Organic electroluminescent element and electronic apparatus
By integrating low refractive index organic layers between light-emitting units in tandem-type organic electroluminescent elements, the light extraction efficiency is enhanced, thereby improving external quantum efficiency.
Patent Information
- Application Number
- JP2023221823
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2023-12-27
- Publication Date
- 2025-07-09
AI Technical Summary
Tandem-type organic electroluminescent elements face challenges in improving external quantum efficiency due to low light extraction efficiency, primarily attributed to differences in refractive indices of adjacent layers.
Incorporating low refractive index layers made of organic materials with a refractive index of 1.87 or less between light-emitting units, with specific thickness and composition requirements to enhance light extraction efficiency.
The solution significantly improves external quantum efficiency by optimizing light extraction, enhancing the performance of tandem-type organic electroluminescent elements.
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Figure 2025104004000001_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to an organic electroluminescent element and an electronic device.
Background Art
[0002] Organic electroluminescent elements (hereinafter sometimes referred to as "organic EL elements") are applied to full-color displays such as mobile phones and televisions. When a voltage is applied to an organic EL element, holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. At this time, according to the statistical law of electron spin, singlet excitons are generated at a rate of 25%, and triplet excitons are generated at a rate of 75%. Examples of the performance of organic EL elements include luminance, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan. One of the problems of organic EL elements is low light extraction efficiency. In particular, attenuation due to reflection caused by differences in refractive indices of adjacent layers is a major factor in reducing the light extraction efficiency of organic EL elements. In order to reduce this influence, a configuration of an organic EL element having a layer made of a low refractive index material has been proposed.
[0003] For example, in Patent Document 1, studies have been made to improve the performance of organic EL elements. Patent Document 1 describes that by using a layer made of a low refractive index material as an organic layer (for example, a hole transport layer) in the hole transport region, light emission loss due to the evanescent mode can be reduced. Further, Patent Document 1 describes that by arranging an organic layer made of a high refractive index material on the anode side and an organic layer made of a low refractive index material on the light-emitting layer side as an organic layer (for example, a hole transport layer) in the hole transport region, light emission loss in the thin film mode can be reduced.
Prior Art Documents
Patent Documents
[0004]
Patent Document 1
Summary of the Invention
Problems to be Solved by the Invention
[0005] As one aspect of an organic EL element, a tandem-type organic EL element in which a plurality of light-emitting units are stacked is known. For example, Patent Document 1 also describes a tandem-type organic EL element. Further improvement in the performance of the tandem-type organic EL element (for example, improvement in external quantum efficiency) is required.
[0006] An object of the present invention is to provide a tandem-type organic electroluminescence element capable of improving external quantum efficiency, and an electronic device equipped with the organic electroluminescence element.
Means for Solving the Problems
[0007] According to one aspect of the present invention, there is provided an organic electroluminescence element, The organic electroluminescence element includes an anode, a cathode, and two or more light-emitting units disposed between the anode and the cathode, The two or more light-emitting units include at least a first light-emitting unit and a second light-emitting unit, The first light-emitting unit and the second light-emitting unit are arranged in this order from the anode side to the cathode side, The first light-emitting unit includes a first light-emitting band, The second light-emitting unit includes a second light-emitting band, One or more low refractive index layers are disposed between the first light-emitting band and the second light-emitting band, Each of the one or more low refractive index layers independently contains an organic material having a refractive index of 1.87 or less, The following condition (TDM1) or (TDM2) is satisfied, An organic electroluminescence element is provided. (Condition (TDM1): Two or more of the low refractive index layers are arranged between the first emission band and the second emission band, at least two of the low refractive index layers are in direct contact, and the sum of the film thicknesses of each of the at least two directly contacting low refractive index layers is 50 nm or more, and at least one of the at least two directly contacting low refractive index layers contains the organic material and at least one selected from the group consisting of metals and metal compounds.) Condition (TDM2): At least one low refractive index layer having a film thickness of 50 nm or more is arranged between the first emission band and the second emission band, and the low refractive index layer having a film thickness of 50 nm or more contains the organic material and at least one selected from the group consisting of metals and metal compounds.)
[0008] According to one aspect of the present invention, there is provided an electronic device equipped with an organic electroluminescence element according to one aspect of the present invention.)
Effects of the Invention
[0009] According to one aspect of the present invention, it is possible to provide an organic electroluminescence element capable of improving the external quantum efficiency. According to one aspect of the present invention, it is possible to provide an electronic device equipped with the organic electroluminescence element.)
Brief Description of the Drawings
[0010]
Figure 1
Figure 2
Modes for Carrying Out the Invention
[0011] [Definitions] In this specification, the hydrogen atom includes isotopes with different numbers of neutrons, namely, protium, deuterium, and tritium.
[0012] In this specification, in a chemical structural formula, at a bondable position where symbols such as "R" or "D" representing a deuterium atom are not explicitly shown, it is assumed that a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is bonded.
[0013] In this specification, the number of ring-forming carbon atoms refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are cyclically bonded (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted by a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbon atoms. The same shall apply to the "number of ring-forming carbon atoms" described below unless otherwise specified. For example, a benzene ring has 6 ring-forming carbon atoms, a naphthalene ring has 10 ring-forming carbon atoms, a pyridine ring has 5 ring-forming carbon atoms, and a furan ring has 4 ring-forming carbon atoms. Also, for example, the number of ring-forming carbon atoms of a 9,9-diphenylfluorenyl group is 13, and the number of ring-forming carbon atoms of a 9,9'-spirobifluorenyl group is 25. Also, when, for example, an alkyl group is substituted as a substituent on a benzene ring, the number of carbon atoms of the alkyl group is not included in the number of ring-forming carbon atoms of the benzene ring. Therefore, the number of ring-forming carbon atoms of a benzene ring substituted with an alkyl group is 6. Also, when, for example, an alkyl group is substituted as a substituent on a naphthalene ring, the number of carbon atoms of the alkyl group is not included in the number of ring-forming carbon atoms of the naphthalene ring. Therefore, the number of ring-forming carbon atoms of a naphthalene ring substituted with an alkyl group is 10.
[0014] In this specification, the number of ring-forming atoms refers to the number of atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, monocyclic, condensed ring, and ring assembly) (for example, monocyclic compound, condensed ring compound, crosslinked compound, carbocyclic compound, and heterocyclic compound). Atoms that do not constitute the ring (for example, hydrogen atoms that terminate the bonds of the atoms constituting the ring) and atoms contained in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. Unless otherwise specified, the "number of ring-forming atoms" described below shall be the same. For example, the number of ring-forming atoms of a pyridine ring is 6, the number of ring-forming atoms of a quinazoline ring is 10, and the number of ring-forming atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or the number of atoms constituting a substituent is not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. Further, for example, the number of hydrogen atoms bonded to a carbon atom of a quinazoline ring or the number of atoms constituting a substituent is not included in the number of quinazoline ring-forming atoms. Therefore, the number of ring-forming atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.
[0015] In this specification, in the expression "substituted or unsubstituted ZZ group having XX to YY carbon atoms", "XX to YY carbon atoms" represents the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of substituents when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.
[0016] In this specification, in the expression "substituted or unsubstituted ZZ group having XX to YY atoms", "XX to YY atoms" represents the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of substituents when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.
[0017] In this specification, an unsubstituted ZZ group represents the case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group represents the case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group". In this specification, "unsubstituted" in the case of a "substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group has not been replaced by a substituent. The hydrogen atom in an "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom. Also, in this specification, "substituted" in the case of a "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group have been replaced by a substituent. Similarly, "substituted" in the case of a "BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group have been replaced by an AA group.
[0018] "Substituents described in this specification" Hereinafter, the substituents described in this specification will be described.
[0019] Unless otherwise specified in this specification, the number of ring-forming carbon atoms of an "unsubstituted aryl group" described in this specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18. Unless otherwise specified in this specification, the number of ring-forming atoms of an "unsubstituted heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18. Unless otherwise specified in this specification, the number of carbon atoms of an "unsubstituted alkyl group" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6. Unless otherwise specified in this specification, the number of carbon atoms of an "unsubstituted alkenyl group" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6. Unless otherwise specified in this specification, the number of carbon atoms of an "unsubstituted alkynyl group" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6. The number of ring-forming carbon atoms of the "unsubstituted cycloalkyl group" described in this specification is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified in this specification. The number of ring-forming carbon atoms of the "unsubstituted arylene group" described in this specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified in this specification. The number of ring-forming atoms of the "unsubstituted divalent heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified in this specification. The number of carbon atoms of the "unsubstituted alkylene group" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified in this specification.
[0020] · "Substituted or unsubstituted aryl group" Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl groups (specific example group G1A) and substituted aryl groups (specific example group G1B), etc. (Here, the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is the "unsubstituted aryl group", and the substituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is the "substituted aryl group".) In this specification, when simply referring to an "aryl group", it includes both "unsubstituted aryl group" and "substituted aryl group". The "substituted aryl group" means a group in which one or more hydrogen atoms of the "unsubstituted aryl group" are replaced by substituents. Examples of the "substituted aryl group" include, for example, a group in which one or more hydrogen atoms of the "unsubstituted aryl group" in the following specific example group G1A are replaced by substituents, and examples of the substituted aryl groups in the following specific example group G1B. Note that the examples of the "unsubstituted aryl group" and the "substituted aryl group" listed here are only examples, and the "substituted aryl group" described in this specification includes a group in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group" in the following specific example group G1B is further replaced by a substituent, and a group in which a hydrogen atom of the substituent in the "substituted aryl group" in the following specific example group G1B is further replaced by a substituent.
[0021] ·Aryl groups without substitution (specific example group G1A): Phenyl group, p-Biphenyl group, m-Biphenyl group, o-Biphenyl group, p-Terphenyl-4-yl group, p-Terphenyl-3-yl group, p-Terphenyl-2-yl group, m-Terphenyl-4-yl group, m-Terphenyl-3-yl group, m-Terphenyl-2-yl group, o-Terphenyl-4-yl group, o-Terphenyl-3-yl group, o-Terphenyl-2-yl group, 1-Naphthyl group, 2-Naphthyl group, Anthryl group, Benzoanthryl group, Phenanthryl group, Benzophenanthryl group, Phenalenyl group, Pyrenyl group, Chrysenyl group, Benzochrysenyl group, Triphenylenyl group, Benzotriphenylenyl group, Tetracenyl group, Pentacenyl group, Fluorenyl group, 9,9'-Spirobifluorenyl group, Benzofluorenyl group, Dibenzofluorenyl group, Fluoranthenyl group, Benzofluoranthenyl group, Perylenyl group, and A monovalent aryl group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-1) to (TEMP-15).
[0022]
Chemical formula
[0023] [Chemical]
[0024] ·An aryl group for substitution (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, cyanophenyl group, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl group, and a group in which one or more hydrogen atoms of a monovalent group derived from the ring structures represented by the general formulas (TEMP-1) to (TEMP-15) are replaced with substituents.
[0025] ·"Substituted or unsubstituted heterocyclic group" The "heterocyclic group" described in this specification is a cyclic group containing at least one heteroatom in the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom. The "heterocyclic group" described in this specification is a monocyclic group or a fused-ring group. The "heterocyclic group" described in this specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic groups (specific example group G2A), substituted heterocyclic groups (specific example group G2B), and the like. (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when simply referring to the "heterocyclic group", it includes both the "unsubstituted heterocyclic group" and the "substituted heterocyclic group". The "substituted heterocyclic group" means a group in which one or more hydrogen atoms of the "unsubstituted heterocyclic group" are replaced by substituents. Specific examples of the "substituted heterocyclic group" include groups in which the hydrogen atoms of the "unsubstituted heterocyclic group" in the following specific example group G2A are replaced, and examples of the substituted heterocyclic group in the following specific example group G2B. It should be noted that the examples of the "unsubstituted heterocyclic group" and the "substituted heterocyclic group" listed here are only examples, and the "substituted heterocyclic group" described in this specification also includes groups in which the hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself in the "substituted heterocyclic group" of specific example group G2B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted heterocyclic group" of specific example group G2B are further replaced by substituents.
[0026] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).
[0027] The specific example group G2B includes, for example, a substituted heterocyclic group containing a nitrogen atom (specific example group G2B1), a substituted heterocyclic group containing an oxygen atom (specific example group G2B2), a substituted heterocyclic group containing a sulfur atom (specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) are replaced with substituents (specific example group G2B4).
[0028] · Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1): Pyrrolyl group, Imidazolyl group, Pyrazolyl group, Triazolyl group, Tetrazolyl group, Oxazolyl group, Isoxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, Thiadiazolyl group, Pyridyl group, Pyridazinyl group, Pyrimidinyl group, Pyrazinyl group, Triazinyl group, Indolyl group, Isoindolyl group, Indolizinyl group, Quinolizinyl group, Quinolyl group, Isoquinolyl group, Cinnolyl group, Phthalazinyl group, Quinazolinyl group, Quinoxalinyl group, Benzimidazolyl group, Indazolyl group, Phenanthrolinyl group, Phenanthridinyl group, Acridinyl group, Phenazinyl group, Carbazolyl group, Benzocarbazolyl group, Morpholino group, a phenoxazinyl group, a phenothiazinyl group, an azacarbazolyl group, and a diazacarbazolyl group.
[0029] · an unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): a furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a xanthenyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a benzoxazolyl group, a benzoisoxazolyl group, a phenoxazinyl group, a morpholino group, a dinaphthofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, an azanaphthobenzofuranyl group, and a diazanaphthobenzofuranyl group.
[0030] · an unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3): a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a benzothiophenyl group (benzothienyl group), an isobenzothiophenyl group (isobenzothienyl group), a dibenzothiophenyl group (dibenzothienyl group), a naphthobenzothiophenyl group (naphthobenzothienyl group), a benzothiazolyl group, a benzoisothiazolyl group, a phenothiazinyl group, a dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), Diazaazadibenzothiophenyl group (diazaazadibenzothienyl group), Azananofbenzothiophenyl group (azananofbenzothienyl group), and Diazaazananofbenzothiophenyl group (diazaazananofbenzothienyl group).
[0031] · A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):
[0032]
Chemical formula
[0033]
Chemical formula
[0034] In the general formulas (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2. However, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH. In the general formulas (TEMP-16) to (TEMP-33), when at least one of X A and Y A is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.
[0035] · A substituted heterocyclic group containing a nitrogen atom (specific example group G2B1): (9-Phenyl)carbazolyl group, (9-Biphenylyl)carbazolyl group, (9-Phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, methylbenzimidazolyl group, ethylbenzimidazolyl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenylquinazolinyl group, and biphenylylquinazolinyl group.
[0036] ·Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, t-butyldibenzofuranyl group, and monovalent residue of spiro[9H-xanthene-9,9’-[9H]fluorene].
[0037] ·Substituted heterocyclic groups containing a sulfur atom (specific example group G2B3): phenyldibenzothiophenyl group, methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, and monovalent residue of spiro[9H-thioxanthene-9,9’-[9H]fluorene].
[0038] ·A group in which one or more hydrogen atoms of the monovalent heterocyclic group derived from the ring structures represented by the general formulas (TEMP-16) to (TEMP-33) are replaced with substituents (specific example group G2B4):
[0039] The "one or more hydrogen atoms of the monovalent heterocyclic group" refers to the hydrogen atoms bonded to the ring-forming carbon atoms of the monovalent heterocyclic group, X A and Y A When at least one of them is NH, the hydrogen atoms bonded to the nitrogen atoms, and X A and Y Ameans one or more hydrogen atoms selected from the hydrogen atoms of the methylene group when one of them is CH2.
[0040] · "Substituted or unsubstituted alkyl group" Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B). (Here, the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group", and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group".) Hereinafter, when simply referred to as "alkyl group", both "unsubstituted alkyl group" and "substituted alkyl group" are included. "Substituted alkyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkyl group" are replaced by substituents. Specific examples of the "substituted alkyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl groups" (specific example group G3A) are replaced by substituents, and examples of substituted alkyl groups (specific example group G3B), etc. In this specification, the alkyl group in the "unsubstituted alkyl group" means a chain alkyl group. Therefore, the "unsubstituted alkyl group" includes a linear "unsubstituted alkyl group" and a branched "unsubstituted alkyl group". Note that the examples of the "unsubstituted alkyl group" and the examples of the "substituted alkyl group" listed here are only examples, and the "substituted alkyl group" described in this specification includes groups in which the hydrogen atoms of the alkyl group itself in the "substituted alkyl group" of specific example group G3B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted alkyl group" of specific example group G3B are further replaced by substituents.
[0041] · Unsubstituted alkyl group (specific example group G3A): Methyl group, Ethyl group, n-Propyl group, Isopropyl group, n-Butyl group, Isobutyl group, s-Butyl group, and t-butyl group.
[0042] · Substituted alkyl group (specific example group G3B): Heptafluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-Trifluoroethyl group, and Trifluoromethyl group.
[0043] · "Substituted or unsubstituted alkenyl group" Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described in this specification include the following unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (Here, the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group", and the "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group".) In this specification, when simply referring to an "alkenyl group", it includes both an "unsubstituted alkenyl group" and a "substituted alkenyl group". The "substituted alkenyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkenyl group" are replaced by substituents. Specific examples of the "substituted alkenyl group" include groups in which the following "unsubstituted alkenyl groups" (specific example group G4A) have substituents, and examples of substituted alkenyl groups (specific example group G4B), etc. Note that the examples of the "unsubstituted alkenyl group" and the "substituted alkenyl group" listed here are only examples, and the "substituted alkenyl group" described in this specification includes groups in which the hydrogen atoms of the alkenyl group itself in the "substituted alkenyl group" of specific example group G4B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted alkenyl group" of specific example group G4B are further replaced by substituents.
[0044] · Unsubstituted alkenyl group (specific example group G4A): Vinyl group, Allyl group, 1-Butenyl group, 2-Butenyl group, and 3-Butenyl group.
[0045] · Substituted alkenyl group (specific example group G4B): 1,3-Butadienyl group, 1-Methylvinyl group, 1-Methylallyl group, 1,1-Dimethylallyl group, 2-Methylallyl group, and 1,2-Dimethylallyl group.
[0046] · "Substituted or unsubstituted alkynyl group" Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in this specification include the following unsubstituted alkynyl groups (specific example group G5A), etc. (Here, the unsubstituted alkynyl group refers to the case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group"). Hereinafter, when simply referred to as "alkynyl group", it includes both "unsubstituted alkynyl group" and "substituted alkynyl group". The "substituted alkynyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" are replaced by substituents. Specific examples of the "substituted alkynyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl groups" (specific example group G5A) are replaced by substituents, etc.
[0047] · Unsubstituted alkynyl group (specific example group G5A): Ethynyl group.
[0048] · "Substituted or unsubstituted cycloalkyl group" Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described in this specification include the following unsubstituted cycloalkyl groups (specific example group G6A), substituted cycloalkyl groups (specific example group G6B), and the like. (Here, the unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group", and the substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group".) In this specification, when simply referring to the "cycloalkyl group", it includes both the "unsubstituted cycloalkyl group" and the "substituted cycloalkyl group". The "substituted cycloalkyl group" means a group in which one or more hydrogen atoms in the "unsubstituted cycloalkyl group" are replaced by substituents. Specific examples of the "substituted cycloalkyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl groups" (specific example group G6A) are replaced by substituents, and examples of substituted cycloalkyl groups (specific example group G6B). Note that the examples of the "unsubstituted cycloalkyl group" and the "substituted cycloalkyl group" listed here are merely examples, and the "substituted cycloalkyl group" described in this specification includes groups in which one or more hydrogen atoms bonded to the carbon atoms 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.
[0049] · Unsubstituted cycloalkyl groups (specific example group G6A): Cyclopropyl group, Cyclobutyl group, Cyclopentyl group, Cyclohexyl group, 1 - Adamantyl group, 2 - Adamantyl group, 1 - Norbornyl group, and 2 - Norbornyl group.
[0050] · Substituted cycloalkyl groups (specific example group G6B): 4 - Methylcyclohexyl group.
[0051] · "A group represented by -Si(R 901 )(R 902 )(R 903 )" Examples (specific example group G7) of the group represented by -Si(R 901 )(R 902 )(R 903 ) described in this specification include -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) are mentioned. Here G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. G2 is the "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is the "substituted or unsubstituted cycloalkyl group" described in specific example group G6. The plurality of G1s in -Si(G1)(G1)(G1) are the same as or different from each other. The plurality of G2s in -Si(G1)(G2)(G2) are the same as or different from each other. The plurality of G1s in -Si(G1)(G1)(G2) are the same as or different from each other. The plurality of G2s in -Si(G2)(G2)(G2) are the same as or different from each other. The plurality of G3s in -Si(G3)(G3)(G3) are the same as or different from each other. The plurality of G6s in -Si(G6)(G6)(G6) are the same as or different from each other.
[0052] · "A group represented by -O-(R 904 )" -O-(R904 ) Examples of the group represented by (specific example group G8) include -O(G1), -O(G2), -O(G3), and -O(G6) are included. Here, G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. G2 is the "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is the "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
[0053] · The group represented by "-S-(R 905 )" Examples of the group represented by -S-(R 905 ) described in this specification (specific example group G9) include -S(G1), -S(G2), -S(G3), and -S(G6) are included. Here, G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. G2 is the "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is the "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
[0054] · The group represented by "-N(R 906 )(R 907 )" Examples of the group represented by -N(R 906 )(R 907 ) described in this specification (specific example group G10) include -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) may be mentioned. Here, G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. G2 is the "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is the "substituted or unsubstituted cycloalkyl group" described in specific example group G6. The plurality of G1 in -N(G1)(G1) are the same as or different from each other. The plurality of G2 in -N(G2)(G2) are the same as or different from each other. The plurality of G3 in -N(G3)(G3) are the same as or different from each other. The plurality of G6 in -N(G6)(G6) are the same as or different from each other.
[0055] · "halogen atom" Specific examples (specific example group G11) of the "halogen atom" described in this specification include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.
[0056] · "substituted or unsubstituted fluoroalkyl group" As used herein, the term "substituted or unsubstituted fluoroalkyl group" means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced by fluorine atoms (perfluoro group). Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted fluoroalkyl group" is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18. The "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms in the "fluoroalkyl group" are replaced by substituents. In addition, the "substituted fluoroalkyl group" as described herein includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the "substituted fluoroalkyl group" are further replaced by substituents, and a group in which one or more hydrogen atoms of the substituents in the "substituted fluoroalkyl group" are further replaced by substituents. Specific examples of the "unsubstituted fluoroalkyl group" include examples of groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced by fluorine atoms.
[0057] · "substituted or unsubstituted haloalkyl group" As used herein, the term "substituted or unsubstituted haloalkyl group" means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced by halogen atoms. Unless otherwise specified herein, the number of carbon atoms in an "unsubstituted haloalkyl group" is from 1 to 50, preferably from 1 to 30, more preferably from 1 to 18. The term "substituted haloalkyl group" means a group in which one or more hydrogen atoms in a "haloalkyl group" are replaced by substituents. It should be noted that the "substituted haloalkyl group" as described herein also includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in a "substituted haloalkyl group" are further replaced by substituents, and a group in which one or more hydrogen atoms of the substituents in a "substituted haloalkyl group" are further replaced by substituents. Specific examples of the "unsubstituted haloalkyl group" include examples of groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced by halogen atoms. The haloalkyl group may be referred to as a halogenated alkyl group.
[0058] · "Substituted or unsubstituted alkoxy group" Specific examples of the "substituted or unsubstituted alkoxy group" as described herein include groups represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified herein, the number of carbon atoms in an "unsubstituted alkoxy group" is from 1 to 50, preferably from 1 to 30, more preferably from 1 to 18.
[0059] · "Substituted or unsubstituted alkylthio group" Specific examples of the "substituted or unsubstituted alkylthio group" as described herein include groups represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified herein, the number of carbon atoms in an "unsubstituted alkylthio group" is from 1 to 50, preferably from 1 to 30, more preferably from 1 to 18.
[0060] · "Substituted or unsubstituted aryloxy group" As a specific example of the "substituted or unsubstituted aryloxy group" described in this specification, it is a group represented by -O(G1), where G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1. The number of ring-forming carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
[0061] · "Substituted or unsubstituted arylthio group" As a specific example of the "substituted or unsubstituted arylthio group" described in this specification, it is a group represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1. The number of ring-forming carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
[0062] · "Substituted or unsubstituted trialkylsilyl group" As a specific example of the "trialkylsilyl group" described in this specification, it is a group represented by -Si(G3)(G3)(G3), where G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3. A plurality of G3 in -Si(G3)(G3)(G3) are the same as or different from each other. The number of carbon atoms of each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.
[0063] · "Substituted or unsubstituted aralkyl group" Specific examples of the "substituted or unsubstituted aralkyl group" described in this specification include a group represented by -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3, and G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1. Therefore, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is a form of a "substituted alkyl group". An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and the number of carbon atoms of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification. Specific examples of the "substituted or unsubstituted aralkyl group" include a benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group, etc.
[0064] The substituted or unsubstituted aryl group described in this specification is preferably a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group, pyrenyl group, chrysenyl group, triphenylenyl group, fluorenyl group, 9,9'-spirobifluorenyl group, 9,9-dimethylfluorenyl group, and 9,9-diphenylfluorenyl group, etc., unless otherwise specified in this specification.
[0065] The substituted or unsubstituted heterocyclic group described in this specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an azadibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazol-4-yl group), a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, and a phenyldibenzothiophenyl group, etc., unless otherwise described in this specification.
[0066] In this specification, unless otherwise described in this specification, the carbazolyl group is specifically any of the following groups.
[0067]
Chemical formula
[0068] In this specification, unless otherwise described in this specification, the (9-phenyl)carbazolyl group is specifically any of the following groups.
[0069]
Chemical formula
[0070] In the general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.
[0071] In this specification, unless otherwise specified herein, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups.
[0072]
Chemical formula
[0073] In the general formulas (TEMP-34) to (TEMP-41), * represents a bonding position.
[0074] Unless otherwise specified herein, the substituted or unsubstituted alkyl group described in this specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, and the like.
[0075] · "Substituted or unsubstituted arylene group" Unless otherwise specified herein, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above "substituted or unsubstituted aryl group". Specific examples (specific example group G12) of the "substituted or unsubstituted arylene group" include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1.
[0076] · "Substituted or unsubstituted divalent heterocyclic group" Unless otherwise specified herein, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom on the heterocyclic ring from the above "substituted or unsubstituted heterocyclic group". Specific examples (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group" include divalent groups derived by removing one hydrogen atom on the heterocyclic ring from the "substituted or unsubstituted heterocyclic group" described in specific example group G2.
[0077] · "Substituted or unsubstituted alkylene group" Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group". Specific examples (specific example group G14) of the "substituted or unsubstituted alkylene group" include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3, and the like.
[0078] Unless otherwise specified in this specification, the substituted or unsubstituted arylene group described in this specification is preferably a group of any of the following general formulas (TEMP-42) to (TEMP-68).
[0079]
Chemical formula
[0080]
Chemical formula
[0081] In the general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent. In the general formulas (TEMP-42) to (TEMP-52), * represents the bonding position.
[0082]
Chemical formula
[0083] In the general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent. Formula Q9 and Q 10 may be bonded to each other via a single bond to form a ring. In the general formulas (TEMP-53) to (TEMP-62), * represents the bonding position.
