Organic electroluminescent element and electronic device
By using a low refractive index material layer and optimizing electron transport band materials in multiple light-emitting units, the organic electroluminescence elements achieve improved light extraction and external quantum efficiency, addressing the low efficiency issues in existing technologies.
Patent Information
- Application Number
- PCT/JP2024/044374
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2023-12-27
- Filing Date
- 2024-12-16
- Publication Date
- 2025-07-03
AI Technical Summary
Existing organic electroluminescence elements suffer from low light extraction efficiency due to refractive index differences between layers, leading to reduced performance in luminance, emission wavelength, chromaticity, luminous efficiency, and lifespan.
Incorporating a configuration with a low refractive index material layer and adjusting the triplet energy and affinity of electron transport band materials in multiple light-emitting units to enhance carrier recombination probability and improve triplet-triplet fusion efficiency.
Enhances light extraction efficiency and external quantum efficiency by optimizing the electron transport layer materials, resulting in improved performance in luminance, emission wavelength, chromaticity, and lifespan of the organic electroluminescence elements.
Smart Images

Figure JP2024044374_03072025_PF_FP_ABST
Abstract
Description
Organic electroluminescence element and electronic device
[0001] The present invention relates to an organic electroluminescence element and an electronic device.
[0002] Organic electroluminescent devices (hereinafter sometimes referred to as "organic EL devices") are used in full-color displays such as mobile phones and televisions. When a voltage is applied to an organic EL device, holes are injected into the light-emitting layer from the anode, and electrons are injected into the light-emitting layer from the cathode. The injected holes and electrons then recombine in the light-emitting layer to form excitons. According to the statistical law of electron spin, singlet excitons are generated at a rate of 25% and triplet excitons at a rate of 75%. The performance of organic EL devices includes, for example, brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime. One of the challenges of organic EL devices is their low light extraction efficiency. In particular, attenuation due to reflection caused by differences in the refractive index of adjacent layers is a major factor in reducing the light extraction efficiency of organic EL devices. To mitigate this effect, organic EL device configurations have been proposed that include layers made of low-refractive-index materials.
[0003] In order to improve the performance of organic EL elements, for example, Patent Document 1 considers stacking a plurality of hole transport layers. Furthermore, Patent Document 2 describes a phenomenon in which singlet excitons are generated by the collision and fusion of two triplet excitons (hereinafter, this phenomenon may be referred to as the triplet-triplet fusion (TTF) phenomenon) in order to improve the performance of organic EL elements. Examples of the performance of organic EL elements include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime.
[0004] International Publication No. WO 2022 / 154029 International Publication No. WO 2010 / 134350
[0005] Further improvements in performance (for example, improvements in external quantum efficiency) are required for organic EL elements. An object of the present invention is to provide an organic electroluminescent element capable of improving external quantum efficiency, and to provide an electronic device equipped with the organic electroluminescent element.
[0006] According to one aspect of the present invention, there is provided an organic electroluminescent element, the organic electroluminescent element having 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 including at least a first light-emitting unit and a second light-emitting unit, the first light-emitting unit and the second light-emitting unit being disposed in this order from the anode side toward the cathode side, the first light-emitting unit including a first light-emitting band, the second light-emitting unit including a second light-emitting band, and the first light-emitting band and the second light-emitting band a first electron-transporting region is disposed between the first and second emission regions, the first electron-transporting region including one or more layers, one of which is an emitter-side electron-transporting layer that is in direct contact with the first emission region; a cathode-side electron-transporting layer is disposed between the first electron-transporting region and the second emission region, the emitter-side electron-transporting layer containing a first electron-transporting region material, and the first electron-transporting region material satisfies the following mathematical formulas (Mathematical Formula 1) and (Mathematical Formula 2). 1 (E1) ≧ 1.90 eV (Equation 1) Af(E1) ≧ 1.55 eV (Equation 2) (T 1 (E1) is the triplet energy of the first electron transporting band material, and Af(E1) is the affinity of the first electron transporting band material.
[0007] According to one aspect of the present invention, there is provided an organic electroluminescence device comprising an anode, a cathode, and a first emission zone disposed between the anode and the cathode, wherein a first electron-transport zone is disposed between the first emission zone and the cathode, the first electron-transport zone including one or more layers, one of which is an emission-layer-side electron-transport layer in direct contact with the first emission zone, and a cathode-side electron-transport layer is disposed between the first electron-transport zone and the cathode, the emission-layer-side electron-transport layer containing a first electron-transport zone material, and the first electron-transport zone material being a compound having a fused polycyclic skeleton, and satisfying the following mathematical formulas (Mathematical Formula 1) and (Mathematical Formula 2). 1(E1) ≧ 1.90 eV (Equation 1) Af(E1) ≧ 1.55 eV (Equation 2) (T 1 (E1) is the triplet energy of the first electron transporting band material, and Af(E1) is the affinity of the first electron transporting band material.
[0008] According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescence element according to one aspect of the present invention.
[0009] According to one aspect of the present invention, it is possible to provide an organic electroluminescence element capable of improving external quantum efficiency, and an electronic device equipped with the organic electroluminescence element.
[0010] 1 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a first embodiment of the present invention, and FIG. 2 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a second embodiment of the present invention.
[0011] [Definitions] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.
[0012] In this specification, in a chemical structural formula, a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is assumed to be bonded to a possible bonding position that is not explicitly indicated with a symbol such as "R" or "D" representing a deuterium atom.
[0013] As used herein, the term "number of ring 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 bonded in a ring (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. For example, a 9,9-diphenylfluorenyl group has 13 ring carbon atoms, and a 9,9'-spirobifluorenyl group has 25 ring carbon atoms. When a benzene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Therefore, the number of ring carbon atoms of a benzene ring substituted with an alkyl group is 6. Furthermore, when the naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.
[0014] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, and a ring assembly). Atoms that do not constitute the ring (e.g., hydrogen atoms terminating the bonds of atoms constituting the ring) and atoms contained in the substituent when the ring is substituted with a substituent are not included in the number of ring atoms. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms or atoms constituting a substituent bonded to the pyridine ring is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. Furthermore, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring, so the number of ring atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.
[0015] In this specification, the "number of carbon atoms XX to YY" in the expression "substituted or unsubstituted ZZ group having carbon atoms XX to YY" represents the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent 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, the "number of atoms XX to YY" in the expression "substituted or unsubstituted ZZ group having number of atoms XX to YY" refers to 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 refers to the case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to 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 is not replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protist atom, a deuterium atom, or a tritium atom. Furthermore, 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 are replaced with 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 are replaced with an AA group.
[0018] "Substituents Described in This Specification" The substituents described in this specification are explained below.
[0019] The number of ring carbon atoms of an "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring atoms of an "unsubstituted heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms of an "unsubstituted alkyl group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein. The number of carbon atoms of an "unsubstituted alkenyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of carbon atoms of an "unsubstituted alkynyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of ring carbon atoms of an "unsubstituted cycloalkyl group" described herein is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified herein. Unless otherwise specified herein, the number of ring carbon atoms of an "unsubstituted arylene group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18. Unless otherwise specified herein, the number of ring atoms of an "unsubstituted divalent heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18. Unless otherwise specified herein, the number of carbon atoms of an "unsubstituted alkylene group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.
[0020] "Substituted or Unsubstituted Aryl Group" Specific examples (Specific Example Group G1) of the "substituted or unsubstituted aryl group" described herein include the following unsubstituted aryl group (Specific Example Group G1A) and substituted aryl group (Specific Example Group G1B). (Here, an unsubstituted aryl group refers to a case where a "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and a substituted aryl group refers to a case where a "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" simply refers to both an "unsubstituted aryl group" and a "substituted aryl group." A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with substituents. Examples of the "substituted aryl group" include a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with substituents in the "unsubstituted aryl group" of the following Specific Example Group G1A, and examples of the substituted aryl group of the following Specific Example Group G1B. It should be noted that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and the "substituted aryl groups" described in this specification also include groups in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl groups" of the following specific example group G1B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted aryl groups" of the following specific example group G1B is further replaced with a substituent.
[0021] Unsubstituted aryl groups (specific example group G1A): a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a benzanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a triphenylenyl group, a benzotriphenylenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, A 9,9'-spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a fluoranthenyl group, a benzofluoranthenyl group, a perylenyl group, and a monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).
[0022]
[0023]
[0024] Substituted aryl groups (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 a ring structure represented by the above general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.
[0025] "Substituted or Unsubstituted Heterocyclic Group" The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom among the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom. The "heterocyclic group" described herein is a monocyclic group or a fused ring group. The "heterocyclic group" described herein 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 herein include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (Here, an unsubstituted heterocyclic group refers to when a "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and a substituted heterocyclic group refers to when a "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when simply referring to a "heterocyclic group", it includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group". A "substituted heterocyclic group" means a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with substituents. Specific examples of the "substituted heterocyclic group" include groups in which hydrogen atoms of an "unsubstituted heterocyclic group" in the following specific example group G2A are replaced, and examples of substituted heterocyclic groups in the following specific example group G2B. The examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic groups" described in this specification also include groups in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic groups" of specific example group G2B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted heterocyclic groups" of specific example group G2B is further replaced with a substituent.
[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 ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).
[0027] Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) are replaced with substituents (specific example group G2B4).
[0028] Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolidinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, an indazolyl group, a phenanthrolinyl group, a phenanthridinyl group, an acridinyl group, a phenazinyl group, a carbazolyl group, Benzocarbazolyl group, morpholino group, phenoxazinyl group, phenothiazinyl group, azacarbazolyl group, and diazacarbazolyl group.
[0029] Unsubstituted heterocyclic groups 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 benzisoxazolyl group, a phenoxazinyl group, a morpholino group, a dinaphthofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, an azanaphthobenzofuranyl group, and a diazanaphthobenzofuranyl group.
[0030] Unsubstituted heterocyclic groups 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 benzisothiazolyl group, a phenothiazinyl group, a dinaphthothiophenyl group (dinaphthothienyl group), an azadibenzothiophenyl group (azadibenzothienyl group), a diazadibenzothiophenyl group (diazadibenzothienyl group), an azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and a diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).
[0031] Monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4):
[0032]
[0033]
[0034] In the general formulae (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH 2 However, X A and Y A At least one of X is an oxygen atom, a sulfur atom, or NH. A and Y A At least one of the groups is NH or CH 2 In this case, the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) may contain any of these NH, CH 2 and monovalent groups obtained by removing one hydrogen atom from the group consisting of:
[0035] Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): a (9-phenyl)carbazolyl group, a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a (9-naphthyl)carbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a methylbenzimidazolyl group, an ethylbenzimidazolyl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenylquinazolinyl group, and a biphenylylquinazolinyl group.
[0036] Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): a phenyldibenzofuranyl group, a methyldibenzofuranyl group, a t-butyldibenzofuranyl group, and a monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].
[0037] Substituted heterocyclic groups containing a sulfur atom (specific example group G2B3): a phenyldibenzothiophenyl group, a methyldibenzothiophenyl group, a t-butyldibenzothiophenyl group, and a monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].
[0038] Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the above general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4):
[0039] The "one or more hydrogen atoms of the monovalent heterocyclic group" refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, X A and Y A a hydrogen atom bonded to a nitrogen atom when at least one of A and Y A One of them is CH 2 and n is 0 or more. The methylene group in the formula (I) is one or more hydrogen atoms selected from the hydrogen atoms of the methylene group in the formula (I).
[0040] "Substituted or Unsubstituted Alkyl Group" Specific examples (Specific Example Group G3) of the "substituted or unsubstituted alkyl group" described herein include the following unsubstituted alkyl group (Specific Example Group G3A) and substituted alkyl group (Specific Example Group G3B). (Here, the term "unsubstituted alkyl group" refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and the term "substituted alkyl group" refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereinafter, the term "alkyl group" includes both an "unsubstituted alkyl group" and a "substituted alkyl group." A "substituted alkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced with substituents. Specific examples of the "substituted alkyl group" include the following "unsubstituted alkyl group" (Specific Example Group G3A) in which one or more hydrogen atoms are replaced with substituents, and the examples of the substituted alkyl group (Specific Example Group G3B). In this specification, the alkyl group in an "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the term "unsubstituted alkyl group" includes a straight-chain "unsubstituted alkyl group" and a branched "unsubstituted alkyl group." The examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed here are merely examples, and the "substituted alkyl group" described in this specification also includes groups in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" of specific example group G3B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted alkyl group" of specific example group G3B is further replaced with a substituent.
[0041] Unsubstituted alkyl groups (specific example group G3A): a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, and a t-butyl group.
[0042] Substituted alkyl groups (specific example group G3B): a heptafluoropropyl group (including isomers), a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, and a trifluoromethyl group.
[0043] "Substituted or Unsubstituted Alkenyl Group" Specific examples (Specific Example Group G4) of the "substituted or unsubstituted alkenyl group" described herein include the following unsubstituted alkenyl group (Specific Example Group G4A) and substituted alkenyl group (Specific Example Group G4B). (Here, an unsubstituted alkenyl group refers to a case where a "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and a "substituted alkenyl group" refers to a case where a "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply refers to both an "unsubstituted alkenyl group" and a "substituted alkenyl group." A "substituted alkenyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are replaced with substituents. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl groups" (specific example group G4A) having a substituent, and examples of substituted alkenyl groups (specific example group G4B). The examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed here are merely examples, and the "substituted alkenyl group" described in this specification also includes groups in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl groups" of specific example group G4B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted alkenyl groups" of specific example group G4B is further replaced with a substituent.
[0044] Unsubstituted alkenyl groups (specific example group G4A): a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, and a 3-butenyl group.
[0045] Substituted alkenyl groups (specific example group G4B): a 1,3-butadienyl group, a 1-methylvinyl group, a 1-methylallyl group, a 1,1-dimethylallyl group, a 2-methylallyl group, and a 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 group (specific example group G5A). (Here, an unsubstituted alkynyl group refers to a case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, the term "alkynyl group" includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group." A "substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" have been replaced with a substituent. Specific examples of the "substituted alkynyl group" include a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" (specific example group G5A) have been replaced with a substituent.
[0047] Unsubstituted alkynyl groups (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 herein include the following unsubstituted cycloalkyl group (Specific Example Group G6A) and substituted cycloalkyl group (Specific Example Group G6B). (Here, the term "unsubstituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group," and the term "substituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group.") In this specification, the term "cycloalkyl group" simply refers to both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group." A "substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced with substituents. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (Specific Example Group G6A) in which one or more hydrogen atoms are replaced with substituents, and the examples of the substituted cycloalkyl group (Specific Example Group G6B). The examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed here are merely examples, and the "substituted cycloalkyl groups" described in this specification also include groups in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl groups" of specific example group G6B are replaced with substituents, and groups in which a hydrogen atom of a substituent in the "substituted cycloalkyl groups" of specific example group G6B is further replaced with a substituent.
[0049] Unsubstituted cycloalkyl groups (specific example group G6A): a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a 2-norbornyl group.
[0050] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.
[0051] -Si(R 901 ) (R 902 ) (R 903 A group represented by —Si(R 901 ) (R 902) (R 903 Specific examples (specific example group G7) of the group represented by the formula (G1) 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). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. The multiple G1s in -Si(G1)(G1)(G1) may be the same or different. - Multiple G2 in Si(G1)(G2)(G2) are the same as or different from each other. - Multiple G1 in Si(G1)(G1)(G2) are the same as or different from each other. - Multiple G2 in Si(G2)(G2)(G2) are the same as or different from each other. - Multiple G3 in Si(G3)(G3)(G3) are the same as or different from each other. - Multiple G6 in Si(G6)(G6)(G6) are the same as or different from each other.
[0052] ・「-O-(R 904 A group represented by —O—(R 904 ) (Specific example group G8) includes -O(G1), -O(G2), -O(G3), and -O(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
[0053] ・"-S-(R 905 A group represented by —S—(R 905) (Specific example group G9) includes -S(G1), -S(G2), -S(G3), and -S(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
[0054] ・「-N(R 906 ) (R 907 A group represented by —N(R 906 ) (R 907 Specific examples (specific example group G10) of groups represented by the formula (G1) include -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. Multiple G1s in -N(G1)(G1) may be the same as or different from one another. Multiple G2s in -N(G2)(G2) may be the same as or different from one another. Multiple G3s in -N(G3)(G3) may be the same as or different from one another. The multiple G6s 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, and an iodine atom.
[0056] "Substituted or unsubstituted fluoroalkyl group" As used herein, a "substituted or unsubstituted fluoroalkyl group" refers to 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 with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). Unless otherwise specified herein, the number of carbon atoms in an "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. A "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. Note that the "substituted fluoroalkyl group" described herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in a "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include the examples of the above-mentioned "alkyl group" (specific example group G3) in which one or more hydrogen atoms have been replaced with fluorine atoms.
