Organic electroluminescent element and electronic device

Abstract

The present application relates to organic electroluminescence element and electronic equipment. Organic electroluminescence element, it has cathode, anode, and the at least 1 layer light-emitting layer of configuration between preceding cathode and preceding anode, preceding light-emitting layer includes the 1st host material, the 2nd host material and dopant material, preceding 1st host material is the compound shown in formula (1) described below, preceding 2nd host material is the compound shown in formula (2) described below, selected from the compound shown in formula (1) and formula (2) compound in 1 or more has at least 1 deuterium atom.

Description

[0001] This invention application is a divisional application of PCT patent application PCT / JP2020 / 048967, filed on December 25, 2020, entitled "Organic Electroluminescent Element and Electronic Device". The parent application number in China is 202080056770.1. Technical Field

[0002] This invention relates to organic electroluminescent elements and electronic devices. Background Technology

[0003] When a voltage is applied to an organic electroluminescent element (hereinafter referred to as an organic EL element), holes are injected into the light-emitting layer from the anode and electrons from the cathode, respectively. Subsequently, in the light-emitting layer, the injected holes and electrons recombine to form excitons.

[0004] To improve the performance of organic EL devices, the device materials have been modified. Furthermore, attempts have been made to utilize the unique properties of each material by combining two or more materials in a single organic layer. For example, Patent Document 1 discloses a technique for combining two host materials in a light-emitting layer.

[0005] Existing technical documents

[0006] Patent documents

[0007] [Patent Document 1] Japanese Patent Application Publication No. 2015-18883. Summary of the Invention

[0008] However, even when using a combination of multiple materials, it is not always possible to maintain the strengths of each material. Sometimes, the expected improvement is not found, or the performance is even reduced. There is still room for improvement in the technology for improving the performance of organic EL devices based on this method.

[0009] The purpose of this invention is to provide organic EL devices with low driving voltage, high external quantum efficiency, and long lifetime.

[0010] The inventors, through careful research to achieve the above-mentioned objectives, discovered that by combining two compounds (a first host material and a second host material) having specific structures and at least one of which contains deuterium in the light-emitting layer of an organic EL element, an organic EL element with low driving voltage, high external quantum efficiency, and long device lifetime is obtained, thereby completing the present invention.

[0011] According to the present invention, the following organic EL elements, etc., are provided.

[0012] 1. Organic electroluminescent devices, which have a cathode,

[0013] anode, and

[0014] At least one light-emitting layer disposed between the aforementioned cathode and the aforementioned anode,

[0015] The aforementioned light-emitting layer comprises a first host material, a second host material, and a dopant material.

[0016] The aforementioned first main material is a compound represented by the following formula (1).

[0017] The aforementioned second main material is a compound represented by the following formula (2).

[0018] One or more of the compounds selected from the compounds shown in formula (1) and formula (2) above have at least one deuterium atom.

[0019] [Chemistry 1]

[0020]

[0021] In formula (1),

[0022] R 1A ~R 8A Each independently

[0023] hydrogen atom,

[0024] Substituent R, or

[0025] The group represented by the following formula (1A).

[0026] The aforementioned substituent R is

[0027] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0028] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[0029] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[0030] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0031] -Si(R 901 (R) 902 (R) 903 ),

[0032] -O-(R 904 ),

[0033] -S-(R 905 ),

[0034] -N(R 906 (R) 907 ),

[0035] Halogen atom, cyano group, nitro group,

[0036] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0037] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0038] When there are two or more substituents R, the two or more substituents R can be the same or different.

[0039] L 1A Each independently

[0040] single bond,

[0041] Substituted or unsubstituted arylene groups with 6 to 50 cyclic carbon atoms, or

[0042] A divalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0043] Ar 1A Each independently

[0044] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0045] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0046] R 901 ~R 907 Each independently

[0047] hydrogen atom,

[0048] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0049] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0050] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0051] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0052] R 901 ~R 907 When there are more than two, more than two R 901 ~R 907 They can be the same or different.

[0053] -L 1A -Ar 1A (1A)

[0054] (In formula (1A),

[0055] L 1Aand Ar 1A As defined in equation (1) above.

[0056] When there are two or more groups represented by the aforementioned formula (1A), each of the two or more groups represented by the aforementioned formula (1A) may be the same or different.

[0057] [Chemistry 2]

[0058]

[0059] (In formula (2),)

[0060] R 1B ~R 8B Each independently

[0061] hydrogen atom,

[0062] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0063] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[0064] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

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

[0066] -Si(R 901 (R) 902 (R) 903 ),

[0067] -O-(R 904 ),

[0068] -S-(R 905 ),

[0069] -N(R 906 (R) 907 ),

[0070] Halogen atom, cyano group, nitro group,

[0071] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0072] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0073] X 11B It consists of oxygen or sulfur atoms.

[0074] R 11B ~R 18B One of them is related to L 2B Bonded single bonds.

[0075] Not with L 2B bonded single bond R 11B ~R 18B Two or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings, or do not form substituted or unsubstituted saturated or unsaturated rings.

[0076] Not with L 2B R consists of bonded single bonds and does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 11B ~R 18B Each independently

[0077] hydrogen atom,

[0078] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0079] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[0080] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[0081] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0082] -Si(R 901 (R) 902 (R) 903 ),

[0083] -O-(R 904 ),

[0084] -S-(R 905 ),

[0085] -N(R 906 (R) 907 ),

[0086] Halogen atom, cyano group, nitro group,

[0087] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0088] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0089] L 1B and L 2B Each independently

[0090] single bond,

[0091] Substituted or unsubstituted arylene groups with 6 to 30 cyclic carbon atoms, or

[0092] A divalent heterocyclic group with 5 to 30 cyclic atoms, substituted or unsubstituted.

[0093] Ar 1B for

[0094] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0095] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0096] R 901 ~R 907 As defined in equation (1) above.

[0097] 2. A composition comprising a compound represented by formula (1) and a compound represented by formula (2), wherein one or more of the compounds represented by formula (1) and formula (2) contain at least one deuterium atom.

[0098] [Chemistry 3]

[0099]

[0100] In formula (1),

[0101] R 1A ~R 8A Each independently

[0102] hydrogen atom,

[0103] Substituent R, or

[0104] The group represented by the following formula (1A).

[0105] The aforementioned substituent R is

[0106] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0107] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[0108] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[0109] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0110] -Si(R 901 (R) 902 (R) 903 ),

[0111] -O-(R 904 ),

[0112] -S-(R 905 ),

[0113] -N(R 906 (R)907 ),

[0114] Halogen atom, cyano group, nitro group,

[0115] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0116] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0117] When there are two or more substituents R, the two or more substituents R can be the same or different.

[0118] L 1A Each independently

[0119] single bond,

[0120] Substituted or unsubstituted arylene groups with 6 to 50 cyclic carbon atoms, or

[0121] A divalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0122] Ar 1A Each independently

[0123] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0124] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0125] R 901 ~R 907 Each independently

[0126] hydrogen atom,

[0127] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0128] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0129] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0130] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0131] R 901 ~R 907 When there are more than two, more than two R 901 ~R 907 They can be the same or different.

[0132] -L 1A -Ar 1A (1A)

[0133] (In formula (1A),

[0134] L 1A and Ar 1A As defined in equation (1) above.

[0135] When there are two or more groups represented by the aforementioned formula (1A), each of the two or more groups represented by the aforementioned formula (1A) may be the same or different.

[0136] [Chemistry 4]

[0137]

[0138] (In formula (2),)

[0139] R 1B ~R 8B Each independently

[0140] hydrogen atom,

[0141] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0142] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[0143] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[0144] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0145] -Si(R 901 (R) 902 (R) 903 ),

[0146] -O-(R 904 ),

[0147] -S-(R 905 ),

[0148] -N(R 906 (R) 907 ),

[0149] Halogen atom, cyano group, nitro group,

[0150] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0151] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0152] X 11B It consists of oxygen or sulfur atoms.

[0153] R 11B ~R18B One of them is related to L 2B Bonded single bonds.

[0154] Not with L 2B bonded single bond R 11B ~R 18B Two or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings, or do not form substituted or unsubstituted saturated or unsaturated rings.

[0155] Not with L 2B R consists of bonded single bonds and does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 11B ~R 18B Each independently

[0156] hydrogen atom,

[0157] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0158] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[0159] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[0160] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0161] -Si(R 901 (R) 902 (R) 903 ),

[0162] -O-(R 904 ),

[0163] -S-(R 905 ),

[0164] -N(R 906 (R) 907 ),

[0165] Halogen atom, cyano group, nitro group,

[0166] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0167] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0168] L 1B and L 2B Each independently

[0169] single bond,

[0170] Substituted or unsubstituted arylene groups with 6 to 30 cyclic carbon atoms, or

[0171] A divalent heterocyclic group with 5 to 30 cyclic atoms, substituted or unsubstituted.

[0172] Ar 1B for

[0173] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0174] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0175] R 901 ~R 907 As defined in equation (1) above.

[0176] 3. Organic electroluminescent elements, which have a cathode,

[0177] anode, and

[0178] At least one light-emitting layer disposed between the aforementioned cathode and the aforementioned anode,

[0179] The aforementioned light-emitting layer comprises the composition described in section 2 above.

[0180] 4. An electronic device comprising the organic electroluminescent element described in 1 or 3 above.

[0181] According to the present invention, organic EL devices with low driving voltage, high external quantum efficiency, and long device lifetime can be provided. Attached Figure Description

[0182] [ Figure 1 This diagram illustrates a schematic configuration of an organic EL element according to one aspect of the present invention. Detailed Implementation

[0183] [definition]

[0184] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely, protium, deuterium, and tritium.

[0185] In this specification, in the chemical structural formula, hydrogen atoms, i.e. protium atoms, deuterium atoms, or tritium atoms, are bonded at positions not explicitly indicated by symbols such as "R" or "D" representing deuterium atoms.

[0186] In this specification, the number of cyclic carbon atoms refers to the number of carbon atoms in the atoms constituting the ring itself in a compound whose atoms are bonded into a cyclic structure (e.g., monocyclic compounds, fused-ring compounds, cross-linked 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 cyclic carbon atoms. The term "number of cyclic carbon atoms" as used below is the same unless otherwise specified. For example, the number of cyclic carbon atoms in a benzene ring is 6, in a naphthalene ring it is 10, in a pyridine ring it is 5, and in a furan ring it is 4. Additionally, for example, the number of cyclic carbon atoms in 9,9-diphenylfluorenyl is 13, and in 9,9'-spirodifluorenyl it is 25.

[0187] Furthermore, when a benzene ring is substituent for, for example, an alkyl group, the number of carbon atoms in that 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 ring-forming process of a benzene ring with a substituent alkyl group is 6. Similarly, when a naphthalene ring is substituent for, for example, an alkyl group, the number of carbon atoms in that 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 ring-forming process of a naphthalene ring with a substituent alkyl group is 10.

[0188] 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, cross-linked compounds, carbocyclic compounds, and heterocyclic compounds) whose atoms are bonded into a cyclic structure (e.g., monocyclic, fused-ring, and ring aggregates). Atoms that do not constitute a ring (e.g., hydrogen atoms that end the bonds of the atoms constituting the ring) 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 specified. 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 the number of atoms constituting substituents are not included in the number of atoms forming the pyridine ring. Therefore, the number of cyclic atoms in a pyridine ring bonded with hydrogen atoms or substituents is 6. Furthermore, for example, 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 bonded with hydrogen atoms or substituents is 10.

[0189] In this specification, the phrase "ZZ group with substituted or unsubstituted carbon atoms numbering XX to YY" refers to the number of carbon atoms when the ZZ group is unsubstituted, excluding the number of carbon atoms in the substituents. Here, "YY" is greater than "XX", where "XX" represents an integer greater than 1 and "YY" represents an integer greater than 2.

[0190] 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 substituted. Here, "YY" is greater than "XX", where "XX" represents an integer greater than 1 and "YY" represents an integer greater than 2.

[0191] In this specification, "unsubstituted ZZ group" means "unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".

[0192] In this specification, "unsubstituted or unsubstituted ZZ group" means that the hydrogen atom of the ZZ group is not replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0193] Furthermore, in this specification, "substitution" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms of the ZZ group are replaced by a substituent. Similarly, "substitution" in the case of "BB group substituted by AA group" also means that one or more hydrogen atoms of the BB group are replaced by an AA group.

[0194] Substituents described in this specification

[0195] The substituents described in this specification will be explained below.

[0196] Unless otherwise specified in this specification, the number of cyclic carbon atoms in the "unsubstituted aryl group" as described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0197] Unless otherwise specified in this specification, the number of cyclic atoms in the "unsubstituted heterocyclic group" specified in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0198] Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkyl" as described in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0199] Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkenyl group" described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0200] Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkynyl group" described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0201] Unless otherwise specified in this specification, the number of cyclic carbon atoms in the "unsubstituted cycloalkyl" as described in this specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6.

[0202] Unless otherwise specified in this specification, the number of cyclic carbon atoms in the "unsubstituted aryl group" described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0203] Unless otherwise specified in this specification, the number of cyclic atoms in the "unsubstituted divalent heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0204] Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkylene" as described in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0205] • "Substituted or unsubstituted aryl groups"

[0206] 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. (In this document, 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 "aryl" is mentioned alone, it includes both "unsubstituted aryl" and "substituted aryl".

[0207] "Substituted aryl" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl" group are replaced by substituents. Examples of "substituted aryl" include, for instance, the group in Specific Example Group G1A below where one or more hydrogen atoms of an "unsubstituted aryl" group are replaced by substituents, and the substituted aryl group in Specific Example Group G1B below. Furthermore, the examples of "unsubstituted aryl" and "substituted aryl" listed here are merely examples; the "substituted aryl" as described in this specification also includes groups in Specific Example Group G1B below where the hydrogen atoms bonded to the carbon atoms of the aryl group itself are further replaced by substituents, and groups in Specific Example Group G1B below where the hydrogen atoms of the substituents are further replaced by substituents.

[0208] • Unsubstituted aryl groups (specific example group G1A):

[0209] phenyl,

[0210] p-phenyl,

[0211] metaphenyl,

[0212] o-phenyl,

[0213] p-terphenyl-4-yl,

[0214] p-terphenyl-3-yl,

[0215] p-terphenyl-2-yl,

[0216] m-terphenyl-4-yl,

[0217] m-terphenyl-3-yl,

[0218] m-terphenyl-2-yl,

[0219] o-terphenyl-4-yl

[0220] o-terphenyl-3-yl

[0221] o-terphenyl-2-yl,

[0222] 1-Naphthyl,

[0223] 2-Naphthyl,

[0224] anthracene,

[0225] Benzanthracene,

[0226] Fiki,

[0227] Benzphenanthrene,

[0228] Finadenyl,

[0229] Pyrene

[0230] base,

[0231] benzo[a] base,

[0232] Tri-phenylene,

[0233] Benzotrimethylene

[0234] phenylene,

[0235] Pentaphenyl,

[0236] Fluorine

[0237] 9,9'-spirodifluorene,

[0238] benzo[f]fluorenyl,

[0239] Dibenzofluorene,

[0240] Fluoranthene group,

[0241] Benzofluoranthyl,

[0242] Perylene, and

[0243] A monovalent aryl group derived by removing one hydrogen atom from the ring structure shown by the following general formulas (TEMP-1) to (TEMP-15).

[0244] [Chemistry 5]

[0245]

[0246] [Chemistry 6]

[0247]

[0248] • Substituted aryl groups (specific example group G1B):

[0249] o-Tolyl,

[0250] m-Tolyl,

[0251] p-Tolyl,

[0252] p-Xylyl,

[0253] m-Xylyl,

[0254] o-xylyl,

[0255] p-isopropylphenyl,

[0256] m-Isopropylphenyl,

[0257] o-isopropylphenyl,

[0258] p-tert-butylphenyl,

[0259] m-tert-butylphenyl,

[0260] o-tert-butylphenyl,

[0261] 3,4,5-Trimethylphenyl

[0262] 9,9-Dimethylfluorenyl,

[0263] 9,9-Diphenylfluorenyl

[0264] 9,9-Bis(4-methylphenyl)fluorenyl,

[0265] 9,9-Bis(4-isopropylphenyl)fluorenyl,

[0266] 9,9-Bis(4-tert-butylphenyl)fluorenyl,

[0267] cyanophenyl,

[0268] Triphenylsilylphenyl

[0269] Trimethylsilylphenyl

[0270] Phenylacetyl,

[0271] Naphthylphenyl, and

[0272] The aforementioned groups derived from the ring structures shown in general formulas (TEMP-1) to (TEMP-15) are groups in which one or more hydrogen atoms of a monovalent group are replaced by substituents.

[0273] • "Substituted or unsubstituted heterocyclic groups"

[0274] The term "heterocyclic group" as used in this specification refers to a cyclic group containing at least one heteroatom in its cyclic atom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.

[0275] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.

[0276] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0277] 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. (In this document, an unsubstituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and a substituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when "heterocyclic group" is mentioned alone, it includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".

[0278] "Substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by substituents. Specific examples of "substituted heterocyclic groups" include the group in Example Group G2A below where the hydrogen atoms of the "unsubstituted heterocyclic group" are replaced, and the examples of substituted heterocyclic groups in Example Group G2B below. Furthermore, 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 groups in Example Group G2B where the hydrogen atoms bonded to the cyclic atoms of the heterocyclic group itself are further replaced by substituents, and groups in Example Group G2B where the hydrogen atoms of the substituents are further replaced by substituents.

[0279] 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 by removing one hydrogen atom from the ring structure shown by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0280] Specific example group G2B includes, for example, the following: a substituted heterocyclic group containing a nitrogen atom (specific example group G2B1), a substituted heterocyclic group containing an oxygen atom (specific example group G2B2), a substituted heterocyclic group containing a sulfur atom (specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific example group G2B4).

[0281] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1):

[0282] pyrrole,

[0283] Imidazole group,

[0284] Pyrazolyl,

[0285] Triazole group,

[0286] Tetraazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridinyl, pyridinyl, pyrazinyl, triazinyl, indoleyl, isindoleyl, indoleazinyl, quinazinyl, quinolinyl, isoquinolinyl, cinolinyl, phthalazinyl, quinazolinyl, quinoxolinyl, benzimidazolyl, indoleyl, phenanthrolinel, phenanthridyl, acridineyl, phenazinyl, carbazoleyl, benzocarbazoleyl, morpholinoyl, phenoxazinyl

[0287] phenothiazine group,

[0288] Azacarbazolyl and

[0289] Diazacarbazolyl.

[0290] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2): furanyl,

[0291] Oxazolyl,

[0292] Isoxazolyl,

[0293] Oxadiazole group,

[0294] Xuton base,

[0295] Benzofuranyl,

[0296] Isobenzofuranyl,

[0297] Dibenzofuranyl,

[0298] Naphthobenzofuranyl,

[0299] Benzoxazolyl,

[0300] Benzisoxazole group,

[0301] phenoxazine group,

[0302] Morpholinyl group

[0303] Dinaphthylfuranyl,

[0304] Azadibenzofuranyl,

[0305] diazadibenzofuranyl,

[0306] Azanaphthalenebenzofuranyl, and

[0307] Diazanaphthenebenzofuranyl.

