Organic electroluminescent elements and electronic devices

Abstract

An organic electroluminescent element (1) having a light-emitting layer (5) between an anode and a cathode, having a first layer (71) between the cathode and the light-emitting layer (5), the first layer (71) having a thickness of 50 nm or more, the first layer (71) containing a compound of the following general formula (1), in which A is a fused aryl group with 13 or more and 50 or less of substituted or unsubstituted cyclic carbons, or a fused heterocyclic group with 14 or more and 50 or less of substituted or unsubstituted cyclic atoms. It should be noted that the first layer (71) does not contain metal doping materials.

Description

Technical Field

[0001] This invention relates to organic electroluminescent elements and electronic devices. Background Technology

[0002] Organic electroluminescent devices (hereinafter sometimes referred to as "organic EL devices") are used in full-color displays for mobile phones, televisions, and other applications. When a voltage is applied to an organic EL device, holes are injected from the anode into the emitting layer, and electrons are injected from the cathode into the emitting layer. Then, in the emitting layer, the injected holes recombine with the electrons to form excitons. At this point, according to the statistical rules of electron spin, singlet excitons are generated at a rate of 25%, and triplet excitons at a rate of 75%.

[0003] To improve the performance of organic EL devices, various studies have been conducted on the compounds used in organic EL devices and the structures of organic EL devices. Performance characteristics of organic EL devices include, for example, brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime.

[0004] For example, Patent Document 1 describes an embodiment of using a compound having an anthracene structure and a benzimidazole structure as an electron transport material for an organic EL element.

[0005] For example, Patent Document 2 describes examples of using compounds having anthracene and triazine structures, compounds having fluorene and triazine structures, etc., as electron transport materials for organic EL elements.

[0006] For example, Patent Document 3 describes an embodiment of using compounds having heteroaryl and triazine structures as electron transport materials for organic EL elements.

[0007] Existing technical documents

[0008] Patent documents

[0009] Patent Document 1: International Publication No. 2010 / 134350

[0010] Patent Document 2: International Publication No. 2019 / 163824

[0011] Patent Document 3: International Publication No. 2019 / 163825 Summary of the Invention

[0012] The problem the invention aims to solve

[0013] The object of the present invention is to provide an organic electroluminescent element that can be driven at low voltage even when there is no active metal doping in the electron transport material in the thick film electron transport region, and an electronic device equipped with the organic electroluminescent element.

[0014] means for solving problems

[0015] According to one aspect of the present invention, an organic electroluminescent element is provided, which is an organic electroluminescent element having a light-emitting layer between an anode and a cathode, wherein a first layer is provided between the cathode and the light-emitting layer, the thickness of the first layer is 50 nm or more, and the first layer contains a compound of the following general formula (100). It should be noted that the first layer does not contain metal doping materials.

[0016]

Chemical Formula 1

[0017]

[0018] (In the above general formula (100),

[0019] A is

[0020] Substituted or unsubstituted fused aryl groups with 13 or more but less than 50 cyclic carbons, or

[0021] Fused heterocyclic groups with 14 or more but less than 50 cyclic atoms, whether substituted or unsubstituted.

[0022] L A for

[0023] single bond,

[0024] Substituted or unsubstituted arylene groups with 6 or more but less than 30 carbon atoms in the cyclic group, or

[0025] A divalent heterocyclic group, with 5 or more but less than 30 cyclic atoms, whether substituted or unsubstituted.

[0026] X1, X2, and X3 are each independently nitrogen atoms or CR3.

[0027] X P It is a nitrogen atom or CR1.

[0028] X Q It is a nitrogen atom or CR2.

[0029] It should be noted that X1, X2, X3, X P and X Q One or more of them are nitrogen atoms.

[0030] One or more groups consisting of two or more adjacent elements from R1, R2, and R3.

[0031] They bond together to form substituted or unsubstituted monocyclic rings.

[0032] They bond together to form substituted or unsubstituted fused rings, or

[0033] They do not bond with each other.

[0034] R1, R2, and R3, 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 […].

[0035] hydrogen atom,

[0036] Substituted or unsubstituted aryl groups with 6 or more but less than 30 carbon atoms in the cyclic group, or

[0037] Heterocyclic groups with 5 or more but less than 30 cyclic atoms, whether substituted or unsubstituted.

[0038] In the case of multiple R3s, these R3s may be identical or different from each other.

[0039] According to one aspect of the present invention, an organic electroluminescent element is provided, which is an organic electroluminescent element having a light-emitting layer between an anode and a cathode, wherein a first layer is provided between the cathode and the light-emitting layer, the thickness of the first layer is 50 nm or more, and the first layer contains a compound of the following general formula (1). It should be noted that the first layer does not contain metal doping materials.

[0040]

Chemical Formula 2

[0041]

[0042] (In the above general formula (1),

[0043] A is

[0044] Substituted or unsubstituted fused aryl groups with 13 or more but less than 50 cyclic carbons, or

[0045] Fused heterocyclic groups with 14 or more but less than 50 cyclic atoms, whether substituted or unsubstituted.

[0046] L A for

[0047] single bond,

[0048] Substituted or unsubstituted arylene groups with 6 or more but less than 30 carbon atoms in the cyclic group, or

[0049] A divalent heterocyclic group, with 5 or more but less than 30 cyclic atoms, whether substituted or unsubstituted.

[0050] X1, X2, and X3 are each independently nitrogen atoms or CR3.

[0051] It should be noted that more than one of X1, X2, and X3 is a nitrogen atom.

[0052] One or more groups consisting of two or more adjacent elements from R1, R2, and R3.

[0053] They bond together to form substituted or unsubstituted monocyclic rings.

[0054] They bond together to form substituted or unsubstituted fused rings, or

[0055] They do not bond with each other.

[0056] R1, R2, and R3, 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 […].

[0057] hydrogen atom,

[0058] Substituted or unsubstituted aryl groups with 6 or more but less than 30 carbon atoms in the cyclic group, or

[0059] Heterocyclic groups with 5 or more but less than 30 cyclic atoms, whether substituted or unsubstituted.

[0060] In the case of multiple R3s, these R3s may be identical or different from each other.

[0061] According to one aspect of the present invention, an electronic device incorporating an organic electroluminescent element according to one aspect of the present invention is provided.

[0062] According to one aspect of the present invention, an organic electroluminescent element that can be driven at low voltage even when no active metal is doped in the electron transport material of the thick-film electron transport region can be provided. Furthermore, according to another aspect of the present invention, an electronic device incorporating this organic electroluminescent element can be provided. Attached Figure Description

[0063] Figure 1 This diagram illustrates the general configuration of an example of an organic electroluminescent element according to one embodiment of the present invention.

[0064] Figure 2 This diagram illustrates the general configuration of an example of an organic electroluminescent element according to one embodiment of the present invention.

[0065] Figure 3 This diagram illustrates the general configuration of an example of an organic electroluminescent element according to one embodiment of the present invention.

[0066] Figure 4 This diagram illustrates the general configuration of an example of an organic electroluminescent element according to one embodiment of the present invention. Detailed Implementation

[0067] [definition]

[0068] In this specification, a hydrogen atom means an isotope containing different numbers of neutrons, namely protium, deuterium, and tritium.

[0069] 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.

[0070] 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.

[0071] 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.

[0072] 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.

[0073] 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.

[0074] 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.

[0075] In this specification, "unsubstituted ZZ group" means "substituted or unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".

[0076] 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.

[0077] 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.

[0078] Substituents described in this specification

[0079] The substituents described in this specification are explained below.

[0080] 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.

[0081] 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.

[0082] 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.

[0083] 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.

[0084] 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.

[0085] 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.

[0086] 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.

[0087] Unless otherwise specified 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.

[0088] 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.

[0089] • "Substituted or unsubstituted aryl groups"

[0090] 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.

[0091] "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.

[0092] • Unsubstituted aryl groups (specific example group G1A):

[0093] phenyl,

[0094] p-phenyl,

[0095] metaphenyl,

[0096] o-phenyl,

[0097] p-terphenyl-4-yl,

[0098] p-terphenyl-3-yl,

[0099] p-terphenyl-2-yl,

[0100] m-terphenyl-4-yl,

[0101] m-terphenyl-3-yl,

[0102] m-terphenyl-2-yl,

[0103] o-terphenyl-4-yl,

[0104] o-terphenyl-3-yl

[0105] o-terphenyl-2-yl,

[0106] 1-Naphthyl,

[0107] 2-Naphthyl,

[0108] anthracene,

[0109] Benzanthracene,

[0110] Fiki,

[0111] Benzphenanthrene,

[0112] Finadenyl,

[0113] Pyrene

[0114] base,

[0115] benzo[a] base,

[0116] Tri-phenylene,

[0117] Benzotrimethylene

[0118] phenylene,

[0119] Pentaphenyl,

[0120] Fluorine

[0121] 9,9'-spirobisfluorene,

[0122] benzo[f]fluorenyl,

[0123] Dibenzofluorene,

[0124] Fluoranthene base,

[0125] Benzofluoranthyl,

[0126] 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.

[0127]

Chemical Formula 3

[0128]

[0129] [Chemical Formula 4]

[0130]

[0131] • Substituted aryl groups (specific example group G1B):

[0132] o-Tolyl,

[0133] m-Tolyl,

[0134] p-Tolyl,

[0135] p-Xylyl,

[0136] m-Xylyl,

[0137] o-xylyl,

[0138] p-isopropylphenyl,

[0139] m-Isopropylphenyl,

[0140] o-isopropylphenyl,

[0141] p-tert-butylphenyl,

[0142] m-tert-butylphenyl,

[0143] o-tert-butylphenyl,

[0144] 3,4,5-Trimethylphenyl,

[0145] 9,9-Dimethylfluorenyl,

[0146] 9,9-Diphenylfluorenyl,

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

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

[0149] 9,9-Bis(4-tert-butylphenyl)fluorenyl,

[0150] cyanophenyl,

[0151] Triphenylsilylphenyl

[0152] Trimethylsilylphenyl

[0153] Phenynaphthyl,

[0154] 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.

[0155] • "Substituted or unsubstituted heterocyclic groups"

[0156] 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.

[0157] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.

[0158] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0159] 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".

[0160] "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.

[0161] 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).

[0162] 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).

[0163] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1):

[0164] pyrrole,

[0165] Imidazole group,

[0166] Pyrazolyl,

[0167] Triazole group,

[0168] Tetrazolyl,

[0169] Oxazolyl,

[0170] Isoxazolyl,

[0171] Oxadiazole group,

[0172] Thiazole group,

[0173] Isothiazolyl,

[0174] Thiadiazole group,

[0175] pyridyl,

[0176] pyridazinyl,

[0177] Pyrimidinyl,

[0178] Pyrazinyl,

[0179] Triazine group

[0180] Indole,

[0181] Isoindolyl,

[0182] Indazine group

[0183] Quinazine-based

[0184] Quinoline,

[0185] Isoquinoline,

[0186] Crenoline group

[0187] Phthaloazine

[0188] Quinazolinyl,

[0189] Quinoxaloyl,

[0190] Benzimidazole group,

[0191] Indazole group,

[0192] phenanthroline,

[0193] phenanthridine,

[0194] acridine group,

[0195] Phenazine group,

[0196] Carbazolyl,

[0197] Benzocarbazolyl,

[0198] Morpholinyl,

[0199] phenoxazine group,

[0200] phenothiazine group,

[0201] Azacarbazolyl and diazacarbazolyl.

[0202] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2):

[0203] furanyl,

[0204] Oxazolyl,

[0205] Isoxazolyl,

[0206] Oxadiazole group,

[0207] Xuton base,

[0208] Benzofuranyl,

[0209] Isobenzofuranyl,

[0210] Dibenzofuranyl,

[0211] Naphthobenzofuranyl,

[0212] Benzoxazolyl,

[0213] Benzisoxazole group,

[0214] phenoxazine group,

[0215] Morpholinyl,

[0216] Dinaphthylfuranyl,

[0217] Azadibenzofuranyl,

[0218] diazadibenzofuranyl,

[0219] Azanaphthobenzofuranyl and diazanaphthobenzofuranyl.

[0220] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3):

[0221] Thiophene group

[0222] Thiazole group,

[0223] Isothiazolyl,

[0224] Thiadiazole group,

[0225] benzothienyl

[0226] isobenzothienyl

[0227] dibenzothienyl

[0228] Naphthobenzothienyl

[0229] Benzothiazolyl,

[0230] Benzisothiazolyl,

[0231] phenothiazine group,

[0232] dinaphthothienyl

[0233] azadibenzothienyl

[0234] diazadibenzothienyl

[0235] Azanaphthobenzothienyl and diazanaphthobenzothienyl.

[0236] • 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):

[0237] [Chemical Formula 5]

[0238]

[0239]

Chemical Formula 6

[0240]

[0241] 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.

[0242] 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.

[0243] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1):

[0244] (9-phenyl)carbazole group,

[0245] (9-Biphenyl)carbazolyl,

[0246] (9-Phenyl)phenylcarbazolyl,

[0247] (9-Naphthyl)carbazole,

[0248] Diphenylcarbazole-9-yl,

[0249] Phenylexacarbazole-9-yl,

[0250] Methylbenzimidazole,

[0251] Ethylbenzimidazole,

[0252] Phenylacetyl,

[0253] Biphenyltriazine

[0254] diphenyltriazine group,

[0255] Phenylacetinyl and biphenylquinazolinyl.

[0256] • Heterocyclic groups containing oxygen atoms (specific example group G2B2):

[0257] Phenyl dibenzofuranyl,

[0258] Methyldibenzofuranyl,

[0259] tert-butyldibenzofuranyl and spiro[9H-xanton-9,9'-[9H]fluorene] monovalent residues.

[0260] • Heterocyclic groups containing sulfur atoms (specific example group G2B3):

[0261] Phenyl dibenzothiophene,

[0262] Methyldibenzothiophene,

[0263] The monovalent residues of tert-butyldibenzothiophene and spiro[9H-thiophene-9,9'-[9H]fluorene].

[0264] • 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):

[0265] 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.

[0266] • "Substituted or unsubstituted alkyl groups"

[0267] 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.

[0268] "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.

[0269] • Unsubstituted alkyl groups (specific example group G3A):

[0270] methyl,

[0271] Ethyl,

[0272] n-propyl,

[0273] Isopropyl,

[0274] n-Butyl,

[0275] Isobutyl,

[0276] Sec-butyl and tert-butyl.

[0277] • Substituted alkyl groups (specific example group G3B):

[0278] Heptafluoropropyl (including isomers),

[0279] Pentafluoroethyl,

[0280] 2,2,2-Trifluoroethyl and trifluoromethyl.

[0281] • "Substituted or unsubstituted alkenyl groups"

[0282] 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.

[0283] "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.

[0284] • Unsubstituted alkenyl groups (specific example group G4A):

[0285] vinyl,

[0286] Allyl

[0287] 1-Butenyl,

[0288] 2-Butenyl and 3-Butenyl.

[0289] • Substituted alkenyl groups (specific example group G4B):

[0290] 1,3-Butadienyl,

[0291] 1-Methylvinyl

[0292] 1-Methylallyl,

[0293] 1,1-Dimethylallyl,

[0294] 2-Methylallyl and 1,2-dimethylallyl.

[0295] • "Substituted or unsubstituted alkynyl groups"

[0296] 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".

[0297] "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.

[0298] • Unsubstituted alkynyl group (specific example group G5A): ethynyl group.

[0299] • "Substituted or unsubstituted cycloalkyl groups"

[0300] 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.

[0301] "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.

[0302] • Unsubstituted cycloalkyl groups (specific example group G6A):

[0303] Cyclopropyl

[0304] Cyclobutyl,

[0305] Cyclopentyl,

[0306] Cyclohexyl,

[0307] 1-Adamantyl,

[0308] 2-Adamantyl,

[0309] 1-norborneol and 2-norborneol.

[0310] • Substituted cycloalkyl group (specific example group G6B): 4-methylcyclohexyl.

[0311] ·"-Si(R 901 (R) 902 (R)903 The group shown in the figure”

[0312] 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:

[0313] -Si(G1)(G1)(G1),

[0314] -Si(G1)(G2)(G2)

[0315] -Si(G1)(G1)(G2),

[0316] -Si(G2)(G2)(G2),

[0317] -Si(G3)(G3)(G3) and -Si(G6)(G6)(G6). Here,

[0318] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0319] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0320] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0321] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0322] In -Si(G1)(G1)(G1), multiple G1s may be the same or different from each other.

[0323] In -Si(G1)(G2)(G2), multiple G2s may be the same or different from each other.

[0324] In -Si(G1)(G1)(G2), multiple G1s may be the same or different from each other.

[0325] In -Si(G2)(G2)(G2), multiple G2s may be the same or different from each other.