[0057] "Substituted or unsubstituted haloalkyl group" As used herein, a "substituted or unsubstituted haloalkyl group" refers to 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 with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The number of carbon atoms in an "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. A "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of a "haloalkyl group" are replaced with a substituent. Note that the "substituted haloalkyl group" described herein also includes a "substituted haloalkyl group" in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain are further replaced with a substituent, and a "substituted haloalkyl group" in which one or more hydrogen atoms of the substituent are further replaced with a substituent. Specific examples of the "unsubstituted haloalkyl group" include the examples of the above-mentioned "alkyl group" (specific example group G3) in which one or more hydrogen atoms are replaced with halogen atoms. A haloalkyl group may also be referred to as a halogenated alkyl group.
[0058] - "Substituted or unsubstituted alkoxy group" A specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.
[0059] - "Substituted or unsubstituted alkylthio group" A specific example of the "substituted or unsubstituted alkylthio group" described in this specification is a group represented by -S(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.
[0060] - "Substituted or unsubstituted aryloxy group" A specific example of the "substituted or unsubstituted aryloxy group" described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. Unless otherwise specified in this specification, the number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.
[0061] - "Substituted or unsubstituted arylthio group" A specific example of the "substituted or unsubstituted arylthio group" described in this specification is a group represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. Unless otherwise specified in this specification, the number of ring carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.
[0062] - "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Multiple G3s in -Si(G3)(G3)(G3) are the same as or different from one another. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.
[0063] "Substituted or unsubstituted aralkyl group" A specific example of the "substituted or unsubstituted aralkyl group" described in this specification is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3, and G1 is a "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 one embodiment 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 in 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, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group, an α-naphthylmethyl group, a 1-α-naphthylethyl group, a 2-α-naphthylethyl group, a 1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, a β-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethyl group, a 1-β-naphthylisopropyl group, and a 2-β-naphthylisopropyl group.
[0064] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described in this specification is preferably a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, or the like.
[0065] Unless otherwise specified in this specification, 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 (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 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 aza Examples of such groups include a dibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group (a (9-phenyl)carbazol-1-yl group, a (9-phenyl)carbazol-2-yl group, a (9-phenyl)carbazol-3-yl group, or a (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.
[0066] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.
[0067]
[0068] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically any of the following groups:
[0069]
[0070] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.
[0071] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.
[0072]
[0073] In the general formulae (TEMP-34) to (TEMP-41), * represents a bonding position.
[0074] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, and the like.
[0075] "Substituted or unsubstituted arylene group" Unless otherwise specified, 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-mentioned "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, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom on the heterocycle from the above-mentioned "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 heterocycle 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.
[0078] Unless otherwise specified in the present specification, the substituted or unsubstituted arylene group described in the present specification is preferably any one of the groups represented by the following general formulae (TEMP-42) to (TEMP-68).
[0079]
[0080]
[0081] In the general formulae (TEMP-42) to (TEMP-52), Q 1 ~Q 10 are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-42) to (TEMP-52), * represents a bonding position.
[0082]
[0083] In the general formulae (TEMP-53) to (TEMP-62), Q 1 ~Q 10 are each independently a hydrogen atom or a substituent. 9 and Q 10 may be bonded to each other via a single bond to form a ring. In the general formulae (TEMP-53) to (TEMP-62), * represents the bonding position.
[0084]
[0085] In the general formulae (TEMP-63) to (TEMP-68), Q 1 ~Q 8 are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-63) to (TEMP-68), * represents a bonding position.
[0086] Unless otherwise specified in the present specification, the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the groups represented by the following general formulae (TEMP-69) to (TEMP-102).
[0087]
[0088]
[0089]
[0090] In the general formulae (TEMP-69) to (TEMP-82), Q 1 ~Q 9 are each independently a hydrogen atom or a substituent.
[0091]
[0092]
[0093]
[0094]
[0095] In the general formulae (TEMP-83) to (TEMP-102), Q 1 ~Q 8 are each independently a hydrogen atom or a substituent.
[0096] The above is the explanation of "substituents described in this specification."
[0097] "When bonded to form a ring" In this specification, when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle, bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other," it means when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle," when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring," and when "one or more pairs of adjacent groups do not bond to each other." In this specification, the cases when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle" and "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "when bonded to form a ring") will be explained below. An anthracene compound represented by the following general formula (TEMP-103), in which the main skeleton is an anthracene ring, will be described as an example.
[0098]
[0099] For example, R 921~R 930 In the case where "one or more pairs of adjacent two or more groups are bonded to each other to form a ring," the pair of adjacent two groups is R 921 and R 922 With the pair, R 922 and R 923 Paired with R 923 and R 924 With the pair, R 924 and R 930 With the pair, R 930 and R 925 With the pair, R 925 and R 926 With the pair, R 926 and R 927 Paired with R 927 and R 928 Paired with R 928 and R 929 and R 929 and R 921 It is paired with.
[0100] The above-mentioned "one or more pairs" means that two or more pairs of adjacent two or more groups may simultaneously form a ring. For example, R 921 and R 922 and are bonded to each other to form ring Q A and simultaneously form R 925 and R 926 and are bonded to each other to form ring Q B When the anthracene compound represented by the general formula (TEMP-103) is formed, the anthracene compound represented by the general formula (TEMP-104) is represented by the following general formula (TEMP-104).
[0101]
[0102] The case where a "set of two or more adjacent groups" forms a ring includes not only the case where a set of "two" adjacent groups is bonded as in the above example, but also the case where a set of "three or more" adjacent groups is bonded. For example, R 921 and R 922 and are bonded to each other to form ring Q A and R 922 and R 923 and are bonded to each other to form ring Q C and three adjacent (R 921 , R 922 and R923 In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105): A and Ring Q C is R 922 Share.
[0103]
[0104] The "monocyclic ring" or "fused ring" formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when "one pair of adjacent two" forms a "monocyclic ring" or a "fused ring", the "monocyclic ring" or the "fused ring" may form a saturated ring or an unsaturated ring. For example, in the case of the ring Q formed in the general formula (TEMP-104), A and Ring Q B are "monocyclic rings" or "fused rings". A , and ring Q C is a "fused ring". A and Tamaki Q C That is, Ring Q A and Tamaki Q C The ring Q in the general formula (TMEP-104) is fused to form a fused ring. A is a benzene ring, then ring Q A The ring Q in the general formula (TMEP-104) is a monocyclic ring. A is a naphthalene ring, then ring Q A is a fused ring.
[0105] The term "unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The term "saturated ring" means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of aromatic hydrocarbon rings include structures in which the groups given as specific examples in the specific example group G1 are terminated with a hydrogen atom. Specific examples of aromatic heterocyclic rings include structures in which the aromatic heterocyclic groups given as specific examples in the specific example group G2 are terminated with a hydrogen atom. Specific examples of aliphatic hydrocarbon rings include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom. "Forming a ring" means forming a ring only with a plurality of atoms of the main skeleton, or with a plurality of atoms of the main skeleton and one or more optional elements. For example, R 921 and R 922 and a ring Q formed by bonding together A is R 921 and the carbon atom of the anthracene skeleton to which R 922 It means a ring formed by the carbon atom of the anthracene skeleton to which R is bonded and one or more arbitrary elements. 921 and R 922 Todekan Q A In the case where R 921 and the carbon atom of the anthracene skeleton to which R 922 When a monocyclic unsaturated ring is formed by the carbon atom of the anthracene skeleton to which R is bonded and four carbon atoms, R 921 and R 922 The ring formed by
[0106] Here, unless otherwise specified herein, the "arbitrary element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur. In any element (for example, in the case of carbon or nitrogen), 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 below. When any element other than a carbon element is included, the formed ring is a heterocycle. Unless otherwise specified herein, the "one or more arbitrary elements" constituting the monocycle or fused ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5. Unless otherwise specified herein, of the "monocycle" and the "fused ring," the "monocycle" is preferred. Unless otherwise specified herein, of the "saturated ring" and the "unsaturated ring," the "unsaturated ring" is preferred. Unless otherwise specified herein, the "monocycle" is preferably a benzene ring. Unless otherwise specified herein, the "unsaturated ring" is preferably a benzene ring. When "one or more pairs of adjacent two or more rings" "combine with each other to form a substituted or unsubstituted monocyclic ring" or "combine with each other to form a substituted or unsubstituted fused ring," unless otherwise specified in this specification, preferably, one or more pairs of adjacent two or more rings combine with each other to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.
[0107] When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents Described Herein." When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents Described Herein." The above is an explanation of the case where "one or more pairs of adjacent two or more rings are bonded to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent two or more rings are bonded to form a substituted or unsubstituted fused ring" ("when bonded to form a ring").
[0108] Substituents in the case of "substituted or unsubstituted" In one embodiment of the present specification, the substituents in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituents" in the present specification) include, 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 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 carbon atoms, and an unsubstituted heterocyclic group having 5 to 50 ring atoms, 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 carbon atoms, 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. 901 When there are two or more R901 are the same or different from each other, R 902 When there are two or more R 902 are the same or different from each other, R 903 When there are two or more R 903 are the same or different from each other, R 904 When there are two or more R 904 are the same or different from each other, R 905 When there are two or more R 905 are the same or different from each other, R 906 When there are two or more R 906 are the same or different from each other, R 907 When there are two or more R 907 are the same or different from each other.
[0109] In one embodiment, the substituent in the "substituted or unsubstituted" is a group selected from the group consisting of an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, and a heterocyclic group having 5 to 50 ring atoms.
[0110] In one embodiment, the substituent in the "substituted or unsubstituted" is a group selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heterocyclic group having 5 to 18 ring atoms.
[0111] Specific examples of each group of the above optional substituents are the specific examples of the substituents described above in the section "Substituents described in this specification."
[0112] Unless otherwise specified in this specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring. Unless otherwise specified in this specification, any optional substituent may further have a substituent. The substituents further possessed by the optional substituent are the same as those of the optional substituents described above.
[0113] In this specification, a numerical range expressed using "AA to BB" means a range that includes the number AA written before "AA to BB" as the lower limit and the number BB written after "AA to BB" as the upper limit.
[0114] [First embodiment] <Organic electroluminescent element> An organic electroluminescent element according to this embodiment has an anode, a cathode, and two or more light-emitting units arranged between the anode and the cathode, the two or more light-emitting units including at least a first light-emitting unit and a second light-emitting unit, the first light-emitting unit and the second light-emitting unit being arranged in this order from the anode side toward the cathode side, the first light-emitting unit including a first light-emitting band, the second light-emitting unit including a second light-emitting band, and the first light-emitting unit including a second light-emitting band. a first electron-transporting region is disposed between the first emission region and the second emission region, the first electron-transporting region includes one or more layers, one of which is an emission-layer-side electron-transporting layer that is in direct contact with the first emission region; a cathode-side electron-transporting layer is disposed between the first electron-transporting region and the second emission region, the emission-layer-side electron-transporting layer contains a first electron-transporting region material, and the first electron-transporting region material satisfies the following mathematical formulas (Mathematical Formula 1) and (Mathematical Formula 2). 1 (E1) ≧ 1.90 eV (Equation 1) Af(E1) ≧ 1.55 eV (Equation 2) (T 1 (E1) is the triplet energy of the first electron transporting band material, and Af(E1) is the affinity of the first electron transporting band material.
[0115] The number of light-emitting units arranged between the anode and the cathode may be counted in order from the anode side as the Xth row, the (X+1)th row, the (X+2)th row, etc. (where X is an integer of 1 or more).
[0116] In conventional organic EL devices, it is known that the inclusion of an organic material (electron transporting region material) with a relatively high triplet energy in the electron transporting layer facilitates improvement of the TTF efficiency. The inventors discovered that adjusting the affinity of the electron transporting region material in addition to adjusting the triplet energy of the electron transporting region material can increase the carrier recombination probability in the emitting layer, thereby improving the TTF efficiency. In the tandem organic EL device according to the first embodiment, by incorporating a first electron transporting region material with adjusted triplet energy and affinity in the emitting-layer-side electron transporting layer, the carrier recombination probability in at least the (X+1)th-stage emitting unit can be increased and the TTF efficiency can be improved in the Xth-stage emitting unit and the (X+1)th-stage emitting unit. As a result, the light extraction efficiency and the external quantum efficiency can be improved.
[0117] In the organic EL element according to the first embodiment, the first electron-transporting region material contained in the light-emitting layer-side electron-transporting layer preferably satisfies the following formula (Formula 1A), and more preferably satisfies the following formula (Formula 1B): T 1 (E1) ≧ 2.00 eV ... (Equation 1A) T 1 (E1) ≧ 2.05 eV (Equation 1B) (T 1 (E1) is the triplet energy of the first electron-transporting band material.
[0118] In the organic EL element according to the first embodiment, the first electron-transporting region material contained in the light-emitting layer-side electron-transporting layer preferably satisfies the following formula (2A), and more preferably the following formula (21): Af(E1)≧1.60 eV (2A) Af(E1)≧1.65 eV (21) (Af(E1) is the affinity of the first electron-transporting region material.)
[0119] <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 is sometimes called a tandem organic EL element.
[0120] The organic EL element according to the first embodiment includes at least a first light-emitting unit and a second light-emitting unit as the 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 arranged closest to the anode. In one aspect of the organic EL element according to the first embodiment, the second light-emitting unit is the light-emitting unit arranged closest to the cathode.
[0121] In one aspect of the organic EL element according to the first embodiment, the 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 the 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 to the cathode side. In this case, for example, the light-emitting units may be arranged such that the first light-emitting unit is in the first row, the second light-emitting unit is in the second row, and the third light-emitting unit is in the third row. Alternatively, 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 light-emitting units may be arranged such that the third light-emitting unit is in the first row, the first light-emitting unit is in the second row, and the second light-emitting unit is in the third row. Furthermore, 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, a third light-emitting unit, and a fourth light-emitting unit as the four or more light-emitting units, the first light-emitting unit (first row), the second light-emitting unit (second row), the third light-emitting unit (third row), and the fourth light-emitting unit (fourth row) may be arranged in this order from the anode side to the cathode side, or the third light-emitting unit (first row), the first light-emitting unit (second row), the second light-emitting unit (third row), and the fourth light-emitting unit (fourth row) may be arranged in this order.
[0122] <Emission Band> In the organic EL element according to the first embodiment, the 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.
[0123] In the organic EL element according to the first embodiment, the emission bands each independently include at least one emission layer. In one aspect of the organic EL element according to the first embodiment, the emission bands each independently may include only one emission layer or may include two or more emission layers. In one aspect of the organic EL element according to the first embodiment, the emission layers each independently contain a host material. In one aspect of the organic EL element according to the first embodiment, the emission layers each independently contain a host material and a light-emitting compound. In one aspect of the organic EL element according to the first embodiment, the light-emitting compound contained in each light-emitting layer is each independently fluorescent or phosphorescent. In the organic EL element according to the first embodiment, it is preferable that at least one of the emission layers contains a fluorescent light-emitting compound.
[0124] In one aspect of the organic EL element according to the first embodiment, the first emission band includes a first emission layer. In one aspect of the organic EL element according to the first embodiment, the first emission layer contains a first host material.
[0125] In one aspect of the organic EL element according to the first embodiment, the affinity Af(H1) of the first host material contained in the first emitting layer and the affinity Af(E1) of the first electron-transporting region material contained in the emitting-layer-side electron-transporting layer satisfy the relationship of the following mathematical formula (3). The first host material and the first electron-transporting region material are the same or different from each other: |Af(H1)-Af(E1)|≦0.20 eV (3).
[0126] In one aspect of the organic EL element according to the first embodiment, the affinity Af(H1) of the first host material and the affinity Af(E1) of the first electron-transporting region material satisfy the relationship represented by the following formula (3A), (3B), (3C), (3D), (3E), (3F), or (3G). |Af(H1)-Af(E1)|≦0.20eV...(Math. 3A) |Af(H1)-Af(E1)|≦0.18eV...(Math. 3B) |Af(H1)-Af(E1)|≦0.15eV...(Math. 3C) |Af(H1)-Af(E1)|≦0.12eV...(Math 3D) |Af(H1)-Af(E1)|≦0.09eV...(Math 3E) |Af(H1)-Af(E1)|≦0.06eV...(Math 3F) |Af(H1)-Af(E1)|≦0.05eV...(Math. 3G)
[0127] The absolute value of the difference between the affinity Af(H1) of the first host material and the affinity Af(E1) of the first electron-transporting region material, |Af(H1)-Af(E1)|, is preferably 0 eV or more, and more preferably exceeds 0 eV.
[0128] 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 the first light-emitting compound.
[0129] In one aspect of the organic EL element according to the first embodiment, the second emission band includes a second emission layer. In one aspect of the organic EL element according to the first embodiment, the second emission layer contains a second host material.