[0308] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3): thiophene group,

[0309] Thiazole group,

[0310] Isothiazolyl,

[0311] Thiadiazole group,

[0312] benzothienyl group

[0313] isobenzothienyl group

[0314] dibenzothienyl group

[0315] Naphthobenzothienyl group

[0316] Benzothiazolyl,

[0317] Benzisothiazolyl,

[0318] phenothiazine group,

[0319] dinaphthothienyl group

[0320] azadibenzothienyl group

[0321] diazadibenzothienyl group

[0322] azanaphthobenzothienyl group, and

[0323] diazanaphthobenzothienyl group.

[0324] • Monovalent heterocyclic groups 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):

[0325] [Chemistry 7]

[0326]

[0327] [Chemistry 8]

[0328]

[0329] In the aforementioned general formulas (TEMP-16) to (TEMP-33), X A and Y A Each can be independently 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.

[0330] In the aforementioned 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 groups.

[0331] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1):

[0332] (9-phenyl)carbazole group,

[0333] (9-Biphenyl)carbazole,

[0334] (9-Phenyl)phenylcarbazolyl,

[0335] (9-Naphthyl)carbazole,

[0336] Diphenylcarbazole-9-yl,

[0337] Phenylexacarbazole-9-yl,

[0338] Methylbenzimidazole,

[0339] Ethylbenzimidazole,

[0340] Phenylacetyl,

[0341] Biphenyltriazine,

[0342] diphenyltriazine group,

[0343] phenylquinazolinyl, and

[0344] Biphenylquinazolinyl.

[0345] • Heterocyclic groups containing oxygen atoms (specific example group G2B2):

[0346] Phenyl dibenzofuranyl,

[0347] Methyldibenzofuranyl,

[0348] tert-butyldibenzofuranyl, and

[0349] The monovalent residues of [9H-xanton-9,9'-[9H]fluorene].

[0350] • Heterocyclic groups containing sulfur atoms (specific example group G2B3):

[0351] Phenyl dibenzothiophene,

[0352] Methyldibenzothiophene,

[0353] tert-butyldibenzothiophene, and

[0354] The monovalent residue of [9H-thioxanth-9,9'-[9H]fluorene].

[0355] • Groups in which one or more hydrogen atoms of the monovalent heterocyclic group derived from the ring structures shown in general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific example group G2B4):

[0356] 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.

[0357] • "Substituted or unsubstituted alkyl groups"

[0358] 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. (In this document, unsubstituted alkyl means the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl means the case where "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when "alkyl" is mentioned alone, it includes both "unsubstituted alkyl" and "substituted alkyl".

[0359] "Substituted alkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl" are replaced by substituents. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms in an "unsubstituted alkyl" (specific example group G3A) are replaced by substituents, and examples of substituted alkyl (specific example group G3B), etc. In this specification, "unsubstituted alkyl" refers to a chain-like alkyl group. Therefore, "unsubstituted alkyl" includes straight-chain "unsubstituted alkyl" and branched-chain "unsubstituted alkyl". Furthermore, 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 itself in a "substituted alkyl" of specific example group G3B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in a "substituted alkyl" of specific example group G3B are further replaced by substituents.

[0360] • Unsubstituted alkyl groups (specific example group G3A):

[0361] methyl,

[0362] Ethyl,

[0363] n-propyl,

[0364] Isopropyl,

[0365] n-Butyl,

[0366] Isobutyl,

[0367] sec-butyl, and

[0368] tert-butyl.

[0369] • Substituted alkyl groups (specific example group G3B):

[0370] Heptafluoropropyl (including isomers),

[0371] Pentafluoroethyl,

[0372] 2,2,2-Trifluoroethyl, and

[0373] Trifluoromethyl

[0374] • "Substituted or unsubstituted alkenyl groups"

[0375] Specific examples of "substituted or unsubstituted alkenyl groups" described in this specification (specific example group G4) include unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (In this document, "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 "alkenyl group" is mentioned alone, it includes both "unsubstituted alkenyl group" and "substituted alkenyl group".

[0376] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" are replaced by substituents. Specific examples of "substituted alkenyl" include the substituents in the "unsubstituted alkenyl" group (specific example group G4A) and examples of substituted alkenyl groups (specific example group G4B). Furthermore, 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 group itself are further replaced by substituents, and groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the substituents are further replaced by substituents.

[0377] • Unsubstituted alkenyl groups (specific example group G4A):

[0378] vinyl,

[0379] Allyl

[0380] 1-Butenyl,

[0381] 2-Butenyl, and

[0382] 3-Butenyl.

[0383] • Substituted alkenyl groups (specific example group G4B):

[0384] 1,3-Butadienyl,

[0385] 1-Methylvinyl

[0386] 1-Methylallyl,

[0387] 1,1-Dimethylallyl,

[0388] 2-Methylallyl, and

[0389] 1,2-Dimethylallyl.

[0390] • "Substituted or unsubstituted alkynyl groups"

[0391] 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) are examples. (In this text, unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group".) Hereinafter, when "alkynyl group" is mentioned alone, it includes both "unsubstituted alkynyl group" and "substituted alkynyl group".

[0392] "Substituted alkynyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl" are replaced by a substituent. Specific examples of "substituted alkynyl" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl" (specific example group G5A) are replaced by a substituent.

[0393] • Unsubstituted alkynyl group (specific example group G5A):

[0394] Acetylene group.

[0395] • "Substituted or unsubstituted cycloalkyl groups"

[0396] 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. (In this document, 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 "cycloalkyl" is mentioned alone, it includes both "unsubstituted cycloalkyl" and "substituted cycloalkyl".

[0397] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group are replaced by substituents. Specific examples of "substituted cycloalkyl" include groups in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group (specific example group G6A) are replaced by substituents, and examples of substituted cycloalkyl groups (specific example group G6B). Furthermore, the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples; the "substituted cycloalkyl" as 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 are replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted cycloalkyl" group of specific example group G6B are further replaced by substituents.

[0398] • Unsubstituted cycloalkyl groups (specific example group G6A):

[0399] Cyclopropyl

[0400] Cyclobutyl,

[0401] Cyclopentyl,

[0402] Cyclohexyl,

[0403] 1-Adamantyl,

[0404] 2-Adamantyl,

[0405] 1-Norbornel alkyl, and

[0406] 2-Norbornel alkyl.

[0407] • Substituted cycloalkyl groups (specific example group G6B):

[0408] 4-Methylcyclohexyl.

[0409] ·"-Si(R 901 (R) 902 (R) 903 The group shown in the figure”

[0410] As described in this specification, -Si(R) 901 (R) 902 (R) 903 Specific examples of the groups shown (specific example group G7) can be listed.

[0411] -Si(G1)(G1)(G1),

[0412] -Si(G1)(G2)(G2),

[0413] -Si(G1)(G1)(G2),

[0414] -Si(G2)(G2)(G2),

[0415] -Si(G3)(G3)(G3), and

[0416] -Si(G6)(G6)(G6). Here.

[0417] G1 refers to the "substituted or unsubstituted aryl group" described in specific example group G1.

[0418] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0419] G3 refers to the "substituted or unsubstituted alkyl group" as described in specific example group G3.

[0420] G6 refers to the "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0421] In -Si(G1)(G1)(G1), multiple G1s can be the same or different from each other.

[0422] In -Si(G1)(G2)(G2), multiple G2s can be the same or different from each other.

[0423] In -Si(G1)(G1)(G2), multiple G1s can be the same or different from each other.

[0424] In -Si(G2)(G2)(G2), multiple G2s can be the same or different from each other.

[0425] In -Si(G3)(G3)(G3), multiple G3s can be the same or different from each other.

[0426] In -Si(G6)(G6)(G6), multiple G6s can be the same or different from each other.

[0427] ·“-O-(R 904 The group shown in the figure”

[0428] As described in this specification, -O-(R) 904 Specific examples of the groups shown (specific example group G8) can be listed.

[0429] -O(G1)

[0430] -O(G2),

[0431] -O(G3), and

[0432] -O(G6).

[0433] Here,

[0434] G1 refers to the "substituted or unsubstituted aryl group" described in specific example group G1.

[0435] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0436] G3 refers to the "substituted or unsubstituted alkyl group" as described in specific example group G3.

[0437] G6 refers to the "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0438] ·“-S-(R 905 The group shown in the figure”

[0439] As described in this specification, -S-(R) 905 Specific examples of the groups shown (specific example group G9) can be listed.

[0440] -S(G1)

[0441] -S(G2),

[0442] -S(G3), and

[0443] -S(G6).

[0444] Here,

[0445] G1 refers to the "substituted or unsubstituted aryl group" described in specific example group G1.

[0446] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0447] G3 refers to the "substituted or unsubstituted alkyl group" as described in specific example group G3.

[0448] G6 refers to the "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0449] ·"-N(R 906 (R) 907 The group shown in the figure”

[0450] As described in this specification, -N(R) 906 (R) 907 Specific examples of the groups shown (specific example group G10) can be listed.

[0451] -N(G1)(G1),

[0452] -N(G2)(G2),

[0453] -N(G1)(G2),

[0454] -N(G3)(G3), and

[0455] -N(G6)(G6).

[0456] Here,

[0457] G1 refers to the "substituted or unsubstituted aryl group" described in specific example group G1.

[0458] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0459] G3 refers to the "substituted or unsubstituted alkyl group" as described in specific example group G3.

[0460] G6 refers to the "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0461] In -N(G1)(G1), multiple G1s can be the same or different from each other.

[0462] In -N(G2)(G2), multiple G2s can be the same or different from each other.

[0463] In -N(G3)(G3), multiple G3s can be the same or different from each other.

[0464] The multiple G6 values ​​in -N(G6)(G6) can be the same or different from each other.

[0465] • "Halogen atom"

[0466] Specific examples of "halogen atoms" as described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0467] • "Substituted or unsubstituted fluoroalkyl groups"

[0468] 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 is replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group are 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 are replaced by a substituent. Furthermore, 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 are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl" group are further replaced by substituents. Specific examples of "unsubstituted fluoroalkyl" include groups in which one or more hydrogen atoms of the aforementioned "alkyl" group (specific example group G3) are replaced by fluorine atoms.

[0469] • "Substituted or unsubstituted haloalkyl groups"

[0470] 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 is replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group are 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 are replaced by a substituent. Furthermore, the term "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 are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent in a "substituted haloalkyl" group are further replaced by substituents. Specific examples of "unsubstituted haloalkyl" include groups in which one or more hydrogen atoms of the aforementioned "alkyl" group (specific example group G3) are replaced by halogen atoms. Sometimes alkyl halides are referred to as alkyl halides.

[0471] • "Substituted or unsubstituted alkoxy groups"

[0472] As a specific example of the "substituted or unsubstituted alkoxy group" described in this specification, it is the group represented by -O (G3), where G3 refers to the "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise stated in this specification, the "unsubstituted alkoxy group" has 1 to 50 carbon atoms, preferably 1 to 30, and more preferably 1 to 18.

[0473] • "Substituted or unsubstituted alkylthio groups"

[0474] As a specific example of the "substituted or unsubstituted alkylthio group" described in this specification, it is the group indicated by -S(G3), where G3 refers to the "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise stated in this specification, the "unsubstituted alkylthio group" has 1 to 50 carbon atoms, preferably 1 to 30, and more preferably 1 to 18.

[0475] • "Substituted or unsubstituted aryloxy groups"

[0476] As a specific example of the "substituted or unsubstituted aryloxy group" described in this specification, it is the group represented by -O (G1), where G1 refers to the "substituted or unsubstituted aryl group" described in specific example group G1. Unless otherwise stated in this specification, the number of cyclic carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0477] • "Substituted or unsubstituted arylthio groups"

[0478] As a specific example of the "substituted or unsubstituted aryl thio group" described in this specification, it is the group indicated by -S(G1), where G1 refers to the "substituted or unsubstituted aryl group" described in specific example group G1. Unless otherwise stated in this specification, the number of cyclic carbon atoms of the "unsubstituted aryl thio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0479] • "Substituted or unsubstituted trialkylsilyl groups"

[0480] 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" as described in the specific example group G3. The plurality of G3s in -Si(G3)(G3)(G3) may be the same or different from each other. Unless otherwise stated 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.

[0481] • "Substituted or unsubstituted aralkyl groups"

[0482] As a specific example of the "substituted or unsubstituted aralkyl" 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" replaced by "unsubstituted aryl", and unless otherwise specified in this specification, the number of carbon atoms in "unsubstituted aralkyl" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18.

[0483] 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.

[0484] Unless otherwise specified in this specification, the substituted or unsubstituted aryl groups described herein are preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthraceneyl, phenanthryl, pyreneyl, etc. It includes compounds such as methyl, triphenyl, fluorenyl, 9,9'-spirodifluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl.

[0485] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic groups described herein are preferably pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, phenanthrolinel, carbazoleyl (1-carbazoleyl, 2-carbazoleyl, 3-carbazoleyl, 4-carbazoleyl, or 9-carbazoleyl), benzocarbazoleyl, azacarbazoleyl, diazacarbazoleyl, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiopheneyl, naphtho 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.

[0486] In this specification, unless otherwise stated herein, the carbazoyl group specifically refers to any of the following groups.

[0487] [Chemistry 9]

[0488]

[0489] In this specification, unless otherwise stated herein, (9-phenyl)carbazolyl specifically refers to any of the following groups.

[0490] [Chemistry 10]

[0491]

[0492] In the aforementioned general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.

[0493] In this specification, unless otherwise stated herein, dibenzofuranyl and dibenzothiopheneyl specifically refer to any of the following groups.

[0494] [Chemistry 11]

[0495]

[0496] In the aforementioned general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.

[0497] 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, etc.

[0498] • "Substituted or unsubstituted aryl groups"

[0499] Unless otherwise stated, the "substituted or unsubstituted aryl group" described in this specification is a divalent group derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described above. Specific examples of the "substituted or unsubstituted aryl group" (specific example group G12) include divalent groups derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described in specific example group G1.

[0500] • "Substituted or unsubstituted divalent heterocyclic group"

[0501] Unless otherwise stated, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom from the heterocyclic group described above. Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include divalent groups derived by removing one hydrogen atom from the heterocyclic group described in specific example group G2.

[0502] • "Substituted or unsubstituted alkylene compounds"

[0503] Unless otherwise stated, the "substituted or unsubstituted alkylene group" as described in this specification is a divalent group derived by removing one hydrogen atom from the alkyl chain of the aforementioned "substituted or unsubstituted alkylene group". Specific examples of "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkylene group" described in specific example group G3.

[0504] Unless otherwise stated in this specification, the substituted or unsubstituted aryl group described herein is preferably any group of the following general formulas (TEMP-42) to (TEMP-68).

[0505] [Chemistry 12]

[0506]

[0507] [Chemistry 13]

[0508]

[0509] In the aforementioned general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0510] In the aforementioned general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.

[0511] [Chemistry 14]

[0512]

[0513] In the aforementioned general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0514] Formulas Q9 and Q 10 They can bond together to form rings through single bonds.

[0515] In the aforementioned general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.

[0516] [Chemistry 15]

[0517]

[0518] In the aforementioned general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0519] In the aforementioned general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.

[0520] Unless otherwise stated 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).

[0521] [Chemistry 16]

[0522]

[0523] [Chemistry 17]

[0524]

[0525] [Chemistry 18]

[0526]

[0527] In the aforementioned general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0528] [Chemistry 19]

[0529]

[0530] [Chemistry 20]

[0531]

[0532] [Chemistry 21]

[0533]

[0534] [Chemistry 22]

[0535]

[0536] In the aforementioned general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0537] The above is a description of the substituents described in this specification.

[0538] • "Cases where bonds form rings"

[0539] In this specification, the phrase "forming a substituted or unsubstituted monocyclic ring by bonding one or more groups of two or more adjacent elements together, forming a substituted or unsubstituted fused ring, or not bonding with each other" refers to the following situations: "forming a substituted or unsubstituted monocyclic ring by bonding one or more groups of two or more adjacent elements together, forming a substituted or unsubstituted fused ring by bonding one or more groups of two or more adjacent elements together, forming a substituted or unsubstituted fused ring"; and "not bonding with each other" in the case of "forming a substituted or unsubstituted monocyclic ring by bonding one or more groups of two or more adjacent elements together".

[0540] The following explanation addresses the cases described in this specification as "forming a substituted or unsubstituted monocyclic ring by bonding one or more groups of two or more adjacent elements together" and "forming a substituted or unsubstituted fused ring by bonding one or more groups of two or more adjacent elements together" (hereinafter sometimes collectively referred to as "forming a ring by bonding"). An example is an anthracene compound represented by the following general formula (TEMP-103) with an anthracene ring as its parent skeleton.

[0541] [Chemistry 23]

[0542]

[0543] For example, R 921 ~R 930 In the case of "one or more groups consisting of two or more adjacent elements bonded together to form a loop", the group consisting of two adjacent elements that forms a single group is R. 921 With R 922 group, R 922 With R 923 group, R 923 With R 924 group, R 924 With R 930 group, R 930 With R 925 group, R 925With 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.

[0544] The phrase "one or more groups" refers to the fact that two or more groups consisting of two or more adjacent elements can simultaneously form a loop. For example, R 921 With R 922 They bond together to form a ring Q A Meanwhile, R 925 With R 926 They bond together to form a ring Q B In this case, the anthracene compound represented by the aforementioned general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0545] [Chemistry 24]

[0546]

[0547] The formation of rings from "groups consisting of two or more adjacent elements" includes not only the bonded group of "two" adjacent elements as in the previous example, but also the bonded group 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 anthracene bonds together to form a ring, and the anthracene parent skeleton is fused, the anthracene compound represented by the aforementioned 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 .

[0548] [Chemistry 25]

[0549]

[0550] The formed "single ring" or "fused ring" is only a structural feature of the formed ring and can be either a saturated or unsaturated ring. Even when forming a "single ring" or "fused ring," the "single ring" or "fused ring" can still form either a saturated or unsaturated ring. For example, the ring Q formed in the aforementioned general formula (TEMP-104) A and ring Q B These are respectively "monocyclic" or "fused-ring". Furthermore, the ring Q formed in the aforementioned general formula (TEMP-105) A and ring Q C It is a "fused ring". The ring Q of the aforementioned general formula (TEMP-105) A With ring Q C Through ring Q A With ring Q C They fuse to form fused rings. If the ring Q of the aforementioned 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 aforementioned general formula (TMEP-104) is... A If it is a naphthalene ring, then ring Q A It is a fused ring.

[0551] "Unsaturated rings" refer to aromatic hydrocarbon rings or aromatic heterocycles. "Saturated rings" refer to aliphatic hydrocarbon rings or non-aromatic heterocycles.

[0552] As a specific example of an aromatic hydrocarbon ring, the structure in specific example group G1, where the group is end-capped with a hydrogen atom, can be cited.

[0553] As a specific example of an aromatic heterocycle, the structure in example group G2 where the aromatic heterocycle group is end-capped with hydrogen atoms can be cited.

[0554] As a specific example of an aliphatic hydrocarbon ring, the structure in example group G6, where the group is end-capped with a hydrogen atom, can be cited.