[0084]
Chemical formula
[0085] In the general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent. In the general formulas (TEMP-63) to (TEMP-68), * represents the bonding position.
[0086] Unless otherwise specified herein, the substituted or unsubstituted divalent heterocyclic group described herein is preferably a group of any of the following general formulas (TEMP-69) to (TEMP-102).
[0087]
Chemical formula
[0088]
Chemical formula
[0089]
Chemical formula
[0090] In the general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.
[0091]
Chemical formula
[0092]
Chemical formula
[0093] [Chemistry]
[0094] [Chemistry]
[0095] In the general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.
[0096] The above is the description of "the substituents described in this specification".
[0097] · "When bonding to form a ring" In this specification, the case of "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted monocyclic ring, or bond to each other to form a substituted or unsubstituted condensed ring, or do not bond to each other" means the case of "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted monocyclic ring", the case of "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted condensed ring", and the case of "one or more sets of two or more adjacent ones do not bond to each other". Regarding the case in this specification where "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted condensed ring" (hereinafter, these cases may be collectively referred to as "the case of bonding to form a ring"), an explanation will be given below. Taking the case of an anthracene compound represented by the following general formula (TEMP-103) whose mother skeleton is an anthracene ring as an example.
[0098] [Chemistry]
[0099] For example, R921 ~R 930 Among them, in the case of "one or more of the pairs consisting of two or more adjacent ones are combined with each other to form a ring", the pair consisting of two adjacent ones that form one pair means R 921 and R 922 and the pair of R 922 and R 923 and the pair of R 923 and R 924 and the pair of R 924 and R 930 and the pair of R 930 and R 925 and the pair of R 925 and R 926 and the pair of R 926 and R 927 and the pair of R 927 and R 928 and the pair of R 928 and R 929 and the pair of R, and R 929 and R 921 and the pair of R.
[0100] The above "one or more" means that two or more of the pairs consisting of two or more adjacent ones may form a ring at the same time. For example, R 921 and R 922 are combined with each other to form ring Q A and at the same time R 925 and R 926 are combined with each other to form ring Q B is formed, then the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).
[0101]
Chemical formula
[0102] The case where a "pair consisting of two or more adjacent ones" forms a ring includes not only the case where a pair consisting of "two" adjacent ones is combined as in the above example, but also the case where a pair consisting of "three or more" adjacent ones is combined. For example, R 921 and R 922 are combined with each other to form ring Q A and, R 922 and R923 are combined with each other to form ring Q C to form, and a group consisting of three adjacent ones (R 921 , R 922 and R 923 ) are combined with each other to form a ring and condensed to the anthracene backbone. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C share R 922 .
[0103] [Chemical formula]
[0104] The "monocyclic ring" or "condensed ring" formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when "a set of two adjacent ones" forms a "monocyclic ring" or "condensed ring", the "monocyclic ring" or "condensed ring" can form a saturated ring or an unsaturated ring. For example, ring Q A and ring Q B formed in the general formula (TEMP-104) are each a "monocyclic ring" or "condensed ring", respectively. Also, ring Q A and ring Q C formed in the general formula (TEMP-105) are "condensed rings". Ring Q A and ring Q C in the general formula (TEMP-105) are a condensed ring formed by the condensation of ring Q A and ring Q C . If ring Q A in the general formula (TMEP-104) is a benzene ring, ring Q A is a monocyclic ring. If ring Q A in the general formula (TMEP-104) is a naphthalene ring, ring Q A is a condensed ring.
[0105] "Unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. "Saturated ring" means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of the aromatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G1 are terminated by hydrogen atoms. Specific examples of the aromatic heterocyclic ring include structures in which the aromatic heterocyclic ring groups exemplified as specific examples in Specific Example Group G2 are terminated by hydrogen atoms. Specific examples of the aliphatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G6 are terminated by hydrogen atoms. "Forming a ring" means forming a ring with only a plurality of atoms of the parent skeleton or with a plurality of atoms of the parent skeleton and one or more arbitrary elements. For example, in the general formula (TEMP-104), the ring Q formed by the bonding of R 921 and R 922 means a ring formed by the carbon atoms of the anthracene skeleton to which R A is bonded, the carbon atoms of the anthracene skeleton to which R 921 is bonded, and one or more arbitrary elements. As a specific example, when forming the ring Q 922 with R 921 and R 922 , in the case where a monocyclic unsaturated ring is formed by the carbon atoms of the anthracene skeleton to which R A is bonded, the carbon atoms of the anthracene skeleton to which R 921 is bonded, and four carbon atoms, the ring formed by R 922 and R 921 is a benzene ring. 922 is a benzene ring.
[0106] Here, "arbitrary element" is preferably at least one element selected from the group consisting of a carbon element, a nitrogen element, an oxygen element, and a sulfur element, unless otherwise specified in this specification. In an arbitrary element (for example, in the case of a carbon element or a nitrogen element), a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described later. When an arbitrary element other than the carbon element is included, the formed ring is a heterocyclic ring. Unless otherwise specified in this specification, the "one or more arbitrary elements" constituting the monocyclic or condensed ring are 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. Unless otherwise specified in this specification, among the "monocyclic ring" and the "condensed ring", the "monocyclic ring" is preferred. Unless otherwise specified in this specification, among the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred. Unless otherwise specified in this specification, the "monocyclic ring" is preferably a benzene ring. Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring. When "one or more sets of two or more adjacent ones" "are bonded to each other to form a substituted or unsubstituted monocyclic ring" or "are bonded to each other to form a substituted or unsubstituted condensed ring", unless otherwise specified in this specification, preferably, one or more sets of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted "unsaturated ring" composed of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of 1 to 15 carbon, nitrogen, oxygen, and sulfur elements.
[0107] When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "arbitrary substituent" described later. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the section of "substituents described in this specification" mentioned above. When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "arbitrary substituent" described later. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the section of "substituents described in this specification" mentioned above. The above is the explanation of the case where "one or more sets of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more sets of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted condensed ring" (the case of "bonding to form a ring").
[0108] · A substituent in the case of "substituted or unsubstituted" In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (which may be referred to as "any substituent" in the present specification) is, for example, An unsubstituted alkyl group having 1 to 50 carbon atoms, An unsubstituted alkenyl group having 2 to 50 carbon atoms, An unsubstituted alkynyl group having 2 to 50 carbon atoms, An unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), A halogen atom, a cyano group, a nitro group, An unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and An unsubstituted heterocyclic group having 5 to 50 ring-forming atoms Selected from the group consisting of groups such as, Here, R 901 ~R 907 Are each independently, A hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. R 901 When two or more are present, two or more R 901 Are the same as or different from each other, R 902 When two or more are present, two or more R 902 Are the same as or different from each other, R903 When two or more Rs exist, the two or more Rs 903 are either identical to each other or different, R 904 When two or more Rs exist, the two or more Rs 904 are either identical to each other or different, R 905 When two or more Rs exist, the two or more Rs 905 are either identical to each other or different, R 906 When two or more Rs exist, the two or more Rs 906 are either identical to each other or different, R 907 When two or more Rs exist, the two or more Rs 907 are either identical to each other or different.
[0109] In one embodiment, the substituent in the case of "substituted or unsubstituted" is an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring-forming carbon atoms, and a heterocyclic group having 5 to 50 ring-forming atoms and is a group selected from the group consisting of.
[0110] In one embodiment, the substituent in the case of "substituted or unsubstituted" is an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring-forming carbon atoms, and a heterocyclic group having 5 to 18 ring-forming atoms and is a group selected from the group consisting of.
[0111] Specific examples of each group of the above-mentioned arbitrary substituents are the specific examples of the substituents described in the section of "substituents described in this specification" mentioned above.
[0112] Unless otherwise specified herein, 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, and more preferably a benzene ring. Unless otherwise specified herein, any substituent may further have a substituent. The substituent that any substituent further has is the same as the above-mentioned any substituent.
[0113] In this specification, the numerical range represented by "AA~BB" means a range including the numerical value AA described before "AA~BB" as the lower limit value and the numerical value BB described after "AA~BB" as the upper limit value.
[0114] 〔First Embodiment〕 <Organic Electroluminescence Element> The organic electroluminescence element according to this embodiment has an anode, a cathode, and two or more light-emitting units disposed between the anode and the cathode. The two or more light-emitting units include at least a first light-emitting unit and a second light-emitting unit. The first light-emitting unit and the second light-emitting unit are arranged in this order from the anode side toward the cathode side. The first light-emitting unit includes a first light-emitting band. The second light-emitting unit includes a second light-emitting band. One or more low refractive index layers are disposed between the first light-emitting band and the second light-emitting band. Each of the one or more low refractive index layers independently contains an organic material having a refractive index of 1.87 or less. The following condition (TDM1) or (TDM2) is satisfied.
[0115] (Condition (TDM1): Two or more of the low refractive index layers are disposed between the first emission band and the second emission band, at least two of the low refractive index layers are in direct contact with each other, the sum of the film thicknesses of each of the at least two directly contacting low refractive index layers is 50 nm or more, and at least one of the at least two directly contacting low refractive index layers contains the organic material and at least one selected from the group consisting of metals and metal compounds.) Condition (TDM2): At least one low refractive index layer having a film thickness of 50 nm or more is disposed between the first emission band and the second emission band, and the low refractive index layer having a film thickness of 50 nm or more contains the organic material and at least one selected from the group consisting of metals and metal compounds.)
[0116] As a method of counting the number of a plurality of light emitting units disposed between the anode and the cathode, it may be counted as the X-th stage, the (X + 1)-th stage, and the (X + 2)-th stage in order from the anode side (where X is an integer of 1 or more). In a tandem organic EL element, if one or more low refractive index layers are disposed between two emission bands and the total film thickness of the disposed low refractive index layers is 50 nm or more, the light extraction efficiency of the light emitting layer in the light emitting unit located at least on the cathode side of the low refractive index layer is improved. By disposing a low refractive index layer as described above between the emission band in the X-th stage light emitting unit and the emission band in the (X + 1)-th stage light emitting unit, the light extraction efficiency of the light emitting layer in at least the (X + 1)-th stage light emitting unit is improved.) The organic EL element according to the first embodiment has one or more low refractive index layers containing an organic material having a refractive index of 1.87 or less between the first emission band in the first light emitting unit and the second emission band in the second light emitting unit, satisfying condition (TDM1) or (TDM2). By satisfying such condition (TDM1) or (TDM2), the light extraction efficiency of the light emitting layer in the second emission band of the second light emitting unit is improved.) According to the organic EL element according to the first embodiment, the external quantum efficiency can be improved by improving the light extraction efficiency.)
[0117] The refractive index can be measured by the measurement method described in the examples below. In this specification, the refractive index value at 2.7 eV in the substrate parallel direction (Ordinary direction) of the value measured by multi-angle incidence spectroscopic ellipsometry measurement is defined as the refractive index of the material to be measured. The refractive index at 2.7 eV corresponds to the refractive index at 460 nm.
[0118] <Light-emitting unit> The organic EL element according to the first embodiment is an element including a plurality of light-emitting units between an anode and a cathode. An organic EL element in which a plurality of light-emitting units are stacked may be referred to as a tandem type organic EL element.
[0119] The organic EL element according to the first embodiment includes at least a first light-emitting unit and a second light-emitting unit as two or more light-emitting units. In one aspect of the organic EL element according to the first embodiment, the first light-emitting unit is the light-emitting unit disposed closest to the anode side. In one aspect of the organic EL element according to the first embodiment, the second light-emitting unit is the light-emitting unit disposed closest to the cathode side.
[0120] In one aspect of the organic EL element according to the first embodiment, two or more light-emitting units further include a third light-emitting unit. In one aspect of the organic EL element according to the first embodiment, when the organic EL element includes a first light-emitting unit, a second light-emitting unit, and a third light-emitting unit as two or more light-emitting units, the first light-emitting unit, the second light-emitting unit, and the third light-emitting unit may be arranged in this order from the anode side toward the cathode side. In this case, for example, the first light-emitting unit may be the light-emitting unit arranged in the first stage, the second light-emitting unit may be the light-emitting unit arranged in the second stage, and the third light-emitting unit may be the light-emitting unit arranged in the third stage. Also, the third light-emitting unit, the first light-emitting unit, and the second light-emitting unit may be arranged in this order. In this case, for example, the third light-emitting unit may be the light-emitting unit arranged in the first stage, the first light-emitting unit may be the light-emitting unit arranged in the second stage, and the second light-emitting unit may be the light-emitting unit arranged in the third stage. Also, in one aspect of the organic EL element according to the first embodiment, when the organic EL element includes four or more light-emitting units, namely, a first light-emitting unit, a second light-emitting unit, a third light-emitting unit, and a fourth light-emitting unit, the first light-emitting unit (first stage), the second light-emitting unit (second stage), the third light-emitting unit (third stage), and the fourth light-emitting unit (fourth stage) may be arranged in this order from the anode side to the cathode side, or the third light-emitting unit (first stage), the first light-emitting unit (second stage), the second light-emitting unit (third stage), and the fourth light-emitting unit (fourth stage) may be arranged in this order.
[0121] <Emission band> In the organic EL element according to the first embodiment, two or more light-emitting units each independently include an emission band. That is, the organic EL element according to the first embodiment includes two or more emission bands. In the organic EL element according to the first embodiment, the first light-emitting unit includes a first emission band, and the second light-emitting unit includes a second emission band.
[0122] In the organic EL element according to the first embodiment, each emission band independently includes at least one light-emitting layer. In one aspect of the organic EL element according to the first embodiment, each emission band may independently include only one light-emitting layer or two or more light-emitting layers. In one aspect of the organic EL element according to the first embodiment, each light-emitting layer independently contains a host material. In one aspect of the organic EL element according to the first embodiment, each light-emitting layer independently contains a host material and a light-emitting compound. In one aspect of the organic EL element according to the first embodiment, the light-emitting compounds contained in each light-emitting layer are each independently fluorescent or phosphorescent. In the organic EL element according to the first embodiment, it is preferable that at least one of the light-emitting layers contains a fluorescent light-emitting compound.
[0123] In one aspect of the organic EL element according to the first embodiment, the first emission band includes a first light-emitting layer. In one aspect of the organic EL element according to the first embodiment, the first light-emitting layer contains a first host material.
[0124] In one aspect of the organic EL element according to the first embodiment, the first emission band contains a first light-emitting compound. In one aspect of the organic EL element according to the first embodiment, the first light-emitting layer contains a first light-emitting compound. In one aspect of the organic EL element according to the first embodiment, the first light-emitting layer contains a first host material and a first light-emitting compound.
[0125] In one aspect of the organic EL element according to the first embodiment, the second emission band contains a second light-emitting compound. In one aspect of the organic EL element according to the first embodiment, the second light-emitting layer contains a second light-emitting compound. In one aspect of the organic EL element according to the first embodiment, the second light-emitting layer contains a second host material and a second light-emitting compound.
[0126] In one aspect of the organic EL element according to the first embodiment, the first light-emitting compound and the second light-emitting compound are the same as or different from each other.
[0127] In one aspect of the organic EL element according to the first embodiment, one or both of the first light-emitting compound and the second light-emitting compound are compounds that exhibit light emission with a maximum peak wavelength of 500 nm or less. In one aspect of the organic EL element according to the first embodiment, one or both of the first light-emitting compound and the second light-emitting compound are compounds that exhibit light emission with a maximum peak wavelength of 480 nm or less. In one aspect of the organic EL element according to the first embodiment, one or both of the first light-emitting compound and the second light-emitting compound are compounds that exhibit light emission with a maximum peak wavelength of 430 nm or more. The method for measuring the maximum peak wavelength of the compound is as follows. The compound to be measured is 10 -6 mol / L or more and 10 -5Prepare a toluene solution dissolved at a concentration of 1 mol / L or less and put it in a quartz cell, and measure the emission spectrum of this sample at room temperature (300 K). Let the vertical axis of the emission spectrum be the emission intensity and the horizontal axis be the wavelength. The emission spectrum can be measured, for example, with a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Technologies Corporation. The emission spectrum measuring device is not limited to the device used here.
[0128] (Host material and dopant material) In one aspect of the organic EL element according to this embodiment, one or more light-emitting layers in the emission band each independently contain a host material and a dopant material. The host material may also be referred to as a matrix material. The dopant material may also be referred to as a luminescent compound, a guest material, an emitter, or a light-emitting material.
[0129] In one aspect of the organic EL element according to this embodiment, one or more light-emitting layers in the emission band each independently contain at least one dopant material selected from the group consisting of the following dopant materials and at least one host material selected from the group consisting of the following host materials.
[0130] (Dopant material for the light-emitting layer) The light-emitting layer is a layer containing a highly luminescent substance, and various materials can be used. For example, as the highly luminescent substance, a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used. A fluorescent compound is a compound that can emit light from the singlet excited state, and a phosphorescent compound is a compound that can emit light from the triplet excited state.
[0131] As blue fluorescent materials that can be used in the light-emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. can be used. Specifically, N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), etc. can be mentioned.
[0132] As green fluorescent materials that can be used in the light-emitting layer, aromatic amine derivatives, etc. can be used. Specifically, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracene-9-amine (abbreviation: DPhAPhA), etc. can be mentioned.
[0133] As red fluorescent light-emitting materials that can be used in the light-emitting layer, tetracene derivatives, diamine derivatives, etc. can be used. Specifically, N,N,N’,N’-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N’,N’-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), etc. can be mentioned.
[0134] As blue phosphorescent light-emitting materials that can be used in the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used. Specifically, bis[2-(4’,6’-difluorophenyl)pyridinato-N,C2’]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4’,6’-difluorophenyl)pyridinato-N,C2’]iridium(III) picolinate (abbreviation: FIrpic), bis[2-(3’,5’-bis(trifluoromethyl)phenyl)pyridinato-N,C2’]iridium(III) picolinate (abbreviation: Ir(CF3ppy)2(pic)), bis[2-(4’,6’-difluorophenyl)pyridinato-N,C2’]iridium(III) acetylacetonate (abbreviation: FIr(acac)), etc. can be mentioned.
[0135] As green phosphorescent light-emitting materials that can be used in the light-emitting layer, iridium complexes, etc. are used. Tris(2-phenylpyridinato-N,C2’)iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridinato-N,C2’)iridium(III) acetylacetonate (abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazolato)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)), etc. can be mentioned.
[0136] As red phosphorescent materials that can be used in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used. Specifically, bis[2-(2'-benzo[4,5-α]thienyl)pyridinato-N,C3']iridium(III) acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinolinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP), and other organometallic complexes can be mentioned. In addition, rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: Eu(DBM)3(Phen)), and tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: Eu(TTA)3(Phen)) can be used as phosphorescent compounds because they emit light from rare earth metal ions (electron transitions between different multiplicities).
[0137] (Compound represented by formula (2)) In one aspect of the organic EL element according to the first embodiment, the dopant material (luminescent compound) is a compound represented by the following formula (2). In one aspect of the organic EL element according to the first embodiment, the first luminescent compound and the second luminescent compound are compounds represented by the following formula (2). The compound represented by the following formula (2) may be referred to as the second compound.
[0138] [Chemical formula]
[0139] (In the formula (2), the Ax ring, Bx ring, and Cx ring are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms, R 201 and R 202 are each independently bonded to the Ax ring, Bx ring, or Cx ring to form a substituted or unsubstituted monocyclic ring, bonded to the Ax ring, Bx ring, or Cx ring to form a substituted or unsubstituted condensed ring, or not bonded to the Ax ring, Bx ring, and Cx ring, not forming the substituted or unsubstituted monocyclic ring, and not forming the substituted or unsubstituted condensed ring, R 201 and R 202 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, an iminyl group represented by -CR 25 =N, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 25 is a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 60 ring-forming atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, R 25 When there are a plurality of R 25 are the same as or different from each other.)
[0140] In one aspect of the organic EL element according to the first embodiment, the second compound is a compound represented by the following formula (21) or (22).
[0141]
Chemical formula
[0142] (In the above formula (21), R 201 and R 221 a pair of, R 221 ~R 223 a pair of two or more adjacent ones among, R 223 and R 202 a pair of, R 202 and R 224 a pair of, R 224 ~R 227 a pair of two or more adjacent ones among, R 227 and R 228 a pair of, R 228 ~R 231 a pair of two or more adjacent ones among, and R 231 and R 201 a pair of selected from the group consisting of one or more pairs combine with each other to form a substituted or unsubstituted monocyclic ring, combine with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other, do not form the substituted or unsubstituted monocyclic ring, and do not form the substituted or unsubstituted condensed ring R 201 and R 202 201 are respectively synonymous with R 202 and Rin the above formula (2),and are in the above formula (22), Xa is O, S, Se, C(R 203 )(R 204 ), or N(R 205 ), and R 201 and R 221 a pair of, R 221 ~R 223 a pair of two or more adjacent ones among, R223 and R 202 and the group, R 202 and R 224 and the group, R 224 ~R 227 consisting of two or more adjacent ones among them, and R 237 ~R 240 selected from one or more groups consisting of groups consisting of two or more adjacent ones among them is bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted condensed ring, R 201 and R 202 are each independently, respectively, R in the formula (2) 201 and R 202 and have the same meaning, in the formula (21) or (22), R 203 R, 204 and R 205 and not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted condensed ring, R 221 R, 222 R, 223 R, 224 R, 225 R, 226 R, 227 R, 228 R, 229 R, 230 R, 231 R, 237 R, 238 R, 239 and R 240 are each independently, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901)(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, -N(R 906 )(R 907 )-represented group, halogen atom, cyano group, nitro group, substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901 ~R 907 are each independently, hydrogen atom, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901 When there are a plurality of R 901 are the same as or different from each other, and when there are a plurality of R 902 are the same as or different from each other, and when there are a plurality of R 902 are the same as or different from each other, and when there are a plurality of R 903 are the same as or different from each other, and when there are a plurality of R 903 are the same as or different from each other, and when there are a plurality of R 904 are the same as or different from each other, and when there are a plurality of R 904 are the same as or different from each other, and when there are a plurality of R 905 are the same as or different from each other, and when there are a plurality of R 905 are the same as or different from each other, and when there are a plurality of R 906 are the same as or different from each other, and when there are a plurality of R 906 are the same as or different from each other, and when there are a plurality of R 907 are the same as or different from each other, and when there are a plurality of R 907 are the same as or different from each other.)
[0143] In one aspect of the organic EL element according to the first embodiment, R in the formula (21) or (22) 201 and R 202 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
[0144] In one aspect of the organic EL element according to the first embodiment, R in the formula (21) or (22) 201 and R 202 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.
[0145] In one aspect of the organic EL element according to the first embodiment, R in the formula (21) or (22) 201 and R 202 are each independently a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms.
[0146] In one aspect of the organic EL element according to the first embodiment, R in the formula (21) or (22) 201 and R 202 are each independently a group represented by the following formula (23).
[0147]
Chemical formula
[0148] (In the formula (23), R 241 , R 242 , R 243 , R 244 , and R 245 one or more of the sets of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring of R241 , R 242 , R 243 , R 244 , and R 245 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, -N(R 906 )(R 907 )-represented group, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901 ~ R 907 are each independently the same as R 901 ~ R 907 in the formulas (21) and (22), When there are a plurality of R 241 , the plurality of R 241 may be the same as or different from each other, When there are a plurality of R 242 , the plurality of R 242 may be the same as or different from each other, When there are a plurality of R 243 , the plurality of R 243 may be the same as or different from each other, When there are a plurality of R 244 , the plurality of R 244 may be the same as or different from each other, A plurality of Rs 245 When there are a plurality of Rs 245 they may be the same as or different from each other, * indicates the bonding position.)
[0149] In one aspect of the organic EL element according to the first embodiment, the second compound is a compound represented by the following formula (211) or (221).
[0150]
Chemical formula
[0151]
Chemical formula
[0152] (In the above formulas (211) and (221), R 221 ~R 231 and R 237 ~R 240 are respectively synonymous with R 221 ~R 231 and R 237 ~R 240 in the above formulas (21) and (22), and R 241 ~R 245 are respectively synonymous with R 241 ~R 245 in the above formula (23), and Xa in the above formula (221) is synonymous with Xa in the above formula (22).)
[0153] In one aspect of the organic EL element according to the first embodiment, the second compound is a compound represented by the following formula (212) or (222).
[0154]
Chemical formula
[0155] (In the above formula (212), R 222 , R 226 and R 229is, respectively, R in the formula (21). 222 , R 226 and R 229 is synonymous with, In the formula (222), Xa, R 225 and R 239 are, respectively, Xa, R in the formula (22). 225 and R 239 is synonymous with, R in the formulas (212) and (222). 243 is, respectively, independently, R in the formula (23). 243 is synonymous with.)
[0156] In one aspect of the organic EL element according to the first embodiment, in the formulas (22), (221) and (222), Xa is S (sulfur atom) or O (oxygen atom).
[0157] In this specification, the maximum peak wavelength of fluorescence emission may be referred to as the fluorescence emission maximum peak wavelength.
[0158] In one aspect of the first embodiment, it is preferable that the fluorescence emission maximum peak wavelength of the second compound is 430 nm or more, more preferably 440 nm or more, and even more preferably 445 nm or more. In one aspect of the first embodiment, it is preferable that the fluorescence emission maximum peak wavelength of the second compound is 480 nm or less, more preferably 470 nm or less, and even more preferably 465 nm or less. In the first embodiment, when the fluorescence emission maximum peak wavelength of the second compound is 430 nm or more, an electronic device such as a display equipped with an organic EL element containing the compound according to this embodiment is likely to obtain appropriate blue light emission. In the first embodiment, when the fluorescence emission peak maximum wavelength of the second compound is 480 nm or less, an electronic device such as a display equipped with an organic EL element containing the compound according to this embodiment is likely to obtain appropriate blue light emission.
[0159] In this specification, the maximum fluorescence emission peak wavelength refers to the maximum peak wavelength of the fluorescence spectrum measured for a toluene solution in which the compound to be measured is dissolved at a concentration of 10 -6 mol / L or more and 10 -5 mol / L or less, at which the emission intensity in the measured fluorescence spectrum is maximum. As the measuring apparatus, a fluorescence spectrum measuring apparatus (apparatus name: FP-8300, manufactured by JASCO Corporation) can be used. Note that the fluorescence spectrum measuring apparatus is not limited to the apparatus exemplified here.
[0160] In one aspect of the organic EL element according to the first embodiment, it is also preferable that all the groups described as "substituted or unsubstituted" are "unsubstituted" groups.
[0161] In this specification, unless otherwise specified, the details of the substituents (any substituents) in the case of "substituted or unsubstituted" included in the definitions of the respective formulas of each compound are as described in the section of "substituents in the case of'substituted or unsubstituted'".
[0162] (Method for producing the second compound according to the first embodiment) The second compound according to the first embodiment can be produced by a known method. Further, the second compound according to the first embodiment can also be produced by following a known method and using known alternative reactions and raw materials adapted to the target product.
[0163] (Specific examples of the second compound according to the first embodiment) Specific examples of the second compound according to the first embodiment include, for example, the following compounds. However, the present invention is not limited to these specific examples.
[0164] In this specification, in the specific examples of the compound, D represents a deuterium atom, Me represents a methyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.
[0165] [Chemical formula]
[0166] [Chemical formula]
[0167] [Chemical formula]
[0168] (Host material of the light-emitting layer) The light-emitting layer may have a structure in which the above-described highly luminescent substance (dopant material) is dispersed in another substance (host material).