[0130] 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.
[0131] 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.
[0132] In one aspect of the organic EL element according to the first embodiment, one or both of the first luminescent compound and the second luminescent compound are compounds that emit light 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 luminescent compound and the second luminescent compound are compounds that emit light 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 luminescent compound and the second luminescent compound are compounds that emit light with a maximum peak wavelength of 430 nm or more. The method for measuring the maximum peak wavelength of a compound is as follows. -6 mol / L or more 10 -5 A toluene solution containing the compound dissolved at a concentration of 100 mol / L or less is prepared and placed in a quartz cell, and the emission spectrum of this sample is measured at room temperature (300 K). The vertical axis of the emission spectrum represents emission intensity, and the horizontal axis represents wavelength. The emission spectrum can be measured, for example, using a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. The emission spectrum measurement device is not limited to the device used here.
[0133] (Method of calculating the energy level of the lowest unoccupied molecular orbital (LUMO)) For the chemical structural formula of a compound, the energy level of the lowest unoccupied molecular orbital (LUMO) is calculated using a quantum chemistry calculation program (Gaussian 09, Revision E (Gaussian Inc.); calculation method: B3LYP / 6-31G* (meaning that the functional B3LYP for DFT calculations and 6-31G* were used as the basis function)). The energy level of the lowest unoccupied molecular orbital (LUMO) is a calculated value that is highly correlated with estimating the electron affinity (Af), and can be replaced with the value of the affinity Af by changing the sign from negative to positive. The unit of the energy level of the lowest unoccupied molecular orbital (LUMO) and the affinity Af is eV.
[0134] (Host Material and Dopant Material) In one aspect of the organic EL device according to this embodiment, one or more emissive layers in the emissive zone 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 light-emitting compound, guest material, emitter, or emissive material.
[0135] In one aspect of the organic EL device according to this embodiment, one or more emitting layers in the emitting band each independently contain at least one dopant material selected from the group consisting of dopant materials shown below and at least one host material selected from the group consisting of host materials shown below.
[0136] (Dopant Material of the Light-Emitting Layer) The light-emitting layer is a layer containing a highly light-emitting substance, and various materials can be used. For example, as the highly light-emitting 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 a singlet excited state, and a phosphorescent compound is a compound that can emit light from a triplet excited state.
[0137] Examples of blue fluorescent materials that can be used in the light-emitting layer include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. Specific examples include 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.
[0138] As a green fluorescent material that can be used in the light-emitting layer, aromatic amine derivatives and the like can be used. Specifically, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-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-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), and the like.
[0139] Red fluorescent materials that can be used in the light-emitting layer include tetracene derivatives, diamine derivatives, etc. Specific examples include N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD) and 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD).
[0140] Examples of blue phosphorescent materials that can be used in the light-emitting layer include metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Specific examples include 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), and bis[2-(3',5'bistrifluoromethylphenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviation: Ir(CF 3 ppy)2 (pic)), bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) acetylacetonate (abbreviation: FIracac), and the like.
[0141] An iridium complex or the like is used as a green phosphorescent material that can be used in the light-emitting layer. 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)) and the like.
[0142] As a red phosphorescent material that can be used in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used. Specifically, bis[2-(2'-benzo[4,5-α]thienyl)pyridinato-N,C3']iridium(III) acetylacetonate (abbreviated as 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 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP), and other organometallic complexes. In addition, 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)), tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: Eu(TTA) 3 Rare earth metal complexes such as (Phen) can be used as phosphorescent compounds because they emit light from rare earth metal ions (electron transition between different multiplicities).
[0143] (Compound Represented by Formula (2)) In one aspect of the organic EL element according to the first embodiment, the dopant material (light-emitting 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 light-emitting compound and the second light-emitting 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.
[0144]
[0145] (In the formula (2), the Ax ring, the Bx ring, and the Cx ring are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, and R 201 and R 202 each independently represents R which bonds with the Ax ring, Bx ring or Cx ring to form a substituted or unsubstituted monocycle, R which bonds with the Ax ring, Bx ring or Cx ring to form a substituted or unsubstituted fused ring, or R which does not bond with the Ax ring, Bx ring or Cx ring to form the substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring 201 and R 202 each independently represents 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, -CR 25an iminyl group represented by ═N, 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, 25 is a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 60 ring 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 carbon atoms, R 25 If there are multiple R 25 are the same or different from each other.)
[0146] 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).
[0147]
[0148] (In the formula (21), R 201 and R 221 Paired with R 221 ~R 223 a set of two or more adjacent 223 and R 202 Paired with R 202 and R 224 Paired with R 224 ~R 227 a set of two or more adjacent 227 and R 228 Paired with R 228 ~R 231 and R 231 and R 201 and R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the substituted or unsubstituted monocycle or the substituted or unsubstituted fused ring. 201 and R 202 are R in the formula (2), respectively. 201 and R 202In the formula (22), Xa is O, S, Se, C(R 203 ) (R 204 ), or N(R 205 ) and R 201 and R 221 Paired with R 221 ~R 223 a set of two or more adjacent 223 and R 202 Paired with R 202 and R 224 Paired with R 224 ~R 227 and R 237 ~R 240 are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other to form the substituted or unsubstituted monocycle and the substituted or unsubstituted fused ring. 201 and R 202 are R in the formula (2), respectively. 201 and R 202 In the formula (21) or (22), R 203 , R 204 and R 205 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 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 240are 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 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 halogen atom, a cyano group, a nitro group, 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, 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 carbon atoms, 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 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 906 If there are multiple R 906 are the same or different from each other, R 907 If there are multiple R 907 are the same or different from each other.)
[0149] In one aspect of the organic EL element according to the first embodiment, R 201 and R 202 are each independently 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.
[0150] In one aspect of the organic EL element according to the first embodiment, R 201 and R 202 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0151] In one aspect of the organic EL element according to the first embodiment, R 201 and R 202 are each independently a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.
[0152] In one aspect of the organic EL element according to the first embodiment, R 201 and R 202 are each independently a group represented by the following formula (23):
[0153]
[0154] (In the formula (23), R 241 , R 242 , R 243 , R 244 , and R 245 one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other to form the substituted or unsubstituted monocycle and the substituted or unsubstituted fused ring 241 , R 242 , R 243 , R 244 , and R 245are 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 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 halogen atom, a cyano group, a nitro group, 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, 901 ~R 907 are each independently R in the formulas (21) and (22). 901 ~R 907 and plural R 241 If there are multiple R 241 are the same or different from each other, and a plurality of R 242 If there are multiple R 242 are the same or different from each other, and a plurality of R 243 If there are multiple R 243 are the same or different from each other, and a plurality of R 244 If there are multiple R 244 are the same or different from each other, and a plurality of R 245 If there are multiple R 245 are the same or different, and * indicates the bonding position.)
[0155] 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).
[0156]
[0157]
[0158] (In the formulas (211) and (221), R 221 ~R 231 and R 237 ~R 240 are R in the formulas (21) and (22), respectively. 221 ~R 231 and R 237 ~R 240 is synonymous with R 241 ~R 245 are R in the formula (23), respectively. 241 ~R 245 and Xa in the formula (221) has the same meaning as Xa in the formula (22).
[0159] 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).
[0160]
[0161] (In the formula (212), R 222 , R 226 and R 229 are R in the formula (21), respectively. 222 , R 226 and R 229 In the formula (222), Xa, R 225 and R 239 respectively represent Xa and R in the formula (22). 225 and R 239 R in the formulas (212) and (222) has the same meaning as 243 are each independently R in the formula (23). 243 is synonymous with
[0162] In one aspect of the organic EL element according to the first embodiment, in the formulae (22), (221), and (222), Xa is S (sulfur atom) or O (oxygen atom).
[0163] In this specification, the maximum peak wavelength of fluorescent light may be referred to as the maximum peak wavelength of fluorescent light.
[0164] In one aspect of the first embodiment, the second compound preferably has a maximum fluorescent emission peak wavelength of 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, the second compound preferably has a maximum fluorescent emission peak wavelength of 480 nm or less, more preferably 470 nm or less, and even more preferably 465 nm or less. In the first embodiment, when the second compound has a maximum fluorescent emission peak wavelength of 430 nm or more, electronic devices such as displays equipped with an organic EL element containing the compound according to this embodiment are likely to emit a moderate blue light. In the first embodiment, when the second compound has a maximum fluorescent emission peak wavelength of 480 nm or less, electronic devices such as displays equipped with an organic EL element containing the compound according to this embodiment are likely to emit a moderate blue light.
[0165] In this specification, the maximum fluorescence emission peak wavelength is the wavelength at which the compound to be measured is 10 -6 moles / liter or more, 10 -5 The maximum peak wavelength of the fluorescence spectrum at which the emission intensity is maximum in a fluorescence spectrum measured for a toluene solution in which the compound is dissolved at a concentration of 1 mole / liter or less. The measurement device may be a fluorescence spectrum measurement device (device name: FP-8300, manufactured by JASCO Corporation). Note that the fluorescence spectrum measurement device is not limited to the device exemplified here.
[0166] In one aspect of the organic EL element according to the first embodiment, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.
[0167] In this specification, unless otherwise specified, details of the substituents (optional substituents) in the case of "substituted or unsubstituted" included in the definition of each formula of each compound are as described in the section "Substituents in the case of 'substituted or unsubstituted'".
[0168] (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. 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 suited to the target compound.
[0169] (Specific Examples of the Second Compound According to the First Embodiment) Specific examples of the second compound according to the first embodiment include the following compounds, however, the present invention is not limited to these specific examples.
[0170] In the present specification, in specific examples of compounds, D represents a deuterium atom, Me represents a methyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.
[0171]
[0172]
[0173]
[0174] (Host Material of Light-Emitting Layer) The light-emitting layer may have a structure in which the highly light-emitting substance (dopant material) described above is dispersed in another substance (host material).
[0175] As a substance for dispersing a highly luminescent substance, various compounds can be used, and it is preferable to use a substance having a lower lowest unoccupied molecular orbital (LUMO) level than the highly luminescent substance and a lower highest occupied molecular orbital (HOMO) level.
[0176] The substance (host material) for dispersing the highly luminescent substance is preferably at least one selected from the group consisting of the following compounds (1) to (4): (1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; (2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives; (3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and chrysene derivatives; and (4) aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives. Specifically, the metal complexes include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq), and the like. 3 ), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq 2), 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), and bathocuproine (abbreviation: BCP). 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), and 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)tripylene (abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), and 6,12-dimethoxy-5,11-diphenylchrysene.Examples of the aromatic amine compound 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, and BSPB.
[0177] (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 a third compound.
[0178] In the organic EL element according to the first embodiment, the third compound is a compound represented by the following formula (3).
[0179]
[0180] (In the 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 carbon atoms, -Si(R 901 ) (R 902 ) (R 903 a group represented by —O—(R 904 a group represented by —S—(R 905a group represented by —N(R 906 ) (R 907 a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R 801 a group represented by -COOR 802 a halogen atom, a cyano group, a nitro group, 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, and L 31 and L 32 each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, 31 and Ar 32 are each independently 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.
[0181] In the third compound, R 901 ~R 907 , 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 carbon atoms, 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 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 906 If there are multiple R906 are the same or different from each other, R 907 If there are multiple R 907 are the same or different from each other, R 801 If there are multiple R 801 are the same or different from each other, R 802 If there are multiple R 802 are the same or different from each other.
[0182] 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):
[0183]
[0184] (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 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 halogen atom, a cyano group, a nitro group, 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, 3 is an oxygen atom or a sulfur atom, provided that R 311 ~R 318 one of the R is a single bond that binds to *p1, and one of the R is a non-single bond that binds to *p1 311 ~R 318one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, are not a single bond bonded to *p1, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring, 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 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 halogen atom, a cyano group, a nitro group, 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, 31 and L 32 each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, 32 is 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.
[0185] 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).
[0186]
[0187]
[0188]
[0189] (In the above formulas (31A), (31B) and (31C), R 31 ~R 38 , L 31 , L 32 , and Ar 32 are R in the formula (3), respectively. 31 ~R 38 , L 31 , L 32 , and Ar 32 and X 3 is X in the formula (31). 3 where R 311 ~R 318 and R 321 ~R 324 one of the R is a single bond that binds to *p1, and one of the R is a non-single bond that binds to *p1 311 ~R 318 and R 321 ~R 324 one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, are not a single bond bonded to *p1, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring, 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 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 halogen atom, a cyano group, a nitro group, 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.
[0190] 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 that bonds to *p1.
[0191] 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 that bonds to *p1.
[0192] In one aspect of the organic EL element of the first embodiment, the compound represented by formula (3) is a compound represented by formula (311), (312), (313), or (314) below.
[0193]
[0194]
[0195]
[0196]
[0197] (In the formulas (311), (312), (313) and (314), R 31 ~R 38 , R 311 ~R 318 , L 31 , L 32 , Ar 32 and X 3 are as defined in the above formula (3) or (31), respectively.
[0198] In one aspect of the organic EL element of the first embodiment, R which is not a single bond bonded to *p1 311 ~R 318 One or more pairs of adjacent two or more of the groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or may be bonded to each other to form a substituted or unsubstituted fused ring.
[0199] In one aspect of the organic EL element of the first embodiment, R which is not a single bond bonded to *p1 311 ~R 314 Any pair of adjacent two or more of these is not bonded to each other, and *p1 is bonded to a non-single bond R 315 ~R 318 One or more pairs of adjacent two or more of the following may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or may be bonded to each other to form a substituted or unsubstituted fused ring.
[0200] In one aspect of the organic EL element of the first embodiment, R which is not a single bond bonded to *p1 311 ~R 318 Any pair of two or more adjacent pairs of
[0201] In one aspect of the organic EL element of the first embodiment, L 31 and L 32 are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms.
[0202] 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.
[0203] In one aspect of the organic EL element of the first embodiment, Ar 31 and Ar 32 At least one of the groups is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0204] In one aspect of the organic EL element of the first embodiment, Ar 32 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0205] In one aspect of the organic EL element of the first embodiment, Ar 31 and Ar 32 At least one of the above is a group represented by the following formula (32a), (32b), (32c) or (32d).
[0206]
[0207] (In the formulas (32a), (32b), (32c) and (32d), a plurality of R 320 one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring 320 represents 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 halogen atom, a cyano group, a nitro group, 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, 320 are the same or different from each other, * is L 31 or L 32 is a single bond that bonds to
[0208] In one aspect of the organic EL element of the first embodiment, X 3 is an oxygen atom.
[0209] 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).
[0210] In one aspect of the organic EL element of the first embodiment, R 31 ~R 38 is a hydrogen atom.
[0211] In one aspect of the organic EL element of the first embodiment, the compound represented by formula (3) is a compound represented by formula (325), (326), (327), (328), or (329) below.
[0212]
[0213]
[0214]
[0215] (In the formulas (325) to (329), R 315 ~R 318 and Ar 32 are R in the formula (3), respectively. 315 ~R 318 and Ar 32 is synonymous with
[0216] In one aspect of the organic EL element of the first embodiment, R 315 ~R 318 At least one pair of adjacent two or more of the groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring.
[0217] In one aspect of the organic EL element of the first embodiment, R 315 ~R 318 At least one pair of adjacent two or more of the above groups are bonded to each other to form a substituted or unsubstituted benzene ring.
[0218] (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. 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 suited to the target compound.
[0219] (Specific Examples of the Third Compound According to the First Embodiment) Specific examples of the third compound according to the first embodiment include the following compounds, however, the present invention is not limited to these specific examples.
[0220]
[0221] In this specification, the term "host material" refers to a material that is contained in, for example, "50% by mass or more of the layer." Therefore, the light-emitting layer contains, for example, the host material in an amount of 50% by mass or more of the total mass of the light-emitting layer. When the organic EL device has multiple light-emitting layers, for example, each of the multiple light-emitting layers contains the host material in an amount of 50% by mass or more of the total mass of each light-emitting layer. Furthermore, for example, the "host material" may be contained in an amount of 60% by mass or more of the light-emitting layer, 70% by mass or more of the light-emitting layer, 80% by mass or more of the light-emitting layer, 90% by mass or more of the light-emitting layer, or 95% by mass or more of the light-emitting layer. Furthermore, for example, the "host material" may be contained in an amount of 99.5% by mass or less of the light-emitting layer, or 99% by 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 of the host material and the dopant material is 100% by mass.
[0222] In one aspect of the organic EL element according to the first embodiment, the one or more light-emitting layers do not contain a metal complex. Also, in one aspect of the organic EL element according to the first embodiment, the one or more light-emitting layers do not contain a boron-containing complex.
[0223] In one aspect of the organic EL device according to the first embodiment, the one or more light-emitting layers do not contain a phosphorescent material.