[0555] "Ring formation" refers to the formation of a ring by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton further forming a ring with one or more arbitrary elements. For example, R shown in the aforementioned 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 bonded anthracene skeleton consists of a ring formed by carbon atoms and one or more elements. As a specific example, R... 921 With R 922 Forming ring Q A In the case of R 921 The carbon atoms and R atoms of the bonded anthracene skeleton922 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.

[0556] Unless otherwise stated in this specification, "any element" is preferably selected from at least one element chosen from carbon, nitrogen, oxygen, and sulfur. In the case of any element (e.g., carbon or nitrogen), non-ring bonds can be capped by hydrogen atoms or substituted by "any substituents" described later. When any element other than carbon is included, the resulting ring is a heterocycle.

[0557] Unless otherwise specified in this specification, the number of "1 or more arbitrary elements" constituting a monocyclic or fused ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.

[0558] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".

[0559] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".

[0560] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.

[0561] Unless otherwise stated in this specification, the "unsaturated ring" is preferably a benzene ring.

[0562] "One or more groups consisting of two or more adjacent elements" refers to either "mutually bonded to form a substituted or unsubstituted monocyclic ring" or "mutually bonded to form a substituted or unsubstituted fused ring." Unless otherwise stated in this specification, it is preferred that one or more groups consisting of two or more adjacent elements are mutually bonded to form an "unsaturated ring" containing a parent skeleton and at least one to 15 substituted or unsubstituted elements selected from carbon, nitrogen, oxygen, and sulfur.

[0563] When a "monocyclic" or "fused-ring" structure has a substituent, the substituent is, for example, "any substituent" as described below. Specific examples of substituents when a "monocyclic" or "fused-ring" structure has a substituent are the substituents described in the "Substituents Described in this Specification" section above.

[0564] When the aforementioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, "any substituent" as described later. Specific examples of substituents when the aforementioned "monocyclic" or "fused ring" has a substituent are the substituents described in the "Substituents Described in this Specification" section above.

[0565] The above explains the cases of "a single ring formed by bonding one or more groups of two or more adjacent elements together, with substitution or no substitution", and the cases of "a fused ring formed by bonding one or more groups of two or more adjacent elements together, with substitution or no substitution" ("the case of forming a ring by bonding").

[0566] Substituents referred to as "substituted or unsubstituted"

[0567] In one embodiment of this specification, the substituents referred to as "substituted or unsubstituted" (in this specification, sometimes referred to as "arbitrary substituents") are selected from, for example...

[0568] Unsubstituted alkyl groups with 1 to 50 carbon atoms

[0569] Unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0570] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms

[0571] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0572] -Si(R 901 (R) 902 (R) 903 ),

[0573] -O-(R 904 ),

[0574] -S-(R 905 ),

[0575] -N(R 906 (R) 907 ),

[0576] Halogen atom, cyano group, nitro group,

[0577] Unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, and

[0578] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, etc.

[0579] Here, R 901 ~R 907 Each independently

[0580] hydrogen atom,

[0581] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0582] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0583] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0584] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0585] R 901 When there are more than two, more than two R 901 They are the same or different.

[0586] R 902 When there are more than two, more than two R 902 They are the same or different.

[0587] R 903 When there are more than two, more than two R 903 They are the same or different.

[0588] R 904 When there are more than two, more than two R 904 They are the same or different.

[0589] R 905 When there are more than two, more than two R 905 They are the same or different.

[0590] R 906 When there are more than two, more than two R 906 They are the same or different.

[0591] R 907 When there are more than two, more than two R 907 They are the same or different from each other.

[0592] In one embodiment, the substituent referred to as "substituted or unsubstituted" is an alkyl group selected from those having 1 to 50 carbon atoms.

[0593] aryl groups with 6 to 50 carbon atoms in the ring, and

[0594] Groups in heterocyclic groups with 5 to 50 cyclic atoms.

[0595] In one embodiment, the substituent referred to as "substituted or unsubstituted" is an alkyl group selected from those having 1 to 18 carbon atoms.

[0596] aryl groups with 6 to 18 carbon atoms in the ring, and

[0597] Groups in heterocyclic groups with 5 to 18 cyclic atoms.

[0598] Specific examples of each group of any of the above-mentioned substituents are the specific examples of substituents described in the section "Substituents as Described in this Specification" above.

[0599] Unless otherwise specified in this specification, any adjacent substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring.

[0600] Unless otherwise specified in this specification, any substituent may further have substituents. Substituents further having by any substituent are the same as those described above.

[0601] In this specification, the numerical range represented by "AA~BB" refers to the range included by taking the value AA before "AA~BB" as the lower limit and the value BB after "AA~BB" as the upper limit.

[0602] [Organic EL Components]

[0603] One aspect of the present invention is an organic EL element having a cathode, an anode, and a light-emitting layer disposed between the cathode and the anode, characterized in that the light-emitting layer comprises a first host material, a second host material, and a dopant material.

[0604] The first main material is the compound represented by formula (1) described later.

[0605] The second main material is the compound shown in formula (2) described later.

[0606] One or more of the compounds shown in formula (1) and formula (2) have at least one deuterium atom.

[0607] It should be noted that the first main material and the second main material are different materials.

[0608] An organic EL device according to one aspect of the present invention exhibits high device performance by having the above-described configuration. Specifically, an organic EL device with low drive voltage, high external quantum efficiency, and long device lifetime can be provided.

[0609] Details regarding each material are provided below.

[0610] Reference Figure 1 This invention describes the general configuration of an organic EL element according to one aspect of the present invention.

[0611] An organic EL element 1 according to one aspect of the present invention has a substrate 2, an anode 3, a light-emitting layer 5, a cathode 10, an organic layer 4 between the anode 3 and the light-emitting layer 5, and an organic layer 6 between the light-emitting layer 5 and the cathode 10.

[0612] The first host material, the second host material, and the dopant material are contained in the light-emitting layer 5 between the anode 3 and the cathode 10. Each compound contained in the light-emitting layer 5 may be a single type or two or more types.

[0613] It should be noted that the organic EL element 1 may also include a light-emitting layer in addition to the light-emitting layer 5. In one embodiment of the present invention, a first host material, a second host material and a dopant material are typically included in a single light-emitting layer (light-emitting layer 5).

[0614] (Main Material 1)

[0615] The first main material is the compound shown in formula (1) below.

[0616] [Chemistry 26]

[0617]

[0618] In formula (1),

[0619] R 1A ~R 8A Each independently

[0620] hydrogen atom,

[0621] Substituent R, or

[0622] The group represented by the following formula (1A).

[0623] The aforementioned substituent R is

[0624] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0625] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[0626] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[0627] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0628] -Si(R 901 (R) 902 (R) 903 ),

[0629] -O-(R 904 ),

[0630] -S-(R 905 ),

[0631] -N(R 906 (R) 907 ),

[0632] Halogen atom, cyano group, nitro group,

[0633] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0634] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0635] When there are two or more substituents R, the two or more substituents R can be the same or different.

[0636] L 1A Each independently

[0637] single bond,

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

[0639] A divalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0640] Ar 1A Each independently

[0641] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0642] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0643] R 901 ~R 907 Each independently

[0644] hydrogen atom,

[0645] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0646] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0647] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0648] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0649] R 901 ~R 907 When there are more than two, more than two R 901 ~R 907 They can be the same or different.

[0650] -L1A -Ar 1A (1A)

[0651] (In formula (1A),

[0652] L 1A and Ar 1A As defined in equation (1) above.

[0653] When there are two or more groups represented by the aforementioned formula (1A), each of the two or more groups represented by the aforementioned formula (1A) may be the same or different.

[0654] In one embodiment, the compound represented by the aforementioned formula (1) is the compound represented by the following formula (1-1).

[0655] [Chemistry 27]

[0656]

[0657] (In equation (1-1), R) 1A R 3A ~R 8A L 1A and Ar 1A As defined in equation (1) above.

[0658] In one embodiment, the compound represented by formula (1) is a compound represented by formula (1-11), formula (1-12) or formula (1-13).

[0659] [Chemistry 28]

[0660]

[0661] In equations (1-11), (1-12), and (1-13), R 1A R 3A ~R 8A L 1A and Ar 1A As defined in equation (1) above.

[0662] In one embodiment, the compound represented by formula (1) is the compound represented by formula (1-2) below.

[0663] [Chemistry 29]

[0664]

[0665] (In equation (1-2), L) 1A and Ar 1A As defined in equation (1) above.

[0666] In one embodiment, the compound represented by formula (1) is a compound represented by formula (1-21), formula (1-22) or formula (1-23).

[0667] [Chemistry 30]

[0668]

[0669] In equations (1-21), (1-22), and (1-23), L 1A and Ar 1A As defined in equation (1) above.

[0670] In one implementation, L 1A It is an arylene group consisting of 6 to 14 cyclic carbon atoms, either single-bonded, substituted, or unsubstituted.

[0671] In one implementation, L 1A It is a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

[0672] In one implementation, Ar 1A It is an aryl group with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted.

[0673] In one implementation, Ar 1A Selected from the groups shown in the following formulas (a1) to (a4).

[0674] [Chemistry 31]

[0675]

[0676] (In equations (a1) to (a4), * represents the symbol with respect to L) 1A Bonded single bonds.

[0677] R 21 for

[0678] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0679] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[0680] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[0681] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0682] -Si(R 901 (R) 902 (R) 903 ),

[0683] -O-(R 904 ),

[0684] -S-(R 905 ),

[0685] -N(R 906 (R) 907 ),

[0686] Halogen atom, cyano group, nitro group,

[0687] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0688] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0689] R 901 ~R 907 As defined in equation (1) above.

[0690] m1 is an integer from 0 to 4.

[0691] m2 is an integer from 0 to 5.

[0692] m3 is an integer from 0 to 7.

[0693] When m1 to m3 are each 2 or more, multiple R 21 They can be the same or different.

[0694] When m1 to m3 are each 2 or more, multiple adjacent R 21 They bond together to form substituted or unsubstituted saturated or unsaturated rings, or they do not form substituted or unsubstituted saturated or unsaturated rings.

[0695] In one embodiment, the compound represented by the aforementioned formula (1) contains at least one deuterium atom.

[0696] In one implementation, R 1A ~R 8A At least one of them is a deuterium atom.

[0697] It should be noted that, in one embodiment, the content of the compound represented by formula (1) in the luminescent layer, and the compound having the same structure as the compound represented by formula (1) except that it contains only protium atoms as hydrogen atoms (hereinafter also referred to as "protium body"), is 99 mol% or less. The content of protium body is determined by mass spectrometry.

[0698] The compound shown in formula (1) can be synthesized by using known substitution reactions and starting materials corresponding to the target substance.

[0699] The following describes specific examples of compounds represented by formula (1). These are merely illustrative examples, and the compounds represented by formula (1) are not limited to the specific examples described below.

[0700] [Chemistry 32]

[0701]

[0702] [Chemistry 33]

[0703]

[0704] [Chemistry 34]

[0705]

[0706] [Chemistry 35]

[0707]

[0708] [Chemistry 36]

[0709]

[0710] [Chemistry 37]

[0711]

[0712] [Chemistry 38]

[0713]

[0714] [Chemistry 39]

[0715]

[0716] (Second main material)

[0717] In one embodiment of the present invention, the second main material used is a compound represented by the following formula (2).

[0718] [Chemistry 40]

[0719]

[0720] (In formula (2),)

[0721] R 1B ~R 8B Each independently

[0722] hydrogen atom,

[0723] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0724] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[0725] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[0726] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0727] -Si(R 901 (R) 902 (R) 903 ),

[0728] -O-(R 904 ),

[0729] -S-(R 905 ),

[0730] -N(R 906 (R) 907 ),

[0731] Halogen atom, cyano group, nitro group,

[0732] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0733] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0734] X 11B It consists of oxygen or sulfur atoms.

[0735] R 11B ~R 18B One of them is related to L 2B Bonded single bonds.

[0736] Not with L 2B bonded single bond R 11B ~R 18B Two or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings, or do not form substituted or unsubstituted saturated or unsaturated rings.

[0737] Not with L 2B R consists of bonded single bonds and does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 11B ~R 18B Each independently

[0738] hydrogen atom,

[0739] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0740] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[0741] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[0742] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0743] -Si(R 901 (R) 902 (R) 903 ),

[0744] -O-(R 904 ),

[0745] -S-(R 905 ),

[0746] -N(R 906 (R) 907 ),

[0747] Halogen atom, cyano group, nitro group,

[0748] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0749] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0750] L 1B and L 2B Each independently

[0751] single bond,

[0752] Substituted or unsubstituted arylene groups with 6 to 30 cyclic carbon atoms, or

[0753] A divalent heterocyclic group with 5 to 30 cyclic atoms, substituted or unsubstituted.

[0754] Ar 1B for

[0755] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0756] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0757] R 901 ~R 907 As defined in equation (1) above.

[0758] In one implementation, not with L 2B bonded single bond R 11B ~R 18B Two or more adjacent rings in a group do not form substituted or unsubstituted saturated or unsaturated rings.

[0759] In one embodiment, the compound represented by the aforementioned formula (2) is a compound represented by any one of the following formulas (2-1) to (2-3).

[0760] [Chemistry 41]

[0761]

[0762] (In equations (2-1) to (2-3),

[0763] R 1B ~R 8B L 1B L 2B Ar 1B and X 11B As defined in equation (2) above.

[0764] R 25B ~R 28B Two or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings.

[0765] R 21B ~R 24B Two or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings, or do not form substituted or unsubstituted saturated or unsaturated rings.

[0766] R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 21B ~R 28B Each independently

[0767] hydrogen atom,

[0768] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0769] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[0770] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[0771] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0772] -Si(R 901 (R) 902 (R) 903 ),

[0773] -O-(R 904 ),

[0774] -S-(R 905 ),

[0775] -N(R 906 (R) 907 ),

[0776] Halogen atom, cyano group, nitro group,

[0777] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0778] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0779] R 901 ~R 907 As defined in equation (1) above.

[0780] In one implementation, L 1B and L 2B Each is an arylene group consisting of 6 to 14 cyclic carbon atoms, either individually or with a single bond, or with or without substitution.

[0781] In one implementation, L 1B and L 2B Each is independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

[0782] In one implementation, Ar 1B It is an aryl group with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted.

[0783] In one implementation, Ar 1B Selected from the groups shown in the following formulas (a1) to (a4).

[0784] [Chemistry 42]

[0785]

[0786] (In equations (a1) to (a4), * represents the symbol with respect to L) 1B Bonded single bonds.

[0787] R 21 for

[0788] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0789] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[0790] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[0791] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0792] -Si(R 901 (R) 902 (R) 903 ),

[0793] -O-(R 904 ),

[0794] -S-(R 905 ),

[0795] -N(R 906(R) 907 ),

[0796] Halogen atom, cyano group, nitro group,

[0797] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0798] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0799] R 901 ~R 907 As defined in equation (1) above.

[0800] m1 is an integer from 0 to 4.

[0801] m2 is an integer from 0 to 5.

[0802] m3 is an integer from 0 to 7.

[0803] When m1 to m3 are each 2 or more, multiple R 21 They can be the same or different.

[0804] When m1 to m3 are each 2 or more, multiple adjacent R 21 They bond together to form substituted or unsubstituted saturated or unsaturated rings, or they do not form substituted or unsubstituted saturated or unsaturated rings.

[0805] In one implementation, X 11B It is an oxygen atom.

[0806] In one embodiment, the compound represented by formula (2) or formulas (2-1) to (2-3) is a compound represented by any one of formulas (2-11) to (2-14).

[0807] [Chemistry 43]

[0808]

[0809]

[0810] (In equations (2-11) to (2-14), Ar) 1B As defined in equation (2) above. R 25B ~R 28B As defined in equations (2-1) to (2-3) above.

[0811] In one implementation, R in the aforementioned formula (1) 1A ~R 8A And R in the aforementioned equation (2) 1B ~R 8B At least two of them are deuterium atoms.

[0812] In one implementation, R in the aforementioned formula (1) 1A ~R 8A And R in the aforementioned equation (2) 1B ~R 8B All of them are deuterium atoms.

[0813] In one embodiment, the compound represented by the aforementioned formula (2) contains at least one deuterium atom.

[0814] In one implementation, R 1B ~R 8B At least one of them is a deuterium atom.

[0815] It should be noted that, in one embodiment, the content of the compound of formula (2) in the luminescent layer and the compound having the same structure as the compound of formula (2) except that it contains only protium atoms as hydrogen atoms (hereinafter also referred to as "protium body") is 99 mol% or less. The content of protium body is confirmed by mass spectrometry.

[0816] The compound shown in formula (2) can be synthesized by using known substitution reactions and starting materials corresponding to the target substance.

[0817] The following describes specific examples of compounds represented by formula (2). These are merely illustrative examples, and the compounds represented by formula (2) are not limited to the specific examples described below.

[0818] [Chemistry 44]

[0819]

[0820] [Chemistry 45]

[0821]

[0822] [Chemistry 46]

[0823]

[0824] [Chemistry 47]

[0825]

[0826] [Chemistry 48]

[0827]

[0828] In one embodiment, the light-emitting layer comprises a combination of the compound (first host material) represented by formula (1) and the compound (second host material) represented by formula (2) as described in the table below. In the table below, 1-1 to 1-179 represent compound numbers of specific examples of the compound represented by formula (1), and 2-1 to 2-133 represent compound numbers of specific examples of the compound represented by formula (2). The combination of specific examples of the compound of formula (1) and specific examples of the compound of formula (2) is represented by numbers 1 to 10,703 in the table below.

[0829]

[0830]

[0831]

[0832]

[0833]

[0834]

[0835] [Table 7]

[0836]

[0837]

[0838]

[0839]

[0840]

[0841]

[0842] [Table 13]

[0843]

[0844] (Doped materials)

[0845] The dopant material used in the light-emitting layer of the organic EL element of one aspect of the present invention is a compound selected from one or more of the following compounds: compound shown in formula (11), compound shown in formula (21), compound shown in formula (31), compound shown in formula (41), compound shown in formula (51), compound shown in formula (61), compound shown in formula (71), and compound shown in formula (81).

[0846] (The compound shown in formula (11))

[0847] The compound shown in formula (11) will be described.

[0848] [Chemistry 49]

[0849]

[0850] (In formula (11),)

[0851] R 101 ~R 110 Two or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings, or do not form substituted or unsubstituted saturated or unsaturated rings.

[0852] R 101 ~R 110 At least one of them is a monovalent group as shown in the following formula (12).

[0853] R that does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring and is not a monovalent group as shown in formula (12) below 101 ~R 110 Each independently

[0854] hydrogen atom,

[0855] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0856] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[0857] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[0858] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0859] -Si(R 901 (R) 902 (R) 903 ),

[0860] -O-(R 904 ),

[0861] -S-(R 905 ),

[0862] -N(R 906 (R) 907 ),

[0863] Halogen atom, cyano group, nitro group,

[0864] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0865] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0866] R 901 ~R 907 As defined in equation (1) above.