[0169] As the substance for dispersing the highly luminescent substance, various compounds can be used, and it is preferable to use a substance having a higher lowest unoccupied molecular orbital level (LUMO level) and a lower highest occupied molecular orbital level (HOMO level) than the highly luminescent substance.
[0170] The substance (host material) for dispersing the highly luminescent substance is preferably at least one selected from the group consisting of the compounds shown in the following (1) to (4). (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives (3) Condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives (4) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives Specifically, examples of the metal complex include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), and the like. Examples of the heterocyclic compound include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2’,2’’-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), and the like. Examples of the condensed aromatic compounds include 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9’-bianthryl (abbreviation: BANT), 9,9’-(stilbene-3,3’-diyl)diphenanthrene (abbreviation: DPNS), 9,9’-(stilbene-4,4’-diyl)diphenanthrene (abbreviation: DPNS2), 3,3’,3’’-(benzene-1,3,5-triyl)tripyrene (abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenylchrysene, and the like. Examples of the aromatic amine compounds include N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), NPB (or α-NPD), TPD, DFLDPBi, BSPB, and the like.
[0171] (Compound represented by formula (3)) In one aspect of the organic EL element according to the first embodiment, the host material is a compound represented by the following formula (3). In one aspect of the organic EL element according to the first embodiment, the first host material and the second host material are compounds represented by the following formula (3). The compound represented by the following formula (3) may be referred to as the third compound.
[0172] In the organic EL element according to the first embodiment, the third compound is a compound represented by the following formula (3).
[0173] [Chemical formula]
[0174] (In the above formula (3), R 31 ~R 38 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by, -O-(R 904 ) group represented by, -S-(R 905 ) group represented by, -N(R 906 )(R 907 ) group represented by, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 group represented by, -COOR 802 group represented by, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, L 31 and L 32 each independently is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, Ar 31 and Ar 32 each independently is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.)
[0175] In the third compound, R 901 ~R 907 each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, and when a plurality of R 901 are present, the plurality of R 901 are the same as or different from each other, and when a plurality of R 902 are present, the plurality of R 902 are the same as or different from each other, and when a plurality of R 903 are present, the plurality of R 903 are the same as or different from each other, and when a plurality of R 904 are present, the plurality of R 904 are the same as or different from each other, and when a plurality of R 905 are present, the plurality of R 905 are the same as or different from each other, and when a plurality of R 906 are present, the plurality of R 906 are the same as or different from each other, and when a plurality of R 907 are present, the plurality of R 907are identical to or different from each other.
[0176] In one aspect of the organic EL element according to the first embodiment, the third compound is a compound represented by the following formula (31).
[0177]
Chemical formula
[0178] (In the formula (31), R 31 ~R 38 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, -N(R 906 )(R 907 )-represented group, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, X3 is an oxygen atom or a sulfur atom, provided that one of R 311 ~R 318 is a single bond bonded to *p1, and one or more sets of two or more adjacent ones among R 311 ~R 318 that are not a single bond bonded to *p1 form Combine with each other to form a substituted or unsubstituted monocyclic ring, or Combine with each other to form a substituted or unsubstituted condensed ring, or Do not combine with each other, Rather than a single bond connecting to *p1, and do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring, R 311 ~R 318 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, -N(R 906 )(R 907 )-represented group, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, L 31 and L 32 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, Ar 32 is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
[0179] In one aspect of the organic EL element according to the first embodiment, the third compound is a compound represented by the following formula (31A), (31B) or (31C).
[0180]
Chemical formula
[0181]
Chemical formula
[0182]
Chemical formula
[0183] (In the above formulas (31A), (31B) and (31C), R 31 ~R 38 , L 31 , L 32 , and Ar 32 are respectively synonymous with R 31 ~R 38 , L 31 , L 32 , and Ar 32 in the formula (3), X3 is synonymous with X3 in the formula (31), provided that one of R 311 ~R 318 and R 321 ~R 324 is a single bond bonded to *p1, and one or more sets of two or more adjacent ones among R 311 ~R 318 and R 321 ~R 324 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or Combine with each other to form a substituted or unsubstituted condensed ring, or Do not combine with each other, Rather than a single bond connecting to *p1, it does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, R 311 ~R 318 and R 321 ~R 324 are each independently A hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, -N(R 906 )(R 907 )-represented group, A halogen atom, A cyano group, A nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.)
[0184] In one aspect of the organic EL element according to the first embodiment, the third compound is represented by the formula (31A), and R 311 is a single bond connecting to *p1.
[0185] In one aspect of the organic EL element according to the first embodiment, the third compound is represented by the formula (31B), and R 311 is a single bond connecting to *p1.
[0186] In one aspect of the organic EL element of the first embodiment, the compound represented by the formula (3) is a compound represented by the following formula (311), (312), (313), or (314).
[0187]
Chemical formula
[0188]
Chemical formula
[0189]
Chemical formula
[0190]
Chemical formula
[0191] (In the formulas (311), (312), (313), and (314), R 31 ~R 38 , R 311 ~R 318 , L 31 , L 32 , Ar 32 and X3 are as defined in the formula (3) or (31), respectively.)
[0192] In one aspect of the organic EL element of the first embodiment, one or more of the pairs consisting of two or more adjacent ones among the R 311 ~R 318 that are not single bonds bonded to *p1 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring.
[0193] In one aspect of the organic EL element of the first embodiment, the R 311 ~R 314Among the two or more adjacent ones of them, any combination does not bond to each other, and R that is not a single bond bonding to *p1 315 ~R 318 One or more of the combinations consisting of two or more adjacent ones among them bond to each other to form a substituted or unsubstituted monocyclic ring, or bond to each other to form a substituted or unsubstituted condensed ring.
[0194] In one aspect of the organic EL element of the first embodiment, R that is not a single bond bonding to *p1 311 ~R 318 Among the two or more adjacent ones of them, any combination does not bond to each other.
[0195] In one aspect of the organic EL element of the first embodiment, L 31 and L 32 are each independently a single bond or an arylene group having 6 to 14 ring-forming carbon atoms which may be substituted or unsubstituted.
[0196] In one aspect of the organic EL element of the first embodiment, L 31 and L 32 are each independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.
[0197] In one aspect of the organic EL element of the first embodiment, at least one of Ar 31 and Ar 32 is an aryl group having 6 to 50 ring-forming carbon atoms which may be substituted or unsubstituted.
[0198] In one aspect of the organic EL element of the first embodiment, Ar 32 is an aryl group having 6 to 50 ring-forming carbon atoms which may be substituted or unsubstituted.
[0199] In one aspect of the organic EL element of the first embodiment, at least one of Ar 31 and Ar 32 is a group represented by the following formula (32a), (32b), (32c) or (32d).
[0200] [Chemical]
[0201] (In the above formulas (32a), (32b), (32c) and (32d), Among the plurality of Rs 320 One or more sets of two or more adjacent ones among them Are bonded to each other to form a substituted or unsubstituted monocyclic ring, Are bonded to each other to form a substituted or unsubstituted condensed ring, or Do not bond to each other, Do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring, and the R 320 Is A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by -O-(R 904 ) group represented by -S-(R 905 ) group represented by -N(R 906 )(R 907 ) group represented by A halogen atom, A cyano group, A nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, The plurality of Rs 320 Are the same as or different from each other, * is a single bond that binds to L 31 Or L 32 .)
[0202] In one aspect of the organic EL element of the first embodiment, X3 is an oxygen atom.
[0203] In one aspect of the organic EL element of the first embodiment, Ar 32 is a group represented by the formula (32a), (32b), (32c) or (32d).
[0204] In one aspect of the organic EL element of the first embodiment, R 31 ~R 38 is a hydrogen atom.
[0205] In one aspect of the organic EL element of the first embodiment, the compound represented by the formula (3) is a compound represented by the following formula (325), (326), (327), (328) or (329).
[0206]
Chemical formula
[0207]
Chemical formula
[0208]
Chemical formula
[0209] (In the formulas (325) to (329), R 315 ~R 318 and Ar 32 are synonymous with R 315 ~R 318 and Ar 32 in the formula (3), respectively.)
[0210] In one aspect of the organic EL element of the first embodiment, one or more sets of two or more adjacent ones among R 315 ~R 318 are bonded to each other to form a substituted or unsubstituted monocyclic ring.
[0211] In one aspect of the organic EL element of the first embodiment, R 315 ~R 318 One or more sets of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted benzene ring.
[0212] (Method for producing the third compound according to the first embodiment) The third compound according to the first embodiment can be produced by a known method. Further, the third compound according to the first embodiment can also be produced by following a known method and using known alternative reactions and raw materials adapted to the target product.
[0213] (Specific examples of the third compound according to the first embodiment) Specific examples of the third compound according to the first embodiment include, for example, the following compounds. However, the present invention is not limited to these specific examples.
[0214]
Chemical formula
[0215] In this specification, the "host material" is, for example, a material contained in "50 mass% or more of the layer". Therefore, the light-emitting layer contains, for example, a host material in 50 mass% or more of the total mass of the light-emitting layer. When the organic EL element has a plurality of light-emitting layers, for example, each of the plurality of light-emitting layers contains a host material in 50 mass% or more of the total mass of each light-emitting layer. Further, for example, the "host material" may be contained in 60 mass% or more, 70 mass% or more, 80 mass% or more, 90 mass% or more, or 95 mass% or more of the light-emitting layer. Further, for example, the "host material" may be contained in 99.5 mass% or less, or 99 mass% or less of the light-emitting layer. When the light-emitting layer contains a host material and a dopant material, the upper limit of the total content ratio of the host material and the dopant material is 100 mass%.
[0216] In one aspect of the organic EL element according to the first embodiment, one or more light-emitting layers do not contain a metal complex. Further, in one aspect of the organic EL element according to the first embodiment, one or more light-emitting layers do not contain a boron-containing complex.
[0217] In one aspect of the organic EL element according to the first embodiment, one or more light-emitting layers do not contain a phosphorescent material.
[0218] In one aspect of the organic EL element according to the first embodiment, one or more light-emitting layers do not contain a heavy metal complex and a phosphorescent rare earth metal complex. In one aspect of the organic EL element according to the first embodiment, one or more light-emitting layers do not contain heavy metal complexes such as, for example, iridium complexes, osmium complexes, and platinum complexes.
[0219] <Low refractive index layer> In the organic EL element according to the first embodiment, one or more low refractive index layers are disposed between at least any two of two or more light-emitting bands. In the organic EL element according to the first embodiment, one or more low refractive index layers are disposed between the first light-emitting band and the second light-emitting band. In the organic EL element according to the first embodiment, each of the one or more low refractive index layers independently contains an organic material having a refractive index of 1.87 or less. The organic materials having a refractive index of 1.87 or less contained in each of the one or more low refractive index layers may have the same chemical structure or different chemical structures from each other. The organic material having a refractive index of 1.87 or less may be referred to as a low refractive index organic material in some cases.
[0220] In one aspect of the organic EL element according to the first embodiment, each of the one or more low refractive index layers independently contains 50 mass% or more, 60 mass% or more, 70 mass% or more, 80 mass% or more, 90 mass% or more, 95 mass% or more, or 99 mass% or more of an organic material having a refractive index of 1.87 or less. In one aspect of the organic EL element according to the first embodiment, each of the one or more low refractive index layers may be a layer containing only an organic material having a refractive index of 1.87 or less.
[0221] In one aspect of the organic EL element according to the first embodiment, the refractive index of at least one of the organic materials (low refractive index organic materials) contained in one or more low refractive index layers is 1.83 or less.
[0222] (Condition (TDM1)) Condition (TDM1) will be described. In condition (TDM1), two or more low refractive index layers are arranged between the first emission band and the second emission band, and at least two low refractive index layers are in direct contact. Further, in condition (TDM1), the sum of the film thicknesses of each of the at least two directly contacting low refractive index layers is 50 nm or more, and at least one of the at least two directly contacting low refractive index layers contains an organic material (low refractive index organic material) having a refractive index of 1.87 or less and at least one selected from the group consisting of metals and metal compounds.
[0223] In one aspect of the organic EL element according to the first embodiment, when condition (TDM1) is satisfied, the film thicknesses of each of the at least two directly contacting low refractive index layers are, independently of each other, less than 50 nm or 45 nm or less.
[0224] In one aspect of the organic EL element according to the first embodiment, when condition (TDM1) is satisfied, among the at least two directly contacting low refractive index layers, the film thickness of at least one low refractive index layer is, independently of each other, 30 nm or less, 25 nm or less, 20 nm or less, or 18 nm or less.
[0225] In one aspect of the organic EL element according to the first embodiment, when condition (TDM1) is satisfied, the film thicknesses of each of the at least two directly contacting low refractive index layers are, independently of each other, 3 nm or more or 5 nm or more.
[0226] In one aspect of the organic EL element according to the first embodiment, the sum of the film thicknesses of each of the at least two directly contacting low refractive index layers is 60 nm or more or 70 nm or more.
[0227] In one aspect of the organic EL element according to the first embodiment, the organic EL element satisfies the condition (TDM1), and in the condition (TDM1), the sum of the film thicknesses of at least two low refractive index layers that are in direct contact is 100 nm or less, or 90 nm or less.
[0228] In one aspect of the organic EL element according to the first embodiment, for the condition (TDM1) when the first low refractive index layer and the second low refractive index layer are arranged in this order between the first light emission band and the second light emission band as the two low refractive index layers from the first light emission band side, it will be described as the condition (TDM1-1). In the condition (TDM1-1), the first low refractive index layer and the second low refractive index layer are in direct contact, the sum of the film thickness of the first low refractive index layer and the film thickness of the second low refractive index layer is 50 nm or more, and at least one of the first low refractive index layer and the second low refractive index layer contains at least one selected from the group consisting of a low refractive index organic material and a metal and a metal compound.
[0229] In one aspect of the organic EL element according to the first embodiment, for the condition (TDM1) when the third low refractive index layer, the first low refractive index layer, and the second low refractive index layer are arranged in this order between the first light emission band and the second light emission band as the three low refractive index layers from the first light emission band side, it will be described as the condition (TDM1-2).
[0230] In an example of the condition (TDM1-2), the third low refractive index layer and the first low refractive index layer are in direct contact, the first low refractive index layer and the second low refractive index layer are in direct contact, the sum of the film thickness of the first low refractive index layer, the film thickness of the second low refractive index layer, and the film thickness of the third low refractive index layer is 50 nm or more, and at least one of the first low refractive index layer, the second low refractive index layer, and the third low refractive index layer contains at least one selected from the group consisting of a low refractive index organic material and a metal and a metal compound.
[0231] In one aspect of the organic EL element according to the first embodiment, for the condition (TDM1) when, as the four low refractive index layers, the third low refractive index layer, the first low refractive index layer, the second low refractive index layer, and the fourth low refractive index layer are arranged in this order between the first emission band and the second emission band, the condition (TDM1-3) will be described.
[0232] In an example of the condition (TDM1-3), the third low refractive index layer and the first low refractive index layer are in direct contact, the first low refractive index layer and the second low refractive index layer are in direct contact, the second low refractive index layer and the fourth low refractive index layer are in direct contact, the sum of the film thicknesses of the first low refractive index layer, the second low refractive index layer, the third low refractive index layer, and the fourth low refractive index layer is 50 nm or more, and at least one of the first low refractive index layer, the second low refractive index layer, the third low refractive index layer, and the fourth low refractive index layer contains at least one selected from the group consisting of a low refractive index organic material and a metal and a metal compound.
[0233] In one aspect of the organic EL element according to the first embodiment, for the condition (TDM1) when, as the five low refractive index layers, the fifth low refractive index layer, the third low refractive index layer, the first low refractive index layer, the second low refractive index layer, and the fourth low refractive index layer are arranged in this order between the first emission band and the second emission band, the condition (TDM1-4) will be described.
[0234] In an example of the condition (TDM1-4), the fifth low refractive index layer and the third low refractive index layer are in direct contact, the third low refractive index layer and the first low refractive index layer are in direct contact, the first low refractive index layer and the second low refractive index layer are in direct contact, the second low refractive index layer and the fourth low refractive index layer are in direct contact, the sum of the film thicknesses of the first low refractive index layer, the second low refractive index layer, the third low refractive index layer, the fourth low refractive index layer, and the fifth low refractive index layer is 50 nm or more, and at least one of the first low refractive index layer, the second low refractive index layer, the third low refractive index layer, the fourth low refractive index layer, and the fifth low refractive index layer contains at least one selected from the group consisting of a low refractive index organic material and a metal and a metal compound.
[0235] In one aspect of the organic EL element according to the first embodiment, the organic EL element satisfies condition (TDM1), and at least two low refractive index layers that are in direct contact in condition (TDM1) contain different compounds from each other. In one aspect of the organic EL element according to the first embodiment, the low refractive index organic materials contained in each of two or more directly contacting low refractive index layers are different compounds from each other. For example, when the organic EL element has a first low refractive index layer and a second low refractive index layer as two low refractive index layers, the first low refractive index layer contains one kind of compound AA, and the second low refractive index layer contains one kind of compound BB, this corresponds to the case where at least two directly contacting low refractive index layers (the first low refractive index layer and the second low refractive index layer) contain different compounds from each other. Also, when the organic EL element has a first low refractive index layer and a second low refractive index layer as two low refractive index layers, the first low refractive index layer contains two kinds of compounds AA and AB, and the second low refractive index layer contains one kind of compound BB, since both compounds AA and AB are different from compound BB, this corresponds to the case where at least two directly contacting low refractive index layers (the first low refractive index layer and the second low refractive index layer) contain different compounds from each other. Note that compounds AA, AB, and BB are different compounds from each other. On the other hand, when the organic EL element has a first low refractive index layer and a second low refractive index layer as two low refractive index layers, the first low refractive index layer contains two kinds of compounds AA and AB, and the second low refractive index layer contains one kind of compound AA, with respect to compound AA, since the first low refractive index layer and the second low refractive index layer contain the same compound, this does not correspond to the case where two directly contacting low refractive index layers (the first low refractive index layer and the second low refractive index layer) contain different compounds from each other. Regarding the case where the organic EL element has three, four, five, or six or more low refractive index layers, whether they contain different compounds from each other or the same compound, the same way of thinking as above can be applied.
[0236] In one aspect of the organic EL element according to the first embodiment, when the organic EL element satisfies the condition (TDM1), and the absolute value of the difference in refractive index between two organic materials (low refractive index organic materials) selected from the group consisting of the organic materials (low refractive index organic materials) each contained in at least two low refractive index layers in direct contact in the condition (TDM1) is defined as Δn, at least one of the Δn values is less than 0.10. In the organic EL element according to the first embodiment, Δn is 0 or more.
[0237] In one aspect of the organic EL element according to the first embodiment, for example, when the organic EL element satisfies the condition (TDM1-1), the absolute value Δn of the refractive index difference of the low refractive index organic material 12 is less than 0.10.
[0238] Also, in one aspect of the organic EL element according to the first embodiment, for example, when the organic EL element satisfies the condition (TDM1-2), at least one of Δn 12 and Δn 13 is less than 0.10.
[0239] Also, in one aspect of the organic EL element according to the first embodiment, for example, when the organic EL element satisfies the condition (TDM1-3), at least one of Δn 12 , Δn 13 and Δn 24 is less than 0.10.
[0240] Also, in one aspect of the organic EL element according to the first embodiment, for example, when the organic EL element satisfies the condition (TDM1-4), at least one of Δn 35 , Δn 12 , Δn 13 and Δn 24 is less than 0.10.
[0241] Δn 12 , Δn 13 , Δn 24 , and Δn 35 are defined as follows. Δn 12 =|n1 - n2| Δn13 = |n1 - n3| Δn 24 = |n2 - n4| Δn 35 = |n3 - n5| n1: Refractive index of the low - refractive - index organic material contained in the first low - refractive - index layer n2: Refractive index of the low - refractive - index organic material contained in the second low - refractive - index layer n3: Refractive index of the low - refractive - index organic material contained in the third low - refractive - index layer n4: Refractive index of the low - refractive - index organic material contained in the fourth low - refractive - index layer n5: Refractive index of the low - refractive - index organic material contained in the fifth low - refractive - index layer Δn 12 : Absolute value of the difference between refractive index n1 and refractive index n2 Δn 13 : Absolute value of the difference between refractive index n1 and refractive index n3 Δn 24 : Absolute value of the difference between refractive index n2 and refractive index n4 Δn 35 : Absolute value of the difference between refractive index n3 and refractive index n5
[0242] (Condition (TDM2)) The condition (TDM2) will be described. In the condition (TDM2), at least one low - refractive - index layer with a film thickness of 50 nm or more is disposed between the first emission band and the second emission band, and the low - refractive - index layer with a film thickness of 50 nm or more contains an organic material (low - refractive - index organic material) with a refractive index of 1.87 or less and at least one selected from the group consisting of metals and metal compounds.
[0243] For example, even when only one layer (low - refractive - index layer) containing a low - refractive - index organic material is disposed between the first emission band and the second emission band, if the film thickness of the low - refractive - index layer is 50 nm or more, the condition (TDM2) is satisfied. In one aspect of the organic EL element according to the first embodiment, the condition (TDM2) in the case where one low - refractive - index layer with a film thickness of 50 nm or more is disposed between the first emission band and the second emission band will be described as the condition (TDM2 - 1). In an example of the condition (TDM2-1), a layer other than the low refractive index layer may be disposed between the first emission band and the second emission band. The low refractive index layer having a film thickness of 50 nm or more may be in direct contact with the first emission band or may not be in direct contact therewith. The low refractive index layer having a film thickness of 50 nm or more may be in direct contact with the second emission band or may not be in direct contact therewith.
[0244] In one aspect of the organic EL element according to the first embodiment, in addition to the low refractive index layer satisfying the condition (TDM1) or the condition (TDM2) between the emission band in a certain light emitting unit and the emission band in another light emitting unit, one or more layers containing an organic material having a refractive index exceeding 1.87 (which may be referred to as a high refractive index organic material) (which may be referred to as a high refractive index layer) may be included.
[0245] In one aspect of the organic EL element according to the first embodiment, at least one low refractive index layer satisfying the condition (TDM1) or the condition (TDM2) is disposed between the light emitting layer included in the emission band in a certain light emitting unit and the light emitting layer included in the emission band in another light emitting unit. In one aspect of the organic EL element according to the first embodiment, in addition to the low refractive index layer satisfying the condition (TDM1) or the condition (TDM2) between the light emitting layer included in the emission band in a certain light emitting unit and the light emitting layer included in the emission band in another light emitting unit, one or more high refractive index layers containing a high refractive index organic material may be included.
[0246] <Charge generation band> In one aspect of the organic EL element according to the first embodiment, it is preferable that charge generation bands are respectively disposed between two or more light emitting units. In one aspect of the organic EL element according to the first embodiment, the charge generation region preferably includes at least one charge generation layer independently. The charge generation layer is a layer that generates holes and electrons when a voltage is applied to the organic EL element, supplies electrons to the layer located on the anode side of the charge generation layer, and supplies holes to the layer located on the cathode side of the charge generation layer. The charge generation layer may be referred to as an intermediate layer, an intermediate electrode, an intermediate conductive layer, an electron extraction layer, a connection layer, or an intermediate insulating layer.
[0247] When the charge generation region is composed of a plurality of charge generation layers, the charge generation region preferably has an N-type charge generation layer disposed on the anode side and injecting electrons into the first light-emitting unit, and a P-type charge generation layer disposed on the cathode side and injecting holes into the second light-emitting unit. In one aspect of the organic EL element according to the first embodiment, one of the N-type charge generation layer and the P-type charge generation layer may be the first charge generation layer. In one aspect of the organic EL element according to the first embodiment, the N-type charge generation layer may be the first charge generation layer, and the P-type charge generation layer may be the second charge generation layer. In one aspect of the organic EL element according to the first embodiment, examples of the material that can be used for the charge generation layer of the charge generation region include known materials that can be used for the charge generation layer of a tandem-type organic EL element.
[0248] In one aspect of the organic EL element according to the first embodiment, at least one of the charge generation regions includes two or more charge generation layers.
[0249] In one aspect of the organic EL element according to the first embodiment, a first charge generation region is disposed between the first light-emitting unit and the second light-emitting unit. In one aspect of the organic EL element according to the first embodiment, the first charge generation region includes at least a first charge generation layer.
[0250] Also, in one aspect of the organic EL element according to the first embodiment, when the first light-emitting unit, the second light-emitting unit, and the third light-emitting unit are arranged in this order from the anode side toward the cathode side, a second charge generation band is arranged between the second light-emitting unit and the third light-emitting unit. Also, in one aspect of the organic EL element according to the first embodiment, when the third light-emitting unit, the first light-emitting unit, and the second light-emitting unit are arranged in this order from the anode side toward the cathode side, a second charge generation band is arranged between the third light-emitting unit and the first light-emitting unit.
[0251] In one aspect of the organic EL element according to the first embodiment, when the organic EL element satisfies the condition (TDM1), one of at least two low refractive index layers that are in direct contact in the condition (TDM1) is the first charge generation layer. In one aspect of the organic EL element according to the first embodiment, when the organic EL element satisfies the condition (TDM2), one of the low refractive index layers having a film thickness of 50 nm or more in the condition (TDM2) is the first charge generation layer.
[0252] In one aspect of the organic EL element according to the first embodiment, the first charge generation layer contains the organic material (an organic material having a refractive index of 1.87 or less (low refractive index organic material)) and at least one selected from the group consisting of metals and metal compounds. The low refractive index organic material contained in the first charge generation layer may be referred to as the first charge generation band material.
[0253] In one aspect of the organic EL element according to the first embodiment, the refractive index of the organic material (first charge generation band material) contained in the first charge generation layer is 1.83 or less, or 1.80 or less.
[0254] In one aspect of the organic EL element according to the first embodiment, the first charge generation band material is an electron transport band material (preferably, the first electron transport band material) described later. In one aspect of the organic EL element according to the first embodiment, the first charge generation band material contained in the first charge generation layer and the electron transport band material contained in the layer in the electron transport band (for example, the first electron transport layer) are different compounds from each other or the same compound.
[0255] In one aspect of the organic EL element according to the first embodiment, the first charge generation band further includes a second charge generation layer. In one aspect of the organic EL element according to the first embodiment, the second charge generation layer is disposed between the first charge generation layer and the second light emission band.
[0256] In one aspect of the organic EL element according to the first embodiment, when the organic EL element satisfies the condition (TDM1), at least two low refractive index layers directly in contact in the condition (TDM1) include the first charge generation layer and the second charge generation layer.
[0257] In one aspect of the organic EL element according to the first embodiment, the first charge generation band includes the first charge generation layer and the second charge generation layer in this order from the first light emission unit side.
[0258] In one aspect of the organic EL element according to the first embodiment, the first charge generation layer and the second charge generation layer are in direct contact with each other.
[0259] In one aspect of the organic EL element according to the first embodiment, the first charge generation layer is the aforementioned first low refractive index layer, and the second charge generation layer is the aforementioned second low refractive index layer.
[0260] In one aspect of the organic EL element according to the first embodiment, the sum of the film thickness of the first charge generation layer and the film thickness of the second charge generation layer is 10 nm or more, or 15 nm or more.
[0261] In one aspect of the organic EL element according to the first embodiment, the sum of the film thickness of the first charge generation layer and the film thickness of the second charge generation layer is 100 nm or less, 80 nm or less, or 50 nm or less.