[0224] In one aspect of the organic EL device according to the first embodiment, the one or more light-emitting layers do not contain a heavy metal complex or a phosphorescent rare earth metal complex, and in one aspect of the organic EL device according to the first embodiment, the one or more light-emitting layers do not contain a heavy metal complex such as an iridium complex, an osmium complex, or a platinum complex.
[0225] <Charge Generation Zone> In one aspect of the organic EL element according to the first embodiment, a charge generation zone is preferably disposed between two or more light-emitting units. In one aspect of the organic EL element according to the first embodiment, each charge generation zone preferably independently includes at least one charge generation layer. The charge generation layer is a layer that generates holes and electrons when a voltage is applied to the organic EL element, and supplies electrons to a layer located on the anode side of the charge generation layer and holes to a layer located on the cathode side of the charge generation layer. The charge generation layer may also be called an intermediate layer, intermediate electrode, intermediate conductive layer, electron-withdrawing layer, connecting layer, or intermediate insulating layer.
[0226] When the charge generation zone is composed of multiple charge generation layers, it is preferable that the charge generation zone 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 materials that can be used for the charge generation layer of the charge generation zone include known materials that can be used for the charge generation layer of a tandem organic EL element.
[0227] In one aspect of the organic EL element according to the first embodiment, at least one of the charge generating zones includes two or more charge generating layers.
[0228] In one aspect of the organic EL element according to the first embodiment, a first charge-generation zone 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 zone includes at least a first charge-generation layer.
[0229] 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 to the cathode side, a second charge-generation zone is arranged between the second light-emitting unit and the third light-emitting unit. 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 to the cathode side, a second charge-generation zone is arranged between the third light-emitting unit and the first light-emitting unit.
[0230] In one aspect of the organic EL element according to the first embodiment, when the first charge generation region includes a first charge generation layer, the first charge generation layer is the cathode-side electron transport layer described above. In one aspect of the organic EL element according to the first embodiment, the organic material contained in the first charge generation layer may be referred to as a first charge generation region material. In one aspect of the organic EL element according to the first embodiment, the first charge generation region material is an electron transport region material (preferably a first electron transport region material) described below. In one aspect of the organic EL element according to the first embodiment, the first charge generation region material contained in the first charge generation layer and the electron transport region material contained in a layer in the electron transport region (e.g., the first electron transport layer) are different compounds or the same compound.
[0231] In one aspect of the organic EL element according to the first embodiment, the first charge generation zone further comprises a second charge generation layer, and the second charge generation layer is disposed between the first charge generation layer and the second light-emitting zone.
[0232] In one aspect of the organic EL element according to the first embodiment, the first charge-generation zone includes a first charge-generation layer and a second charge-generation layer in this order from the first light-emitting unit side. In one aspect of the organic EL element according to the first embodiment, the organic material contained in the second charge-generation layer may be referred to as a second charge-generation zone material.
[0233] 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. In one aspect of the organic EL element according to the first embodiment, the first charge generation zone material and the second charge generation zone material are different from each other.
[0234] In one aspect of the organic EL element according to the first embodiment, the second charge generation layer contains a second charge generation zone material and an acceptor material described below. 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 the second charge generation zone material and the acceptor material, the content of the second charge generation zone 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 zone material in the second charge-generation layer is 99.5% by weight or less, 99% by weight or less, or 97% by weight or less, and the total content of the acceptor material and the second charge-generation zone material in the second charge-generation layer is 100% by weight or less.
[0235] In one aspect of the organic EL element according to the first embodiment, the second charge-generation zone material is a hole-transport zone material (preferably a second hole-transport zone material) described below. In one aspect of the organic EL element according to the first embodiment, the second charge-generation zone material contained in the second charge-generation layer and the hole-transport zone material contained in a layer in the hole-transport zone (e.g., the second hole-transport layer) are either the same compound or different compounds.
[0236] <Electron-Transporting Region> In one aspect of the organic EL element according to the first embodiment, the two or more light-emitting units each independently include an electron-transporting region. In one aspect of the organic EL element according to the first embodiment, the first light-emitting unit includes a first electron-transporting region, and the second light-emitting unit includes a second electron-transporting region.
[0237] (First Electron-Transporting Region) In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region is disposed between the first light-emitting region and the second light-emitting unit.
[0238] In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region is disposed between the first light-emitting region and the first charge-generating region.
[0239] In one aspect of the organic EL device according to the first embodiment, the first electron-transporting region is disposed between the first light-emitting region and the first charge-generating layer.
[0240] In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region includes one or more layers. In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region includes a first electron-transporting layer.
[0241] In one aspect of the organic EL element according to the first embodiment, a first electron transporting region is disposed between the first light-emitting region and the first charge generating layer. In one aspect of the organic EL element according to the first embodiment, the light-emitting layer-side electron transporting layer is the first electron transporting layer. This light-emitting layer-side electron transporting layer may be a hole blocking layer.
[0242] In one aspect of the organic EL element according to the first embodiment, the cathode-side electron transport layer and the first electron transport region are in direct contact with each other. In another aspect of the organic EL element according to the first embodiment, the cathode-side electron transport layer and the first electron transport region do not necessarily have to be in direct contact with each other.
[0243] In one aspect of the organic EL element according to the first embodiment, the first light-emitting layer and the light-emitting-layer-side electron-transporting layer are in direct contact with each other. In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region includes two or more layers, one of which is the light-emitting-layer-side electron-transporting layer.
[0244] In one aspect of the organic EL element according to the first embodiment, the light-emitting layer-side electron-transporting layer contains a first electron-transporting region material.
[0245] In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region includes one layer, and the one layer is a first hole-blocking layer or a first electron-transporting layer. In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region includes one layer, and the one layer is a first hole-blocking layer, and the first hole-blocking layer and the cathode-side electron-transporting layer are in direct contact with each other. In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region includes one layer, and the one layer is a first electron-transporting layer, and the first electron-transporting layer and the cathode-side electron-transporting layer are in direct contact with each other.
[0246] In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region includes, in order from the first emission region side, a first hole-blocking layer and a first electron-transporting layer. In one aspect of the organic EL element according to the first embodiment, the first hole-blocking layer is an emission-layer-side electron-transporting layer. In one aspect of the organic EL element according to the first embodiment, the first hole-blocking layer and the first emission region are in direct contact with each other, and the first electron-transporting layer and the cathode-side electron-transporting layer are in direct contact with each other.
[0247] In one aspect of the organic EL element according to the first embodiment, the first hole blocking layer contains a first electron transporting region material. In one aspect of the organic EL element according to the first embodiment, the first electron transporting region material. The first electron transporting region material contained in the first hole blocking layer and the first electron transporting region material contained in the first electron transporting region may be the same compound or different compounds.
[0248] In one aspect of the organic EL element according to the first embodiment, the triplet energy T 1 (H1) and the triplet energy T of the first electron transporting region material 1 (E1) satisfies the relationship of the following formula (Formula 1): T 1 (E1)>T 1 (H1) ...(Math. 1)
[0249] In one aspect of the organic EL element according to the first embodiment, when the first electron-transporting region includes a first electron-transporting layer, the triplet energy T 1 (H1) and the triplet energy T of the first electron transport band material contained in the first electron transport layer 1 (E ET 1) and satisfy the relationship of the following formula (Formula 1A): T 1 (E ET 1) > T 1 (H1) ... (Math 1A)
[0250] In one aspect of the organic EL element according to the first embodiment, when the first electron-transporting region includes a first hole-blocking layer, the triplet energy T 1 (H1) and the triplet energy T of the first electron transporting region material contained in the first hole blocking layer 1 (E HB 1) and satisfy the relationship of the following formula (Formula 1B): T 1 (E HB 1) > T 1 (H1) ...(Math 1B)
[0251] In one aspect of the organic EL element according to the first embodiment, the relationships of both the above-mentioned formula (1A) and formula (1B) are satisfied.
[0252] By satisfying the relationship of the above mathematical formula (1), (1A), or (1B), triplet excitons are prevented from diffusing into the first electron transport band and the first charge generation band, and the triplet excitons of the host material in the light-emitting layer are efficiently converted into singlet excitons, which then migrate onto the dopant material (light-emitting compound) and undergo optical energy deactivation. As a result, the TTF efficiency in the first light-emitting layer is improved, and an improvement in light-emitting efficiency can be expected.
[0253] Triplet-Triple-Annihilation (sometimes referred to as TTA) has been known as a technique for improving the luminous efficiency of organic electroluminescence elements. TTA is a mechanism in which triplet excitons collide with one another to generate singlet excitons. The TTA mechanism is also sometimes referred to as the TTF mechanism. TTF is an abbreviation for Triplet-Triple Fusion.
[0254] The TTF phenomenon will be explained. Holes injected from the anode and electrons injected from the cathode recombine in the light-emitting layer to generate excitons. As has been conventionally known, the spin state of these excitons is 25% singlet excitons and 75% triplet excitons. In conventional fluorescent elements, 25% of the singlet excitons emit light when they 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 of the internal quantum efficiency of conventional fluorescent elements was said to be 25%. Meanwhile, the behavior of triplet excitons generated within organic materials 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, triplet excitons (hereinafter referred to as triplet excitons) can be calculated as follows: 3 A * When the density of triplet excitons (hereinafter referred to as triplet excitons) increases, the triplet excitons collide with each other, causing the reaction shown in the following formula: 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 *It is predicted that 1 / 5, or 20%, of the 75% of triplet excitons initially generated will convert to singlet excitons. Therefore, the singlet excitons contributing to light are 40%, calculated by adding 75% × (1 / 5) = 15% to the 25% initially generated. In this case, the TTF-derived emission ratio (TTF ratio) of the total luminescence intensity is 15 / 40, or 37.5%. Furthermore, if we assume that singlet excitons are generated by collisions between the 75% of the initially generated triplet 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 25% of the initially generated singlet excitons. In this case, the TTF ratio is 37.5 / 62.5 = 60%.
[0255] (triplet energy T 1 ) Triplet energy T 1 The following method can be used to measure the compound to be measured: -5 mol / L or more 10 -4 The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this measurement sample was measured at low temperature (77 [K]), and a tangent line was drawn to the rising edge of the phosphorescence spectrum on the short wavelength side, and the wavelength value λ at the intersection of the tangent line and the horizontal axis was determined. edge Based on [nm], the amount of energy calculated from the following conversion formula (F1) is the triplet energy T 1 Conversion formula (F1): T 1 [eV]=1239.85 / λ edge
[0256] The tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows: When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum among the spectral maxima, consider the tangent at each point on the curve toward the long wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope is at its maximum (i.e., the tangent at the inflection point) is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that maximum points with peak intensities of 15% or less of the maximum peak intensity of the spectrum are not included in the shortest wavelength maximum, and the tangent drawn at the point where the slope is closest to the shortest wavelength maximum is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Phosphorescence can be measured using an F-4500 spectrofluorophotometer manufactured by Hitachi High-Technologies Corporation. However, the measuring device is not limited to this, and measurements may be performed by combining a cooling device, a cryogenic container, an excitation light source, and a light receiving device.
[0257] In one aspect of the organic EL element according to the first embodiment, the first electron-transporting zone material and the first charge-generating zone material are different from each other. In one aspect of the organic EL element according to the first embodiment, the first electron-transporting zone material and the second charge-generating zone material are different from each other.
[0258] (Second Electron Transporting Zone) In one aspect of the organic EL element according to the first embodiment, the second electron transporting zone is disposed between the second emission zone and the cathode. In one aspect of the organic EL element according to the first embodiment, the second electron transporting zone includes one or more layers. In one aspect of the organic EL element according to the first embodiment, the second electron transporting zone includes a second electron transporting layer.
[0259] In one aspect of the organic EL element according to the first embodiment, the second electron-transporting region includes two or more layers. In one aspect of the organic EL element according to the first embodiment, the second electron-transporting region includes a second electron-transporting layer and a second electron-injecting layer. In one aspect of the organic EL element according to the first embodiment, the second electron-transporting layer is in direct contact with the second light-emitting layer in the second light-emitting region.
[0260] In one aspect of the organic EL element according to the first embodiment, the second electron-transporting region includes three or more layers. In one aspect of the organic EL element according to the first embodiment, the second electron-transporting region includes three layers, which are a second hole-blocking layer, a second electron-transporting layer, and a second electron-injecting layer. In one aspect of the organic EL element according to the first embodiment, the second electron-transporting region includes, in order from the second emission region side, a second hole-blocking layer, a second electron-transporting layer, and a second electron-injecting layer.
[0261] In one aspect of the organic EL element according to the first embodiment, the second hole blocking 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 hole blocking layer is in direct contact with the second electron transport 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 electron injection layer. In one aspect of the organic EL element according to the first embodiment, the second electron injection layer is in direct contact with the cathode.
[0262] In one aspect of the organic EL device according to the first embodiment, the second electron-transporting region contains a second electron-transporting region material.
[0263] <First Electron Transporting Region Material> In the organic EL element according to the first embodiment, the emitting layer-side electron transporting layer contains a first electron transporting region material. In one aspect of the organic EL element according to the first embodiment, the first electron transporting region material is an organic material satisfying the above-described mathematical formulas (Mathematical Formula 1) and (Mathematical Formula 2). The organic material (first electron transporting region material) satisfying the above-described mathematical formulas (Mathematical Formula 1) and (Mathematical Formula 2) is not particularly limited. For example, an organic material satisfying the above-described mathematical formulas (Mathematical Formula 1) and (Mathematical Formula 2) can be selected from known electron transporting region materials and known charge generating region materials. In one aspect of the organic EL element according to the first embodiment, the first electron transporting region material is preferably a compound represented by the following formula (E1), (E2), (E3), (E4), (E41), (E42), (E43), (E44), (E5), (E61), (E62), or (E7). The first electron transport region material may be an organic material that satisfies the above-described formulas (1) and (2) selected from the "compounds contained in the electron transport layer" described below or the "compounds contained in the hole blocking layer" described below.
[0264] (Electron Transporting Region Material) In the organic EL element according to the first embodiment, the material contained in the electron transporting region is referred to as the electron transporting region material. The electron transporting region material is, for example, the first electron transporting region material and the second electron transporting region material described above. The electron transporting region material can also be used as the first charge generating region material.
[0265] In one aspect of the organic EL element according to the first embodiment, at least one of the layers included in the first electron-transporting region contains a compound represented by the following formula (E1), (E2), (E3), (E4), (E41), (E42), (E43), (E44), (E5), (E61), (E62), or (E7) as a first electron-transporting region material.
[0266] In one aspect of the organic EL element according to the first embodiment, at least one of the layers included in the second electron-transporting region contains a compound represented by the following formula (E1), (E2), (E3), (E4), (E41), (E42), (E43), (E44), (E5), (E61), (E62), or (E7) as a second electron-transporting region material.
[0267] In one aspect of the organic EL element according to the first embodiment, the first charge generation layer contains, as a first charge generation region material, a compound represented by the following formula (E1), (E2), (E3), (E4), (E41), (E42), (E43), (E44), (E5), (E61), (E62), or (E7).
[0268] In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region material is a compound represented by the following formula (E1).
[0269]
[0270] (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 carbon atoms, -Si(R 901 ) (R 902 ) (R 903 a group represented by —O—(R 904 a group represented by —S—(R 905 a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R 801 a group represented by -COOR 802 a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by formula (E11), wherein R 101 ~R 110 is a group represented by the formula (E11), and when a plurality of groups represented by the formula (E11) are present, the plurality of groups represented by the formula (E11) are the same or different from each other, and L 101is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, 101 represents 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, and mx is 0, 1, 2, 3, 4, or 5, provided that when mx is 0, -(L 101 ) 0 - is a single bond, and L 101 When there are two or more, there are two or more L 101 are the same or different from each other, Ar 101 When two or more are present, two or more Ar 101 are the same or different, and * in the formula (E11) indicates the bonding position with the pyrene ring in the formula (E1). 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 carbon atoms, 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 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 801 If there are multiple R 801are the same or different from each other, R 802 If there are multiple R 802 are the same or different from each other.)
[0271] In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region material is a compound represented by the following formula (E2):
[0272]
[0273] (In the formula (E2), R 201 ~R 212 one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other to form the substituted or unsubstituted monocycle and the substituted or unsubstituted fused ring 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 carbon atoms, -Si(R 901 ) (R 902 ) (R 903 a group represented by —O—(R 904 a group represented by —S—(R 905 a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R 801 a group represented by -COOR 802 a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by formula (E21), provided that R does not form the substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring. 201 ~R 212is a group represented by the formula (E21), and when a plurality of groups represented by the formula (E21) are present, the plurality of groups represented by the formula (E21) are the same or different from each other, and L 201 represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, and ma is 0, 1, 2, 3, 4, or 5, provided that when ma is 0, -(L 201 ) 0 - is a single bond, and L 201 When there are two or more, there are two or more L 201 are the same or different from each other, Ar 201 is 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, 201 When two or more are present, two or more Ar 201 are the same or different, and * in formula (E21) indicates the bonding position to the benz[a]anthracene ring in formula (E2). 201 ~R 212 When one or more pairs of adjacent two or more of the groups form the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted fused ring, * in the formula (E21) indicates the bonding position of the formed ring structure to the parent skeleton.) (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 carbon atoms, 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 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 801 If there are multiple R 801 are the same or different from each other, R 802 If there are multiple R 802 are the same or different from each other.)