[0867] [Transformation 50]

[0868]

[0869] In equation (12), Ar 101 and Ar 102 Each independently

[0870] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0871] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0872] L 101 ~L 103 Each independently

[0873] single bond,

[0874] Substituted or unsubstituted arylene groups with 6 to 30 cyclic carbon atoms, or

[0875] (Substituted or unsubstituted divalent heterocyclic groups with 5 to 30 cyclic atoms)

[0876] In equation (11), R 101 ~R 110 Two of them are preferably the groups shown in formula (12).

[0877] In one embodiment, the compound represented by formula (11) is shown in the following formula (13).

[0878] [Chemistry 51]

[0879]

[0880] (In equation (13), R) 111 ~R 118 The R in formula (11) that is not a monovalent group as shown in formula (12) 101 ~R 110 Same. Ar 101 Ar 102 L 101 L 102 and L 103 As defined in equation (12) above.

[0881] In equation (11), L 101 Preferably a single bond, L 102 and L103 Single bonds are preferred.

[0882] In one embodiment, the compound represented by formula (11) is represented by formula (14) or (15) below.

[0883] [Chemistry 52]

[0884]

[0885] (In equation (14), R) 111 ~R 118 As defined in equation (13) above. Ar 101 Ar 102 L 102 and L 103 As defined in equation (12) above.

[0886] [Chemistry 53]

[0887]

[0888] (In equation (15), R) 111 ~R 118 As defined in equation (13) above. Ar 101 and Ar 102 As defined in equation (12) above.

[0889] In equations (11) and (12), Ar is preferred. 101 and Ar 102 At least one of them is a group represented by the following formula (16).

[0890] [Chemistry 54]

[0891]

[0892] (In formula (16),)

[0893] X 101 It represents an oxygen atom or a sulfur atom.

[0894] R 121 ~R 127 Two or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings, or do not form substituted or unsubstituted saturated or unsaturated rings.

[0895] R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 121 ~R 127 Each independently

[0896] hydrogen atom,

[0897] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0898] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[0899] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

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

[0901] -Si(R 901 (R) 902 (R) 903 ),

[0902] -O-(R 904 ),

[0903] -S-(R 905 ),

[0904] -N(R 906 (R) 907 ),

[0905] Halogen atom, cyano group, nitro group,

[0906] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0907] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0908] R 901 ~R 907 As defined in equation (1) above.

[0909] X 101 Oxygen atoms are preferred.

[0910] R 121 ~R 127 At least one of them is preferred

[0911] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0912] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[0913] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[0914] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0915] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0916] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0917] In equations (11) and (12), Ar 101 Ar is the group shown in formula (16). 102 Preferably, it is an aryl group with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted.

[0918] In one embodiment, the compound represented by formula (11) is shown in the following formula (17).

[0919] [Chemistry 55]

[0920]

[0921] (In equation (17), R) 111 ~R 118 As defined in equation (13) above. R 121 ~R 127 As defined in equation (16) above.

[0922] R 131 ~R 135 Each independently

[0923] hydrogen atom,

[0924] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0925] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[0926] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[0927] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0928] -Si(R 901 (R) 902 (R) 903 ),

[0929] -O-(R 904 ),

[0930] -S-(R 905 ),

[0931] -N(R 906 (R) 907 ),

[0932] Halogen atom, cyano group, nitro group,

[0933] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0934] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0935] R901 ~R 907 As defined in equation (1) above.

[0936] As a compound represented by formula (11), the following compounds can be cited as specific examples. In the following specific examples, Me represents a methyl group.

[0937] [Chemistry 56]

[0938]

[0939] [Chemistry 57]

[0940]

[0941] [Chem.58]

[0942]

[0943] [Chemistry 59]

[0944]

[0945] [Transformation 60]

[0946]

[0947] [Chemistry 61]

[0948]

[0949] [Chemistry 62]

[0950]

[0951] (The compound shown in formula (21))

[0952] The compound shown in formula (21) will be described.

[0953] [Chemistry 63]

[0954]

[0955] (In equation (21),)

[0956] Z is independently CR a Or N.

[0957] The A1 and A2 rings are each independently an aromatic hydrocarbon ring with 6 to 50 substituted or unsubstituted carbon atoms, or a heterocycle with 5 to 50 substituted or unsubstituted carbon atoms.

[0958] R a When multiple R exist, multiple R aTwo or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings, or do not form substituted or unsubstituted saturated or unsaturated rings.

[0959] R b When multiple R exist, multiple R b Two or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings, or do not form substituted or unsubstituted saturated or unsaturated rings.

[0960] R c When multiple R exist, multiple R c Two or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings, or do not form substituted or unsubstituted saturated or unsaturated rings.

[0961] n21 and n22 are each independent integers from 0 to 4.

[0962] R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. a ~R c Each independently

[0963] hydrogen atom,

[0964] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0965] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[0966] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[0967] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0968] -Si(R 901 (R) 902 (R) 903 ),

[0969] -O-(R 904 ),

[0970] -S-(R 905 ),

[0971] -N(R 906 (R) 907 ),

[0972] Halogen atom, cyano group, nitro group,

[0973] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0974] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0975] R 901 ~R 907 As defined in equation (1) above.

[0976] The "aromatic hydrocarbon rings" of rings A1 and A2 have the same structure as compounds in which hydrogen atoms are introduced onto the "aryl group" as described above. The "aromatic hydrocarbon rings" of rings A1 and A2 include two carbon atoms on the fused 2-ring structure in the center of formula (21) as cyclic atoms. As a specific example of "aromatic hydrocarbon rings with 6 to 50 substituted or unsubstituted cyclic carbon atoms", compounds in specific example group G1 in which hydrogen atoms are introduced onto the "aryl group" can be cited.

[0977] The "heterocycles" of rings A1 and A2 have the same structure as compounds in which hydrogen atoms are introduced onto the aforementioned "heterocyclic group". The "heterocycles" of rings A1 and A2 include two carbon atoms 2 on the fused 2-ring structure at the center of formula (21) as cyclic atoms. As a specific example of "heterocycles with 5 to 50 substituted or unsubstituted cyclic atoms", compounds in which hydrogen atoms are introduced onto the "heterocyclic group" as described in specific example group G2 can be cited.

[0978] R b Any carbon atom bonded to an aromatic hydrocarbon ring forming the A1 ring, or any atom of a heterocycle forming the A1 ring.

[0979] R c Any carbon atom bonded to an aromatic hydrocarbon ring forming an A2 ring, or any atom of a heterocycle forming an A2 ring.

[0980] R a ~R c At least one (preferably two) of the groups is preferably represented by the following formula (21a).

[0981] -L 201 -Ar 201 (21a)

[0982] (In equation (21a),

[0983] L 201 for

[0984] single bond,

[0985] Substituted or unsubstituted arylene groups with 6 to 30 cyclic carbon atoms, or

[0986] A divalent heterocyclic group with 5 to 30 cyclic atoms, substituted or unsubstituted.

[0987] Ar 201 for

[0988] substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms

[0989] Substituted or unsubstituted monovalent heterocyclic groups with 5 to 50 cyclic atoms, or

[0990] The group shown in the following formula (21b).

[0991] [Chemistry 64]

[0992]

[0993] In equation (21b),

[0994] L 211 and L 212 Each independently

[0995] single bond,

[0996] Substituted or unsubstituted arylene groups with 6 to 30 cyclic carbon atoms, or

[0997] A divalent heterocyclic group with 5 to 30 cyclic atoms, substituted or unsubstituted.

[0998] Ar 211 and Ar 212 They bond together to form substituted or unsubstituted saturated or unsaturated rings, or they do not form substituted or unsubstituted saturated or unsaturated rings.

[0999] Ar does not form substituted or unsubstituted saturated or unsaturated rings. 211 and Ar 212 Each independently

[1000] substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms

[1001] (Substituted or unsubstituted monovalent heterocyclic groups with 5 to 50 cyclic atoms)

[1002] In one embodiment, the compound represented by formula (21) is shown in the following formula (22).

[1003] [Chemistry 65]

[1004]

[1005] (In equation (22),)

[1006] R 201 ~R 211 Two or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings, or do not form substituted or unsubstituted saturated or unsaturated rings.

[1007] R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 201 ~R211 Each independently

[1008] hydrogen atom,

[1009] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1010] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1011] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1012] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1013] -Si(R 901 (R) 902 (R) 903 ),

[1014] -O-(R 904 ),

[1015] -S-(R 905 ),

[1016] -N(R 906 (R) 907 ),

[1017] Halogen atom, cyano group, nitro group,

[1018] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1019] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1020] R 901 ~R 907 As defined in equation (1) above.

[1021] R 201 ~R 211 At least one (preferably two) of the groups is preferably the group shown in formula (21a) above. R is preferred. 204 and R 211 The group is represented by formula (21a) above.

[1022] In one embodiment, the compound represented by formula (21) is a compound having a structure represented by formula (21-1) or (21-2) bonded to the A1 ring. Furthermore, in one embodiment, the compound represented by formula (22) is a compound with a structure in R... 204 ~R 207 Compounds having structures represented by formulas (21-1) or (21-2) bonded to a bonded ring.

[1023] [Chemistry 66]

[1024]

[1025] In formula (21-1), each of the two bonding sites * independently bonds to the cyclic carbon atom of the aromatic hydrocarbon ring or the cyclic atom of the heterocycle in formula (21), or to the R in formula (22). 204 ~R 207 Any bond.

[1026] The three bonding sites in formula (21-2)* are each independently bonded to the cyclic carbon atom of the aromatic hydrocarbon ring or the cyclic atom of the heterocycle in formula (21), or to the R in formula (22). 204 ~R 207 Any bond.

[1027] R 221 ~R 227 and R 231 ~R 239 Two or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings, or do not form substituted or unsubstituted saturated or unsaturated rings.

[1028] R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 221 ~R 227 and R 231 ~R 239 Each independently

[1029] hydrogen atom,

[1030] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1031] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1032] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1033] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1034] -Si(R 901 (R) 902 (R) 903 ),

[1035] -O-(R 904 ),

[1036] -S-(R 905 ),

[1037] -N(R 906 (R) 907 ),

[1038] Halogen atom, cyano group, nitro group,

[1039] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1040] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1041] R 901 ~R 907 As defined in equation (1) above.

[1042] In one embodiment, the compound represented by formula (21) is a compound represented by formula (21-3), formula (21-4) or formula (21-5) below.

[1043] [Chemistry 67]

[1044]

[1045] (In equations (21-3), (21-4), and (21-5),)

[1046] A1 ring is defined as in equation (21).

[1047] R 2401 ~R 2407 R with equations (21-1) and (21-2) 221 ~R 227 Same. R 2410 ~R 2417 R in equation (22) 201 ~R 211 Same. 2 Rs 2417 They can be the same or different.

[1048] In one embodiment, the substituted or unsubstituted aromatic hydrocarbon ring with 6 to 50 cyclic carbon atoms in the A1 ring of formula (21-5) is a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted fluorene ring.

[1049] In one embodiment, the heterocycle with 5 to 50 cyclic atoms in the A1 ring of formula (21-5) is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.

[1050] In one embodiment, the compound represented by formula (21) or formula (22) is selected from the compounds represented by formulas (21-6-1) to (21-6-7) below.

[1051] [Chemistry 68]

[1052]

[1053] (In equations (21-6-1) to (21-6-7),)

[1054] R 2421 ~R 2427 R with equations (21-1) and (21-2) 221 ~R 227 Same. R 2430 ~R 2437 and R 2441 ~R 2444 R in equation (22) 201 ~R 211 same.

[1055] X represents O and NR. 901 、or C(R) 902 (R) 903 ).

[1056] R 901 ~R 903 As defined in equation (1) above.

[1057] In one embodiment, in the compound represented by formula (22), R 201 ~R 211 Two or more adjacent rings are bonded together to form substituted or unsubstituted saturated or unsaturated rings. This embodiment is described in detail in the form of the following formula (25).

[1058] (The compound shown in formula (25))

[1059] The compound shown in formula (25) will be described.

[1060] [Chemistry 69]

[1061]

[1062] (In equation (25),)

[1063] Selected from R 251 With R 252 R 252 With R 253 R 254 With R 255 R 255 With R 256 R 256 With R 257 R 258 With R 259 R 259 With R 260 and R 260 With R 261 Two or more pairs of rings in a ring bond with each other to form substituted or unsubstituted saturated or unsaturated rings.

[1064] Among them, R 251 With R 252 The pair and R 252 With R 253 The correct one; R 254 With R 255 The pair and R 255 With R 256 The correct one; R 255 With R 256 The pair and R 256 With R 257 The correct one; R 258 With R 259 The pair and R 259 With R 260 The correct one; and R 259 With R 260 The pair and R 260 With R 261 The pairs do not form a ring at the same time.

[1065] R 251 ~R 261 The two or more rings formed can be the same or different.

[1066] R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 251 ~R 261 Each independently

[1067] hydrogen atom,

[1068] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1069] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1070] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1071] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1072] -Si(R 901 (R) 902 (R) 903 ),

[1073] -O-(R 904 ),

[1074] -S-(R 905 ),

[1075] -N(R 906 (R) 907 ),

[1076] Halogen atom, cyano group, nitro group,

[1077] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1078] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1079] R 901 ~R 907 As defined in equation (1) above.

[1080] In equation (25), R n With R n+1 (n represents an integer selected from 251, 252, 254-256, and 258-260) mutually bonded, and R n With R n+1 The two bonded cyclic carbon atoms together form a substituted or unsubstituted saturated or unsaturated ring. The ring is preferably composed of atoms selected from C, O, S and N atoms, and the number of atoms is preferably 3 to 7, more preferably 5 or 6.

[1081] The compound shown in formula (25) has, for example, two, three, or four ring structures. Two or more ring structures may exist on the same benzene ring in the parent skeleton of formula (25), or they may exist on different benzene rings. For example, when there are three ring structures, each of the three benzene rings in formula (25) may have one ring structure.

[1082] As the above-mentioned ring structure in the compound shown in formula (25), for example, the structures shown in formulas (251) to (260) below can be listed.

[1083] [Chemistry 70]

[1084]

[1085] In equations (251) to (257), *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14 represent R respectively. n With R n+1 The aforementioned two cyclic carbon atoms are bonded together, R n The bonded cyclic carbon atoms can be any of the two cyclic carbon atoms represented by *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14.

[1086] X 2501 For C(R) 2512 (R) 2513 ), NR 2514 、O or S.

[1087] R2501 ~R 2506 and R 2512 ~R 2513 Two or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings, or do not form substituted or unsubstituted saturated or unsaturated rings.

[1088] R does not form substituted or unsubstituted saturated or unsaturated rings. 2501 ~R 2514 Compared with the aforementioned R 251 ~R 261 same.)

[1089] [Chemistry 71]

[1090]

[1091] In equations (258) to (260), *1 and *2, and *3 and *4 respectively represent R. n With R n+1 The aforementioned two cyclic carbon atoms are bonded together, R n The bonded cyclic carbon atoms can be any of the two cyclic carbon atoms represented by *1 and *2, or *3 and *4.

[1092] X 2501 For C(R) 2512 (R) 2513 ), NR 2514 、O or S.

[1093] R 2515 ~R 2525 Two or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings, or do not form substituted or unsubstituted saturated or unsaturated rings.

[1094] R does not form substituted or unsubstituted saturated or unsaturated rings. 2515 ~R 2521 and R 2522 ~R 2525 Compared with the aforementioned R 251 ~R 261 same.)

[1095] In equation (25), R 252 R 254 R 255 R 260 and R 261 At least one (preferably R) 252 R 255 and R 260 At least one, more preferably R 252 Preferably, it is a group that does not form a ring structure.

[1096] (i) In equation (25), through R n With R n+1 When the formed ring structure has substituents, the substituents,

[1097] (ii) In equation (25), R without a ring structure 251 ~R 261 ,and

[1098] (iii) R in equations (251) to (260) 2501 ~R 2514 R 2515 ~R 2525 Preferably, each is an independent hydrogen atom.

[1099] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1100] Alkenyl groups with 2 to 50 carbon atoms (substituted or unsubstituted), alkynyl groups with 2 to 50 carbon atoms (substituted or unsubstituted), cycloalkyl groups with 3 to 50 carbon atoms (substituted or unsubstituted), -N(R) 906 (R) 907 ),

[1101] A substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 carbon atoms, or any group selected from the group consisting of the following groups.

[1102] [Chemistry 72]

[1103]

[1104] (In equations (261) to (264), R) d Each independently

[1105] hydrogen atom,

[1106] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1107] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1108] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1109] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1110] -Si(R 901 (R) 902 (R) 903 ),

[1111] -O-(R 904 ),

[1112] -S-(R 905 ),

[1113] -N(R 906 (R) 907 ),

[1114] Halogen atom, cyano group, nitro group,

[1115] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1116] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1117] X is C(R) 901 (R) 902 ), NR 903 、O or S.

[1118] R 901 ~R 907 As defined in equation (1) above.

[1119] p1 is an integer from 0 to 5, p2 is an integer from 0 to 4, p3 is an integer from 0 to 3, and p4 is an integer from 0 to 7.

[1120] In one embodiment, the compound represented by formula (25) is any one of the following formulas (25-1) to (25-6).

[1121] [Chemistry 73]

[1122]

[1123] In equations (25-1) to (25-6), rings d to i are each independently a substituted or unsubstituted saturated or unsaturated ring. 251 ~R 261 Same as equation (25) above.

[1124] In one embodiment, the compound represented by formula (25) is any one of the following formulas (25-7) to (25-12).

[1125] [Chemistry 74]

[1126]

[1127]

[1128] In equations (25-7) to (25-12), rings d to f, k, and j are each independently a substituted or unsubstituted saturated or unsaturated ring. 251 ~R 261Same as equation (25) above.

[1129] In one embodiment, the compound represented by formula (25) is any one of the following formulas (25-13) to (25-21).

[1130] [Chemistry 75]

[1131]

[1132] In equations (25-13) to (25-21), rings d to k are each independently substituted or unsubstituted saturated or unsaturated rings. 251 ~R 261 Same as equation (25) above.

[1133] As a substituent when the aforementioned ring g or h further has substituents, for example, alkyl groups having 1 to 50 carbon atoms, whether substituted or unsubstituted, can be listed.

[1134] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1135] The groups shown in formulas (261), (263) or (264) above.

[1136] In one embodiment, the compound represented by formula (25) is any one of the following formulas (25-22) to (25-25).

[1137] [Chemistry 76]

[1138]

[1139] In equations (25-22) to (25-25), X 250 Each independently is C(R) 901 (R) 902 ), NR 903 、O or S. R 251 ~R 261 R 271 ~R 278 R in equation (25) above 251 ~R 261 Same. R 901 ~R 903 As defined in equation (1) above.

[1140] In one embodiment, the compound represented by formula (25) is shown in the following formulas (25-26).

[1141] [Chemistry 77]

[1142]

[1143] (In equation (25-26), X) 250 For C(R) 901 (R) 902 ), NR 903 、O or S. R 253 R 254 R 257 R 258 R 261 and R 271 ~R 282 R in equation (25) above 251 ~R 261 Same. R 901 ~R 903 As defined in equation (1) above.