[0326] In -Si(G3)(G3)(G3), multiple G3s may be the same or different from each other.

[0327] In -Si(G6)(G6)(G6), multiple G6s may be the same or different from each other.

[0328] ·“-O-(R 904 The group shown in the figure”

[0329] As described in this specification, -O-(R)904 Specific examples of the group shown in the figure (specific example group G8) can be given as follows:

[0330] -O(G1)

[0331] -O(G2),

[0332] -O(G3) and -O(G6).

[0333] Here,

[0334] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0335] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0336] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0337] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0338] ·“-S-(R 905 The group shown in the figure”

[0339] As described in this specification, -S-(R) 905 Specific examples of the group shown in the figure (specific example group G9) can be given as follows:

[0340] -S(G1),

[0341] -S(G2),

[0342] -S(G3) and -S(G6).

[0343] Here,

[0344] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0345] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0346] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0347] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0348] ·"-N(R 906 (R) 907 The group shown in the figure”

[0349] As described in this specification, -N(R) 906 (R) 907Specific examples of the group shown (specific example group G10) can be given as follows:

[0350] -N(G1)(G1),

[0351] -N(G2)(G2),

[0352] -N(G1)(G2),

[0353] -N(G3)(G3) and -N(G6)(G6).

[0354] Here,

[0355] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0356] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0357] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0358] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0359] In -N(G1)(G1), multiple G1s may be the same or different from each other.

[0360] In -N(G2)(G2), multiple G2 values ​​may be the same or different from each other.

[0361] In -N(G3)(G3), multiple G3s may be the same or different from each other.

[0362] In -N(G6)(G6), multiple G6 values ​​may be the same or different from each other.

[0363] • "Halogen atom"

[0364] Specific examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0365] • "Substituted or unsubstituted fluoroalkyl groups"

[0366] 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.

[0367] • "Substituted or unsubstituted haloalkyl groups"

[0368] 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.

[0369] • "Substituted or unsubstituted alkoxy groups"

[0370] 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.

[0371] • "Substituted or unsubstituted alkylthio groups"

[0372] 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.

[0373] • "Substituted or unsubstituted aryloxy groups"

[0374] 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.

[0375] • "Substituted or unsubstituted arylthio groups"

[0376] 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.

[0377] • "Substituted or unsubstituted trialkylsilyl groups"

[0378] 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.

[0379] • "Substituted or unsubstituted aralkyl groups"

[0380] 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.

[0381] 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.

[0382] 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.

[0383] 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.

[0384] In this specification, the carbazoyl group, unless otherwise specified herein, specifically refers to any one of the following groups.

[0385] [Chemical Formula 7]

[0386]

[0387] In this specification, (9-phenyl)carbazolyl refers specifically to any one of the following groups unless otherwise specified herein.

[0388] [Chemical Formula 8]

[0389]

[0390] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.

[0391] In this specification, dibenzofuranyl and dibenzothiopheneyl are specifically any one of the following groups unless otherwise stated in this specification.

[0392] [Chemical Formula 9]

[0393]

[0394] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.

[0395] 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.

[0396] • "Substituted or unsubstituted aryl groups"

[0397] 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.

[0398] • "Substituted or unsubstituted divalent heterocyclic groups"

[0399] 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.

[0400] • "Substituted or unsubstituted alkylene compounds"

[0401] 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.

[0402] 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).

[0403]

Chemical Formula 10

[0404]

[0405]

Chemical Formula 11

[0406]

[0407] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0408] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.

[0409]

Chemical Formula 12

[0410]

[0411] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0412] Formulas Q9 and Q 10 They can form rings by bonding with each other via single bonds.

[0413] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.

[0414]

Chemical Formula 13

[0415]

[0416] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0417] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.

[0418] 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).

[0419]

Chemical Formula 14

[0420]

[0421]

Chemical Formula 15

[0422]

[0423] [Chemical Formula 16]

[0424]

[0425] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0426]

Chemical Formula 17

[0427]

[0428] [Chemical Formula 18]

[0429]

[0430] [Chemical Formula 19]

[0431]

[0432]

Chemical Formula 20

[0433]

[0434] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0435] The above is an explanation of "substituents described in this specification".

[0436] • "Cases where bonds form rings"

[0437] In this specification, the phrase "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".

[0438] 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.

[0439]

Chemical Formula 21

[0440]

[0441] 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 930group, R 930 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.

[0442] 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 In this case, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0443]

Chemical Formula 22

[0444]

[0445] 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 .

[0446]

Chemical Formula 23

[0447]

[0448] 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.

[0449] "Unsaturated rings" refer to aromatic hydrocarbon rings or aromatic heterocycles. "Saturated rings" refer to aliphatic hydrocarbon rings or non-aromatic heterocycles.

[0450] 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.

[0451] 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.

[0452] 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.

[0453] "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 four carbon atoms form a monocyclic unsaturated ring, R 921 With R 922 The resulting ring is a benzene ring.

[0454] 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.

[0455] 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.

[0456] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".

[0457] Unless otherwise stated in this specification, the term "saturated ring" is preferred over "unsaturated ring".

[0458] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.

[0459] Unless otherwise stated in this specification, the "unsaturated ring" is preferably a benzene ring.

[0460] 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.

[0461] 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.

[0462] 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.

[0463] 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").

[0464] Substituents when described as "substituted or unsubstituted"

[0465] 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...

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

[0467] Unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0468] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms

[0469] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0470] -Si(R 901 (R) 902 (R) 903 ),

[0471] -O-(R 904 ),

[0472] -S-(R 905 ),

[0473] -N(R 906 (R) 907 ),

[0474] Halogen atom, cyano group, nitro group,

[0475] Groups in the group consisting of unsubstituted aryl groups with 6 to 50 carbon atoms and unsubstituted heterocyclic groups with 5 to 50 atoms, etc.

[0476] Here, R 901 ~R 907 Each independently

[0477] hydrogen atom,

[0478] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0479] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0480] 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.

[0481] 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.

[0482] 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.

[0483] 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.

[0484] 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.

[0485] 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.

[0486] 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.

[0487] 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.

[0488] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.

[0489] Alkyl groups with 1 to 50 carbon atoms

[0490] Groups in the group consisting of aryl groups with 6 to 50 carbon atoms and heterocyclic groups with 5 to 50 atoms.

[0491] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.

[0492] Alkyl groups having 1 to 18 carbon atoms

[0493] Groups in the group consisting of aryl groups with 6 to 18 carbon atoms and heterocyclic groups with 5 to 18 atoms.

[0494] Specific examples of each of the optional substituents are those described in the section "Substituents as described in this specification" above.

[0495] 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.

[0496] 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.

[0497] 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.

[0498] [First Embodiment]

[0499] [Organic electroluminescent element]

[0500] The organic electroluminescent element involved in this embodiment is an organic electroluminescent element that has a light-emitting layer between the anode and the cathode. A first layer is provided between the cathode and the light-emitting layer. The thickness of the first layer is 50 nm or more. The first layer contains a compound of the following general formula (100). It should be noted that the first layer does not contain metal doping materials.

[0501] In this specification, a metal-doped material is a metal, metal compound, or metal complex with a work function of 4.2 eV or less. A metal, metal compound, or metal complex with a work function of 4.2 eV or less is selected from any one of alkali metals, alkaline earth metals, transition metals including rare earth metals, compounds containing the alkali metal, compounds containing the alkaline earth metal, compounds containing the transition metal, complexes containing the alkali metal, complexes containing the alkaline earth metal, and complexes containing the transition metal. Examples of metal-doped materials include lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), calcium (Ca), strontium (Sr), and barium (Ba), metal compounds such as cesium carbonate, and metal complexes such as Liq.

[0502] In addition to the light-emitting layer and the first layer, the organic EL device according to this embodiment may have one or more organic layers. Examples of organic layers include at least one layer selected from hole injection layer, hole transport layer, light-emitting layer, electron injection layer, electron transport layer, hole blocking layer and electron blocking layer.

[0503] In the organic EL element of this embodiment, the organic layer may consist only of a light-emitting layer and a first layer, or it may also have at least one layer selected from, for example, 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.

[0504] (The general structure of an organic EL device)

[0505] Figure 1 The diagram shows a general configuration of an example of an organic EL element involved in this embodiment.

[0506] The organic EL element 1 includes a substrate 2, an anode 3, a semi-transparent electrode 4 serving as a cathode, and an organic layer 10 disposed between the anode 3 and the semi-transparent electrode 4. The organic EL element 1 includes a capping layer 8 disposed on the side of the semi-transparent electrode 4 opposite to the organic layer.

[0507] The organic layer 10 is formed by stacking the hole transport region 6, the light-emitting layer 5, and the electron transport region 7 in sequence, starting from the anode 3 side.

[0508] In the organic EL element of this embodiment, the anode 3 includes a light-reflecting layer 31 and a transparent electrode 32. The anode 3 is formed by stacking the light-reflecting layer 31 and the transparent electrode 32 in this order from the substrate 2 side.

[0509] In the organic EL element of this embodiment, the hole transport region 6 includes a hole injection layer 61 and a hole transport layer 62. The hole transport region 6 is formed by stacking the hole injection layer 61 and the hole transport layer 62 in this order from the transparent electrode 32 side.

[0510] In the organic EL element of this embodiment, the electron transport region 7 includes a first layer 71 and an electron injection layer 72. The electron transport region 7 is formed by stacking the first layer 71 and the electron injection layer 72 in this order starting from the light-emitting layer 5 side.

[0511] In the organic EL element involved in this embodiment, it is also preferable that the light-emitting layer is directly connected to the first layer.

[0512] exist Figure 1 In one example of the organic EL element involved in this embodiment, the light-emitting layer 5 is directly connected to the first layer 71.

[0513] In the organic EL element of this embodiment, it is also preferable to have a second layer between the light-emitting layer and the first layer.

[0514] Figure 2 The diagram shows a general configuration of an example of an organic EL element involved in this embodiment.

[0515] The organic EL element 1A includes a substrate 2, an anode 3, a semi-transparent electrode 4 serving as a cathode, and an organic layer 10 disposed between the anode 3 and the semi-transparent electrode 4. The organic EL element 1A includes a capping layer 8 disposed on the side of the semi-transparent electrode 4 opposite to the organic layer.

[0516] In the organic EL element 1A, the organic layer 10 is also constructed by stacking the hole transport region 6, the light-emitting layer 5, and the electron transport region 7A in sequence, starting from the anode 3 side.

[0517] In the organic EL element 1A, the anode 3 also includes a light-reflecting layer 31 and a transparent electrode 32. The anode 3 is formed by stacking the light-reflecting layer 31 and the transparent electrode 32 in this order from the substrate 2 side.

[0518] In the organic EL element 1A, the hole transport region 6 also includes a hole injection layer 61 and a hole transport layer 62. The hole transport region 6 is formed by stacking the hole injection layer 61 and the hole transport layer 62 in this order from the transparent electrode 32 side.

[0519] In the organic EL element 1A, the electron transport region 7A includes a first layer 71, an electron injection layer 72, and a second layer 73. The electron transport region 7A is formed by stacking the second layer 73, the first layer 71, and the electron injection layer 72 in this order, starting from the light-emitting layer 5 side.

[0520] In the organic EL element of this embodiment, it is also preferable to have a third layer between the cathode and the first layer.

[0521] In the organic EL element involved in this embodiment, it is preferred that the third layer is an organic compound layer containing alkali metal, alkaline earth metal, alkali metal compound or alkaline earth metal compound.

[0522] Figure 3 The diagram shows a general configuration of an example of an organic EL element involved in this embodiment.

[0523] The organic EL element 1B includes a substrate 2, an anode 3, a semi-transparent electrode 4 serving as a cathode, and an organic layer 10 disposed between the anode 3 and the semi-transparent electrode 4. The organic EL element 1B includes a capping layer 8 disposed on the side of the semi-transparent electrode 4 opposite to the organic layer.

[0524] In the organic EL element 1B, the organic layer 10 is also constructed by stacking the hole transport region 6, the light-emitting layer 5, and the electron transport region 7B in sequence, starting from the anode 3 side.

[0525] The anode 3 and hole transport region 6 in organic EL element 1B are configured in the same way as organic EL element 1 or organic EL element 1A.

[0526] In the organic EL element 1B, the electron transport region 7B includes a first layer 71, a third layer 74, and an electron injection layer 72. The electron transport region 7B is formed by stacking the first layer 71, the third layer 74, and the electron injection layer 72 in this order, starting from the light-emitting layer 5 side.

[0527] Figure 4 The diagram shows a general configuration of an example of an organic EL element involved in this embodiment.

[0528] The organic EL element 1C includes a substrate 2, an anode 3, a semi-transparent electrode 4 serving as a cathode, and an organic layer 10 disposed between the anode 3 and the semi-transparent electrode 4. The organic EL element 1C includes a capping layer 8 disposed on the side of the semi-transparent electrode 4 opposite to the organic layer.

[0529] In the organic EL element 1C, the organic layer 10 is also constructed by stacking the hole transport region 6, the light-emitting layer 5, and the electron transport region 7C in sequence, starting from the anode 3 side.

[0530] The anode 3 and hole transport region 6 in organic EL element 1C are configured in the same way as organic EL element 1 or organic EL element 1A.

[0531] In the organic EL element 1C, the electron transport region 7C includes a first layer 71, a second layer 73, a third layer 74, and an electron injection layer 72. The electron transport region 7C is formed by stacking the second layer 73, the first layer 71, the third layer 74, and the electron injection layer 72 in this order, starting from the light-emitting layer 5 side.

[0532] In the organic EL element of this embodiment, it is preferable that the distance D1 between the interface of the cathode on the light-emitting layer side and the interface of the light-emitting layer on the cathode side is greater than the distance D2 between the interface of the anode on the light-emitting layer side and the interface of the light-emitting layer on the anode side.

[0533] In organic EL element 1, organic EL element 1A, organic EL element 1B or organic EL element 1C, it is also preferable that the distance D1 between the interface of the semi-transparent electrode 4 serving as the cathode on the light-emitting layer 5 side and the interface of the light-emitting layer 5 serving as the cathode on the semi-transparent electrode 4 side is greater than the distance D2 between the interface of the anode 3 serving as the light-emitting layer 5 side and the interface of the light-emitting layer 5 serving as the anode 3 side.

[0534] (First layer)

[0535] The first layer is the layer disposed between the cathode and the light-emitting layer.

[0536] For example, in organic EL element 1, the first layer 71 is disposed between the light-emitting layer 5 and the electron injection layer 72. In organic EL element 1A, the first layer 71 is disposed between the second layer 73 and the electron injection layer 72. In organic EL element 1B, the first layer 71 is disposed between the light-emitting layer and the third layer 74. In organic EL element 1C, the first layer 71 is disposed between the second layer 73 and the third layer 74.

[0537] The thickness of the first layer is 50 nm or more, and from the viewpoint of optical interference conditions, it is preferably 70 nm or more, more preferably 100 nm or more, and even more preferably 120 nm or more.

[0538] The thickness of the first layer is preferably less than 160 nm, and more preferably less than 150 nm.

[0539] The thickness of the first layer is preferably greater than the thickness of the layers other than the first layer disposed between the cathode and the light-emitting layer. For example, in Figure 1 In the case of the organic EL device 1 shown, the thickness of the first layer 71 is preferably thicker than the thickness of the electron injection layer 72. Furthermore, in Figure 2 In the case of the organic EL element 1A shown, the thickness of the first layer 71 is preferably thicker than the thickness of the second layer 73 and the electron injection layer 72.

[0540] Compounds of general formula (100)

[0541] The first layer of the organic EL element involved in this embodiment contains a compound represented by the following general formula (100).

[0542]

Chemical Formula 24

[0543]

[0544] (In the above general formula (100),

[0545] A is

[0546] Substituted or unsubstituted fused aryl groups with 13 or more but less than 50 cyclic carbons, or

[0547] Fused heterocyclic groups with 14 or more but less than 50 cyclic atoms, whether substituted or unsubstituted.

[0548] L A for

[0549] single bond,

[0550] Substituted or unsubstituted arylene groups with 6 or more but less than 30 carbon atoms in the cyclic group, or

[0551] A divalent heterocyclic group, with 5 or more but less than 30 cyclic atoms, whether substituted or unsubstituted.

[0552] X1, X2, and X3 are each independently nitrogen atoms or CR3.

[0553] X P It is a nitrogen atom or CR1.

[0554] X Q It is a nitrogen atom or CR2.

[0555] It should be noted that X1, X2, X3, X P and X Q One or more of them are nitrogen atoms.

[0556] One or more groups consisting of two or more adjacent elements from R1, R2, and R3.

[0557] They bond together to form substituted or unsubstituted monocyclic rings.

[0558] They bond together to form substituted or unsubstituted fused rings, or

[0559] They do not bond with each other.

