formula (52).

[1432] [Chemical Formula 107]

[1433]

[1434] (In the above general formula (52),

[1435] R 531 ~R 534 and R 541 ~R 544 One or more of the groups consisting of two or more adjacent elements.

[1436] They bond together to form substituted or unsubstituted monocyclic rings.

[1437] They bond together to form substituted or unsubstituted fused rings, or

[1438] They do not bond with each other.

[1439] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 531 ~R 534 R 541 ~R 544 and R 551 and R 552 Each independently

[1440] hydrogen atom,

[1441] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1442] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1443] R 561 ~R 564 Each independently

[1444] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1445] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1446] In one embodiment, the compound represented by the above general formula (5) is the compound represented by the following general formula (53).

[1447] [Chemical Formula 108]

[1448]

[1449] (In the above general formula (53), R) 551 R 552 and R 561 ~R 564 Each independently relates to R in the above general formula (52) 551 R 552 and R 561 ~R 564 The meaning is the same.

[1450] In one implementation, R in the above general formulas (52) and (53) 561 ~R 564 Each is independently a substituted or unsubstituted aryl group (preferably phenyl) with 6 to 50 carbon atoms in a cyclic structure.

[1451] In one implementation, R in the above general formula (5) 521 and R 522 R in the above general formulas (52) and (53) 551 and R 552 It is a hydrogen atom.

[1452] In one embodiment, the substituents expressed as "substituted or unsubstituted" in the above general formulas (5), (52), and (53) are...

[1453] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1454] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1455] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1456] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1457] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1458] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[1459] As a compound represented by the above general formula (5), the following compounds can be cited as specific examples.

[1460] [Chemical Formula 109]

[1461]

[1462]

Chemical Formula 110

[1463]

[1464]

Chemical Formula 111

[1465]

[1466]

Chemical Formula 112

[1467]

[1468]

Chemical Formula 113

[1469]

[1470]

Chemical Formula 114

[1471]

[1472]

Chemical Formula 115

[1473]

[1474]

Chemical Formula 116

[1475]

[1476]

Chemical Formula 117

[1477]

[1478]

Chemical Formula 118

[1479]

[1480]

Chemical Formula 119

[1481]

[1482]

Chemical Formula 120

[1483]

[1484]

Chemical Formula 121

[1485]

[1486]

Chemical Formula 122

[1487]

[1488]

Chemical Formula 123

[1489]

[1490] [Chemical Formula 124]

[1491]

[1492] [Chemical Formula 125]

[1493]

[1494] (The compound represented by general formula (6))

[1495] The compounds represented by general formula (6) will be described.

[1496] [Chemical Formula 126]

[1497]

[1498] (In the above general formula (6),)

[1499] Rings a, b, and c are each independently...

[1500] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or

[1501] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1502] R 601 and R 602 Each ring independently bonds to the aforementioned a-ring, b-ring, or c-ring to form a substituted or unsubstituted heterocycle, or not to form a substituted or unsubstituted heterocycle.

[1503] R does not form the aforementioned substituted or unsubstituted heterocycles 601 and R 602 Each independently

[1504] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1505] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1506] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1507] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1508] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1509] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1510] Rings a, b, and c are rings fused with the central fused 2-ring structure of the above general formula (6) consisting of boron atoms and two nitrogen atoms (substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 cyclic carbon atoms, or substituted or unsubstituted heterocycles with 5 to 50 cyclic atoms).

[1511] The "aromatic hydrocarbon rings" of rings a, b, and c have the same structure as compounds formed by introducing hydrogen atoms into the aforementioned "aryl" group.

[1512] The "aromatic hydrocarbon ring" of ring a contains three carbon atoms on the fused 2-ring structure in the center of the above general formula (6) as cyclic atoms.

[1513] The "aromatic hydrocarbon rings" of rings b and c contain two carbon atoms on the fused 2-ring structure in the center of the above general formula (6) as cyclic atoms.

[1514] As a specific example of "a cyclic aromatic hydrocarbon ring with 6 to 50 carbon atoms, whether substituted or unsubstituted", compounds formed by introducing hydrogen atoms into the "aryl" group described in Specific Example Group G1 can be cited.

[1515] The "heterocyclic" rings a, b, and c have the same structure as compounds formed by introducing hydrogen atoms into the aforementioned "heterocyclic groups".

[1516] The "heterocyclic ring" of ring a includes three carbon atoms in the fused 2-ring structure at the center of the above general formula (6) as cyclic atoms. The "heterocyclic rings" of rings b and c include two carbon atoms in the fused 2-ring structure at the center of the above general formula (6) as cyclic atoms. As a specific example of "heterocyclic rings with 5 to 50 substituted or unsubstituted cyclic atoms", compounds formed by introducing hydrogen atoms into the "heterocyclic group" described in specific example group G2 can be cited.

[1517] R 601 and R 602 Each ring can independently bond with ring a, ring b, or ring c to form substituted or unsubstituted heterocycles. In this case, the heterocycle contains the nitrogen atom in the fused 2-ring structure at the center of the general formula (6). The heterocycle may also contain heteroatoms other than the nitrogen atom. R 601 and R 602 Specifically, bonding with ring a, ring b, or ring c refers to the bonding between atoms constituting ring a, ring b, or ring c and atoms constituting ring R. 601 and R 602 The atoms are bonded together. For example, it could also be R. 601 fused with α ring to form R 601A nitrogen-containing heterocycle in which two rings (or three or more rings) are fused to the a ring. Specific examples of such nitrogen-containing heterocycles include compounds corresponding to the heterocyclic groups in Specific Example Group G2 that contain nitrogen and are fused to two or more rings.

[1518] R 601 Cases involving b-ring bonding, R 602 The case of α-ring bonding and R 602 The situation regarding bonding with the c-ring is the same as described above.

[1519] In one embodiment, ring a, ring b, and ring c in the above general formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring with 6 to 50 carbon atoms.

[1520] In one embodiment, ring a, ring b, and ring c in the above general formula (6) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.

[1521] In one implementation, R in the above general formula (6) 601 and R 602 Each independently

[1522] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1523] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1524] Preferably, it is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[1525] In one embodiment, the compound represented by the above general formula (6) is the compound represented by the following general formula (62).

[1526]

Chemical Formula 127

[1527]

[1528] (In the above general formula (62),

[1529] R 601A With selection from R 611 and R 621 One or more of them are bonded together to form a substituted or unsubstituted heterocycle, or they do not form a substituted or unsubstituted heterocycle.

[1530] R 602A With selection from R 613 and R 614 One or more of them are bonded together to form a substituted or unsubstituted heterocycle, or they do not form a substituted or unsubstituted heterocycle.

[1531] R does not form the aforementioned substituted or unsubstituted heterocycles 601A and R602A Each independently

[1532] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1533] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1534] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1535] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1536] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1537] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1538] R 611 ~R 621 One or more of the groups consisting of two or more adjacent elements.

[1539] They bond together to form substituted or unsubstituted monocyclic rings.

[1540] They bond together to form substituted or unsubstituted fused rings, or

[1541] They do not bond with each other.

[1542] R does not form the aforementioned substituted or unsubstituted heterocycles, does not form the aforementioned monocyclic rings, and does not form the aforementioned fused rings. 611 ~R 621 Each independently

[1543] hydrogen atom,

[1544] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1545] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1546] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1547] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1548] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1549] -O-(R 904 The groups shown in the figure,

[1550] -S-(R 905 The groups shown in the figure,

[1551] -N(R906 (R) 907 The groups shown in the figure,

[1552] Halogen atoms,

[1553] cyano,

[1554] Nitro,

[1555] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1556] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1557] R in the above general formula (62) 601A and R 602A R, respectively, is the same as the general formula (6) above. 601 and R 602 The corresponding functional group.

[1558] For example, R 601A With R 611 These are nitrogen-containing heterocycles that are bonded together to form a fused two-ring (or three-ring or more) fused ring, comprising the rings containing the rings and a benzene ring corresponding to the α-ring. Specific examples of such nitrogen-containing heterocycles include compounds corresponding to the nitrogen-containing fused heterocyclic groups in Specific Example Group G2. R 601A With R 621 Bonding situation, R 602A With R 613 Bonding conditions and R 602A With R 614 The bonding situation is the same as above.

[1559] R 611 ~R 621 One or more of the two or more adjacent groups can

[1560] They bond together to form substituted or unsubstituted monocyclic rings, or

[1561] They bond together to form substituted or unsubstituted fused rings.

[1562] For example, R 611 With R 612 The bonds can be combined to form structures consisting of six-membered rings such as benzene rings, indole rings, pyrrole rings, benzofuran rings, or benzothiophene rings. The resulting fused rings can be naphthalene rings, carbazole rings, indole rings, dibenzofuran rings, or dibenzothiophene rings.

[1563] In one implementation, R does not participate in forming the ring. 611 ~R 621 Each independently

[1564] hydrogen atom,

[1565] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1566] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1567] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[1568] In one implementation, R does not participate in forming the ring. 611 ~R 621 Each independently

[1569] hydrogen atom,

[1570] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1571] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[1572] In one implementation, R does not participate in forming the ring. 611 ~R 621 Each independently

[1573] hydrogen atom, or

[1574] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted.

[1575] In one implementation, R does not participate in forming the ring. 611 ~R 621 Each independently

[1576] hydrogen atom, or

[1577] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[1578] R 611 ~R 621 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1579] In one embodiment, the compound represented by the above general formula (62) is the compound represented by the following general formula (63).

[1580] [Chemical Formula 128]

[1581]

[1582] (In the above general formula (63),

[1583] R 631 With R 646 Bonding to form substituted or unsubstituted heterocycles, or not forming substituted or unsubstituted heterocycles.

[1584] R 633 With R 647 Bonding to form substituted or unsubstituted heterocycles, or not forming substituted or unsubstituted heterocycles.

[1585] R 634 With R 651 Bonding to form substituted or unsubstituted heterocycles, or not forming substituted or unsubstituted heterocycles.

[1586] R 641 With R 642 Bonding to form substituted or unsubstituted heterocycles, or not forming substituted or unsubstituted heterocycles.

[1587] R 631 ~R 651 One or more of the groups consisting of two or more adjacent elements.

[1588] They bond together to form substituted or unsubstituted monocyclic rings.

[1589] They bond together to form substituted or unsubstituted fused rings, or

[1590] They do not bond with each other.

[1591] R does not form the aforementioned substituted or unsubstituted heterocycles, does not form the aforementioned monocyclic rings, and does not form the aforementioned fused rings. 631 ~R 651 Each independently

[1592] hydrogen atom,

[1593] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1594] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1595] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1596] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1597] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1598] -O-(R 904 The groups shown in the figure,

[1599] -S-(R 905 The groups shown in the figure,

[1600] -N(R 906 (R) 907 The groups shown in the figure,

[1601] Halogen atoms,

[1602] cyano,

[1603] Nitro,

[1604] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1605] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1606] R 631 Can be used with R 646 Bonding forms substituted or unsubstituted heterocycles. For example, R can be... 631 With R 646 Bonding to form fused R 646 The bonded benzene ring, or a nitrogen-containing heterocycle consisting of three or more rings fused together with a nitrogen-containing ring and a benzene ring corresponding to the a ring. Specific examples of such nitrogen-containing heterocycles include compounds corresponding to the nitrogen-containing heterocyclic groups fused together in Specific Example Group G2. R 633 With R 647 Bonding situation, R 634 With R 651 Bonding conditions and R 641 With R 642 The bonding situation is the same as above.

[1607] In one implementation, R does not participate in forming the ring. 631 ~R 651 Each independently

[1608] hydrogen atom,

[1609] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1610] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1611] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[1612] In one implementation, R does not participate in forming the ring. 631 ~R 651 Each independently

[1613] hydrogen atom,

[1614] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1615] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[1616] In one implementation, R does not participate in forming the ring. 631 ~R651 Each independently

[1617] hydrogen atom, or

[1618] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted.

[1619] In one implementation, R does not participate in forming the ring. 631 ~R 651 Each independently

[1620] hydrogen atom, or

[1621] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[1622] R 631 ~R 651 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1623] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63A).

[1624] [Chemical Formula 129]

[1625]

[1626] (In the above general formula (63A),

[1627] R 661 for

[1628] hydrogen atom,

[1629] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1630] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1631] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1632] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or

[1633] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.

[1634] R 662 ~R 665 Each independently

[1635] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1636] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1637] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1638] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or

[1639] (Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure.)

[1640] In one implementation, R 661 ~R 665 Each independently

[1641] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or

[1642] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.

[1643] In one implementation, R 661 ~R 665 Each is an alkyl group, either substituted or unsubstituted, having 1 to 50 carbon atoms.

[1644] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63B).

[1645]

Chemical Formula 130

[1646]

[1647] (In the above general formula (63B),

[1648] R 671 and R 672 Each independently

[1649] hydrogen atom,

[1650] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1651] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1652] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1653] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1654] -N(R 906 (R) 907 The group shown in the figure, or

[1655] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.

[1656] R 673 ~R 675 Each independently

[1657] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1658] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1659] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1660] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1661] -N(R 906 (R) 907 The group shown in the figure, or

[1662] (Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure.)

[1663] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63B').

[1664]

Chemical Formula 131

[1665]

[1666] (In the above general formula (63B'), R) 672 ~R 675 Each independently relates to R in the above general formula (63B) 672 ~R 675 The meaning is the same.

[1667] In one implementation, R 671 ~R 675 At least one of them is

[1668] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1669] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1670] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1671] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1672] -N(R 906 (R) 907 The group shown in the figure, or

[1673] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.

[1674] In one implementation method

[1675] R 672 for

[1676] hydrogen atom,

[1677] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1678] -N(R 906 (R) 907 The group shown in the figure, or

[1679] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.

[1680] R 671 and R 673 ~R 675 Each independently

[1681] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1682] -N(R 906 (R) 907 The group shown in the figure, or

[1683] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.

[1684] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63C).

[1685]

Chemical Formula 132

[1686]

[1687] (In the above general formula (63C),

[1688] R 681 and R 682 Each independently

[1689] hydrogen atom,

[1690] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1691] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1692] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1693] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or

[1694] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.

[1695] R 683 ~R 686 Each independently

[1696] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1697] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1698] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1699] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or

[1700] (Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure.)

[1701] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63C').

[1702]

Chemical Formula 133

[1703]

[1704] (In the above general formula (63C'), R) 683 ~R 686 Each independently relates to R in the above general formula (63C). 683 ~R 686 The meaning is the same.

[1705] In one implementation, R 681 ~R 686 Each independently

[1706] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or

[1707] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.

[1708] In one implementation, R 681 ~R 686 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure.

[1709] For the compound shown in the general formula (6) above, the a ring, b ring and c ring can first be connected by a linking group (containing NR). 601 Groups and containing NR 602 The intermediate is produced by bonding the boron rings (a, b, and c) with a linking group (a group containing boron atoms). The final product is then produced by bonding the a, b, and c rings together with a linking group (a group containing boron atoms). Amination reactions such as the Buchwald-Hartwig reaction can be used in the first reaction. The tandem hetero Friedel-Crafts reaction can be used in the second reaction.

[1710] Although specific examples of compounds represented by the above general formula (6) are described below, these are merely examples, and the compounds represented by the above general formula (6) are not limited to the specific examples described below.

[1711]

Chemical Formula 134

[1712]

[1713] [Chemical Formula 135]

[1714]

[1715]

Chemical Formula 136

[1716]

[1717]

Chemical Formula 137

[1718]

[1719]

Chemical Formula 138

[1720]

[1721]

Chemical Formula 139

[1722]

[1723] [Chemical Formula 140]

[1724]

[1725]

Chemical Formula 141

[1726]

[1727] [Chemical Formula 142]

[1728]

[1729] [Chemical Formula 143]

[1730]

[1731] [Chemical Formula 144]

[1732]

[1733] [Chemical Formula 145]

[1734]

[1735] (The compound represented by general formula (7))

[1736] The compounds represented by general formula (7) will be described.

[1737] [Chemical Formula 146]

[1738]

[1739] [Chemical Formula 147]

[1740]

[1741] (In the above general formula (7),

[1742] The r-ring is a ring shown in the above general formula (72) or general formula (73) that is fused at any position of adjacent rings.

[1743] The q-ring and s-ring are each independently rings fused at any position of adjacent rings as shown in the above general formula (74).

[1744] The p-ring and t-ring are each independently structures shown in the above general formula (75) or general formula (76) that are fused at any position of adjacent rings.

[1745] X7 represents an oxygen atom, a sulfur atom, or NR. 702 .

[1746] In R 701 In the case of multiple occurrences, multiple adjacent R 701

[1747] They bond together to form substituted or unsubstituted monocyclic rings.

[1748] They bond together to form substituted or unsubstituted fused rings, or

[1749] They do not bond with each other.

[1750] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 701 and R 702 Each independently

[1751] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1752] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1753] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1754] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1755] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1756] -O-(R 904 The groups shown in the figure,

[1757] -S-(R 905 The groups shown in the figure,

[1758] -N(R 906 (R) 907 The groups shown in the figure,

[1759] Halogen atoms,

[1760] cyano,

[1761] Nitro,

[1762] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1763] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1764] Ar 701 and Ar 702 Each independently

[1765] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1766] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1767] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1768] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1769] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1770] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1771] L 701 for

[1772] Substituted or unsubstituted alkylene groups having 1 to 50 carbon atoms

[1773] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1774] Substituted or unsubstituted ynylene groups with 2 to 50 carbon atoms

[1775] Substituted or unsubstituted cycloalkylene groups with 3 to 50 carbon atoms

[1776] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[1777] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1778] m1 is 0, 1, or 2.