[1144] As a compound represented by formula (21), the following compounds can be cited as specific examples. In the following specific examples, Me represents a methyl group.

[1145] [Chemistry 78]

[1146]

[1147] [Chemistry 79]

[1148]

[1149] [Chemistry 80]

[1150]

[1151] [Chemistry 81]

[1152]

[1153] [Chemistry 82]

[1154]

[1155] [Chemistry 83]

[1156]

[1157] [Chemistry 84]

[1158]

[1159] [Chemistry 85]

[1160]

[1161] [Chemistry 86]

[1162]

[1163] (The compound shown in formula (31))

[1164] The compound shown in formula (31) will be described. The compound shown in formula (31) is the same as the compound shown in formula (21-3) above.

[1165] [Chemistry 87]

[1166]

[1167] (In formula (31),

[1168] R 301 ~R 307 and R 311 ~R 317 Two or more adjacent rings in a group form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[1169] R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 301 ~R 307 and R 311 ~R 317 Each independently

[1170] hydrogen atom,

[1171] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1172] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1173] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1174] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1175] -Si(R 901 (R) 902 (R) 903 ),

[1176] -O-(R 904 ),

[1177] -S-(R 905 ),

[1178] -N(R 906 (R) 907 ),

[1179] Halogen atom, cyano group, nitro group,

[1180] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1181] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1182] R 321 and R 322 Each independently

[1183] hydrogen atom,

[1184] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1185] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1186] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1187] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1188] -Si(R 901 (R) 902 (R) 903 ),

[1189] -O-(R 904 ),

[1190] -S-(R 905 ),

[1191] -N(R 906 (R) 907 ),

[1192] Halogen atom, cyano group, nitro group,

[1193] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1194] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1195] R 901 ~R 907 As defined in equation (1) above.

[1196] R 301 ~R 307 and R 311 ~R 317 A group of two or more adjacent elements is called R. 301 With R 302 R 302 With R 303 R 303 With R 304 R 305 With R 306 R 306 With R 307 R 301 With R302 With R 303 Combinations of, etc.

[1197] In one implementation, R 301 ~R 307 and R 311 ~R 317 At least one, preferably two, are -N(R) 906 (R) 907 The group shown is ).

[1198] In one implementation, R 301 ~R 307 and R 311 ~R 317 Each is independently a hydrogen atom, an aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or a monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms.

[1199] In one embodiment, the compound represented by formula (31) is the compound represented by formula (32) below.

[1200] [Chemistry 88]

[1201]

[1202] (In equation (32),)

[1203] R 331 ~R 334 and R 341 ~R 344 Two or more adjacent rings in a group form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[1204] R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 331 ~R 334 R 341 ~R 344 and R 351 and R 352 Each independently

[1205] hydrogen atom,

[1206] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1207] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1208] R 361 ~R 364 Each independently

[1209] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1210] (Substituted or unsubstituted monovalent heterocyclic groups with 5 to 50 cyclic atoms)

[1211] In one embodiment, the compound represented by formula (31) is the compound represented by formula (33) below.

[1212] [Chemistry 89]

[1213]

[1214] (In equation (33), R) 351 R 352 and R 361 ~R 364 As defined in equation (32) above.

[1215] In one embodiment, the compound represented by formula (31) is the compound represented by formula (34) or (35) below.

[1216] [Chemistry 90]

[1217]

[1218] (In equations (34) and (35),

[1219] R 361 ~R 364 As defined in equation (32) above.

[1220] R 371 ~R 377 and R 380 ~R 386 Two or more adjacent rings in a group form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[1221] R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 371 ~R 377 and R 380 ~R 386 and R 387 Each independently

[1222] hydrogen atom,

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

[1224] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1225] 2 Rs 387 They can be the same or different.

[1226] In one embodiment, the compound represented by formula (31) is a compound represented by formula (34-2) or (35-2) below.

[1227] [Chemistry 91]

[1228]

[1229] In equations (34-2) and (35-2), R 361 ~R 364 R 375 ~R 377 and R 384 ~R 387 As defined in equations (34) and (35) above.

[1230] In one embodiment, R in equations (32), (33), (34), (35), (34-2), and (35-2) 361 ~R 364 Each is independently a substituted or unsubstituted cyclic aryl group (preferably phenyl) with 6 to 50 carbon atoms.

[1231] In one implementation, R in equation (31) 321 and R 322 R in equations (32), (33), (34), (35), (34-2), and (35-2) 351 R 352 and R 387 Each aryl group (preferably phenyl) is independently composed of a hydrogen atom or a cyclic carbon atom with 6 to 50 substituted or unsubstituted carbon atoms.

[1232] In one embodiment, the compound represented by formula (31) is a compound selected from one or more of the compounds represented by formulas (32-11), (34-11) and (35-11) below.

[1233] [Chemistry 92]

[1234]

[1235] In equations (32-11), (34-11), and (35-11),

[1236] R 3301 ~R 3307 and R 3311 ~R 3317 Two or more adjacent rings in a group form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[1237] R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 3301 ~R 3307 and R 3311 ~R 3317 and R 3331 Each group is independently composed of a hydrogen atom, an aryl group with 6 to 20 substituted or unsubstituted cyclic carbon atoms, or a monovalent heterocyclic group with 5 to 20 substituted or unsubstituted cyclic atoms. Two R groups 3331 They can be the same or different.

[1238] R 3321 ~R 3324 Each group is independently an aryl group with 6 to 20 cyclic carbon atoms (substituted or unsubstituted), or a monovalent heterocyclic group with 5 to 20 cyclic carbon atoms (substituted or unsubstituted).

[1239] In one embodiment, the compound selected from one or more of formulas (32-11), (34-11), and (35-11) is a compound selected from one or more of formulas (32-12), (34-12), and (35-12).

[1240] [Chemistry 93]

[1241]

[1242] In equations (32-12), (34-12), and (35-12), R 3321 ~R 3324 and R 3331 As defined in equations (32-11), (34-11), and (35-11) above.

[1243] In one embodiment, in equations (32-11), (34-11), (35-11), (32-12), (34-12), and (35-12), R 3321 ~R 3324 Each can be a substituted or unsubstituted phenyl group.

[1244] In one embodiment, in equations (32-11), (34-11), (35-11), (32-12), (34-12), and (35-12), the two R's 3331 Each is a hydrogen atom.

[1245] In one embodiment, the substituents referred to as "substituted or unsubstituted" in formulas (32-11), (34-11), (35-11), (32-12), (34-12), and (35-12) are selected from alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 20 cyclic carbon atoms, and monovalent heterocyclic groups having 5 to 20 cyclic carbon atoms.

[1246] In one embodiment, in formulas (32-11), (34-11), (35-11), (32-12), (34-12), and (35-12), the substituents referred to as "substituted or unsubstituted" are alkyl groups having 1 to 5 carbon atoms.

[1247] In one embodiment, in equations (32-11), (34-11), (35-11), (32-12), (34-12), and (35-12), R 3321 ~R 3324 Each is independently a substituted or unsubstituted phenyl group, with 2 Rs. 3331 They are hydrogen atoms.

[1248] In one embodiment, in equations (32-11), (34-11), (35-11), (32-12), (34-12), and (35-12), R 3321 ~R 3324 Each is independently a substituted or unsubstituted phenyl group, with 2 Rs. 3331 The substituents, which are hydrogen atoms respectively, are selected from alkyl groups with 1 to 20 carbon atoms, aryl groups with 6 to 20 cyclic carbon atoms, and monovalent heterocyclic groups with 5 to 20 cyclic carbon atoms when referred to as "substituted or unsubstituted".

[1249] In one embodiment, in equations (32-11), (34-11), (35-11), (32-12), (34-12), and (35-12), R 3321 ~R 3324 Each is independently a substituted or unsubstituted phenyl group, with 2 Rs. 3331 When the substituents are hydrogen atoms and are referred to as "substituted or unsubstituted", they are alkyl groups with 1 to 5 carbon atoms.

[1250] In one embodiment, in the compound represented by formula (31), R 301 ~R 307 and R 311 ~R 317 Two or more adjacent rings form a group of substituted or unsubstituted saturated or unsaturated rings.

[1251] In one embodiment, the compound represented by formula (31) is one or more compounds selected from the compounds represented by formulas (36-1) to (36-6) below.

[1252] [Chemistry 94]

[1253]

[1254] (In equations (36-1) to (36-6),

[1255] R3605 ~R 3607 R 3615 ~R 3617 and R 3631 Two or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings, or do not form the aforementioned rings.

[1256] R 3601 ~R 3604 R 3611 ~R 3614 and R 3621 ~R 3628 Two or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings, or do not form the aforementioned rings.

[1257] The aforementioned ring R is not formed 3601 ~R 3607 R 3611 ~R 3617 R 3621 ~R 3628 and R 3631 Each independently

[1258] Hydrogen atom, halogen atom, cyano group, nitro group

[1259] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1260] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1261] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1262] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1263] -Si(R 901 (R) 902 (R) 903 ),

[1264] -O-(R 904 ),

[1265] -S-(R 905 ),

[1266] -N(R 906 (R) 907 ),

[1267] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1268] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1269] R901 ~R 907 Each independently

[1270] hydrogen atom,

[1271] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1272] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1273] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1274] A monovalent heterocyclic group, with 5 to 50 cyclic atoms, either substituted or unsubstituted. R 901 ~R 907 When there are more than two, more than two R 901 ~R 907 They can be the same or different.

[1275] X1 is selected from O, S, and N(R) 3641 Two X1s can be the same, or they can be different.

[1276] R 3641 With selection from R 3601 ~R 3604 R 3611 ~R 3614 R 3624 and R 3628 One or more of them are bonded to each other to form substituted or unsubstituted saturated or unsaturated rings, or they do not form the aforementioned rings.

[1277] The aforementioned ring R is not formed 3641 For hydrogen atoms,

[1278] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1279] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1280] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1281] (Substituted or unsubstituted monovalent heterocyclic groups with 5 to 50 cyclic atoms)

[1282] In one embodiment, the compound represented by formula (31) is a compound represented by formula (36-1) or formula (36-2), and in another embodiment, it is a compound represented by formula (36-1).

[1283] In one embodiment, in the compounds represented by formulas (36-1) to (36-6), 2 R 3631 It is a phenyl group.

[1284] In one embodiment, in the compounds represented by formulas (36-1) to (36-6), X1 is N(R) 3641 ).

[1285] In one embodiment, in the compounds represented by formulas (36-1) to (36-6), R 3641 It is an aryl group with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted.

[1286] In one embodiment, the compound represented by formula (31) is the compound represented by formula (36-1-1) below.

[1287] [Chemistry 95]

[1288]

[1289] (In equation (36-1-1), R) 3001 R 3002 R 3005 ~R 3007 R 3010 R 3011 R 3014 ~R 3016 and R 3031 ~R 3034 Two or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings, or do not form substituted or unsubstituted saturated or unsaturated rings.

[1290] X a Each is independently selected from O, S, and N(R) 3035 ).

[1291] R 3035 With R 3031 They may bond together to form substituted or unsubstituted saturated or unsaturated rings, or they may not form the aforementioned rings.

[1292] R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 3001 R 3002 R 3005 ~R 3007 R 3010 R 3011 R 3014 ~R 3016 and R 3031 ~R 3035 and R 3021 R 3022 Each independently

[1293] hydrogen atom,

[1294] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1295] (Substituted or unsubstituted monovalent heterocyclic groups with 5 to 50 cyclic atoms)

[1296] In one embodiment, the substituents referred to as "substituted or unsubstituted" in formulas (31) to (35), (34-2), (35-2), (32-11), (34-11), (35-11), (32-12), (34-12), (35-12), (36-1) to (36-6), and (36-1-1) are...

[1297] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1298] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1299] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1300] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1301] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1302] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1303] As a compound represented by formula (31), the following compounds can be cited as specific examples. In the following specific examples, Me represents a methyl group.

[1304] [Chemistry 96]

[1305]

[1306] [Chemistry 97]

[1307]

[1308] [Chem. 98]

[1309]

[1310] [Chemistry 99]

[1311]

[1312] [Chemistry 100]

[1313]

[1314] [Chemistry 101]

[1315]

[1316] [Chemistry 102]

[1317]

[1318] [Chemistry 103]

[1319]

[1320] [Chemistry 104]

[1321]

[1322] [Chemistry 105]

[1323]

[1324] [Chemistry 106]

[1325]

[1326] [Chemistry 107]

[1327]

[1328] [Chemistry 108]

[1329]

[1330] [Chemistry 109]

[1331]

[1332] [Chemical 110]

[1333]

[1334] [Chemistry 111]

[1335]

[1336] [Chemistry 112]

[1337]

[1338] [Chemistry 113]

[1339]

[1340] [Chemistry 114]

[1341]

[1342] [Chemistry 115]

[1343]

[1344] [Chemistry 116]

[1345]

[1346] [Chemistry 117]

[1347]

[1348] [Chemistry 118]

[1349]

[1350] [Chemistry 119]

[1351]

[1352] [Chemistry 120]

[1353]

[1354] [Chemistry 121]

[1355]

[1356] [Chemistry 122]

[1357]

[1358] (The compound shown in formula (41))

[1359] The compound shown in formula (41) will be described.

[1360] [Chemistry 123]

[1361]

[1362] (In equation (41), ring a, ring b, and ring c are each independently...)

[1363] Substituted or unsubstituted cyclic aromatic hydrocarbon rings with 6 to 50 carbon atoms, or...

[1364] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1365] R 401 and R 402 Each ring independently bonds to the aforementioned a-ring, b-ring, or c-ring to form a substituted or unsubstituted heterocycle, or a heterocycle that does not form a substituted or unsubstituted heterocycle.

[1366] R does not form the aforementioned substituted or unsubstituted heterocycles 401 and R 402 Each independently

[1367] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1368] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1369] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1370] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1371] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1372] (Substituted or unsubstituted monovalent heterocyclic groups with 5 to 50 cyclic atoms)

[1373] Rings a, b, and c are rings formed by the fusion of a central fused 2-ring structure of formula (41) consisting of a B atom and two N atoms (a substituted or unsubstituted aromatic hydrocarbon ring with 6 to 50 cyclic carbon atoms, or a substituted or unsubstituted heterocycle with 5 to 50 cyclic atoms).

[1374] The "aromatic hydrocarbon rings" of rings a, b, and c have the same structure as compounds in which hydrogen atoms are introduced onto the "aryl" group described above. The "aromatic hydrocarbon ring" of ring a includes three carbon atoms on the fused 2-ring structure at the center of formula (41) as cyclic atoms. The "aromatic hydrocarbon rings" of rings b and c include two carbon atoms on the fused 2-ring structure at the center of formula (41) as cyclic atoms. As a specific example of "aromatic hydrocarbon rings with 6 to 50 substituted or unsubstituted cyclic carbon atoms", compounds in which hydrogen atoms are introduced onto the "aryl" group described in specific example group G1 can be cited.

[1375] The "heterocycles" of rings a, b, and c have the same structure as compounds in which hydrogen atoms are introduced onto the aforementioned "heterocyclic group". The "heterocycle" of ring a includes the three carbon atoms of the fused 2-ring structure in the center of formula (41) as cyclic atoms. The "heterocycles" of rings b and c include the two carbon atoms of the fused 2-ring structure in the center of formula (41) as cyclic atoms. As a specific example of "heterocycles with 5 to 50 substituted or unsubstituted cyclic atoms", compounds in which hydrogen atoms are introduced onto the "heterocyclic group" described in specific example group G2 can be listed.

[1376] R 401 and R 402 Each ring independently bonds to ring a, ring b, or ring c to form substituted or unsubstituted heterocycles. These heterocycles contain the nitrogen atom in the fused 2-ring structure at the center of formula (41). These heterocycles may also contain heteroatoms other than the nitrogen atom. R 401 and R 402 Bonding with ring a, ring b, or ring c specifically refers to the bonding between atoms constituting ring a, ring b, or ring c and atoms constituting ring R. 401 and R 402Atomic bonding. For example, R 401 Bonded to the α ring, it can form a ring containing R 401 A nitrogen-containing heterocycle obtained by fusion of the ring with the a ring, resulting in a 2-ring fused (or 3-ring fused or more) nitrogen-containing heterocycle. Specific examples of such nitrogen-containing heterocycles include compounds in specific example group G2 corresponding to heterocyclic groups fused with 2 or more nitrogen-containing rings.

[1377] R 401 When bonded to the b-ring, R 402 When bonded to the α ring, and R 402 The same applies when bonding with the c-ring.

[1378] In one embodiment, rings a, b, and c in formula (41) are each independently a substituted or unsubstituted aromatic hydrocarbon ring with 6 to 50 carbon atoms.

[1379] In one embodiment, rings a, b, and c in formula (41) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.

[1380] In one implementation, R in equation (41) 401 and R 402 Each is independently an aryl group with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted, or a monovalent heterocyclic group with 5 to 50 cyclic carbon atoms, preferably an aryl group with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted.

[1381] In one embodiment, the compound represented by formula (41) is the compound represented by formula (42) below.

[1382] [Chemistry 124]

[1383]

[1384] (In equation (42),)

[1385] R 401A With selection from R 411 and R 421 One or more of the components are bonded together to form a substituted or unsubstituted heterocycle, or no substituted or unsubstituted heterocycle is formed. R 402A With selection from R 413 and R 414 One or more of them are bonded together to form a substituted or unsubstituted heterocycle, or not a substituted or unsubstituted heterocycle.

[1386] R does not form the aforementioned substituted or unsubstituted heterocycles 401A and R 402A Each independently

[1387] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1388] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1389] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1390] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1391] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1392] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1393] R 411 ~R 421 Two or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings, or do not form substituted or unsubstituted saturated or unsaturated rings.

[1394] R consists of the aforementioned substituted or unsubstituted heterocycles or does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 411 ~R 421 Each independently

[1395] hydrogen atom,

[1396] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1397] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1398] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1399] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1400] -Si(R 901 (R) 902 (R) 903 ),

[1401] -O-(R 904 ),

[1402] -S-(R 905 ),

[1403] -N(R 906 (R) 907 ),

[1404] Halogen atom, cyano group, nitro group,

[1405] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1406] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1407] R 901 ~R 907 As defined in equation (1) above.

[1408] R in equation (42) 401A and R 402A For R in equation (41) 401 and R 402 The corresponding functional group.

[1409] For example, R 401A With R 411 These are nitrogen-containing heterocycles formed by bonding together to form a ring containing the ring and then fusing it with a benzene ring corresponding to the a ring, resulting in a 2-ring fused (or 3-ring fused or more) nitrogen-containing heterocycle. Specific examples of such nitrogen-containing heterocycles include compounds in specific example group G2 corresponding to the nitrogen-containing 2-ring fused or more heterocyclic groups. R 401A With R 412 During bonding, R 402A With R 413 During bonding, and R 402A With R 414 The bonding process is the same as described above.

[1410] R 411 ~R 421 Two or more adjacent rings in a group can bond together to form substituted or unsubstituted saturated or unsaturated rings. For example, R... 11 With R 12 The structures formed by fusion of the six-membered rings bonded to them can be benzene rings, indole rings, pyrrole rings, benzofuran rings, or benzothiophene rings. The fused rings formed can be naphthol rings, carbazole rings, indole rings, dibenzofuran rings, or dibenzothiophene rings.