[0262] In one aspect of the organic EL element according to the first embodiment, at least one of the first charge generation layer and the second charge generation layer contains an organic material (low refractive index organic material) having a refractive index of 1.87 or less and at least one selected from the group consisting of metals and metal compounds. In the first embodiment, the organic material (low refractive index organic material) having a refractive index of 1.87 or less contained in the second charge generation layer may be referred to as the second charge generation band material.
[0263] In one aspect of the organic EL element according to the first embodiment, the refractive index of the second charge generation band material is 1.83 or less or 1.80 or less.
[0264] In one aspect of the organic EL element according to the first embodiment, the refractive index of the first charge generation band material is 1.83 or less, and the refractive index of the second charge generation band material is 1.83 or less. In one aspect of the organic EL element according to the first embodiment, the refractive index of the first charge generation band material is 1.80 or less, and the refractive index of the second charge generation band material is 1.80 or less.
[0265] In one aspect of the organic EL element according to the first embodiment, the first charge generation band material and the second charge generation band material are different from each other.
[0266] In one aspect of the organic EL element according to the first embodiment, the refractive index of the first charge generation band material is greater than the refractive index of the second charge generation band material. In one aspect of the organic EL element according to the first embodiment, the refractive index of the first charge generation band material is greater than 1.70, and the refractive index of the second charge generation band material is 1.70 or less.
[0267] In one aspect of the organic EL element according to the first embodiment, the second charge generation layer contains the second charge generation band material and an acceptor material described later. In one aspect of the organic EL element according to the first embodiment, the content of the acceptor material in the second charge generation layer is less than 50% by mass. In one aspect of the organic EL element according to the first embodiment, the content of the acceptor material in the second charge generation layer is 10% by mass or less, or 5% by mass or less. In one aspect of the organic EL element according to the first embodiment, the content of the acceptor material in the second charge generation layer is 1% by mass or more, or 3% by mass or less. In one aspect of the organic EL element according to the first embodiment, when the second charge generation layer contains a second charge generation band material and an acceptor material, the content of the second charge generation band material in the second charge generation layer is 40% by mass or more, 45% by mass or more, 50% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more. In one aspect of the organic EL element according to the first embodiment, the content of the second charge generation band material in the second charge generation layer is 99.5% by mass or less, 99% by mass or less, or 97% by mass or less. The total content of the acceptor material and the second charge generation band material in the second charge generation layer is 100% by mass or less.
[0268] In one aspect of the organic EL element according to the first embodiment, the second charge generation band material is a hole transport band material (preferably, the second hole transport band material) described later. In one aspect of the organic EL element according to the first embodiment, the second charge generation band material contained in the second charge generation layer and the hole transport band material contained in a layer in the hole transport band (for example, the second hole transport layer) are the same compound as each other or different compounds.
[0269] <Electron transport band> In one aspect of the organic EL element according to the first embodiment, two or more light emitting units each independently include an electron transport band. In one aspect of the organic EL element according to the first embodiment, the first light emitting unit includes a first electron transport band, and the second light emitting unit includes a second electron transport band.
[0270] (First electron transport band) In one aspect of the organic EL element according to the first embodiment, the first electron transport band is disposed between the first light-emitting band and the second light-emitting unit.
[0271] In one aspect of the organic EL element according to the first embodiment, the first electron transport band is disposed between the first light-emitting band and the first charge generation band.
[0272] In one aspect of the organic EL element according to the first embodiment, the first electron transport band is disposed between the first light-emitting band and the first charge generation layer.
[0273] In one aspect of the organic EL element according to the first embodiment, the first electron transport band includes one or more layers.
[0274] In one aspect of the organic EL element according to the first embodiment, the first electron transport band is disposed between the first light-emitting band and the first charge generation layer, and the first electron transport band includes one or two or more layers.
[0275] In one aspect of the organic EL element according to the first embodiment, any of the one or two or more layers included in the first electron transport band is the low refractive index layer.
[0276] In one aspect of the organic EL element according to the first embodiment, the first electron transport band includes the first electron transport layer.
[0277] In one aspect of the organic EL element according to the first embodiment, the first electron transport layer is disposed between the first light-emitting band and the first charge generation layer. This first electron transport layer may be a hole barrier layer.
[0278] In one aspect of the organic EL element according to the first embodiment, the first charge generation layer and the first electron transport layer are in direct contact. In one aspect of the organic EL element according to the first embodiment, the first charge generation layer and the first electron transport layer do not have to be in direct contact.
[0279] In one aspect of the organic EL element according to the first embodiment, the first electron transport layer is a low refractive index layer. In one aspect of the organic EL element according to the first embodiment, when the organic EL element satisfies the condition (TDM1), one of at least two low refractive index layers that are in direct contact in the condition (TDM1) is the first electron transport layer.
[0280] In one aspect of the organic EL element according to the first embodiment, the first light emitting layer and the first electron transport layer are in direct contact.
[0281] In one aspect of the organic EL element according to the first embodiment, the first electron transport layer contains a first electron transport band material. In one aspect of the organic EL element according to the first embodiment, an organic material (low refractive index organic material) having a refractive index of 1.87 or less contained in the first electron transport layer is the first electron transport band material.
[0282] In one aspect of the organic EL element according to the first embodiment, the triplet energy T1(H1) of the first host material and the triplet energy T1(E1) of the first electron transport band material satisfy the following mathematical formula (Formula 1). T1(E1)>T1(H1) …(Formula 1)
[0283] In one aspect of the organic EL element according to the first embodiment, the first electron transport band includes two or more layers. In one aspect of the organic EL element according to the first embodiment, the first electron transport band includes a first hole barrier layer and a first electron transport layer.
[0284] In one aspect of the organic EL element according to the first embodiment, the first electron transport band further includes a first hole barrier layer between the first electron transport layer and the first light emitting band. In one aspect of the organic EL element according to the first embodiment, the first electron transport band includes, in order from the first light emitting band side, a first hole barrier layer and a first electron transport layer.
[0285] In one aspect of the organic EL element according to the first embodiment, the first electron transport band further includes a first hole barrier layer between the first electron transport layer and the first light-emitting layer. In one aspect of the organic EL element according to the first embodiment, the first light-emitting layer and the first hole barrier layer are in direct contact. In one aspect of the organic EL element according to the first embodiment, the first electron transport layer and the first hole barrier layer are in direct contact.
[0286] In one aspect of the organic EL element according to the first embodiment, the first hole barrier layer is a low refractive index layer. In one aspect of the organic EL element according to the first embodiment, when the organic EL element satisfies the condition (TDM1), one of at least two low refractive index layers in direct contact in the condition (TDM1) is the first hole barrier layer.
[0287] In one aspect of the organic EL element according to the first embodiment, the first hole barrier layer contains a first electron transport band material. The first electron transport band material contained in the first hole barrier layer and the first electron transport band material contained in the first electron transport layer may be the same compound or different compounds from each other. In one aspect of the organic EL element according to the first embodiment, the organic material (low refractive index organic material) having a refractive index of 1.87 or less contained in the first hole barrier layer is the first electron transport band material.
[0288] In one aspect of the organic EL element according to the first embodiment, when the first electron transport band includes the first electron transport layer, the triplet energy T1(H1) of the first host material and the triplet energy T1(E ET 1) of the first electron transport band material contained in the first electron transport layer satisfy the following relational expression (Equation 1A). T1(E ET 1)>T1(H1) …(Equation 1A)
[0289] In one aspect of the organic EL element according to the first embodiment, when the first electron transport band includes the first hole barrier layer, the triplet energy T1(H1) of the first host material and the triplet energy T1(E HB 1) of the first electron transport band material contained in the first hole barrier layer satisfy the relationship of the following formula (Formula 1B). T1(E HB 1)>T1(H1) …(Formula 1B)
[0290] In one aspect of the organic EL element according to the first embodiment, both the relationships of the above formula (Formula 1A) and formula (Formula 1B) are satisfied.
[0291] By satisfying the relationship of the above formula (Formula 1), (Formula 1A) or (Formula 1B), the diffusion of triplet excitons into the first electron transport band and the first charge generation band is suppressed, and the triplet excitons of the host material are efficiently converted into singlet excitons in the light-emitting layer. Then, the singlet excitons move onto the dopant material (luminescent compound) to cause optical energy deactivation. Therefore, the TTF efficiency in the first light-emitting layer is improved, and an improvement in the luminous efficiency can be expected.
[0292] Conventionally, as a technique for improving the luminous efficiency of an organic electroluminescence element, Triplet-Triplet-Annihilation (sometimes referred to as TTA) is known. TTA is a mechanism in which triplet excitons collide with each other to generate singlet excitons. Note that the TTA mechanism is sometimes referred to as the TTF mechanism. TTF is an abbreviation for Triplet-Triplet Fusion.
[0293] Explain the TTF phenomenon. Holes injected from the anode and electrons injected from the cathode recombine in the light-emitting layer to generate excitons. As is conventionally known, the spin state has a ratio of 25% singlet excitons and 75% triplet excitons. In a conventionally known fluorescent element, light is emitted when 25% of the singlet excitons relax to the ground state, while the remaining 75% of the triplet excitons return to the ground state through a thermal deactivation process without emitting light. Therefore, the theoretical limit value of the internal quantum efficiency of a conventional fluorescent element has been said to be 25%. On the other hand, the behavior of triplet excitons generated inside an organic substance has been theoretically investigated. According to S.M. Bachilo et al. (J. Phys. Chem. A, 104, 7711 (2000)), assuming that higher-order excitons such as quintets immediately return to triplets, when the density of triplet excitons (hereinafter referred to as 3 A * as described) increases, triplet excitons collide with each other and a reaction as shown in the following formula occurs. Here, 1 A represents the ground state, 1 A * represents the lowest excited singlet exciton. 3 A * + 3 A * →(4 / 9) 1 A+(1 / 9) 1 A * +(13 / 9) 3 A * That is, 5 3 A * →4 1 A + 1A *As a result, it is predicted that 1 / 5, i.e., 20%, of the initially generated 75% triplet excitons will be converted into singlet excitons. Therefore, the singlet excitons contributing as light are 40% obtained by adding 75%×(1 / 5)=15% to the initially generated 25%. At this time, the luminescence ratio (TTF ratio) derived from TTF in the total luminescence intensity is 15 / 40, that is, 37.5%. Also, assuming that the initially generated 75% triplet excitons collide with each other to generate singlet excitons (one singlet exciton is generated from two triplet excitons), a very high internal quantum efficiency of 62.5% is obtained by adding 75%×(1 / 2)=37.5% to the initially generated 25% singlet excitons. At this time, the TTF ratio is 37.5 / 62.5 = 60%.
[0294] (Triplet energy T1) As a method for measuring the triplet energy T1, the following method can be mentioned. The compound to be measured is dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to a concentration of 10 -5 mol / L or more and 10 -4 mol / L or less to prepare a solution, and this solution is placed in a quartz cell to obtain a measurement sample. For this measurement sample, a phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) is measured at a low temperature (77 [K]). A tangent is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the energy amount calculated from the following conversion formula (F1) based on the wavelength value λ edge [nm] of the intersection of the tangent and the horizontal axis is defined as the triplet energy T1. Conversion formula (F1): T1 [eV] = 1239.85 / λ edge
[0295] The tangent to the rising edge on the short-wavelength side of the phosphorescence spectrum is drawn as follows. When moving along the spectrum curve from the short-wavelength side of the phosphorescence spectrum to the maximum value on the shortest-wavelength side among the maximum values of the spectrum, the tangent at each point on the curve is considered in the long-wavelength direction. As the curve rises (i.e., as the vertical axis increases), the slope of this tangent increases. The tangent drawn at the point where the value of this slope reaches its maximum (i.e., the tangent at the inflection point) is taken as the tangent to the rising edge on the short-wavelength side of the phosphorescence spectrum. Note that the maximum points having a peak intensity of 15% or less of the maximum peak intensity of the spectrum are not included in the maximum value on the shortest-wavelength side described above, and the tangent drawn at the point closest to the maximum value on the shortest-wavelength side where the value of the slope reaches its maximum is taken as the tangent to the rising edge on the short-wavelength side of the phosphorescence spectrum. For the measurement of phosphorescence, an F-4500 type spectrofluorometer main body manufactured by Hitachi High-Technologies Corporation can be used. Note that the measuring device is not limited to this, and it may be measured by combining a cooling device, a cryogenic container, an excitation light source, and a light receiving device.
[0296] In one aspect of the organic EL element according to the first embodiment, the refractive index of the first electron transport band material is 1.83 or less.
[0297] In one aspect of the organic EL element according to the first embodiment, the refractive index of the first electron transport band material is 1.83 or less, and the refractive index of the organic material (the first charge generation band material) contained in the first charge generation layer is 1.83 or less.
[0298] In one aspect of the organic EL element according to the first embodiment, the first electron transport band material and the first charge generation band material are different from each other.
[0299] In one aspect of the organic EL element according to the first embodiment, the first electron transport band material and the second charge generation band material are different from each other.
[0300] In one aspect of the organic EL element according to the first embodiment, the refractive index of the first electron transport band material is 1.83 or less, the refractive index of the organic material (first charge generation band material) contained in the first charge generation layer is 1.83 or less, and the refractive index of the second charge generation band material is 1.83 or less.
[0301] In one aspect of the organic EL element according to the first embodiment, the refractive index of the first electron transport band material is smaller than the refractive index of the first charge generation band material. In one aspect of the organic EL element according to the first embodiment, the refractive index of the first charge generation band material is greater than 1.70, and the refractive index of the first electron transport band material is 1.70 or less.
[0302] (Second electron transport band) In one aspect of the organic EL element according to the first embodiment, the second electron transport band is disposed between the second light emission band and the cathode. In one aspect of the organic EL element according to the first embodiment, the second electron transport band includes one or more layers. In one aspect of the organic EL element according to the first embodiment, the second electron transport band includes a second electron transport layer.
[0303] In one aspect of the organic EL element according to the first embodiment, the second electron transport band includes two or more layers. In one aspect of the organic EL element according to the first embodiment, the second electron transport band includes a second electron transport layer and a second electron injection layer. In one aspect of the organic EL element according to the first embodiment, the second electron transport layer is in direct contact with the second light emitting layer in the second light emission band.
[0304] In one aspect of the organic EL element according to the first embodiment, the second electron transport band includes three or more layers. In one aspect of the organic EL element according to the first embodiment, the second electron transport band includes three layers, and these three layers are a second hole barrier layer, a second electron transport layer, and a second electron injection layer. In one aspect of the organic EL element according to the first embodiment, the second electron transport band includes, in order from the second light emission band side, a second hole barrier layer, a second electron transport layer, and a second electron injection layer.
[0305] In one aspect of the organic EL element according to the first embodiment, the second hole barrier layer is in direct contact with the second light emitting layer in the second light emission band. In one aspect of the organic EL element according to the first embodiment, the second hole barrier layer and the second electron transport layer are in direct contact with each other. In one aspect of the organic EL element according to the first embodiment, the second electron transport layer and the second electron injection layer are in direct contact with each other. In one aspect of the organic EL element according to the first embodiment, the second electron injection layer and the cathode are in direct contact with each other.
[0306] In one aspect of the organic EL element according to the first embodiment, the second electron transport band contains a second electron transport band material.
[0307] (Electron transport band material) In the organic EL element according to the first embodiment, the material contained in the electron transport band is referred to as an electron transport band material. The electron transport band material is, for example, the aforementioned first electron transport band material and second electron transport band material. The electron transport band material can also be used as the first charge generation band material.
[0308] In one aspect of the organic EL element according to the first embodiment, among the layers included in the first electron transport band, at least one of the layers contains, as the first electron transport band material, a compound represented by the following formulas (E1), (E2), (E3), (E4), (E41), (E42), (E43), (E44), (E5), (E61), (E62), or (E7).
[0309] In one aspect of the organic EL element according to the first embodiment, among the layers included in the second electron transport band, at least one of the layers contains, as the second electron transport band material, a compound represented by the following formula (E1), (E2), (E3), (E4), (E41), (E42), (E43), (E44), (E5), (E61), (E62), or (E7).
[0310] In one aspect of the organic EL element according to the first embodiment, the first charge generation layer contains, as the first charge generation band material, a compound represented by the following formula (E1), (E2), (E3), (E4), (E41), (E42), (E43), (E44), (E5), (E61), (E62), or (E7).
[0311] In one aspect of the organic EL element according to the first embodiment, the electron transport band material (the first electron transport band material or the second electron transport band material) is a compound represented by the following formula (E1).
[0312]
Chemical formula
[0313] (In the formula (E1), R 101 ~R 110 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by -O-(R 904 ) group represented by -S-(R 905a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms -C(=O)R 801 a group represented by -COOR 802 a group represented by a halogen atom a cyano group a nitro group a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, or a group represented by the formula (E11), provided that R 101 ~R 110 at least one of which is a group represented by the formula (E11), when a plurality of groups represented by the formula (E11) are present, the plurality of groups represented by the formula (E11) are the same as or different from each other, L 101 is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, Ar 101 is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, mx is 0, 1, 2, 3, 4 or 5, provided that when mx is 0, -(L 101 )0- is a single bond, L 101 when two or more L 101 are present, the two or more L Ar 101 when two or more Ar 101 are present, the two or more Ar * in the formula (E11) indicates the bonding position with the pyrene ring in the formula (E1).) (In the formula (E1), R 901 , R 902 , R903 , R 904 , R 905 , R 801 and R 802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, and R 901 when there are a plurality of R's, the plurality of R's 901 are the same as or different from each other, R 902 when there are a plurality of R's, the plurality of R's 902 are the same as or different from each other, R 903 when there are a plurality of R's, the plurality of R's 903 are the same as or different from each other, R 904 when there are a plurality of R's, the plurality of R's 904 are the same as or different from each other, R 905 when there are a plurality of R's, the plurality of R's 905 are the same as or different from each other, R 801 when there are a plurality of R's, the plurality of R's 801 are the same as or different from each other, R 802 when there are a plurality of R's, the plurality of R's 802 are the same as or different from each other.)
[0314] In one aspect of the organic EL element according to the first embodiment, the electron transport band material (the first electron transport band material or the second electron transport band material) is a compound represented by the following formula (E2).
[0315] [Chemical formula]
[0316] (In the formula (E2), R 201 ~R 212 Among one or more sets of two or more adjacent ones, Combine with each other to form a substituted or unsubstituted monocyclic ring, Combine with each other to form a substituted or unsubstituted condensed ring, or Do not combine with each other, Do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring, and R 201 ~R 212 are each independently, A hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, A substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 )-represented group, -COOR 802 )-represented group, A halogen atom, A cyano group, A nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, or A group represented by the formula (E21), provided that R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring,201 ~R 212 At least one of them is a group represented by the formula (E21), When there are a plurality of groups represented by the formula (E21), the plurality of groups represented by the formula (E21) are the same as or different from each other, L 201 is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, ma is 0, 1, 2, 3, 4 or 5, provided that when ma is 0, -(L 201 )0- is a single bond, L 201 When two or more L are present, the two or more L 201 are the same as or different from each other, Ar 201 is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, Ar 201 When two or more Ar are present, the two or more Ar 201 are the same as or different from each other, The * in the formula (E21) indicates the bonding position with the benz[a]anthracene ring in the formula (E2). However, when one or more of the pairs consisting of two or more adjacent ones among R 201 ~R 212 form the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted condensed ring, the * in the formula (E21) indicates the bonding position with the mother skeleton of the formed ring structure.) (In the formula (E2), R 901 , R 902 , R 903 , R 904 , R 905 , R 801 and R 802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A cycloalkyl group having 3 to 50 ring-forming carbon atoms, which may or may not be substituted, an aryl group having 6 to 50 ring-forming carbon atoms, which may or may not be substituted, or a heterocyclic group having 5 to 50 ring-forming atoms, which may or may not be substituted, R 901 When a plurality of R's exist, the plurality of R's 901 are the same as or different from each other, R 902 When a plurality of R's exist, the plurality of R's 902 are the same as or different from each other, R 903 When a plurality of R's exist, the plurality of R's 903 are the same as or different from each other, R 904 When a plurality of R's exist, the plurality of R's 904 are the same as or different from each other, R 905 When a plurality of R's exist, the plurality of R's 905 are the same as or different from each other, R 801 When a plurality of R's exist, the plurality of R's 801 are the same as or different from each other, R 802 When a plurality of R's exist, the plurality of R's 802 are the same as or different from each other.)
[0317] In one aspect of the organic EL element according to the first embodiment, the electron transport band material (the first electron transport band material or the second electron transport band material) is a compound represented by the following formula (E3).
[0318]
Chemical formula
[0319] (In the above formula (E3), R 307 and R 312 One of them represents a single bond with *1, and R 307 and R 312 The other of them represents a single bond with *2, R301 ~R 306 , R 308 ~R 311 , and R 322 ~R 325 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R 321 teeth, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, Ar 31 teeth, Hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms; a substituted or unsubstituted oxygen-containing heterocyclic group having 5 to 18 ring atoms, or a substituted or unsubstituted sulfur-containing heterocyclic group having 5 to 18 ring atoms, L 31 and L 32 are each independently a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms, or A divalent heterocyclic group having 5 to 14 ring-forming atoms, which may be substituted or unsubstituted, n1 is 0, 1, 2 or 3, n2 is 0, 1, 2 or 3, When n1 is 0, -(L 31 )0- is a single bond, When n1 is 2 or more, two or more L 31 are connected in series with each other, When n1 is 2 or more, two or more L 31 are the same as or different from each other, When n2 is 0, -(L 32 )0- is a single bond, When n2 is 2 or more, two or more L 32 are connected in series with each other, When n2 is 2 or more, two or more L 32 are the same as or different from each other.) (In the formula (E3), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901 When there are a plurality of R 901 are the same as or different from each other, R 902 When there are a plurality of R 902 are the same as or different from each other, R 903 When there are a plurality of R 903 are the same as or different from each other, R 904 When there are a plurality of R904 are the same as or different from each other, R 905 when there are a plurality of R, the plurality of R 905 are the same as or different from each other, R 906 when there are a plurality of R, the plurality of R 906 are the same as or different from each other, R 907 when there are a plurality of R, the plurality of R 907 are the same as or different from each other.)
[0320] In one aspect of the organic EL element according to the first embodiment, the electron transport band material (the first electron transport band material or the second electron transport band material) is a compound represented by the following formula (E4).
[0321]
Chemical formula
[0322] (In the formula (E4), X2 is N or C-(L 42 )m2-(Ar 42 )m 21 wherein, X4 is N or C-(L 44 )m4-(Ar 44 )m 41 wherein, X5 is N or C-(L 45 )m5-(Ar 45 )m 51 wherein, X6 is N or C-(L 46 )m6-(Ar 46 )m 61 wherein, at least one of X2, X4, X5 and X6 is a nitrogen atom, L 41 ~L 46 are each independently, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, m1 is 0, 1, 2 or 3; when m1 is 0, -(L 41 )0- is a single bond, m2 is 0, 1, 2 or 3; when m2 is 0, -(L 42 )0- is a single bond, m3 is 0, 1, 2 or 3; when m3 is 0, -(L 43 )0- is a single bond, m4 is 0, 1, 2 or 3; when m4 is 0, -(L 44 )0- is a single bond, m5 is 0, 1, 2 or 3; when m5 is 0, -(L 45 )0- is a single bond, m6 is 0, 1, 2 or 3; when m6 is 0, -(L 46 )0- is a single bond, m 11 is 1, 2, 3 or 4, m 21 is 1, 2, 3 or 4, m 31 is 1, 2, 3 or 4, m 41 is 1, 2, 3 or 4, m 51 is 1, 2, 3 or 4, m 61 is 1, 2, 3 or 4, Ar 41 ~Ar 46 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 911 )(R 912 )(R 913 ) group represented by, -O-(R914 a group represented by -S-(R 915 a group represented by -N(R 916 )(R 917 a group represented by -P(=O)(R 918 )(R 919 a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms -C(=O)R 920 a group represented by -COOR 921 a group represented by a halogen atom a cyano group a nitro group a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, provided that however, at least one of Ar 41 ~Ar 46 is a substituted or unsubstituted aryl group having 13 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 13 to 50 ring-forming atoms.) (In the above formula (E4), R 911 , R 912 , R 913 , R 914 , R 915 , R 916 , R 917 , R 918 , R 919 , R 920 and R 921 are each independently a hydrogen atom a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, provided that when there are a plurality of R 911 s, the plurality of R911 are the same as or different from each other, R 912 when there are a plurality of R's, the plurality of R's 912 are the same as or different from each other, R 913 when there are a plurality of R's, the plurality of R's 913 are the same as or different from each other, R 914 when there are a plurality of R's, the plurality of R's 914 are the same as or different from each other, R 915 when there are a plurality of R's, the plurality of R's 915 are the same as or different from each other, R 916 when there are a plurality of R's, the plurality of R's 916 are the same as or different from each other, R 917 when there are a plurality of R's, the plurality of R's 917 are the same as or different from each other, R 918 when there are a plurality of R's, the plurality of R's 918 are the same as or different from each other, R 919 when there are a plurality of R's, the plurality of R's 919 are the same as or different from each other, R 920 when there are a plurality of R's, the plurality of R's 920 are the same as or different from each other, R 921 when there are a plurality of R's, the plurality of R's 921 are the same as or different from each other.)
[0323] In one aspect of the organic EL element according to the first embodiment, the electron transport band material (the first electron transport band material or the second electron transport band material) is a compound represented by the following formula (E41).
[0324]
Chemical formula
[0325] (In the formula (E41), L 41 、L 43 、and L 45 are respectively synonymous with L 41 、L 43 、and L 45 in the formula (E4), and m1, m3, and m5 are respectively synonymous with m1, m3, and m5 in the formula (E4). R A and R B One of them represents a single bond with *3, and R A or R B that is not a single bond with *3 is a hydrogen atom or a substituent S. In the case of the substituent S as R A or R B , when it is "substituted or unsubstituted", in the case of "substituted", it has one or more substituents T. R 401 ~R 409 are each independently a hydrogen atom or a substituent R. The substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a group represented by -Si(R 911 )(R 912 )(R 913 ), a group represented by -O-(R 914 ), a group represented by -S-(R 915 ), a group represented by -N(R 916 )(R 917 ), a group represented by -P(=O)(R 918 )(R 919 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and selected from the group consisting of substituted or unsubstituted heterocyclic groups having 5 to 50 ring-forming atoms, when two or more substituents R are present, the two or more substituents R are the same as or different from each other, R 410 is a hydrogen atom, R 401 ~R 409 and R that is not a single bond with *3 A and R B among two or more adjacent ones do not bond to each other, X6 is a nitrogen atom or C-Ar 46 where Ar 46 is a hydrogen atom or a substituent V, Ar 41 and Ar 45 at least one of which is a substituent X, and in the case of "substituted or unsubstituted" in the substituent X as Ar 41 and Ar 45 when it is "substituted", it has one or more substituents U, Ar that is not a substituent X 41 and Ar 45 are a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms and not containing a nitrogen atom, the substituent X is a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benzoanthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted triphenylenyl group, A substituted or unsubstituted benzotriphenylenyl group, A substituted or unsubstituted tetracenyl group, A substituted or unsubstituted pentacenyl group, A substituted or unsubstituted fluorenyl group, A substituted or unsubstituted 9,9'-spirobifluorenyl group, A substituted or unsubstituted benzofluorenyl group, A substituted or unsubstituted dibenzofluorenyl group, A substituted or unsubstituted fluoranthenyl group, A substituted or unsubstituted benzofluoranthenyl group, A substituted or unsubstituted perylenyl group, A heterocyclic group represented by the following formula (E411), and A group selected from the group consisting of heterocyclic groups represented by the following formula (E412), When two or more substituents X are present, the two or more substituents X are the same as or different from each other, When two or more substituents U are present, the two or more substituents U are the same as or different from each other, R A Or R B As the substituent S, R A Or R B In the case of "substituted or unsubstituted", the substituent T, Ar 41 And Ar 45 In the case of "substituted or unsubstituted", the substituent U, and Ar 46 As the substituent V are each independently A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 911 )(R 912 )(R 913 ) group represented by -O-(R 914 ) group represented by -S-(R 915 ) group represented by -N(R 916 )(R 917 ) group represented by -P(=O)(R 918 )(R 919 ) group represented by A halogen atom, a cyano group, a nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, selected from the group consisting of, When two or more substituents T are present, the two or more substituents T may be the same as or different from each other.)