[0560] R1, R2, and R3, 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 […].

[0561] hydrogen atom,

[0562] Substituted or unsubstituted aryl groups with 6 or more but less than 30 carbon atoms in the cyclic group, or

[0563] Heterocyclic groups with 5 or more but less than 30 cyclic atoms, whether substituted or unsubstituted.

[0564] In the case of multiple R3s, these R3s may be identical or different from each other.

[0565] In the above general formula (100), X is also preferred. P For CR1, X Q If the compound is CR2, then the compound of the above general formula (100) is the compound of the following general formula (1).

[0566] Compounds of general formula (1)

[0567] The compounds of the above general formula (100) are also preferably compounds of the following general formula (1).

[0568] The first layer of the organic EL element involved in this embodiment preferably also contains a compound represented by the following general formula (1).

[0569] [Chemical Formula 25]

[0570]

[0571] (In the above general formula (1),

[0572] A is

[0573] Substituted or unsubstituted fused aryl groups with 13 or more but less than 50 cyclic carbons, or

[0574] Fused heterocyclic groups with 14 or more but less than 50 cyclic atoms, whether substituted or unsubstituted.

[0575] L A for

[0576] single bond,

[0577] Substituted or unsubstituted arylene groups with 6 or more but less than 30 carbon atoms in the cyclic group, or

[0578] A divalent heterocyclic group, with 5 or more but less than 30 cyclic atoms, whether substituted or unsubstituted.

[0579] X1, X2, and X3 are each independently nitrogen atoms or CR3.

[0580] It should be noted that more than one of X1, X2, and X3 is a nitrogen atom.

[0581] One or more groups consisting of two or more adjacent elements from R1, R2, and R3.

[0582] They bond together to form substituted or unsubstituted monocyclic rings.

[0583] They bond together to form substituted or unsubstituted fused rings, or

[0584] They do not bond with each other.

[0585] R1, R2, and R3, 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 […].

[0586] hydrogen atom,

[0587] Substituted or unsubstituted aryl groups with 6 or more but less than 30 carbon atoms in the cyclic group, or

[0588] Heterocyclic groups with 5 or more but less than 30 cyclic atoms, whether substituted or unsubstituted.

[0589] In the case of multiple R3s, these R3s may be identical or different from each other.

[0590] In this specification, a fused aryl group is a monovalent aryl group derived by removing one hydrogen atom from a ring structure formed by the fusion of multiple monocyclic aromatic hydrocarbon rings. Examples of fused aryl groups include 1-naphthyl, 2-naphthyl, anthraceneyl, benzanthraceneyl, phenanthryl, benzophenanthryl, phenatenyl, pyreneyl, etc. Benzyl, benzo[ The aryl groups include phenylene, benzotriphenylene, tetraphenylene, pentaphenylene, fluorenyl, 9,9'-spirobisfluorenyl, benzo[fluorenyl], dibenzo[fluorenyl], fluoranyl, benzo[fluoranyl], peryl, and monovalent aryl groups derived from the ring structures shown in the above general formulas (TEMP-1) to (TEMP-15) by removing one hydrogen atom. Fused aryl groups in this specification do not include groups consisting of multiple monocyclic rings linked by single bonds (e.g., biphenyl, terphenyl, etc.).

[0591] In the organic EL element of this embodiment, the fused aryl group with 13 or more and 50 or less cyclic carbons is the group with 13 or more and 50 or less cyclic carbons among the aforementioned fused aryl groups.

[0592] In this specification, a fused heterocyclic group is a monovalent heterocyclic group derived by removing one hydrogen atom from a ring structure formed by fusion of at least one heterocycle as a monocyclic ring with at least one ring selected from monocyclic heterocycles and aromatic hydrocarbon rings as monocyclic rings. Examples of fused heterocyclic groups include indole, isoyindolyl, indazinyl, quinazinyl, quinolinyl, isoquinolinyl, terpineyl, phthalazinyl, quinazolinyl, quinoxalolinyl, benzimidazolyl, indazolyl, phenanthrolinel, phenanthidyl, acridinel, phenazinyl, carbazole, benzo[a]carbazole, morpholinyl, phenoxazinyl, phenothiazinyl, azacarbazole, diazacarbazole, xanthonyl, benzofuranyl, isobenzofuranyl. Benzyl, dibenzofuranyl, naphthobenzofuranyl, benzoxazolyl, benzoisoxazolyl, phenoxazinyl, dinaphthofuranyl, azadibenzofuranyl, diazadibenzofuranyl, azanaphthobenzofuranyl, diazanaphthobenzofuranyl, benzothienyl, isobenzothienyl, dibenzothienyl dibenzothienyl), naphthobenzothienyl, benzothiazolyl, benzoisothiazolyl, phenothiazinyl, dinaphthothienyl, azadibenzothienyl, diazadibenzothienyl, azadibenzothienyl, azanaphthobenzothienyl, diazanaphthobenzothienyl, and monovalent heterocyclic groups derived from the ring structures shown in the above general formulas (TEMP-16) to (TEMP-33) by removing one hydrogen atom.

[0593] In the organic EL element of this embodiment, the fused heterocyclic group with 14 or more and 50 or less cyclic atoms is the group with 14 or more and 50 or less cyclic atoms among the aforementioned fused heterocyclic groups.

[0594] In the organic EL element involved in this embodiment, it is also preferred that the compound of the above general formula (100) is a compound of the following general formula (101).

[0595]

Chemical Formula 26

[0596]

[0597] (In the above general formula (101),

[0598] X1~X3, X P X Q R1~R3 ​​and L A Each of them is the same as the definition in the above general formula (100).

[0599] R 11 ~R 20 One of them is related to L A The bonding position*

[0600] Not related to L A The bonding position of R 11 ~R 20 One or more groups consisting of two or more adjacent elements.

[0601] They bond together to form substituted or unsubstituted monocyclic rings.

[0602] They bond together to form substituted or unsubstituted fused rings, or

[0603] They do not bond with each other.

[0604] Not with L A The bonding sites and do not form the aforementioned substituted or unsubstituted monocyclic rings and do not form the aforementioned substituted or unsubstituted fused rings of R. 11 ~R 20 Each is independently identical to the definition in the following general formula (A1).

[0605] In the organic EL element involved in this embodiment, it is also preferred that the compound of the above general formula (1) is a compound of the following general formula (A1).

[0606] [Chemical Formula 27]

[0607]

[0608] (In the above general formula (A1),

[0609] X1~X3, R1~R3 and L A Each of them is the same as the definition in the general formula (1) above.

[0610] R 11 One of ~R20 is related to L A The bonding position*

[0611] Not related to L A The bonding position of R 11 ~R 20 One or more groups consisting of two or more adjacent elements.

[0612] They bond together to form substituted or unsubstituted monocyclic rings.

[0613] They bond together to form substituted or unsubstituted fused rings, or

[0614] They do not bond with each other.

[0615] Not with L A The bonding sites and do not form the aforementioned substituted or unsubstituted monocyclic rings and do not form the aforementioned substituted or unsubstituted fused rings of R. 11 ~R 20 Each independently

[0616] hydrogen atom,

[0617] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0618] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0619] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0620] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0621] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0622] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0623] -O-(R 904 The groups shown in the figure,

[0624] -S-(R 905 The groups shown in the figure,

[0625] -N(R 906 (R) 907 The groups shown in the figure,

[0626] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0627] -C(=O)R 801 The groups shown

[0628] -COOR 802 The groups shown

[0629] Halogen atoms,

[0630] cyano,

[0631] Nitro,

[0632] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0633] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0634] R 901 R 902 R 903 R 904R 905 R 906 R 907 R 801 and R 802 Each independently

[0635] hydrogen atom,

[0636] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0637] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0638] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0639] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0640] In the existence of multiple R 901 In the case of multiple R 901 They are the same or different.

[0641] In the existence of multiple R 902 In the case of multiple R 902 They are the same or different.

[0642] In the existence of multiple R 903 In the case of multiple R 903 They are the same or different.

[0643] In the existence of multiple R 904 In the case of multiple R 904 They are the same or different.

[0644] In the existence of multiple R 905 In the case of multiple R 905 They are the same or different.

[0645] In the existence of multiple R 906 In the case of multiple R 906 They are the same or different.

[0646] In the existence of multiple R 907 In the case of multiple R 907 They are the same or different.

[0647] In the existence of multiple R 801 In the case of multiple R 801 They are the same or different.

[0648] In the existence of multiple R 802 In the case of multiple R 802 (They may be the same or different.)

[0649] In the organic EL element involved in this embodiment, in the adjacent R 12 and R 13 When the groups of components bond together to form substituted or unsubstituted monocyclic rings or substituted or unsubstituted fused rings, the compounds of the above general formula (1) are represented by the following general formula (A-Q1).

[0650] In the organic EL element involved in this embodiment, in the adjacent R 13 and R 14 When the groups of components bond together to form substituted or unsubstituted monocyclic rings or substituted or unsubstituted fused rings, the compounds of the above general formula (1) are represented by the following general formula (A-Q2).

[0651] [Chemical Formula 28]

[0652]

[0653] [Chemical Formula 29]

[0654]

[0655] (In the above general formulas (A-Q1) and (A-Q2),

[0656] Ring Q1 and ring Q2 are each independently a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted fused ring.

[0657] X1~X3, R1~R3 and L A Each of them is the same as the definition in the general formula (1) above.

[0658] Not with L A The bonding sites and do not form the aforementioned substituted or unsubstituted monocyclic rings and do not form the aforementioned substituted or unsubstituted fused rings of R. 11 ~R 20 Each is independently identical to the definition in the general formula (A1) above.

[0659] Preferably, ring Q1 and ring Q2 are each independently a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle.

[0660] In the organic EL element involved in this embodiment, it is preferred that it is not related to L A The bonding sites and do not form the aforementioned substituted or unsubstituted monocyclic rings and do not form the aforementioned substituted or unsubstituted fused rings of R. 11 ~R 20 Two or more of them are not hydrogen atoms.

[0661] In the organic EL element involved in this embodiment, it is preferred that it is not related to L AThe bonding sites and do not form the aforementioned substituted or unsubstituted monocyclic rings and do not form the aforementioned substituted or unsubstituted fused rings of R. 11 ~R 20 Two or more of them are independently

[0662] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0663] A heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0664] In the organic EL element involved in this embodiment, R is preferred. 19 and R 20 Each independently

[0665] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0666] A heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0667] In the organic EL element involved in this embodiment, R is also preferred. 12 R 13 R 16 Or R 17 To be with L A The bonding location. In R 13 To be with L A When the bonding position is such that the compound of the above general formula (100) is represented by the following general formula (102), and the compound of the above general formula (1) is represented by the following general formula (A1-1).

[0668] In the organic EL element involved in this embodiment, it is also preferred that the compound of the above general formula (100) is a compound of the following general formula (102).

[0669]

Chemical Formula 30

[0670]

[0671] (In the above general formula (102),

[0672] X1~X3, X P X Q R1~R3 ​​and L A Each of them is the same as the definition in the above general formula (100).

[0673] R 11 R 12 R 14 ~R 20 Each is independently identical to the definition in the following general formula (A1-1).

[0674] Among the compounds of the above general formula (100), X is also preferred. P and X Q One or more of them are nitrogen atoms.

[0675] Among the compounds of the above general formula (100), X is also preferred. P For CR1, X Q It is a nitrogen atom.

[0676] Among the compounds of the above general formula (100), X is also preferred. P For CR1, X Q X1, X2, and X3 are nitrogen atoms, and X3 is CR3.

[0677] Among the compounds of the above general formula (100), X is also preferred. P X is a nitrogen atom. Q It is CR2.

[0678] Among the compounds of the above general formula (100), X is also preferred. P X is a nitrogen atom. Q X1, X2, and X3 are CR2, and X3 are CR3.

[0679] In the organic EL element involved in this embodiment, it is also preferred that the compound of the above general formula (1) is a compound of the following general formula (A1-1).

[0680]

Chemical Formula 31

[0681]

[0682] (In the above general formula (A1-1),

[0683] X1~X3, R1~R3 and L A Each of them is the same as the definition in the general formula (1) above.

[0684] By R 11 R 12 R 14 ~R 20 One or more groups consisting of two or more adjacent elements.

[0685] They bond together to form substituted or unsubstituted monocyclic rings.

[0686] They bond together to form substituted or unsubstituted fused rings, or

[0687] They do not bond with each other.

[0688] Not with L A The bonding sites and do not form the aforementioned substituted or unsubstituted monocyclic rings and do not form the aforementioned substituted or unsubstituted fused rings of R. 11 R12 R 14 ~R 20 Each independently

[0689] hydrogen atom,

[0690] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0691] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0692] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0693] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0694] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0695] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0696] -O-(R 904 The groups shown in the figure,

[0697] -S-(R 905 The groups shown in the figure,

[0698] -N(R 906 (R) 907 The groups shown in the figure,

[0699] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0700] -C(=O)R 801 The groups shown

[0701] -COOR 802 The groups shown

[0702] Halogen atoms,

[0703] cyano,

[0704] Nitro,

[0705] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0706] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0707] R 901 R 902 R 903 R 904 R 905 R 906 R907 R 801 and R 802 Each of them is the same as the definition in the general formula (A1) above.

[0708] In the above general formula (A1-1), it is preferred that R 19 and R 20 Each independently

[0709] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0710] A heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0711] In the organic EL element involved in this embodiment, R is also preferred. 19 Or R 20 To be with L A The bonding location. In R 20 To be with L A When the bonding position is such that the compound of the above general formula (1) is represented by the following general formula (A1-2).

[0712] In the organic EL element involved in this embodiment, it is also preferred that the compound of the above general formula (1) is a compound of the following general formula (A1-2).

[0713]

Chemical Formula 32

[0714]

[0715] (In the above general formula (A1-2),

[0716] X1~X3, R1~R3 and L A Each of them is the same as the definition in the general formula (1) above.

[0717] By R 11 ~R 19 One or more groups consisting of two or more adjacent elements.

[0718] They bond together to form substituted or unsubstituted monocyclic rings.

[0719] They bond together to form substituted or unsubstituted fused rings, or

[0720] They do not bond with each other.

[0721] Not with L A The bonding sites and do not form the aforementioned substituted or unsubstituted monocyclic rings and do not form the aforementioned substituted or unsubstituted fused rings of R. 11 ~R 19 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] -N(R 906 (R) 907 The groups shown in the figure,

[0732] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0733] -C(=O)R 801 The groups shown

[0734] -COOR 802 The groups shown

[0735] Halogen atoms,

[0736] cyano,

[0737] Nitro,

[0738] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0739] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0740] R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each of them is the same as the definition in the general formula (A1) above.

[0741] In the organic EL element involved in this embodiment,

[0742] Preferably, R 19 for

[0743] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0744] A heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0745] In the organic EL element involved in this embodiment,

[0746] Preferably, R 19 for

[0747] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0748] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0749] R1 and R2 are each independently an aryl group, either substituted or unsubstituted, with 6 or more but less than 50 cyclic carbons.

[0750] In the organic EL element involved in this embodiment, it is also preferred that the compound of the above general formula (1) is a compound of the following general formula (B1).

[0751]

Chemical Formula 33

[0752]

[0753] (In the above general formula (B1),

[0754] X1~X3, R1~R3 and L A Each of them is the same as the definition in the general formula (1) above.

[0755] R 21 ~R 28 One of them is related to L A The bonding position*

[0756] Not with L A The bonding position of R 21 ~R 28 Each independently

[0757] hydrogen atom,

[0758] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0759] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0760] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0761] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0762] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0763] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0764] -O-(R 904 The groups shown in the figure,

[0765] -S-(R 905 The groups shown in the figure,

[0766] -N(R 906 (R) 907 The groups shown in the figure,

[0767] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0768] -C(=O)R 801 The groups shown

[0769] -COOR 802 The groups shown

[0770] Halogen atoms,

[0771] cyano,

[0772] Nitro,

[0773] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0774] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0775] Group consisting of R4 and R5

[0776] They bond together to form substituted or unsubstituted monocyclic rings.

[0777] They bond together to form substituted or unsubstituted fused rings, or

[0778] They do not bond with each other.

[0779] R4 and R5, 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 […].

[0780] hydrogen atom,

[0781] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0782] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0783] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0784] R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently

[0785] hydrogen atom,

[0786] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0787] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0788] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0789] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0790] In the existence of multiple R 901 In the case of multiple R 901 They are the same or different.

[0791] In the existence of multiple R 902 In the case of multiple R 902 They are the same or different.

[0792] In the existence of multiple R 903 In the case of multiple R 903 They are the same or different.

[0793] In the existence of multiple R 904 In the case of multiple R 904 They are the same or different.

[0794] In the existence of multiple R 905 In the case of multiple R 905 They are the same or different.