[1779] m2 can be 0, 1, 2, 3, or 4.

[1780] m3 can be independently 0, 1, 2 or 3.

[1781] Each m4 is independently 0, 1, 2, 3, 4, or 5.

[1782] In R 701 In the case of multiple Rs, multiple Rs 701 They are the same or different.

[1783] When multiple X7s exist, they may be identical or different from each other.

[1784] In R 702 In the case of multiple Rs, multiple Rs 702 They are the same or different.

[1785] In Ar 701 In the case of multiple instances, multiple Ar 701 They are the same or different.

[1786] In Ar 702 In the case of multiple instances, multiple Ar 702 They are the same or different.

[1787] In L 701 In the case of multiple Ls, multiple Ls 701 (They may be the same or different.)

[1788] In the above general formula (7), each of the p-ring, q-ring, r-ring, s-ring, and t-ring is fused with its adjacent ring by two carbon atoms. The position and direction of fusion are not limited, and fusion can occur at any position and in any direction.

[1789] In one embodiment, in the above general formula (72) or general formula (73) which is an r-ring, m1 = 0 or m2 = 0.

[1790] In one embodiment, the compound represented by the above general formula (7) is represented by any one of the following general formulas (71-1) to (71-6).

[1791] [Chemical Formula 148]

[1792]

[1793] [Chemical Formula 149]

[1794]

[1795] [Chemical Formula 150]

[1796]

[1797]

Chemical Formula 151

[1798]

[1799]

Chemical Formula 152

[1800]

[1801]

Chemical Formula 153

[1802]

[1803] (In the above general formulas (71-1) to (71-6), R) 701 X7, Ar 701 Ar 702 L 701 m1 and m3 are respectively related to R in the above general formula (7). 701 X7, Ar 701 Ar 702 L 701 (m1 and m3 have the same meaning.)

[1804] In one embodiment, the compound represented by the above general formula (7) is represented by any one of the following general formulas (71-11) to (71-13).

[1805] [Chemical Formula 154]

[1806]

[1807]

Chemical Formula 155

[1808]

[1809] [Chemical Formula 156]

[1810]

[1811] (In the above general formulas (71-11) to (71-13), R) 701 X7, Ar 701 Ar 702 L 701 m1, m3 and m4 are respectively related to R in the above general formula (7) 701 X7, Ar 701 Ar 702 L 701 m1, m3, and m4 have the same meaning.

[1812] In one embodiment, the compound represented by the above general formula (7) is represented by any one of the following general formulas (71-21) to (71-25).

[1813]

Chemical Formula 157

[1814]

[1815]

Chemical Formula 158

[1816]

[1817] [Chemical Formula 159]

[1818]

[1819] [Chemical Formula 160]

[1820]

[1821]

Chemical Formula 161

[1822]

[1823] (In the above general formulas (71-21) to (71-25), R) 701 X7, Ar 701 Ar 702 L 701 m1 and m4 are respectively related to R in the above general formula (7). 701 X7, Ar 701 Ar 702 L 701 (m1 and m4 have the same meaning.)

[1824] In one embodiment, the compound represented by the above general formula (7) is represented by any one of the following general formulas (71-31) to (71-33).

[1825]

Chemical Formula 162

[1826]

[1827] [Chemical Formula 163]

[1828]

[1829] [Chemical Formula 164]

[1830]

[1831] (In the above general formulas (71-31) to (71-33), R) 701 X7, Ar 701 Ar 702 L 701 m2 to m4 are respectively related to R in the above general formula (7). 701 X7, Ar 701 Ar702 L 701 (m2 to m4 have the same meaning.)

[1832] In one implementation, Ar 701 and Ar 702 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure.

[1833] In one implementation, Ar 701 and Ar 702 One of them is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic ring, Ar 701 and Ar 702 The other one is a heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[1834] As a compound represented by the above general formula (7), the following compounds can be cited as specific examples.

[1835] [Chemical Formula 165]

[1836]

[1837]

Chemical Formula 166

[1838]

[1839] [Chemical Formula 167]

[1840]

[1841] [Chemical Formula 168]

[1842]

[1843] [Chemical Formula 169]

[1844]

[1845] [Chemical Formula 170]

[1846]

[1847] (The compound represented by general formula (8))

[1848] The compounds represented by general formula (8) will be described.

[1849]

Chemical Formula 171

[1850]

[1851] (In the above general formula (8),

[1852] R801 With R 802 R 802 With R 803 and R 803 With R 804 At least one group of the groups are bonded to each other to form the divalent groups shown in the following general formula (82), or they are not bonded to each other.

[1853] R 805 With R 806 R 806 With R 807 and R 807 With R 808 At least one group of the radicals may bond together to form a divalent group as shown in the general formula (83) below, or they may not bond together.

[1854] [Chemical Formula 172]

[1855]

[1856] (R that does not form the divalent group shown in the above general formula (82)) 801 ~R 804 and R 811 ~R 814 At least one of them is a monovalent group represented by the following general formula (84),

[1857] R that does not form the divalent group shown in the above general formula (83) 805 ~R 808 and R 821 ~R 824 At least one of them is a monovalent group represented by the following general formula (84),

[1858] X8 is CR 81 R 82 oxygen atom, sulfur atom or NR 809 ,

[1859] By R 81 and R 82 Groups

[1860] They bond together to form substituted or unsubstituted monocyclic rings.

[1861] They bond together to form substituted or unsubstituted fused rings, or

[1862] They do not bond with each other.

[1863] R that does not form the divalent groups shown in general formulas (82) and (83) above, and does not form the monovalent groups shown in general formula (84) above. 801 ~R 808 R that is not a monovalent group as shown in the above general formula (84) 811~R 814 and R 821 ~R 824 R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 81 and R 82 and R 809 Each independently

[1864] hydrogen atom,

[1865] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1866] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1867] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1868] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1869] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1870] -O-(R 904 The groups shown in the figure,

[1871] -S-(R 905 The groups shown in the figure,

[1872] -N(R 906 (R) 907 The groups shown in the figure,

[1873] Halogen atoms,

[1874] cyano,

[1875] Nitro,

[1876] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1877] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1878]

Chemical Formula 173

[1879]

[1880] (In the above general formula (84),

[1881] Ar 801 and Ar 802 Each independently

[1882] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1883] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1884] L 801 ~L 803 Each independently

[1885] single bond,

[1886] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms

[1887] Substituted or unsubstituted divalent heterocyclic groups with 5 to 30 cyclic atoms, or

[1888] A divalent linker is formed by bonding 2 to 4 groups from the group consisting of a substituted or unsubstituted aryl group with 6 to 30 carbon atoms and a substituted or unsubstituted divalent heterocyclic group with 5 to 30 carbon atoms.

[1889] In the above general formula (84), * indicates the bonding position with the ring structure shown in general formula (8), or the group shown in general formula (82) or general formula (83).

[1890] R is also preferred 801 With R 802 R 802 With R 803 and R803 and R 804 At least one pair of mutual bonds and R 805 With R 806 R 806 With R 807 and R 807 With R 808 They do not bond with each other.

[1891] R is also preferred 801 With R 802 R 802 With R 803 and R803 and R 804 Non-bonded and R 805 With R 806 R 806 With R 807 and R 807 With R 808 At least one pair of bonds exists between them.

[1892] R is also preferred 801 With R 802 R 802 With R 803 and R803 and R 804 At least one group of R bonds to each other to form a divalent group as shown in the following general formula (82) and R 805 With R 806 R806 With R 807 and R 807 With R 808 At least one group of the groups are bonded together to form a divalent group as shown in the following general formula (83).

[1893] In the above general formula (8), the positions of the divalent groups shown in general formula (82) and general formula (83) are not particularly limited, and can be formed in R 801 ~R 808 The group can be formed at any of the possible positions.

[1894] In one embodiment, the compound represented by the above general formula (8) is represented by any one of the following general formulas (81A-1) to (81A-3).

[1895] [Chemical Formula 174]

[1896]

[1897] [Chemical Formula 175]

[1898]

[1899] (In the above general formulas (81A-1) to (81A-3),

[1900] X8 has the same meaning as X8 in the above general formula (8).

[1901] In the above general formula (81A-1), R 803 R 804 and R 811 ~R 814 At least one of them is a monovalent group as shown in the above general formula (84).

[1902] In the above general formula (81A-2), R 801 R 804 and R 811 ~R 814 At least one of them is a monovalent group represented by the above general formula (84).

[1903] In the above general formula (81A-3), R 801 R 802 and R 811 ~R 814 At least one of them is a monovalent group represented by the above general formula (84).

[1904] In the above general formulas (81A-1) to (81A-3), R 805 ~R 808 At least one of them is a monovalent group represented by the above general formula (84).

[1905] R is not a monovalent group as shown in the above general formula (84) 801 ~R 808 and R 811 ~R 814 Each independently

[1906] hydrogen atom,

[1907] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1908] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1909] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1910] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1911] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1912] -O-(R 904 The groups shown in the figure,

[1913] -S-(R 905 The groups shown in the figure,

[1914] -N(R 906 (R) 907 The groups shown in the figure,

[1915] Halogen atoms,

[1916] cyano,

[1917] Nitro,

[1918] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1919] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1920] In one embodiment, the compound represented by the above general formula (8) is represented by any one of the following general formulas (81-1) to (81-6).

[1921] [Chemical Formula 176]

[1922]

[1923]

Chemical Formula 177

[1924]

[1925] [Chemical Formula 178]

[1926]

[1927] (In the above general formulas (81-1) to (81-6),

[1928] X8 has the same meaning as X8 in the above general formula (8).

[1929] R 801 ~R 824 At least two of them are monovalent groups as shown in the above general formula (84).

[1930] R is not a monovalent group as shown in the above general formula (84) 801 ~R 824 Each independently

[1931] hydrogen atom,

[1932] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1933] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1934] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1935] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1936] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1937] -O-(R 904 The groups shown in the figure,

[1938] -S-(R 905 The groups shown in the figure,

[1939] -N(R 906 (R) 907 The groups shown in the figure,

[1940] Halogen atoms,

[1941] cyano,

[1942] Nitro,

[1943] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1944] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1945] In one embodiment, the compound represented by the above general formula (8) is represented by any one of the following general formulas (81-7) to (81-18).

[1946] [Chemical Formula 179]

[1947]

[1948] [Chemical Formula 180]

[1949]

[1950]

Chemical Formula 181

[1951]

[1952] [Chemical Formula 182]

[1953]

[1954]

Chemical Formula 183

[1955]

[1956] [Chemical Formula 184]

[1957]

[1958] (In the above general formulas (81-7) to (81-18),

[1959] X8 has the same meaning as X8 in the above general formula (8).

[1960] * represents a single bond bonded to the monovalent group shown in the above general formula (84).

[1961] R 801 ~R 824 Each independently relates to the R group in the above general formulas (81-1) to (81-6) that is not the monovalent group shown in the above general formula (84). 801 ~R 824 The meaning is the same.

[1962] R that does not form the divalent groups shown in general formulas (82) and (83) above and is not the monovalent group shown in general formula (84) above. 801 ~R 808 And R groups that are not monovalent groups represented by the above general formula (84) 811 ~R 814 and R 821 ~R 824 Preferred to be independent

[1963] hydrogen atom,

[1964] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1965] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1966] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1967] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1968] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1969] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[1970] The monovalent group represented by the above general formula (84) is preferably represented by the following general formula (85) or general formula (86).

[1971] [Chemical Formula 185]

[1972]

[1973] (In the above general formula (85),

[1974] R 831 ~R 840 Each independently

[1975] hydrogen atom,

[1976] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1977] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1978] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1979] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1980] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1981] -O-(R 904 The groups shown in the figure,

[1982] -S-(R 905 The groups shown in the figure,

[1983] -N(R 906 (R) 907 The groups shown in the figure,

[1984] Halogen atoms,

[1985] cyano,

[1986] Nitro,

[1987] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1988] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1989] The asterisk (*) in the above general formula (85) has the same meaning as the asterisk (*) in the above general formula (84).

[1990] [Chemical Formula 186]

[1991]

[1992] (In the above general formula (86),

[1993] Ar 801 L 801 and L 803 Ar in the above general formula (84) 801 L 801 and L 803 The meaning is the same, HAr 801 The structure is shown in the following general formula (87).

[1994] [Chemical Formula 187]

[1995]

[1996] (In the above general formula (87),

[1997] X 81 It consists of oxygen or sulfur atoms.

[1998] R 841 ~R 848 Any one of them is related to L 803 Bonded single bonds,

[1999] R is not a single-key letter. 841 ~R 848 Each independently

[2000] hydrogen atom,

[2001] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2002] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2003] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2004] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2005] -Si(R 901 (R) 902 (R) 903The groups shown in the figure,

[2006] -O-(R 904 The groups shown in the figure,

[2007] -S-(R 905 The groups shown in the figure,

[2008] -N(R 906 (R) 907 The groups shown in the figure,

[2009] Halogen atoms,

[2010] cyano,

[2011] Nitro,

[2012] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2013] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[2014] As a compound represented by the above general formula (8), the compounds disclosed in International Publication No. 2014 / 104144 and, for example, the compounds shown below can be cited as specific examples.

[2015]

Chemical Formula 188

[2016]

[2017] [Chemical Formula 189]

[2018]

[2019] [Chemical Formula 190]

[2020]

[2021]

Chemical Formula 191

[2022]

[2023] [Chemical Formula 192]

[2024]

[2025] [Chemical Formula 193]

[2026]

[2027] [Chemical Formula 194]

[2028]

[2029] (The compound represented by general formula (9))

[2030] The compounds represented by general formula (9) will be described.

[2031] [Chemical Formula 195]

[2032]

[2033] (In the above general formula (9),

[2034] A 91 Ring and A 92 Each ring is independent of the others.

[2035] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or

[2036] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2037] Selected from A 91 Ring and A 92 One or more rings in a ring

[2038] * Bonded to the structure shown in the following general formula (92).

[2039] [Chemical Formula 196]

[2040]

[2041] (In the above general formula (92),

[2042] A 93 Ring for

[2043] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or

[2044] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2045] X9 is NR 93 C(R) 94 (R) 95 ), Si(R) 96 (R) 97 ), Ge(R) 98 (R) 99 ), oxygen atoms, sulfur atoms or selenium atoms,

[2046] R 91 and R 92

[2047] They bond together to form substituted or unsubstituted monocyclic rings.

[2048] They bond together to form substituted or unsubstituted fused rings, or

[2049] They do not bond with each other.

[2050] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 91 and R 92 and R 93 ~R 99 Each independently

[2051] hydrogen atom,

[2052] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2053] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2054] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2055] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2056] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2057] -O-(R 904 The groups shown in the figure,

[2058] -S-(R 905 The groups shown in the figure,

[2059] -N(R 906 (R) 907 The groups shown in the figure,

[2060] Halogen atoms,

[2061] cyano,

[2062] Nitro,

[2063] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2064] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[2065] Selected from A 91 Ring and A 92 One or more rings in the ring are bonded to the structure shown in the above general formula (92). That is, in one embodiment, A 91 The cyclic carbon atom of the aforementioned aromatic hydrocarbon ring or the cyclic atom of the aforementioned heterocycle is bonded to the structure shown in the aforementioned general formula (92). Additionally, in one embodiment, A 92 The cyclic carbon atom of the above-mentioned aromatic hydrocarbon ring or the cyclic atom of the above-mentioned heterocycle is bonded to the structure shown in the above-mentioned general formula (92).

[2066] In one embodiment, the group represented by the following general formula (93) is bonded to A 91 Ring and A 92 One or both of them in the ring.

[2067] [Chemical Formula 197]

[2068]

[2069] (In the above general formula (93),

[2070] Ar 91 and Ar 92 Each independently

[2071] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2072] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2073] L 91 ~L 93 Each independently

[2074] single bond,

[2075] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms

[2076] Substituted or unsubstituted divalent heterocyclic groups with 5 to 30 cyclic atoms, or

[2077] A divalent linking group is formed by bonding 2 to 4 groups from the group consisting of a substituted or unsubstituted aryl group with 6 to 30 carbon atoms and a substituted or unsubstituted divalent heterocyclic group with 5 to 30 carbon atoms.

[2078] In the above general formula (93), * indicates that it is related to A. 91 Ring and A 92 The bonding position of any element in the ring.

[2079] In one implementation, besides A 91 Outside the ring, there is A. 92 The cyclic carbon atom of the aforementioned aromatic hydrocarbon ring or the cyclic atom of the aforementioned heterocycle is bonded to the structure shown in the aforementioned general formula (92). In this case, the structures shown in the aforementioned general formula (92) may be the same as or different from each other.

[2080] In one implementation, R 91 and R 92 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure.

[2081] In one implementation, R 91 and R92 They bond together to form a fluorene structure.

[2082] In one implementation, ring A 91 And Ring A 92 Each is an aromatic hydrocarbon ring, either substituted or unsubstituted, having 6 to 50 carbon atoms, such as a substituted or unsubstituted benzene ring.

[2083] In one implementation, ring A 93 A cyclic aromatic hydrocarbon ring with 6 to 50 carbon atoms, either substituted or unsubstituted, such as a substituted or unsubstituted benzene ring.