[0274] In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region material is a compound represented by the following formula (E3):
[0275]
[0276] (In the formula (E3), R 307 and R 312 one of which represents a single bond to *1, and R 307 and R 312 The other of R represents a single bond to *2, 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 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 907a halogen atom, a cyano group, a nitro group, 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; 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 carbon atoms, and Ar 31 is a hydrogen atom, 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, and L 31 and L 32 are each independently a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 14 ring atoms, n1 is 0, 1, 2 or 3, n2 is 0, 1, 2 or 3, and when n1 is 0, -(L 31 ) 0 - is a single bond, and when n1 is 2 or more, there are two or more L 31 are connected in series with each other, and when n1 is 2 or more, there are 2 or more L 31 are the same or different from each other, and when n2 is 0, -(L 32 ) 0 - is a single bond, and when n2 is 2 or more, there are two or more L 32 are connected in series with each other, and when n2 is 2 or more, there are two or more L 32 are the same or different.) (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 carbon atoms, 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, R901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 906 If there are multiple R 906 are the same or different from each other, R 907 If there are multiple R 907 are the same or different from each other.)
[0277] In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region material is a compound represented by the following formula (E4).
[0278]
[0279] (In the formula (E4), X 2 is N or C-(L 42 ) m 2 -(Ar 42 ) m 21 and X 4 is N or C-(L 44 ) m 4 -(Ar 44 ) m 41 and X 5 is N or C-(L 45 ) m 5 -(Ar 45 ) m 51 and X 6 is N or C-(L 46 ) m 6 -(Ar 46 ) m 61 and X 2 , X 4 , X 5 and X 6At least one of L is a nitrogen atom; 41 ~L 46 each independently represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, 1 is 0, 1, 2 or 3, m 1 If is 0, then −(L 41 ) 0 - is a single bond, m 2 is 0, 1, 2 or 3, m 2 If is 0, then −(L 42 ) 0 - is a single bond, m 3 is 0, 1, 2 or 3, and m 3 If is 0, then −(L 43 ) 0 - is a single bond, m 4 is 0, 1, 2 or 3, m 4 If is 0, then −(L 44 ) 0 - is a single bond, m 5 is 0, 1, 2 or 3, m 5 If is 0, then −(L 45 ) 0 - is a single bond, m 6 is 0, 1, 2 or 3, m 6 If is 0, then −(L 46 ) 0 - is a single bond, m 1 When is 2 or more, L is 2 or more 41 are the same or different from each other, and m 2 When is 2 or more, L is 2 or more 42 are the same or different from each other, and m 3 When is 2 or more, L is 2 or more 43 are the same or different from each other, and m 4 When is 2 or more, L is 2 or more 44 are the same or different from each other, and m 5 When is 2 or more, L is 2 or more 45 are the same or different from each other, and m 6When is 2 or more, L is 2 or more 46 are the same or different from each other, and 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, 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 carbon atoms, -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 substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R 920 a group represented by -COOR 921 a halogen atom, a cyano group, a nitro group, 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, provided that Ar 41 ~Ar 46 at least one of is a substituted or unsubstituted aryl group having 13 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 13 to 50 ring atoms, 11 When is 2 or more, there are 2 or more Ar 41 are the same or different from each other, and m 21When is 2 or more, there are 2 or more Ar 42 are the same or different from each other, and m 31 When is 2 or more, there are 2 or more Ar 43 are the same or different from each other, and m 41 When is 2 or more, there are 2 or more Ar 44 are the same or different from each other, and m 51 When is 2 or more, there are 2 or more Ar 45 are the same or different from each other, and m 61 When is 2 or more, there are 2 or more Ar 46 are the same or different.) (In the 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 carbon atoms, 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 911 If there are multiple R 911 are the same or different from each other, R 912 If there are multiple R 912 are the same or different from each other, R 913 If there are multiple R 913 are the same or different from each other, R 914 If there are multiple R 914 are the same or different from each other, R 915 If there are multiple R 915 are the same or different from each other, R 916 If there are multiple R 916 are the same or different from each other, R 917If there are multiple R 917 are the same or different from each other, R 918 If there are multiple R 918 are the same or different from each other, R 919 If there are multiple R 919 are the same or different from each other, R 920 If there are multiple R 920 are the same or different from each other, R 921 If there are multiple R 921 are the same or different from each other.)
[0280] In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region material is a compound represented by the following formula (E41):
[0281]
[0282] (In the formula (E41), L 41 , L 43 , and L 45 respectively represent L in the formula (E4). 41 , L 43 , and L 45 is synonymous with m 1 , m 3 , and m 5 are m in the formula (E4), respectively. 1 , m 3 , and m 5 is synonymous with R A and R B One of R represents a single bond with *3, and R 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, in the case of "substituted", it has one or more substituents T, 401 ~R 409are each independently a hydrogen atom or a substituent R, and 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 carbon atoms, -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 carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, when two or more substituents R are present, the two or more substituents R are the same or different, and R 410 is a hydrogen atom, and R 401 ~R 409 , and R that is not a single bond with *3 A and R B adjacent pairs of two or more of X are not bonded to each other, 6 is a nitrogen atom or C—Ar 46 and Ar 46 is a hydrogen atom or a substituent V, Ar 41 and Ar 45 At least one of the groups is a substituent X, and Ar 41 and Ar 45 In the case of "substituted or unsubstituted" with respect to the substituent X as the substituent X, in the case of "substituted", it means that Ar has one or more substituents U and is not a substituent X. 41 and Ar 45is 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 and containing no 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 group selected from the group consisting of 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 heterocyclic group represented by the following formula (E412), wherein when two or more substituents X are present, the two or more substituents X are the same as or different from one another, when two or more substituents U are present, the two or more substituents U are the same as or different from one another, R A or R B Substituents S, R as A or R B In the case of "substituted or unsubstituted", the substituents T and Ar 41 and Ar 45 The substituent U in the case of "substituted or unsubstituted" and Ar 46The substituents V as the formula (I) 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 carbon atoms, -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 carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and when two or more substituents T are present, the two or more substituents T are the same or different.
[0283]
[0284] (In the formula (E411), X 41 is N(R 429 ), an oxygen atom, or a sulfur atom. 421 ~R 429 One of them is L 41 or L 45 represents a single bond with R 421 ~R 429 At least one pair of adjacent pairs of L are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other; 41 or L 45 and R does not represent a single bond with 421 ~R 429are 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 carbon atoms, -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 carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms and containing no nitrogen atom.) (In the formula (E412), X 42 is N(R 437 ), an oxygen atom, or a sulfur atom. 431 ~R 437 One of them is L 41 or L 45 represents a single bond with R 431 ~R 437 At least one pair of adjacent pairs of L are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other; 41 or L 45 and R does not represent a single bond with 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 carbon atoms, -Si(R 911 ) (R912 ) (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 carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms and not containing a nitrogen atom.) (In the formulae (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 carbon atoms, 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 and not containing a nitrogen atom, R 911 If there are multiple R 911 are the same or different from each other, R 912 If there are multiple R 912 are the same or different from each other, R 913 If there are multiple R 913 are the same or different from each other, R 914 If there are multiple R 914 are the same or different from each other, R 915 If there are multiple R 915 are the same or different from each other, R 916 If there are multiple R 916 are the same or different from each other, R 917 If there are multiple R 917 are the same or different from each other, R 918 If there are multiple R 918 are the same or different from each other, R 919If there are multiple R 919 are the same or different from each other.)
[0285] In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region material is a compound represented by the following formula (42).
[0286]
[0287] (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 (E4). 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 are m in the formula (E4), respectively. 1 , m 3 , m 31 and m 5 is synonymous with R 4001 ~R 4008 one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, 4009 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 4001 ~R 4008are 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 carbon atoms, -Si(R 911 ) (R 912 ) (R 913 a group represented by —O—(R 914 a group represented by —S—(R 915 a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R 920 a group represented by -COOR 921 a halogen atom, a cyano group, a nitro group, 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, with the proviso that R 4009 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 4001 ~R 4008 At least one of R is a single bond to *4, and *4 indicates the bonding position to the carbazole ring in formula (E42). 4001 ~R 4008 When one or more pairs of adjacent two or more of the groups form the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted fused ring, *4 in the formula (E42) indicates the bonding position of the formed ring structure to the parent skeleton.) (In the formula (E42), R 911 , R 912 , R 913 , R 914 , R 915 , R 920 and R 921 are R in the formula (E4), respectively. 911 , R 912 , R 913 , R 914 , R 915 , R 920 and R 921 is synonymous with
[0288] In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region material is a compound represented by the following formula (E43):
[0289]
[0290] (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 (E4). 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 are m in the formula (E4), respectively. 1 , m 3 , m 31 and m 5 is synonymous with R 5001 ~R 5008 one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other to form the substituted or unsubstituted monocycle and the substituted or unsubstituted fused 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 carbon atoms, -Si(R 911 ) (R 912 ) (R 913a group represented by —O—(R 914 a group represented by —S—(R 915 a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R 920 a group represented by -COOR 921 a halogen atom, a cyano group, a nitro group, 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, provided that R does not form the substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring. 5001 ~R 5008 At least one of R is a single bond to *5, and *5 indicates the bonding position to the dibenzofuran ring in formula (E43). 5001 ~R 5008 When one or more pairs of adjacent two or more of the groups form the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted fused ring, *5 in the formula (E43) indicates the bonding position of the formed ring structure to the parent skeleton.) (In the formula (E43), R 911 , R 912 , R 913 , R 914 , R 915 , R 920 and R 921 are R in the formula (E4), respectively. 911 , R 912 , R 913 , R 914 , R 915 , R 920 and R 921 is synonymous with
[0291] In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region material is a compound represented by the following formula (E44):
[0292]
[0293] (In the formula (E44), X 2 , X 4 , X 6 , L 41 , L 43 , L45 , Ar 41 and Ar 45 respectively represent X in the formula (E4). 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 are m in the formula (E4), respectively. 1 , m 3 , m 31 and m 5 is synonymous with R 6009 and R 6010 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and R 6001 ~R 6008 one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other to form the substituted or unsubstituted monocycle and the substituted or unsubstituted fused ring 6001 ~R 6010 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 carbon atoms, -Si(R 911 ) (R 912 ) (R 913 a group represented by —O—(R 914 a group represented by —S—(R 915 a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R 920 a group represented by -COOR921 a halogen atom, a cyano group, a nitro group, 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, provided that R does not form the substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring. 6001 ~R 6010 At least one of R is a single bond to *6, and *6 indicates the bonding position to the fluorene ring in formula (E44). 6001 ~R 6010 When one or more pairs of adjacent two or more of the groups form the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted fused ring, *6 in the formula (E44) indicates the bonding position of the formed ring structure to the parent skeleton.) (In the formula (E44), R 911 , R 912 , R 913 , R 914 , R 915 , R 920 and R 921 are R in the formula (E4), respectively. 911 , R 912 , R 913 , R 914 , R 915 , R 920 and R 921 is synonymous with
[0294] In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region material is a compound represented by the following formula (E5).
[0295]
[0296] (In the formula (E5), R 501 ~R 508 one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring 501 ~R 508are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring 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 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -O-(R 904 a group represented by —S—(R 905 a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms; a halogen atom, a cyano group, a nitro group, a carboxy group; a group represented by —N(R 905N ) (R 906N or a group represented by the formula (E51), wherein when a plurality of groups represented by the formula (E51) are present, the plurality of groups represented by the formula (E51) are the same or different from one another, and L 501 represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, 501 represents 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, mb is 1, 2, 3 or 4, and when mb is 2, 3 or 4, two or more L 501 are the same or different from each other, and two or more HAr 501 are the same or different, and * in the formula (E51) indicates the bonding position to the phenanthroline ring in the formula (E5). 501 ~R 508 When one or more pairs of adjacent two or more of the groups form the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted fused ring, * in the formula (E51) indicates the bonding position of the formed ring structure to the parent skeleton.) (In the formula (E5), R 904 and R 905are 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 carbon atoms, 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 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 905N and R 906N are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 905N If there are multiple R 905N are the same or different from each other, R 906N If there are multiple R 906N are the same or different from each other.)
[0297] In one aspect of the organic EL element according to the first embodiment, R in the first electron transporting region material 501 ~R 508 At least one of the above 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 formulae (E511) to (E515).
[0298]
[0299] (In the formula (E511), R 511 , R 512 , R 513 , R 514 and R 515 One of them is L 501 In the formula (E512), R 516 , R 517 , R 518 and R 519 One of them is L 501 In the formula (E513), R 520 , R 521 and R 522 One of them is L501 In the formula (E514), R 523 , R 524 , R 525 and R 526 One of them is L 501 In the formula (E515), R 527 , R 528 , R 529 and R 530 One of them is L 501 represents a single bond with R 511 ~R 530 At least one pair of adjacent pairs of L are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other; 501 and R does not represent a single bond with 511 ~R 530 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring 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 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -O-(R 904 a group represented by —S—(R 905 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 a group represented by —N(R 905N ) (R 906N ) is a group represented by R 904 , R 905 , R 905N and R 906N are R in the formula (E5), respectively. 904 , R 905 , R 905N and R 906N and * indicates the bonding position.)
[0300] In one aspect of the organic EL element according to the first embodiment, R in the first electron transporting region material 501 ~R 508 At least one of the above 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 formulae (E516) to (E526).
[0301]
[0302]
[0303] (In the formulae (E516) to (E526), R E One of them is L 501 represents a single bond with E one or more pairs of adjacent two or more of L are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, 501 and R does not represent a single bond with E each independently represents, in the formulas (E511) to (E515), L 501 and R does not represent a single bond with 511 ~R 530 and plural R E are the same or different, and * represents the bonding position.)
[0304] In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region material is a compound represented by the following formula (E61) or (E62).
[0305]
[0306] (In the formulae (E61) and (E62), each Cz is independently a carbazolyl group or an indolyl group represented by any one of the formulae (E63), (E64), (E65), (E66), (E67) and (E68) below, 6each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring 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, and L 6 If there are multiple L 6 are the same as or different from each other, when a plurality of Cz's are present, the plurality of Cz's are the same as or different from each other, and each FA is independently a substituted or unsubstituted fused ring group having 6 to 50 ring carbon atoms, with the proviso that FA is not an unsubstituted carbazolyl group.
[0307] In one aspect of the organic EL element according to the first embodiment, each FA may independently be a substituted or unsubstituted heterocycle having 6 to 50 ring carbon atoms. In one aspect of the organic EL element according to the first embodiment, each FA is independently a substituted or unsubstituted heterocycle having 6 ring carbon atoms. In one aspect of the organic EL element according to the first embodiment, each FA is independently a substituted or unsubstituted azine ring.
[0308]
[0309] (In the formulae (E63), (E64), (E65), (E66), (E67) and (E68), Z 6 are each independently 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 605are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, each ring E is independently a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 ring carbon atoms, a substituted or unsubstituted nitrogen atom-containing non-aromatic heterocyclic ring having 3 to 20 ring atoms, a substituted or unsubstituted aromatic hydrocarbon ring having 4 to 50 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 4 to 50 ring atoms, a is 3, each b is independently 0, 1, 2, 3, or 4, c is 4, d is 2, e is 1, and when a plurality of R 6 one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring 6 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, -O-(R 904 a group represented by —S—(R 905 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, 601 If there are multiple R 601 are the same or different from each other, R 602 If there are multiple R 602 are the same or different from each other, R 603 If there are multiple R 603 are the same or different from each other, R 604 If there are multiple R 604 are the same or different from each other, R 605If there are multiple R 605 are the same or different from each other, and a plurality of R 6 are the same or different. * 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 carbon atoms, 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 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other.)
[0310] In one aspect of the organic EL element according to the first embodiment, the group represented by formula (E63) is a group represented by any one of formulae (E631), (E632), (E633), and (E634) below:
[0311]
[0312]
[0313] (R in the formulas (E631), (E632), (E633) and (E634) 6 and a are R in the formula (E63), respectively. 6 and a, bx is 4, by is 3, and R 61 ~R 68 each independently represents R in formula (E63). 6 and plural R 6 are the same or different, and * represents the bonding position.)