[1411] In one implementation, R contributes to cyclic formation 411 ~R 421 Each of the following groups is independently a hydrogen atom, an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, an aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or a monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic carbon atoms.

[1412] In one implementation, R contributes to cyclic formation 411 ~R 421 Each is independently a hydrogen atom, an aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or a monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms.

[1413] In one implementation, R contributes to cyclic formation 411 ~R 421Each is an alkyl group consisting of 1 to 50 hydrogen atoms, or substituted or unsubstituted carbon atoms.

[1414] In one implementation, R contributes to cyclic formation 411 ~R 421 Each is an alkyl group consisting of 1 to 50 hydrogen atoms, or substituted or unsubstituted carbon atoms; R 411 ~R 421 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1415] In one embodiment, the compound represented by the aforementioned formula (42) is the compound represented by the following formula (43).

[1416] [Chemistry 125]

[1417]

[1418] (In formula (43),

[1419] R 431 With R 446 Bonding can form substituted or unsubstituted heterocycles, or no substituted or unsubstituted heterocycles may be formed. R 433 With R 447 Bonding can form substituted or unsubstituted heterocycles, or no substituted or unsubstituted heterocycles may be formed. R 434 With R 451 Bonding can form substituted or unsubstituted heterocycles, or no substituted or unsubstituted heterocycles may be formed. R 441 With R 442 Bonding, forming substituted or unsubstituted heterocycles, or not forming substituted or unsubstituted heterocycles.

[1420] R 431 ~R 451 Two or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings, or do not form substituted or unsubstituted saturated or unsaturated rings.

[1421] R consists of the aforementioned substituted or unsubstituted heterocycles or does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 431 ~R 451 Each independently

[1422] hydrogen atom,

[1423] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1424] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1425] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1426] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1427] -Si(R 901 (R) 902 (R) 903 ),

[1428] -O-(R 904 ),

[1429] -S-(R 905 ),

[1430] -N(R 906 (R) 907 ),

[1431] Halogen atom, cyano group, nitro group,

[1432] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1433] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1434] R 901 ~R 907 As defined in equation (1) above.

[1435] R 431 With R 446 Bonding can form substituted or unsubstituted heterocyclic rings. For example, R... 431 With R 446 bonded to form R 46 This refers to nitrogen-containing heterocycles formed by the fusion of bonded benzene rings, rings containing nitrogen (N), and benzene rings corresponding to the a ring, resulting in fusion of three or more nitrogen-containing rings. Specific examples of such nitrogen-containing heterocycles include compounds in specific example group G2 corresponding to nitrogen-containing fused heterocyclic groups, etc. R 433 With R 447 During bonding, R 434 With R 451 During bonding, and R 441 With R 442 The bonding process is the same as described above.

[1436] In one implementation, R contributes to cyclic formation 431 ~R 451 Each of the following groups is independently a hydrogen atom, an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, an aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or a monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic carbon atoms.

[1437] In one implementation, R contributes to cyclic formation 431 ~R 451Each is independently a hydrogen atom, an aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or a monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms.

[1438] In one implementation, R contributes to cyclic formation 431 ~R 451 Each is an alkyl group consisting of 1 to 50 hydrogen atoms, or substituted or unsubstituted carbon atoms.

[1439] In one implementation, R contributes to cyclic formation 431 ~R 451 Each is an alkyl group consisting of 1 to 50 hydrogen atoms, or substituted or unsubstituted carbon atoms; R 431 ~R 451 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1440] In one embodiment, the compound represented by the aforementioned formula (43) is the compound represented by the following formula (43A).

[1441] [Chemistry 126]

[1442]

[1443] (In formula (43A),

[1444] R 461 for

[1445] hydrogen atom,

[1446] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1447] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1448] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1449] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms, or

[1450] Aryl groups with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted.

[1451] R 462 ~R 465 Each independently

[1452] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1453] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1454] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1455] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms, or

[1456] Aryl groups, with or without substitution, forming cyclic carbon atoms ranging from 6 to 50.

[1457] In one implementation, R 461 ~R 465 Each is independently an alkyl group with 1 to 50 carbon atoms, either substituted or unsubstituted, or an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[1458] In one implementation, R 461 ~R 465 Each is an alkyl group, with 1 to 50 carbon atoms, whether substituted or unsubstituted.

[1459] In one embodiment, the compound represented by the aforementioned formula (43) is the compound represented by the following formula (43B).

[1460] [Chemistry 127]

[1461]

[1462] (In formula (43B),

[1463] R 471 and R 472 Each independently

[1464] hydrogen atom,

[1465] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1466] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1467] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1468] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1469] -N(R 906 (R) 907 ),or

[1470] Aryl groups with 6 to 50 cyclic carbon atoms, substituted or unsubstituted.

[1471] R 473 ~R 475 Each independently

[1472] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1473] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1474] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1475] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1476] -N(R 906 (R) 907 ),or

[1477] Aryl groups with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted.

[1478] R 906 and R 907 As defined in equation (1) above.

[1479] In one embodiment, the compound represented by the aforementioned formula (43) is the compound represented by the following formula (43B').

[1480] [Chemistry 128]

[1481]

[1482] (In formula (43B'), R) 472 ~R 475 As defined in equation (43B) above.

[1483] In one implementation, R 471 ~R 475 At least one of them is

[1484] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1485] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1486] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1487] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1488] -N(R 906 (R) 907 ),or

[1489] Aryl groups with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted.

[1490] In one implementation,

[1491] R 472 for

[1492] hydrogen atom,

[1493] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1494] -N(R906 (R) 907 ),or

[1495] Aryl groups with 6 to 50 cyclic carbon atoms, substituted or unsubstituted.

[1496] R 471 and R 473 ~R 475 Each independently

[1497] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1498] -N(R 906 (R) 907 ),or

[1499] Aryl groups with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted.

[1500] In one embodiment, the compound represented by the aforementioned formula (43) is the compound represented by the following formula (43C).

[1501] [Chemistry 129]

[1502]

[1503] (In formula (43C),)

[1504] R 481 and R 482 Each independently

[1505] hydrogen atom,

[1506] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1507] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1508] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1509] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms, or

[1510] Aryl groups with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted.

[1511] R 483 ~R 486 Each independently

[1512] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1513] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1514] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1515] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms, or

[1516] Aryl groups, with or without substitution, forming cyclic carbon atoms ranging from 6 to 50.

[1517] In one embodiment, the compound represented by the aforementioned formula (43) is the compound represented by the following formula (43C').

[1518] [Chemistry 130]

[1519]

[1520] (In formula (43C'), R) 483 ~R 486 As defined in equation (43C) above.

[1521] In one implementation, R 481 ~R 486 Each is independently an alkyl group with 1 to 50 carbon atoms, either substituted or unsubstituted, or an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[1522] In one implementation, R 481 ~R 486 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 cyclic carbon atoms.

[1523] In one embodiment, the compound represented by the aforementioned formula (43) is the compound represented by the following formula (43D).

[1524] [Chemistry 131]

[1525]

[1526] (In equation (43D),)

[1527] R 4611 Hydrogen atom, unsubstituted alkyl group with 1 to 6 carbon atoms, unsubstituted cycloalkyl group with 3 to 10 cyclic carbon atoms, -Si(R 911 (R) 912 (R) 913 ), or -N(R 914 (R) 915 ).

[1528] R 4612 ~R 4615 Each is independently an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted cycloalkyl group having 3 to 10 carbon atoms, or a -Si(R) group. 911 (R) 912 (R) 913 ).

[1529] R 911 ~R 913 Each is independently an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted cyclic aryl group having 6 to 18 carbon atoms.

[1530] R 914 ~R 915 Each is an unsubstituted aryl group with 6 to 18 cyclic carbon atoms.

[1531] In one implementation, in equation (43D), R 4611 It consists of hydrogen atoms, unsubstituted alkyl groups having 1 to 6 carbon atoms, or -N(R) atoms. 914 (R) 915 ).

[1532] In one implementation, in equation (43D), R 4612 ~R 4615 Each is independently an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted cycloalkyl group having 3 to 10 carbon atoms.

[1533] In one implementation, in equation (43D), R 4611 -N(R) 914 (R) 915 ), R 4612 ~R 4615 Each is an unsubstituted alkyl group having 1 to 6 carbon atoms.

[1534] In one implementation, in equation (43D), R 4611 R is an unsubstituted alkyl group having 1 to 6 carbon atoms. 4612 ~R 4615 Each is an unsubstituted alkyl group having 1 to 6 carbon atoms.

[1535] In one implementation, in equation (43D), R 4611 For hydrogen atoms, R 4612 ~R 4615 Each is independently an unsubstituted alkyl group having 1 to 6 carbon atoms or an unsubstituted cycloalkyl group having 3 to 10 carbon atoms.

[1536] In one embodiment, in formula (43D), the ingredients are selected from R. 914 and R 915 At least one of the hydrogen atoms in one or more of them is a deuterium atom.

[1537] The compound shown in formula (41) can be prepared as follows: first, an intermediate is prepared by linking rings a, b, and c with linking groups (groups containing N-R1 and groups containing N-R2) (reaction 1); and the final product is prepared by linking rings a, b, and c with linking groups (groups containing B) (reaction 2). In reaction 1, an amination reaction such as the Buchwald-Hartwig reaction can be used. In reaction 2, a tandem heterogeneous Friedel-Crafts reaction can be used.

[1538] The following are specific examples of compounds represented by formula (41), which are merely illustrative examples and are not limited to the specific examples described below. In the following specific examples, Me represents methyl and tBu represents tert-butyl.

[1539] [Chemistry 132]

[1540]

[1541] [Chemistry 133]

[1542]

[1543] [Chemistry 134]

[1544]

[1545] [Chemistry 135]

[1546]

[1547] [Chemistry 136]

[1548]

[1549] [Chemistry 137]

[1550]

[1551] [Chemistry 138]

[1552]

[1553] [Chemistry 139]

[1554]

[1555] [Chemistry 140]

[1556]

[1557] [Chemistry 141]

[1558]

[1559] [Chemistry 142]

[1560]

[1561] [Chemistry 143]

[1562]

[1563] [Chemistry 144]

[1564]

[1565] [Chemistry 145]

[1566]

[1567] [Chemistry 146]

[1568]

[1569] [Chemistry 147]

[1570]

[1571] [Chemistry 148]

[1572]

[1573] (The compound shown in formula (51))

[1574] The compound shown in formula (51) will be described.

[1575] [Chemistry 149]

[1576]

[1577] (In formula (51),

[1578] The r-ring is a ring as shown in equation (52) or equation (53) that is fused at any position between adjacent rings.

[1579] The q ring and the s ring are each independently a ring as shown in equation (54) that is fused at any position of an adjacent ring.

[1580] The p-ring and t-ring are each independently the structure shown in equation (55) or equation (56) where they are fused at any position of adjacent rings.

[1581] R 501 When multiple R exist, multiple adjacent R 501 They bond together to form substituted or unsubstituted saturated or unsaturated rings, or they do not form substituted or unsubstituted saturated or unsaturated rings.

[1582] X 501 For oxygen atoms, sulfur atoms, or NR502 .

[1583] R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 501 and R 502 for

[1584] hydrogen atom,

[1585] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1586] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1587] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1588] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1589] -Si(R 901 (R) 902 (R) 903 ),

[1590] -O-(R 904 ),

[1591] -S-(R 905 ),

[1592] -N(R 906 (R) 907 ),

[1593] Halogen atom, cyano group, nitro group,

[1594] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1595] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1596] R 901 ~R 907 As defined in equation (1) above.

[1597] Ar 501 and Ar 502 Each independently

[1598] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1599] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1600] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1601] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1602] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1603] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1604] L 501 for

[1605] Substituted or unsubstituted alkylene groups having 1 to 50 carbon atoms

[1606] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1607] Substituted or unsubstituted ynyl groups with 2 to 50 carbon atoms

[1608] Substituted or unsubstituted cycloalkylene groups with 3 to 50 carbon atoms

[1609] Substituted or unsubstituted arylene groups with 6 to 50 cyclic carbon atoms, or

[1610] A divalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1611] m1 is an independent integer from 0 to 2, m2 is an independent integer from 0 to 4, m3 is an independent integer from 0 to 3, and m4 is an independent integer from 0 to 5. R 501 When multiple R exist, multiple R 501 They can be the same or different.

[1612] In equation (51), each of the p-rings to t-rings is fused with two carbon atoms from its adjacent ring. The position and direction of fusion are not limited and can be fused at any position or in any direction.

[1613] In one embodiment, in equation (52) or (53) of the r ring, R 501 It is a hydrogen atom.

[1614] In one embodiment, the compound represented by formula (51) is any one of the following formulas (51-1) to (51-6).

[1615] [Chemistry 150]

[1616]

[1617] (In equations (51-1) to (51-6), R) 501 X 501 Ar 501 Ar 502 L 501 m1 and m3 are as defined in equation (51) above.

[1618] In one embodiment, the compound represented by formula (51) is any one of the following formulas (51-11) to (51-13).

[1619] [Chemistry 151]

[1620]

[1621] (In equations (51-11) to (51-13), R) 501 X 501 Ar 501 Ar 502 L 501 m1, m3, and m4 are as defined in equation (51) above.

[1622] In one embodiment, the compound represented by formula (51) is any one of the following formulas (51-21) to (51-25).

[1623] [Chemistry 152]

[1624]

[1625] In equations (51-21) to (51-25), R 501 X 501 Ar 501 Ar 502 L 501 m1 and m4 are as defined in equation (51) above.

[1626] In one embodiment, the compound represented by formula (51) is any one of the following formulas (51-31) to (51-33).

[1627] [Chemistry 153]

[1628]

[1629] (In equations (51-31) to (51-33), R) 501 X 501 Ar 501 Ar 502 L 501 m1 to m4 are as defined in equation (51) above.

[1630] In one implementation, Ar 501 and Ar 502 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 cyclic carbon atoms.

[1631] In one implementation, Ar 501 and Ar 502One is an aryl group with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted, and the other is a monovalent heterocyclic group with 5 to 50 cyclic carbon atoms, either substituted or unsubstituted.

[1632] As a compound represented by formula (51), the following compounds can be cited as specific examples. In the following specific examples, Me represents a methyl group.

[1633] [Chemistry 154]

[1634]

[1635] [Chemistry 155]

[1636]

[1637] (The compound shown in formula (61))

[1638] The compound shown in formula (61) will be described.

[1639] [Chemistry 156]

[1640]

[1641] (In formula (61),

[1642] R 601 With R 602 R 602 With R 603 and R 603 With R 604 At least one group of them are bonded together to form a divalent group as shown in the following formula (62).

[1643] R 605 With R 606 R 606 With R 607 and R 607 With R 608 At least one group of them are bonded to each other to form a divalent group as shown in the following formula (63).

[1644] [Chemistry 157]

[1645]

[1646] R 601 ~R 604 The groups that do not form the divalent group shown in the aforementioned formula (62), and R 611 ~R 614 At least one of them is a monovalent group as shown in the following formula (64).

[1647] R 605 ~R 608The groups that do not form the divalent group shown in the aforementioned formula (63), and R 621 ~R 624 At least one of them is a monovalent group as shown in the following formula (64).

[1648] X 601 For oxygen atoms, sulfur atoms, or NR 609 .

[1649] R that does not form the divalent group shown in formulas (62) and (63) above, and is not the monovalent group shown in formula (64) above. 601 ~R 608 R that is not a monovalent group as shown in the aforementioned formula (64) 611 ~R 614 and R 621 ~R 624 and R 609 Each independently

[1650] hydrogen atom,

[1651] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1652] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1653] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1654] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1655] -Si(R 901 (R) 902 (R) 903 ),

[1656] -O-(R 904 ),

[1657] -S-(R 905 ),

[1658] -N(R 906 (R) 907 ),

[1659] Halogen atom, cyano group, nitro group,

[1660] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1661] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1662] R 901 ~R 907 As defined in equation (1) above.

[1663] [Chemistry 158]

[1664]

[1665] In equation (64), Ar 601 and Ar 602 Each independently

[1666] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1667] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1668] L 601 ~L 603 Each independently

[1669] single bond,

[1670] Substituted or unsubstituted arylene groups with 6 to 30 cyclic carbon atoms

[1671] Substituted or unsubstituted divalent heterocyclic groups with 5 to 30 cyclic atoms, or

[1672] A divalent linking group formed by the bonding of 2 to 4 substituted or unsubstituted aryl groups with 6 to 30 carbon atoms and divalent heterocyclic groups with 5 to 30 carbon atoms.

[1673] In formula (61), the positions of the divalent groups shown in formula (62) and formula (63) are not particularly limited and can be in R. 601 ~R 608 The group forms at possible positions.

[1674] In one embodiment, the compound represented by formula (61) is any one of the following formulas (61-1) to (61-6).

[1675] [Chemistry 159]

[1676]

[1677] (In equations (61-1) to (61-6), X) 601 As defined in equation (61) above.

[1678] R 601 ~R 624 At least two of them are monovalent groups as shown in the aforementioned formula (64).

[1679] R is not a monovalent group as shown in the aforementioned formula (64) 601 ~R 624 Each independently

[1680] hydrogen atom,

[1681] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1682] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1683] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1684] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1685] -Si(R 901 (R) 902 (R) 903 ),

[1686] -O-(R 904 ),

[1687] -S-(R 905 ),

[1688] -N(R 906 (R) 907 ),

[1689] Halogen atom, cyano group, nitro group,

[1690] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1691] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1692] R 901 ~R 907 As defined in equation (1) above.

[1693] In one embodiment, the compound represented by formula (61) is any one of the following formulas (61-7) to (61-18).

[1694] [Chemistry 160]

[1695]

[1696] In equations (61-7) to (61-18), X 601 As defined in formula (61) above. * represents a single bond bonded to the monovalent group shown in formula (64) above. R 601 ~R 624 R that is not a monovalent group as shown in the aforementioned formula (64) 601 ~R 624 same.)

[1697] R that does not form the divalent group shown in formulas (62) and (63) above, and is not the monovalent group shown in formula (64) above. 601 ~R 608 R, and R that is not a monovalent group as shown in the aforementioned formula (64) 611 ~R 614 and R 621 ~R 624 Preferred to be independent

[1698] hydrogen atom,

[1699] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1700] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1701] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1702] The cyclic group may be a cyclic alkyl group with 3 to 50 cyclic carbon atoms, a cyclic aryl group with 6 to 50 cyclic carbon atoms, or a monovalent heterocyclic group with 5 to 50 cyclic carbon atoms, substituted or unsubstituted. The monovalent group shown in formula (64) is preferably shown in formula (65) or (66) below.

[1703] [Chemistry 161]

[1704]

[1705] (In equation (65), R) 631 ~R 640 Each independently

[1706] hydrogen atom,

[1707] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1708] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1709] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1710] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1711] -Si(R 901 (R) 902 (R) 903 ),

[1712] -O-(R 904 ),

[1713] -S-(R 905 ),

[1714] -N(R906 (R) 907 ),

[1715] Halogen atom, cyano group, nitro group,

[1716] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1717] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1718] R 901 ~R 907 As defined in equation (1) above.