[2084] In one implementation, X9 is an oxygen atom or a sulfur atom.

[2085] As a compound represented by the above general formula (9), the following compounds can be cited as specific examples.

[2086] [Chemical Formula 198]

[2087]

[2088]

Chemical Formula 199

[2089]

[2090] [Chemical Formula 200]

[2091]

[2092]

Chemical Formula 201

[2093]

[2094] (The compound represented by general formula (10))

[2095] The compounds represented by general formula (10) will be described.

[2096]

Chemical Formula 202

[2097]

[2098]

Chemical Formula 203

[2099]

[2100] (In the above general formula (10),

[2101] Ax1 ring is a ring as shown in the above general formula (10a) that is fused at any position of adjacent rings.

[2102] Ax2 ring is a ring as shown in the above general formula (10b) that is fused at any position between adjacent rings.

[2103] The two asterisks in the above general formula (10b) are bonded to any position of the Ax3 ring.

[2104] X A and X B Each independently is C(R) 1003 (R) 1004 ), Si(R) 1005 (R) 1006 ), oxygen atom or sulfur atom,

[2105] Ax3 ring is

[2106] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or

[2107] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2108] Ar 1001 for

[2109] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2110] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2111] R 1001 ~R 1006 Each independently

[2112] hydrogen atom,

[2113] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2114] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2115] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2116] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2117] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2118] -O-(R 904 The groups shown in the figure,

[2119] -S-(R 905 The groups shown in the figure,

[2120] -N(R 906 (R) 907 The groups shown in the figure,

[2121] Halogen atoms,

[2122] cyano,

[2123] Nitro,

[2124] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2125] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2126] mx1 is 3, mx2 is 2.

[2127] Multiple R 1001 They are the same or different.

[2128] Multiple R 1002 They are the same or different.

[2129] ax is 0, 1, or 2.

[2130] When ax is 0 or 1, the structures within the parentheses shown in "3-ax" are either the same or different.

[2131] When ax = 2, multiple Ar 1001 (They may be the same or different.)

[2132] In one implementation, Ar 1001 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[2133] In one embodiment, the Ax3 ring is a substituted or unsubstituted aromatic hydrocarbon ring with 6 to 50 carbon atoms, such as a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring.

[2134] In one implementation, R 1003 and R 1004 Each is an alkyl group, either substituted or unsubstituted, having 1 to 50 carbon atoms.

[2135] In one implementation, ax is 1.

[2136] As a compound represented by the above general formula (10), the following compounds can be cited as specific examples.

[2137]

Chemical Formula 204

[2138]

[2139] In one embodiment, the light-emitting layer contains, as a second compound, selected from...

[2140] The compounds represented by the above general formula (4),

[2141] The compounds represented by the above general formula (5),

[2142] The compounds represented by the above general formula (7),

[2143] The compounds represented by the above general formula (8),

[2144] The compounds represented by the above general formula (9) and

[2145] One or more compounds in the group consisting of compounds represented by the following general formula (63a).

[2146]

Chemical Formula 205

[2147]

[2148] (In the above general formula (63a),

[2149] R 631 With R 646 They may bond to form substituted or unsubstituted heterocycles, or they may not form substituted or unsubstituted heterocycles.

[2150] R 633 With R 647 They may bond to form substituted or unsubstituted heterocycles, or they may not form substituted or unsubstituted heterocycles.

[2151] R 634 With R 651 They may bond to form substituted or unsubstituted heterocycles, or they may not form substituted or unsubstituted heterocycles.

[2152] R 641 With R 642 They may bond to form substituted or unsubstituted heterocycles, or they may not form substituted or unsubstituted heterocycles.

[2153] R 631 ~R 651 Two or more adjacent groups

[2154] They bond together to form substituted or unsubstituted monocyclic rings.

[2155] They bond together to form substituted or unsubstituted fused rings, or

[2156] They do not bond with each other.

[2157] R does not form the aforementioned substituted or unsubstituted heterocycles, does not form the aforementioned monocyclic rings, and does not form the aforementioned fused rings. 631 ~R 651 Each independently

[2158] hydrogen atom,

[2159] Halogen atoms,

[2160] cyano,

[2161] Nitro,

[2162] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2163] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2164] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2165] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2166] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2167] -O-(R 904 The groups shown in the figure,

[2168] -S-(R 905 The groups shown in the figure,

[2169] -N(R 906 (R) 907 The groups shown in the figure,

[2170] A substituted or unsubstituted aryl group with 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 cyclic atoms.

[2171] Among them, R does not form the aforementioned substituted or unsubstituted heterocycles, does not form the aforementioned monocyclic rings, and does not form the aforementioned fused rings. 631 ~R 651 At least one of them is

[2172] Halogen atoms,

[2173] cyano,

[2174] Nitro,

[2175] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2176] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2177] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2178] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2179] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2180] -O-(R 904 The groups shown in the figure,

[2181] -S-(R 905 The groups shown in the figure,

[2182] -N(R 906 (R) 907 The groups shown in the figure,

[2183] Halogen atoms,

[2184] cyano,

[2185] Nitro,

[2186] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2187] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[2188] In one embodiment, the compound represented by the above general formula (4) is a compound represented by the above general formula (41-3), general formula (41-4) or general formula (41-5), wherein the A1 ring in the above general formula (41-5) is a fused aromatic hydrocarbon ring with 10 to 50 cyclic carbon atoms, substituted or unsubstituted, or a fused heterocycle with 8 to 50 cyclic atoms, substituted or unsubstituted.

[2189] In one embodiment, the substituted or unsubstituted fused aromatic hydrocarbon rings with 10 to 50 carbon atoms in the above general formulas (41-3), (41-4), and (41-5) are...

[2190] Substituted or unsubstituted naphthalene ring,

[2191] Substituted or unsubstituted anthracene rings, or

[2192] Substituted or unsubstituted fluorene ring,

[2193] The above-mentioned fused heterocycles with 8 to 50 cyclic atoms, whether substituted or unsubstituted, are

[2194] Substituted or unsubstituted dibenzofuran rings,

[2195] Substituted or unsubstituted carbazole ring, or

[2196] Substituted or unsubstituted dibenzothiophene ring.

[2197] In one embodiment, the substituted or unsubstituted fused aromatic hydrocarbon ring with 10 to 50 carbon atoms in the above general formulas (41-3), (41-4), or (41-5) is...

[2198] Substituted or unsubstituted naphthalene ring, or

[2199] Substituted or unsubstituted fluorene ring,

[2200] The above-mentioned fused heterocycles with 8 to 50 cyclic atoms, whether substituted or unsubstituted, are

[2201] Substituted or unsubstituted dibenzofuran rings,

[2202] Substituted or unsubstituted carbazole ring, or

[2203] Substituted or unsubstituted dibenzothiophene ring.

[2204] In one embodiment, the compound represented by the above general formula (4) is selected from...

[2205] The compounds represented by the following general formula (461),

[2206] The compounds represented by the following general formula (462),

[2207] The compounds represented by the following general formula (463),

[2208] The compounds represented by the following general formula (464),

[2209] The compounds represented by the following general formula (465),

[2210] The compounds represented by the following general formula (466), and

[2211] The group consisting of compounds represented by the following general formula (467).

[2212]

Chemical Formula 206

[2213]

[2214] [Chemical Formula 207]

[2215]

[2216] [Chemical Formula 208]

[2217]

[2218]

Chemical Formula 209

[2219]

[2220]

Chemical Formula 210

[2221]

[2222] (In the above general formulas (461) to (467),

[2223] R 421 ~R427 R 431 ~R 436 R 440 ~R 448 and R 451 ~R 454 One or more of the groups consisting of two or more adjacent elements.

[2224] They bond together to form substituted or unsubstituted monocyclic rings.

[2225] They bond together to form substituted or unsubstituted fused rings, or

[2226] They do not bond with each other.

[2227] R 437 R 438 and R that does not form the aforementioned single ring and does not form the aforementioned fused ring. 421 ~R 427 R 431 ~R 436 R 440 ~R 448 and R 451 ~R 454 Each independently

[2228] hydrogen atom,

[2229] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2230] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2231] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2232] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2233] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2234] -O-(R 904 The groups shown in the figure,

[2235] -S-(R 905 The groups shown in the figure,

[2236] -N(R 906 (R) 907 The groups shown in the figure,

[2237] Halogen atoms,

[2238] cyano,

[2239] Nitro,

[2240] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2241] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2242] X4 represents an oxygen atom, NR 801 or C(R) 802 (R) 803 ),

[2243] R 801 R 802 and R 803 Each independently

[2244] hydrogen atom,

[2245] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2246] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2247] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2248] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2249] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or

[2250] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.

[2251] In R 801 In cases where multiple R801s exist, the multiple R801s may be identical or different.

[2252] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.

[2253] In R 803 In the case of multiple Rs, multiple Rs 803 (They may be the same or different.)

[2254] In one implementation, R 421 ~R 427 and R 440 ~R 448 Each independently

[2255] hydrogen atom,

[2256] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2257] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2258] In one implementation, R 421 ~R 427 and R 440 ~R 447 Each independently chooses freedom

[2259] hydrogen atom,

[2260] Substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, and

[2261] The group consisting of substituted or unsubstituted heterocyclic groups with 5 to 18 cyclic atoms.

[2262] In one embodiment, the compound represented by the above general formula (41-3) is the compound represented by the following general formula (41-3-1).

[2263]

Chemical Formula 211

[2264]

[2265] (In the above general formula (41-3-1), R) 423 R 425 R 426 R 442 R 444 and R 445 Each independently relates to R in the above general formula (41-3). 423 R 425 R 426 R 442 R 444 and R 445 The meaning is the same.

[2266] In one embodiment, the compound represented by the above general formula (41-3) is the compound represented by the following general formula (41-3-2).

[2267]

Chemical Formula 212

[2268]

[2269] (In the above general formula (41-3-2), R) 421 ~R 427 and R 440 ~R 448 Each independently relates to R in the above general formula (41-3). 421 ~R 427 and R 440 ~R 448 Same meaning

[2270] Among them, R 421 ~R 427 and R 440~R 446 At least one of them is -N(R) 906 (R) 907 The group shown in the diagram.

[2271] In one embodiment, R in the above formula (41-3-2) 421 ~R 427 and R 440 ~R 446 Any two of them are -N(R) 906 (R) 907 The group shown is ).

[2272] In one embodiment, the compound represented by formula (41-3-2) above is the compound represented by formula (41-3-3) below.

[2273]

Chemical Formula 213

[2274]

[2275] (In the above general formula (41-3-3), R) 421 ~R 424 R 440 ~R 443 R 447 and R 448 Each independently relates to R in the above general formula (41-3). 421 ~R 424 R 440 ~R 443 R 447 and R 448 Same meaning

[2276] R A R B R C and R D Each independently

[2277] Substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, or

[2278] (Substituted or unsubstituted heterocyclic groups with 5 to 18 cyclic atoms)

[2279] In one embodiment, the compound represented by formula (41-3-3) above is the compound represented by formula (41-3-4) below.

[2280]

Chemical Formula 214

[2281]

[2282] (In the above general formula (41-3-4), R) 447 R 448R A R B R C and R D Each independently relates to R in the above equation (41-3-3) 447 R 448 R A R B R C and R D The meaning is the same.

[2283] In one implementation, R A R B R C and R D Each is an aryl group, either substituted or unsubstituted, with 6 to 18 carbon atoms in a cyclic structure.

[2284] In one implementation, R A R R R C and R D Each can be a substituted or unsubstituted phenyl group.

[2285] In one implementation, R 447 and R 448 It is a hydrogen atom.

[2286] In one embodiment, the substituents expressed as "substituted or unsubstituted" in the above formulas are:

[2287] Unsubstituted alkyl groups with 1 to 50 carbon atoms

[2288] Unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2289] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms

[2290] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2291] -Si(R 901a (R) 902a (R) 903a ),

[2292] -O-(R 904a ),

[2293] -S-(R 905a ),

[2294] -N(R 906a (R) 907a ),

[2295] Halogen atoms,

[2296] cyano,

[2297] Nitro,

[2298] Unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2299] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms

[2300] R 901a ~R 907a Each independently

[2301] hydrogen atom,

[2302] Unsubstituted alkyl groups with 1 to 50 carbon atoms

[2303] Unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2304] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms

[2305] In R 901a In cases where there are two or more R's, there are two or more R's. 901a They are the same or different.

[2306] In R 902a In cases where there are two or more R's, there are two or more R's. 902a They are the same or different.

[2307] In R 903a In cases where there are two or more R's, there are two or more R's. 903a They are the same or different.

[2308] In R 904a In cases where there are two or more R's, there are two or more R's. 904a They are the same or different.

[2309] In R 905a In cases where there are two or more R's, there are two or more R's. 905a They are the same or different.

[2310] In R 906a In cases where there are two or more R's, there are two or more R's. 906a They are the same or different.

[2311] In R 907a In cases where there are two or more R's, there are two or more R's. 907a They are the same or different.

[2312] In one embodiment, the substituents expressed as "substituted or unsubstituted" in the above formulas are:

[2313] Unsubstituted alkyl groups with 1 to 50 carbon atoms

[2314] Unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2315] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms.

[2316] In one embodiment, the substituents expressed as "substituted or unsubstituted" in the above formulas are:

[2317] Unsubstituted alkyl groups having 1 to 18 carbon atoms

[2318] Unsubstituted aryl groups with 6 to 18 carbon atoms, or

[2319] Unsubstituted heterocyclic groups with 5 to 18 cyclic atoms.

[2320] In the organic EL element involved in this embodiment, the second compound is preferably a compound that exhibits luminescence with a maximum peak wavelength of 430 nm or more and 480 nm or less.

[2321] The method for determining the maximum peak wavelength of a compound is shown below. Ten samples of the compound to be measured were prepared. -6 mol / L or higher and 10 -5 A toluene solution with a concentration of less than mol / L was added to a quartz cuvette, and the emission spectrum of the sample was measured at room temperature (300K) (vertical axis is set as emission intensity, and horizontal axis is set as wavelength). The emission spectrum can be measured using a spectrophotometer (device name: F-7000) manufactured by Hitachi Advanced Scientific Corporation. It should be noted that the emission spectrum measurement device is not limited to the device used here.

[2322] In the emission spectrum, the peak wavelength of the emission spectrum with the highest emission intensity is taken as the maximum emission peak wavelength. It should be noted that, in this specification, the maximum peak wavelength of fluorescence emission is sometimes referred to as the maximum fluorescence emission peak wavelength (FL-peak).

[2323] In the second compound, groups described as "substituted or unsubstituted" are preferably "unsubstituted".

[2324] Compound 3 and Compound 5

[2325] In the organic EL element of this embodiment, the third and fifth compounds serving as the host materials can be, for example, heterocyclic compounds and fused aromatic compounds. As fused aromatic compounds, anthracene derivatives, pyrene derivatives, etc., are preferred. Derivatives and tetraphenyl derivatives, etc.

[2326] In the organic EL element according to this embodiment, the third compound is preferably the compound shown in the above general formula (1). In this case, the compound shown in general formula (1) contained in the first hole transport layer as the first compound and the compound shown in general formula (1) contained in the light-emitting layer as the third compound are the same as or different from each other.

[2327] Preferably, the third compound in the first light-emitting layer is the compound shown in general formula (1) above, while the fifth compound in the second light-emitting layer is not the compound shown in general formula (1) above. In this case, the compound shown in general formula (1) contained in the first hole transport layer as the first compound and the compound shown in general formula (1) contained in the first light-emitting layer as the third compound are the same as or different from each other.

[2328] In the organic EL element involved in this embodiment, the third compound is preferably a compound represented by the following general formula (2).

[2329] Preferably, the fifth compound in the second light-emitting layer is a compound represented by the following general formula (2), while the third compound in the first light-emitting layer is not a compound represented by the following general formula (2).

[2330] Preferably, the third compound in the first light-emitting layer is the compound shown in the above general formula (1), and the fifth compound in the second light-emitting layer is the compound shown in the following general formula (2).

[2331]

Chemical Formula 215

[2332]

[2333] (In the above general formula (2),)

[2334] R 201 ~R 208 Each independently

[2335] hydrogen atom,

[2336] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2337] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[2338] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2339] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2340] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2341] -Si(R 901 (R) 902 (R) 903The groups shown in the figure,

[2342] -O-(R 904 The groups shown in the figure,

[2343] -S-(R 905 The groups shown in the figure,

[2344] -N(R 906 (R) 907 The groups shown in the figure,

[2345] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[2346] -C(=O)R 801 The groups shown

[2347] -COOR 802 The groups shown

[2348] Halogen atoms,

[2349] cyano,

[2350] Nitro,

[2351] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2352] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2353] L 201 and L 202 Each independently

[2354] single bond,

[2355] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[2356] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2357] Ar 201 and Ar 202 Each independently

[2358] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2359] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[2360] (In the third compound involved in this embodiment, R) 901 R 902 R 903 R 904 R 905 R 906 R 907 R801 and R 802 Each independently

[2361] hydrogen atom,

[2362] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2363] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2364] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2365] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2366] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.

[2367] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.

[2368] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.

[2369] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.

[2370] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.

[2371] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.

[2372] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.