[0326]
Chemical formula
[0327] (In the above formula (E411), X 41 is N(R 429 ), an oxygen atom, or a sulfur atom.) R 421 ~R 429 Any one of them represents a single bond with L 41 or L 45 ; R 421 ~R 429 One or more sets of two or more adjacent ones among them Combine with each other to form a substituted or unsubstituted monocyclic ring, Combine with each other to form a substituted or unsubstituted condensed ring, or Do not combine with each other, L 41 or L 45 do not represent a single bond with, do not form the substituted or unsubstituted monocyclic ring, and do not form the substituted or unsubstituted condensed ring, and R 421 ~R 429 are each independently A hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 911 )(R 912 )(R 913 )-represented group, -O-(R 914 )-represented group, -S-(R 915 )-represented group, -N(R 916 )(R 917 )-represented group, -P(=O)(R 918 )(R 919 )-represented group, A halogen atom, a cyano group, a nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms and not containing a nitrogen atom, selected from the group consisting of.) (In the formula (E412), X 42 is N(R 437 ), an oxygen atom, or a sulfur atom. R 431 ~R 437 Any one of them is a single bond with L 41 or L 45 represents, R 431 ~R 437 One or more sets of two or more adjacent ones among them are Bonded to each other to form a substituted or unsubstituted monocyclic ring, Bonded to each other to form a substituted or unsubstituted condensed ring, or Not bonded to each other, L 41 or L 45 Do not represent a single bond with, do not form the substituted or unsubstituted monocyclic ring, and do not form the substituted or unsubstituted condensed ring R 431 ~R 437 are each independently A hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 911 )(R 912 )(R 913 )-represented group, -O-(R 914 )-represented group, -S-(R 915 )-represented group, -N(R 916 )(R 917 )-represented group, -P(=O)(R 918 )(R 919 )-represented group, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms and not containing a nitrogen atom, selected from the group consisting of.) (In the formulas (E41), (E411) and (E412), R 911 ~R 919 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms and not containing a nitrogen atom, and R 911 when there are a plurality of R 911 are the same as or different from each other, R 912 when there are a plurality of R 912 are the same as or different from each other, R 913When there are a plurality of R's, the plurality of R's 913 are the same as or different from each other, R 914 When there are a plurality of R's, the plurality of R's 914 are the same as or different from each other, R 915 When there are a plurality of R's, the plurality of R's 915 are the same as or different from each other, R 916 When there are a plurality of R's, the plurality of R's 916 are the same as or different from each other, R 917 When there are a plurality of R's, the plurality of R's 917 are the same as or different from each other, R 918 When there are a plurality of R's, the plurality of R's 918 are the same as or different from each other, R 919 When there are a plurality of R's, the plurality of R's 919 are the same as or different from each other.)
[0328] In one aspect of the organic EL element according to the first embodiment, the electron transport band material (the first electron transport band material or the second electron transport band material) is a compound represented by the following formula (E42).
[0329]
Chemical formula
[0330] (In the formula (E42), X2, X4, X6, L 41 , L 43 , L 45 , Ar 41 and Ar 45 are respectively synonymous with X2, X4, X6, L 41 , L 43 , L 45 , Ar 41 and Ar 45 in the formula (E1), and m1, m3, m 31 and m5 are respectively m1, m3, m in the formula (E1),31 and synonymous with m5, R 4001 ~R 4008 one or more sets of two or more adjacent ones among them are joined to each other to form an unsubstituted or substituted monocyclic ring, joined to each other to form an unsubstituted or substituted fused ring, or not joined to each other, R 4009 and R that does not form the unsubstituted or substituted monocyclic ring and does not form the unsubstituted or substituted fused ring 4001 ~R 4008 each independently is a hydrogen atom, an unsubstituted or substituted alkyl group having 1 to 50 carbon atoms, an unsubstituted or substituted haloalkyl group having 1 to 50 carbon atoms, an unsubstituted or substituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted or substituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted or substituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 911 )(R 912 )(R 913 ) group represented by -O-(R 914 ) group represented by -S-(R 915 ) group represented by an unsubstituted or substituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 920 ) group represented by -COOR 921 ) group represented by a halogen atom, a cyano group, a nitro group, an unsubstituted or substituted aryl group having 6 to 50 ring-forming carbon atoms, or an unsubstituted or substituted heterocyclic group having 5 to 50 ring-forming atoms, provided that R 4009 and R that does not form the unsubstituted or substituted monocyclic ring and does not form the unsubstituted or substituted fused ring4001 ~R 4008 At least one of them is a single bond with *4, *4 indicates the bonding position with the carbazole ring in the formula (E42). However, R 4001 ~R 4008 When one or more sets of two or more adjacent ones among them form the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted condensed ring, *4 in the formula (E42) indicates the bonding position with the mother skeleton of the formed ring structure.) (In the formula (E42), R 911 , R 912 , R 913 , R 914 , R 915 , R 920 and R 921 are respectively synonymous with R 911 , R 912 , R 913 , R 914 , R 915 , R 920 and R 921 in the formula (E4).)
[0331] In one aspect of the organic EL element according to the first embodiment, the electron transport band material (the first electron transport band material or the second electron transport band material) is a compound represented by the following formula (E43).
[0332]
Chemical formula
[0333] (In the formula (E43), X2, X4, X6, L 41 , L 43 , L 45 , Ar 41 and Ar 45 are respectively synonymous with X2, X4, X6, L 41 , L 43 , L 45 , Ar 41 and Ar 45 in the formula (E1), and m1, m3, m 31and m5 are respectively the same as m1, m3, and m in the formula (E1), 31 and are synonymous with m5, R 5001 ~R 5008 One or more sets of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted condensed ring, and R 5001 ~R 5008 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 911 )(R 912 )(R 913 )-represented group, -O-(R 914 )-represented group, -S-(R 915 )-represented group, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 920 )-represented group, -COOR 921 )-represented group, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, provided that R which neither forms the substituted or unsubstituted monocyclic ring nor forms the substituted or unsubstituted condensed ring,5001 ~R 5008 At least one of them is a single bond with *5, *5 indicates the bonding position with the dibenzofuran ring in the formula (E43). However, R 5001 ~R 5008 When one or more sets of two or more adjacent ones among them form the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted condensed ring, *5 in the formula (E43) indicates the bonding position with the parent skeleton of the formed ring structure.) (In the formula (E43), R 911 , R 912 , R 913 , R 914 , R 915 , R 920 and R 921 are respectively synonymous with R 911 , R 912 , R 913 , R 914 , R 915 , R 920 and R 921 in the formula (E4).)
[0334] In one aspect of the organic EL element according to the first embodiment, the electron transport band material (the first electron transport band material or the second electron transport band material) is a compound represented by the following formula (E44).
[0335]
Chemical formula
[0336] (In the formula (E44), X2, X4, X6, L 41 , L 43 , L 45 , Ar 41 and Ar 45 are respectively synonymous with X2, X4, X6, L 41 , L 43 , L 45 , Ar 41 and Ar 45 in the formula (E1), and m1, m3, m 31and m5 are respectively m1, m3, m in the formula (E1) 31 and have the same meaning as m5, R 6009 and R 6010 the group consisting of are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other, R 6001 ~R 6008 one or more groups consisting of two or more adjacent ones among are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other, neither form the substituted or unsubstituted monocyclic ring nor form the substituted or unsubstituted condensed ring, and R 5001 ~R 5010 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 911 )(R 912 )(R 913 ) group represented by -O-(R 914 ) group represented by -S-(R 915 ) group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 920 group represented by -COOR 921 group represented by a halogen atom, a cyano group, A nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, provided that R which does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 6001 ~R 6010 at least one of them is a single bond with *6, *6 indicates the bonding position with the dibenzofuran ring in the formula (E44). However, when one or more of the groups consisting of two or more adjacent ones among R 6001 ~R 6010 form the above-mentioned substituted or unsubstituted monocyclic ring or the above-mentioned substituted or unsubstituted condensed ring, *6 in the formula (E44) indicates the bonding position with the mother skeleton of the formed ring structure.) (In the formula (E44), R 911 , R 912 , R 913 , R 914 , R 915 , R 920 and R 921 are respectively synonymous with R 911 , R 912 , R 913 , R 914 , R 915 , R 920 and R 921 in the formula (E4).)
[0337] In one aspect of the organic EL element according to the first embodiment, the electron transport band material (the first electron transport band material or the second electron transport band material) is a compound represented by the following formula (E5).
[0338]
Chemical formula
[0339] (In the formula (E5), one or more of the groups consisting of two or more adjacent ones among R 501 ~R 508 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or Combine with each other to form a substituted or unsubstituted condensed ring, or Do not combine with each other, R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 501 ~R 508 Each independently is A hydrogen atom, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, A substituted or unsubstituted pyridyl group, A substituted or unsubstituted quinolyl group, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -O-(R 904 ) group represented by -S-(R 905 ) group represented by A substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, A halogen atom, a cyano group, a nitro group, a carboxy group, -N(R 905N )(R 906N ) group represented by, or The group represented by the formula (E51), When there are a plurality of groups represented by the formula (E51), the plurality of groups represented by the formula (E51) are the same as or different from each other, L 501 Is A single bond, A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, HAr 501 Is A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, mb is 1, 2, 3 or 4, When mb is 2, 3, or 4, two or more Ls 501 are identical to or different from each other, two or more HArs 501 are identical to or different from each other, The * in the formula (E51) indicates the bonding position with the phenanthroline ring in the formula (E5). However, when one or more of the groups consisting of two or more adjacent ones among R 501 ~R 508 form the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted condensed ring, the * in the formula (E51) indicates the bonding position with the parent skeleton of the formed ring structure.) (In the formula (E5), R 904 and R 905 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, When there are a plurality of Rs 904 , the plurality of Rs 904 are identical to or different from each other, When there are a plurality of Rs 905 , the plurality of Rs 905 are identical to or different from each other, R 905N and R 906N are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, When there are a plurality of Rs 905N , the plurality of Rs 905N are identical to or different from each other, When there are a plurality of Rs 906N , the plurality of Rs 906N are identical to or different from each other.)
[0340] In one aspect of the organic EL element according to the first embodiment, at least one of R 501 ~R 508 is a group represented by the formula (E51), and the group represented by the formula (E51) is a group represented by any of the following formulas (E511) to (E515).
[0341]
Chemical formula
[0342] (In the formula (E511), any one of R 511 , R 512 , R 513 , R 514 and R 515 represents a single bond with L 501 . In the formula (E512), any one of R 516 , R 517 , R 518 and R 519 represents a single bond with L 501 . In the formula (E513), any one of R 520 , R 521 and R 522 represents a single bond with L 501 . In the formula (E514), any one of R 523 , R 524 , R 525 and R 526 represents a single bond with L 501 . In the formula (E515), any one of R 527 , R 528 , R 529 and R 530 represents a single bond with L 501 . One or more sets of two or more adjacent ones among R 511 ~R 530 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or form a polycyclic ring having a condensed ring structure with a benzene ring or a heterocyclic ring, or Combined with each other to form a substituted or unsubstituted condensed ring, or not combined with each other, L 501 does not represent a single bond with, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted condensed ring, and R 511 ~R 530 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -O-(R 904 )-represented group, -S-(R 905 )-represented group, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a carboxy group, or -N(R 905N )(R 906N )-represented group, and R 904 , R 905 , R 905N and R 906N are each synonymous with R 904 , R 905 , R 905N and R 906N in the formula (E5), and * represents a bonding position.)
[0343] In one aspect of the organic EL element according to the first embodiment, R 501 ~R 508At least one of them is a group represented by the formula (E51), and the group represented by the formula (E51) is a group represented by any one of the following formulas (E516) to (E529).
[0344]
Chemical formula
[0345]
Chemical formula
[0346] (In the formulas (E516) to (E525), R E any one of them represents a single bond with L 501 and a plurality of R E one or more sets of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or do not bond to each other, L 501 do not represent a single bond with, do not form the substituted or unsubstituted monocyclic ring, and do not form the substituted or unsubstituted condensed ring R E are each independently, in the formulas (E511) to (E515), L 501 do not represent a single bond with, do not form the substituted or unsubstituted monocyclic ring, and do not form the substituted or unsubstituted condensed ring R 511 ~R 530 are synonymous with, a plurality of R E are the same as or different from each other, and * represents the bonding position.)
[0347] In one aspect of the organic EL element according to the first embodiment, the electron transport band material (the first electron transport band material or the second electron transport band material) is a compound represented by the following formula (E61) or (E62).
[0348] [Chemical]
[0349] (In the above formulas (E61) and (E62), Cz is, independently of each other, any carbazolyl group or indolyl group represented by any formula selected from the group consisting of the following formulas (E63), (E64), (E65), (E66), (E67), and (E68), L6 is, independently of each other, a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, pa is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, pb is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, When a plurality of L6 are present, the plurality of L6 may be the same as or different from each other, When a plurality of Cz are present, the plurality of Cz may be the same as or different from each other, FA is, independently of each other, a substituted or unsubstituted condensed ring group having 6 to 50 ring-forming carbon atoms, provided that FA is not an unsubstituted carbazolyl group.)
[0350] [Chemical]
[0351] (In the above formulas (E63), (E64), (E65), (E66), (E67), and (E68), Z6 is, independently of each other, a single bond, -C(R 601 )(R 602 )-, -Si(R 603 )(R 604 )-, -O-, -CO-, or -N(R 605 )-, R 601 、R 602 、R 603 、R 604and R 605 each independently is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Ring E each independently is a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted nitrogen atom-containing non-aromatic heterocyclic ring having 3 to 20 ring-forming atoms, a substituted or unsubstituted aromatic hydrocarbon ring having 4 to 50 ring-forming carbon atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 4 to 50 ring-forming atoms, a is 3, b each independently is 0, 1, 2, 3 or 4, c is 4, d is 2, e is 1, One or more of the groups consisting of two or more adjacent ones among the plurality of R6s are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other, R6s that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring each independently are a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, -O-(R 904 ) group represented by -S-(R 905 ) group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a carboxy group, a halogen atom, a cyano group or a nitro group, A plurality of Rs 601 are either identical to or different from each other, A plurality of Rs 602 are either identical to or different from each other, A plurality of Rs 603 are either identical to or different from each other, A plurality of Rs 604 are either identical to or different from each other, A plurality of Rs 605 are either identical to or different from each other, A plurality of R6s are either identical to or different from each other. * represents a bonding position.) (In the compound represented by the formula (E61) or (E62), R 904 and R 905 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 904 When there are a plurality of Rs, the plurality of Rs 904 are either identical to or different from each other, R 905 When there are a plurality of Rs, the plurality of Rs 905 are either identical to or different from each other.)
[0352] In one aspect of the organic EL element according to the first embodiment, the group represented by the formula (E63) is a group represented by any one of the formulas (E631), (E632), (E633), and (E634) selected from the group consisting of the following.
[0353]
Chemical formula
[0354]
Chemical formula
[0355] (In the formulas (E631), (E632), (E633), and (E634), R6 and a are respectively synonymous with R6 and a in the formula (E63), bx is 4, by is 3, R 61 ~R 68 is respectively independently synonymous with R6 in the formula (E63), and a plurality of R6s are identical to or different from each other, and * represents the bonding position.)
[0356] In one aspect of the organic EL element according to the first embodiment, the group represented by the formula (E65) is a group represented by any one of the formulas (E651), (E652), (E653), and (E654) selected from the group consisting of the following.
[0357]
Chemical formula
[0358]
Chemical formula
[0359] (In the formulas (E651), (E652), (E653), and (E654), R6 and c are respectively synonymous with R6 and c in the formula (E65), bx is 4, by is 3, R 61 ~R 68 is respectively independently synonymous with R6 in the formula (E65), and a plurality of R6s are identical to or different from each other, and * represents the bonding position.)
[0360] In one aspect of the organic EL element according to the first embodiment, the electron transport band material (the first electron transport band material or the second electron transport band material) is a compound represented by the following formula (E7).
[0361]
Chemical formula
[0362] (In the formula (E7), R 701 ~R 710 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by, -O-(R 904 ) group represented by, -S-(R 905 ) group represented by, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 group represented by, -COOR 802 group represented by, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, or a group represented by the formula (E71), provided that at least one of R 701 ~R 710 is a group represented by the formula (E71), when there are a plurality of groups represented by the formula (E71), the plurality of groups represented by the formula (E71) are the same as or different from each other, L 701 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted, Ar 701 is an aryl group having 6 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, or a heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted, mx7 is 0, 1, 2, 3, 4 or 5, provided that when mx7 is 0, -(L 701 )0- is a single bond, L 701 when two or more L 701 are present, the two or more L Ar 701 when two or more Ar 701 are present, the two or more Ar * in the formula (E71) indicates the bonding position with the ring represented by the formula (E7).) (In the compound represented by the formula (E7), R 901 , R 902 , R 903 , R 904 , R 905 , R 801 and R 802 are each independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, which may be substituted or unsubstituted, a cycloalkyl group having 3 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, an aryl group having 6 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, or a heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted, R 901 when a plurality of R 901 are present, the plurality of R R 902 when a plurality of R 902 are present, the plurality of R R 903 when a plurality of R 903 are present, the plurality of R R 904When there are a plurality of R's, the plurality of R's 904 are the same as or different from each other, R 905 When there are a plurality of R's, the plurality of R's 905 are the same as or different from each other, R 801 When there are a plurality of R's, the plurality of R's 801 are the same as or different from each other, R 802 When there are a plurality of R's, the plurality of R's 802 are the same as or different from each other.)
[0363] In one aspect of the organic EL element according to the first embodiment, the first charge generation band material is not a compound having an anthracene skeleton.
[0364] In one aspect of the organic EL element according to the first embodiment, when the first charge generation band material is a compound represented by the formula (E5) (a compound having a phenanthroline skeleton), the first charge generation band material contains only one phenanthroline skeleton.
[0365] In one aspect of the organic EL element according to the first embodiment, the first electron transport band material is not a compound having an anthracene skeleton.
[0366] In one aspect of the organic EL element according to the first embodiment, the first electron transport band material is a compound represented by the formula (E4) or (E42).
[0367] (Method for manufacturing the electron transport band material) The electron transport band material can be manufactured by a known method. Further, the electron transport band material can also be manufactured by following a known method and using known alternative reactions and raw materials adapted to the target product.
[0368] (Specific examples of the electron transport band material) Specific examples of the electron transport band materials include, for example, the following compounds. However, the present invention is not limited to these specific examples. In this specification, a deuterium atom is represented as D in a chemical formula, and a light hydrogen atom is represented as H or the description thereof is omitted. In this specification, a methyl group may be represented as Me, a phenyl group may be represented as Ph, and a tert-butyl group may be represented as tBu.
[0369]
Chemical formula
[0370]
Chemical formula
[0371]
Chemical formula
[0372]
Chemical formula
[0373] (Metal and metal compound) In one aspect of the organic EL element according to the first embodiment, the metal contained in the low refractive index layer together with the organic material having a refractive index of 1.87 or less is at least one metal selected from the group consisting of rare earth metals, alkali metals, and alkaline earth metals.
[0374] In one aspect of the organic EL element according to the first embodiment, the metal contained in the low refractive index layer together with the organic material having a refractive index of 1.87 or less is at least one metal selected from the group consisting of ytterbium, erbium, lithium, cesium, magnesium, and calcium.
[0375] In one aspect of the organic EL element according to the first embodiment, the metal compound contained in the low refractive index layer together with the organic material having a refractive index of 1.87 or less is at least one metal compound selected from the group consisting of alkali metal compounds and alkaline earth metal compounds.
[0376] In one aspect of the organic EL element according to the first embodiment, the metal compound contained in the low refractive index layer together with the organic material having a refractive index of 1.87 or less is at least one metal compound selected from the group consisting of lithium 8-(quinolinolato) (abbreviation: Liq), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium 2-(2-pyridyl)phenolato (abbreviation: LiPP), lithium 2-(2-pyridyl)-3-pyridinolato (abbreviation: LiPPy), lithium 4-phenyl-2-(2-pyridyl)phenolato (abbreviation: LiPPP), lithium oxide (LiOx), and cesium carbonate. Among the metal compounds, metal complexes (metal complexes having a refractive index of 1.87 or less) that can be used as low refractive index organic materials such as Liq are also included. The electron transport band materials (the first electron transport band material and the second electron transport band material) may be metal complexes as low refractive index organic materials.
[0377] <Hole barrier layer> The hole barrier layer is preferably a layer that transports electrons and prevents holes from reaching a layer on the cathode side of the hole barrier layer (for example, the electron transport layer). The compound contained in the hole barrier layer is, for example, a compound used in a known hole barrier layer. The compound contained in the hole barrier layer is preferably, for example, the electron transport band material described above or below. Also, the compound contained in the hole barrier layer is preferably at least one compound selected from the group consisting of metal complexes, heteroaromatic compounds, and polymer compounds, similar to the compounds that can be used in the electron transport layer described below. Further, the compound contained in the hole barrier layer may be, for example, at least one compound selected from the group consisting of imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives. The positive hole blocking layer is preferably a layer that prevents excitons generated in the light-emitting layer from moving to a layer on the cathode side of the positive hole blocking layer (e.g., an electron transport layer and an electron injection layer, etc.) so that the excitation energy does not leak from the light-emitting layer to the peripheral layer.
[0378] <Electron transport layer> The electron transport layer is a layer containing a substance with high electron transport properties. The aforementioned electron transport band materials can be used for the electron transport layer. Also, for the electron transport layer, 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, 3) polymer compounds can also be used. Specifically, as low molecular weight organic compounds, metal complexes such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), BAlq, Znq, ZnPBO, ZnBTZ, etc. can be used. Also, in addition to metal complexes, heteroaromatic compounds such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), etc. can also be used. The substances described here are mainly 10 -6 cm 2It is a substance having an electron mobility of / (V·s) or more. In addition, as long as it is a substance having higher electron transport property than hole transport property, a substance other than the above may be used as the electron transport layer. Further, the electron transport layer may be composed of a single layer, or may be composed of two or more layers of the above substances laminated. In one aspect of the organic EL element according to the present embodiment, it is preferable that the electron transport layer contains an azine derivative as an electron transport band material, and the azine derivative is preferably a diazine derivative or a triazine derivative, and more preferably a pyrimidine derivative or a 1,3,5-triazine derivative. In addition, a polymer compound can also be used for the electron transport layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy), etc. can be used.
[0379] (Specific examples of other electron transport band materials) In addition to the above-mentioned electron transport band materials, specific examples of other electron transport band materials include, for example, the following compounds. However, the present invention is not limited to these specific examples of electron transport band materials.
[0380]
Chemical formula
[0381]
Chemical formula
[0382]
Chemical formula
[0383] <Electron injection layer> The electron injection layer is a layer containing a material with high electron injection properties. For the electron injection layer, alkali metals, alkaline earth metals, rare earth metals, or their compounds such as lithium (Li), cesium (Cs), calcium (Ca), ytterbium (Yb), erbium (Er), 8-(quinolinolato)lithium (Liq), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiOx), etc. can be used. In addition, substances obtained by incorporating alkali metals, alkaline earth metals, rare earth metals, or their compounds into materials having electron transporting properties, specifically, those obtained by incorporating magnesium (Mg) into Alq, etc. may also be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, a composite material formed by mixing an organic compound and an electron donor may be used for the electron injection layer. Since electrons are generated in the organic compound by the electron donor in such a composite material, it has excellent electron injection properties and electron transporting properties. In this case, the organic compound is preferably a material excellent in transporting the generated electrons. Specifically, for example, the materials constituting the electron transport layer described above (metal complexes, heteroaromatic compounds, etc.) can be used. Any material that exhibits electron donating properties with respect to the organic compound may be used as the electron donor. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and examples include lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. Also, alkali metal oxides and alkaline earth metal oxides are preferable, and examples include lithium oxide, calcium oxide, barium oxide, etc. In addition, Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (abbreviation: TTF) can also be used.
[0384] <Hole transport band> In one aspect of the organic EL element according to the first embodiment, two or more light-emitting units each independently include a hole transport band. In one aspect of the organic EL element according to the first embodiment, the first light-emitting unit includes a first hole transport band, and the second light-emitting unit includes a second hole transport band.
[0385] (First hole transport region) In one aspect of the organic EL element according to the first embodiment, the first hole transport region is disposed between the anode and the first light-emitting region. In one aspect of the organic EL element according to the first embodiment, the first hole transport region includes one or more layers.
[0386] In one aspect of the organic EL element of the first embodiment, the first hole transport region includes two or more layers. In one aspect of the organic EL element according to the first embodiment, the first hole transport region includes a first hole injection layer and a first hole transport layer. In one aspect of the organic EL element according to the first embodiment, the first hole transport region includes, in order from the anode side, a first hole injection layer and a first hole transport layer. In one aspect of the organic EL element according to the first embodiment, the first hole transport layer is in direct contact with the first light-emitting layer in the first light-emitting region.
[0387] In one aspect of the organic EL element of the first embodiment, the first hole transport region includes three or more layers. In one aspect of the organic EL element according to the first embodiment, the first hole transport region includes three layers: a first hole injection layer, a first hole transport layer, and a first electron barrier layer. In one aspect of the organic EL element according to the first embodiment, the first hole transport region includes, in order from the light-emitting region side, a first hole injection layer, a first hole transport layer, and a first electron barrier layer.
[0388] In one aspect of the organic EL element according to the first embodiment, the first electron barrier layer is in direct contact with the first light-emitting layer in the first light-emitting region. In one aspect of the organic EL element according to the first embodiment, the first electron barrier layer and the first hole transport layer are in direct contact. In one aspect of the organic EL element according to the first embodiment, the first hole transport layer and the first hole injection layer are in direct contact. In one aspect of the organic EL element according to the first embodiment, the first hole injection layer and the anode are in direct contact.
[0389] In one aspect of the organic EL element according to the first embodiment, the first hole transport region contains a first hole transport region material.
[0390] (Second positive hole transport region) In one aspect of the organic EL element according to the first embodiment, the second positive hole transport region is disposed between the first light-emitting unit and the second light-emitting region.
[0391] In one aspect of the organic EL element according to the first embodiment, the second positive hole transport region is disposed between the first charge generation region and the second light-emitting region.
[0392] In one aspect of the organic EL element according to the first embodiment, the second positive hole transport region is disposed between the first charge generation layer and the second light-emitting region.