[1719] [Chemistry 162]

[1720]

[1721] (In formula (66), Ar) 601 L 601 and L 603 As defined in equation (64) above. HAr 601 The structure is shown in the following formula (67).

[1722] [Chemistry 163]

[1723]

[1724] In equation (67), X 602 It consists of oxygen or sulfur atoms.

[1725] R 641 ~R 648 Either of them is bonded to L 603 A single key.

[1726] R is not a single-key letter. 641 ~R 648 Each independently

[1727] hydrogen atom,

[1728] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1729] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1730] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1731] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1732] -Si(R 901 (R) 902 (R) 903 ),

[1733] -O-(R 904 ),

[1734] -S-(R 905 ),

[1735] -N(R 906 (R) 907 ),

[1736] Halogen atom, cyano group, nitro group,

[1737] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1738] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1739] R 901 ~R 907 As defined in equation (1) above.

[1740] As a compound represented by formula (61), in addition to the compounds described in International Publication No. 2014 / 104144, the following compounds may be cited as specific examples. In the following specific examples, Me represents methyl.

[1741] [Chemistry 164]

[1742]

[1743] [Chemistry 165]

[1744]

[1745] [Chemistry 166]

[1746]

[1747] [Chemistry 167]

[1748]

[1749] (The compound shown in formula (71))

[1750] The compound shown in formula (71) will be described.

[1751] [Chemistry 168]

[1752]

[1753] (In formula (71),

[1754] A 701 Ring and A 702 Each ring is independent of the others.

[1755] Substituted or unsubstituted cyclic aromatic hydrocarbon rings with 6 to 50 carbon atoms, or...

[1756] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1757] Selected from A 701 Ring and A 702 One or more rings are bonded to the bonding sites of the structure shown in equation (72) below.

[1758] [Chemistry 169]

[1759]

[1760] In equation (72),

[1761] A 703 Each ring is independent of the others.

[1762] Substituted or unsubstituted cyclic aromatic hydrocarbon rings with 6 to 50 carbon atoms, or...

[1763] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1764] X 701 For NR 703 C(R) 704 (R) 705 ), Si(R) 706 (R) 707 ), Ge(R) 708 (R) 709 ), O, S or Se.

[1765] R 701 and R 702 They bond together to form substituted or unsubstituted saturated or unsaturated rings, or they do not form substituted or unsubstituted saturated or unsaturated rings.

[1766] R does not form substituted or unsubstituted saturated or unsaturated rings. 701 and R 702 and R 703 ~R 709 Each independently

[1767] hydrogen atom,

[1768] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1769] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1770] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1771] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1772] -Si(R 901 (R) 902 (R) 903 ),

[1773] -O-(R 904 ),

[1774] -S-(R 905 ),

[1775] -N(R 906 (R) 907 ),

[1776] Halogen atom, cyano group, nitro group,

[1777] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1778] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1779] R 901 ~R 907 As defined in equation (1) above.

[1780] Selected from A 701 Ring and A 702 One or more of the rings are bonded to the bonding sites of the structure shown in equation (72). That is, in one embodiment, A 701 The cyclic carbon atom of the aforementioned aromatic hydrocarbon ring, or the cyclic atom of the aforementioned heterocycle, is bonded to the bonding site* of the structure shown in formula (72). Furthermore, in one embodiment, A 702 The cyclic carbon atom of the aforementioned aromatic hydrocarbon ring, or the cyclic atom of the aforementioned heterocycle, is bonded to the bonding site of the structure shown in formula (72).

[1781] In one implementation, A 701 Ring and A 702 One or both of the rings are bonded to the group shown in the following formula (73).

[1782] [Chemistry 170]

[1783]

[1784] (In equation (73), Ar) 701 and Ar 702 Each independently

[1785] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1786] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1787] L 701 ~L 703 Each independently

[1788] single bond,

[1789] Substituted or unsubstituted arylene groups with 6 to 30 cyclic carbon atoms

[1790] Substituted or unsubstituted divalent heterocyclic groups with 5 to 30 cyclic atoms, or

[1791] They are formed by 2 to 4 bonded divalent linkage groups.

[1792] In one implementation, except A 701 Outside the ring road, A 702 The cyclic carbon atom of the aforementioned aromatic hydrocarbon ring, or the cyclic atom of the aforementioned heterocycle, is bonded to the bonding site of the structure shown in formula (72). In this case, the structure shown in formula (72) may be the same or different.

[1793] In one implementation, R 701 and R 702 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 cyclic carbon atoms.

[1794] In one implementation, R 701 and R 702 They bond together to form a fluorene structure.

[1795] In one implementation, ring A 701 And Ring A 702 A ring of aromatic hydrocarbons with 6 to 50 carbon atoms, either substituted or unsubstituted, such as a substituted or unsubstituted benzene ring.

[1796] In one implementation, ring A 703 A ring of aromatic hydrocarbons with 6 to 50 carbon atoms, either substituted or unsubstituted, such as a substituted or unsubstituted benzene ring.

[1797] In one implementation, X 701 It can be O or S.

[1798] As a compound represented by formula (71), the following compounds can be cited as specific examples. In the following specific examples, Me represents a methyl group.

[1799] [Chemistry 171]

[1800]

[1801] [Chemistry 172]

[1802]

[1803] [Chemistry 173]

[1804]

[1805] [Chemistry 174]

[1806]

[1807] (The compound shown in formula (81))

[1808] The compound shown in formula (81) will be described.

[1809] [Chemistry 175]

[1810]

[1811] (In formula (81),)

[1812] A 801 The ring is the ring shown in equation (82) that is fused at any position of adjacent rings.

[1813] A 802 The ring is a ring of equation (83) fused at any position between adjacent rings. Two bonding sites * and A 803 Bonding at any position on the ring.

[1814] X 801 and X 802 Each independently is C(R) 803 (R) 804 ), Si(R) 805 (R) 806 ), oxygen atoms, or sulfur atoms.

[1815] A 803 The ring is an aromatic hydrocarbon ring with 6 to 50 substituted or unsubstituted carbon atoms, or a heterocycle with 5 to 50 substituted or unsubstituted carbon atoms.

[1816] Ar 801 It is an aryl group with 6 to 50 cyclic carbon atoms, substituted or unsubstituted, or a monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1817] R 801 ~R 806 Each independently

[1818] hydrogen atom,

[1819] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[1820] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[1821] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[1822] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1823] -Si(R 901 (R) 902 (R) 903 ),

[1824] -O-(R 904 ),

[1825] -S-(R 905 ),

[1826] -N(R 906 (R) 907 ),

[1827] Halogen atom, cyano group, nitro group,

[1828] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[1829] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1830] R 901 ~R 907 As defined in equation (1) above.

[1831] m801 and m802 are each independent integers from 0 to 2. When m801 is 2, R 801 They can be the same or different. When m802 is 2, R 802 They can be the same or different.

[1832] a801 is an integer from 0 to 2. When a801 is 0 or 1, the structures within the parentheses shown in "3-a801" can be the same or different. When a801 is 2, Ar 801 They can be the same or different.

[1833] In one implementation, Ar 801 It is an aryl group with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted.

[1834] In one implementation, ring A 803 A cyclic aromatic hydrocarbon ring with 6 to 50 carbon atoms, whether substituted or unsubstituted, such as a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring.

[1835] In one implementation, R 803 and R 804 Each is an alkyl group, with 1 to 50 carbon atoms, whether substituted or unsubstituted.

[1836] In one implementation, a801 is 1.

[1837] As a compound represented by formula (81), for example, the following compounds can be listed as specific examples.

[1838] [Chemistry 176]

[1839]

[1840] Specific examples of the above-mentioned groups are described in the [Definitions] section of this specification.

[1841] As described above, one aspect of the organic EL element of the present invention has a cathode, an anode, and a light-emitting layer between the cathode and the anode. In addition to comprising a first host material, a second host material, and a dopant material, the light-emitting layer may be constructed using conventionally known materials and elements, provided that the effect of the present invention is not impaired.

[1842] The content of the first and second main materials in the light-emitting layer is preferably 80% by mass or more and 99% by mass or less relative to the total content of the light-emitting layer.

[1843] The ratio (mass ratio) of the first host material to the second host material in the light-emitting layer is usually 1:99 to 99:1, preferably 10:90 to 90:10, and more preferably 40:60 to 60:40.

[1844] The content of dopant material in the light-emitting layer is preferably more than 1% by mass and less than 20% by mass relative to the total content of the light-emitting layer.

[1845] One preferred embodiment of the organic EL element of the present invention has a hole transport layer between the anode and the light-emitting layer.

[1846] One preferred embodiment of the organic EL element of the present invention has an electron transport layer between the cathode and the light-emitting layer.

[1847] Examples of representative element configurations for the organic EL element of this invention include:

[1848] (1) Anode / Light-emitting layer / Cathode

[1849] (2) Anode / hole injection layer / light-emitting layer / cathode

[1850] (3) Anode / Light-emitting layer / Electron injection and transport layer / Cathode

[1851] (4) Anode / hole injection layer / light-emitting layer / electron injection and transport layer / cathode

[1852] (5) Anode / Organic Semiconductor Layer / Light Emitting Layer / Cathode

[1853] (6) Anode / Organic semiconductor layer / Electron barrier layer / Light-emitting layer / Cathode

[1854] (7) Anode / Organic Semiconductor Layer / Light Emitting Layer / Adhesion Improvement Layer / Cathode

[1855] (8) Anode / Hole injection·Transport layer / Light-emitting layer / Electron injection·Transport layer / Cathode

[1856] (9) Anode / Insulating layer / Light-emitting layer / Insulating layer / Cathode

[1857] (10) Anode / Inorganic semiconductor layer / Insulating layer / Light-emitting layer / Insulating layer / Cathode

[1858] (11) Anode / Organic Semiconductor Layer / Insulating Layer / Light Emitting Layer / Insulating Layer / Cathode

[1859] (12) Anode / Insulating layer / Hole injection·Transport layer / Light-emitting layer / Insulating layer / Cathode

[1860] (13) Anode / Insulating layer / Hole injection·Transport layer / Light-emitting layer / Electron injection·Transport layer / Cathode

[1861] Structures such as...

[1862] The configuration described in (8) above is preferred, but not limited to them.

[1863] In this specification, "hole injection and transport layer" refers to "at least one of hole injection layer and hole transport layer", and "electron injection and transport layer" refers to "at least one of electron injection layer and electron transport layer".

[1864] Hereinafter, components that can be used in an organic EL element according to one aspect of the present invention, and materials other than the compounds constituting each layer, will be described.

[1865] (Substrate)

[1866] The substrate can be used as a support for the light-emitting element. Materials such as glass, quartz, and plastic can be used as substrates. Flexible substrates can also be used. A flexible substrate is a substrate that can be bent (flexible), and examples include plastic substrates containing polycarbonate or polyvinyl chloride.

[1867] (anode)

[1868] The anode formed on the substrate preferably uses a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically 4.0 eV or higher). Specifically, examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), or nitrides of metallic materials (e.g., titanium nitride).

[1869] (hole injection layer)

[1870] A hole injection layer is a layer containing a substance with high hole injection capability. Substances 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, manganese oxide, aromatic amine compounds, or polymers (oligomers, dendritic polymers, polymers, etc.).

[1871] (Hole transport layer)

[1872] A hole transport layer is a layer containing substances with high hole transport properties. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used in the hole transport layer. Polymer compounds such as poly(N-vinylcarbazole) (PVK) and poly(4-vinyltriphenylamine) (PVTPA) can also be used. Among these, any compound with higher hole transport properties than electron transport properties can be used. Furthermore, the layer containing the high hole transport properties can be a single layer or a layer consisting of two or more layers stacked together from the aforementioned substances.

[1873] (Guest (dopant) material of the light-emitting layer)

[1874] The luminescent layer is a layer containing a highly luminescent material, and various materials other than those used in the present invention as described above can be used. For example, as a highly luminescent material, a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used. A fluorescent compound is a compound that emits light from a singlet excited state, and a phosphorescent compound is a compound that emits light from a triplet excited state.

[1875] As blue fluorescent luminescent materials that can be used in the luminescent layer, pyrene derivatives, styrene amine derivatives, etc., can be used. Derivatives, such as fluoranthene derivatives, fluorene derivatives, diamine derivatives, and triarylamine derivatives, are used. Aromatic amine derivatives can be used as green fluorescent materials for the luminescent layer. Tetraphenyl derivatives and diamine derivatives can be used as red fluorescent materials for the luminescent layer.

[1876] For blue phosphorescent materials that can be used in the emitting layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes can be used. For green phosphorescent materials that can be used in the emitting layer, iridium complexes can be used. For red phosphorescent materials that can be used in the emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes can be used.

[1877] (Main material of the light-emitting layer)

[1878] As the luminescent layer, it can be a structure in which the aforementioned highly luminescent substance (guest material) is dispersed in other substances (host material). As the substance used to disperse the highly luminescent substance, various substances other than those used in the present invention described above can be used, and it is preferable to use a substance with a higher lowest empty orbital level (LUMO level) and a lower highest occupied orbital level (HOMO level) compared to the highly luminescent substance.

[1879] As a substrate material for dispersing highly luminescent substances, the following can be 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... 3) Derivatives and other fused aromatic compounds, triarylamine derivatives, or fused polycyclic aromatic amine derivatives and other aromatic amine compounds.

[1880] (Electron transport layer)

[1881] The electron transport layer is a layer containing substances with high electron transport properties. Electron transport layers can use 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) polymeric compounds.

[1882] (Electron injection layer)

[1883] The electron-injection layer is a layer containing materials with high electron-injection potential. Metal complexes such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and 8-hydroxyquinoline-lithium (Liq), as well as lithium oxides (LiO), can be used in the electron-injection layer. x Alkali metals, alkaline earth metals, or their compounds, etc.

[1884] (cathode)

[1885] The cathode preferably uses metals, alloys, conductive compounds, and mixtures thereof with a low work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them.

[1886] In one embodiment of the organic EL element of the present invention, the method for forming each layer is not particularly limited. Conventionally known formation methods based on vacuum evaporation, spin coating, etc., can be used. Each layer, such as the light-emitting layer, can be formed using known methods based on vacuum evaporation, molecular beam evaporation (MBE) or coating methods such as immersion in a solution dissolved in a solvent, spin coating, casting, rod coating, roll coating, etc.

[1887] In one embodiment of the organic EL element of the present invention, the film thickness of each layer is not particularly limited. Generally, in order to suppress defects such as pinholes, suppress the applied voltage to a low level, and improve the luminous efficiency, the thickness is usually preferred to be in the range of several nm to 1 μm.

[1888] [Composition]

[1889] The composition in one aspect of the present invention comprises the compound shown in formula (1) and the compound shown in formula (2) above, wherein one or more of the compounds shown in formula (1) and formula (2) contain at least one deuterium atom. Details of each material are as described above.

[1890] The form of the composition in one embodiment of the present invention is not particularly limited; for example, solids, powders, solutions, and films may be included. When it is a solid, it may be formed into granules.

[1891] The proportions of the compounds shown in formula (1) and (2) are not particularly limited. The proportions of the materials can be appropriately determined based on the desired effect of the composition.

[1892] Here, the term "film" refers to a film formed containing raw materials, which include compounds represented by formula (1) and formula (2). For example, a light-emitting layer comprising a first host material, a second host material, and a dopant material in an organic electroluminescent element according to one aspect of the present invention can be cited as an example.

[1893] The mixing ratio (mass ratio) of the compound shown in formula (1) and the compound shown in formula (2) is usually 1:99 to 99:1, preferably 10:90 to 90:10, and more preferably 40:60 to 60:40.

[1894] In one embodiment, the aforementioned composition is a powder formed from a composition comprising the compound represented by formula (1) and the compound represented by formula (2).

[1895] In one embodiment of the present invention, the composition may be in powder form. The powder may contain a compound of formula (1) and a compound of formula (2) in a single particle, or it may be a mixture of particles containing the compound of formula (1) and particles containing the compound of formula (2). The proportions of the compound of formula (1) and the compound of formula (2) are not particularly limited, as described above for the composition. This powder is sometimes also referred to as a premix.

[1896] In one embodiment of the present invention, the composition may contain components other than the compounds shown in formula (1) and formula (2) above. Other components may include the dopant materials described above. Details of the dopant materials are as described above.

[1897] [Electronic Devices]

[1898] An electronic device according to one aspect of the present invention is characterized by having an organic EL element according to one aspect of the present invention.

[1899] Specific examples of electronic devices include display components such as organic EL panel modules, display devices such as televisions, mobile phones, or personal computers, and light-emitting devices such as lighting or vehicle lamps.

[1900] Example

[1901] The following describes embodiments of the present invention. The present invention is not limited to these embodiments in any way.

[1902] <Compound>

[1903] The compounds (first host materials) represented by formula (1) used in the examples and comparative examples are shown below.

[1904] [Chemistry 177]

[1905]

[1906] The compounds (second main materials) represented by formula (2) used in the examples and comparative examples are shown below.

[1907] [Chemistry 178]

[1908]

[1909] The dopant materials used in the examples and comparative examples are shown below.

[1910] [Chemistry 179]

[1911]

[1912] Other compounds used in the examples and comparative examples are shown below.

[1913] [Chemistry 180]

[1914]

[1915] Example 1

[1916] <Fabrication of Organic EL Components>

[1917] A glass substrate (manufactured by Geomatics Co., Ltd.) with an ITO transparent electrode (anode) and a thickness of 25mm×75mm×1.1mm was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was 130nm.

[1918] The washed glass substrate with transparent electrodes is mounted on the substrate holder of the vacuum evaporation apparatus. First, compound HI-1 and compound HT-1 are co-deposited on the surface with transparent electrodes to cover the transparent electrodes, so that the proportion of compound HI-1 reaches 3 by mass, forming a hole injection layer with a film thickness of 10 nm.

[1919] Next, compound HT-1 was deposited on the hole injection layer to form an HT-1 film with a thickness of 75 nm. This HT-1 film functions as a hole transport layer (the first hole transport layer).

[1920] Compound HT-2 was further deposited on the HT-1 film to form an HT-2 film with a thickness of 15 nm. This HT-2 film functions as an electron blocking layer (second hole transport layer).

[1921] Compounds BH-1 (first host material), BH-2 (second host material), and BD-1 (dopant material) were co-deposited onto an HT-2 film to form a 20 nm thick BH:BD-1 film. This BH:BD-1 film functions as the light-emitting layer. The BH-1 and BH-2 components in the light-emitting layer are in a 1:1 mass ratio, and the concentration of BD-1 relative to the total mass of the light-emitting layer is 2%.

[1922] Compound ET-1 was deposited on the luminescent layer to form an ET-1 film with a thickness of 3 nm. This ET-1 film functions as a hole barrier layer (the first electron transport layer).

[1923] The compound ET-2 and lithium (8-hydroxyquinoline) (hereinafter also referred to as Liq) were co-deposited, with Liq accounting for 33% by mass, to form an ET-2:Liq film with a thickness of 30 nm. This ET-2:Liq film functions as an electron transport layer (the second electron transport layer). LiF and Yb were co-deposited on the ET-2 film, with Yb accounting for 50%, to form a LiF:Yb film with a thickness of 1 nm. Metallic Al was then deposited on the LiF:Yb film to form a metal cathode with a thickness of 50 nm, thus fabricating an organic EL device.