[0795] In the existence of multiple R 906 In the case of multiple R 906 They are the same or different.

[0796] In the existence of multiple R 907 In the case of multiple R 907 They are the same or different.

[0797] In the existence of multiple R 801 In the case of multiple R 801They are the same or different.

[0798] In the existence of multiple R 802 In the case of multiple R 802 (They may be the same or different.)

[0799] In the organic EL element involved in this embodiment, it is preferred that R4 and R5 are each independently substituted or unsubstituted aryl groups with 6 to 50 cyclic carbons.

[0800] In the organic EL element involved in this embodiment, it is preferred that R4 and R5 are each independently substituted or unsubstituted phenyl groups.

[0801] In the organic EL element of this embodiment, the compound of the above general formula (B1) is preferably a compound of the following general formula (B1-1).

[0802] [Chemical Formula 34]

[0803]

[0804] (In the above general formula (B1-1),

[0805] X1~X3, R1~R3 and L A Each of them is the same as the definition in the general formula (1) above.

[0806] R 21 ~R 28 Each of them is the same as the definition in the general formula (B1) above.

[0807] Ring B can be a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted fused ring.

[0808] Ring B is preferably a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle.

[0809] In the organic EL element of this embodiment, the compound of the above general formula (B1) is preferably a compound of the following general formula (B1-1A).

[0810]

Chemical Formula 35

[0811]

[0812] (In the above general formula (B1-1A),)

[0813] X1~X3, R1~R3 and L A Each of them is the same as the definition in the general formula (1) above.

[0814] R 21 ~R 28 Each of them is the same as the definition in the general formula (B1) above.

[0815] Ring B1 and ring B2 are each independently either substituted or unsubstituted monocyclic rings, or substituted or unsubstituted fused rings.

[0816] Preferably, ring B1 and ring B2 are each independently a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle.

[0817] In the organic EL element of this embodiment, the compound of the above general formula (B1) is preferably a compound of the following general formula (B1-2).

[0818]

Chemical Formula 36

[0819]

[0820] (In the above general formula (B1-2),

[0821] X1~X3, R1~R3 and L A Each of them is the same as the definition in the general formula (1) above.

[0822] R 21 ~R 28 Each of them is the same as the definition in the general formula (B1-1) above.

[0823] By R 211 ~R 218 One or more groups consisting of two or more adjacent elements.

[0824] They bond together to form substituted or unsubstituted monocyclic rings.

[0825] They bond together to form substituted or unsubstituted fused rings, or

[0826] They do not bond with each other.

[0827] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 211 ~R 218 Each independently

[0828] hydrogen atom,

[0829] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0830] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0831] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0832] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0833] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0834] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0835] -O-(R 904 The groups shown in the figure,

[0836] -S-(R 905 The groups shown in the figure,

[0837] -N(R 906 (R) 907 The groups shown in the figure,

[0838] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0839] -C(=O)R 801 The groups shown

[0840] -COOR 802 The groups shown

[0841] Halogen atoms,

[0842] cyano,

[0843] Nitro,

[0844] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0845] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0846] R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each of these is defined identically to the one in the general formula (B1) above.

[0847] Not with L A The bonding position of R 211 ~R 218 Preferably, neither the aforementioned substituted or unsubstituted monocyclic rings nor the aforementioned substituted or unsubstituted fused rings are formed.

[0848] In the organic EL element involved in this embodiment, R is also preferred. 21 Or R 28 To be with L A The bonding position*.

[0849] In the organic EL element involved in this embodiment, R is also preferred. 22 Or R 27 To be with L A The bonding position*.

[0850] In the organic EL element involved in this embodiment, R is also preferred. 23 Or R 26 To be with L A The bonding position*.

[0851] In the organic EL element involved in this embodiment, R is also preferred. 24 Or R 25 To be with L A The bonding position*.

[0852] In the organic EL element involved in this embodiment, for example in R 25 To be with L A When the bonding position is *, the compound of the above general formula (B1) is represented by the following general formula (B1-3).

[0853]

Chemical Formula 37

[0854]

[0855] (In the above general formula (B1-3),

[0856] X1~X3, R1~R3 and L A Each of them is the same as the definition in the general formula (1) above.

[0857] R4, R5, R 21 ~R 24 and R 26 ~R 28 Each of these is defined identically to the one in the general formula (B1) above.

[0858] In the organic EL element involved in this embodiment, it is preferred that,

[0859] A is

[0860] Substituted or unsubstituted fused aryl groups with 13 or more but less than 30 cyclic carbons, or

[0861] Fused heterocyclic groups with 14 or more but less than 30 cyclic atoms, whether substituted or unsubstituted.

[0862] In the organic EL element involved in this embodiment, it is preferred that,

[0863] A is

[0864] Substituted or unsubstituted fused aryl groups with 13 or more but less than 20 cyclic carbons, or

[0865] Fused heterocyclic groups with 14 or more but less than 20 cyclic atoms, whether substituted or unsubstituted.

[0866] In the organic EL element involved in this embodiment, it is preferred that A is a fused heterocyclic group with 14 or more and 20 or less of substituted or unsubstituted cyclic atoms.

[0867] In the organic EL element of this embodiment, A is preferably a fused heterocyclic group containing two or more heteroatoms as cyclic atoms. Examples of heteroatoms include nitrogen atoms, oxygen atoms, sulfur atoms, silicon atoms, phosphorus atoms, and boron atoms.

[0868] In the organic EL element involved in this embodiment, the compound of the above general formula (1) is preferably a compound of the following general formula (C1).

[0869] [Chemical Formula 38]

[0870]

[0871] (In the above general formula (C1),

[0872] X A It consists of oxygen or sulfur atoms.

[0873] X1~X3, R1~R3 and L A Each of them is the same as the definition in the general formula (1) above.

[0874] R 131 ~R 139 One of them is related to L A The bonding position*

[0875] Not related to L A The bonding position of R 131 ~R 139 One or more groups consisting of two or more adjacent elements.

[0876] They bond together to form substituted or unsubstituted monocyclic rings.

[0877] They bond together to form substituted or unsubstituted fused rings, or

[0878] They do not bond with each other.

[0879] Not with L A The bonding sites and do not form the aforementioned substituted or unsubstituted monocyclic rings and do not form the aforementioned substituted or unsubstituted fused rings of R. 131 ~R 139 Each independently

[0880] hydrogen atom,

[0881] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0882] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0883] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0884] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0885] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0886] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0887] -O-(R 904 The groups shown in the figure,

[0888] -S-(R 905 The groups shown in the figure,

[0889] -N(R 906 (R) 907 The groups shown in the figure,

[0890] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0891] -C(=O)R 801 The groups shown

[0892] -COOR 802 The groups shown

[0893] Halogen atoms,

[0894] cyano,

[0895] Nitro,

[0896] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0897] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0898] R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each of them is the same as the definition in the general formula (A1) above.

[0899] In the organic EL element involved in this embodiment, it is also preferred that one of X1, X2 and X3 is a nitrogen atom.

[0900] In the organic EL element involved in this embodiment, it is also preferred that...

[0901] X2 represents nitrogen atoms.

[0902] X1 and X3 are CR3.

[0903] R3 is defined in the same way as in the general formula (1) above.

[0904] The two R3s are either the same or different.

[0905] In the organic EL element involved in this embodiment, the compound of the above general formula (1) is preferably a compound of the following general formula (1-N1) or general formula (1-N11).

[0906] [Chemical Formula 39]

[0907]

[0908]

Chemical Formula 40

[0909]

[0910] (In the above general formulas (1-N1) and (1-N11), R1, R2, R3, L A A and A are defined the same as in the general formula (1) above.

[0911] In the organic EL element involved in this embodiment, the compound of the above general formula (100) is preferably a compound of the following general formula (1-N12).

[0912]

Chemical Formula 41

[0913]

[0914] (In the above general formula (1-N12), R1, R3, L A A and A are defined the same as in the general formula (100) above.

[0915] In the organic EL element involved in this embodiment, the compound of the above general formula (100) is preferably a compound of the following general formula (A1-N12).

[0916]

Chemical Formula 42

[0917]

[0918] (In the above general formula (A1-N12),

[0919] R1, R3 and L A Each of them is the same as the definition in the above general formula (100).

[0920] R 11 R 12 R 14 ~R 20 Each of them is independently identical to the definition in the general formula (A1-1) above.

[0921] In the organic EL element involved in this embodiment, the compound of the above general formula (1) is preferably a compound of the following general formula (1-N2) or general formula (1-N21).

[0922]

Chemical Formula 43

[0923]

[0924]

Chemical Formula 44

[0925]

[0926] (In the above general formulas (1-N2) and (1-N21), R1, R2, R3, L A A and A are defined the same as in the general formula (1) above.

[0927] In the organic EL element involved in this embodiment, X1, X2 and X3 are preferably nitrogen atoms.

[0928] In the organic EL element involved in this embodiment, the compound of the above general formula (1) is preferably a compound of the following general formula (1-N3).

[0929] [Chemical Formula 45]

[0930]

[0931] (In the above general formula (1-N3), R1, R2, L A A and A are defined the same as in the general formula (1) above.

[0932] In the organic EL element involved in this embodiment, the compound of the above general formula (1) is preferably a compound of the following general formula (A1-N3).

[0933]

Chemical Formula 46

[0934]

[0935] (In the above general formula (A1-N3), R1, R2, L A R 11 ~R 20The definitions of and * are the same as those in the general formula (A1) above.

[0936] In the organic EL element involved in this embodiment, the compound of the above general formula (1) is preferably a compound of the following general formula (A1-N31) or (A1-N32).

[0937] [Chemical Formula 47]

[0938]

[0939] [Chemical Formula 48]

[0940]

[0941] (In the above general formulas (A1-N31) and (A1-N32),

[0942] R1, R2 and L A Each of them is the same as the definition in the general formula (1) above.

[0943] R 11 ~R 20 Each is independently identical to the definition in the general formula (A1) above.

[0944] In the organic EL element involved in this embodiment, the compound of the above general formula (1) is preferably a compound of the following general formula (B1-N3).

[0945] [Chemical Formula 49]

[0946]

[0947] (In the above general formula (B1-N3),

[0948] R1, R2 and L A Each of them is the same as the definition in the general formula (1) above.

[0949] R4, R5 and R 21 ~R 28 Each is independently identical to the definition in the general formula (B1) above.

[0950] In the organic EL element involved in this embodiment, it is preferred that R1 and R2 are each independently an aryl group with 6 or more but less than 50 cyclic carbons, either substituted or unsubstituted.

[0951] In the organic EL element involved in this embodiment, it is preferred that R1 and R2 are each independently an aryl group with 6 or more but less than 30 cyclic carbons, either substituted or unsubstituted.

[0952] In the organic EL element involved in this embodiment, it is also preferred that...

[0953] R1 and R2 are each independently an aryl group, either substituted or unsubstituted, with 6 or more but less than 30 carbon atoms in the cyclic group.

[0954] X1, X2, and X3 are nitrogen atoms.

[0955] In the organic EL element involved in this embodiment, it is preferred that,

[0956] R 19 and R 20 Each independently

[0957] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0958] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0959] R1 and R2 are each independently an aryl group, either substituted or unsubstituted, with 6 or more but less than 50 cyclic carbons.

[0960] In the organic EL element involved in this embodiment, it is preferred that R1 and R2 are each independently an aryl group with 6 or more and 18 or less of cyclic carbons, whether substituted or unsubstituted.

[0961] In the organic EL element involved in this embodiment, when X1 is CR3 and the group consisting of R1 and R3 is bonded to each other to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring, the compound of the above general formula (1) is represented by the following general formula (1-P1).

[0962] In the organic EL element involved in this embodiment, when X2 is CR3 and the group consisting of R1 and R3 is bonded to each other to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring, the compound of the above general formula (1) is represented by the following general formula (1-P2).

[0963] In the organic EL element involved in this embodiment, when X2 is CR3 and the group consisting of R2 and R3 is bonded to each other to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring, the compound of the above general formula (1) is represented by the following general formula (1-P3).

[0964] In the organic EL element involved in this embodiment, when X3 is CR3 and the group consisting of R2 and R3 is bonded to each other to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring, the compound of the above general formula (1) is represented by the following general formula (1-P4).

[0965] [Chemical Formula 50]

[0966]

[0967] (In the above general formulas (1-P1) to (1-P4),

[0968] Rings P1, P2, P3, and P4 are each independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.

[0969] X1, X2, X3, R1, R2, R3, L A A and A are defined the same as in the general formula (1) above.

[0970] Preferably, rings P1, P2, P3, and P4 are each independently a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle.

[0971] In the organic EL element involved in this embodiment, the compound of the above general formula (1) is preferably a compound of the following general formula (1-P11), (1-P21), (1-P31) or (1-P41).

[0972]

Chemical Formula 51

[0973]

[0974]

Chemical Formula 52

[0975]

[0976] (In the above general formulas (1-P11), (1-P21), (1-P31) and (1-P41),

[0977] R 141 ~R 144 Each independently

[0978] hydrogen atom,

[0979] Substituted or unsubstituted aryl groups with 6 or more but less than 30 carbon atoms in the cyclic group, or

[0980] Heterocyclic groups with 5 or more but less than 30 cyclic atoms, whether substituted or unsubstituted.

[0981] X1, X2, X3, R1, R2, R3, L A A and A are defined the same as in the general formula (1) above.

[0982] In the organic EL element involved in this embodiment, L is also preferred. A It is a single key.

[0983] In the organic EL element involved in this embodiment, in L A When the bond is a single bond, the compound of the above general formula (1) is represented by the following general formula (1-L1).

[0984]

Chemical Formula 53

[0985]

[0986] (In the above general formula (1-L1), X1, X2, X3, R1, R2, R3 and A are each defined in the same way as in the above general formula (1).)

[0987] In the organic EL element involved in this embodiment, L A It is also preferred to use divalent groups of the following general formulas (L1-1), (L1-2) or (L1-3).

[0988] [Chemical Formula 54]

[0989]

[0990] (In the above general formulas (L1-1), (L1-2), and (L1-3),

[0991] Y1 to Y6 are each independently a nitrogen atom or CR6.

[0992] R6 is

[0993] hydrogen atom,

[0994] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0995] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0996] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0997] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0998] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0999] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1000] -O-(R 904 The groups shown in the figure,

[1001] -S-(R 905 The groups shown in the figure,

[1002] -N(R 906 (R) 907 The groups shown in the figure,

[1003] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[1004] -C(=O)R 801 The groups shown

[1005] -COOR 802 The groups shown

[1006] Halogen atoms,

[1007] cyano,

[1008] Nitro,

[1009] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1010] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1011] When multiple R6s exist, these R6s may be identical or different.

[1012] * indicates the bonding location.

[1013] R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently

[1014] hydrogen atom,

[1015] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1016] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1017] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1018] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1019] In the existence of multiple R 901 In the case of multiple R 901 They are the same or different.

[1020] In the existence of multiple R 902 In the case of multiple R 902 They are the same or different.

[1021] In the existence of multiple R 903 In the case of multiple R 903 They are the same or different.

[1022] In the existence of multiple R 904In the case of multiple R 904 They are the same or different.

[1023] In the existence of multiple R 905 In the case of multiple R 905 They are the same or different.

[1024] In the existence of multiple R 906 In the case of multiple R 906 They are the same or different.

[1025] In the existence of multiple R 907 In the case of multiple R 907 They are the same or different.

[1026] In the existence of multiple R 801 In the case of multiple R 801 They are the same or different.

[1027] In the existence of multiple R 802 In the case of multiple R 802 (They may be the same or different.)

[1028] In the organic EL element involved in this embodiment, the compound of the above general formula (1) is preferably a compound of the following general formula (1-L2), (1-L3) or (1-L4).

[1029]

Chemical Formula 55

[1030]

[1031] (In the above general formulas (1-L2), (1-L3) and (1-L4), X1, X2, X3, R1, R2, R3 and A are each the same as defined in the above general formula (1), and Y1 to Y6 are the same as defined in the above general formulas (L1-1), (L1-2) and (L1-3).)

[1032] In the organic EL element involved in this embodiment, L A It is also preferred to use a divalent group of the above general formula (L1-1) or (L1-2).

[1033] In the organic EL element involved in this embodiment, L in the above general formula (A1-2) A When the divalent group is of the above general formula (L1-1), the compound of the above general formula (1) is represented by the following general formula (A1-L1).

[1034] [Chemical Formula 56]

[1035]

[1036] (In the above general formula (A1-L1),

[1037] X1~X3 and R1~R3 are each defined in the above general formula (1).

[1038] R 11 ~R 19 Each is independently identical to the definition in the general formula (A1-2) above.

[1039] Y1, Y2, Y4, and Y5 are each independently identical to the definitions in the general formula (L1-1) above.