[0314] In one aspect of the organic EL element according to the first embodiment, the group represented by formula (E65) is a group represented by any one of formulae (E651), (E652), (E653), and (E654) below:
[0315]
[0316]
[0317] (In the formulae (E651), (E652), (E653) and (E654), R 6 and c are R in the formula (E65), respectively. 6 and c, bx is 4, by is 3, and R 61 ~R 68 each independently represents R in formula (E65). 6 and plural R 6 are the same or different, and * represents the bonding position.)
[0318] In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region material is a compound represented by the following formula (E7):
[0319]
[0320] (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 carbon atoms, -Si(R 901 ) (R 902 ) (R 903 a group represented by —O—(R 904 a group represented by —S—(R 905 a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R 801 a group represented by -COOR 802a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (E71), wherein R 701 ~R 710 is a group represented by the formula (E71), and when a plurality of groups represented by the formula (E71) are present, the plurality of groups represented by the formula (E71) are the same or different from each other, and L 701 represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, 701 represents 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, and mx7 is 0, 1, 2, 3, 4, or 5, provided that when mx7 is 0, -(L 701 ) 0 - is a single bond, and L 701 When there are two or more, there are two or more L 701 are the same or different from each other, Ar 701 When two or more are present, two or more Ar 701 are the same or different, and * in the formula (E71) indicates the bonding position with the ring represented by the formula (E7). 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 carbon atoms, 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 901 If there are multiple R 901 are the same or different from each other, R 902If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 801 If there are multiple R 801 are the same or different from each other, R 802 If there are multiple R 802 are the same or different from each other.)
[0321] In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region material is a compound having a fused polycyclic skeleton. In one aspect of the organic EL element according to the first embodiment, the first electron-transporting region material is not a compound having an anthracene skeleton. In one aspect of the organic EL element according to the first embodiment, when the first electron-transporting region material is a compound having a fused polycyclic skeleton, the fused polycyclic skeleton is a fused aromatic hydrocarbon ring having 10 to 30 ring carbon atoms or a fused aromatic heterocycle having 14 to 30 ring atoms. In one aspect of the organic EL element according to the first embodiment, when the first electron-transporting region material is a compound having a fused polycyclic skeleton, at least one of the fused polycyclic skeletons is at least one ring selected from the group consisting of a pyrene ring, a fluoranthene ring, a benzofluoranthene ring, a phenanthrene ring, a benzophenanthrene ring, a chrysene ring, a benzochrysene ring, a triphenylene ring, a benzotriphenylene ring, a benzoxanthene ring, and a benzanthracene ring.
[0322] In one aspect of the organic EL element according to the first embodiment, when the first charge-generation region material is a compound represented by formula (E5) (a compound having a phenanthroline skeleton), the first charge-generation region material contains only one phenanthroline skeleton.
[0323] In one aspect of the organic EL device according to the first embodiment, the first electron-transporting region material is a compound represented by formula (E1), (E2), (E3), (E4), or (E42).
[0324] (Method for Producing Electron-Transporting Zone Material) The electron-transporting zone material can be produced by a known method. Alternatively, the electron-transporting zone material can be produced by following a known method and using known alternative reactions and raw materials suited to the target product.
[0325] (Specific Examples of Electron Transporting Zone Materials) Specific examples of electron transporting zone materials include 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 protium atom is represented as H or is omitted. In this specification, a methyl group may be represented as Me, a phenyl group as Ph, and a tert-butyl group as tBu.
[0326]
[0327]
[0328]
[0329]
[0330]
[0331]
[0332]
[0333]
[0334]
[0335]
[0336]
[0337]
[0338]
[0339]
[0340] (Metal and Metal Compound) In one aspect of the organic EL element according to the first embodiment, the first charge generation layer contains a first charge generation region material and at least one selected from the group consisting of metals and metal compounds. In one aspect of the organic EL element according to the first embodiment, the metal contained in the first charge generation layer is at least one metal selected from the group consisting of rare earth metals, alkali metals, and alkaline earth metals.
[0341] In one aspect of the organic EL element according to the first embodiment, the metal contained in the first charge generation layer is at least one metal selected from the group consisting of ytterbium, erbium, lithium, cesium, magnesium, and calcium.
[0342] In one aspect of the organic EL element according to the first embodiment, the metal compound contained in the first charge generation layer is at least one metal compound selected from the group consisting of alkali metal compounds and alkaline earth metal compounds.
[0343] In one aspect of the organic EL element according to the first embodiment, the metal compound contained in the first charge generation layer is 8-(quinolinolato)lithium (abbreviation: Liq), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), 2-(2-pyridyl)phenolatolithium (abbreviation: LiPP), 2-(2-pyridyl)-3-pyridinolatolithium (abbreviation: LiPPy), 4-phenyl-2-(2-pyridyl)phenolatolithium (abbreviation: LiPPP), lithium oxide (LiOx), and cesium carbonate.
[0344] (Specific Examples of Other Electron-Transporting Region Materials) In addition to the above-described electron-transporting region materials, specific examples of other electron-transporting region materials include the following compounds. However, the present invention is not limited to these specific examples of electron-transporting region materials.
[0345]
[0346]
[0347]
[0348] <Hole Transport Region> In one aspect of the organic EL element according to the first embodiment, the two or more light-emitting units each independently include a hole transport region. In one aspect of the organic EL element according to the first embodiment, the first light-emitting unit includes a first hole transport region, and the second light-emitting unit includes a second hole transport region.
[0349] (First Hole Transport Zone) In one aspect of the organic EL device according to the first embodiment, the first hole transport zone is disposed between the anode and the first light-emitting zone. In one aspect of the organic EL device according to the first embodiment, the first hole transport zone includes one or more layers.
[0350] In one aspect of the organic EL element according to 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.
[0351] In one aspect of the organic EL element according to the first embodiment, the first hole-transporting region includes three or more layers. In one aspect of the organic EL element according to the first embodiment, the first hole-transporting region includes three layers: a first hole-injection layer, a first hole-transporting layer, and a first electron-blocking layer. In one aspect of the organic EL element according to the first embodiment, the first hole-transporting region includes, in order from the light-emitting region side, a first hole-injection layer, a first hole-transporting layer, and a first electron-blocking layer.
[0352] In one aspect of the organic EL element according to the first embodiment, the first electron blocking layer is in direct contact with the first light-emitting layer in the first light-emitting band. In one aspect of the organic EL element according to the first embodiment, the first electron blocking layer is in direct contact with the 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 hole injection layer. In one aspect of the organic EL element according to the first embodiment, the first hole injection layer is in direct contact with the anode.
[0353] In one aspect of the organic EL device according to the first embodiment, the first hole transporting region contains a first hole transporting region material.
[0354] (Second Hole-Transporting Region) In one aspect of the organic EL element according to the first embodiment, the second hole-transporting region is disposed between the first light-emitting unit and the second light-emitting region.
[0355] In one aspect of the organic EL element according to the first embodiment, the second hole transporting zone is disposed between the first charge generating zone and the second light emitting zone.
[0356] In one aspect of the organic EL device according to the first embodiment, the second hole transporting zone is disposed between the first charge generating layer and the second light emitting zone.
[0357] In one aspect of the organic EL device according to the first embodiment, the second hole transporting zone is disposed between the second charge generating layer and the second light emitting zone.
[0358] In one aspect of the organic EL device according to this embodiment, the second hole transporting region includes one or more layers.
[0359] In one aspect of the organic EL device according to the first embodiment, the second hole-transporting region includes a second hole-transporting layer, and in one aspect of the organic EL device according to the first embodiment, the second hole-transporting layer is in direct contact with the second light-emitting layer in the second light-emitting region.
[0360] In one aspect of the organic EL element according to the first embodiment, the second hole-transporting region includes two or more layers. In one aspect of the organic EL element according to the first embodiment, the second hole-transporting region includes a second hole-transporting layer and a second electron-blocking layer. In one aspect of the organic EL element according to the first embodiment, the second hole-transporting region includes, in order from the first-emitting unit side, a second hole-transporting layer and a second electron-blocking layer. In one aspect of the organic EL element according to the first embodiment, the second hole-transporting layer and the second electron-blocking layer are in direct contact with each other. In one aspect of the organic EL element according to the first embodiment, the second electron-blocking layer is in direct contact with the second-emitting layer in the second-emitting region.
[0361] In one aspect of the organic EL device according to the first embodiment, a second hole transport layer is disposed between the second charge generation layer and the second light-emitting zone.
[0362] 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 do not necessarily have to be in direct contact with each other.
[0363] In one aspect of the organic EL device according to the first embodiment, the second hole transport layer contains a second hole transport zone material.
[0364] In one aspect of the organic EL element according to the first embodiment, the second hole transporting zone material and the second charge generating zone 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 transporting zone material and the first charge generating zone material are different from each other. In one aspect of the organic EL element according to the first embodiment, the second hole transporting zone material and the first electron transporting zone material are different from each other.
[0365] (Hole Transporting Region Material) In the organic EL element according to the first embodiment, the material contained in the hole transporting region is referred to as the hole transporting region material. The hole transporting region material is, for example, the first hole transporting region material and the second hole transporting region material described above. The hole transporting region material can also be used as the second charge generating region material.
[0366] In one aspect of the organic EL element according to the first embodiment, at least one of the layers included in the first hole-transporting region contains a compound represented by the following formula (B1) or formula (B2) as a first hole-transporting region material:
[0367] In one aspect of the organic EL element according to the first embodiment, at least one of the layers included in the second hole-transporting region contains a compound represented by the following formula (B1) or formula (B2) as a second hole-transporting region material:
[0368] 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 a compound represented by the following formula (B1) or formula (B2) as a second charge generation zone material:
[0369]
[0370] (In the 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 carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, 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 carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, 1 , B 1 and C 1 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or —Si(R 121 ) (R 122 ) (R 123 ) is a group represented by R 121 , R 122 and R 123 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 121 If there are multiple R121 are the same or different from each other, R 122 If there are multiple R 122 are the same or different from each other, R 123 If there are multiple R 123 are the same or different from each other.)
[0371]
[0372] (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 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, n2 is 1, 2, 3, or 4, and when n2 is 1, L C5 represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, and when n2 is 2, 3, or 4, a plurality of L C5 are the same or different from each other, and when n2 is 2, 3 or 4, a plurality of L C5 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted fused ring. C5 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, 131 , Ar 132 , Ar 133 and Ar 134 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or —Si(R 121 ) (R 122 ) (R 123 ) is a group represented by R 121 , R122 and R 123 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 121 If there are multiple R 121 are the same or different from each other, R 122 If there are multiple R 122 are the same or different from each other, R 123 If there are multiple R 123 are the same or different from each other.)
[0373] In one aspect of the organic EL element according to this embodiment, in the compound represented by formula (B2), the first amino group represented by formula (B2-1) below and the second amino group represented by formula (B2-2) below are the same group:
[0374]
[0375] (In the formulas (B2-1) and (B2-2), * represents L C5 )
[0376] In one aspect of the organic EL element according to this embodiment, the first amino group represented by formula (B2-1) and the second amino group represented by formula (B2-2) may be different from each other.
[0377] In one aspect of the organic EL element according to the first embodiment, A in the formula (B1) and the following formula (B100) 1 , B 1 and C 1 are each independently a group represented by any one of the formulae selected from the group consisting of the following formulae (1A), (1B), (1C), (1D), (1E), (1F), and (1G):
[0378]
[0379] (In the formula (1A), *11 represents L 11 , L 12 or L 13 is the bonding position to R 101 ~R 105 is a single bond bonded to *12, and R106 ~R 110 is a single bond bonded to *13, and 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 carbon atoms, and R 101 ~R 105 and wherein none of the pairs of adjacent two or more of R 106 ~R 110 Among the groups of two or more adjacent groups, none of the groups are bonded to each other, and R 111 ~R 115 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 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms, 111 ~R 115 When m=0 and n=0, *13 is 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, R 101 ~R 105 One selected from is a single bond bonded to *13.
[0380]
[0381] (In the formula (1B), *14 represents L 11 , L 12 or L 13 is the bonding position to R 121 ~R 128 one selected from is a single bond bonded to *15, and R 121 ~R 128are 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 carbon atoms, and R 121 ~R 128 Any pair of adjacent pairs of two or more of the groups are not bonded to each other.)
[0382]
[0383] (In the formula (1C), *16 represents L 11 , L 12 or L 13 is the bonding position to R 131 ~R 140 is a single bond bonded to *17, and R 131 ~R 140 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 carbon atoms, and R 131 ~R 140 Any pair of adjacent pairs of two or more of the groups are not bonded to each other.)
[0384]
[0385] (In the formula (1D), *18 represents L 11 , L 12 or L 13 is the bonding position to X 11 is an oxygen atom, a sulfur atom, C(Ra)(Rb) or N(Rc), a pair consisting of Ra and Rb bond to each other to form a substituted or unsubstituted monocycle, bond to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, n is 0 or 1, and when n is 0, R 141 ~R 148 , Rc, and one selected from Ra and Rb that do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring is a single bond bonding to *19, when n is 1, R 141 and R 142 is a single bond bonded to *a, and R141 and R 142 The other of is a single bond bonded to *b, or R 142 and R 143 is a single bond bonded to *a, and R 142 and R 143 The other of is a single bond bonded to *b, or R 143 and R 144 is a single bond bonded to *a, and R 143 and R 144 the other is a single bond bonded to *b, (i) R 145 ~R 148 , R 14A , R 14B , R 14C , R 14D and Rc, and (ii) R that is not a single bond bonded to *a and *b 141 ~R 144 and (iii) Ra and Rb which are not single bonds bonded to *a and *b, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring, and one selected from the group consisting of is a single bond bonded to *19, and R which is not a single bond bonded to *19 141 ~R 148 , R 14A , R 14B , R 14C , R 14D and Rc, and Ra and Rb that are not single bonds bonded to *19, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused 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 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms.
[0386]
[0387] (In the formula (1E), *11a represents L 11 , L 12 or L 13 is the bonding position to R 151 ~R 155 is a single bond bonded to *11b, and R 151 ~R155 the other selected from is a single bond bonded to *11c, and R 151 ~R 155 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group, and R 151 ~R 155 Among the groups of two or more adjacent groups, none of the groups are bonded to each other, and 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.
[0388]
[0389] (In the formula (1F), *11d represents L 11 , L 12 or L 13 is the bonding position to R 181 ~R 192 one selected from is a single bond bonded to *11e, and R 181 ~R 192 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 carbon atoms, and R 181 ~R 192 Any pair of adjacent pairs of two or more of
[0390]
[0391] (In the formula (1G), X B represents a single bond, an oxygen atom, a sulfur atom, or N(R B11 ) or C(R B12 ) (R B13 ) and X B If there are multiple Xs, B are the same or different from each other, and X B is C(R B12 ) (R B13 ), then R B12 and R B13and R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, 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 the R is a single bond bonded to *1, and one of the R is not a single bond bonded 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 carbon atoms, -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 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, B9 and R B10 are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, are not a single bond bonded to *1, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring, B9 , R B10 , R B12 and R B13are 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 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and *2 is L 11 , L 12 or L 13 (In the group represented by formula (1G), 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 carbon atoms, 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 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other.)
[0392] In one aspect of the organic EL element according to the first embodiment, the hole transporting region 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 transporting region material is a compound represented by the following formula (B100):
[0393]
[0394] (In the formula (B100), L 11 , L 12 and L 13are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, 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 carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, 1 , B 1 , and C 1 each independently represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, —Si(R C1 ) (R C2 ) (R C3 or a group represented by the formula (1G), 1 , B 1 , and C 1 At least one selected from the group consisting of is a group represented by formula (1G), 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 carbon atoms, 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 C1 If there are multiple R C1 are the same or different from each other, R C2 If there are multiple R C2 are the same or different from each other, R C3 If there are multiple R C3 are the same or different from each other, and in the formula (1G), X B represents a single bond, an oxygen atom, a sulfur atom, or N(R B11 ) or C(R B12 ) (R B13 ) and X B If there are multiple Xs, B are the same or different from each other, and XB is C(R B12 ) (R B13 ), then R B12 and R B13 and R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, 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 the R is a single bond bonded to *1, and one of the R is not a single bond bonded 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 carbon atoms, -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 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, B9 and R B10 are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, are not a single bond bonded to *1, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring, B9 , RB10 , 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 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and *2 is L 11 , L 12 or L 13 and when two or more groups represented by formula (1G) are present, the two or more groups represented by formula (1G) are the same or different.) (In the compound represented by 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 carbon atoms, 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 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other.)