[2373] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[2374] In R 802 In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)

[2375] In the organic EL element involved in this embodiment, it is preferred that,

[2376] R 201~R 208 Each independently

[2377] hydrogen atom,

[2378] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2379] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[2380] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2381] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2382] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2383] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2384] -O-(R 904 The groups shown in the figure,

[2385] -S-(R 905 The groups shown in the figure,

[2386] -N(R 906 (R) 907 The groups shown in the figure,

[2387] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[2388] -C(=O)R 801 The groups shown

[2389] -COOR 802 The groups shown

[2390] Halogen atoms,

[2391] cyano, or

[2392] Nitro,

[2393] L 201 and L 202 Each independently

[2394] single bond,

[2395] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[2396] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2397] Ar 201 and Ar 202Each independently

[2398] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2399] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2400] In the organic EL element involved in this embodiment, it is preferred that,

[2401] L 201 and L 202 Each independently

[2402] single key, or

[2403] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms in a cyclic structure.

[2404] Ar 201 and Ar 202 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure.

[2405] In the organic EL element involved in this embodiment,

[2406] Ar 201 and Ar 202 Preferred to be independent

[2407] phenyl,

[2408] Naphthyl,

[2409] Fiki,

[2410] Biphenyl

[2411] Triphenyl

[2412] Diphenylfluorenyl,

[2413] Dimethylfluorenyl,

[2414] benzodiphenylfluorenyl,

[2415] benzodimethylfluorenyl,

[2416] Dibenzofuranyl,

[2417] Dibenzothiophene group,

[2418] Naphthobenzofuranyl, or

[2419] Naphthobenzothiophene group.

[2420] In the organic EL element of this embodiment, the third compound represented by the above general formula (2) is preferably a compound represented by the following general formulas (201), (202), (203), (204), (205), (206), (207), (208), (209), or (210).

[2421]

Chemical Formula 216

[2422]

[2423]

Chemical Formula 217

[2424]

[2425]

Chemical Formula 218

[2426]

[2427]

Chemical Formula 219

[2428]

[2429]

Chemical Formula 220

[2430]

[2431]

Chemical Formula 221

[2432]

[2433]

Chemical Formula 222

[2434]

[2435]

Chemical Formula 223

[2436]

[2437] [Chemical Formula 224]

[2438]

[2439] [Chemical Formula 225]

[2440]

[2441] (In the above general formulas (201) to (210),

[2442] L 201 and Ar 201 L in the above general formula (2) 201 and Ar 201 Same meaning

[2443] R 201 ~R 208 Each independently relates to R in the above general formula (2) 201 ~R 208 The meaning is the same.

[2444] The third compound represented by the above general formula (2) is also preferably a compound represented by the following general formulas (221), (222), (223), (224), (225), (226), (227), (228) or (229).

[2445]

Chemical Formula 226

[2446]

[2447] [Chemical Formula 227]

[2448]

[2449] [Chemical Formula 228]

[2450]

[2451] [Chemical Formula 229]

[2452]

[2453]

Chemical Formula 230

[2454]

[2455]

Chemical Formula 231

[2456]

[2457]

Chemical Formula 232

[2458]

[2459]

Chemical Formula 233

[2460]

[2461] [Chemical Formula 234]

[2462]

[2463] (In the above general formulas (221), (222), (223), (224), (225), (226), (227), (228), and (229),

[2464] R 201 and R 203 ~R 208 Each independently relates to R in the above general formula (2) 201 and R 203 ~R 208 Same meaning

[2465] L 201 and Ar 201 Each of the above general formulas (2) with L 201 and Ar 201 Same meaning

[2466] L 203 L in the above general formula (2) 201 Same meaning

[2467] L 203 With L 201 They are the same or different.

[2468] Ar 203 Ar in the above general formula (2) 201 Same meaning

[2469] Ar 203 with Ar 201 (They may be the same or different.)

[2470] The third compound represented by the above general formula (2) is also preferably a compound represented by the following general formulas (241), (242), (243), (244), (245), (246), (247), (248) or (249).

[2471] [Chemical Formula 235]

[2472]

[2473] [Chemical Formula 236]

[2474]

[2475] [Chemical Formula 237]

[2476]

[2477] [Chemical Formula 238]

[2478]

[2479] [Chemical Formula 239]

[2480]

[2481] [Chemical Formula 240]

[2482]

[2483]

Chemical Formula 241

[2484]

[2485]

Chemical Formula 242

[2486]

[2487] [Chemical Formula 243]

[2488]

[2489] (In the above general formulas (241), (242), (243), (244), (245), (246), (247), (248), and (249),

[2490] R 201 R 202 and R 204 ~R 208 Each independently relates to R in the above general formula (2) 201 R 202 and R 204 ~R 208 Same meaning

[2491] L 201 and Ar 201 Each of the above general formulas (2) with L 201 and Ar 201 Same meaning

[2492] L 203 L in the above general formula (2) 201 Same meaning

[2493] L 203 With L 201 They are the same or different.

[2494] Ar 203 Ar in the above general formula (2) 201 Same meaning

[2495] Ar 203 with Ar 201 (They may be the same or different.)

[2496] In the third compound represented by the above general formula (2), the R group is not the group represented by the above general formula (21). 201 ~R208 Preferred to be independent

[2497] hydrogen atom,

[2498] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2499] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or

[2500] -Si(R 901 (R) 902 (R) 903 The group shown is ).

[2501] Preferred L 101 for

[2502] single key, or

[2503] Unsubstituted arylene groups with 6 to 22 carbon atoms in the cyclic group,

[2504] Ar 101 It is an aryl group with 6 to 22 carbon atoms, either substituted or unsubstituted.

[2505] In the organic EL element involved in this embodiment, it is preferred that,

[2506] In the third compound represented by the above general formula (2), R 201 ~R 208 Each independently

[2507] hydrogen atom,

[2508] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2509] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or

[2510] -Si(R 901 (R) 902 (R) 903 The group shown is ).

[2511] In the organic EL element involved in this embodiment,

[2512] In the third compound represented by the above general formula (2), R 201 ~R 208 Hydrogen atoms are preferred.

[2513] In the aforementioned third compound, groups described as "substituted or unsubstituted" are preferably "unsubstituted".

[2514] (Method for manufacturing the third compound)

[2515] The third compound can be manufactured using known methods. Alternatively, the third compound can also be manufactured by following known methods, using known alternative reactions and starting materials corresponding to the target substance.

[2516] (Specific examples of the third compound)

[2517] Specific examples of the third compound include the following compounds. However, the present invention is not limited to these specific examples of the third compound. In addition, when the third compound is a compound represented by the above general formula (1), compounds shown as specific examples of the first compound may also be given as specific examples of the third compound.

[2518] [Chemical Formula 244]

[2519]

[2520] [Chemical Formula 245]

[2521]

[2522] [Chemical Formula 246]

[2523]

[2524] [Chemical Formula 247]

[2525]

[2526] [Chemical Formula 248]

[2527]

[2528] [Chemical Formula 249]

[2529]

[2530] [Chemical Formula 250]

[2531]

[2532]

Chemical Formula 251

[2533]

[2534]

Chemical Formula 252

[2535]

[2536] [Chemical Formula 253]

[2537]

[2538] [Chemical Formula 254]

[2539]

[2540] [Chemical Formula 255]

[2541]

[2542] [Chemical Formula 256]

[2543]

[2544] [Chemical Formula 257]

[2545]

[2546] [Chemical Formula 258]

[2547]

[2548] [Chemical Formula 259]

[2549]

[2550] [Chemical Formula 260]

[2551]

[2552]

Chemical Formula 261

[2553]

[2554]

Chemical Formula 262

[2555]

[2556] [Chemical Formula 263]

[2557]

[2558] [Chemical Formula 264]

[2559]

[2560] [Chemical Formula 265]

[2561]

[2562]

Chemical Formula 266

[2563]

[2564] [Chemical Formula 267]

[2565]

[2566] [Chemical Formula 268]

[2567]

[2568] [Chemical Formula 269]

[2569]

[2570] In the organic EL element of this embodiment, when the light-emitting layer contains a second compound and a third compound, the singlet energy S1(H3) of the third compound and the singlet energy S1(D2) of the second compound preferably satisfy the following mathematical formula (Mathematical Formula 1).

[2571] S1(H3)>S1(D2)…(Mathematical Expression 1)

[2572] (Singlet energy S1)

[2573] The following methods can be cited as methods for determining the singlet energy S1 using solutions (sometimes called the solution method).

[2574] 10- of the compound to be measured 5 mol / L or higher and 10- 4 A toluene solution with a concentration of less than mol / L was added to a quartz cuvette, and the absorption spectrum of the sample was measured at room temperature (300K) (the vertical axis is set as absorption intensity, and the horizontal axis is set as wavelength). For the downward tangent on the longer wavelength side of the absorption spectrum, the wavelength value λedge [nm] at the intersection of the tangent and the horizontal axis was substituted into the conversion formula (F2) shown later to calculate the singlet energy.

[2575] Conversion formula (F2): S1[eV]=1239.85 / λedge

[2576] As an absorption spectroscopy measuring device, examples include, but are not limited to, the Hitachi spectrophotometer (device name: U3310).

[2577] The tangent for the downward sag on the longer wavelength side of the absorption spectrum is derived as follows. Consider the tangent at various points on the spectral curve as the longest wavelength maximum is moved along the longer wavelength direction. This tangent exhibits a repeated pattern of decreasing and then increasing slope as the curve declines (i.e., as the value on the vertical axis decreases). The tangent drawn at the point where the slope is minimized on the longest wavelength side (excluding cases where absorbance is below 0.1) is taken as the tangent for the downward sag on the longer wavelength side of the absorption spectrum.

[2578] It should be noted that the maximum absorbance values ​​below 0.2 are not included in the maximum values ​​on the longest wavelength side mentioned above.

[2579] (Thickness of the light-emitting layer)

[2580] The thickness of the light-emitting layer of the organic EL element involved in this embodiment is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and even more preferably 10 nm or more and 50 nm or less. If the thickness of the light-emitting layer is 5 nm or more, it is easy to form the light-emitting layer and easy to adjust the color. If the thickness of the light-emitting layer is 50 nm or less, it is easy to suppress the rise of the driving voltage.

[2581] (The content of compounds in the luminescent layer)

[2582] When the light-emitting layer contains a second compound and a third compound, the content of the second compound and the third compound in the light-emitting layer is preferably within the following ranges, for example.

[2583] The content of the third compound is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less.

[2584] The content of the second compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less.

[2585] The upper limit of the combined content of the second and third compounds in the luminescent layer is 100% by mass.

[2586] It should be noted that this embodiment does not exclude the inclusion of materials other than the second and third compounds in the light-emitting layer.

[2587] In the luminescent layer, the second compound may contain only one type or more types. In the luminescent layer, the third compound may contain only one type or more types.

[2588] The structure of organic EL elements will be further explained below. Symbols will sometimes be omitted.

[2589] (Substrate)

[2590] The substrate is used as a support for the organic electroluminescent (EL) element. Examples of substrates that can be used include glass, quartz, and plastic. Flexible substrates can also be used. A flexible substrate is a substrate that can be bent (flexible). Examples of flexible substrates include plastic substrates. Materials used to form the plastic substrate include, for example, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Inorganic vapor-deposited films can also be used.

[2591] (anode)

[2592] The anode formed on the substrate is preferably a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically 4.0 eV or higher). Examples of such anodes include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metallic materials (e.g., titanium nitride).

[2593] These materials are typically formed by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1% to 10% zinc oxide relative to indium oxide. Alternatively, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5% to 5% tungsten oxide and 0.1% to 1% zinc oxide relative to indium oxide. Furthermore, these materials can also be fabricated using vacuum evaporation, coating, inkjet printing, spin coating, and other similar methods.

[2594] In the EL layer formed on the anode, the hole injection layer formed with the anode in contact with the ground is formed using a composite material that is easy to inject holes with, which is independent of the work function of the anode. Therefore, materials that can be used as electrode materials (such as metals, alloys, conductive compounds and mixtures thereof, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[2595] Elements belonging to Group 1 or Group 2 of the periodic table that have low work functions can also be used, namely alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them. It should be noted that when using alkali metals, alkaline earth metals, and their alloys to form the anode, vacuum evaporation or sputtering methods can be used. Furthermore, when using silver paste, coating or inkjet printing methods can be used.

[2596] (cathode)

[2597] The cathode preferably uses metals, alloys, conductive compounds, and mixtures thereof with low work functions (specifically, below 3.8 eV). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them.

[2598] It should be noted that when using alkali metals, alkaline earth metals, or alloys containing them to form the cathode, vacuum evaporation or sputtering methods can be used. Additionally, when using silver paste, coating or inkjet printing methods can be used.

[2599] It should be noted that by setting an electron injection layer, a wide variety of conductive materials, such as Al, Ag, ITO, graphene, and indium tin oxide containing silicon or silicon oxide, can be used to form cathodes regardless of the work function. These conductive materials can be deposited using methods such as sputtering, inkjet printing, and spin coating.

[2600] (hole injection layer)

[2601] A hole injection layer is a layer containing a material with high hole injection capability. Materials with high hole injection capability can include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.

[2602] In addition, other substances with high hole-injection potential include 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (DNTPD), and 1,3,5-tris[N-(4-diphenylamino)- ...]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]- Aromatic amine compounds such as phenyl(N-phenylamino)benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), and dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile (HAT-CN).

[2603] In addition, high-molecular-weight compounds (oligomers, dendritic polymers, polymers, etc.) can also be used as substances with high hole injection capabilities. Examples include poly(N-vinylcarbazole) (PVK), poly(4-vinyltriphenylamine) (PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (Poly-TPD). Furthermore, acid-containing polymers such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can also be used.

[2604] (Hole transport layer)

[2605] In addition to the first hole transport layer, the organic EL element involved in this embodiment may also have a hole transport layer.

[2606] (Second hole transport layer)

[2607] One embodiment of the organic EL element also includes a second hole transport layer disposed between the anode and the first hole transport layer. Figure 2 The diagram shows an example of the general configuration of an organic EL element having a first hole transport layer and a second hole transport layer.

[2608] The organic EL element 1A includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10A disposed between the anode 3 and the cathode 4. The organic layer 10A is constructed by stacking a hole injection layer 6, a second hole transport layer 72, a first hole transport layer 71, a light-emitting layer 5, an electron transport layer 8, and an electron injection layer 9 in sequence from the anode 3 side.

[2609] Figure 4 The image also shows an example of the general structure of an organic EL element having a first hole transport layer and a second hole transport layer.

[2610] The organic EL element 1C includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10A disposed between the anode 3 and the cathode 4. The organic layer 10A is formed by stacking a hole injection layer 6, a second hole transport layer 72, a first hole transport layer 71, a light-emitting layer 5, an electron transport layer 8, and an electron injection layer 9 in sequence from the anode 3 side. The light-emitting layer 5 further includes a first light-emitting layer 51 and a second light-emitting layer 52.

[2611] In the case of an organic EL element having a second hole transport layer, the first hole transport layer has a first surface on the cathode side and a second surface on the anode side. A light-emitting layer is directly attached to the first surface of the first hole transport layer.

[2612] The second hole transport layer is preferably directly adjacent to the first hole transport layer. That is, the second hole transport layer is directly connected to the second surface of the first hole transport layer.

[2613] The second hole transport layer preferably contains a compound having an amino group. For example, an amino-containing compound is N-(L-) AMN1 -L AMN2 -L AMN3 -Ar AMN 3. Multiple L AMN1 L AMN2 L AMN3 Ar AMN They can be the same or different. L AMN1 L AMN2 L AMN3 It is a single bond, a substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group. AMN It can be a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. L AMN1 L AMN2 L AMN3 Ar AMN For example, it does not contain a pyrene structure.

[2614] The second hole transport layer also preferably contains compounds that have only one amino group in the molecule (sometimes called monoamine compounds).

[2615] The second hole transport layer also preferably contains a compound represented by the following general formula (B1).

[2616] [Chemical Formula 270]

[2617]

[2618] (In the above general formula (B1),

[2619] L A1 L B1 and L C1 Each independently

[2620] single bond,

[2621] Substituted or unsubstituted arylene groups with 6 to 18 carbon atoms, or

[2622] Divalent heterocyclic groups with 5 to 13 cyclic atoms, substituted or unsubstituted.

[2623] In L A1 and L B1 In the case of a single bond, A1 and B1

[2624] They bond together to form substituted or unsubstituted monocyclic rings.

[2625] They bond together to form substituted or unsubstituted fused rings, or

[2626] They do not bond with each other.

[2627] In L A1 and L C1 In the case of a single bond, A1 and C1

[2628] They bond together to form substituted or unsubstituted monocyclic rings.

[2629] They bond together to form substituted or unsubstituted fused rings, or

[2630] They do not bond with each other.

[2631] In L B1 and L C1 In the case of a single bond, B1 and C1

[2632] They bond together to form substituted or unsubstituted monocyclic rings.

[2633] They bond together to form substituted or unsubstituted fused rings, or

[2634] They do not bond with each other.

[2635] A1, B1, and C1, which do not form the aforementioned substituted or unsubstituted monocyclic rings and do not form the aforementioned substituted or unsubstituted fused rings, are each independently...

[2636] Substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[2637] Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms, or

[2638] -Si(R 921 (R) 922 (R) 923 The group shown in the figure,

[2639] R 921 R 922 and R 923 Each is independently a substituted or unsubstituted aryl group with 6 to 30 carbon atoms in a cyclic formation.