[0393] In one aspect of the organic EL element according to the first embodiment, the second positive hole transport region is disposed between the second charge generation layer and the second light-emitting region.
[0394] In one aspect of the organic EL element according to the present embodiment, the second positive hole transport region includes one or more layers.
[0395] In one aspect of the organic EL element according to the first embodiment, the second positive hole transport region includes a second positive hole transport layer. In one aspect of the organic EL element according to the first embodiment, the second positive hole transport layer is in direct contact with the second light-emitting layer in the second light-emitting region.
[0396] In one aspect of the organic EL element of the first embodiment, the second hole transport band includes two or more layers. In one aspect of the organic EL element according to the first embodiment, the second hole transport band includes a second hole transport layer and a second electron barrier layer. In one aspect of the organic EL element according to the first embodiment, the second hole transport band includes a second hole transport layer and a second electron barrier layer in order from the first light emitting unit side. In one aspect of the organic EL element according to the first embodiment, the second hole transport layer and the second electron barrier layer are in direct contact with each other. In one aspect of the organic EL element according to the first embodiment, the second electron barrier layer is in direct contact with the second light emitting layer in the second light emitting band. In one aspect of the organic EL element according to the first embodiment, the second electron barrier layer may be a layer (low refractive index layer) containing an organic material (low refractive index organic material) having a refractive index of less than 1.87, or a layer (high refractive index layer) containing an organic material (high refractive index organic material) having a refractive index exceeding 1.87.
[0397] In one aspect of the organic EL element according to the first embodiment, a second hole transport layer is disposed between the second charge generation layer and the second light emitting band.
[0398] In one aspect of the organic EL element according to the first embodiment, the second charge generation layer and the second hole transport layer are in direct contact with each other. In one aspect of the organic EL element according to the first embodiment, the second charge generation layer and the second hole transport layer may not be in direct contact with each other.
[0399] In one aspect of the organic EL element according to the first embodiment, the second hole transport layer is a low refractive index layer. When the second hole transport layer is a low refractive index layer, the second hole transport layer contains an organic material having a refractive index of 1.87 or less.
[0400] In one aspect of the organic EL element according to the first embodiment, the second hole transport layer contains a second hole transport band material. In one aspect of the organic EL element according to the first embodiment, the organic material having a refractive index of 1.87 or less contained in the second hole transport layer is the second hole transport band material.
[0401] In one aspect of the organic EL element according to the first embodiment, the refractive index of the second hole transport band material is 1.83 or less.
[0402] In one aspect of the organic EL element according to the first embodiment, the refractive index of the first charge generation band material is 1.83 or less, the refractive index of the second charge generation band material is 1.83 or less, and the refractive index of the second hole transport band material is 1.83 or less. In one aspect of the organic EL element according to the first embodiment, the refractive index of the first charge generation band material is greater than 1.70, the refractive index of the second charge generation band material is 1.70 or less, and the refractive index of the second hole transport band material is 1.70 or less.
[0403] In one aspect of the organic EL element according to the first embodiment, the refractive index of the first electron transport band material is 1.83 or less, the refractive index of the first charge generation band material is 1.83 or less, the refractive index of the second charge generation band material is 1.83 or less, and the refractive index of the second hole transport band material is 1.83 or less. In one aspect of the organic EL element according to the first embodiment, the refractive index of the first electron transport band material is 1.70 or less, the refractive index of the first charge generation band material is greater than 1.70, the refractive index of the second charge generation band material is 1.70 or less, and the refractive index of the second hole transport band material is 1.70 or less.
[0404] In one aspect of the organic EL element according to the first embodiment, the second hole transport band material and the second charge generation band material are the same as or different from each other. In one aspect of the organic EL element according to the first embodiment, the second hole transport band material and the first charge generation band material are different from each other. In one aspect of the organic EL element according to the first embodiment, the second hole transport band material and the first electron transport band material are different from each other.
[0405] In one aspect of the organic EL element according to the first embodiment, when the organic EL element satisfies the condition (TDM1), one of the at least two low refractive index layers in direct contact in the condition (TDM1) is the second hole transport layer.
[0406] In one aspect of the organic EL element according to the first embodiment, the second charge generation layer is the aforementioned first low refractive index layer, and the second hole transport layer is the aforementioned second low refractive index layer.
[0407] In one aspect of the organic EL element according to the first embodiment, the sum of the film thickness of the second charge generation layer and the film thickness of the second hole transport layer is 50 nm or more.
[0408] In one aspect of the organic EL element according to the first embodiment, the first charge generation layer is the aforementioned third low refractive index layer, the second charge generation layer is the aforementioned first low refractive index layer, and the second hole transport layer is the aforementioned second low refractive index layer.
[0409] In one aspect of the organic EL element according to the first embodiment, the sum of the film thickness of the first charge generation layer, the film thickness of the second charge generation layer, and the film thickness of the second hole transport layer is 50 nm or more, or 55 nm or more.
[0410] In one aspect of the organic EL element according to the first embodiment, the first electron transport layer is the aforementioned third low refractive index layer, the first charge generation layer is the aforementioned first low refractive index layer, the second charge generation layer is the aforementioned second low refractive index layer, and the second hole transport layer is the aforementioned fourth low refractive index layer.
[0411] In one aspect of the organic EL element according to the first embodiment, the sum of the film thickness of the first electron transport layer, the film thickness of the first charge generation layer, the film thickness of the second charge generation layer, and the film thickness of the second hole transport layer is 50 nm or more, 60 nm or more, or 70 nm or more.
[0412] In one aspect of the organic EL element according to the first embodiment, the sum of the film thickness of the first electron transport layer, the film thickness of the first charge generation layer, the film thickness of the second charge generation layer, and the film thickness of the second hole transport layer is 100 nm or less, or 90 nm or less.
[0413] In one aspect of the organic EL element according to the first embodiment, the first hole barrier layer is the aforementioned fifth low refractive index layer, the first electron transport layer is the aforementioned third low refractive index layer, the first charge generation layer is the aforementioned first low refractive index layer, the second charge generation layer is the aforementioned second low refractive index layer, and the second hole transport layer is the aforementioned fourth low refractive index layer.
[0414] In one aspect of the organic EL element according to the first embodiment, the sum of the film thickness of the first hole barrier layer, the film thickness of the first electron transport layer, the film thickness of the first charge generation layer, the film thickness of the second charge generation layer, and the film thickness of the second hole transport layer is 50 nm or more, 60 nm or more, or 70 nm or more.
[0415] In one aspect of the organic EL element according to the first embodiment, the sum of the film thickness of the first hole barrier layer, the film thickness of the first electron transport layer, the film thickness of the first charge generation layer, the film thickness of the second charge generation layer, and the film thickness of the second hole transport layer is 100 nm or less, or 90 nm or less.
[0416] (Hole transport band material) In the organic EL element according to the first embodiment, the material contained in the hole transport band is referred to as a hole transport band material. The hole transport band material is, for example, the aforementioned first hole transport band material and second hole transport band material. The hole transport band material can also be used as the second charge generation band material.
[0417] In one aspect of the organic EL element according to the first embodiment, among the layers included in the first hole transport band, at least one of the layers contains, as the first hole transport band material, a compound represented by the following formula (B1) or formula (B2).
[0418] In one aspect of the organic EL element according to the first embodiment, among the layers included in the second hole transport band, at least one of the layers contains, as the second hole transport band material, a compound represented by the following formula (B1) or formula (B2).
[0419] In one aspect of the organic EL element according to the first embodiment, the second charge generation layer contains a compound represented by the following formula (B1) or formula (B2). In one aspect of the organic EL element according to the first embodiment, the second charge generation layer contains, as the second charge generation band material, a compound represented by the following formula (B1) or formula (B2).
[0420] [Chemical formula]
[0421] (In the above formula (B1), L 11 、L 12 and L 13 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, a divalent heterocyclic group having 5 to 50 ring-forming atoms which may be substituted, or a divalent group in which two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms are bonded, A1, B1 and C1 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, or a group represented by -Si(R 121 )(R 122 )(R 123 ), R 121 、R 122 and R 123 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, R 121When there are a plurality of them, the plurality of Rs 121 are the same as or different from each other, R 122 When there are a plurality of them, the plurality of Rs 122 are the same as or different from each other, R 123 When there are a plurality of them, the plurality of Rs 123 are the same as or different from each other.)
[0422]
Chemical formula
[0423] (In the formula (B2), L C1 、L C2 、L C3 and L C4 are each independently, a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, n2 is 1, 2, 3 or 4, When n2 is 1, L C5 is, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, When n2 is 2, 3 or 4, the plurality of Ls C5 are the same as or different from each other, When n2 is 2, 3 or 4, the plurality of Ls C5 are, bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted condensed ring, the L C5 is, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted, Ar 131 Ar 132 Ar 133 and Ar 134 are each independently an aryl group having 6 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, a heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted, or -Si(R 121 )(R 122 )(R 123 ), where R 121 R 122 and R 123 are each independently an aryl group having 6 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, R 121 when there are a plurality of R 121 the plurality of R R 122 when there are a plurality of R 122 the plurality of R R 123 when there are a plurality of R 123 the plurality of R
[0424] In one aspect of the organic EL element according to the present embodiment, in the compound represented by the formula (B2), the first amino group represented by the following formula (B2-1) and the second amino group represented by the following formula (B2-2) are the same group.
[0425]
Chemical formula
[0426] (In the formulas (B2-1) and (B2-2), * is the bonding position with L C5 respectively.)
[0427] In one aspect of the organic EL element according to the present embodiment, the first amino group represented by the formula (B2-1) and the second amino group represented by the formula (B2-2) may be different groups from each other.
[0428] In one aspect of the organic EL element according to the first embodiment, A1, B1, and C1 in the formula (B1) and the following formula (B100) are each independently a group represented by any one of the formulas (1A), (1B), (1C), (1D), (1E), (1F), and (1G) selected from the group consisting of:
[0429]
Chemical formula
[0430] (In the formula (1A), *11 is the bonding position to L 11 , L 12 or L 13 , and one selected from R 101 ~R 105 is a single bond that binds to *12, and one selected from R 106 ~R 110 is a single bond that binds to *13, the R 101 ~R 105 and R 106 ~R 110 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, none of any groups of two or more adjacent ones among the R 101 ~R 105 bond to each other, none of any groups of two or more adjacent ones among the R 106 ~R 110 bond to each other, R 111 ~R 115is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms, R 111 ~R 115 any set of two or more adjacent ones of which does not bond to each other, m is 0, 1 or 2, and n is 0 or 1, when m = 0 and n = 0, *13 is the bonding position to L 11 L 12 or L 13 ; when m = 0 and n = 1, *12 is the bonding position to L 11 L 12 or L 13 ; when m = 1 and n = 0, one selected from R 101 ~R 105 is a single bond bonding to *13.)
[0431]
Chemical formula
[0432] (In the formula (1B), *14 is the bonding position to L 11 L 12 or L 13 ; R 121 ~R 128 one selected from is a single bond bonding to *15, R 121 ~R 128 not being the single bond are independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, R 121 ~R 128 any set of two or more adjacent ones of which does not bond to each other.)
[0433] [Chemical formula]
[0434] (In the above formula (1C), *16 is the bonding position to L 11 , L 12 or L 13 , and R 131 ~R 140 One selected from is a single bond that binds to *17, R 131 ~R 140 that is not the single bond are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, R 131 ~R 140 None of any group consisting of two or more adjacent ones among them bind to each other.)
[0435] [Chemical formula]
[0436] (In the above formula (1D), *18 is the bonding position to L 11 , L 12 or L 13 , and X 11 is an oxygen atom, a sulfur atom, C(Ra)(Rb) or N(Rc), The pair consisting of Ra and Rb binds to each other to form a substituted or unsubstituted monocyclic ring, binds to each other to form a substituted or unsubstituted condensed ring, or do not bind to each other, n is 0 or 1, When n is 0, R 141 ~R 148, Rc, and one selected from Ra and Rb that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring is a single bond connecting to *19, When n is 1, R 141 and R 142 one of which is a single bond connecting to *a, and, R 141 and R 142 the other of which is a single bond connecting to *b, or R 142 and R 143 one of which is a single bond connecting to *a, and, R 142 and R 143 the other of which is a single bond connecting to *b, or R 143 and R 144 one of which is a single bond connecting to *a, and, R 143 and R 144 the other of which is a single bond connecting to *b, (i) R 145 ~R 148 , R 14A , R 14B , R 14C , R 14D and Rc, and (ii) R 141 ~R 144 that are not single bonds connecting to *a and *b, and (iii) Ra and Rb that are not single bonds connecting to *a and *b, do not form the substituted or unsubstituted monocyclic ring, and do not form the substituted or unsubstituted condensed ring, one selected from the group consisting of is a single bond connecting to *19, R 141 ~R 148 , R 14A , R 14B , R 14C , R 14D and Rc, and Ra and Rb that are not single bonds connecting to *19, do not form the substituted or unsubstituted monocyclic ring, and do not form the substituted or unsubstituted condensed ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms. )
[0437]
Chem.
[0438] (In the above formula (1E), *11a is the bonding position to L 11 , L 12 or L 13 , and one selected from R 151 ~R 155 is a single bond bonding to *11b, and the other one selected from R 151 ~R 155 is a single bond bonding to *11c. R 151 ~R 155 that are not the above single bonds are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group. Any group consisting of two or more adjacent ones among R 151 ~R 155 that are not the above single bonds do not bond to each other. R 161 ~R 165 and R 171 ~R 175 are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.)
[0439]
Chem.
[0440] (In the above formula (1F), *11d is the bonding position to L 11 , L 12 or L 13 , and one selected from R 181 ~R 192 is a single bond bonding to *11e. R 181 ~R 192is, independently of each other, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, R other than the single bond 181 ~R 192 None of any set consisting of two or more adjacent ones among them are bonded to each other.)
[0441] [Chemical formula]
[0442] (In the formula (1G), X B is a single bond, an oxygen atom, a sulfur atom, N(R B11 ), or C(R B12 )(R B13 ), and X B When there are a plurality of X B are the same as or different from each other, X B When is C(R B12 )(R B13 ), the pair consisting of R B12 and R B13 either bonds to each other to form a substituted or unsubstituted monocyclic ring, bonds to each other to form a substituted or unsubstituted condensed ring, or bonds to each other to form a substituted or unsubstituted condensed ring, or do not bond to each other, R B1 R B2 R B3 R B4 R B5 R B6 R B7 R B8 R B9 R B10 R B11 R B12 and R B13 one of is a single bond bonded to *1, B1 R B2 R B3 R B4 RB5 , R B6 , R B7 , R B8 and R B11 are each independently, a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by, -O-(R 904 ) group represented by, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R B9 and R B10 from the group consisting of, bond to each other to form a substituted or unsubstituted monocyclic ring, bond to each other to form a substituted or unsubstituted condensed ring, or do not bond to each other, *1 is not a single bond that binds to, and does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring R B9 , R B10 , R B12 and R B13 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, *2 is the bonding position with L 11 , L 12 or L 13 ).) (In the group represented by the formula (1G), R 901 , R 902 , R 903and R 904 is, independently of one another, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, and R 901 when a plurality of R's are present, the plurality of R's 901 are the same as or different from one another, and when a plurality of R's 902 are present, the plurality of R's 902 are the same as or different from one another, and when a plurality of R's 903 are present, the plurality of R's 903 are the same as or different from one another, and when a plurality of R's 904 are present, the plurality of R's 904 are the same as or different from one another.)
[0443] In one aspect of the organic EL element according to the first embodiment, the hole transport band material is a compound represented by the following formula (B100). In one aspect of the organic EL element according to the first embodiment, the second hole transport band material is a compound represented by the following formula (B100).
[0444]
Chemical formula
[0445] (In the above formula (B100), L 11 L 12 and L 13 are, independently of one another, a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, a divalent heterocyclic group having 5 to 50 ring-forming atoms which is substituted or unsubstituted, or a divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms and a divalent heterocyclic group having 5 to 50 ring-forming atoms which is substituted or unsubstituted, A1, B1, and C1 are, independently of one another, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, -Si(R C1 )(R C2 )(R C3 ), or a group represented by the formula (1G), provided that at least one selected from the group consisting of A1, B1, and C1 is a group represented by the formula (1G), R C1 , R C2 and R C3 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, when a plurality of R C1 are present, the plurality of R C1 are the same as or different from each other, when a plurality of R C2 are present, the plurality of R C2 are the same as or different from each other, when a plurality of R C3 are present, the plurality of R C3 are the same as or different from each other, in the formula (1G), X B is a single bond, an oxygen atom, a sulfur atom, N(R B11 ) or C(R B12 )(R B13 ), when a plurality of X B are present, the plurality of X B are the same as or different from each other, when X B is C(R B12 )(R B13 ), R B12 and R B13A group consisting of is bond to each other to form a substituted or unsubstituted monocyclic ring, bond to each other to form a substituted or unsubstituted condensed ring, or do not bond to each other, R B1 R B2 R B3 R B4 R B5 R B6 R B7 R B8 R B9 R B10 R B11 R B12 and R B13 one of them is a single bond connecting to *1, R which is not a single bond connecting to *1 B1 R B2 R B3 R B4 R B5 R B6 R B7 R B8 and R B11 are each independently a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a group represented by -Si(R 901 )(R 902 )(R 903 ), a group represented by -O-(R 904 ), a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R B9 and R B10 a group consisting of is bond to each other to form a substituted or unsubstituted monocyclic ring, bond to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, R which is not a single bond bonded to *1, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted condensed ring B9 , R B10 , R B12 and R B13 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, *2 is the bonding position with L 11 , L 12 or L 13 and when there are two or more groups represented by the formula (1G), the two or more groups represented by the formula (1G) are the same as or different from each other.) (In the compound represented by the formula (B100), R (In the compound represented by the formula (B100), R 901 , R 902 , R 903 and R 904 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, when there are a plurality of R 901 , the plurality of R 901 are the same as or different from each other, when there are a plurality of R 902 , the plurality of R 902 are the same as or different from each other, when there are a plurality of R 903 , the plurality of R 903 are the same as or different from each other, when there are a plurality of R 904 , the plurality of R 904 are the same as or different from each other.)
[0446] In one aspect of the organic EL element according to the first embodiment, the group represented by the formula (1G) is a group represented by any one of the following formulas (11G), (12G), and (13G).
[0447]
Chemical formula
[0448]
Chemical formula
[0449] (In the formulas (11G), (12G), or (13G), X B , R B1 , R B2 , R B3 , R B4 , R B5 , R B6 , R B7 , R B8 , *1 and *2 are respectively the same as X B , R B1 , R B2 , R B3 , R B4 , R B5 , R B6 , R B7 , R B8 , *1 and *2, and R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 are each independently a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms, A cycloalkyl group having 3 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, -Si(R 901 )(R 902 )(R 903 ) group represented by -O-(R 904 ) group represented by A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, Z is an oxygen atom, a sulfur atom or C(R Z1 )(R Z2 ), R Z1 and R Z2 are each independently A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, or A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.)
[0450] In one aspect of the organic EL element according to the first embodiment, X in the formulas (1G), (11G), (12G) and (13G) B is a single bond or an oxygen atom.
[0451] In one aspect of the organic EL element according to the first embodiment, the group represented by the formula (1G) is a group represented by any one of the formulas (11G-1), (12G-1), (12G-2) and (13G-1) selected from the group consisting of
[0452]
Chemical formula
[0453]
Chemical formula
[0454] (In the formula (11G-1), (12G-1), (12G-2) or (13G-1), R B1 、R B2 、R B3 、R B4 、R B5 、R B6 、R B7 、R B8 、*1 and *2 are each R in the formula (1G) B1 、R B2 、R B3 、R B4 、R B5 、R B6 、R B7 、R B8 、are synonymous with *1 and *2, R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 and R 20 are each independently a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.)
[0455] R in the formulas (11G), (12G), (13G), (11G-1), (12G-1), (12G-2) and (13G-1) 11 、R 13 、R 14 、R 15 、R 16 、R 17 、R18 and R 20 is a hydrogen atom. In the formulas (11G), (12G), (13G), (11G-1), (12G-1), (12G-2) and (13G-1), R 12 and R 19 are each independently a substituent other than a hydrogen atom. In the formulas (11G), (12G), (13G), (11G-1), (12G-1), (12G-2) and (13G-1), R 11 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 20 is a hydrogen atom, and R 12 and R 19 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms.
[0456] In one aspect of the organic EL element according to the present embodiment, in the formula (1D), when n is 1, R 141 and R 142 one of them is a single bond bonded to *a, and R 141 and R 142 the other of them is a single bond bonded to *b, the formula (1D) is represented by the following formula (13D), R 142 and R 143 one of them is a single bond bonded to *a, and R 142 and R 143 the other of them is a single bond bonded to *b, the formula (1D) is represented by the following formula (12D), R 143 and R 144 one of them is a single bond bonded to *a, and R 143 and R 144 the other of them is a single bond bonded to *b, the formula (1D) is represented by the following formula (11D).
[0457] In one aspect of the organic EL element according to the first embodiment, at least one selected from the group consisting of A1, B1, and C1 in the formula (B1) or formula (B100) is a group represented by any one of the formulas (11D), (12D), and (13D) selected from the group consisting of the following formulas.
[0458]
Chemical formula
[0459]
Chemical formula
[0460]
Chemical formula
[0461] (In the formulas (11D), (12D), and (13D), *18 is the bonding position to L 11 , L 12 or L 13 , and X 11 is synonymous with X 11 in the formula (1D), and (iv) One selected from the group consisting of R 141 ~R 148 , R 14A , R 14B , R 14C , R 14D and Rc, and (v) Ra and Rb which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring, is a single bond bonding to *19, R 141 ~R 148 , R 14A , R 14B , R 14C , R 14Dand Rc, and Ra and Rb which are not single bonds bonding to *19 and do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms.)
[0462] In one aspect of the organic EL element according to the first embodiment, R in the formula (11D) 148 is a single bond bonding to *19.
[0463] In one aspect of the organic EL element according to the first embodiment, X in the formula (11D) 11 is an oxygen atom.
[0464] In one aspect of the organic EL element according to the first embodiment, n in the formula (1D) is 0.
[0465] In one aspect of the organic EL element according to the first embodiment, at least one selected from the group consisting of A1, B1, and C1 in the formula (B1) or formula (B100) is a group represented by any one of the following formulas (14D), (15D), (16D), and (17D).
[0466]
Chemical formula
[0467]
Chemical formula
[0468]
Chemical formula
[0469]
Chemical formula
[0470] (In the formulas (14D), (15D), (16D), and (17D), *18 is the bonding position to L 11 , L 12 or L 13 and is a bonding position to, (vi) One selected from the group consisting of R 141 ~R 148 and Rc, and (vii) Ra and Rb that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring is a single bond that binds to *19, R 141 ~R 148 and Rc that are not the single bond binding to *19, and Ra and Rb that are not the single bond binding to *19, do not form the substituted or unsubstituted monocyclic ring, and do not form the substituted or unsubstituted condensed ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms.)
[0471] In one aspect of the organic EL element according to the first embodiment, R 141 , R 144 , R 145 , or R 148 in the formula (14D) is a single bond that binds to *19.
[0472] In one aspect of the organic EL element according to the first embodiment, Rc in the formula (15D) is a single bond that binds to *19.
[0473] In one aspect of the organic EL element according to the first embodiment, L 11 , L 12 and L 13 in the formula (B1) or (B100) are each independently a single bond or a group represented by the following formula (L1), (L2), (L3), (L4), (L5), (L6), (L7), (L8), (L9), or (L10).
[0474]
Chem.
[0475] In the above formulas (L1) to (L10), * indicates the bonding position. The groups represented by the formulas (L1) to (L10) may each independently have one or more of the aforementioned "optional substituents", or may not have them. The groups represented by the formulas (L1) to (L10) may each independently have one or more deuterium atoms.
[0476] In one aspect of the organic EL element according to the first embodiment, when L 11 is a single bond, A1 is directly bonded to the amino group nitrogen atom in the formula (B1) or (B100), and L 12 is a single bond, B1 is directly bonded to the amino group nitrogen atom in the formula (B1) or (B100), and L 13 is a single bond, C1 is directly bonded to the amino group nitrogen atom in the formula (B1) or (B100).
[0477] In one aspect of the organic EL element according to the first embodiment, the hole transport band materials (for example, the first hole transport band material and the second hole transport band material) are each independently a compound represented by the following formula (B10), (B11), (B12), (B13), (B14) or (B15).
[0478]
Chem.
[0479]
Chem.
[0480]
Chem.
[0481] (In the formulas (B10), (B11), (B12), (B13), (B14), and (B15), L 11 , L 12 , L 13 , A1, B1, and C1 are each the L 11 , L 12 , L 13 , A1, B1, and C1 in the formula (B1) or (B100), respectively, and are synonymous with R1, R2, R3, and R4 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms, the four R1s are the same as or different from each other, the four R2s are the same as or different from each other, the four R3s are the same as or different from each other, the four R4s are the same as or different from each other.)
[0482] In one aspect of the organic EL element according to the first embodiment, the hole transport band materials (for example, the first hole transport band material and the second hole transport band material) are each independently a compound represented by the following formula (B16), (B17), (B18), (B19), or (B20).
[0483]
Chemical formula
[0484]
Chemical formula
[0485] (In the formulas (B16), (B17), (B18), (B19), and (B20), A1, B1, and C1 are each the A1, B1, and C1 in the formula (B1) or (B100), respectively, and are synonymous with R1, R2, R3, and R4 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms, and the four R1s are the same as or different from each other, the four R2s are the same as or different from each other, the four R3s are the same as or different from each other, and the four R4s are the same as or different from each other.)
[0486] In one aspect of the organic EL element according to the first embodiment, in the first hole transport band material and the second hole transport band material, R1, R2, and R3 are deuterium atoms.)
[0487] In one aspect of the organic EL element according to the first embodiment, at least one selected from the group consisting of A1, B1, and C1 in the formulas (B1), (B100), (B10), (B11), (B12), (B13), (B14), (B15), (B16), (B17), (B18), (B19), and (B20) contains at least one kind of group selected from the group consisting of the groups represented by the formulas (1A) and (1B). Hereinafter, "(B10), (B11), (B12), (B13), (B14), (B15), (B16), (B17), (B18), (B19), and (B20)" may be abbreviated as "(B10) to (B20).")
[0488] In one aspect of the organic EL element according to the first embodiment, one selected from the group consisting of A1, B1, and C1 in the formulas (B1), (B10) to (B20) contains at least one kind of group selected from the group consisting of the groups represented by the formulas (1A) and (1B), and the remaining two selected from the group consisting of A1, B1, and C1 contain at least one kind of group selected from the group consisting of the groups represented by the formulas (1D), (11D), (12D), (13D), (14D), (15D), (16D), and (17D).)
[0489] In one aspect of the organic EL element according to the first embodiment, two selected from the group consisting of A1, B1, and C1 in the formulas (B1), (B100), (B10) to (B20) include at least one group selected from the group consisting of the groups represented by the formulas (1A) and (1B).
[0490] In one aspect of the organic EL element according to the first embodiment, two selected from the group consisting of A1, B1, and C1 in the formulas (B1), (B10) to (B20) include at least one group selected from the group consisting of the groups represented by the formulas (1A) and (1B), and the remaining one selected from the group consisting of A1, B1, and C1 independently includes at least one group selected from the group consisting of the groups represented by the formulas (1D), (11D), (12D), (13D), (14D), (15D), (16D), and (17D).