[0395] In one aspect of the organic EL element according to the first embodiment, the group represented by formula (1G) is a group represented by any one of formulae (11G), (12G), and (13G) below:
[0396]
[0397]
[0398] (In the formula (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 respectively represent X in the formula (1G). B , R B1 , R B2 , R B3 , R B4 , R B5 , R B6 , R B7 , R B8 , *1 and *2 are the same meanings, 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 carbon atoms, -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 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, Z is an oxygen atom, a sulfur atom, or a C(R Z1 ) (R Z2 ) and 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 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.) (In the formula (11G), (12G), or (13G), R 901 , R 902 , R 903 and R 904are R in the formula (1G), respectively. 901 , R 902 , R 903 and R 904 is synonymous with
[0399] 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.
[0400] In one aspect of the organic EL element according to the first embodiment, the group represented by formula (1G) is a group represented by any one of formulae selected from the group consisting of formulae (11G-1), (12G-1), (12G-2), and (13G-1):
[0401]
[0402]
[0403] (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 respectively represent R in the formula (1G). B1 , R B2 , R B3 , R B4 , R B5 , R B6 , R B7 , R B8 , *1 and *2 are the same meanings, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20are 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 carbon atoms, -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 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0404] R in the formulae (11G), (12G), (13G), (11G-1), (12G-1), (12G-2) and (13G-1) 11 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 20 is a hydrogen atom. R in the formulae (11G), (12G), (13G), (11G-1), (12G-1), (12G-2) and (13G-1) 12 and R 19 are each independently a substituent other than a hydrogen atom. 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 carbon atoms.
[0405] In one aspect of the organic EL element according to this embodiment, when n is 1 in the formula (1D), R 141 and R 142is a single bond bonded to *a, and R 141 and R 142 When the other is a single bond bonded to *b, the formula (1D) is represented by the following formula (13D): 142 and R 143 is a single bond bonded to *a, and R 142 and R 143 When the other is a single bond bonded to *b, the formula (1D) is represented by the following formula (12D): 143 and R 144 is a single bond bonded to *a, and R 143 and R 144 When the other is a single bond bonded to *b, the formula (1D) is represented by the following formula (11D).
[0406] In one aspect of the organic EL element according to the first embodiment, A in formula (B1) or formula (B100) 1 , B 1 and C 1 At least one selected from the group consisting of: is a group represented by any one of the formulae selected from the group consisting of the following formulae (11D), (12D) and (13D):
[0407]
[0408]
[0409]
[0410] (In the formulas (11D), (12D) and (13D), *18 represents L 11 , L 12 or L 13 is the bonding position to X 11 represents X in the formula (1D). 11 (iv) R 141 ~R 148 , R 14A , R 14B , R 14C , R 14Dand Rc, and (v) Ra and Rb that do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring, one selected from the group consisting of is a single bond bonded to *19, and R that is not a single bond bonded to *19 141 ~R 148 , R 14A , R 14B , R 14C , R 14D and Rc, and Ra and Rb that are not single bonds bonded to *19, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused 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 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms.
[0411] In one aspect of the organic EL element according to the first embodiment, R 148 is a single bond that bonds to *19.
[0412] In one aspect of the organic EL element according to the first embodiment, X in formula (11D) 11 is an oxygen atom.
[0413] In one aspect of the organic EL element according to the first embodiment, n in the formula (1D) is 0.
[0414] In one aspect of the organic EL element according to the first embodiment, A in formula (B1) or formula (B100) 1 , B 1 and C 1 At least one selected from the group consisting of: is a group represented by any one of the formulae (14D), (15D), (16D) and (17D) below.
[0415]
[0416]
[0417]
[0418]
[0419] (In the formulas (14D), (15D), (16D) and (17D), *18 represents L 11 , L 12 or L 13 (vi) R 141 ~R 148 and Rc, and (vii) Ra and Rb that do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring are a single bond bonded to *19, and R that is not a single bond bonded to *19 is 141 ~R 148 and Rc, and Ra and Rb that are not single bonds bonded to *19, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused 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 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms.
[0420] In one aspect of the organic EL element according to the first embodiment, R 141 , R 144 , R 145 , or R 148 is a single bond that bonds to *19.
[0421] In one aspect of the organic EL element according to the first embodiment, Rc in the formula (15D) is a single bond bonded to *19.
[0422] In one aspect of the organic EL element according to the first embodiment, L in formula (B1) or (B100) 11 , L 12 and L 13 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).
[0423]
[0424] In the formulae (L1) to (L10), * indicates a bonding position. The groups represented by the formulae (L1) to (L10) may or may not each independently have one or more of the above-mentioned "optional substituents." The groups represented by the formulae (L1) to (L10) may each independently have one or more deuterium atoms.
[0425] In one aspect of the organic EL element according to the first embodiment, L 11 is a single bond, A 1 is directly bonded to the nitrogen atom of the amino group in formula (B1) or (B100), and L 12 is a single bond, B 1 is directly bonded to the nitrogen atom of the amino group in formula (B1) or (B100), and L 13 is a single bond, C 1 is directly bonded to the nitrogen atom of the amino group in formula (B1) or (B100).
[0426] In one aspect of the organic EL element according to the first embodiment, the hole-transporting region materials (e.g., the first hole-transporting region material and the second hole-transporting region material) are each independently a compound represented by the following formula (B10), (B11), (B12), (B13), (B14), or (B15):
[0427]
[0428]
[0429]
[0430] (In the formulae (B10), (B11), (B12), (B13), (B14), and (B15), L 11 , L 12 , L 13 , A 1 , B 1 and C 1 respectively represent L in the formula (B1) or (B100). 11 , L 12 , L 13 , A 1 , B 1 and C 1 is synonymous with R 1 , R2 , R 3 and R 4 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 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms, 1 are the same or different from each other, and four R 2 are the same or different from each other, and four R 3 are the same or different from each other, and four R 4 are the same or different from each other.)
[0431] In one aspect of the organic EL element according to the first embodiment, the hole-transporting region materials (e.g., the first hole-transporting region material and the second hole-transporting region material) are each independently a compound represented by the following formula (B16), (B17), (B18), (B19), or (B20):
[0432]
[0433]
[0434] (In the formulae (B16), (B17), (B18), (B19) and (B20), A 1 , B 1 and C 1 are A in the formula (B1) or (B100), respectively. 1 , B 1 and C 1 is synonymous with R 1 , R 2 , R 3 and R 4 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 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms, and four R 1 are the same or different from each other, and four R 2 are the same or different from each other, and four R 3 are the same or different from each other, and four R 4are the same or different from each other.)
[0435] In one aspect of the organic EL element according to the first embodiment, R 1 , R 2 and R 3 is a deuterium atom.
[0436] In one aspect of the organic EL element according to the first embodiment, A in the formulas (B1), (B100), (B10), (B11), (B12), (B13), (B14), (B15), (B16), (B17), (B18), (B19), and (B20) 1 , B 1 and C 1 wherein at least one selected from the group consisting of the groups represented by formulas (1A) and (1B) contains at least one group selected from the group consisting of groups represented by formulas (1A) and (1B). Hereinafter, "(B10), (B11), (B12), (B13), (B14), (B15), (B16), (B17), (B18), (B19) and (B20)" may be abbreviated as "(B10) to (B20)."
[0437] In one aspect of the organic EL element according to the first embodiment, A in the formulas (B1), (B10) to (B20) 1 , B 1 and C 1 one selected from the group consisting of: 1 , B 1 and C 1 and the remaining two selected from the group consisting of formulas (1D), (11D), (12D), (13D), (14D), (15D), (16D), and (17D) contain at least one group selected from the group consisting of groups represented by formulas (1D), (11D), (12D), (13D), (14D), (15D), (16D), and (17D).
[0438] In one aspect of the organic EL element according to the first embodiment, A in the formulas (B1), (B100), and (B10) to (B20) 1 , B 1 and C 1and two selected from the group consisting of:
[0439] In one aspect of the organic EL element according to the first embodiment, A in the formulas (B1), (B10) to (B20) 1 , B 1 and C 1 two selected from the group consisting of: 1 , B 1 and C 1 The remaining one selected from the group consisting of each independently contains at least one group selected from the group consisting of groups represented by formulas (1D), (11D), (12D), (13D), (14D), (15D), (16D), and (17D).
[0440] In one aspect of the organic EL element according to the first embodiment, A in the formulas (B1), (B100), and (B10) to (B20) 1 , B 1 and C 1 At least one selected from the group consisting of is a group represented by formula (1G), and X B is an oxygen atom.
[0441] In one aspect of the organic EL element according to the first embodiment, A in the formulas (B1), (B100), and (B10) to (B20) 1 , B 1 and C 1 Two selected from the group consisting of are groups represented by the formula (1G), and X B is an oxygen atom.
[0442] In one aspect of the organic EL element according to the first embodiment, A in the formulas (B1), (B100), and (B10) to (B20) 1 , B 1 and C 1 At least one selected from the group consisting of: contains at least one group selected from the group consisting of groups represented by formulas (11G), (12G) and (13G).
[0443] In one aspect of the organic EL element according to the first embodiment, A in the formulas (B1), (B100), and (B10) to (B20) 1 , B 1 and C 1 and two selected from the group consisting of: containing at least one group selected from the group consisting of groups represented by formulae (11G), (12G) and (13G).
[0444] In one aspect of the organic EL element according to the first embodiment, A in the formulas (B1), (B100), and (B10) to (B20) 1 , B 1 and C 1 At least one selected from the group consisting of: contains at least one group selected from the group consisting of groups represented by formulas (11G-1), (12G-1), (12G-2) and (13G-1).
[0445] In one aspect of the organic EL element according to the first embodiment, A in the formulas (B1), (B100), and (B10) to (B20) 1 , B 1 and C 1 and two selected from the group consisting of the formulae (11G-1), (12G-1), (12G-2) and (13G-1) contain at least one group selected from the group consisting of groups represented by the formulae (11G-1), (12G-1), (12G-2) and (13G-1).
[0446] In one aspect of the organic EL element according to the first embodiment, A in the formulas (B1), (B100), and (B10) to (B20) 1 , B 1 and C 1 At least one selected from the group consisting of has one or more substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms (preferably 1 to 6 carbon atoms) as a substituent.
[0447] In one aspect of the organic EL element according to the first embodiment, A in the formulas (B1), (B100), and (B10) to (B20) 1 , B 1 and C 1 At least one selected from the group consisting of has one or more branched alkyl groups as substituents.
[0448] In one aspect of the organic EL element according to the first embodiment, A in the formulas (B1), (B100), and (B10) to (B20) 1 , B 1 and C 1 At least one selected from the group consisting of has one or more tert-butyl groups as a substituent.
[0449] In one aspect of the organic EL device according to the first embodiment, the hole-transporting material is at least one amine compound selected from the group consisting of monoamine compounds having one substituted or unsubstituted amino group in the molecule, diamine compounds having two substituted or unsubstituted amino groups in the molecule, triamine compounds having three substituted or unsubstituted amino groups in the molecule, and tetraamine compounds having four substituted or unsubstituted amino groups in the molecule.
[0450] In one aspect of the organic EL device according to the first embodiment, the first hole transporting region material and the second hole transporting region material are each independently a monoamine compound or a diamine compound.
[0451] In one aspect of the organic EL device according to the first embodiment, the first hole transporting region material and the second hole transporting region material are each independently a monoamine compound.
[0452] (Method for producing the hole transport material according to this embodiment) The hole transport material according to this embodiment can be produced by a known method. The hole transport material according to this embodiment can also be produced by following a known method and using known alternative reactions and raw materials suited to the target. (Specific examples of the hole transport material according to this embodiment) Specific examples of the hole transport material according to this embodiment include the following compounds. However, the present invention is not limited to these specific examples.
[0453]
[0454]
[0455]
[0456]
[0457]
[0458]
[0459]
[0460]
[0461]
[0462]
[0463]
[0464]
[0465]
[0466]
[0467]
[0468]
[0469]
[0470]
[0471]
[0472]
[0473]
[0474]
[0475]
[0476]
[0477]
[0478]
[0479]
[0480]
[0481]
[0482]
[0483]
[0484]
[0485]
[0486]
[0487]
[0488]
[0489]
[0490]
[0491]
[0492]
[0493]
[0494]
[0495]
[0496]
[0497]
[0498]
[0499]
[0500]
[0501]
[0502]
[0503]
[0504]
[0505]
[0506]
[0507]
[0508]
[0509]
[0510]
[0511]
[0512]
[0513]
[0514]
[0515]
[0516]
[0517]
[0518]
[0519]
[0520]
[0521]
[0522]
[0523]
[0524]
[0525]
[0526]
[0527]
[0528]
[0529]
[0530]
[0531]
[0532]
[0533]
[0534]
[0535]
[0536]
[0537]
[0538]
[0539]
[0540]
[0541]
[0542]
[0543]
[0544]
[0545]
[0546]
[0547]
[0548]
[0549]
[0550]
[0551]
[0552]
[0553]
[0554]
[0555]
[0556]
[0557]
[0558]
[0559]
[0560]
[0561]
[0562] <Hole Transport Layer> The hole transport layer is a layer containing a substance with high hole transport properties. In one aspect of the organic EL device according to the first embodiment, the hole transport layer (e.g., the first hole transport layer and the second hole transport layer) may contain a compound different from the hole transport material described above. For example, the hole transport layer may contain one or more compounds selected from the group consisting of aromatic amine compounds, carbazole derivatives, and anthracene derivatives. Specific examples of the hole transport layer include 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: NPB), and the like. Examples of aromatic amine compounds that can be used include 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The substances mentioned here are mainly 10 -6 cm 2The hole-transporting layer may be a material having a hole mobility of 1 / (V·s) or more. For the hole-transporting layer, carbazole derivatives such as CBP, CzPA, and PCzPA, or anthracene derivatives such as t-BuDNA, DNA, and DPAnth may be used. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) may also be used. However, other materials may also be used as long as they have a higher hole-transporting property than electron-transporting property. The layer containing the material having a high hole-transporting property may be a single layer or a layer in which two or more layers made of the above-mentioned materials are stacked.
[0563] In one aspect of the organic EL element according to the first embodiment, the hole transport region may include one hole transport layer or two or more hole transport layers.
[0564] (Other Specific Examples of Hole Transporting Zone Materials) In addition to the above-described hole transporting zone materials, other specific examples of hole transporting zone materials include the following compounds. However, the present invention is not limited to these specific examples of hole transporting zone materials.
[0565]
[0566]
[0567] <Electron Blocking Layer> The electron blocking layer is preferably a layer that transports holes and blocks electrons from reaching a layer (e.g., a hole transport layer) closer to the anode than the electron blocking layer. In one aspect of the organic EL device according to the first embodiment, the first light-emitting unit includes a first electron blocking layer, and the second light-emitting unit includes a second electron blocking layer. In one aspect of the organic EL device according to the first embodiment, the compound contained in the electron blocking layer (e.g., the first electron blocking layer and the second electron blocking layer) is a hole-transporting material. In one aspect of the organic EL device according to the first embodiment, the compound contained in the electron blocking layer is a compound represented by formula (B1) or (B100). In one aspect of the organic EL device according to the first embodiment, the compound contained in the electron blocking layer is a compound used in known electron blocking layers, and is at least one compound selected from the group consisting of aromatic amine compounds and carbazole derivatives. The compound contained in the electron blocking layer may also be a monoamine compound having only one substituted or unsubstituted amino group in the molecule. The compound contained in the electron blocking layer may have a substituted or unsubstituted carbazolyl group and one substituted or unsubstituted amino group in the molecule. The electron blocking layer may be a layer that prevents excitons generated in the light-emitting layer from migrating to a layer closer to the anode than the electron blocking layer (for example, a hole-transporting layer or a hole-injecting layer) so as to prevent excitation energy from leaking from the light-emitting layer to a peripheral layer.
[0568] <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 region, or between the charge generation region and the light-emitting region located closer to the cathode than the charge generation region. The hole injection layer is a layer containing a substance with high hole injection properties. Examples of the substance with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide. Furthermore, examples of the material with high hole injection properties include low-molecular-weight organic compounds such as 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), and 1, Examples of the aromatic amine compound include 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), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1). Furthermore, a polymer compound (such as an oligomer, dendrimer, or polymer) can also be used as the substance with high hole injection properties.Examples of such polymer compounds include 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), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD). Furthermore, polymer compounds to which an acid has been added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.
[0569] In one aspect of the organic EL device according to this embodiment, a compound (hole-transporting material) that can be used in the hole-transporting layer can also be used in the hole-injecting layer. In this case, the hole-injecting layer preferably contains a hole-transporting material and an acceptor material.
[0570] (Acceptor Material) The acceptor material contains 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).
[0571]
[0572] (The first ring structure represented by the formula (P11) is fused with at least one ring structure selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms in the molecule of the acceptor material, and =Z 10 The structure represented by the formula (P11a), (P11b), (P11c), (P11d), (P11e), (P11f), (P11g), (P11h), (P11i), (P11j), (P11k) or (P11m) is represented by the following formula:
[0573]
[0574]
[0575] (In the formula (P11a), (P11b), (P11c), (P11d), (P11e), (P11f), (P11g), (P11h), (P11i), (P11j), (P11k), or (P11m), R 11 ~R 14 and R 111 ~R 120 are 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 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 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.