[2640] In R 921 In the case of multiple Rs, multiple Rs 921 They are the same or different.

[2641] In R 922 In the case of multiple Rs, multiple Rs 922 They are the same or different.

[2642] In R 923 In the case of multiple Rs, multiple Rs 923 (They may be the same or different.)

[2643] The second hole transport layer is preferably formed only of compounds that do not contain a pyrene structure.

[2644] The second hole transport layer is also preferably formed only of compounds containing amino groups.

[2645] The second hole transport layer also preferably contains a compound with a carbazole group. Examples of compounds with a carbazole group include Cz-(L... CZ1 -L CZ2 -L CZ3 -Ar CZ )1、Cz-(L CZ1 -L CZ2 -L CZ3 -Ar CZ )2、Cz-(L CZ1 -L CZ2 -L CZ3 -Ar CZ 3. Cz is a carbazole group. Multiple L CZ1 L CZ2 L CZ3 Ar CZ They can be the same or different. L CZ1Bonded to carbon or nitrogen atoms of Cz. L CZ1 L CZ2 L CZ3 It is a single bond, a substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group. CZ It can be a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. L CZ1 L CZ2 L CZ3 Ar CZ For example, it does not contain a pyrene structure.

[2646] The hole transport layer beyond the first hole transport layer is a layer containing substances with high hole transport activity. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used in the hole transport layer. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BAFLP), and 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N Aromatic amine compounds such as 4,4',4'-tris(N,N-diphenylamino)triphenylamine (DFLDPBi), 4,4',4'-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), and 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (BSPB) are described herein. -6 cm 2 Substances with a hole mobility of / (V·s) or higher.

[2647] Carbazole derivatives such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (PCzPA), as well as anthracene derivatives such as t-BuDNA, DNA, and DPAnth, can also be used in the hole transport layer. Polymers such as poly(N-vinylcarbazole) (PVK) and poly(4-vinyltriphenylamine) (PVTPA) can also be used.

[2648] The first and second hole transport layers preferably do not contain antimony chloride, vanadium oxide, molybdenum oxide, ruthenium oxide, tungsten oxide, zinc oxide, tin oxide, and iron oxide, and more preferably do not contain inorganic compounds.

[2649] The first and second hole transport layers preferably do not contain hexacyanoazines or phenanthrene.

[2650] It should be noted that any substance whose hole transport capability is higher than that of electrons can use these other substances. It should also be noted that the layer containing the substance with high hole transport capability can be not only a single layer, but also a layer composed of two or more layers of the aforementioned substances stacked together.

[2651] The organic EL element of this embodiment may further include a third hole transport layer as a hole transport layer. Preferably, the third hole transport layer is directly connected to the anode side of the second hole transport layer.

[2652] (Electron transport layer)

[2653] The electron transport layer is a layer containing substances with high electron transport capacity. The electron transport layer can utilize 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) high molecular weight compounds. Specifically, as low molecular weight organic compounds, metal complexes such as Alq, tris(4-methyl-8-hydroxyquinoline)aluminum (Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to metal complexes, heteroaromatic compounds such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviated as p-EtTAZ), phenanthroline (abbreviated as BPhen), copper hydroxide (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)zirconia (abbreviated as BzOs) can also be used. In this embodiment, benzimidazole compounds can be suitably used. The substances described herein mainly have a 10 -6 cm 2 Materials with an electron mobility of / (V·s) or higher. It should be noted that any material whose electron transport capability is higher than its hole transport capability can also be used as the electron transport layer. Furthermore, the electron transport layer can be a single layer or composed of two or more layers of the aforementioned materials stacked together.

[2654] In addition, polymeric compounds can also be used in the electron transport layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy) can be used.

[2655] (Electron injection layer)

[2656] The electron injection layer is a layer containing a material with high electron-injection properties. Alkali metals, alkaline earth metals, or their compounds, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx), can be used in the electron injection layer. Alternatively, materials containing alkali metals, alkaline earth metals, or their compounds can be used; specifically, materials containing magnesium (Mg) in Alq can be used. It should be noted that electron injection from the cathode can be performed more efficiently in this case.

[2657] Alternatively, a composite material consisting of an organic compound and an electron donor can be used in the electron injection layer. Such a composite material exhibits excellent electron injection and electron transport properties because it generates electrons in the organic compound through the electron donor. In this case, the organic compound is preferably a material with excellent electron transport properties; specifically, substances constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) described above can be used. The electron donor can be any substance that exhibits electron-donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides and alkaline earth metal oxides are also preferred, such as lithium oxides, calcium oxides, and barium oxides. Additionally, Lewis bases such as magnesium oxide can also be used. Furthermore, organic compounds such as tetrathiofulvalene (TTF) can also be used.

[2658] (Layer Formation Method)

[2659] The method for forming each layer of the organic EL element in this embodiment is not limited except as specifically mentioned above. Known methods such as vacuum evaporation, sputtering, plasma deposition, ion plating, spin coating, dip coating, flow coating, and inkjet coating can be used.

[2660] (film thickness)

[2661] The thickness of each organic layer in the organic EL element of this embodiment is not limited except as specifically mentioned above. Generally speaking, if the film thickness is too thin, defects such as pinholes are easily generated, while if the film thickness is too thick, a high applied voltage is required, which degrades the efficiency. Therefore, the film thickness of each organic layer in an organic EL element is usually preferably in the range of a few nm to 1 μm.

[2662] According to this embodiment, an organic electroluminescent element with a reduced driving voltage can be provided.

[2663] In the organic EL element of this embodiment, a first hole transport layer containing a first compound represented by the above general formula (1) is directly connected to a light-emitting layer. By stacking the first hole transport layer and the light-emitting layer in this way, the hole injection capability into the light-emitting layer is improved, and the driving voltage is reduced compared to conventional organic EL elements that use an amino compound for the hole transport layer.

[2664] [Second Implementation]

[2665] (Electronic devices)

[2666] The electronic device according to this embodiment incorporates any of the organic EL elements described in the above embodiments. Examples of electronic devices include display devices and light-emitting devices. Examples of display devices include display components (e.g., organic EL flat panel modules), televisions, mobile phones, tablet computers, and personal computers. Examples of light-emitting devices include lighting and vehicle lamps.

[2667] [Variations on the implementation method]

[2668] It should be noted that the present invention is not limited to the above-described embodiments, and modifications and improvements made within the scope of achieving the purpose of the present invention are included in the present invention.

[2669] For example, the light-emitting layer is not limited to one layer; there can be two or more light-emitting layers stacked together. When an organic EL device has two or more light-emitting layers, at least one light-emitting layer needs to satisfy the conditions described in the above embodiments. For example, the other light-emitting layers can be fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize light emission based on electron transitions from a triplet excited state to the ground state.

[2670] In addition, when an organic EL element has multiple light-emitting layers, these light-emitting layers can be arranged adjacent to each other, or they can be a so-called tandem organic EL element formed by stacking multiple light-emitting units with an intermediate layer between them.

[2671] Alternatively, for example, a blocking layer may be disposed adjacent to the cathode side of the light-emitting layer. The blocking layer disposed on the cathode side of the light-emitting layer is preferably in direct contact with the light-emitting layer. The blocking layer disposed on the cathode side of the light-emitting layer preferably blocks at least one of holes and excitons.

[2672] For example, when a barrier layer is grounded on the cathode side of the light-emitting layer, the barrier layer transports electrons and prevents holes from reaching layers closer to the cathode side than the barrier layer (e.g., electron transport layers). In the case of an organic EL device that includes an electron transport layer, it is preferable to include the barrier layer between the light-emitting layer and the electron transport layer.

[2673] In addition, to prevent excitation energy from leaking from the light-emitting layer to its surrounding layers, a barrier layer can be placed adjacent to the light-emitting layer. This prevents excitons generated in the light-emitting layer from moving to layers closer to the electrode side than the barrier layer (such as electron transport layers and hole transport layers).

[2674] Preferably, the light-emitting layer is bonded to the blocking layer.

[2675] Furthermore, the specific structure and shape in the implementation of the present invention may be configured as other structures within the scope of achieving the purpose of the present invention.

[2676] Example

[2677] The present invention will be further described in detail below with reference to specific embodiments. The present invention is not limited to these embodiments in any way.

[2678] <Compound>

[2679] The following shows the structure of the compound represented by general formula (1) used in the manufacture of the organic EL element involved in Examples 1 to 17.

[2680]

Chemical Formula 271

[2681]

[2682]

Chemical Formula 272

[2683]

[2684] The following shows the structures of other compounds used in the manufacture of the organic EL elements involved in Examples 1-17 and Comparative Examples 1-22.

[2685] [Chemical Formula 273]

[2686]

[2687] [Chemical Formula 274]

[2688]

[2689] [Chemical Formula 275]

[2690]

[2691] [Chemical Formula 276]

[2692]

[2693] [Chemical Formula 277]

[2694]

[2695] [Chemical Formula 278]

[2696]

[2697] [Chemical Formula 279]

[2698]

[2699] [Chemical Formula 280]

[2700]

[2701]

Chemical Formula 281

[2702]

[2703]

Chemical Formula 282

[2704]

[2705] [Chemical Formula 283]

[2706]

[2707] <Fabrication of Organic EL Components 1>

[2708] The following describes the fabrication and evaluation of organic EL components.

[2709] (Example 1)

[2710] A glass substrate (manufactured by Geomatec Corporation) with an ITO (Indium Tin Oxide) transparent electrode (anode) and a thickness of 25mm×75mm×1.1mm was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was set to 130nm.

[2711] The cleaned glass substrate with transparent electrode lines was mounted on the substrate holder of the vacuum evaporation apparatus. First, compound HA1 was deposited on the side with transparent electrode lines to cover the transparent electrode, thus forming a hole injection layer with a film thickness of 5 nm.

[2712] Following the formation of the hole injection layer, a third hole transport layer with a thickness of 80 nm was formed by vapor deposition of compound HT1.

[2713] Following the formation of the third hole transport layer, the compound HT2 was evaporated to form a second hole transport layer with a thickness of 10 nm.

[2714] Following the formation of the second hole transport layer, compound PY1 was evaporated to form the first hole transport layer with a thickness of 5 nm.

[2715] Compound BH1 (host material (BH)) and compound BD1 (dopant material (BD)) were co-deposited on the first hole transport layer, with compound BD1 accounting for 2% by mass, to form a light-emitting layer with a thickness of 25 nm.

[2716] Compound ET1 was deposited on the light-emitting layer to form a first electron transport layer (also known as a hole blocking layer) with a thickness of 10 nm (HBL).

[2717] A second electron transport layer (ET) with a thickness of 15 nm was formed by evaporating compound ET2 onto the first electron transport layer.

[2718] An electron injection layer with a thickness of 1 nm was formed by evaporating LiF onto the second electron transport layer.

[2719] A cathode with a film thickness of 80 nm was formed by evaporating metallic Al onto the electron injection layer.

[2720] The simplified component configuration of Embodiment 1 is shown below.

[2721] ITO(130) / HA1(5) / HT1(80) / HT2(10) / PY1(5) / BH1: BD1(25, 98%: 2%) / ET1(10) / ET2(15) / LiF(1) / Al(80)

[2722] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[2723] Similarly, the percentage figures (98% : 2%) within parentheses represent the ratio (mass %) of the host material (compound BH1) and compound BD1 in the luminescent layer. The same notation will be used below.

[2724] (Comparative Example 1)

[2725] The organic EL element of Comparative Example 1 was fabricated in the same manner as in Example 1, except that the thickness of the second hole transport layer was changed to the thickness described in Table 1, and a light-emitting layer was formed directly connected to the second hole transport layer instead of the first hole transport layer.

[2726] (Example 2)

[2727] A glass substrate (manufactured by Geomatec Corporation) with an ITO (Indium Tin Oxide) transparent electrode (anode) and a thickness of 25mm×75mm×1.1mm was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was set to 130nm.

[2728] A cleaned glass substrate with transparent electrode lines was mounted on the substrate holder of a vacuum evaporation apparatus. First, compounds HT3 and HA2 were co-deposited on the side with the transparent electrode lines to form a hole injection layer with a thickness of 10 nm, covering the transparent electrode. The proportion of compound HT3 in this hole injection layer was set to 97% by mass, and the proportion of compound HA2 was set to 3% by mass.

[2729] Following the formation of the hole injection layer, a third hole transport layer with a thickness of 80 nm was formed by vapor deposition of compound HT3.

[2730] Following the formation of the third hole transport layer, a second hole transport layer with a thickness of 10 nm was formed by vapor deposition of compound HT4.

[2731] Following the formation of the second hole transport layer, compound PY1 was evaporated to form the first hole transport layer with a thickness of 5 nm.

[2732] Compound BH2 (host material (BH)) and compound BD2 (dopant material (BD)) were co-deposited on the first hole transport layer, with the proportion of compound BD2 being 4% by mass, to form a light-emitting layer with a film thickness of 20 nm.

[2733] Compound ET1 was deposited on the light-emitting layer to form a first electron transport layer (also known as a hole blocking layer) with a thickness of 10 nm (HBL).

[2734] A second electron transport layer (ET) with a thickness of 15 nm was formed by evaporating compound ET2 onto the first electron transport layer.

[2735] An electron injection layer with a thickness of 1 nm was formed by evaporating LiF onto the second electron transport layer.

[2736] A cathode with a film thickness of 80 nm was formed by evaporating metallic Al onto the electron injection layer.

[2737] The simplified component configuration of Embodiment 2 is shown below.

[2738] ITO(130) / HT3: HA2(10, 97%: 3%) / HT3(80) / HT4(10) / PY1(5) / BH2: BD2(20, 96%: 4%) / ET1(10) / ET2(15) / LiF(1) / A1(80)

[2739] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[2740] Similarly, within parentheses, the percentages (97% : 3%) represent the ratio (mass %) of compound HT3 and compound HA2 in the hole injection layer, and the percentages (96% : 4%) represent the ratio (mass %) of the host material (compound BH2) and compound BD2 in the luminescent layer. The same notation applies below.

[2741] (Comparative Example 2)

[2742] The organic EL element of Comparative Example 2 was fabricated in the same manner as in Example 2, except that a light-emitting layer was formed that was directly connected to the second hole transport layer instead of a first hole transport layer, and the thickness of the light-emitting layer was changed to the thickness described in Table 2.

[2743] (Example 3)

[2744] A glass substrate (manufactured by Geomatec Corporation) with an ITO (Indium Tin Oxide) transparent electrode (anode) and a thickness of 25mm×75mm×1.1mm was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was set to 130nm.

[2745] A cleaned glass substrate with transparent electrode lines was mounted on the substrate holder of a vacuum evaporation apparatus. First, compounds HT3 and HA2 were co-deposited on the side with the transparent electrode lines to form a hole injection layer with a thickness of 10 nm, covering the transparent electrode. The proportion of compound HT3 in this hole injection layer was set to 97% by mass, and the proportion of compound HA2 was set to 3% by mass.

[2746] Following the formation of the hole injection layer, a third hole transport layer with a thickness of 80 nm was formed by vapor deposition of compound HT3.

[2747] Following the formation of the third hole transport layer, a second hole transport layer with a thickness of 10 nm was formed by vapor deposition of compound HT4.

[2748] Following the formation of the second hole transport layer, compound PY1 was evaporated to form the first hole transport layer with a thickness of 5 nm.

[2749] Compound BH2 (host material (BH)) and compound BD2 (dopant material (BD)) were co-deposited on the first hole transport layer, with the proportion of compound BD2 being 4% by mass, to form a light-emitting layer with a film thickness of 20 nm.

[2750] The compound ET3 was deposited on the light-emitting layer to form a first electron transport layer (also known as a hole blocking layer) with a thickness of 10 nm.

[2751] A second electron transport layer (ET) with a thickness of 15 nm was formed by evaporating compound ET2 onto the first electron transport layer.

[2752] An electron injection layer with a thickness of 1 nm was formed by evaporating LiF onto the second electron transport layer.

[2753] A cathode with a film thickness of 80 nm was formed by evaporating metallic Al onto the electron injection layer.

[2754] The simplified component configuration of Embodiment 3 is shown below.

[2755] ITO(130) / HT3: HA2(10, 97%: 3%) / HT3(80) / HT4(10) / PY1(5) / BH2: BD2(20, 96%: 4%) / ET3(10) / ET2(15) / LiF(1) / Al(80)

[2756] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[2757] Similarly, within parentheses, the percentages (97% : 3%) represent the ratio (mass %) of compound HT3 and compound HA2 in the hole injection layer, and the percentages (96% : 4%) represent the ratio (mass %) of the host material (compound BH2) and compound BD2 in the luminescent layer. The same notation applies below.

[2758] (Comparative Example 3)

[2759] The organic EL element of Comparative Example 3 was fabricated in the same manner as in Example 3, except that a light-emitting layer was formed that was directly connected to the second hole transport layer instead of a first hole transport layer, and the thickness of the light-emitting layer was changed to the thickness described in Table 3.

[2760] (Example 4)

[2761] A glass substrate (manufactured by Geomatec Corporation) with an ITO (Indium Tin Oxide) transparent electrode (anode) and a thickness of 25mm×75mm×1.1mm was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was set to 130nm.