[0491] In one aspect of the organic EL element according to the first embodiment, at least one selected from the group consisting of A1, B1, and C1 in the formulas (B1), (B100), (B10) to (B20) is a group represented by the formula (1G), and X B is an oxygen atom.
[0492] In one aspect of the organic EL element according to the first embodiment, two selected from the group consisting of A1, B1, and C1 in the formulas (B1), (B100), (B10) to (B20) are groups represented by the formula (1G), and X B is an oxygen atom.
[0493] In one aspect of the organic EL element according to the first embodiment, at least one selected from the group consisting of A1, B1, and C1 in the formulas (B1), (B100), (B10) to (B20) includes at least one group selected from the group consisting of the groups represented by the formulas (11G), (12G), and (13G).
[0494] In one aspect of the organic EL element according to the first embodiment, two selected from the group consisting of A1, B1, and C1 in the formulas (B1), (B100), (B10) to (B20) include at least one group selected from the group consisting of the groups represented by the formulas (11G), (12G), and (13G).
[0495] In one aspect of the organic EL element according to the first embodiment, at least one selected from the group consisting of A1, B1, and C1 in the formulas (B1), (B100), (B10) to (B20) includes at least one group selected from the group consisting of the groups represented by the formulas (11G-1), (12G-1), (12G-2), and (13G-1).
[0496] In one aspect of the organic EL element according to the first embodiment, two selected from the group consisting of A1, B1, and C1 in the formulas (B1), (B100), (B10) to (B20) include at least one group selected from the group consisting of the groups represented by the formulas (11G-1), (12G-1), (12G-2), and (13G-1).
[0497] In one aspect of the organic EL element according to the first embodiment, at least one selected from the group consisting of A1, B1, and C1 in the formulas (B1), (B100), (B10) to (B20) has, as a substituent, one or more alkyl groups having 1 to 20 carbon atoms (preferably 1 to 6 carbon atoms), which may be substituted or unsubstituted.
[0498] In one aspect of the organic EL element according to the first embodiment, at least one selected from the group consisting of A1, B1, and C1 in the formulas (B1), (B100), (B10) to (B20) has, as a substituent, one or more alkyl groups containing a branched chain.
[0499] In one aspect of the organic EL element according to the first embodiment, at least one selected from the group consisting of A1, B1, and C1 in the formulas (B1), (B100), (B10) to (B20) has, as a substituent, one or more tert-butyl groups.
[0500] In one aspect of the organic EL element according to the first embodiment, the hole transport band material is a monoamine compound having one substituted or unsubstituted amino group in the molecule, a diamine compound having two substituted or unsubstituted amino groups in the molecule, a triamine compound having three substituted or unsubstituted amino groups in the molecule, and at least one amine compound selected from the group consisting of a tetraamine compound having four substituted or unsubstituted amino groups in the molecule.
[0501] In one aspect of the organic EL element according to the first embodiment, the first hole transport band material and the second hole transport band material are each independently a monoamine compound or a diamine compound.
[0502] In one aspect of the organic EL element according to the first embodiment, the first hole transport band material and the second hole transport band material are each independently a monoamine compound.
[0503] (Method for manufacturing the hole transport band material according to this embodiment) The hole transport band material according to this embodiment can be manufactured by a known method. Further, the hole transport band material according to this embodiment can also be manufactured by following a known method and using known alternative reactions and raw materials adapted to the target product. (Specific examples of the hole transport band material according to this embodiment) Specific examples of the hole transport band material according to this embodiment include, for example, the following compounds. However, the present invention is not limited to these specific examples.
[0504]
Chemical formula
[0505]
Chemical formula
[0506] [Chemistry]
[0507] [Chemistry]
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[0612] [Chemical]
[0613] <Positive hole transport layer> The positive hole transport layer is a layer containing a substance with high positive hole transport properties. In one aspect of the organic EL element according to the first embodiment, the positive hole transport layer (for example, the first positive hole transport layer and the second positive hole transport layer) may contain a compound different from the aforementioned positive hole transport band material, and for example, one or more compounds selected from the group consisting of aromatic amine compounds, carbazole derivatives, and anthracene derivatives, etc. may be contained. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), etc. aromatic amine compounds can be used. The substances described here mainly have a positive hole mobility of 10 -6 cm 2 / (V·s) or more. For the positive hole transport layer, carbazole derivatives such as CBP, CzPA, PCzPA, and anthracene derivatives such as t-BuDNA, DNA, DPAnth may also be used. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. However, substances with higher hole transport properties than electrons may be used instead of these. Note that the layer containing a substance with high hole transport properties may be a single layer or a layer in which two or more layers made of the above substances are laminated.
[0614] In one aspect of the organic EL element according to the first embodiment, the hole transport band may include one hole transport layer or two or more hole transport layers.
[0615] (Specific examples of other hole transport band materials) In addition to the aforementioned hole transport band materials, specific examples of other hole transport band materials include, for example, the following compounds. However, the present invention is not limited to these specific examples of hole transport band materials.
[0616]
Chemical formula
[0617]
Chemical formula
[0618] <Electron barrier layer> The electron barrier layer preferably transports holes and prevents electrons from reaching a layer on the anode side of the electron barrier layer (for example, a hole transport layer). In one aspect of the organic EL element according to the first embodiment, the first light emitting unit includes a first electron barrier layer, and the second light emitting unit includes a second electron barrier layer. In one aspect of the organic EL element of the first embodiment, the compound contained in the electron barrier layer (for example, the first electron barrier layer and the second electron barrier layer) is a hole transport band material. In one aspect of the organic EL element of the first embodiment, the compound contained in the electron barrier layer is a compound represented by the formula (B1) or (B100). In one aspect of the organic EL element of the first embodiment, the compound contained in the electron barrier layer is a compound used in a known electron barrier layer and is at least any one compound selected from the group consisting of aromatic amine compounds and carbazole derivatives. Further, the compound contained in the electron barrier layer may be a monoamine compound having only one substituted or unsubstituted amino group in the molecule. Further, the compound contained in the electron barrier layer may have a substituted or unsubstituted carbazolyl group and one substituted or unsubstituted amino group in the molecule. The electron barrier layer may be a layer that prevents excitons generated in the light-emitting layer from moving to a layer on the anode side of the electron barrier layer (for example, a hole transport layer and a hole injection layer, etc.) so that the excitation energy does not leak from the light-emitting layer to the peripheral layer.
[0619] <Hole injection layer> In one aspect of the organic EL element according to the first embodiment, a hole injection layer is disposed between the anode and the light-emitting band, or between the charge generation band and the light-emitting band located on the cathode side of the charge generation band. The hole injection layer is a layer containing a substance with high hole injection properties. As substances with high hole injection properties, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. can be used. In addition, examples of substances with high hole injection properties include aromatic amine compounds such as low molecular weight organic compounds 4,4’,4’’-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4’,4’’-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4’-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4’-bis(N-{4-[N’-(3-methylphenyl)-N’-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), etc. In addition, as substances with high hole injection properties, high molecular weight compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, high molecular weight compounds such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N’-[4-(4-diphenylamino)phenyl]phenyl-N’-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N’-bis(4-butylphenyl)-N,N’-bis(phenyl)benzidine] (abbreviation: Poly-TPD) can be mentioned. Also, high molecular weight compounds added with acids such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can be used.
[0620] In one aspect of the organic EL element according to the present embodiment, a compound (hole transport band material) that can be used for the hole transport layer can also be used for the hole injection layer. In this case, the hole injection layer preferably contains a hole transport band material and an acceptor material.
[0621] (Acceptor material) The acceptor material includes at least one of a first ring structure represented by the following formula (P11) and a second ring structure represented by the following formula (P12).
[0622] [Chemical formula]
[0623] (The first ring structure represented by the formula (P11) is condensed with at least one of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms in the molecule of the acceptor material, =Z 10 The structure represented by is represented by the following formula (P11a), (P11b), (P11c), (P11d), (P11e), (P11f), (P11g), (P11h), (P11i), (P11j), (P11k) or (P11m).)
[0624] [Chemical formula]
[0625] [Chemical formula]
[0626] (In the formula (P11a), (P11b), (P11c), (P11d), (P11e), (P11f), (P11g), (P11h), (P11i), (P11j), (P11k) or (P11m), R 11 ~R 14 as well as R 111 ~R 120are each independently, a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. )
[0627] (In the formula (P12), Z1 to Z5 are each independently, a nitrogen atom, a carbon atom bonded to R 15 , or a carbon atom bonded to another atom in the molecule of the acceptor material, among Z1 to Z5, at least one is a carbon atom bonded to another atom in the molecule of the acceptor material, R 15 is a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by -O-(R 904 ) group represented by -S-(R 905 ) group represented by -N(R 906 )(R 907 ) group represented by A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, Carboxy group, A substituted or unsubstituted ester group, A substituted or unsubstituted carbamoyl group, Nitro group, and Selected from the group consisting of substituted or unsubstituted siloxanyl groups, R 15 When there are a plurality of R 15 , the plurality of R
[0628] (In the acceptor material, R 901 ~R 907 are each independently Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901 When there are a plurality of R 901 , the plurality of R R 902 When there are a plurality of R 902 , the plurality of R R 903 When there are a plurality of R 903are identical to each other or different from each other, R 904 When there are a plurality of R's, the plurality of R's 904 are identical to each other or different from each other, R 905 When there are a plurality of R's, the plurality of R's 905 are identical to each other or different from each other, R 906 When there are a plurality of R's, the plurality of R's 906 are identical to each other or different from each other, R 907 When there are a plurality of R's, the plurality of R's 907 are identical to each other or different from each other.)
[0629] In one aspect of the organic EL element according to this embodiment, the acceptor material has at least one cyano group.
[0630] In one aspect of the organic EL element according to this embodiment, the hole injection layer contains a hole transport band material, the acceptor material and the hole transport band material are different from each other, and the content of the acceptor material in the hole injection layer is less than 50% by mass.
[0631] In one aspect of the organic EL element according to this embodiment, the content of the acceptor material in the hole injection layer is 10% by mass or less, or 5% by mass or less.
[0632] In one aspect of the organic EL element according to this embodiment, the content of the acceptor material in the hole injection layer is 1% by mass or more, or 3% by mass or less.
[0633] In one aspect of the organic EL element according to this embodiment, when the hole injection layer contains an acceptor material and a hole transport band material, the content of the hole transport band material in the hole injection layer is preferably 40% by mass or more, more preferably 45% by mass or more, and still more preferably 50% by mass or more. The content of the hole transport band material in the hole injection layer is preferably 99.5% by mass or less. The total content of the acceptor material and the hole transport band material in the hole injection layer is 100% by mass or less.
[0634] In this specification, the ester group is at least any group selected from the group consisting of an alkyl ester group and an aryl ester group.
[0635] The alkyl ester group in this specification is, for example, -C(=O)OR E represented by. R E is, for example, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 10 carbon atoms).
[0636] The aryl ester group in this specification is, for example, -C(=O)OR Ar represented by. R Ar is, for example, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.
[0637] The siloxanyl group in this specification is a silicon compound group via an ether bond, and is, for example, a trimethylsiloxanyl group.
[0638] The carbamoyl group in this specification is represented by -CONH2. The substituted carbamoyl group in this specification is, for example, -CONH-Ar C or -CONH-R C represented by. Ar C is, for example, at least any group selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms (preferably 6 to 10 ring-forming carbon atoms) and a heterocyclic group having 5 to 50 ring-forming atoms (preferably 5 to 14 ring-forming atoms). Ar C may be a group in which a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms are bonded. R C is, for example, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 6 carbon atoms).
[0639] In the acceptor material, it is also preferable that all the groups described as "substituted or unsubstituted" are "unsubstituted" groups.
[0640] (Specific examples of acceptor materials) Specific examples of acceptor materials include, for example, the following compounds. However, the present invention is not limited to these specific examples of acceptor materials.
[0641] [Chemical formula]
[0642] [Chemical formula]
[0643] (Other components of the organic EL element) The configuration of the organic EL element will be further described.
[0644] (Substrate) The substrate is used as a support for the organic EL element. As the substrate, for example, glass, quartz, plastic, etc. can be used. Also, a flexible substrate may be used. A flexible substrate is a substrate that can be bent (flexible), and examples include plastic substrates. Examples of materials for forming the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Also, an inorganic vapor deposition film can be used.
[0645] (Anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof having a large work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO: Indium Tin Oxide), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, etc. can be mentioned. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metal materials (for example, titanium nitride), etc. can be mentioned. These materials are usually formed into a film by a sputtering method. For example, indium zinc oxide can be formed by a sputtering method by using a target in which 1% by mass or more and 10% by mass or less of zinc oxide is added to indium oxide. Also, for example, tungsten oxide and indium oxide containing zinc oxide can be formed by a sputtering method by using a target containing 0.5% by mass or more and 5% by mass or less of tungsten oxide and 0.1% by mass or more and 1% by mass or less of zinc oxide with respect to indium oxide. In addition, it may be produced by a vacuum evaporation method, a coating method, an inkjet method, a spin coating method, or the like. Among the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that facilitates hole injection regardless of the work function of the anode, so materials possible as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures thereof, and also including elements belonging to Group 1 or Group 2 of the periodic table) can be used. Elements belonging to Group 1 or Group 2 of the periodic table, which are materials with a small work function, 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 these (for example, MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these can also be used. When forming an anode using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Further, when using a silver paste or the like, a coating method, an inkjet method, or the like can be used.
[0646] When the organic EL element is of the bottom emission type, the anode is a light-transmissive electrode having light transmissivity. The light-transmissive electrode is preferably formed of a metal material having light transmissivity or semi-transmissivity that transmits light emitted from the light-emitting layer. In this specification, light transmissivity or semi-transmissivity means the property of transmitting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The metal material having light transmissivity or semi-transmissivity can be appropriately selected from the materials listed in the section of the anode and used. The metal material having light transmissivity or semi-transmissivity may be the material listed as the material used for the conductive layer (or transparent conductive layer) described later.
[0647] When the organic EL element is of the top emission type, the anode is a light-reflective electrode having a light-reflecting layer. The light-reflecting layer is preferably formed of a metal material having light reflectivity. In this specification, light reflectivity means the property of reflecting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The metal material having light reflectivity can be appropriately selected from the materials listed in the section of the anode and used. As the metal material used for the light reflection layer, for example, a single material of any metal selected from the group consisting of Al, Ag, Ta, Zn, Mo, W, Ni, Cr, etc., or an alloy material having any metal selected from this group as the main component (preferably 50% by mass or more of the whole); an amorphous alloy selected from the group consisting of NiP, NiB, CrP, CrB, etc.; a microcrystalline alloy selected from the group consisting of NiAl and silver alloy, etc. may be mentioned. Further, as the metal material used for the light reflection layer, at least one alloy selected from the group consisting of APC (alloy of silver, palladium and copper), ARA (alloy of silver, rubidium and gold), MoCr (alloy of molybdenum and chromium), and NiCr (alloy of nickel and chromium), etc. may be used. The light reflection layer may be a single layer or a plurality of layers.
[0648] The anode as the light reflective electrode may be composed only of the light reflection layer, or may have a multilayer structure having the light reflection layer and a conductive layer (preferably a transparent conductive layer). When the anode has the light reflection layer and the conductive layer, it is preferable that the conductive layer is disposed between the reflection layer and the layer including the hole transport band (for example, a hole injection layer or a hole transport layer). Further, the anode may have a multilayer structure in which the light reflection layer is disposed between two conductive layers (a first conductive layer and a second conductive layer). In the case of such a multilayer structure, the first conductive layer and the second conductive layer may be formed of the same material or may be formed of different materials from each other. The material used for the conductive layer can be appropriately selected and used from the materials listed in the item of the anode. In addition, as the conductive layer (transparent conductive layer) as a transparent electrode, a metal, an alloy, an electrically conductive compound, and a mixture thereof having a large work function (specifically, 4.0 eV or more) can also be used. In addition, for the conductive layer, for example, alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca) and strontium (Sr), alloys containing at least one selected from the group consisting of alkali metals and alkaline earth metals (for example, MgAg and AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing at least one selected from rare earth metals can also be used.
[0649] (Cathode) For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, and mixtures thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg), calcium (Ca) , alkaline earth metals such as strontium (Sr), and alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these. When forming the cathode using an alkali...
Claims
1. An organic electroluminescent element, wherein the organic electroluminescent element has an anode, a cathode, and two or more light-emitting units disposed between the anode and the cathode, the two or more light-emitting units include at least a first light-emitting unit and a second light-emitting unit, the first light-emitting unit and the second light-emitting unit are arranged in this order from the anode side toward the cathode side, the first light-emitting unit includes a first emission band, the second light-emitting unit includes a second emission band, one or more low refractive index layers are disposed between the first emission band and the second emission band, each of the one or more low refractive index layers independently contains an organic material having a refractive index of 1.87 or less, the following condition (TDM1) or (TDM2) is satisfied, an organic electroluminescent element. (Condition (TDM1): Two or more of the low refractive index layers are disposed between the first emission band and the second emission band, at least two of the low refractive index layers are in direct contact, the total thickness of each of the at least two directly contacting low refractive index layers is 50 nm or more, and at least one of the at least two directly contacting low refractive index layers contains the organic material and at least one selected from the group consisting of metals and metal compounds. Condition (TDM2): At least one low refractive index layer having a thickness of 50 nm or more is disposed between the first emission band and the second emission band, and the low refractive index layer having a thickness of 50 nm or more contains the organic material and at least one selected from the group consisting of metals and metal compounds.)
2. The refractive index of at least one of the organic materials contained in the one or more low refractive index layers is 1.83 or less, The organic electroluminescent element according to claim 1.
3. A charge generation band is disposed between each of the two or more light-emitting units, each of the charge generation bands independently includes at least one charge generation layer, The organic electroluminescent element according to claim 1.
4. At least one of the charge generation bands includes two or more charge generation layers, The organic electroluminescent element according to claim 3.
5. A first charge generation band is disposed between the first light-emitting unit and the second light-emitting unit, The first charge generation band includes at least a first charge generation layer. The organic electroluminescence device according to any one of claims 2 to 4. **Claim 6** When the organic electroluminescence device satisfies the condition (TDM1), one of the at least two low refractive index layers that are in direct contact in the condition (TDM1) is the first charge generation layer. When the organic electroluminescence device satisfies the condition (TDM2), one of the low refractive index layers having a film thickness of 50 nm or more in the condition (TDM2) is the first charge generation layer. The organic electroluminescence device according to claim 5. **Claim 7** The first charge generation layer contains the organic material and at least one selected from the group consisting of metals and metal compounds. The organic electroluminescence device according to claim 6. **Claim 8** The refractive index of the organic material contained in the first charge generation layer is 1.83 or less. The organic electroluminescence device according to claim 7. **Claim 9** A first electron transport band is disposed between the first light emission band and the first charge generation layer. The first electron transport band includes one or more layers. The organic electroluminescence device according to any one of claims 5 to 8. **Claim 10** Each of the one or more layers included in the first electron transport band is the low refractive index layer. The organic electroluminescence device according to claim 9. **Claim 11** The first electron transport band includes a first electron transport layer. The first charge generation layer and the first electron transport layer are in direct contact. The organic electroluminescence device according to claim 9 or claim 10. **Claim 12** The first electron transport layer is the low refractive index layer. The organic electroluminescence device according to claim 11. **Claim 13** The first light emission band includes a first light emission layer. The first light emission layer contains a first host material. The first electron transport layer contains a first electron transport band material. The triplet energy T of the first host material 1 (H1) and the triplet energy T 1 (E1) of the first electron transport band material satisfy the relationship of the following mathematical formula (Formula 1): The organic electroluminescence device according to claim 11 or claim 12. T 1 (E1) > T 1 (H1) … (number 1) **Claim 14** The first light emission layer and the first electron transport layer are in direct contact. The organic electroluminescence device according to claim 13. **Claim 15** The first electron transport band further includes a first hole barrier layer between the first electron transport layer and the first light-emitting band. The organic electroluminescence device according to claim 11 or claim 12.
16. The first hole barrier layer is the low refractive index layer. The organic electroluminescence device according to claim 15.
17. The first hole barrier layer contains a first electron transport band material. The organic electroluminescence device according to claim 15 or claim 16.
18. The refractive index of the first electron transport band material is 1.83 or less. The organic electroluminescence device according to claim 13 or claim 17.
19. The first electron transport band material is a compound represented by the following formula (E1). The organic electroluminescence device according to any one of claims 13, 17, and 18. 【Chemical 1】 (In the formula (E1), R 101 ~R 110 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by -O-(R 904 ) group represented by -S-(R 905 ) group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 a group represented by -COOR 802 a group represented by a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, or a group represented by the formula (E11), However, R 101 ~R 110 at least one of which is a group represented by the formula (E11), when a plurality of groups represented by the formula (E11) exist, the plurality of groups represented by the formula (E11) are the same as or different from each other, L 101 is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 ring-forming atoms which is substituted or unsubstituted, Ar 101 is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, mx is 0, 1, 2, 3, 4 or 5, provided that when mx is 0, -(L 101 ) 0 - is a single bond, L 101 If there are two or more Ls 101 they may be identical to or different from each other Ar 101 When two or more Ars exist, the two or more Ars 101 are identical to or different from each other, * in the formula (E11) indicates the bonding position with the pyrene ring in the formula (E1).) (In the formula (E1), R 901 , R 902 , R 903 , R 904 , R 905 , R 801 and R 802 are each independently, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901 When there are a plurality of Rs 901 they may be the same as or different from each other R 902 When there are a plurality of R's 902 they may be the same as or different from each other R 903 When there are a plurality of R's 903 they may be the same as or different from each other R 904 When there are a plurality of R's 904 they may be the same as or different from each other R 905 If there are a plurality of R's 905 they may be the same as or different from each other R 801 When there are a plurality of R's 801 they may be the same as or different from each other R 802 When there are a plurality of R's 802 they may be the same as or different from each other.)