[1040] In the organic EL element according to this embodiment, L in the above general formula (A1-1) A When the divalent group is of the above general formula (L1-2), the compound of the above general formula (1) is represented by the following general formula (A1-L2).

[1041] [Chemical Formula 57]

[1042]

[1043] (In the above general formula (A1-L2),

[1044] X1~X3 and R1~R3 are each defined in the above general formula (1).

[1045] R 11 R 12 R 14 ~R 20 Each is independently identical to the definition in the general formula (A1-1) above.

[1046] Y1, Y2, Y4, and Y6 are each independently identical to the definitions in the general formula (L1-2) above.

[1047] In the organic EL element involved in this embodiment, it is preferred that Y1 to Y6, which are not bonded positions, are CR6 and R6 is a hydrogen atom.

[1048] In the organic EL element involved in this embodiment, L A It is also preferred to use divalent groups of the following general formulas (L1-1H), (L1-2H) or (L1-3H).

[1049] [Chemical Formula 58]

[1050]

[1051] In the organic EL element involved in this embodiment, L A It is also preferred to use a divalent group of the above general formula (L1-1H) or (L1-2H).

[1052] In the organic EL element involved in this embodiment, in the compound of the above general formula (100), the groups described as "substituted or unsubstituted" are preferably all "unsubstituted" groups.

[1053] In the organic EL element involved in this embodiment, in the compound of the above general formula (1), the groups described as "substituted or unsubstituted" are preferably all "unsubstituted" groups.

[1054] The content of the compound of the above general formula (100) in the first layer is preferably 90% by mass or more, more preferably 95% by mass or more, and even more preferably 99% by mass or more. The first layer does not exclude materials other than the compound of the above general formula (100), but the first layer does not contain metal doped materials.

[1055] The first layer is preferably composed of compounds of general formula (100) only. "Indeed" means that it also contains trace amounts of impurities that inevitably mix in from the raw materials used to form the first layer.

[1056] The first layer is preferably composed only of compounds of the above general formula (100).

[1057] The content of the compound of the above general formula (1) in the first layer is preferably 90% by mass or more, more preferably 95% by mass or more, and even more preferably 99% by mass or more. The first layer does not exclude materials other than the compound of the above general formula (1), but the first layer does not contain metal doped materials.

[1058] The first layer is preferably composed of compounds of general formula (1) only. "Indeed" means that it also contains trace amounts of impurities that inevitably mix in from the raw materials used to form the first layer.

[1059] The first layer is preferably composed only of compounds of the above general formula (1).

[1060] (Methods for manufacturing compounds of general formula (100) and compounds of general formula (1))

[1061] The compounds of general formula (100) and general formula (1) can be manufactured by known methods. Alternatively, the compounds of general formula (100) and general formula (1) can also be manufactured by following known methods, using known alternative reactions and starting materials corresponding to the target substance.

[1062] (Specific examples of compounds of general formula (100) and compounds of general formula (1))

[1063] Specific examples of compounds of the above general formula (100) and compounds of the above general formula (1) include the following compounds. It should be noted that the present invention is not limited to these specific examples.

[1064] [Chemical Formula 59]

[1065]

[1066] [Chemical Formula 60]

[1067]

[1068]

Chemical Formula 61

[1069]

[1070]

Chemical Formula 62

[1071]

[1072]

Chemical Formula 63

[1073]

[1074]

Chemical Formula 64

[1075]

[1076]

Chemical Formula 65

[1077]

[1078]

Chemical Formula 66

[1079]

[1080] [Resonator Structure]

[1081] The organic EL element involved in this embodiment preferably has a resonator structure with an interference order of one level between the light-reflecting layer and the semi-transparent electrode serving as the cathode.

[1082] For example, in the case where the organic EL element 1 has a resonator structure with an interference order of first order, specifically, the organic EL element 1 has a resonator structure with an interference order of first order between the light-reflecting layer 31 and the semi-transparent electrode 4. The spacing D3 between the light-reflecting layer 31 and the semi-transparent electrode 4 in the organic EL element 1 is equivalent to the sum of the thickness of the hole transport region 6, the thickness of the light-emitting layer 5, and the thickness of the electron transport region 7. For organic EL elements 1A, 1B, and 1C, similarly to organic EL element 1, it is preferable to have a resonator structure with an interference order of first order.

[1083] The resonator structure in organic EL devices is described below.

[1084] By configuring the organic EL element as a resonator structure that allows the emitted light to resonate and be extracted between the light-reflecting layer 31 and the semi-transparent electrode 4, the color purity of the extracted light can be improved, and the intensity of the extracted light near the center wavelength of the resonance can be increased.

[1085] In a resonator structure where the reflective end face of the light-emitting layer 5 side of the light-reflecting layer 31 is designated as the first end face P1, the reflective end face of the light-emitting layer 5 side of the semi-transparent electrode 4 is designated as the second end face P2, and the organic layer (hole transport region 6, light-emitting layer 5, and electron transport region 7) is designated as the resonator, and the light generated in the light-emitting layer 5 resonates and is extracted from the second end face P2 side, the optical distance L between the first end face P1 and the second end face P2 of the resonator is set such that it satisfies the following mathematical formula (OP1). In practice, it is preferable to select the optical distance L such that it is the minimum positive value that satisfies the mathematical formula (OP1).

[1086]

Mathematical Formula 1

[1087]

[1088] The symbols in the above mathematical expression (OP1) are explained as follows.

[1089] L is the optical distance between the first end P1 and the second end P2.

[1090] Φ is the sum of the phase shift Φ1 of the reflected light generated at the first end P1 and the phase shift Φ2 of the reflected light generated at the second end P2 (Φ = Φ1 + Φ2), and the unit of phase shift is rad.

[1091] λ is the peak wavelength of the spectrum of the light to be extracted from the second end P2 side.

[1092] m is an integer that makes L positive, and m is equivalent to the interference order. When m is 1, the organic EL element has a resonator structure with an interference order of first order.

[1093] In the mathematical formula (OP1), L and λ only need to have the same units, for example, nm.

[1094] The optical distance L is the sum of the optical film thicknesses (=refractive index (n)×film thickness (d)) of the organic layer between the light-reflecting layer 31 and the semi-transparent electrode 4 (=n1d1+n2d2+···). It should be noted that, in reality, when light is reflected by the light-reflecting layer 31 and the semi-transparent electrode 4, the sum of the phase shifts Φ changes depending on the combination of the electrode materials and organic materials constituting the reflective interface.

[1095] In the organic EL element according to this embodiment, it is preferable to adjust the optical distance L1 between the maximum luminescence position of the luminescent layer 5 and the first end P1 to satisfy the following mathematical formula (OP2), and the optical distance L2 between the maximum luminescence position and the second end P2 to satisfy the following mathematical formula (OP3). Here, the maximum luminescence position refers to the position with the highest luminescence intensity in the luminescence region. For example, when luminescence occurs at both the interface on the light-reflecting layer 31 side of the luminescent layer 5 and the interface on the semi-transparent electrode 4 side, the maximum luminescence position is the interface with the higher luminescence intensity among these interfaces.

[1096]

Mathematical Formula 2

[1097]

[1098] The symbols in the above mathematical expression (OP2) are explained as follows.

[1099] tL1 is the theoretical optical distance between the first end P1 and the position of maximum emission.

[1100] a1 is a correction amount based on the light emission distribution in the light-emitting layer 5.

[1101] λ is the peak wavelength of the spectrum of the light to be extracted.

[1102] Φ1 is the phase shift of the reflected light generated at the first end P1, and the unit is rad.

[1103] m1 is 0 or an integer. In the organic EL element involved in this embodiment, m1 is preferably 0. The position of the optical distance L1 when m1 is 0 corresponds to the "0th order interference position" as observed from the light reflecting layer 31 side.

[1104]

Mathematical Expression 3

[1105]

[1106] The symbols in the above mathematical expression (OP3) are explained as follows.

[1107] tL2 is the theoretical optical distance between the second end P2 and the position of maximum emission.

[1108] a2 is a correction amount based on the light emission distribution in the light-emitting layer 5.

[1109] λ is the peak wavelength of the spectrum of the light to be extracted.

[1110] Φ2 is the phase shift of the reflected light generated at the second end P2, in rad.

[1111] m2 is 0 or an integer. m2 is preferably 1.

[1112] More preferably, m1 is 0 and m2 is 1. The position of the optical distance L2 when m2 is 1 corresponds to the "first-order interference position" observed from the side of the semi-transparent electrode 4.

[1113] The above mathematical formula (OP2) represents the condition for setting the following situation: when the light generated in the light-emitting layer 5 is reflected back at the first end P1, the phase of the returned light is the same as the phase when it is emitted, and it is mutually reinforcing with the light emitted towards the semi-transparent electrode 4.

[1114] In addition, the mathematical formula (OP3) indicates the condition for setting the following situation: when the light generated in the light-emitting layer 5 is reflected back at the second end P2, the phase of the returned light is the same as the phase when it is emitted, and it becomes mutually reinforcing with the light emitted towards the light-reflecting layer 31.

[1115] In the organic EL element of this embodiment, by making the film thickness of the electron transport region 7 thicker than the film thickness of the hole transport region 6, it is possible to design such that m1 and m2 in the above mathematical formulas (OP2) and (OP3) satisfy m2 > m1. By designing m2 > m1, the field of view of the organic EL element according to this embodiment can be improved.

[1116] It should be noted that, assuming no expansion of the luminous region, the theoretical optical distances tL1 in mathematical formula (OP2) and tL2 in mathematical formula (OP3) are theoretical values ​​where the phase change at the first end P1 or the second end P2 exactly cancels out the phase change caused by travel, and the phase of the returned light is the same as the phase of the emitted light. It should also be noted that, since the luminous region usually expands, correction values ​​a1 and a2 based on the luminous distribution are added to mathematical formulas (OP2) and (OP3).

[1117] The correction values ​​a1 and a2 vary depending on the light emission distribution. When the maximum light emission position is located on the side of the semi-transparent electrode 4 of the light emission layer 5 and the light emission distribution extends from the maximum light emission position to the side of the light reflection layer 31, or when the maximum light emission position is located on the side of the light reflection layer 31 of the light emission layer 5 and the light emission distribution extends from the maximum light emission position to the side of the semi-transparent electrode 4, the correction values ​​a1 and a2 can be calculated by the following mathematical formula (OP4).

[1118]

Mathematical Expression 4

[1119]

[1120] The symbols in the above mathematical expression (OP4) are explained as follows.

[1121] When the light emission distribution in the light-emitting layer 5 extends from the maximum light emission position toward the light-reflecting layer 31, b is a value in the range of 2n ≤ b ≤ 6n. When it extends from the maximum light emission position toward the semi-transparent electrode 4, b is a value in the range of -6n ≤ b ≤ -2n.

[1122] s is a physical property value (1 / e attenuation distance) related to the emission distribution in the luminescent layer 5.

[1123] n is the average refractive index between the first end P1 and the second end P2 of the peak wavelength λ of the spectrum of the light to be extracted.

[1124] The above is an explanation of the resonator structure in organic EL devices.

[1125] (Methods for measuring film thickness in layers or regions)

[1126] The thickness (film thickness) of each layer or region contained in an organic EL element can be measured as follows.

[1127] The central portion of an organic EL element containing the layer or region to be measured is cut along a direction perpendicular to the formation surface of the layer or region to be measured (i.e., the thickness direction of the organic layer). The cross-section of the central portion is observed using a transmission electron microscope (TEM) to measure the film thickness.

[1128] For example, when measuring the thickness of the light-emitting layer in an organic EL element, the central portion of the organic EL element, which has the layer to be measured, is cut along a direction perpendicular to the formation surface of the light-emitting layer (i.e., the thickness direction of the light-emitting layer). The cross-section of this central portion is observed using a transmission electron microscope (TEM) to measure the film thickness. The central portion of the organic EL element is... Figures 1-4 For example, it is represented by the symbol CL.

[1129] It should be noted that the center of an organic EL element refers to the center of the shape obtained by projecting the organic EL element from the semi-transparent electrode side. For example, when the projected shape is rectangular, it refers to the intersection of the diagonals of the rectangle.

[1130] In this specification, when the target area or layer is composed of multiple layers, the thickness refers to the sum of the thicknesses of the multiple layers.

[1131] (Light-reflecting layer)

[1132] The light-reflecting layer 31 is directly connected to the transparent electrode 32.

[1133] The reflectivity of the interface between the light-reflecting layer 31 and the transparent electrode 32 is preferably 50% or more, and more preferably 80% or more.

[1134] The light-reflecting layer 31 is preferably a metal layer. The metal constituting the metal layer is not particularly limited, and examples include metals selected from gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), and silver (Ag), as well as alloys containing two or more of these metals. For example, an APC layer can be used as the light-reflecting layer 31. APC is an alloy of silver (Ag), palladium (Pd), and copper (Cu). The materials that can be used for the light-reflecting layer 31 are not limited to the materials described above.

[1135] (Transparent electrode)

[1136] The transparent electrode 32 is contained between the light-reflecting layer 31 and the hole transport region 6.

[1137] The transparent electrode 32 is directly connected to the light-reflecting layer 31. Preferably, the transparent electrode 32 is directly connected to the hole transport region 6.

[1138] The transparent electrode 32 is preferably a transparent conductive film. Examples of transparent conductive films used as the transparent electrode 32 include indium tin oxide (ITO) films and indium zinc oxide films. Compounds that can be used for transparent electrodes are not limited to the compounds mentioned above.

[1139] The transmittance of the transparent electrode 32 is preferably 50% or more, more preferably 80% or more. The transmittance of the transparent electrode 32 is preferably 100% or less. From the viewpoint of suppressing attenuation caused by multiple reflections, the extinction coefficient of the transparent electrode 32 is preferably 0.05 or less, more preferably 0.01 or less.

[1140] The thickness of the transparent electrode 32 is preferably less than 15 nm.

[1141] The thickness of the transparent electrode 32 is preferably 5 nm or more.

[1142] The film thickness of the transparent electrode 32 can be measured using the "method for measuring the film thickness of a layer or region" described above. By making the film thickness of the transparent electrode 32 less than 15 nm, the film thickness of the hole transport region 6 can be increased while maintaining the sum of the film thicknesses of the hole transport region 6 and the transparent electrode 32 at less than 40 nm. By making the film thickness of the transparent electrode 32 greater than 5 nm, stable hole injection can be achieved.

[1143] (hole transport region)

[1144] The hole transport region 6 is at least contained between the transparent electrode 32 and the light-emitting layer 5.

[1145] The thickness of the hole transport region 6 is preferably 10 nm or more and less than 25 nm, more preferably 10 nm or more and less than 20 nm.

[1146] The film thickness of hole transport region 6 can be measured using the above-mentioned "method for measuring the film thickness of a layer or region".

[1147] In this embodiment, the sum of the film thicknesses of the transparent electrode 32 and the hole transport region 6 in the organic EL element is preferably less than 40 nm.

[1148] By making the sum of the film thicknesses of the transparent electrode 32 and the hole transport region 6 in the organic EL element involved in this embodiment less than 40 nm, the field of view can be improved.

[1149] In this embodiment, the sum of the film thicknesses of the transparent electrode 32 and the hole transport region 6 in the organic EL element is preferably 15 nm or more.

[1150] The hole transport region refers to the area where holes move. The hole mobility μ within the hole transport region... H Preferably 10 -6 [cm 2 / (V·s)] above. Hole mobility μ H [cm 2 [ / (V·s)] can be determined using the impedance spectroscopy method described in Japanese Patent Application Publication No. 2014-110348.

[1151] Hole transport region 6 is also preferably composed of only a single layer.

[1152] Hole transport region 6 is also preferably composed of multiple layers.

[1153] Examples of layers constituting the hole transport region 6 include a hole injection layer, a hole transport layer, and an electron blocking layer.

[1154] An example of an organic EL element described in this embodiment is shown. Figures 1-4 In the organic EL elements 1, 1A, 1B, and 1C shown, the hole transport region 6 includes a hole injection layer 61 and a hole transport layer 62.

[1155] (hole injection layer)

[1156] 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.

[1157] 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]triphenyl]biphenyl. 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).

[1158] In addition, high-molecular-weight compounds (oligomers, dendritic polymers, polymers, etc.) can also be used as materials 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.

[1159] Compounds that can be used in hole injection layers are not limited to the compounds mentioned above.

[1160] (Hole transport layer)

[1161] The hole transport layer is a layer containing substances with high hole transport capacity. 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.

[1162] 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.

[1163] Compounds that can be used in hole transport layers are not limited to those mentioned above.

[1164] It should be noted that in the hole transport layer, any material other than electrons can be used as long as its hole transport capability is higher than its electron transport capability. It should also be noted that the layer containing the material 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 materials stacked together.