[2762] A cleaned glass substrate with transparent electrode lines was mounted on the substrate holder of a vacuum evaporation apparatus. First, compounds HT3 and HA2 were co-deposited on the side with the transparent electrode lines to form a hole injection layer with a thickness of 10 nm, covering the transparent electrode. The proportion of compound HT3 in this hole injection layer was set to 97% by mass, and the proportion of compound HA2 was set to 3% by mass.

[2763] Following the formation of the hole injection layer, a third hole transport layer with a thickness of 80 nm was formed by vapor deposition of compound HT3.

[2764] Following the formation of the third hole transport layer, compound HT5 was vapor-deposited to form a second hole transport layer with a thickness of 10 nm.

[2765] Following the formation of the second hole transport layer, compound PY1 was evaporated to form the first hole transport layer with a thickness of 5 nm.

[2766] Compound BH2 (host material (BH)) and compound BD2 (dopant material (BD)) were co-deposited on the first hole transport layer, with the proportion of compound BD2 being 4% by mass, to form a light-emitting layer with a film thickness of 20 nm.

[2767] Compound ET1 was deposited on the light-emitting layer to form a first electron transport layer (also known as a hole blocking layer) with a thickness of 10 nm (HBL).

[2768] A second electron transport layer (ET) with a thickness of 15 nm was formed by evaporating compound ET2 onto the first electron transport layer.

[2769] An electron injection layer with a thickness of 1 nm was formed by evaporating LiF onto the second electron transport layer.

[2770] A cathode with a film thickness of 80 nm was formed by evaporating metallic Al onto the electron injection layer.

[2771] The simplified component configuration of Example 4 is shown below.

[2772] ITO(130) / HT3: HA2(10, 97%: 3%) / HT3(80) / HT5(10) / PY1(5) / BH2: BD2(20, 96%: 4%) / ET1(10) / ET2(15) / LiF(1) / Al(80)

[2773] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[2774] Similarly, within parentheses, the percentages (97% : 3%) represent the ratio (mass %) of compound HT3 and compound HA2 in the hole injection layer, and the percentages (96% : 4%) represent the ratio (mass %) of the host material (compound BH2) and compound BD2 in the luminescent layer. The same notation applies below.

[2775] (Comparative Example 4)

[2776] The organic EL element of Comparative Example 4 was fabricated in the same manner as in Example 4, except that a light-emitting layer was formed that was directly connected to the second hole transport layer instead of a first hole transport layer, and the thickness of the light-emitting layer was changed to the thickness described in Table 4.

[2777] (Example 5)

[2778] A glass substrate (manufactured by Geomatec Corporation) with an ITO (Indium Tin Oxide) transparent electrode (anode) and a thickness of 25mm×75mm×1.1mm was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was set to 130nm.

[2779] A cleaned glass substrate with transparent electrode lines was mounted on the substrate holder of a vacuum evaporation apparatus. First, compounds HT3 and HA2 were co-deposited on the side with the transparent electrode lines to form a hole injection layer with a thickness of 10 nm, covering the transparent electrode. The proportion of compound HT3 in this hole injection layer was set to 97% by mass, and the proportion of compound HA2 was set to 3% by mass.

[2780] Following the formation of the hole injection layer, a third hole transport layer with a thickness of 80 nm was formed by vapor deposition of compound HT3.

[2781] Following the formation of the third hole transport layer, compound HT5 was vapor-deposited to form a second hole transport layer with a thickness of 10 nm.

[2782] Following the formation of the second hole transport layer, compound PY1 was evaporated to form the first hole transport layer with a thickness of 5 nm.

[2783] Compound BH2 (host material (BH)) and compound BD2 (dopant material (BD)) were co-deposited on the first hole transport layer, with the proportion of compound BD2 being 4% by mass, to form a light-emitting layer with a film thickness of 20 nm.

[2784] The compound ET3 was deposited on the light-emitting layer to form a first electron transport layer (also known as a hole blocking layer) with a thickness of 10 nm.

[2785] A second electron transport layer (ET) with a thickness of 15 nm was formed by evaporating compound ET2 onto the first electron transport layer.

[2786] An electron injection layer with a thickness of 1 nm was formed by evaporating LiF onto the second electron transport layer.

[2787] A cathode with a film thickness of 80 nm was formed by evaporating metallic Al onto the electron injection layer.

[2788] The simplified component configuration of Embodiment 5 is shown below.

[2789] ITO(130) / HT3: HA2(10, 97%: 3%) / HT3(80) / HT5(10) / PY1(5) / BH2: BD2(20, 96%: 4%) / ET3(10) / ET2(15) / LiF(1) / Al(80)

[2790] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[2791] Similarly, within parentheses, the percentages (97% : 3%) represent the ratio (mass %) of compound HT3 and compound HA2 in the hole injection layer, and the percentages (96% : 4%) represent the ratio (mass %) of the host material (compound BH2) and compound BD2 in the luminescent layer. The same notation applies below.

[2792] (Comparative Example 5)

[2793] The organic EL element of Comparative Example 5 was fabricated in the same manner as in Example 5, except that a light-emitting layer was formed that was directly connected to the second hole transport layer instead of a first hole transport layer, and the thickness of the light-emitting layer was changed to the thickness described in Table 5.

[2794] (Comparative Example 6)

[2795] The organic EL element of Comparative Example 6 was fabricated in the same manner as in Example 1, except that a third hole transport layer and a second hole transport layer were not formed, and the first hole transport layer was changed to the film thickness described in Table 1 after the formation of the hole injection layer.

[2796] (Comparative Example 7)

[2797] The organic EL element of Comparative Example 7 was fabricated in the same manner as in Example 2, except that the third hole transport layer and the second hole transport layer were not formed, and the first hole transport layer was changed to the film thickness described in Table 2 after the formation of the hole injection layer.

[2798] (Comparative Example 8)

[2799] The organic EL element of Comparative Example 8 was fabricated in the same manner as in Example 3, except that a third hole transport layer and a second hole transport layer were not formed, and the first hole transport layer was changed to the film thickness described in Table 3 after the formation of the hole injection layer.

[2800] <Evaluation of Organic EL Components>

[2801] The organic EL elements fabricated in Examples 1-17 and Comparative Examples 1-22 were evaluated as follows. The evaluation results are shown in Tables 1-13.

[2802] • Drive voltage

[2803] The measurement was performed by applying an electric current between the anode and cathode, resulting in a current density of 10 mA / cm². 2 Voltage at that time (unit: V).

[2804] Table 1

[2805]

[2806] Table 2

[2807]

[2808] Table 3

[2809]

[2810] Table 4

[2811]

[2812] Table 5

[2813]

[2814] As shown in Tables 1-5, in the organic EL elements of Examples 1-5, the first hole transport layer containing the first compound of general formula (1) is directly connected to the light-emitting layer. Compared to the elements of Comparative Examples 1-5, where the second hole transport layer containing a material with an amine backbone is directly connected to the light-emitting layer, the driving voltage is reduced. Furthermore, in the organic EL elements of Examples 1-5, the first hole transport layer containing the first compound of general formula (1) is directly connected to the light-emitting layer, and the first hole transport layer is directly connected to the second hole transport layer containing a compound with an amino group. Compared to the elements of Comparative Examples 6-8, where the hole injection layer is directly connected to the first hole transport layer, the driving voltage is reduced.

[2815] <Fabrication of Organic EL Components 2>

[2816] (Example 6)

[2817] A glass substrate (manufactured by Geomatec Corporation) with an ITO (Indium Tin Oxide) transparent electrode (anode) and a thickness of 25mm×75mm×1.1mm was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was set to 130nm.

[2818] A cleaned glass substrate with transparent electrode lines was mounted on the substrate holder of a vacuum evaporation apparatus. First, compound HT6 and compound HA2 were co-deposited on the side with the transparent electrode lines to form a hole injection layer with a thickness of 10 nm, covering the transparent electrode. The proportion of compound HT6 in this hole injection layer was set to 97% by mass, and the proportion of compound HA2 was set to 3% by mass.

[2819] Following the formation of the hole injection layer, a third hole transport layer with a thickness of 85 nm was formed by vapor deposition of compound HT6.

[2820] Following the formation of the third hole transport layer, a second hole transport layer with a thickness of 2.5 nm was formed by vapor deposition of compound HT7.

[2821] Following the formation of the second hole transport layer, the compound PY2 was evaporated to form the first hole transport layer with a thickness of 2.5 nm.

[2822] Compound BH3 (host material (BH)) and compound BD3 (dopant material (BD)) were co-deposited on the first hole transport layer, with the proportion of compound BD3 being 2% by mass, to form a light-emitting layer with a film thickness of 20 nm.

[2823] The compound ET4 was deposited on the light-emitting layer to form a first electron transport layer (also known as a hole blocking layer) (HBL) with a thickness of 5 nm.

[2824] A second electron transport layer (ET) with a thickness of 25 nm was formed by co-evaporating compounds ET5 and Liq onto the first electron transport layer (HBL). The proportions of ET5 and Liq in the second electron transport layer (ET) were set to 50% by mass. It should be noted that Liq is an abbreviation for (8-hydroxyquinoline)lithium.

[2825] An electron injection layer with a thickness of 1 nm was formed by evaporating Liq onto the second electron transport layer.

[2826] A cathode with a film thickness of 80 nm was formed by evaporating metallic Al onto the electron injection layer.

[2827] The simplified component configuration of Embodiment 6 is shown below.

[2828] ITO(130) / HT6: HA2(10, 97%: 3%) / HT6(85) / HT7(2.5) / PY2(2.5) / BH3: BD3(20, 98%: 2%) / ET4(5) / ET5: Liq(25, 50%: 50%) / Liq(1) / Al(80)

[2829] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[2830] Similarly, within parentheses, the percentages (97% : 3%) represent the ratio (mass %) of compounds HT6 and HA2 in the hole injection layer, the percentages (98% : 2%) represent the ratio (mass %) of the host material (compound BH3) and BD3 in the emissive layer, and the percentages (50% : 50%) represent the ratio (mass %) of compounds ET5 and Liq in the second electron transport layer (ET). The same notation applies hereinafter.

[2831] (Comparative Example 9)

[2832] The organic EL element of Comparative Example 9 was fabricated in the same manner as in Example 6, except that the thickness of the second hole transport layer was changed to the thickness described in Table 6, and a light-emitting layer was formed directly in contact with the second hole transport layer instead of forming the first hole transport layer.

[2833] (Comparative Example 10)

[2834] The organic EL element of Comparative Example 10 was fabricated in the same manner as in Example 6, except that a third hole transport layer and a second hole transport layer were not formed, and the first hole transport layer was changed to the film thickness described in Table 6 after the formation of the hole injection layer.

[2835] Table 6

[2836]

[2837] (Example 7)

[2838] The organic EL element of Example 7 was fabricated in the same manner as in Example 6, except that the compound of the first hole transport layer was changed to the compound described in Table 7 to form the first hole transport layer.

[2839] (Comparative Example 11)

[2840] The organic EL element of Comparative Example 11 was fabricated in the same manner as Comparative Example 10, except that the compound PY2 of the first hole transport layer was changed to compound PY3 as described in Table 7 to form the first hole transport layer.

[2841] Table 7

[2842]

[2843] (Example 8)

[2844] The organic EL element of Example 8 was fabricated in the same manner as in Example 6, except that the compound PY2 of the first hole transport layer was replaced with compound PY4 as described in Table 8 to form the first hole transport layer, and the compound BH3 of the light-emitting layer was replaced with compound BH4 as described in Table 8 to form the light-emitting layer.

[2845] (Comparative Example 12)

[2846] The organic EL element of Comparative Example 12 was fabricated in the same manner as Comparative Example 9, except that the compound BH3 of the light-emitting layer was replaced with compound BH4 as described in Table 8 to form the light-emitting layer.

[2847] (Comparative Example 13)

[2848] The organic EL element of Comparative Example 13 was fabricated in the same manner as that of Comparative Example 10, except that the compound PY2 of the first hole transport layer was replaced with compound PY4 as described in Table 8 to form the first hole transport layer, and the compound BH3 of the light-emitting layer was replaced with compound BH4 as described in Table 8 to form the light-emitting layer.

[2849] Table 8

[2850]

[2851] (Example 9)

[2852] The organic EL element of Example 9 was fabricated in the same manner as in Example 8, except that the compound PY4 of the first hole transport layer was replaced with compound PY5 as described in Table 9 to form the first hole transport layer.

[2853] (Comparative Example 14)

[2854] The organic EL element of Comparative Example 14 was fabricated in the same manner as Comparative Example 13, except that the compound PY4 of the first hole transport layer was changed to compound PY5 as described in Table 9 to form the first hole transport layer.

[2855] Table 9

[2856]

[2857] (Example 10)

[2858] A glass substrate (manufactured by Geomatec Corporation) with an ITO (Indium Tin Oxide) transparent electrode (anode) and a thickness of 25mm×75mm×1.1mm was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was set to 130nm.

[2859] A cleaned glass substrate with transparent electrode lines was mounted on the substrate holder of a vacuum evaporation apparatus. First, compound HT6 and compound HA2 were co-deposited on the side with the transparent electrode lines to form a hole injection layer with a thickness of 10 nm, covering the transparent electrode. The proportion of compound HT6 in this hole injection layer was set to 97% by mass, and the proportion of compound HA2 was set to 3% by mass.

[2860] Following the formation of the hole injection layer, a third hole transport layer with a thickness of 80 nm was formed by vapor deposition of compound HT6.

[2861] Following the formation of the third hole transport layer, a second hole transport layer with a thickness of 2.5 nm was formed by vapor deposition of compound HT7.

[2862] Following the formation of the second hole transport layer, the compound PY2 was evaporated to form the first hole transport layer with a thickness of 2.5 nm.

[2863] Compound PY2 (host material) and compound BD3 (dopant material) were co-deposited on the first hole transport layer, with the proportion of compound BD3 being 2% by mass, to form a first light-emitting layer with a film thickness of 12.5 nm.

[2864] Compound BH3 (the host material) and compound BD3 (the dopant material) were co-deposited on the first luminescent layer, with the proportion of compound BD3 being 2% by mass, to form a second luminescent layer with a film thickness of 12.5 nm.

[2865] Compound ET4 was deposited on the second light-emitting layer to form a first electron transport layer (also known as a hole blocking layer) (HBL) with a thickness of 5 nm.

[2866] A second electron transport layer (ET) with a thickness of 25 nm was formed by co-evaporating compounds ET5 and Liq onto the first electron transport layer (HBL). The proportions of ET5 and Liq in the second electron transport layer (ET) were set to 50% by mass.

[2867] An electron injection layer with a thickness of 1 nm was formed by evaporating Liq onto the second electron transport layer.

[2868] A cathode with a film thickness of 80 nm was formed by evaporating metallic Al onto the electron injection layer.

[2869] The simplified component configuration of Example 10 is shown below.

[2870] ITO(130) / HT6:HA2(10,97%:3%) / HT6(80) / HT7(2.5) / PY2(2.5) / PY2:BD3(12.5,9 8%: 2%) / BH3: BD3 (12.5, 98%: 2%) / ET4 (5) / ET5: Liq (25, 50%: 50%) / Liq (1) / Al (80)

[2871] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[2872] Similarly, within parentheses, the percentages (97% : 3%) represent the ratio (mass %) of compound HT6 and compound HA2 in the hole injection layer, the percentages (98% : 2%) represent the ratio (mass %) of the host material (compound PY2 or compound BH3) and compound BD3 in the emissive layer, and the percentages (50% : 50%) represent the ratio (mass %) of compound ET5 and compound Liq in the second electron transport layer (ET). The same notation applies hereinafter.

[2873] (Example 11)

[2874] The organic EL element of Example 11 was fabricated in the same manner as that of Example 10, except that the film thicknesses of the second hole transport layer and the first hole transport layer were changed to the film thicknesses listed in Table 10.

[2875] (Comparative Example 15)

[2876] The organic EL element of Comparative Example 15 was fabricated in the same manner as in Example 10, except that the thickness of the second hole transport layer was changed to the thickness described in Table 10, and a first light-emitting layer was formed directly in contact with the second hole transport layer instead of forming a first hole transport layer.

[2877] (Comparative Example 16)

[2878] The organic EL element of Comparative Example 16 was fabricated in the same manner as in Example 10, except that a third hole transport layer and a second hole transport layer were not formed, and the first hole transport layer was changed to the film thickness described in Table 10 after the formation of the hole injection layer.

[2879] Table 10

[2880]

[2881] (Example 12)

[2882] A glass substrate (manufactured by Geomatec Corporation) with an ITO (Indium Tin Oxide) transparent electrode (anode) and a thickness of 25mm×75mm×1.1mm was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was set to 130nm.

[2883] A cleaned glass substrate with transparent electrode lines was mounted on the substrate holder of a vacuum evaporation apparatus. First, compound HT6 and compound HA2 were co-deposited on the side with the transparent electrode lines to form a hole injection layer with a thickness of 10 nm, covering the transparent electrode. The proportion of compound HT6 in this hole injection layer was set to 97% by mass, and the proportion of compound HA2 was set to 3% by mass.

[2884] Following the formation of the hole injection layer, a third hole transport layer with a thickness of 80 nm was formed by vapor deposition of compound HT6.

[2885] Following the formation of the third hole transport layer, the compound HT7 was vapor-deposited to form a second hole transport layer with a thickness of 4 nm.

[2886] Following the formation of the second hole transport layer, the compound PY3 was evaporated to form the first hole transport layer with a thickness of 1 nm.