20. The first electron transport band material is a compound represented by the following formula (E2). The organic electroluminescence element according to any one of claims 13, 17, and 18. 【Chemical 2】 (In the formula (E2), R 201 to R 212 at least one set consisting of two or more adjacent ones among them is bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 201 ~R 212 each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by -O-(R 904 ) group, -S-(R 905 ) group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 a group represented by -COOR 802 a group represented by a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, or a group represented by the formula (E21), However, R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 201 ~R 212 at least one of which is a group represented by the formula (E21), when there are a plurality of groups represented by the formula (E21), the plurality of groups represented by the formula (E21) are the same or different from each other, L 201 is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 ring-forming atoms which is substituted or unsubstituted, ma is 0, 1, 2, 3, 4 or 5, provided that when ma is 0, -(L 201 ) 0 - is a single bond, L 201 When there are two or more Ls 201 they may be identical to or different from each other Ar 201 is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, Ar 201 When two or more Ars exist, the two or more Ars 201 are the same as each other or different from each other, The * in the formula (E21) indicates the bonding position with the benz[a]anthracene ring in the formula (E2). However, when one or more sets of two or more adjacent ones among R 201 ~R 212 form the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted condensed ring, the * in the formula (E21) indicates the bonding position with the mother skeleton of the formed ring structure.) (In the formula (E2), R 901 , R 902 , R 903 , R 904 , R 905 , R 801 and R 802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901 When there are a plurality of R's 901 they may be the same as or different from each other R 902 When there are a plurality of R's 902 they may be the same as or different from each other R 903 When there are a plurality of R's 903 they may be the same as or different from each other R 904 When there are a plurality of R's 904 they may be the same as or different from each other R 905 When there are a plurality of R's 905 they may be the same as or different from each other R 801 When there are a plurality of R's 801 they may be the same as or different from each other R 802 When there are a plurality of R's 802 they may be the same as or different from each other.) [
21. ] The first electron transport band material is a compound represented by the following formula (E3). The organic electroluminescence element according to any one of claims 13, 17, and 18. 【Chemical Formula 3】 (In the formula (E3), R 307 and R 312 One of them represents a single bond with *1, and R 307 and R 312 The other of them represents a single bond with *2, R 301 ~R 306 , R 308 ~R 311 , and R 322 ~R 325 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by -O-(R 904 ) group, -S-(R 905 ) group, -N(R 906 )(R 907 ) group represented by a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms) R 321 is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms, Ar 31 is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, a substituted or unsubstituted oxygen-containing heterocyclic group having 5 to 18 ring-forming atoms, or a substituted or unsubstituted sulfur-containing heterocyclic group having 5 to 18 ring-forming atoms, L 31 and L 32 are each independently a substituted or unsubstituted arylene group having 6 to 14 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 14 ring-forming atoms, n1 is 0, 1, 2 or 3, n2 is 0, 1, 2 or 3, When n1 is 0, -(L 31 ). 0 - is a single bond, When n1 is 2 or more, two or more Ls 31 are connected in series with each other, When n1 is 2 or more, two or more Ls 31 are the same as each other or different from each other, When n2 is 0, -(L 32 ) 0 - is a single bond, When n2 is 2 or more, two or more Ls 32 are connected in series with each other, When n2 is 2 or more, two or more Ls 32 are the same as each other or different from each other.) (In the formula (E3), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 are each independently, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901 When there are a plurality of R's 901 they may be the same as or different from each other R 902 When there are a plurality of R's 902 they may be the same as or different from each other R 903 When there are a plurality of R's 903 they may be the same as or different from each other R 904 When there are a plurality of R's 904 they may be the same as or different from each other R 905 When there are a plurality of R's 905 they may be the same as or different from each other R 906 When there are a plurality of R's 906 they may be the same as or different from each other R 907 When there are a plurality of Rs 907 they may be the same as or different from each other.) Claim 22 The first electron transport band material is a compound represented by the following formula (E4), The organic electroluminescence device according to any one of claims 13, 17 and 18. 【Chemical Formula 4】 (In the formula (E4), X 2 is N or C-(L 42 )m 2 -(Ar 42 )m 21 and is X 4 is N or C-(L 44 )m 4 -(Ar 44 )m 41 and is X 5 is N or C-(L 45 )m 5 -(Ar 45 )m 51 and is X 6 is N or C-(L 46 )m 6 -(Ar 46 )m 61 and X 2 、 X 4 、 X 5 and X 6 wherein at least one of them is a nitrogen atom, L 41 ~L 46 are each independently a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, m 1 is 0, 1, 2 or 3, and when m 1 is 0, -(L 41 ) 0 - is a single bond, m 2 is 0, 1, 2 or 3, and when m 2 is 0, -(L 42 ) 0 - is a single bond, m 3 is 0, 1, 2, or 3, and when m 3 is 0, -(L 43 ) 0 - is a single bond, m 4 is 0, 1, 2 or 3, and when m 4 is 0, -(L 44 ) 0 - is a single bond, m 5 is 0, 1, 2 or 3, and when m 5 is 0, -(L 45 ) 0 - is a single bond, m 6 is 0, 1, 2 or 3, and when m 6 is 0, -(L 46 ) 0 - is a single bond, m 11 is 1, 2, 3, or 4, and m 21 is 1, 2, 3, or 4, and m 31 is 1, 2, 3 or 4, and m 41 is 1, 2, 3 or 4, and m 51 is 1, 2, 3 or 4, and m 61 is 1, 2, 3, or 4, and Ar 41 ~Ar 46 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 911 )(R 912 )(R 913 ) group represented by -O-(R 914 ) group -S-(R 915 ) group represented by -N(R 916 )(R 917 ) group represented by -P(=O)(R 918 )(R 919 )-represented group a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 920 a group represented by -COOR 921 a group represented by a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, However, Ar 41 ~Ar 46 at least one of which is a substituted or unsubstituted aryl group having 13 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 13 to 50 ring-forming atoms. (In the above formula (E4), R 911 , R 912 , R 913 , R 914 , R 915 , R 916 , R 917 , R 918 , R 919 , R 920 and R 921 are each independently, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 911 When there are a plurality of R's 911 they may be the same as or different from each other R 912 When there are a plurality of R's 912 they may be the same as or different from each other R 913 When there are a plurality of R's 913 they may be the same as or different from each other R 914 When there are a plurality of R's 914 they may be the same as or different from each other R 915 When there are a plurality of R's 915 they may be the same as or different from each other R 916 When there are a plurality of R's 916 they may be the same as or different from each other R 917 When there are a plurality of Rs 917 they may be the same as or different from each other R 918 When there are a plurality of R's 918 they may be the same as or different from each other R 919 When there are a plurality of R's 919 they may be the same as or different from each other R 920 When there are a plurality of R's 920 they may be the same as or different from each other R 921 When there are a plurality of R's 921 they may be the same as or different from each other.) Claim 23 The first electron transport band material is a compound represented by the following formula (E41), The organic electroluminescence element according to claim 22. [Chemical Formula 5] (In the formula (E41), L 41 、L 43 、and L 45 are each synonymous with L 41 、L 43 、and L 45 in formula (E4), m 1 、m 3 、and m 5 are each synonymous with m 1 、m 3 、and m 5 in formula (E4), and R A and R B One of them represents a single bond with *3, and R that is not a single bond with *3 A or R B is a hydrogen atom or a substituent S, and R A or R B In the case of "substituted or unsubstituted" in the substituent S as R or R, when it is "substituted", it has one or more substituents T R 401 ~R 409 each independently represents a hydrogen atom or a substituent R, the substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 911 )(R 912 )(R 913 ) group represented by -O-(R 914 ) group, -S-(R 915 ) group represented by -N(R 916 )(R 917 ) group represented by -P(=O)(R 918 )(R 919 ) group represented by a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, and is selected from the group consisting of when two or more substituents R are present, the two or more substituents R are the same as or different from each other, R 410 is a hydrogen atom, R 401 to R 409 and R not singly bonded to *3 A and R B wherein pairs consisting of two or more adjacent ones of them are not bonded to each other X 6 is a nitrogen atom or C—Ar 46 wherein Ar 46 is a hydrogen atom or a substituent V, Ar 41 and Ar 45 at least one of which is a substituent X, and in the case of substituent X as Ar 41 and Ar 45 in the case of "substituted or unsubstituted" in the case of substituent X as, in the case of "substituted", it has one or more substituents U Ar other than the substituent X 41 and Ar 45 are a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms and not containing a nitrogen atom, the substituent X is a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benzanthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzotriphenylenyl group, a substituted or unsubstituted tetracenyl group, a substituted or unsubstituted pentacenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted benzofluoranthenyl group, a substituted or unsubstituted perylenyl group, a heterocyclic group represented by the following formula (E411), and a group selected from the group consisting of a heterocyclic group represented by the following formula (E412), when two or more substituents X are present, the two or more substituents X are the same as or different from each other, when two or more substituents U are present, the two or more substituents U are the same as or different from each other, R A or R B as substituents S, R A or R B in the case of "substituted or unsubstituted", substituents T, Ar 41 and Ar 45 in the case of "substituted or unsubstituted", substituent U, and Ar 46 as substituent V are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A cycloalkyl group having 3 to 50 carbon atoms in the ring, which may or may not be substituted, -Si(R 911 )(R 912 )(R 913 ) group represented by -O-(R 914 ) group, -S-(R 915 ) group, -N(R 916 )(R 917 ) group represented by -P(=O)(R 918 )(R 919 ) group represented by a halogen atom, a cyano group, a nitro group, an aryl group having 6 to 50 carbon atoms in the ring, which may or may not be substituted, and a heterocyclic group having 5 to 50 ring-forming atoms, which may or may not be substituted, and is selected from the group consisting of when two or more substituents T are present, the two or more substituents T are the same as or different from each other. ) 【Chemical Formula 6】 (In the formula (E411), X 41 is N(R 429 ), an oxygen atom, or a sulfur atom. R 421 ~R 429 One of them is a single bond with L 41 or L 45 and represents a single bond, R 421 to R 429 at least one set consisting of two or more adjacent ones among them is bond to each other to form a monocyclic ring which may or may not be substituted, bond to each other to form a condensed ring which may or may not be substituted, or do not bond to each other, L 41 or L 45 does not represent a single bond with, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted condensed ring, and R 421 ~R 429 are each independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, which may or may not be substituted, an alkenyl group having 2 to 50 carbon atoms, which may or may not be substituted, an alkynyl group having 2 to 50 carbon atoms, which may or may not be substituted, a cycloalkyl group having 3 to 50 carbon atoms in the ring, which may or may not be substituted, -Si(R 911 )(R 912 )(R 913 ) group represented by -O-(R 914 ) group, -S-(R 915 ) group represented by -N(R 916 )(R 917 ) group represented by -P(=O)(R 918 )(R 919 ) group represented by a halogen atom, a cyano group, a nitro group, an aryl group having 6 to 50 carbon atoms in the ring, which may or may not be substituted, and a heterocyclic group having 5 to 50 ring-forming atoms, which may or may not be substituted and does not contain a nitrogen atom, and is selected from the group consisting of. ) (In the formula (E412), X 42 is N(R 437 ), an oxygen atom, or a sulfur atom. R 431 to R 437 One of them is L 41 or L 45 represents a single bond with, R 431 ~R 437 Among them, one or more sets consisting of two or more adjacent ones of them are bond to each other to form a monocyclic ring which may or may not be substituted, bond to each other to form a condensed ring which may or may not be substituted, or do not bond to each other, L 41 or L 45 does not represent a single bond with, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring, R 431 ~R 437 each independently is a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, which may or may not be substituted, an alkenyl group having 2 to 50 carbon atoms, which may or may not be substituted, an alkynyl group having 2 to 50 carbon atoms, which may or may not be substituted, a cycloalkyl group having 3 to 50 carbon atoms in the ring, which may or may not be substituted, -Si(R 911 )(R 912 )(R 913 ) group represented by -O-(R 914 ) group represented by -S-(R 915 ) group -N(R 916 )(R 917 ) group represented by -P(=O)(R 918 )(R 919 ) group represented by a halogen atom, a cyano group, a nitro group, an aryl group having 6 to 50 carbon atoms in the ring, which may or may not be substituted, and a heterocyclic group having 5 to 50 ring-forming atoms, which may or may not be substituted and does not contain a nitrogen atom, and is selected from the group consisting of. ) (In the above formulas (E41), (E411) and (E412), R 911 ~R 919 are each independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, which may or may not be substituted, a cycloalkyl group having 3 to 50 carbon atoms in the ring, which may or may not be substituted, an aryl group having 6 to 50 carbon atoms in the ring, which may or may not be substituted, or a heterocyclic group having 5 to 50 ring-forming atoms, which may or may not be substituted and does not contain a nitrogen atom, R 911 If there are a plurality of R's 911 they may be the same as or different from each other R 912 When there are a plurality of R's 912 they may be the same as or different from each other R 913 When there are a plurality of R's 913 they may be the same as or different from each other R 914 When there are a plurality of R's 914 they may be the same as or different from each other R 915 If there are a plurality of R's 915 they may be the same as or different from each other R 916 When there are a plurality of R's 916 they may be the same as or different from each other R 917 When there are a plurality of R's 917 they may be the same as or different from each other R 918 When there are a plurality of R's 918 they may be the same as or different from each other R 919 When there are a plurality of R's 919 they may be the same as or different from each other.)
24. The first electron transport band material is a compound represented by the following formula (E42), The organic electroluminescence element according to claim 22. 【Chemical Formula 7】 (In the formula (E42), X 2 , X 4 , X 6 , L 41 , L 43 , L 45 , Ar 41 and Ar 45 respectively represent X in the formula (E1). 2 , X 4 , X 6 , L 41 , L 43 , L 45 , Ar 41 and Ar 45 is synonymous with m 1 , m 3 , m 31 and m 5 Each of them represents m in the formula (E1). 1 , m 3 , m 31 and m 5 is synonymous with R 4001 to R 4008 at least one set consisting of two or more adjacent ones among them is bond to each other to form a monocyclic ring which may or may not be substituted, bond to each other to form a condensed ring which may or may not be substituted, or do not bond to each other, R 4009 and R which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring 4001 to R 4008 are each independently a hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 911 )(R 912 )(R 913 ) group represented by -O-(R 914 ) group represented by -S-(R 915 ) group represented by A substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 920 a group represented by -COOR 921 a group represented by A halogen atom, A cyano group, A nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, However, R 4009 , and R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 4001 ~R 4008 at least one of is a single bond with *4, *4 indicates the bonding position with the carbazole ring in the formula (E42). However, when 4001 ~R 4008 one or more pairs of two or more adjacent ones among form the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted condensed ring, *4 in the formula (E42) indicates the bonding position with the mother skeleton of the formed ring structure.) (In the formula (E42), R 911 , R 912 , R 913 , R 914 , R 915 , R 920 and R 921 are each synonymous with R 911 , R 912 , R 913 , R 914 , R 915 , R 920 and R 921 in the formula (E4).)
25. The first electron transport band material is a compound represented by the following formula (E43). The organic electroluminescence element according to claim 22. 【Chemical Formula 8】 (In the formula (E43), X 2 , X 4 , X 6 , L 41 , L 43 , L 45 , Ar 41 and Ar 45 respectively represent X in the formula (E1). 2 , X 4 , X 6 , L 41 , L 43 , L 45 , Ar 41 and Ar 45 is synonymous with m 1 , m 3 , m 31 and m 5 Each of them represents m in the formula (E1). 1 , m 3 , m 31 and m 5 is synonymous with R 5001 ~R 5008 Among them, one or more sets consisting of two or more adjacent ones of them are Combined with each other to form a substituted or unsubstituted monocyclic ring, Combined with each other to form a substituted or unsubstituted condensed ring, or Not combined with each other, R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 5001 ~R 5008 are each independently A hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 911 )(R 912 )(R 913 ) group represented by -O-(R 914 ) group represented by -S-(R 915 ) group represented by A substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 920 a group represented by -COOR 921 a group represented by A halogen atom, A cyano group, A nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, However, R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 5001 ~R 5008 at least one of which is a single bond with *5, *5 indicates the bonding position with the dibenzofuran ring in the formula (E43). However, R 5001 ~R 5008 If one or more of the groups consisting of two or more adjacent ones among them form the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted condensed ring, *5 in the formula (E43) indicates the bonding position with the parent skeleton of the formed ring structure.) (In the above formula (E43), R 911 , R 912 , R 913 , R 914 , R 915 , R 920 and R 921 are each synonymous with R 911 , R 912 , R 913 , R 914 , R 915 , R 920 and R 921 in the above formula (E4). )
26. The first electron transport band material is a compound represented by the following formula (E44). The organic electroluminescence element according to claim 22. 【Chemical Formula 9】 (In the formula (E44), X 2 , X 4 , X 6 , L 41 , L 43 , L 45 , Ar 41 and Ar 45 respectively represent X in the formula (E1). 2 , X 4 , X 6 , L 41 , L 43 , L 45 , Ar 41 and Ar 45 is synonymous with m 1 , m 3 , m 31 and m 5 Each of them represents m in the formula (E1). 1 , m 3 , m 31 and m 5 is synonymous with R 6009 and R 6010 the set consisting of Combined with each other to form a substituted or unsubstituted monocyclic ring, Combined with each other to form a substituted or unsubstituted condensed ring, or Not combined with each other, R 6001 ~R 6008 Among them, one or more sets consisting of two or more adjacent ones are Combined with each other to form a substituted or unsubstituted monocyclic ring, Combined with each other to form a substituted or unsubstituted condensed ring, or Not combined with each other, R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 5001 ~R 5010 are each independently A hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 911 )(R 912 )(R 913 ) group represented by -O-(R 914 ) group represented by -S-(R 915 ) group represented by A substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 920 a group represented by -COOR 921 a group represented by A halogen atom, A cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, However, R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 6001 ~R 6010 at least one of which is a single bond with *6, *6 indicates the bonding position with the dibenzofuran ring in the formula (E44). However, R 6001 ~R 6010 When one or more of the groups consisting of two or more adjacent ones among them form the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted condensed ring, *6 in the formula (E44) indicates the bonding position with the mother skeleton of the formed ring structure.) (In the formula (E44), R 911 , R 912 , R 913 , R 914 , R 915 , R 920 and R 921 are respectively synonymous with R 911 , R 912 , R 913 , R 914 , R 915 , R 920 and R 921 in the formula (E4).)
27. The first electron transport band material is a compound represented by the following formula (E5). The organic electroluminescence element according to any one of Claims 13, 17, and 18. 【Chemical Formula 10】 (In the formula (E5), one or more of the groups consisting of two or more adjacent groups among R 501 ~R 508 are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 501 ~R 508 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -O-(R 904 ) group -S-(R 905 ) group represented by a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a carboxy group, -N(R 905N )(R 906N ) group, or a group represented by the formula (E51), when there are a plurality of groups represented by the formula (E51), the plurality of groups represented by the formula (E51) are the same as or different from each other, L 501 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 ring-forming atoms which is substituted or unsubstituted, HAR 501 is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, mb is 1, 2, 3, or 4, when mb is 2, 3, or 4, L of 2 or more 501 are identical to each other or different from each other, Two or more HARs 501 are identical to or different from each other, In the formula (E51), * indicates the bonding position with the phenanthroline ring in the formula (E5). However, when one or more of the groups R 501 ~R 508 form one or more sets of two or more adjacent groups to form the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted condensed ring, * in the formula (E51) indicates the bonding position with the parent skeleton of the formed ring structure.) (In the formula (E5), R 904 and R 905 are each independently, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 904 When there are a plurality of R's 904 they may be the same as or different from each other R 905 When there are a plurality of R's 905 they may be the same as or different from each other R 905N and R 906N each independently is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, R 905N When there are a plurality of R's 905N they may be the same as or different from each other R 906N When there are a plurality of R's 906N they may be the same as or different from each other.)
28. R 501 ~R 508 at least one of which is a group represented by the formula (E51), The group represented by the formula (E51) is a group represented by any one of the following formulas (E511) to (E515). The organic electroluminescence element according to Claim 27. 【Chemical 11】 (In the formula (E511), R 511 , R 512 , R 513 , R 514 and R 515 any one of which represents a single bond with L 501 and In the formula (E512), R 516 , R 517 , R 518 and R 519 , any one of them represents a single bond with L 501 , In the formula (E513), R 520 , R 521 and R 522 any one of which represents a single bond with L 501 and In the formula (E514), R 523 , R 524 , R 525 and R 526 Any one of represents a single bond with L 501 and In the formula (E515), R 527 , R 528 , R 529 and R 530 any one of represents a single bond with L 501 and, R 511 to R 530 one or more of the sets, each set consisting of two or more adjacent ones among them, bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, L 501 does not represent a single bond with, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring R 511 ~R 530 each independently is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A cycloalkyl group having 3 to 50 ring-forming carbon atoms, which may or may not be substituted, An aralkyl group having 7 to 50 carbon atoms, which may or may not be substituted, -O-(R 904 ) group -S-(R 905 ) group represented by An alkoxycarbonyl group having 1 to 50 carbon atoms, which may or may not be substituted, A halogen atom, a cyano group, a nitro group, a carboxy group, or -N(R 905N )(R 906N ) is a group represented by, R 904 、R 905 、R 905N and R 906N are, respectively, R 904 、R 905 、R 905N and R 906N in the formula (E5), respectively, and * represents the bonding position.)
29. R 501 to R 508 at least one of which is a group represented by the formula (E51), The group represented by the formula (E51) is a group represented by any one of the following formulas (E516) to (E529). The organic electroluminescence element according to claim 27. 【Chemical Formula 12】 【Chemical 13】 (In the formulas (E516) to (E525), R E Any one of them is a single bond with L 501 and represents a single bond with L A plurality of Rs E at least one set consisting of two or more adjacent ones among them is Combined with each other to form a substituted or unsubstituted monocyclic ring, Combined with each other to form a substituted or unsubstituted condensed ring, or Not combined with each other, L 501 R which does not represent a single bond with said L, does not form said substituted or unsubstituted monocyclic ring, and does not form said substituted or unsubstituted condensed ring E each independently, in said formulas (E511) to (E515), is R which does not represent a single bond with L 501 R which does not represent a single bond with said L, does not form said substituted or unsubstituted monocyclic ring, and does not form said substituted or unsubstituted condensed ring 511 to R 530 is synonymous with A plurality of Rs E are the same as or different from each other, and * represents a bonding position.)
30. The first electron transport band material is a compound represented by the following formula (E61) or (E62). The organic electroluminescence element according to any one of claims 13, 17, and 18. 【Chemical 14】 (In the formulas (E61) and (E62), Cz is independently a carbazolyl group or an indolyl group represented by any one of the following formulas (E63), (E64), (E65), (E66), (E67), and (E68), L 6 are each independently A single bond, A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, pa is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, pb is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, L 6 When there are a plurality of Ls 6 they are identical to each other or different When a plurality of Cz are present, the plurality of Cz are the same as or different from each other, FA is independently a condensed ring group having 6 to 50 ring-forming carbon atoms, which may or may not be substituted, provided that FA is not an unsubstituted carbazolyl group.) 【Chemical Formula 15】 (In the formulas (E63), (E64), (E65), (E66), (E67), and (E68), Z 6 is, independently of each other, a single bond, -C(R 601 )(R 602 )-, -Si(R 603 )(R 604 )-, -O-, -CO-, or -N(R 605 )-, and R 601 、R 602 、R 603 、R 604 and R 605 are each independently A hydrogen atom, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, or A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Ring E is independently A substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 ring-forming carbon atoms, A substituted or unsubstituted nitrogen atom-containing non-aromatic heterocyclic ring having 3 to 20 ring-forming atoms, A substituted or unsubstituted aromatic hydrocarbon ring having 4 to 50 ring-forming carbon atoms, or A substituted or unsubstituted aromatic heterocyclic ring having 4 to 50 ring-forming atoms, a is 3, b is, independently of each other, 0, 1, 2, 3 or 4, c is 4, d is 2, e is 1, A plurality of Rs 6 one or more sets, each set consisting of two or more adjacent ones among them, which are bonded to each other to form a substituted or unsubstituted monocyclic ring, which are bonded to each other to form a substituted or unsubstituted condensed ring, or which are not bonded to each other, R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 6 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, -O-(R 904 ) group represented by -S-(R 905 ) group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a carboxy group, a halogen atom, a cyano group or a nitro group, A plurality of Rs 601 are identical to or different from each other, A plurality of Rs 602 are identical to or different from each other, A plurality of Rs 603 are identical to or different from each other, A plurality of Rs 604 are identical to or different from each other, A plurality of Rs 605 are identical to or different from each other, A plurality of Rs 6 are identical to or different from each other. * represents a bonding position.) (In the compound represented by the formula (E61) or (E62), R 904 and R 905 are each independently, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 904 When there are a plurality of R's 904 they may be the same as or different from each other R 905 When there are a plurality of R's 905 they may be the same as or different from each other.)
31. The group represented by the formula (E63) is a group represented by any one of the formulas consisting of the following formulas (E631), (E632), (E633) and (E634), The organic electroluminescence element according to claim 30. 【Chemical 16】 【Chemical 17】 (R in the formulas (E631), (E632), (E633) and (E634) 6 and a are respectively synonymous with R in the formula (E63) 6 and a, bx is 4, by is 3, and R 61 to R 68 are each independently synonymous with R in the formula (E63) 6 and a plurality of R 6 are the same as or different from each other, and * represents the bonding position.)
32. The group represented by the formula (E65) is a group represented by any one of the formulas consisting of the following formulas (E651), (E652), (E653) and (E654), The organic electroluminescence element according to claim 30. 【Chemical Formula 18】 【Chemical Formula 19】 (In the formulas (E651), (E652), (E653) and (E654), R 6 and c are respectively synonymous with R 6 and c in the formula (E65), bx is 4, by is 3, R 61 to R 68 are each independently synonymous with R 6 in the formula (E65), a plurality of R 6 are the same as or different from each other, and * represents a bonding position.)
33. The first electron transport band material is a compound represented by the following formula (E7), The organic electroluminescence element according to any one of claims 13, 17 and 18. 【Chemical 20】 (In the formula (E7), R 701 ~R 710 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by -O-(R 904 ) group represented by -S-(R 905 ) group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 a group represented by -COOR 802 a group represented by a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, or a group represented by the formula (E71), However, R 701 ~R 710 at least one of which is a group represented by the formula (E71), When there are a plurality of groups represented by the formula (E71), the plurality of groups represented by the formula (E71) are the same as or different from each other, L 701 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, Ar 701 is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, mx7 is 0, 1, 2, 3, 4 or 5, provided that when mx7 is 0, -(L 701 ) 0 - is a single bond, L 701 When there are two or more Ls 701 they may be the same as or different from each other Ar 701 When two or more Ar are present, the two or more Ar 701 are the same as or different from each other, * in the formula (E71) indicates the bonding position with the ring represented by the formula (E7).) (In the compound represented by the formula (E7), R 901 , R 902 , R 903 , R 904 , R 905 , R 801 and R 802 are each independently, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901 When there are a plurality of R's 901 they may be the same as or different from each other R 902 When there are a plurality of R's 902 they may be the same as or different from each other R 903 When there are a plurality of R's 903 they may be the same as or different from each other R 904 If there are a plurality of R's, 904 the plurality of R's are the same as or different from each other, R 905 When there are a plurality of R's 905 they may be the same as or different from each other R 801 When there are a plurality of R's, the plurality of R's 801 are the same as or different from each other, R 802 When there are a plurality of R's 802 they may be the same as or different from each other.)
34. The refractive index of the organic material contained in the first charge generation layer is 1.83 or less, The organic electroluminescence device according to claim 18.
35. The first charge generation band further includes a second charge generation layer, The second charge generation layer is disposed between the first charge generation layer and the second light emission band, The organic electroluminescence device according to any one of claims 5 to 34.
36. When the organic electroluminescence device satisfies the condition (TDM1), the at least two low refractive index layers in direct contact in the condition (TDM1) include the first charge generation layer and the second charge generation layer, The organic electroluminescence device according to claim 35.
37. The first charge generation layer and the second charge generation layer are in direct contact with each other, The organic electroluminescence device according to claim 35 or 36.
38. A second hole transport layer is disposed between the second charge generation layer and the second light emission band, The organic electroluminescence device according to any one of claims 35 to 37.
39. The second hole transport layer is the low refractive index layer, The organic electroluminescence device according to claim 38.
40. The total of the film thickness of the first charge generation layer, the film thickness of the second charge generation layer, and the film thickness of the second hole transport layer is 50 nm or more, The organic electroluminescence device according to claim 38 or 39.
41. The second hole transport layer contains a second hole transport band material. The organic electroluminescence device according to any one of claims 38 to 40.
42. The refractive index of the second hole transport band material is 1.83 or less. The organic electroluminescence device according to claim 41.
43. The second hole transport band material is a compound represented by the following formula (B10). The organic electroluminescence device according to claim 41 or claim 42. 【Chemical 21】 (In the formula (B100), L 11 、 L 12 and L 13 are each independently A single bond, A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, A divalent heterocyclic group having 5 to 50 ring-forming atoms which may be substituted or unsubstituted, or A divalent group in which two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms are bonded, A 1 、B 1 、and C 1 are each independently A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, -Si(R C1 )(R C2 )(R C3 ) group, or A group represented by the formula (1G), However, at least one selected from the group consisting of A 1 , B 1 , and C 1 is a group represented by the formula (1G). R C1 , R C2 and R C3 are each independently A hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R C1 When there are a plurality of R's C1 they may be the same as each other or different R C2 When there are a plurality of R's C2 they may be identical to each other or different R C3 If there are a plurality of R's C3 they may be the same as or different from each other In the formula (1G), X B is a single bond, an oxygen atom, a sulfur atom, N(R B11 ), or C(R B12 )(R B13 ), and X B If there are a plurality of Xs B they are identical to or different from each other X B is C(R B12 )(R B13 )), when R B12 and R B13 form a pair consisting of They are bonded to each other to form a substituted or unsubstituted monocyclic ring, They are bonded to each other to form a substituted or unsubstituted condensed ring, or They are not bonded to each other, R B1 、 R B2 、 R B3 、 R B4 、 R B5 、 R B6 、 R B7 、 R B8 、 R B9 、 R B10 、 R B11 、 R B12 and R B13 One of them is a single bond that binds to *1, A non-single bond R that binds to *1 B1 R B2 R B3 R B4 R B5 R B6 R B7 R B8 and R B11 are each independently A hydrogen atom, A cyano group, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by -O-(R 904 ) group represented by A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R B9 and R B10 constitute a set that They are bonded to each other to form a substituted or unsubstituted monocyclic ring, They are bonded to each other to form a substituted or unsubstituted condensed ring, or They are not bonded to each other, R which is not a single bond connecting to *1, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted condensed ring B9 , R B10 , R B12 and R B13 are each independently A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, or A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, *2 is the coupling position with L 11 , L 12 or L 13 and is the coupling position with When two or more groups represented by the formula (1G) are present, the two or more groups represented by the formula (1G) are the same as or different from each other. ) (In the compound represented by the formula (B100), R 901 , R 902 , R 903 and R 904 are each independently, A hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901 When there are a plurality of R's 901 they may be the same as or different from each other R 902 When there are a plurality of R's 902 they may be the same as or different from each other R 903 When there are a plurality of R's 903 they may be the same as or different from each other R 904 When there are a plurality of R's 904 they may be the same as or different from each other.)
44. The organic electroluminescence element satisfies the condition (TDM1), and the at least two low refractive index layers directly in contact in the condition (TDM1) contain different compounds from each other. The organic electroluminescence element according to any one of claims 1 to 43.
45. The first emission band contains a first light-emitting compound, The second emission band contains a second light-emitting compound, The first light-emitting compound and the second light-emitting compound are the same as or different from each other, One or both of the first light-emitting compound and the second light-emitting compound is a compound that exhibits emission with a maximum peak wavelength of 500 nm or less. The organic electroluminescence element according to any one of claims 1 to 44.
46. The two or more light-emitting units further include a third light-emitting unit. The organic electroluminescence element according to any one of claims 1 to 45.
47. When the organic electroluminescence element satisfies the condition (TDM1), and the absolute value of the difference in refractive index between two organic materials selected from the group consisting of the organic materials contained in the at least two low refractive index layers directly in contact in the condition (TDM1) is Δn, at least any one of the Δn is less than 0.
10. The organic electroluminescence element according to any one of claims 1 to 46.
48. The organic electroluminescence element satisfies the condition (TDM1), and the total film thickness of the at least two low refractive index layers directly in contact in the condition (TDM1) is 100 nm or less. The organic electroluminescence element according to any one of claims 1 to 47.
49. An electronic device equipped with the organic electroluminescence element according to any one of claims 1 to 48.
Citation Information
Patent Citations
Organic electroluminescent element, organic electroluminescent display device, and electronic device
WO2022154029A1