[1165] (Emitting layer)

[1166] • Guest material of the luminescent layer

[1167] The luminescent layer is a layer containing a highly luminescent material, and various materials can be used. For example, fluorescent compounds that emit fluorescence or phosphorescent compounds that emit phosphorescence can be used as highly luminescent materials. Fluorescent compounds are compounds that emit light from a singlet excited state, while phosphorescent compounds are compounds that emit light from a triplet excited state. The guest material is sometimes also called a dopant material, emitter, or luminescent material.

[1168] As blue fluorescent materials suitable for use in the luminescent layer, pyrene derivatives, styrene amine derivatives, etc., can be used. Derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. Specifically, as blue fluorescent luminescent materials, examples include N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenyl succinyl-4,4'-diamine (abbreviated as YGA2S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthrayl)triphenylamine (abbreviated as YGAPA), and 4-(10-phenyl-9-anthrayl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCPAPA), etc.

[1169] As green fluorescent luminescent materials that can be used in the luminescent layer, aromatic amine derivatives can be used. Specifically, examples of green fluorescent luminescent materials include N-(9,10-diphenyl-2-anthrayl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthrayl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCABPhA), and N-(9,10-diphenyl-2-anthrayl)-N,N',N'-triphenyl-1,4-phenylenediamine (…). Abbreviations: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthrayl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracene-9-amine (abbreviation: DPhAPhA), etc.

[1170] As red-based fluorescent luminescent materials that can be used in the luminescent layer, tetraphenyl derivatives, diamine derivatives, etc., can be used. Specifically, examples of red-based fluorescent luminescent materials include N,N,N',N'-tetra(4-methylphenyl)tetraphenyl-5,11-diamine (abbreviated as p-mPhTD) and 7,14-diphenyl-N,N,N',N'-tetra(4-methylphenyl)acenaphthene[1,2-a]fluoranthene-3,10-diamine (abbreviated as p-mPhAFD).

[1171] As blue phosphorescent materials that can be used in the luminescent layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used. Specifically, examples of blue phosphorescent materials include bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III)tetra(1-pyrazolyl)borate (FIr6), bis[2-(4',6'-difluorophenyl)pyridin-N,C2']iridium(III)pyridinecarboxylate (FIrpic), bis[2-(3',5'-bistrifluoromethylphenyl)pyridin-N,C2']iridium(III)pyridinecarboxylate (Ir(CF3ppy)2(pic)), and bis[2-(4',6'-difluorophenyl)pyridin-N,C2']iridium(III)acetylacetone (FIracac).

[1172] As green phosphorescent materials that can be used in the luminescent layer, iridium complexes are used. Specifically, examples of green phosphorescent materials include tris(2-phenylpyridine-N,C2')iridium(III) (abbreviated as Ir(ppy)3), bis(2-phenylpyridine-N,C2')iridium(III)acetylacetonate (abbreviated as Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazole)iridium(III)acetylacetonate (abbreviated as Ir(pbi)2(acac)), and bis(benzo[h]quinoline)iridium(III)acetylacetonate (abbreviated as Ir(bzq)2(acac)).

[1173] As red-based phosphorescent materials that can be used in the luminescent layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are employed. Specifically, examples of red-based phosphorescent materials include bis[2-(2'-benzo[4,5-α]thienyl)pyridine-N,C3']iridium(III)acetylacetonate (abbreviated as Ir(btp)2(acac)), bis(1-phenylisoquinoline-N,C2')iridium(III)acetylacetonate (abbreviated as Ir(piq)2(acac)), (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviated as Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as PtOEP).

[1174] In addition, rare earth metal complexes such as tri(acetylacetonyl)(monophenanthrene)terbium(III) (abbreviated as Tb(acac)3(Phen)), tri(1,3-diphenyl-1,3-propanedione)(monophenanthrene)eupium(III) (abbreviated as Eu(DBM)3(Phen)), and tri[1-(2-thiophenecarboxyl)-3,3,3-trifluoroacetone](monophenanthrene)eupium(III) (abbreviated as Eu(TTA)3(Phen)) can be used as phosphorescent compounds because their luminescence originates from the luminescence of rare earth metal ions (electronic transitions between different multiplicity levels).

[1175] (Main material of the light-emitting layer)

[1176] As the luminescent layer, it can be configured to disperse the aforementioned highly luminescent substance (guest material) in other substances (host material). Various substances can be used as the substance for dispersing the highly luminescent substance, but it is preferable to use a substance with a lower unoccupied orbital energy level (LUMO level) higher than the highly luminescent substance and a higher occupied orbital energy level (HOMO level) lower than the highly luminescent substance.

[1177] In this specification, "main material" refers, for example, to a material with a content of "50% by mass or more of the layer". Alternatively, for example, the content of "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.

[1178] As a substrate material for a substance with high dispersion luminescence, the following are used: (1) metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes; (2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives; (3) carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or... Derivatives and other fused aromatic compounds, or (4) triarylamine derivatives, or fused polycyclic aromatic amine derivatives and other aromatic amine compounds.

[1179] Specifically, as metal complexes, tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-hydroxyquinoline)aluminum(III) (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium(II) (abbreviated as BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO), bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ), etc.

[1180] As heterocyclic compounds, specifically, 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-biphenyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviated as TAZ), 2,2',2”-(1,3,5-phenyltriyl)tris(1-phenyl-1H-benzimidazole) (abbreviated as TPBI), phenanthroline (abbreviated as BPhen), and copper bath (abbreviated as BCP) can be used.

[1181] As fused aromatic compounds, specifically, 9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (abbreviated as CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (abbreviated as DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviated as DPPA), 9,10-bis(2-naphthyl)anthracene (abbreviated as DNA), and 2-tert-butyl-9,10-di- (2-Naphthyl)anthracene (t-BuDNA), 9,9'-bianthracite (BANT), 9,9'-(stilbene-3,3'-diyl)phenanthrene (DPNS), 9,9'-(stilbene-4,4'-diyl)phenanthrene (DPNS2), 3,3',3”-(benzene-1,3,5-triyl)tripyrene (TPB3), 9,10-diphenylanthracene (DPAnth), 6,12-dimethoxy-5,11-diphenyl wait.

[1182] As aromatic amine compounds, specifically, N,N-diphenyl-9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole-3-amine (abbreviated as CzA1PA), 4-(10-phenyl-9-anthrayl)triphenylamine (abbreviated as DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole-3-amine (abbreviated as PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthrayl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviated as PCAPBA), N-(9,10-diphenyl-2-anthrayl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCAPA), NPB (or α-NPD), TPD, DFLDPBi, BSPB, etc. can be used.

[1183] In addition, two or more substances (host materials) can be used for substances with high dispersion luminescence (guest materials).

[1184] Compounds that can be used in the light-emitting layer are not limited to the compounds mentioned above.

[1185] In this specification, blue emission refers to emission in the range of wavelength of the main peak of the emission spectrum being above 430 nm and below 500 nm.

[1186] The main peak wavelength of the blue fluorescent compound is preferably above 430 nm and below 500 nm, more preferably above 430 nm and below 500 nm.

[1187] In this specification, green luminescence refers to luminescence whose main peak wavelength is above 500 nm and below 560 nm.

[1188] The main peak wavelength of the green fluorescent compound is preferably above 500 nm and below 560 nm, more preferably above 500 nm and below 540 nm, and even more preferably above 510 nm and below 530 nm.

[1189] In this specification, red emission refers to emission whose main peak wavelength is in the range of 600 nm or higher and 660 nm or lower.

[1190] The main peak wavelength of the red fluorescent compound is preferably above 600 nm and below 660 nm, more preferably above 600 nm and below 640 nm, and even more preferably above 600 nm and below 630 nm.

[1191] In this specification, the peak wavelength of the main peak refers to the wavelength at which the target compound is measured at 10 nm. -6 moles per liter and above and 10 -5The emission intensity of toluene solutions dissolved at concentrations below mol / L reached the peak wavelength of the emission spectrum. The measuring apparatus used was a spectrophotometer (Hitachi Advanced Scientific Corporation, F-7000).

[1192] It is also preferable that the light-emitting layer does not contain phosphorescent materials as dopants.

[1193] Furthermore, it is preferable that the luminescent layer 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.

[1194] In addition, it is preferable that the light-emitting layer does not contain metal complexes.

[1195] (Electronic transmission area)

[1196] The electron transport region 7 is at least contained between the light-emitting layer 5 and the semi-transparent electrode 4.

[1197] The electron transport region 7 is directly connected to the light-emitting layer 5 and also directly connected to the semi-transparent electrode 4.

[1198] The thickness of the electron transport region 7 is preferably 50 nm or more, more preferably 100 nm or more, and even more preferably 120 nm or more.

[1199] The thickness of the electron transport region 7 is preferably less than 160 nm.

[1200] The film thickness of the electron transport region can be measured using the "method for measuring the film thickness of a layer or region" described above.

[1201] Electron transport region 7 refers to the region where electrons move. The electron mobility μ in electron transport region 7... E Preferably 10 -6 [cm 2 [ / (V·s)] above. Electron mobility μ E [cm 2 [ / (V·s)] can be determined by impedance spectroscopy as described in Japanese Patent Application Publication No. 2014-110348.

[1202] The electron transport region 7 can be a single layer or multiple layers. That is, the electron transport region 7 in the organic EL element involved in this embodiment can be a region composed of a single layer or a region composed of multiple layers.

[1203] Examples of layers constituting the electron transport region 7 include an electron injection layer, an electron transport layer, and a hole blocking layer.

[1204] In the organic EL element involved in this embodiment, the first layer is preferably an electron transport layer.

[1205] In the organic EL element involved in this embodiment, the first layer is preferably a hole blocking layer.

[1206] In the organic EL element involved in this embodiment, the second layer is preferably an electron transport layer.

[1207] In the organic EL element involved in this embodiment, the second layer is preferably a hole blocking layer.

[1208] In the organic EL element involved in this embodiment, the third layer is preferably an electron transport layer.

[1209] In the organic EL element involved in this embodiment, the third layer is preferably an electron injection layer.

[1210] Preferably, the thickness of the second layer is thinner than that of the first layer.

[1211] The thickness of the second layer is preferably 3 nm or more, more preferably 4 nm or more, and even more preferably 5 nm or more.

[1212] The thickness of the second layer is preferably less than 20 nm, more preferably less than 15 nm, and even more preferably less than 10 nm.

[1213] Ideally, the thickness of the third layer should be thinner than that of the first layer.

[1214] The thickness of the third layer is preferably 3 nm or more, more preferably 4 nm or more, and even more preferably 5 nm or more.

[1215] The thickness of the third layer is preferably less than 20 nm, more preferably less than 15 nm, and even more preferably less than 10 nm.

[1216] To supplement the electron injection capability of the first layer, the third layer is preferably a layer containing an organic compound with a highly electron-injectable group. Examples of highly electron-injectable groups include azole groups, such as benzimidazole and triazole; azazin groups, such as pyridine and phenanthroline; phosphine oxide groups, such as diphenylphosphine oxide; and cyano groups.

[1217] Alternatively, the third layer is preferably an organic compound layer containing alkali metals, alkaline earth metals, alkali metal compounds, or alkaline earth metal compounds, as described in the electron injection layer section below.

[1218] Alternatively, the third layer preferably comprises a compound having at least one group selected from azole, azazinyl, phosphine oxide and cyano groups.

[1219] Compounds having a benzoxazole group are represented, for example, by the following general formula (70).

[1220] [Chemical Formula 67]

[1221]

[1222] (In the above general formula (70),

[1223] R 71 ~R 75 Each independently

[1224] hydrogen atom,

[1225] Alkyl groups, substituted or unsubstituted, having 1 or more carbon atoms and less than 50 carbon atoms

[1226] Substituted or unsubstituted aryl groups with 6 or more but less than 50 carbon atoms in the cyclic group, or

[1227] Heterocyclic groups with 5 or more but less than 50 cyclic atoms, whether substituted or unsubstituted.

[1228] L 71 for

[1229] Substituted or unsubstituted arylene groups with 6 or more but less than 50 carbon atoms in the cyclic group, or

[1230] A divalent heterocyclic group, with 5 or more but less than 50 cyclic atoms, whether substituted or unsubstituted.

[1231] Ar 71 for

[1232] Alkyl groups, substituted or unsubstituted, having 1 or more carbon atoms and less than 50 carbon atoms

[1233] Substituted or unsubstituted aryl groups with 6 or more but less than 50 carbon atoms in the cyclic group, or

[1234] (A heterocyclic group, substituted or unsubstituted, with 5 or more but less than 50 cyclic atoms.)

[1235] (Specific examples of compounds of general formula (70))

[1236] Specific examples of compounds of the above general formula (70) include the following compounds. It should be noted that the present invention is not limited to these specific examples.

[1237]

Chemical Formula 68

[1238]

[1239] The electron transport layer is a layer containing substances with high electron transport properties. Electron transport layers 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 (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (abbreviated as 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 bath (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)zirconia (abbreviated as BzOs) can also be used. In the organic EL element of this embodiment, a benzimidazole compound, for example, can be suitably used as the third layer of the electron transport layer. The materials described herein that can be used as electron transport layers primarily have a content of 10... -6 cm 2 Substances with an electron mobility of / (V·s) or higher. It should be noted that any substance whose electron transport capacity is higher than its hole transport capacity can be used as an electron transport layer, regardless of the specific substance mentioned above.

[1240] Alternatively, polymeric compounds can be used for 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.

[1241] (Electron injection layer)

[1242] The electron injection layer is a layer containing a material with high electron injection capacity. The electron injection layer can use alkali metals, alkaline earth metals, rare earth metals, compounds of alkali metals, compounds of alkaline earth metals, or compounds of rare earth metals, such as lithium (Li), cesium (Cs), calcium (Ca), ytterbium (Yb), lithium fluoride (LiF), lithium (8-hydroxyquinoline) (Liq), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx). Furthermore, the electron injection layer preferably contains a material with electron transport properties and alkali metals, alkaline earth metals, rare earth metals, compounds of alkali metals, compounds of alkaline earth metals, or compounds of rare earth metals. For example, a material containing magnesium (Mg) in Alq (Tris(8-hydroxyquinoline)aluminum) can be used as a combination of such an electron transport material and a metal or metal compound. It should be noted that when the electron injection layer contains an electron transport material and a metal or metal compound, electrons are efficiently injected from the cathode into the electron injection layer.

[1243] Alternatively, the electron injection layer can be a composite material formed by mixing an organic compound and an electron donor. Such a composite material generates electrons in the organic compound due to the electron donor, thus exhibiting excellent electron injection and electron transport properties. In this case, the organic compound is preferably a material that excels in transporting the generated electrons; specifically, substances constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) can be used, for example. 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 as electron donors; examples include lithium, cesium, magnesium, calcium, erbium, and ytterbium. Additionally, alkali metal oxides and alkaline earth metal oxides are preferred as electron donors; examples include lithium oxides, calcium oxides, and barium oxides. Furthermore, Lewis bases such as magnesium oxide can also be used as electron donors. Additionally, organic compounds such as tetrathiofulvalene (TTF) can also be used as electron donors.

[1244] Compounds that can be used in electron transport layers, electron injection layers, and light-emitting layers are not limited to the compounds mentioned above.

[1245] (Semi-transmissive electrode)

[1246] The semi-transparent electrode 4 transmits light and reflects light at the interface with the electron transport region 7. The transmittance of the semi-transparent electrode 4 is preferably 50% or more.

[1247] The film thickness of the semi-transparent electrode 4 is preferably 5 nm or more and 30 nm or less.

[1248] The semi-transparent electrode 4 is preferably made of a single element or alloy of metallic materials. In the case of metallic materials with a large extinction coefficient, the amount of transmitted light decreases due to light absorption when light passes through the semi-transparent electrode 4. To efficiently extract light from the semi-transparent electrode 4, it is preferable to suppress light absorption. Therefore, as the material for the semi-transparent electrode 4, a single element or alloy of a metallic material with a low real refractive index is preferably selected. Examples of metallic materials include silver, aluminum, magnesium, calcium, sodium, and gold. Materials that can be used for the semi-transparent electrode are not limited to the above-mentioned materials.

[1249] In the organic EL element according to this embodiment, a reflective electrode is constituted by at least a light-reflecting layer 31 and a transparent electrode 32. For example, the organic EL element according to this embodiment is a so-called top-emitting type organic EL element. The organic EL element according to this embodiment has a reflective electrode on the substrate 2, and extracts light from a semi-transparent electrode 4 on the opposite side, separated by an organic layer. In the organic EL element according to this embodiment, the reflective electrode is the anode, and the semi-transparent electrode 4 is the cathode.

[1250] (Capping layer)

[1251] The organic EL element involved in this embodiment may have a capping layer. The capping layer is preferably disposed on the upper part of the semi-transmissive electrode, which serves as the cathode, and preferably the capping layer is directly connected to the semi-transmissive electrode. Figures 1-4 The organic EL elements 1, 1A, 1B and 1C shown each have a capping layer 8.