[2887] Compound PY4 (host material) and compound BD3 (dopant material) were co-deposited on the first hole transport layer, with the proportion of compound BD3 being 2% by mass, to form a first light-emitting layer with a thickness of 10 nm.

[2888] A second light-emitting layer with a thickness of 15 nm was formed by co-evaporating compound BH4 (host material) and compound BD3 (dopant material) onto the first light-emitting layer, with compound BD3 accounting for 2% by mass.

[2889] Compound ET4 was deposited on the second light-emitting layer to form a first electron transport layer (also known as a hole blocking layer) (HBL) with a thickness of 5 nm.

[2890] A second electron transport layer (ET) with a thickness of 25 nm was formed by co-evaporating compounds ET5 and Liq onto the first electron transport layer (HBL). The proportions of ET5 and Liq in the second electron transport layer (ET) were set to 50% by mass.

[2891] An electron injection layer with a thickness of 1 nm was formed by evaporating Liq onto the second electron transport layer.

[2892] A cathode with a film thickness of 80 nm was formed by evaporating metallic Al onto the electron injection layer.

[2893] The component configuration of Example 12 is shown in a simplified manner as follows.

[2894] ITO(130) / HT6: HA2(10, 97%: 3%) / HT6(80) / HT7(4) / PY3(1) / PY4: BD3(10, 98%: 2%) / BH4: BD3(15, 98%: 2%) / ET4(5) / ET5: Liq(25, 50%: 50%) / Liq(1) / Al(80)

[2895] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[2896] Similarly, within parentheses, the percentages (97% : 3%) represent the ratio (mass %) of compounds HT6 and HA2 in the hole injection layer, the percentages (98% : 2%) represent the ratio (mass %) of the host material (compound PY4 or compound BH4) and compound BD3 in the emissive layer, and the percentages (50% : 50%) represent the ratio (mass %) of compounds ET5 and Liq in the second electron transport layer (ET). The same notation applies hereinafter.

[2897] (Example 13)

[2898] The organic EL element of Example 13 was fabricated in the same manner as that of Example 12, except that the film thickness of the second hole transport layer, the first hole transport layer, and the first light-emitting layer were changed to the film thicknesses listed in Table 11.

[2899] (Comparative Example 17)

[2900] The organic EL element of Comparative Example 17 was fabricated in the same manner as in Example 12, except that the thickness of the second hole transport layer was changed to the thickness described in Table 11, and a first light-emitting layer was formed directly connected to the second hole transport layer instead of forming a first hole transport layer.

[2901] (Comparative Example 18)

[2902] The organic EL element of Comparative Example 18 was fabricated in the same manner as in Example 12, except that, as shown in Table 11, a third hole transport layer was not formed, a second hole transport layer with a thickness of 80 nm was formed by evaporating compound PY2 after the formation of the hole injection layer, and a first hole transport layer with a thickness of 5 nm was formed by evaporating compound PY3 after the formation of the second hole transport layer.

[2903] Table 11

[2904]

[2905] (Example 14)

[2906] A glass substrate (manufactured by Geomatec Corporation) with an ITO (Indium Tin Oxide) transparent electrode (anode) and a thickness of 25mm×75mm×1.1mm was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was set to 130nm.

[2907] The cleaned glass substrate with transparent electrode lines was mounted on the substrate holder of the vacuum evaporation apparatus. First, compound HA3 was deposited on the side with transparent electrode lines to cover the transparent electrode, thus forming a hole injection layer with a film thickness of 5 nm.

[2908] Following the formation of the hole injection layer, a third hole transport layer with a thickness of 80 nm was formed by vapor deposition of compound HT8.

[2909] Following the formation of the third hole transport layer, a second hole transport layer with a thickness of 7.5 nm was formed by vapor deposition of compound HT9.

[2910] Following the formation of the second hole transport layer, the compound PY6 was evaporated to form the first hole transport layer with a thickness of 2.5 nm.

[2911] Compound PY6 (host material) and compound BD1 (dopant material) were co-deposited on the first hole transport layer, with compound BD1 accounting for 2% by mass, to form a first light-emitting layer with a thickness of 7.5 nm.

[2912] Compound BH1 (host material) and compound BD1 (dopant material) were co-deposited on the first luminescent layer, with the proportion of compound BD1 being 2% by mass, to form a second luminescent layer with a film thickness of 17.5 nm.

[2913] An electron transport layer (also known as a hole blocking layer) with a thickness of 10 nm was formed by evaporating compound ET3 onto the second light-emitting layer.

[2914] An electron injection layer with a thickness of 1 nm was formed by evaporating LiF onto the electron transport layer (HBL).

[2915] A cathode with a film thickness of 80 nm was formed by evaporating metallic Al onto the electron injection layer.

[2916] The simplified component configuration of Example 14 is shown below.

[2917] ITO(130) / HA3(5) / HT8(80) / HT9(7.5) / PY6(2.5) / PY6: BD1(7.5, 98%: 2%) / BH1: BD1(17.5, 98%: 2%) / ET3(10) / LiF(1) / Al(80)

[2918] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[2919] Similarly, within parentheses, the percentage figures (98% : 2%) represent the ratio (mass %) of the host material (compound PY6 or compound BH1) and compound BD1 in the first or second luminescent layer. The same notation will be used below.

[2920] (Example 15)

[2921] The organic EL element of Example 15 was fabricated in the same manner as in Example 14, except that the thickness of the second hole transport layer and the thickness of the first hole transport layer were changed to the thicknesses listed in Table 12 to form the second hole transport layer and the first hole transport layer.

[2922] (Comparative Example 19)

[2923] The organic EL element of Comparative Example 19 was fabricated in the same manner as in Example 14, except that the thickness of the second hole transport layer was changed to the thickness described in Table 12, and a first light-emitting layer was formed directly connected to the second hole transport layer instead of forming a first hole transport layer.

[2924] (Comparative Example 20)

[2925] The organic EL element of Comparative Example 20 was fabricated in the same manner as in Example 14, except that a third hole transport layer and a second hole transport layer were not formed, and the first hole transport layer was changed to the film thickness described in Table 12 after the formation of the hole injection layer.

[2926] Table 12

[2927]

[2928] (Example 16)

[2929] A glass substrate (manufactured by Geomatec Corporation) with an ITO (Indium Tin Oxide) transparent electrode (anode) and a thickness of 25mm×75mm×1.1mm was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was set to 130nm.

[2930] The cleaned glass substrate with transparent electrode lines was mounted on the substrate holder of the vacuum evaporation apparatus. First, compound HA3 was deposited on the side with transparent electrode lines to cover the transparent electrode, thus forming a hole injection layer with a film thickness of 5 nm.

[2931] Following the formation of the hole injection layer, a third hole transport layer with a thickness of 80 nm was formed by vapor deposition of compound HT8.

[2932] Following the formation of the third hole transport layer, the compound HT9 was vapor-deposited to form a second hole transport layer with a thickness of 5 nm.

[2933] Following the formation of the second hole transport layer, the compound PY7 was evaporated to form the first hole transport layer with a thickness of 5 nm.

[2934] Compound PY7 (host material) and compound BD1 (dopant material) were co-deposited on the first hole transport layer, with compound BD1 accounting for 2% by mass, to form a first light-emitting layer with a thickness of 12.5 nm.

[2935] A second emitting layer with a thickness of 12.5 nm was formed by co-evaporating compounds BH5, BH6 (host material), and BD1 (dopant material) onto the first emitting layer. The proportions of compound BH5, compound BH6, and compound BD1 in the second emitting layer were set to 58.8% by mass, 39.2% by mass, and 2% by mass.

[2936] An electron transport layer (also known as a hole blocking layer) with a thickness of 10 nm was formed by evaporating compound ET3 onto the second light-emitting layer.

[2937] An electron injection layer with a thickness of 1 nm was formed by evaporating LiF onto the electron transport layer (HBL).

[2938] A cathode with a film thickness of 80 nm was formed by evaporating metallic Al onto the electron injection layer.

[2939] The simplified component configuration of Embodiment 16 is shown below.

[2940] ITO(130) / HA3(5) / HT8(80) / HT9(5) / PY7(5) / PY7:BD1(12.5,98%:2%) / BH5:BH6:BD1(12.5,58.8%:39.2%:2%) / ET3(10) / LiF(1) / Al(80)

[2941] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[2942] Similarly, within parentheses, the percentages (98% : 2%) represent the proportion (mass %) of the host material (compound PY7) and compound BD1 in the first luminescent layer, and the percentages (58.8% : 39.2% : 2%) represent the proportion (mass %) of compounds BH5, BH6, and BD1 in the second luminescent layer. The same notation will be used below.

[2943] (Example 17)

[2944] The organic EL element of Example 17 was fabricated in the same manner as in Example 16, except that the thickness of the second hole transport layer and the thickness of the first hole transport layer were changed to the thicknesses listed in Table 13 to form the second hole transport layer and the first hole transport layer.

[2945] (Comparative Example 21)

[2946] The organic EL element of Comparative Example 21 was fabricated in the same manner as in Example 16, except that the thickness of the second hole transport layer was changed to the thickness described in Table 13, and a first light-emitting layer was formed directly connected to the second hole transport layer instead of forming a first hole transport layer.

[2947] (Comparative Example 22)

[2948] The organic EL element of Comparative Example 22 was fabricated in the same manner as in Example 16, except that a third hole transport layer and a second hole transport layer were not formed, and the first hole transport layer was changed to the film thickness described in Table 13 after the formation of the hole injection layer.

[2949] Table 13

[2950]

[2951] <Compound Evaluation>

[2952] (Preparation of toluene solution)

[2953] Compound BD1 was prepared at 4.9 × 10⁻⁶. -6 A toluene solution of compound BD1 was prepared by dissolving it in toluene at a concentration of mol / L.

[2954] The toluene solutions of compound BD2 and compound BD3 were prepared in the same manner as compound BD1.

[2955] (Determination of the maximum peak wavelength of fluorescence emission (FL-peak))

[2956] The maximum peak wavelength of fluorescence emission when a toluene solution of compound BD1, compound BD2, or compound BD3 is excited at 390 nm was measured using a fluorescence spectroscopy apparatus (F-7000 spectrophotometer (Hitachi High Technology Scientific Co., Ltd.)).

[2957] The maximum peak wavelength of fluorescence emission of compound BD1 is 453 nm.

[2958] The maximum peak wavelength of fluorescence emission of compound BD2 is 450 nm.

[2959] The maximum peak wavelength of fluorescence emission of compound BD3 is 455 nm.

[2960] Symbol Explanation

[2961] 1…Organic EL element, 1A…Organic EL element, 2…Substrate, 3…Anode, 4…Cathode, 5…Light-emitting layer, 6…Hole injection layer, 71…First hole transport layer, 72…Second hole transport layer, 8…Electron transport layer, 9…Electron injection layer, 10…Organic layer, 10A…Organic layer.

Claims

1. An organic electroluminescent element, comprising: anode, cathode, A light-emitting layer disposed between the anode and the cathode, A first hole transport layer disposed between the anode and the light-emitting layer, and A second hole transport layer is configured between the anode and the first hole transport layer. The first hole transport layer is directly adjacent to the light-emitting layer. The first hole transport layer comprises a first compound represented by the following general formula (1). The first compound has at least one group represented by the following general formula (11), The second hole transport layer is directly adjacent to the first hole transport layer. The second hole transport layer contains compounds having only one amino group in their molecules. In the general formula (1), R 101 ~R 110 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or The group represented by the general formula (11), in, R 101 ~R 110 At least one of them is a group represented by the general formula (11). When there are multiple groups represented by the general formula (11), the multiple groups represented by the general formula (11) may be the same as or different from each other. L 101 for single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 101 for Substituted or unsubstituted pyrene group, mx is 0, 1, 2, 3, 4, or 5. In L 101 When there are more than two, more than two L 101 They are the same or different. In Ar 101 In the case of two or more Ar, two or more Ar 101 They are the same or different. In the general formula (11), * indicates the bonding position with the pyrene ring in the general formula (1). In the first compound, the substituents described as "substituted or unsubstituted" are selected from... Unsubstituted alkyl groups with 1 to 50 carbon atoms Unsubstituted alkenyl groups with 2 to 50 carbon atoms Unsubstituted acetylinyl groups with 2 to 50 carbon atoms Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 )(R 902 )(R 903 )、 -O-(R 904 )、 -S-(R 905 )、 Halogen atoms, cyano, Nitro, Unsubstituted aryl groups with 6 to 50 carbon atoms, and At least one group from the group consisting of unsubstituted heterocyclic groups having 5 to 50 cyclic atoms. In the first compound represented by general formula (1), R 901 R 902 R 903 R 904 R 905 R 801 and R 802 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different. In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different. In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different. In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different. In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different. In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different. In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.

2. The organic electroluminescent element according to claim 1, wherein, The compound having only one amino group in its molecule is N-(L AMN1 -L AMN2 -L AMN3 -Ar AMN )3, Multiple L AMN1 L AMN2 L AMN3 Ar AMN They can be the same or different. L AMN1 L AMN2 L AMN3 It is a single bond, a substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group. Ar AMN For substituted or unsubstituted aryl groups, or substituted or unsubstituted heterocyclic groups, L AMN1 L AMN2 L AMN3 Ar AMN It does not contain pyrene structures.

3. The organic electroluminescent element according to claim 1, wherein, The second hole transport layer contains a compound represented by the following general formula (B1). In the general formula (B1), L A1 L B1 and L C1 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 18 carbon atoms, or Divalent heterocyclic groups with 5 to 13 cyclic atoms, substituted or unsubstituted. In L A1 and L B1 In the case of a single bond, A1 and B1 They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. In L A1 and L C1 In the case of a single bond, A1 and C1 They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. In L B1 and L C1 In the case of a single bond, B1 and C1 They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. A1, B1, and C1, which do not form the substituted or unsubstituted monocyclic rings and do not form the substituted or unsubstituted fused rings, are each independently […]. Substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms, or -Si(R 921 (R) 922 (R) 923 The group shown in the figure, R 921 R 922 and R 923 Each is independently a substituted or unsubstituted aryl group with 6 to 30 carbon atoms in a cyclic formation. In R 921 In the case of multiple Rs, multiple Rs 921 They are the same or different. In R 922 In the case of multiple Rs, multiple Rs 922 They are the same or different. In R 923 In the case of multiple Rs, multiple Rs 923 They are the same or different.

4. The organic electroluminescent element according to claim 1, wherein, The second hole transport layer contains a compound with a carbazole group.

5. The organic electroluminescent element according to claim 4, wherein, The compound having a carbazole group is Cz-(L CZ1 -L CZ2 -L CZ3 -Ar CZ )1、 Cz-(L CZ1 -L CZ2 -L CZ3 -Ar CZ )2, or Cz-(L CZ1 -L CZ2 -L CZ3 -Ar CZ )3, Cz is a carbazolium group. Multiple L CZ1 L CZ2 L CZ3 Ar CZ They can be the same or different. L CZ1 Bonded to carbon or nitrogen atoms of Cz, L CZ1 L CZ2 L CZ3 It is a single bond, a substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group. Ar CZ For substituted or unsubstituted aryl groups, or substituted or unsubstituted heterocyclic groups, L CZ1 L CZ2 L CZ3 Ar CZ It does not contain pyrene structures.

6. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The second hole transport layer is formed only by compounds that do not contain a pyrene structure.

7. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The second hole transport layer is formed only by compounds containing amino groups.

8. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first hole transport layer and the second hole transport layer do not contain antimony chloride, vanadium oxide, molybdenum oxide, ruthenium oxide, tungsten oxide, zinc oxide, tin oxide, or iron oxide.

9. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first hole transport layer and the second hole transport layer do not contain inorganic compounds.

10. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first hole transport layer and the second hole transport layer do not contain hexacyanoazinabenzophenanthrene.

11. The organic electroluminescent element according to any one of claims 1 to 5, wherein, It has a third hole transport layer that is directly connected to the anode side of the second hole transport layer.

12. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The thickness of the first hole transport layer is less than 15 nm.

13. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The thickness of the first hole transport layer is 2 nm or more.

14. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The thickness of the first hole transport layer is greater than 2 nm and less than 10 nm.

15. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The thickness of the first hole transport layer is greater than 2 nm and less than 5 nm.

16. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The organic electroluminescent element emits light with a maximum peak wavelength of 430 nm or higher and 480 nm or lower when the element is driven.

17. The organic electroluminescent element according to claim 1, wherein, The light-emitting layer contains a second compound and a third compound. The third compound is the host material, and the second compound is the dopant material.

18. The organic electroluminescent element according to claim 17, wherein, The third compound is the compound represented by the general formula (1) above. The compound represented by general formula (1) as the first compound may be the same as or different from the compound represented by general formula (1) as the third compound.

19. The organic electroluminescent element according to claim 17, wherein, The third compound is a compound represented by the following general formula (2). In the general formula (2), R 201 ~R 208 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. L 201 and L 202 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 201 and Ar 202 Each independently Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the third compound, R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different. In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different. In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different. In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different. In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different. In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different. In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different. In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different. In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.

20. The organic electroluminescent element according to claim 17, wherein, The singlet state energy S1(H3) of the third compound and the singlet state energy S1(D2) of the second compound satisfy the following mathematical equation 1: S1(H3)>S1(D2)…Mathematical formula 1.