[1924] The component configuration of the organic EL element in Example 1 is shown in simplified form as follows.

[1925] ITO (130) / HT-1: HI-1 (10: 3%) / HT-1 (75) / HT-2 (15) / BH: BD-1 (20; 2%) / ET-1 (3) / ET-2: Liq (30: 33%) / LiF: Yb (1: 50%) / Al (50)

[1926] The number in parentheses indicates the film thickness (unit: nm).

[1927] <Evaluation of Organic EL Components>

[1928] At room temperature, with a constant DC current of 10mA / cm 2 The initial characteristics of the organic EL element obtained under driving conditions were measured.

[1929] With a current density of 10 mA / cm 2 A voltage was applied to the obtained organic EL element, and the EL emission spectrum was measured using a CS-1000 spectroradiometer (manufactured by Conicaminodesk Ltd.). The external quantum efficiency (EQE (unit: %)) was calculated from the obtained spectroradiometer.

[1930] With a current density of 50 mA / cm 2 A voltage was applied to the obtained organic EL element, and the time it took for the brightness to reach 95% of the initial brightness was measured (LT95 (unit: hour)).

[1931] The evaluation results are shown in Table 1. Regarding the difference between the voltage representation and Comparative Example 1, EQE and LT95 are relative values ​​with the results of Comparative Example 1 as 100%.

[1932] Comparative Examples 1-4

[1933] The compounds described in Table 1 were used as the main material for the light-emitting layer. Otherwise, organic EL elements were fabricated using the same method as in Example 1, and their performance was evaluated. The results are shown in Table 14.

[1934] [Table 14]

[1935]

[1936] Example 2-1

[1937] In Example 1, a composition was prepared by premixing compound BH1-2 (first host material) and compound BH2-2 (second host material) (premix), and then the composition and dopant material (BD-1) were co-deposited to form a light-emitting layer. Otherwise, an organic EL element was fabricated in the same manner as in Example 1 and evaluated.

[1938] The results are shown in Table 15. Regarding the difference between the voltage representation and Comparative Example 5, EQE and LT95 are relative values ​​with the results of Comparative Example 5 as 100%.

[1939] Two materials (a first host material and a second host material) can be stably vapor-deposited using a single vapor deposition source to obtain the desired component performance.

[1940] Comparative Example 5

[1941] Only compound BH1-2 was used as the host material for the light-emitting layer. Otherwise, organic EL elements were fabricated using the same method as in Example 1, and the results were evaluated. The results are shown in Table 15.

[1942] Examples 2-2 and 2-3

[1943] The compounds described in Table 15 were used as the main material for the light-emitting layer. Organic EL elements were fabricated using the same method (premix) as in Examples 2-1, and evaluated. The results are shown in Table 15. Voltage values ​​represent the difference from Comparative Example 5, and EQE and LT95 represent relative values ​​with the results of Comparative Example 5 as 100%.

[1944] [Table 15]

[1945]

[1946] Examples 3-1 and 3-2

[1947] The compounds described in Table 3 were used as the main material for the light-emitting layer. Organic EL elements were fabricated using the same method (premix) as in Examples 2-1, and evaluated. The results are shown in Table 16. Voltage values ​​represent the difference from the voltage of Comparative Example 1, and EQE and LT95 represent relative values ​​with the results of Comparative Example 1 as 100%.

[1948] [Table 16]

[1949]

[1950] The foregoing has described several embodiments and / or examples of the present invention in detail. Those skilled in the art can readily make further modifications to these illustrated embodiments and / or examples without substantially departing from the novel teachings and effects of the present invention. Therefore, these further modifications are also included within the scope of the present invention.

[1951] All documents contained herein and the contents of the application which form the basis of the priority claim under the Paris Convention upon which this application is based are hereby incorporated.

Claims

1. Organic electroluminescent devices, which have a cathode, anode, and At least one light-emitting layer disposed between the aforementioned cathode and the aforementioned anode, The aforementioned light-emitting layer comprises a first host material, a second host material, and a dopant material. The aforementioned first main material is a compound represented by the following formula (1). The aforementioned second main material is a compound represented by the following formula (2). One or more of the compounds shown in formula (1) and formula (2) have at least one deuterium atom. R in the aforementioned equation (1) 1A ~R 8A At least one of them is a deuterium atom, or R in the aforementioned formula (2). 1B ~R 8B At least one of them is a deuterium atom. [Chemistry 1] In equation (1), R 1A ~R 8A Each independently hydrogen atom, Substituent R, or The group represented by the following formula (1A), The aforementioned substituent R is Aryl groups with 6 to 18 cyclic carbon atoms, substituted or unsubstituted. When there are two or more substituents R, the two or more substituents R can be the same or different. L 1A Each independently single key, or Substituted or unsubstituted arylene groups with 6 to 14 cyclic carbon atoms Ar 1A Each independently Aryl groups with 6 to 18 cyclic carbon atoms, substituted or unsubstituted. -L 1A -Ar 1A (1A) In equation (1A), L 1A and Ar 1A As defined in equation (1) above, When there are two or more groups represented by the aforementioned formula (1A), the two or more groups represented by the aforementioned formula (1A) may be the same or different; [Chemistry 2] In equation (2), R 1B ~R 8B Each independently hydrogen atom, or Aryl groups with 6 to 18 cyclic carbon atoms, substituted or unsubstituted. X 11B It consists of oxygen or sulfur atoms. R 11B ~R 18B One of them is related to L. 2B Bonded single bonds, Not with L 2B bonded single bond R 11B ~R 18B Two or more adjacent rings bonded together to form substituted or unsubstituted saturated or unsaturated rings, or not substituted or unsubstituted saturated or unsaturated rings. Not with L 2B R consists of bonded single bonds and does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 11B ~R 18B Each independently hydrogen atom, or Aryl groups with 6 to 18 cyclic carbon atoms, substituted or unsubstituted. L 1B and L 2B Each independently single key, or Substituted or unsubstituted arylene groups with 6 to 14 cyclic carbon atoms Ar 1B for Substituted or unsubstituted aryl groups with 6 to 18 cyclic carbon atoms, or Monovalent heterocyclic groups with 5 to 18 cyclic atoms, substituted or unsubstituted. When substituents are present, each substituent is independently... Unsubstituted alkyl groups with 1 to 20 carbon atoms Unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, or Unsubstituted aryl groups with 6 to 30 cyclic carbon atoms.

2. The organic electroluminescent element according to claim 1, wherein, In the aforementioned equation (2), it is not related to L. 2B bonded single bond R 11B ~R 18B Two or more adjacent rings in a group do not form substituted or unsubstituted saturated or unsaturated rings.

3. The organic electroluminescent element according to claim 1 or 2, wherein, The compound represented by formula (2) above is any one of the compounds represented by formulas (2-1) to (2-3) below. [Chemistry 3] In equations (2-1) to (2-3), R 1B ~R 8B L 1B L 2B Ar 1B and X 11B As defined in equation (2) above, R 25B ~R 28B Two or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings. R 21B ~R 24B Two or more adjacent rings bonded together to form substituted or unsubstituted saturated or unsaturated rings, or not substituted or unsubstituted saturated or unsaturated rings. R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 21B ~R 28B Each independently hydrogen atom, or Aryl groups with 6 to 18 cyclic carbon atoms, substituted or unsubstituted.

4. The organic electroluminescent element according to claim 1 or 2, wherein, In the aforementioned equation (2), L 1B and L 2B Each is independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

5. The organic electroluminescent element according to claim 1 or 2, wherein, In the aforementioned equation (2), Ar 1B It is an aryl group with 6 to 18 cyclic carbon atoms, either substituted or unsubstituted.

6. The organic electroluminescent element according to claim 1 or 2, wherein, In the aforementioned equation (2), Ar 1B The groups are selected from those shown in formulas (a1) to (a4) below. [Chemistry 4] In equations (a1) to (a4), * represents the symbol with respect to L. 1B Bonded single bonds, R 21 for Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted. Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 )(R 902 )(R 903 )、 -O-(R 904 )、 -S-(R 905 )、 -N(R 906 )(R 907 )、 Halogen atom, cyano group, nitro group, Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or Monovalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. R 901 ~R 907 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or Monovalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. R 901 ~R 907 When there are more than two, more than two R 901 ~R 907 They can be the same or different. m1 is an integer between 0 and 4. m2 is an integer between 0 and 5. m3 is an integer between 0 and 7. When m1~m3 are each 2 or more, multiple R 21 They can be the same or different. When m1~m3 are each 2 or more, multiple adjacent R 21 They bond together to form substituted or unsubstituted saturated or unsaturated rings, or they do not form substituted or unsubstituted saturated or unsaturated rings.

7. The organic electroluminescent element according to claim 1 or 2, wherein, In the aforementioned equation (2), X 11B It is an oxygen atom.

8. The organic electroluminescent element according to claim 1 or 2, wherein, The compound represented by formula (2) is any one of the compounds represented by formulas (2-11) to (2-14) below. [Chemistry 5] In equations (2-11) to (2-14), Ar 1B As defined in equation (2) above, R 25B ~R 28B Two or more adjacent rings bond together to form substituted or unsubstituted saturated or unsaturated rings. R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 25B ~R 28B Each independently hydrogen atom, or Aryl groups with 6 to 18 cyclic carbon atoms, substituted or unsubstituted.

9. The organic electroluminescent element according to claim 1 or 2, wherein, The compound represented by formula (1) above is the compound represented by formula (1-1) below. [Chemistry 6] In equation (1-1), R 1A R 3A ~R 8A L 1A and Ar 1A As defined in equation (1) above.

10. The organic electroluminescent element according to claim 1 or 2, wherein, The compound represented by formula (1) is a compound represented by formula (1-11), formula (1-12), or formula (1-13) below. [Chemistry 7] In equations (1-11), (1-12), and (1-13), R 1A R 3A ~R 8A L 1A and Ar 1A As defined in equation (1) above.

11. The organic electroluminescent element according to claim 1 or 2, wherein, The compound represented by formula (1) above is the same as the compound represented by formula (1-2) below. [Chemistry 8] In equation (1-2), L 1A and Ar 1A As defined in equation (1) above.

12. The organic electroluminescent element according to claim 1 or 2, wherein, The compound represented by formula (1) is a compound represented by formula (1-21), formula (1-22), or formula (1-23) below. [Chemistry 9] In equations (1-21), (1-22), and (1-23), L 1A and Ar 1A As defined in equation (1) above.

13. The organic electroluminescent element according to claim 1 or 2, wherein, In the aforementioned equation (1), L 1A It is a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

14. The organic electroluminescent element according to claim 1 or 2, wherein, In the aforementioned equation (1), Ar 1A The groups are selected from those shown in formulas (a1) to (a4) below. [Chemistry 10] In equations (a1) to (a4), * represents the symbol with respect to L. 1A Bonded single bonds, R 21 for Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted. Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 )(R 902 )(R 903 )、 -O-(R 904 )、 -S-(R 905 )、 -N(R 906 )(R 907 )、 Halogen atom, cyano group, nitro group, Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or Monovalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. R 901 ~R 907 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or Monovalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. R 901 ~R 907 When there are more than two, more than two R 901 ~R 907 They can be the same or different. m1 is an integer between 0 and 4. m2 is an integer between 0 and 5. m3 is an integer between 0 and 7. When m1~m3 are each 2 or more, multiple R 21 They can be the same or different. When m1~m3 are each 2 or more, multiple adjacent R 21 They bond together to form substituted or unsubstituted saturated or unsaturated rings, or they do not form substituted or unsubstituted saturated or unsaturated rings.

15. The organic electroluminescent element according to claim 1 or 2, wherein, R in the aforementioned equation (1) 1A ~R 8A And R in the aforementioned equation (2) 1B ~R 8B At least two of them are deuterium atoms.

16. The organic electroluminescent element according to claim 1 or 2, wherein, R in the aforementioned equation (1) 1A ~R 8A And R in the aforementioned equation (2) 1B ~R 8B All of them are deuterium atoms.

17. The organic electroluminescent element according to claim 1 or 2, wherein, The compound shown in formula (1) contains at least one deuterium atom.

18. The organic electroluminescent element according to claim 1 or 2, wherein, In the aforementioned equation (1), R 1A ~R 8A At least one of them is a deuterium atom.

19. The organic electroluminescent element according to claim 1 or 2, wherein, The compound shown in formula (2) above contains at least one deuterium atom.

20. The organic electroluminescent element according to claim 1 or 2, wherein, In the aforementioned equation (2), R 1B ~R 8B At least one of them is a deuterium atom.

21. The organic electroluminescent element according to claim 1 or 2, wherein, The aforementioned dopant material comprises a compound represented by the following formula (31). [Chemistry 11] In equation (31), R 301 ~R 307 and R 311 ~R 317 Two or more adjacent rings in a group form substituted or unsubstituted saturated or unsaturated rings, or do not form substituted or unsubstituted saturated or unsaturated rings. R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 301 ~R 307 and R 311 ~R 317 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted. Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 )(R 902 )(R 903 )、 -O-(R 904 )、 -S-(R 905 )、 -N(R 906 )(R 907 )、 Halogen atom, cyano group, nitro group, Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or Monovalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. R 321 and R 322 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted. Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 )(R 902 )(R 903 )、 -O-(R 904 )、 -S-(R 905 )、 -N(R 906 )(R 907 )、 Halogen atom, cyano group, nitro group, Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or Monovalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. R 901 ~R 907 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or Monovalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. R 901 ~R 907 When there are more than two, more than two R 901 ~R 907 They can be the same or different.

22. The organic electroluminescent element according to claim 21, wherein, In the aforementioned equation (31), R 301 ~R 307 and R 311 ~R 317 At least one of them is -N(R) 906 (R) 907 The group shown is ).

23. The organic electroluminescent element according to claim 21, wherein, In the aforementioned equation (31), R 301 ~R 307 and R 311 ~R 317 At least two of them are -N(R) 906 (R) 907 The group shown is ).

24. The organic electroluminescent element according to claim 21, wherein, The compound represented by formula (31) is selected from one or more compounds of formulas (32), (34-2), and (35-2) below. [Chemistry 12] In equation (32), R 331 ~R 334 and R 341 ~R 344 Two or more adjacent rings in a group form substituted or unsubstituted saturated or unsaturated rings, or do not form substituted or unsubstituted saturated or unsaturated rings. R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 331 ~R 334 R 341 ~R 344 and R 351 and R 352 Each independently hydrogen atom, Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or Monovalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. R 361 ~R 364 Each independently Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or Monovalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In equations (34-2) and (35-2), R 361 ~R 364 As defined in equation (32) above, R 375 ~R 377 and R 384 ~R 386 Two or more adjacent rings in a group form substituted or unsubstituted saturated or unsaturated rings, or do not form substituted or unsubstituted saturated or unsaturated rings. R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 375 ~R 377 and R 384 ~R 386 and R 387 Each independently hydrogen atom, Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

25. The organic electroluminescent element according to claim 21, wherein, The compound represented by formula (31) is selected from one or more of the following formulas (32-11), (34-11), and (35-11). [Chemistry 13] In equations (32-11), (34-11), and (35-11), R 3301 ~R 3307 and R 3311 ~R 3317 Two or more adjacent rings in a group form substituted or unsubstituted saturated or unsaturated rings, or do not form substituted or unsubstituted saturated or unsaturated rings. R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 3301 ~R 3307 and R 3311 ~R 3317 and R 3331 Each is independently a hydrogen atom, an aryl group with 6-20 substituted or unsubstituted cyclic carbon atoms, or a monovalent heterocyclic group with 5-20 substituted or unsubstituted cyclic atoms, with 2 R atoms. 3331 They can be the same or different. R 3321 ~R 3324 Each is independently an aryl group with 6 to 20 cyclic carbon atoms (substituted or unsubstituted) or a monovalent heterocyclic group with 5 to 20 cyclic carbon atoms (substituted or unsubstituted).

26. The organic electroluminescent element according to claim 1 or 2, wherein, The aforementioned first main material and the aforementioned second main material are contained in a single light-emitting layer.

27. The organic electroluminescent element according to claim 1 or 2, wherein, A hole transport layer is present between the aforementioned anode and the aforementioned light-emitting layer.

28. The organic electroluminescent element according to claim 1 or 2, wherein, An electron transport layer is present between the aforementioned cathode and the aforementioned light-emitting layer.

29. A composition comprising a compound of formula (1) and a compound of formula (2), wherein one or more of the compounds of formula (1) and formula (2) contain at least one deuterium atom. R in the aforementioned equation (1) 1A ~R 8A At least one of them is a deuterium atom, or R in the aforementioned formula (2). 1B ~R 8B At least one of them is a deuterium atom. [Chemistry 14] In equation (1), R 1A ~R 8A Each independently hydrogen atom, Substituent R, or The group represented by the following formula (1A), The aforementioned substituent R is Aryl groups with 6 to 18 cyclic carbon atoms, substituted or unsubstituted. When there are two or more substituents R, the two or more substituents R can be the same or different. L 1A Each independently single key, or Substituted or unsubstituted arylene groups with 6 to 14 cyclic carbon atoms Ar 1A Each independently Aryl groups with 6 to 18 cyclic carbon atoms, substituted or unsubstituted. -L 1A -Ar 1A (1A) In equation (1A), L 1A and Ar 1A As defined in equation (1) above, When there are two or more groups represented by the aforementioned formula (1A), the two or more groups represented by the aforementioned formula (1A) may be the same or different; [Chemistry 15] In equation (2), R 1B ~R 8B Each independently hydrogen atom, or Aryl groups with 6 to 18 cyclic carbon atoms, substituted or unsubstituted. X 11B It consists of oxygen or sulfur atoms. R 11B ~R 18B One of them is related to L. 2B Bonded single bonds, Not with L 2B bonded single bond R 11B ~R 18B Two or more adjacent rings bonded together to form substituted or unsubstituted saturated or unsaturated rings, or not substituted or unsubstituted saturated or unsaturated rings. Not with L 2B R consists of bonded single bonds and does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 11B ~R 18B Each independently is a hydrogen atom, or Aryl groups with 6 to 18 cyclic carbon atoms, substituted or unsubstituted. L 1B and L 2B Each independently single key, or Substituted or unsubstituted arylene groups with 6 to 14 cyclic carbon atoms Ar 1B for Substituted or unsubstituted aryl groups with 6 to 18 cyclic carbon atoms, or Monovalent heterocyclic groups with 5 to 18 cyclic atoms, substituted or unsubstituted. When substituents are present, each substituent is independently... Unsubstituted alkyl groups with 1 to 20 carbon atoms Unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, or Unsubstituted aryl groups with 6 to 30 cyclic carbon atoms.

30. Organic electroluminescent devices, which have a cathode, anode, and At least one light-emitting layer disposed between the aforementioned cathode and the aforementioned anode, The aforementioned light-emitting layer comprises the composition of claim 29.

31. An electronic device comprising an organic electroluminescent element according to any one of claims 1 to 28 and 30.

Images