[1252] When the organic EL element involved in this embodiment is a top-emitting type, it is preferable that the organic EL element has a capping layer.

[1253] Materials that can be used as capping layers include, for example, polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitrides, and silicon compounds (such as silicon oxides).

[1254] In addition, materials that can be used as capping layers include, for example, aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, and dibenzofuran derivatives. Compounds that can be used as capping layers are not limited to the above-mentioned compounds.

[1255] In addition, the organic EL element involved in this embodiment may have a laminate as a capping layer, which is formed by stacking multiple layers containing materials that can be used as a capping layer.

[1256] (Substrate)

[1257] Substrate 2 is a support for the organic EL element. Examples of materials for substrate 2 include glass, quartz, and plastic. Alternatively, a flexible substrate can be used as substrate 2. A flexible substrate is a substrate that can be bent (flexible). Examples of flexible substrates include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, or polyvinyl chloride. Furthermore, an inorganic vapor-deposited film can also be used as substrate 2.

[1258] (Layer thickness)

[1259] In the organic EL element according to this embodiment, the film thickness of each layer constituting the organic layer between the reflective electrode serving as the anode and the semi-transparent electrode 4 is not particularly limited except as specifically defined in this specification. Generally speaking, if the film thickness of each layer constituting the organic layer is too thin, defects such as pinholes are easily generated; if it is too thick, a high applied voltage is required, resulting in decreased efficiency. The film thickness of each layer constituting the organic layer is usually preferably in the range of a few nm to 1 μm.

[1260] (Layer formation method)

[1261] The method for forming each layer of the organic EL element according to this embodiment is not limited except as specifically mentioned above, and known methods such as dry film deposition or wet film deposition can be used. Examples of dry film deposition methods include vacuum evaporation, sputtering, plasma deposition, and ion plating. Examples of wet film deposition methods include spin coating, dip coating, flow coating, and inkjet coating.

[1262] According to this embodiment, an organic electroluminescent element that can be driven at low voltage even when no active metal is doped in the electron transport material of the thick-film electron transport region can be provided. The reasons are explained below.

[1263] Previously, in thick-film electron transport regions, doping the electron transport material with an active metal reduced the driving voltage of organic EL devices. However, the doping with the active metal caused problems in the following aspects (i) to (iv).

[1264] (i) The resistance of the electron transport region decreases, which makes it easy for leakage current to occur between adjacent pixels.

[1265] (ii) The diffusion of active metals leads to the deactivation of luminescence;

[1266] (iii) EL emission from organic materials colored by the interaction between metal and organic materials, or absorption of light emitted from the luminescent layer caused by such colored organic materials; and

[1267] (iv) Shortened lifetime due to excess electron supply from the electron transport region to the luminescent layer

[1268] In particular, while organic EL devices using the 0th order optical interference position (positions that reinforce each other) from the anode offer excellent field of view and luminous efficiency, they require thickening of the electron transport region. However, thickening the electron transport region can lead to an increase in the driving voltage of the organic EL device.

[1269] Although the first layer of the organic EL element in this embodiment has a thickness of 50 nm or more, is a thick film, and does not contain metal dopants, the organic EL element in this embodiment contains a compound represented by the above-described general formula (100) or a compound represented by the above-described general formula (1) in the first layer, and is driven at a low voltage. Furthermore, the organic EL element in this embodiment is driven at a low voltage without relying on the luminescent color of the luminescent layer. Additionally, according to one embodiment of the compound represented by the above-described general formula (100) or a compound represented by the above-described general formula (1), the electron transport region containing this compound can supplement electron injection from the cathode to the luminescent layer.

[1270] [Second Implementation]

[1271] (Electronic devices)

[1272] 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 panel modules), televisions, mobile phones, tablet computers, and personal computers. Examples of light-emitting devices include lighting and vehicle lamps.

[1273] [Variations on the implementation method]

[1274] 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 also included in the present invention.

[1275] For example, the light-emitting layer is not limited to one layer; there can be two or more light-emitting layers stacked together. In the case of an organic EL device having two or more light-emitting layers, each light-emitting layer can be, for example, a fluorescent light-emitting layer, or a phosphorescent light-emitting layer that emits light based on an electronic transition from a triplet excited state to the ground state.

[1276] 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 type organic EL element in which multiple light-emitting units are stacked with an intermediate layer between them.

[1277] Alternatively, a blocking layer may be disposed adjacent to at least one side of the light-emitting layer, on the anode side and the cathode side. The blocking layer is preferably disposed grounded with the light-emitting layer to block at least one of holes, electrons, and excitons.

[1278] 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.

[1279] Furthermore, when a blocking layer is grounded on the anode side of the light-emitting layer, this blocking layer transports holes and prevents electrons from reaching layers closer to the anode side than the blocking layer (e.g., hole transport layers). In the case of an organic EL device that includes a hole transport layer, it is preferable to include the blocking layer between the light-emitting layer and the hole transport layer.

[1280] 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).

[1281] Preferably, the light-emitting layer is bonded to the blocking layer.

[1282] 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.

[1283] Example

[1284] The embodiments of the present invention will now be described. The present invention is not limited to these embodiments in any way.

[1285] <Compound>

[1286] The following examples and comparative examples show compounds of general formula (100) or general formula (1) used in the manufacture of organic EL elements.

[1287]

Chemical Formula 69

[1288]

[1289] [Chemical Formula 70]

[1290]

[1291]

Chemical Formula 71

[1292]

[1293]

Chemical Formula 72

[1294]

[1295] The following examples and comparative examples illustrate the compounds used in the manufacture of organic EL elements.

[1296]

Chemical Formula 73

[1297]

[1298] The following shows the structures of other compounds used in the manufacture of the organic EL elements involved in the examples and comparative examples.

[1299] [Chemical Formula 74]

[1300]

[1301] [Chemical Formula 75]

[1302]

[1303] [Chemical Formula 76]

[1304]

[1305]

Chemical Formula 77

[1306]

[1307] [Chemical Formula 78]

[1308]

[1309] [Chemical Formula 79]

[1310]

[1311] <Fabrication of Organic EL Components 1>

[1312] The following describes the fabrication and evaluation of organic EL components.

[1313] (Example 1)

[1314] On a glass substrate (25mm × 75mm × 0.7mm thick) used for component fabrication, a 200nm thick silver (Ag) layer as a light-reflecting layer and a 10nm thick ITO (Indium Tin Oxide) layer as a transparent electrode are sequentially formed by sputtering. Thus, a lower electrode (anode) composed of the Ag layer and the ITO layer is formed.

[1315] Next, compounds HT1 and HA1 were co-deposited on the ITO layer of the anode to form a hole injection layer (HIL) with a thickness of 10 nm. The proportion of compound HT1 in the hole injection layer was set to 97% by mass, and the proportion of compound HA1 was set to 3% by mass.

[1316] Following the formation of the hole injection layer, compound HT2 was evaporated to form a hole transport layer (HTL) with a thickness of 10 nm.

[1317] Following the formation of the hole transport layer, compounds BH1 and BD1 were co-deposited, with BD1 accounting for 3% by mass, to form a light-emitting layer with a thickness of 20 nm.

[1318] Following the formation of the light-emitting layer, compound ET1 was vapor-deposited to form an electron transport layer (also known as a hole blocking layer) (ETL1) with a thickness of 140 nm.

[1319] Following the formation of the electron transport layer (ETL1), compound ET-A was evaporated to form an electron transport layer (ETL2) with a film thickness of 10 nm.

[1320] Following the formation of the electron transport layer (ETL2), LiF was deposited by vapor deposition to form an electron injection layer with a thickness of 1 nm.

[1321] Following the formation of the electron injection layer, Mg and Ag were co-deposited to form a semi-transparent upper electrode (cathode) made of MgAg alloy with a film thickness of 15 nm. The mixing ratio (film thickness ratio) of Mg to Ag in this upper electrode (cathode) was set to 15:85.

[1322] Compound Cap1 was deposited on the upper electrode to form a capping layer with a thickness of 65 nm.

[1323] The organic EL element described in Example 1 was fabricated in accordance with the above method.

[1324] The simplified component configuration of Embodiment 1 is shown below.

[1325] Ag(200) / ITO(10) / HT1:HA1(10,97%:3%) / HT2(10) / BH1:BD1(20,97%:3%) / ET1(140) / ET-A(10) / LiF(1) / Mg:Ag(15) / Cap1(65)

[1326] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[1327] Similarly, the percentage figures (97% : 3%) shown in parentheses indicate the ratio (mass %) of compound HT1 to compound HA1 in the hole injection layer, or the ratio (mass %) of compound BH1 to compound BD1 in the emissive layer. The element configuration is sometimes similarly simplified below.

[1328] (Examples 2-6)

[1329] The organic EL elements of Examples 2 to 6 were fabricated in the same manner as those of Example 1, except that the electron transport layer (ETL1) in Example 1 was replaced with the electron transport layer (ETL1) described in Table 1.

[1330] (Example 7)

[1331] The organic EL element of Example 7 was fabricated in the same manner as in Example 1, except that after the formation of the electron transport layer (ETL1) in Example 1, compounds ET1 and Liq were co-deposited to form an electron transport layer (ETL2) with a thickness of 10 nm. In Example 7, the proportion of compound ET1 in the electron transport layer (ETL2) was set to 50% by mass, and the proportion of Liq was set to 50% by mass. It should be noted that Liq is an abbreviation for (8-hydroxyquinoline)lithium.

[1332] (Examples 8-10)

[1333] The organic EL elements of Examples 8 to 10 were fabricated in the same manner as those of Example 1, except that the electron transport layer (ETL1) in Example 1 was replaced with the electron transport layer (ETL1) described in Table 1.

[1334] (Comparative Example 1)

[1335] The organic EL element of Comparative Example 1 was fabricated in the same manner as in Example 1, except that after forming the light-emitting layer in Example 1, the compound ET-A was deposited to form an electron transport layer (ETL1) with a film thickness of 150 nm, no electron transport layer (ETL2) was formed, and LiF was deposited after forming the electron transport layer (ETL1).

[1336] (Comparative Example 2)

[1337] The organic EL element of Comparative Example 2 was fabricated in the same manner as in Example 1, except that after forming the light-emitting layer in Example 1, compound ET-A and Liq were co-deposited to form an electron transport layer (ETL1) with a thickness of 140 nm, and after forming the electron transport layer (ETL1), compound ET-A was deposited to form an electron transport layer (ETL2) with a thickness of 10 nm. The proportion of compound ET-A in the electron transport layer (ETL1) of Comparative Example 2 was set to 50% by mass, and the proportion of Liq was set to 50% by mass.

[1338] <Evaluation of Organic EL Components 1>

[1339] The organic EL elements fabricated were evaluated as follows. The evaluation results are shown in Table 1.

[1340] • Drive voltage

[1341] A current density of 10 mA / cm² is applied between the anode and cathode. 2 Measure the voltage at this time (unit: V).

[1342] • Peak wavelength λp during component driving

[1343] Applying a voltage to the device results in a current density of 10 mA / cm² for the organic EL device. 2 The spectroradiance spectrum at this time was measured using a CS-2000 spectroradiance meter (manufactured by Konica Minolta Co., Ltd.). Based on the obtained spectroradiance spectrum, the peak wavelength λp (unit: nm) of the main peak was determined.

[1344] Table 1

[1345]

[1346] <Fabrication of Organic EL Components 2>

[1347] (Example 11)

[1348] On a glass substrate (25mm × 75mm × 0.7mm thick) used for component fabrication, a 200nm thick silver (Ag) layer as a light-reflecting layer and a 10nm thick ITO (Indium Tin Oxide) layer as a transparent electrode are sequentially formed by sputtering. Thus, a lower electrode (anode) composed of the Ag layer and the ITO layer is formed.

[1349] Next, compounds HT1 and HA1 were co-deposited on the ITO layer of the anode to form a hole injection layer (HIL) with a thickness of 10 nm. The proportion of compound HT1 in the hole injection layer was set to 97% by mass, and the proportion of compound HA1 was set to 3% by mass.

[1350] Following the formation of the hole injection layer, compound HT2 was evaporated to form a hole transport layer (HTL) with a thickness of 10 nm.

[1351] Following the formation of the hole transport layer, compounds BH1 and BD1 were co-deposited, with BD1 accounting for 3% by mass, to form a light-emitting layer with a thickness of 20 nm.

[1352] Following the formation of the light-emitting layer, compound ET-B was evaporated to form an electron transport layer (also known as a hole blocking layer) (ETL3) with a thickness of 10 nm.

[1353] Following the formation of the electron transport layer (ETL3), compound ET2 was evaporated to form an electron transport layer (ETL1) with a film thickness of 130 nm.

[1354] Following the formation of the electron transport layer (ETL1), compound ET-A was evaporated to form an electron transport layer (ETL2) with a film thickness of 10 nm.

[1355] Following the formation of the electron transport layer (ETL2), LiF was deposited by vapor deposition to form an electron injection layer with a thickness of 1 nm.

[1356] Following the formation of the electron injection layer, Mg and Ag were co-deposited to form a semi-transparent upper electrode (cathode) of MgAg alloy with a film thickness of 15 nm. The mixing ratio (film thickness ratio) of Mg to Ag in this upper electrode (cathode) was set to 15:85.

[1357] The compound Capl was vapor-deposited on the upper electrode to form a capping layer with a thickness of 65 nm.

[1358] The organic EL element involved in Example 11 was fabricated in accordance with the above method.

[1359] The simplified component configuration of Embodiment 11 is shown below.

[1360] Ag(200) / ITO(10) / HT1:HA1(10,97%:3%) / HT2(10) / BH1:BD1(20,97%:3%) / ET-B(10) / ET2(130) / ET-A(10) / LiF(1) / Mg:Ag(15) / Cap1(65)

[1361] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[1362] Similarly, the percentage figures (97% : 3%) shown in parentheses indicate the ratio (mass %) of compound HT1 to compound HA1 in the hole injection layer, or the ratio (mass %) of compound BH1 to compound BD1 in the emissive layer. The element configuration is sometimes similarly simplified below.

[1363] <Evaluation of Organic EL Components 2>

[1364] The organic EL elements fabricated were evaluated as follows. The evaluation results are shown in Table 2. Table 2 also reiterates the evaluation results of Comparative Example 1 and Comparative Example 2.

[1365] • Drive voltage

[1366] A current density of 10 mA / cm² is applied between the anode and cathode. 2 Measure the voltage at this time (unit: V).

[1367] • Peak wavelength λp during component driving

[1368] The peak wavelength λp (in nm) of the main peak was measured in the same manner as in the above <Evaluation of Organic EL Elements 1>.

[1369] Table 2

[1370]

[1371] <Fabrication of Organic EL Components 3>

[1372] (Example 12)

[1373] On a glass substrate (25mm × 75mm × 0.7mm thick) used for component fabrication, a 200nm thick silver (Ag) layer as a light-reflecting layer and a 10nm thick ITO (Indium Tin Oxide) layer as a transparent electrode are sequentially formed by sputtering. Thus, a lower electrode (anode) composed of the Ag layer and the ITO layer is formed.

[1374] Next, compounds HT1 and HA1 were co-deposited on the ITO layer of the anode to form a hole injection layer (HIL) with a thickness of 10 nm. The proportion of compound HT1 in the hole injection layer was set to 97% by mass, and the proportion of compound HA1 was set to 3% by mass.

[1375] Following the formation of the hole injection layer, compound HT2 was evaporated to form a hole transport layer (HTL) with a thickness of 10 nm.

[1376] Following the formation of the hole transport layer, compounds GH1, GH2, and Ir(ppy)3 were co-deposited to form a 40 nm thick emissive layer. The proportions of GH1, GH2, and Ir(ppy)3 in the emissive layer were set to 45% by mass, 50% by mass, and 5% by mass.

[1377] Following the formation of the light-emitting layer, compound ET1 was vapor-deposited to form an electron transport layer (also known as a hole blocking layer) (ETL1) with a thickness of 180 nm.

[1378] Following the formation of the electron transport layer (ETL1), compound ET-A was evaporated to form an electron transport layer (ETL2) with a film thickness of 10 nm.

[1379] Following the formation of the electron transport layer (ETL2), LiF was deposited by vapor deposition to form an electron injection layer with a thickness of 1 nm.

[1380] Following the formation of the electron injection layer, Mg and Ag were co-deposited to form a semi-transparent upper electrode (cathode) of MgAg alloy with a film thickness of 15 nm. The mixing ratio (film thickness ratio) of Mg to Ag in this upper electrode (cathode) was set to 15:85.

[1381] Compound Cap1 was deposited on the upper electrode to form a capping layer with a thickness of 65 nm.