21. The organic electroluminescent element according to claim 20, wherein, 10 compounds prepared for singlet energy determination -5 mol / L or higher and 10 -4 A toluene solution with a concentration below mol / L was added to a quartz cuvette, and the absorption spectrum of the sample was measured at 300 K. A downward-sloping tangent was drawn on the longer wavelength side of the absorption spectrum. The wavelength value λedge at the intersection of this tangent and the horizontal axis was substituted into the conversion formula F2 shown later to calculate the singlet energy. Here, the vertical axis represents absorption intensity, the horizontal axis represents wavelength, λedge is in nm, and S1 is in eV. Conversion formula F2: S1 = 1239.85 / λedge.

22. The organic electroluminescent element according to claim 1, wherein, The light-emitting layer also contains a second compound with fluorescent properties. The second compound is a compound that exhibits luminescence with a maximum peak wavelength of 430 nm or higher and 480 nm or lower.

23. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The light-emitting layer contains a pyrene derivative.

24. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The light-emitting layer contains anthracene derivatives.

25. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The light-emitting layer does not contain phosphorescent materials.

26. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The luminescent layer does not contain heavy metal complexes or phosphorescent rare earth metal complexes.

27. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The light-emitting layer does not contain metal complexes.

28. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The light-emitting layer includes a first light-emitting layer and a second light-emitting layer disposed between the first light-emitting layer and the cathode.

29. The organic electroluminescent element according to claim 28, wherein, The first hole transport layer is directly connected to the first light-emitting layer.

30. The organic electroluminescent element according to claim 28, wherein, The first light-emitting layer and the second light-emitting layer are directly connected.

31. The organic electroluminescent element according to claim 28, wherein, The first light-emitting layer contains a pyrene derivative. The second light-emitting layer contains anthracene derivatives.

32. The organic electroluminescent element according to claim 31, wherein, The pyrene derivative contained in the first light-emitting layer is the main material of the first light-emitting layer. The anthracene derivative contained in the second light-emitting layer is the main material of the second light-emitting layer.

33. The organic electroluminescent element according to claim 28, wherein, The first luminescent layer and the second luminescent layer each independently contain a fluorescent compound.

34. The organic electroluminescent element according to claim 28, wherein, The first luminescent layer contains a third compound and a second compound with fluorescent properties.

35. The organic electroluminescent element according to claim 34, wherein, The third compound is the host material, and the second compound is the dopant material.

36. The organic electroluminescent element according to claim 34, wherein, The third compound is the compound represented by the general formula (1). The compound represented by general formula (1) as the first compound may be the same as or different from the compound represented by general formula (1) as the third compound.

37. The organic electroluminescent element according to claim 28, wherein, The second luminescent layer contains a fifth compound and a fourth compound that exhibits fluorescence.

38. The organic electroluminescent element according to claim 37, wherein, The fifth compound is the host material, and the fourth compound is the dopant material.

39. The organic electroluminescent element according to claim 37, wherein, The fifth compound is a compound represented by the following general formula (2). In the general formula (2), R 201 ~R 208 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. L 201 and L 202 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 201 and Ar 202 Each independently Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the fifth compound, R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different. In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different. In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different. In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different. In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different. In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different. In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different. In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different. In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.

40. The organic electroluminescent element according to claim 33, wherein, The first and second light-emitting layers contain fluorescent compounds that exhibit luminescence with a maximum peak wavelength of 430 nm or higher and 480 nm or lower.

41. The organic electroluminescent element according to claim 28, wherein, The first and second light-emitting layers do not contain phosphorescent materials.

42. The organic electroluminescent element according to claim 28, wherein, The first luminescent layer and the second luminescent layer do not contain heavy metal complexes or phosphorescent rare earth metal complexes.

43. The organic electroluminescent element according to claim 28, wherein, Neither the first light-emitting layer nor the second light-emitting layer contains metal complexes.

44. The organic electroluminescent element according to any one of claims 17, 22, 34, and 37, wherein, In the presence of a second compound or a fourth compound, the second compound or the fourth compound is each independently one or more compounds selected from the group consisting of compounds represented by general formula (3), general formula (4), general formula (5), general formula (6), general formula (7), general formula (8), general formula (9), and general formula (10). In the general formula (3), R 301 ~R 310 One or more of the groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R 301 ~R 310 At least one of them is a monovalent group represented by the following general formula (31), R that does not form the above-mentioned monocyclic ring, does not form the above-mentioned fused ring, and is not a monovalent group represented by the following general formula (31) 301 ~R 310 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the general formula (31), Ar 301 and Ar 302 Each independently Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. L 301 ~L 303 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted. * indicates the bonding position in the pyrene ring in the above general formula (3). In the general formula (4), Z can be independently represented by CRa or nitrogen atoms. Rings A1 and A2 are each independent of each other. Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted. When there are multiple Ra, one or more groups consisting of two or more adjacent Ra are selected. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. n21 and n22 are each independently 0, 1, 2, 3 or 4. When there are multiple Rb, one or more groups consisting of two or more adjacent Rb are considered. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. When there are multiple Rc, one or more groups are formed by two or more adjacent Rc. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. Ra, Rb, and Rc, which do not form the aforementioned single rings and do not form the aforementioned fused rings, are each independently... Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the general formula (5), R 501 ~R 507 and R 511 ~R 517 One or more of the groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R that does not form the aforementioned single ring and does not form the aforementioned fused ring 501 ~R 507 and R 511 ~R 517 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. R 521 and R 522 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the general formula (6), Rings a, b, and c are each independently... Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted. R 601 and R 602 Each ring independently bonds to the aforementioned a-ring, b-ring, or c-ring to form a substituted or unsubstituted heterocycle, or not to form a substituted or unsubstituted heterocycle. R does not form the aforementioned substituted or unsubstituted heterocycles 601 and R 602 Each independently Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the general formula (7), The r-ring is a ring shown in the above general formula (72) or general formula (73) that is fused at any position of adjacent rings. The q-ring and s-ring are each independently rings fused at any position of adjacent rings as shown in the above general formula (74). The p-ring and t-ring are each independently structures shown in the above general formula (75) or general formula (76) that are fused at any position of adjacent rings. X7 represents an oxygen atom, a sulfur atom, or NR. 702 , In R 701 In the case of multiple R, multiple adjacent R 701 They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R that does not form the aforementioned single ring and does not form the aforementioned fused ring 701 and R 702 Each independently Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 701 and Ar 702 Each independently Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. L 701 for Substituted or unsubstituted alkylene groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted ynylene groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkylene groups with 3 to 50 carbon atoms Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. m1 is 0, 1, or 2. m2 can be 0, 1, 2, 3, or 4. m3 can be independently 0, 1, 2 or 3. Each m4 is independently 0, 1, 2, 3, 4, or 5. In R 701 In the case of multiple Rs, multiple Rs 701 They are the same or different. When multiple X7s exist, they may be identical or different from each other. In R 702 In the case of multiple Rs, multiple Rs 702 They are the same or different. In Ar 701 In the case of multiple instances, multiple Ar 701 They are the same or different. In Ar 702 In the case of multiple instances, multiple Ar 702 They are the same or different. In L 701 In the case of multiple Ls, multiple Ls 701 They are the same or different. In the general formula (8), R 801 With R 802 R 802 With R 803 and R 803 With R 804 At least one group of the groups are bonded to each other to form the divalent groups shown in the following general formula (82), or they are not bonded to each other. R 805 With R 806 R 806 With R 807 and R 807 With R 808 At least one group of the groups are bonded to each other to form the divalent group shown in the following general formula (83), or they are not bonded to each other. R that does not form the divalent group shown in the above general formula (82) 801 ~R 804 and R 811 ~R 814 At least one of them is a monovalent group represented by the following general formula (84), R that does not form the divalent group shown in the above general formula (83) 805 ~R 808 and R 821 ~R 824 At least one of them is a monovalent group represented by the following general formula (84), X8 is CR 81 R 82 oxygen atom, sulfur atom or NR 809 , By R 81 and R 82 Groups They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R that does not form the divalent groups shown in general formulas (82) and (83) above, and does not form the monovalent groups shown in general formula (84) above. 801 ~R 808 R that is not a monovalent group as shown in the above general formula (84) 811 ~R 814 and R 821 ~R 824 R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 81 and R 82 and R 809 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the general formula (84), Ar 801 and Ar 802 Each independently Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. L 801 ~L 803 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms Substituted or unsubstituted divalent heterocyclic groups with 5 to 30 cyclic atoms, or A divalent linker is formed by bonding 2 to 4 groups from the group consisting of a substituted or unsubstituted aryl group with 6 to 30 carbon atoms and a substituted or unsubstituted divalent heterocyclic group with 5 to 30 carbon atoms. In the above general formula (84), * indicates the bonding position with the ring structure shown in general formula (8), or the group shown in general formula (82) or general formula (83). In the general formula (9), A 91 Ring and A 92 Each ring is independent of the others. Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted. Selected from A 91 Ring and A 92 One or more rings in a ring *bonding with the structure shown in the following general formula (92), In the general formula (92), A 93 Ring for Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted. X9 is NR 93 C(R) 94 (R) 95 ), Si(R) 96 (R) 97 ), Ge(R) 98 (R) 99 ), oxygen atoms, sulfur atoms or selenium atoms, R 91 and R 92 They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R that does not form the aforementioned single ring and does not form the aforementioned fused ring 91 and R 92 and R 93 ~R 99 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the general formula (10), Ax1 ring is a ring as shown in the above general formula (10a) that is fused at any position of adjacent rings. Ax2 ring is a ring of the above general formula (10b) that is fused at any position between adjacent rings. The two asterisks in the above general formula (10b) are bonded to any position of the Ax3 ring. X A and X B Each independently is C(R) 1003 (R) 1004 ), Si(R) 1005 (R) 1006 ), oxygen atom or sulfur atom, Ax3 ring is Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 1001 for Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. R 1001 ~R 1006 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. mx1 is 3, mx2 is 2. Multiple R 1001 They are the same or different. Multiple R 1002 They are the same or different. ax is 0, 1, or 2. When ax is 0 or 1, the structures within the parentheses shown in "3-ax" are either identical or different. When ax = 2, multiple Ar 1001 They are the same or different. In the second compound or the fourth compound, R 901 R 902 R 903 R 904 R 905 R 906 and R 907 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different. In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different. In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different. In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different. In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different. In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different. In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.

45. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The substituents expressed as "substituted or unsubstituted" in the various formulas are Unsubstituted alkyl groups with 1 to 50 carbon atoms Unsubstituted aryl groups with 6 to 50 carbon atoms, or Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms.

46. ​​The organic electroluminescent element according to any one of claims 1 to 5, wherein, The substituents expressed as "substituted or unsubstituted" in the various formulas are Unsubstituted alkyl groups having 1 to 18 carbon atoms Unsubstituted aryl groups with 6 to 18 carbon atoms, or Unsubstituted heterocyclic groups with 5 to 18 cyclic atoms.

47. The organic electroluminescent element according to claim 22 or 40, wherein, The method for determining the maximum peak wavelength of a compound is as follows: 10 μm of the compound to be measured is prepared... -6 mol / L or higher and 10 -5 A toluene solution with a concentration of less than mol / L was added to a quartz cuvette, and the emission spectrum of the sample was measured at 300K. The peak wavelength of the emission spectrum with the highest emission intensity was taken as the maximum emission peak wavelength, where the vertical axis represents the emission intensity and the horizontal axis represents the wavelength.

48. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The heterocyclic group in the first compound is a group containing at least one of oxygen or sulfur atoms.

49. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first hole transport layer does not contain compounds with amino groups.

50. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first hole transport layer does not contain compounds containing nitrogen and boron atoms.

51. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The group represented by general formula (11) is the group represented by the following general formula (111). In the general formula (111), X1 is CR 123 R 124 oxygen atom, sulfur atom or NR 125 , L 111 and L 112 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. ma can be 0, 1, 2, 3, or 4. mb can be 0, 1, 2, 3, or 4. ma + mb can be 0, 1, 2, 3, or 4. Ar 101 Ar in the general formula (11) 101 Same meaning R 121 R 122 R 123 R 124 and R 125 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. mc is 3. 3 Rs 121 They are the same or different. md is 3 3 Rs 122 They are the same or different.

52. The organic electroluminescent element according to claim 51, wherein, The group represented by the general formula (111) is represented by the following general formula (111b). In the general formula (111b), X1, L 111 L 112 ma, mb, Ar 101 R 121 R 122 R 123 R 124 and R 125 Each independently relates to X1 and L in the above general formula (111). 111 L 112 ma, mb, Ar 101 R 121 R 122 R 123 R 124 and R 125 Same meaning Multiple R 121 They are the same or different. Multiple R 122 They are the same or different.

53. The organic electroluminescent element according to claim 51, wherein, ma is 0, 1, or 2. mb can be 0, 1, or 2.

54. The organic electroluminescent element according to claim 51, wherein, ma is 0 or 1. mb is 0 or 1.

55. The organic electroluminescent element according to claim 51, wherein, The group represented by the general formula (111) is represented by the following general formula (111c). In the general formula (111c), X1, L 112 ,mc,md,Ar 101 R 121 and R 122 Each independently relates to X1 and L in the above general formula (111). 112 ,mc,md,Ar 101 R 121 and R 122 They have the same meaning.

56. The organic electroluminescent element according to claim 51, wherein, The group represented by the general formula (111) is represented by the following general formula (111d). In the general formula (111d), L 111 L 112 ,ma,mb,ma+mb,Ar 101 R 121 R 122 R 123 R 124 R 125 The definitions of mc and md are the same as those in the above general formula (111).

57. The organic electroluminescent element according to claim 56, wherein, R 123 With R 124 They do not bond with each other.

58. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first compound is represented by the following general formula (101), In the general formula (101), R 101 ~R 120 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Among them, R 101 ~R 110 One of them represents L 101 The bonding position, R 111 ~R 120 One of them represents L 101 The bonding position, L 101 for single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. mx is 0, 1, 2, 3, 4, or 5. In L 101 When there are more than two, more than two L 101 They are the same or different.

59. The organic electroluminescent element according to claim 58, wherein, The compound represented by general formula (101) is represented by the following general formula (101A). In the general formula (101A), R 101 R 102 R 104 ~R 119 L 101 And mx are respectively related to R in the above general formula (101) 101 R 102 R 104 ~R 119 L 101 It has the same meaning as mx.

60. The organic electroluminescent element according to any one of claims 1 to 5, wherein, L 101 for single key, or A substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.

61. The organic electroluminescent element according to claim 58, wherein, The first compound is represented by the following general formula (102), In the general formula (102), R 101 ~R 120 Each independently relates to R in the general formula (101) 101 ~R 120 Same meaning Among them, R 101 ~R 110 One of them represents L 111 The bonding position, R 111 ~R 120 One of them represents L 112 The bonding position, X1 is CR 123 R 124 oxygen atom, sulfur atom or NR 125 , L 111 and L 112 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. ma can be 0, 1, 2, 3, or 4. mb can be 0, 1, 2, 3, or 4. ma + mb can be 0, 1, 2, 3, or 4. R 121 R 122 R 123 R 124 and R 125 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. mc is 3. 3 Rs 121 They are the same or different. md is 3 3 Rs 122 They are the same or different.

62. The organic electroluminescent element according to claim 61, wherein, ma is 0, 1, or 2. mb can be 0, 1, or 2.

63. The organic electroluminescent element according to claim 61, wherein, ma is 0 or 1. mb is 0 or 1.

64. The organic electroluminescent element according to claim 51, wherein, L 111 and L 112 At least one of them is Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or A divalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

65. The organic electroluminescent element according to any one of claims 1 to 5, wherein, R 101 ~R 110 Two or more of them are groups represented by the general formula (11).

66. The organic electroluminescent element according to claim 65, wherein, L 101 It is neither a replaced nor unreplaced pyrene group. R, as a group not represented by the general formula (11) 101 ~R 110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is not a substituted or unsubstituted pyrene group.

67. The organic electroluminescent element according to any one of claims 1 to 5, wherein, R is not the group represented by the general formula (11) 101 ~R 110 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

68. The organic electroluminescent element according to any one of claims 1 to 5, wherein, R is not the group represented by the general formula (11) 101 ~R 110 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or Cycloalkyl groups, substituted or unsubstituted, having 3 to 50 carbon atoms.

69. The organic electroluminescent element according to any one of claims 1 to 5, wherein, R is not the group represented by the general formula (11) 101 ~R 110 It is a hydrogen atom.

70. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first compound in the first hole transport layer has a content of 90% by mass or more.

71. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first compound in the first hole transport layer has a content of 99% by mass or more.

72. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first hole transport layer is formed solely from the first compound.

73. The organic electroluminescent element according to any one of claims 1 to 5, wherein, In the first compound, the substituents described as "substituted or unsubstituted" do not contain substituted or unsubstituted pyrene groups.

74. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first compound is a compound that has only one pyrene ring in its molecule.

75. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first compound is a compound that has only two pyrene rings in its molecule.

76. The organic electroluminescent element according to any one of claims 1 to 5, wherein, In the first compound, all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

77. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first hole transport layer does not emit light with a maximum peak wavelength of 430nm or higher and 480nm or lower when the device is driven.

78. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first compound is any one of the following compounds PY1 to PY6. 。 79. The organic electroluminescent element according to any one of claims 1 to 5, wherein, An electron transport layer is provided between the cathode and the light-emitting layer.

80. An electronic device comprising the organic electroluminescent element according to any one of claims 1 to 79.

Images