[1382] The organic EL element involved in Example 12 was fabricated in accordance with the above method.

[1383] The component configuration of Example 12 is shown in a simplified manner as follows.

[1384] Ag(200) / ITO(10) / HT1:HA1(10,97%:3%) / HT2(10) / GH1:GH2:Ir(ppy)3(40,45%:50%:5%) / ET1(180) / ET-A(10) / LiF(1) / Mg:Ag(15) / Cap1(65)

[1385] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[1386] Similarly, within parentheses, the percentages (97% : 3%) represent the ratio (mass %) of compound HT1 to compound HA1 in the hole injection layer, and the percentages (45% : 50% : 5%) represent the ratio (mass %) of compound GH1 to compound GH2 to Ir(ppy)3 in the emissive layer. The element configuration is sometimes similarly simplified below.

[1387] (Example 13)

[1388] The organic EL element of Example 13 was fabricated in the same manner as that of Example 12, except that the electron transport layer (ETL1) in Example 12 was replaced with the electron transport layer (ETL1) described in Table 3.

[1389] (Comparative Example 3)

[1390] The organic EL element of Comparative Example 3 was fabricated in the same manner as in Example 12, except that after forming the light-emitting layer in Example 12, compound ET-A was deposited to form an electron transport layer (ETL1) with a film thickness of 190 nm, no electron transport layer (ETL2) was formed, and LiF was deposited after forming the electron transport layer (ETL1).

[1391] <Evaluation of Organic EL Components 3>

[1392] The organic EL elements fabricated were evaluated as follows. The evaluation results are shown in Table 3.

[1393] • Drive voltage

[1394] A current density of 10 mA / cm² is applied between the anode and cathode. 2 Measure the voltage at this time (unit: V).

[1395] • Peak wavelength λp during component driving

[1396] The peak wavelength λp (in nm) of the main peak was measured in the same manner as in the above <Evaluation of Organic EL Elements 1>.

[1397] Table 3

[1398]

[1399] <Fabrication of Organic EL Components 4>

[1400] (Example 14)

[1401] On a glass substrate (25mm × 75mm × 0.7mm thick) used for component fabrication, a 200nm thick silver (Ag) layer as a light-reflecting layer and a 10nm thick ITO (Indium Tin Oxide) layer as a transparent electrode are sequentially formed by sputtering. Thus, a lower electrode (anode) composed of the Ag layer and the ITO layer is formed.

[1402] Next, compounds HT1 and HA1 were co-deposited on the ITO layer of the anode to form a hole injection layer (HIL) with a thickness of 10 nm. The proportion of compound HT1 in the hole injection layer was set to 97% by mass, and the proportion of compound HA1 was set to 3% by mass.

[1403] Following the formation of the hole injection layer, compound HT2 was evaporated to form a hole transport layer (HTL) with a thickness of 10 nm.

[1404] Following the formation of the hole transport layer, compounds RH1 and RD1 were co-deposited to form a 40 nm thick emissive layer. The proportion of compound RH1 in the emissive layer was set to 95% by mass, and the proportion of compound RD1 was set to 5% by mass.

[1405] Following the formation of the light-emitting layer, compound ET1 was vapor-deposited to form an electron transport layer (also known as a hole blocking layer) (ETL1) with a thickness of 220 nm.

[1406] Following the formation of the electron transport layer (ETL1), compound ET-A was evaporated to form an electron transport layer (ETL2) with a film thickness of 10 nm.

[1407] Following the formation of the electron transport layer (ETL2), LiF was deposited by vapor deposition to form an electron injection layer with a thickness of 1 nm.

[1408] Following the formation of the electron injection layer, Mg and Ag were co-deposited to form a semi-transparent upper electrode (cathode) of MgAg alloy with a film thickness of 15 nm. The mixing ratio (film thickness ratio) of Mg to Ag in this upper electrode (cathode) was set to 15:85.

[1409] Compound Cap1 was deposited on the upper electrode to form a capping layer with a thickness of 65 nm.

[1410] The organic EL element involved in Example 14 was fabricated in accordance with the above method.

[1411] The simplified component configuration of Example 14 is shown below.

[1412] Ag(200) / ITO(10) / HT1:HA1(10,97%:3%) / HT2(10) / RH1:RD1(40,95%:5%) / ET1(220) / ET-A(10) / LiF(1) / Mg:Ag(15) / Cap1(65)

[1413] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[1414] Similarly, within parentheses, the percentage figures (97% : 3%) represent the ratio (mass %) of compound HT1 to compound HA1 in the hole injection layer, and the percentage figures (95% : 5%) represent the ratio (mass %) of compound RH1 to compound RD1 in the emissive layer. The element configuration is sometimes similarly simplified below.

[1415] (Example 15)

[1416] The organic EL element of Example 15 was fabricated in the same manner as that of Example 14, except that the electron transport layer (ETL1) in Example 14 was replaced with the electron transport layer (ETL1) described in Table 4.

[1417] (Comparative Example 4)

[1418] The organic EL element of Comparative Example 4 was fabricated in the same manner as in Example 14, except that after the formation of the light-emitting layer in Example 14, compound ET-A was deposited to form an electron transport layer (ETL1) with a film thickness of 190 nm, no electron transport layer (ETL2) was formed, and LiF was deposited after the formation of the electron transport layer (ETL1).

[1419] <Evaluation of Organic EL Components 4>

[1420] The organic EL elements fabricated were evaluated as follows. The evaluation results are shown in Table 4.

[1421] • Drive voltage

[1422] A current density of 10 mA / cm² is applied between the anode and cathode. 2 Measure the voltage at this time (unit: V).

[1423] • Peak wavelength λp during component driving

[1424] The peak wavelength λp (in nm) of the main peak was measured in the same manner as in the above <Evaluation of Organic EL Elements 1>.

[1425] Table 4

[1426]

[1427] Symbol Explanation

[1428] 1, 1A, 1B, 1C… Organic EL element, 2… Substrate, 3… Anode, 4… Semi-transparent electrode, 5… Light-emitting layer, 6… Hole transport region, 7, 7A, 7B, 7C… Electron transport region, 8… Capping layer, 10… Organic layer, 31… Light-reflecting layer, 32… Transparent electrode, 61… Hole injection layer, 62… Hole transport layer, 71… First layer, 72… Electron injection layer, 73… Second layer, 74… Third layer, P1… First end, P2… Second end.

Claims

1. An organic electroluminescent element, comprising an organic electroluminescent element having a light-emitting layer between an anode and a cathode, A first layer serving as an electron transport layer is located between the cathode and the light-emitting layer. The thickness of the first layer is greater than 70 nm and less than 160 nm. The first layer comprises compounds of the following general formula (B1). The first layer contains at least 90% by mass of the compound of general formula (B1). A third layer, serving as an electron transport layer, is also present between the cathode and the first layer. The thickness of the third layer is greater than 3nm and less than 20nm. The third layer comprises compounds having at least one group selected from azole, azazinyl, phosphine oxide, and cyano groups. An electron injection layer is further included between the cathode and the light-emitting layer, wherein the first layer, the third layer, and the electron injection layer are sequentially disposed. in, The first layer does not contain any metal doped material. The metal-doped material is a metal, metal compound, or metal complex with a work function below 4.2 eV. In the general formula (B1), L A It is a single key. X1, X2, and X3 are nitrogen atoms. R1 and R2 are each independently a hydrogen atom, phenyl, para-phenyl, meta-phenyl, o-phenyl, 1-naphthyl, or 2-naphthyl. R 21 ~R 28 One of them is related to L A The bonding position* Not with L A The bonding position of R 21 ~R 28 Each independently hydrogen atom, Unsubstituted alkyl groups having 1 to 6 carbon atoms Unsubstituted cycloalkyl groups with 3 to 6 carbon atoms Unsubstituted aralkyl groups with 7 to 18 carbon atoms cyano, or Unsubstituted aryl groups with 6 to 18 carbon atoms, Group consisting of R4 and R5 They bond together to form unsubstituted fused rings, or They do not bond with each other. R4 and R5, which do not form the unsubstituted fused ring, are each independently... hydrogen atom, Unsubstituted alkyl groups having 1 to 6 carbon atoms, or Unsubstituted aryl groups with 6 to 18 carbon atoms in a cyclic ring.

2. The organic electroluminescent element according to claim 1, wherein, R4 and R5 are each independently an unsubstituted aryl group with 6 to 18 cyclic carbon atoms.

3. The organic electroluminescent element according to claim 1 or 2, wherein, R4 and R5 are each an unsubstituted phenyl group.

4. The organic electroluminescent element according to claim 1, wherein, The compound of general formula (B1) is a compound of the following general formula (B1-1). In the general formula (B1-1), X1~X3, R1, R2 and L A Each of them is the same as the definition in the general formula (B1). R 21 ~R 28 Each of them is the same as the definition in the general formula (B1). Ring B is an unsubstituted fused ring.

5. The organic electroluminescent element according to claim 4, wherein, Ring B is an unsubstituted aromatic hydrocarbon ring or an unsubstituted aromatic heterocycle.

6. The organic electroluminescent element according to claim 1 or 4, wherein, The compound of general formula (B1) is a compound of the following general formula (B1-1A). In the general formula (B1-1A), X1~X3, R1, R2 and L A Each of them is the same as the definition in the general formula (B1). R 21 ~R 28 Each of them is the same as the definition in the general formula (B1). Ring B1 and ring B2 are each independently an unsubstituted monocyclic ring or an unsubstituted fused ring.

7. The organic electroluminescent element according to claim 6, wherein, Ring B1 and ring B2 are each independently an unsubstituted aromatic hydrocarbon ring or an unsubstituted aromatic heterocycle.

8. The organic electroluminescent element according to claim 1 or 4, wherein, The compound of general formula (B1) is a compound of the following general formula (B1-2). In the general formula (B1-2), X1~X3, R1, R2 and L A Each of them is the same as the definition in the general formula (B1). R 21 ~R 28 Each of them is the same as the definition in the general formula (B1). R 211 ~R 218 It is a hydrogen atom.

9. The organic electroluminescent element according to claim 1 or 2, wherein, R 21 or R 28 To be with L A The bonding position*.

10. The organic electroluminescent element according to claim 1 or 2, wherein, R 22 or R 27 To be with L A The bonding position*.

11. The organic electroluminescent element according to claim 1 or 2, wherein, R 23 or R 26 To be with L A The bonding position*.

12. The organic electroluminescent element according to claim 1 or 2, wherein, R 24 or R 25 To be with L A The bonding position*.

13. The organic electroluminescent element according to claim 1 or 2, wherein, The compounds of general formula (B1) are represented by the following general formula (B1-3). In the general formula (B1-3), X1~X3, R1, R2 and L A Each of them is the same as the definition in the general formula (B1). R4, R5, R 21 ~R 24 and R 26 ~R 28 Each of them is the same as the definition in the general formula (B1).

14. The organic electroluminescent element according to claim 1 or 2, wherein, R1 and R2 are each independently phenyl or paraphenyl.

15. The organic electroluminescent element according to claim 1 or 2, wherein, The compound of general formula (B1) in the first layer contains more than 95% by mass.

16. The organic electroluminescent element according to claim 1 or 2, wherein, The compound of general formula (B1) in the first layer contains more than 99% by mass.

17. The organic electroluminescent element according to claim 1 or 2, wherein, The first layer consists only of compounds of the general formula (B1).

18. The organic electroluminescent element according to claim 1 or 2, wherein, The distance D1 between the interface of the cathode on the light-emitting layer side and the interface of the light-emitting layer on the cathode side is greater than the distance D2 between the interface of the anode on the light-emitting layer side and the interface of the light-emitting layer on the anode side.

19. The organic electroluminescent element according to claim 1 or 2, wherein, The thickness of the first layer is more than 100 nm.

20. The organic electroluminescent element according to claim 1 or 2, wherein, The thickness of the first layer is 120 nm or more.

21. The organic electroluminescent element according to claim 1 or 2, wherein, The thickness of the first layer is less than 150 nm.

22. The organic electroluminescent element according to claim 1 or 2, wherein, The thickness of the first layer is greater than the thickness of the layers other than the first layer disposed between the cathode and the light-emitting layer.

23. The organic electroluminescent element according to claim 1 or 2, wherein, The metal doping material is an alkali metal, an alkaline earth metal, a transition metal including a rare earth metal, a compound containing the alkali metal, a compound containing the alkaline earth metal, a compound containing the transition metal, a complex containing the alkali metal, a complex containing the alkaline earth metal, and a complex containing the transition metal.

24. The organic electroluminescent element according to claim 1 or 2, wherein, The metal doping materials are lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), calcium (Ca), strontium (Sr), barium (Ba), cesium carbonate, and Liq.

25. The organic electroluminescent element according to claim 1 or 2, wherein, The light-emitting layer is directly connected to the first layer.

26. The organic electroluminescent element according to claim 1 or 2, wherein, A second layer is also present between the light-emitting layer and the first layer. The thickness of the second layer is more than 3nm and less than 20nm.

27. The organic electroluminescent element according to claim 26, wherein, The thickness of the second layer is 4 nm or more.

28. The organic electroluminescent element according to claim 26, wherein, The thickness of the second layer is 5 nm or more.

29. The organic electroluminescent element according to claim 26, wherein, The thickness of the second layer is less than 15 nm.

30. The organic electroluminescent element according to claim 26, wherein, The thickness of the second layer is less than 10 nm.

31. The organic electroluminescent element according to claim 1 or 2, wherein, The thickness of the third layer is 4 nm or more.

32. The organic electroluminescent element according to claim 1 or 2, wherein, The thickness of the third layer is greater than 5 nm.

33. The organic electroluminescent element according to claim 1 or 2, wherein, The thickness of the third layer is less than 15 nm.

34. The organic electroluminescent element according to claim 1 or 2, wherein, The thickness of the third layer is less than 10 nm.

35. The organic electroluminescent element according to claim 1 or 2, wherein, The third layer is an organic compound layer containing alkali metals, alkaline earth metals, alkali metal compounds, or alkaline earth metal compounds.

36. The organic electroluminescent element according to claim 1 or 2, wherein, The cathode is a semi-transmissive electrode. The anode comprises a light-reflecting layer and a transparent electrode.

37. The organic electroluminescent element according to claim 36, wherein, The electron transport region is at least contained between the light-emitting layer and the semi-transparent electrode. The electron transport region comprises the first layer, the third layer, and the electron injection layer. The electron transport region is directly connected to the light-emitting layer and also directly connected to the semi-transparent electrode.

38. The organic electroluminescent element according to claim 37, wherein, The thickness of the electron transport region is greater than 100 nm.

39. The organic electroluminescent element according to claim 37, wherein, The thickness of the electron transport region is 120 nm or more.

40. The organic electroluminescent element according to claim 37, wherein, The thickness of the electron transport region is less than 160 nm.

41. The organic electroluminescent element according to claim 36, wherein, The thickness of the transparent electrode is less than 15 nm.

42. The organic electroluminescent element according to claim 36, wherein, The thickness of the transparent electrode is 5 nm or more.

43. The organic electroluminescent element according to claim 36, wherein, The hole transport region is at least contained between the transparent electrode and the light-emitting layer. The thickness of the hole transport region is greater than 10 nm and less than 25 nm.

44. The organic electroluminescent element according to claim 43, wherein, The thickness of the hole transport region is greater than 10 nm and less than 20 nm.

45. The organic electroluminescent element according to claim 43, wherein, The sum of the film thicknesses of the transparent electrode and the hole transport region is less than 40 nm.

46. ​​The organic electroluminescent element according to claim 43, wherein, The combined thickness of the transparent electrode and the hole transport region is greater than 15 nm.

47. The organic electroluminescent element according to claim 1 or 2, wherein, The light-emitting layer comprises a host material and a guest material.

48. The organic electroluminescent element according to claim 36, wherein, The capping layer is disposed on the upper part of the semi-transparent electrode.

49. The organic electroluminescent element according to claim 1, wherein, The first layer is an electron transport layer ETL1, which contains either ET4 or ET8. 。 50. The organic electroluminescent element according to claim 49, wherein, The third layer is disposed between the first layer and the cathode. The third layer is the electronic transport layer ETL2. The electron transport layer ETL2 contains the following compound, ET-A. 。 51. The organic electroluminescent element according to claim 49, wherein, The third layer is disposed between the first layer and the cathode. The third layer is the electronic transport layer ETL2. The electron transport layer ETL2 comprises the following compound ET1 and (8-hydroxyquinoline) lithium. 。 52. The organic electroluminescent element according to claim 49, wherein, A second layer is disposed between the first layer and the light-emitting layer. The second layer is the electron transport layer ETL3. The electron transport layer ETL3 contains the following compound, ET-B. 。 53. An electronic device comprising an organic electroluminescent element according to any one of claims 1 to 52.

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