[0576] (In the formula (P12), Z 1 ~Z 5 are each independently a nitrogen atom, R 15 or a carbon atom bonded to another atom in a molecule of the acceptor material, 1 ~Z 5 at least one of R is a carbon atom bonded to another atom in the molecule of the acceptor material; 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 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, -Si(R 901 ) (R 902 ) (R 903a group represented by —O—(R 904 a group represented by —S—(R 905 a group represented by —N(R 906 ) (R 907 ), a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a carboxy group, a substituted or unsubstituted ester group, a substituted or unsubstituted carbamoyl group, a nitro group, and a substituted or unsubstituted siloxanyl group; R 15 If there are multiple R 15 are the same or different.)
[0577] (In the acceptor material, 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 carbon atoms, 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 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 906 If there are multiple R 906 are the same or different from each other, R 907 If there are multiple R 907 are the same or different from each other.)
[0578] In one aspect of the organic EL device according to this embodiment, the acceptor material has at least one cyano group.
[0579] In one aspect of the organic EL element according to this embodiment, the hole injection layer contains a hole transporting zone material, the acceptor material and the hole transporting zone material are different from each other, and the content of the acceptor material in the hole injection layer is less than 50% by mass.
[0580] 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.
[0581] 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.
[0582] In one aspect of the organic EL device according to this embodiment, when the hole injection layer contains an acceptor material and a hole transport material, the content of the hole transport material in the hole injection layer is preferably 40% by mass or more, more preferably 45% by mass or more, and even more preferably 50% by mass or more. The content of the hole transport 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 material in the hole injection layer is 100% by mass or less.
[0583] The ester group in this specification is at least one group selected from the group consisting of an alkyl ester group and an aryl ester group.
[0584] The alkyl ester group herein is, for example, —C(═O)OR E It is expressed as: R E is, for example, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 10 carbon atoms).
[0585] The aryl ester group herein is, for example, —C(═O)OR Ar It is expressed as: R Ar is, for example, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
[0586] The siloxanyl group in this specification is a silicon compound group connected via an ether bond, such as a trimethylsiloxanyl group.
[0587] In this specification, the carbamoyl group is —CONH 2 The substituted carbamoyl group herein is represented by, for example, —CONH-Ar C , or -CONH-R C It is expressed as: Ar C is, for example, at least one group selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 50 ring carbon atoms (preferably 6 to 10 ring carbon atoms) and heterocyclic groups having 5 to 50 ring atoms (preferably 5 to 14 ring atoms). C may be a group in which a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms is bonded to a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. C is, for example, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 6 carbon atoms).
[0588] In the acceptor material, it is also preferred that any groups described as "substituted or unsubstituted" are "unsubstituted" groups.
[0589] (Specific Examples of Acceptor Materials) Specific examples of acceptor materials include the following compounds: However, the present invention is not limited to these specific examples of acceptor materials.
[0590]
[0591]
[0592] <Other Configurations of Organic EL Element> The configuration of the organic EL element will be further described.
[0593] (Substrate) The substrate is used as a support for the organic EL element. For example, glass, quartz, plastic, etc. can be used as the substrate. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate. Examples of materials for forming the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Inorganic vapor deposition films can also be used.
[0594] (Anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a large work function (specifically, 4.0 eV or more). Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metal materials (e.g., titanium nitride). These materials are typically deposited by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1% by mass to 10% by mass of zinc oxide added to indium oxide. Furthermore, for example, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5% by mass to 5% by mass of tungsten oxide and 0.1% by mass to 1% by mass of zinc oxide relative to indium oxide. Other methods for preparation include vacuum deposition, coating, inkjet printing, and spin coating. Of 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, and therefore, materials that can be used as electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, including elements belonging to Group 1 or Group 2 of the periodic table) can be used. It is also possible to use materials with small work functions, such as elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.When an alkali metal, an alkaline earth metal, or an alloy containing these is used to form the anode, a vacuum deposition method or a sputtering method can be used. Furthermore, when a silver paste or the like is used, a coating method or an inkjet method can be used.
[0595] When the organic EL element is a bottom-emission type, the anode is a light-transmitting electrode having light transparency. The light-transmitting electrode is preferably formed of a light-transmitting or semi-transmitting metal material that transmits light emitted from the light-emitting layer. In this specification, light-transmitting or semi-transmitting means the property of transmitting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The light-transmitting or semi-transmitting metal material can be appropriately selected from the materials listed in the anode section. The light-transmitting or semi-transmitting metal material may be a material listed as a material used for the conductive layer (or transparent conductive layer) described below.
[0596] When the organic EL element is a top-emission type, the anode is a light-reflective electrode having a light-reflective layer. The light-reflective layer is preferably formed of a metal material having light reflectivity. In this specification, light reflectivity refers to the property of reflecting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The light-reflective metal material can be appropriately selected from the materials listed in the anode section. Examples of metal materials used for the light-reflective layer include a simple metal material selected from the group consisting of Al, Ag, Ta, Zn, Mo, W, Ni, and Cr, or an alloy material containing a metal selected from this group as the main component (preferably 50% by mass or more of the total); an amorphous alloy selected from the group consisting of NiP, NiB, CrP, and CrB; a microcrystalline alloy selected from the group consisting of NiAl and a silver alloy; and the like. The metal material used for the light-reflecting layer may be at least one alloy selected from the group consisting of APC (an alloy of silver, palladium, and copper), ARA (an alloy of silver, rubidium, and gold), MoCr (an alloy of molybdenum and chromium), and NiCr (an alloy of nickel and chromium). The light-reflecting layer may be a single layer or multiple layers.
[0597] The anode as a light-reflective electrode may be composed of only a light-reflecting layer, or may have a multilayer structure including a light-reflecting layer and a conductive layer (preferably a transparent conductive layer). When the anode has a light-reflecting layer and a conductive layer, the conductive layer is preferably disposed between the reflective layer and a layer containing a hole-transporting region (e.g., a hole-injection layer or a hole-transporting layer). The anode may also have a multilayer structure in which a light-reflecting layer is disposed between two conductive layers (a first conductive layer and a second conductive layer). In such a multilayer structure, the first conductive layer and the second conductive layer may be formed of the same material or different materials. The material used for the conductive layer can be appropriately selected from the materials listed in the anode section. Furthermore, the conductive layer (transparent conductive layer) as a transparent electrode may also be formed of a metal, alloy, electrically conductive compound, or mixture thereof having a high work function (specifically, 4.0 eV or more). The conductive layer may also be made of, 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 (e.g., MgAg and AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing at least one selected from rare earth metals.
[0598] (Cathode) For the cathode, it is preferable to use metals, alloys, electrically conductive compounds, 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 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), and ytterbium (Yb), and alloys containing these. When forming a cathode using alkali metals, alkaline earth metals, or alloys containing these, vacuum deposition or sputtering can be used. When using silver paste or the like, coating or inkjet printing can be used. By providing an electron injection layer, it is possible to form a cathode using various conductive materials, regardless of the magnitude of the work function, such as Al, Ag, ITO, graphene, and indium oxide-tin oxide containing silicon or silicon oxide. These conductive materials can be formed into films by sputtering, ink jetting, spin coating, or the like.
[0599] When the organic EL element is a bottom-emission type, the cathode is a light-reflective electrode. The light-reflective electrode is preferably formed of a metal material having light reflectivity. The light-reflective metal material can be appropriately selected from the materials listed in the cathode section. In addition, the light-reflective metal material may be the material listed as the metal material used for the light-reflecting layer.
[0600] When the organic EL element is a top-emission type, the cathode is a light-transmitting electrode having light transparency. The light-transmitting electrode is preferably formed of a light-transmitting or semi-transmitting metal material that transmits light emitted from the light-emitting layer. Light-transmitting or semi-transmitting means the property of transmitting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The light-transmitting or semi-transmitting metal material can also be appropriately selected from the materials listed in the section on the cathode. The light-transmitting or semi-transmitting metal material may be the material listed as the material used for the conductive layer (or transparent conductive layer) described above.
[0601] (Capping Layer) When the organic EL element is a top-emission type, the organic EL element usually has a capping layer on the cathode. The capping layer may contain, for example, at least one compound selected from the group consisting of polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitride, and silicon compounds (such as silicon oxide). The capping layer may also contain, for example, at least one compound selected from the group consisting of aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, or dibenzofuran derivatives. A laminate obtained by stacking layers containing these substances can also be used as the capping layer.
[0602] The organic EL element according to this embodiment may be a bottom-emission organic EL element. The organic EL element according to this embodiment may also be a top-emission organic EL element. When the organic EL element is a bottom-emission type, it is preferable that the anode is a light-transmitting electrode having light transparency, and the cathode is a light-reflective electrode having light reflectivity. When the organic EL element is a top-emission type, it is preferable that the anode is a light-reflective electrode having light reflectivity, and the cathode is a light-transmitting electrode having light transparency.
[0603] (Electron Transport Layer) The electron transport layer is a layer containing a substance with high electron transport properties. Examples of the "compound contained in the electron transport layer" include: 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex; 2) a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative, or a phenanthroline derivative; or 3) a polymer compound. Specifically, examples of low-molecular organic compounds include Alq and tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq). 3 ), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq 2 ), BAlq, Znq, ZnPBO, ZnBTZ, and other metal complexes can be used. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-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: OXD-8), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-9 ... Heteroaromatic compounds such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) can also be used. The substances mentioned here are mainly 10 -6 cm 2 / (V s) or more. Note that other substances may be used as the electron-transporting layer as long as they have a higher electron-transporting property than a hole-transporting property. The electron-transporting layer may be a single layer or a stack of two or more layers made of the above-mentioned substances. A polymer compound may also be used for the electron-transporting 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), or the like may be used.
[0604] (Hole Blocking Layer) The hole blocking layer is preferably a layer that transports electrons and prevents holes from reaching a layer closer to the cathode than the hole blocking layer (e.g., an electron transport layer). The "compound contained in the hole blocking layer" is, for example, a compound used in known hole blocking layers. The compound contained in the hole blocking layer is also preferably at least one compound selected from the group consisting of metal complexes, heteroaromatic compounds, and polymer compounds. The compound contained in the hole blocking layer may also be at least one compound selected from the group consisting of imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives. The hole blocking layer is also preferably a layer that prevents excitons generated in the light-emitting layer from migrating to a layer closer to the cathode than the hole blocking layer (e.g., an electron transport layer or an electron injection layer) to prevent excitation energy from leaking from the light-emitting layer to a peripheral layer.
[0605] (Electron Injection Layer) The electron injection layer is a layer containing a substance with high electron injection properties. Examples of the electron injection layer include lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), and calcium fluoride (CaF 2Alkali metals, alkaline earth metals, or compounds thereof, such as lithium oxide (LiOx), may be used. Alternatively, a material having electron transport properties containing an alkali metal, alkaline earth metal, or compound thereof, such as magnesium (Mg) in Alq, may be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, a composite material containing an organic compound and an electron donor (donor) may be used for the electron injection layer. Such composite materials have excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material that is excellent at transporting the generated electrons. Specifically, the above-mentioned materials constituting the electron transport layer (e.g., metal complexes and heteroaromatic compounds) may be used. The electron donor may be any material that exhibits electron donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. In addition, alkali metal oxides and alkaline earth metal oxides are preferred, such as lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (abbreviated as TTF) can also be used.
[0606] (Example of Schematic Configuration of Organic EL Element) FIG. 1 shows a schematic configuration of an example of an organic EL element according to this embodiment. The organic EL element 100 shown in FIG. 1 includes a substrate 20, an anode 30, a cathode 40, and an organic layer 10A disposed between the anode 30 and the cathode 40. The organic layer 10A includes, in order from the anode 30 side, a first light-emitting unit 110, a first charge-generation zone 810, and a second light-emitting unit 120. The first light-emitting unit 110, the first charge-generation zone 810, and the second light-emitting unit 120 are disposed in this order from the anode 30 side. The organic EL element 100 also includes a capping layer 90 on the surface of the cathode 40 opposite to the surface facing the second light-emitting unit 120. The first light-emitting unit 110 includes, in order from the anode 30 side, a first hole-transporting zone 610, a first light-emitting zone 510, and a first electron-transporting zone 710. The first hole-transporting region 610 includes, in order from the anode 30 side, a first hole-injection layer 613, a first hole-transporting layer 612, and a first electron-blocking layer 611. The first light-emitting region 510 includes a first light-emitting layer 511. The first electron-transporting region 710 includes an light-emitting-layer-side electron-transporting layer (first electron-transporting layer in the case of FIG. 1 ) 712. The first charge-generating region 810 includes, in order from the first light-emitting unit 110 side, a cathode-side electron-transporting layer (first charge-generating layer in the case of FIG. 1 ) 811 and a second charge-generating layer 812. The first light-emitting layer 511 and the light-emitting-layer-side electron-transporting layer 712 are in direct contact. The second light-emitting unit 120 includes, in order from the first charge-generating region 810 side, a second hole-transporting region 620, a second light-emitting region 520, and a second electron-transporting region 720. The second hole-transporting zone 620 includes, in order from the first charge-generating zone 810 side, a second hole-transporting layer 622 and a second electron-blocking layer 621. The second light-emitting zone 520 includes a second light-emitting layer 521. The second electron-transporting zone 720 includes, in order from the second light-emitting zone 520, a second hole-blocking layer 721, a second electron-transporting layer 722, and a second electron-injecting layer 723. The present invention is not limited to the configuration of the organic EL element shown in FIG.
[0607] (Layer Formation Method) The method for forming each layer of the organic EL device of this embodiment is not limited to those specifically mentioned above, and known methods can be used, such as dry film-forming methods such as vacuum deposition, sputtering, plasma deposition, and ion plating, and wet film-forming methods such as spin coating, dipping, flow coating, and inkjet deposition. In the organic EL device of this embodiment, a layer containing multiple substances can be formed, for example, by co-evaporation using multiple compounds, or by evaporation using a premixed mixture of multiple compounds, or by coating using a premixed mixture of multiple compounds. The premixed mixture of multiple compounds may be in the form of a powder. The premixed mixture of multiple compounds may be in the form of a solution. The method of premixing multiple compounds is sometimes referred to as "premixing." The premixing method is not particularly limited, and the evaporation ratio of the compounds constituting the premixed mixture can be adjusted, for example, by adjusting the molecular weight of the compounds by adjusting the substituents of the compounds constituting the mixture, or by adjusting the mixing ratio.
[0608] (Film Thickness) In the organic EL element of the present embodiment, the film thickness of each of the organic compound layers is not limited unless specifically mentioned above. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and if the film thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, the film thickness of each of the organic compound layers of the organic EL element is usually preferably in the range of several nm to 1 μm.
[0609] (Emission Wavelength of Organic EL Element) The organic EL element according to one aspect of this embodiment emits blue, green, red, or white light. In this specification, blue emission refers to emission having a maximum peak wavelength in the emission spectrum ranging from 430 nm to 480 nm. In this specification, green emission refers to emission having a maximum peak wavelength in the emission spectrum ranging from 500 nm to 560 nm. In this specification, red emission refers to emission having a maximum peak wavelength in the emission spectrum ranging from 600 nm to 660 nm. The maximum peak wavelength is the peak wavelength at which the emission intensity is greatest in the emission spectrum.
[0610] In one aspect of the organic EL element according to this embodiment, the maximum peak wavelength of light emitted from the organic EL element is 430 nm or more and 480 nm or less.
[0611] In one aspect of the organic EL element according to this embodiment, the maximum peak wavelength of light emitted from the organic EL element is 500 nm or more and 560 nm or less.
[0612] In one aspect of the organic EL element according to this embodiment, the maximum peak wavelength of light emitted from the organic EL element is 600 nm or more and 660 nm or less.
[0613] The maximum peak wavelength of light emitted from the organic EL element when the element is driven is measured as follows: 2 A voltage is applied to the organic EL element so that the spectral radiance spectrum obtained is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is measured, and this is defined as the maximum peak wavelength (unit: nm).
[0614] In one aspect of the organic EL element according to the first embodiment, the plurality of light-emitting units each independently emit blue, red, or green light. When each of the plurality of light-emitting units of the organic EL element according to the first embodiment emits green, red, or blue light, the maximum peak wavelength of light emitted from each light-emitting unit is the same as the maximum peak wavelength when the light emitted from the organic EL element is green, red, or blue, respectively. The maximum peak wavelength of light emitted from the light-emitting units of the organic EL element when the element is driven can be measured, for example, by performing a measurement similar to the method for measuring the maximum peak wavelength of an organic EL element on an element configuration excluding light-emitting units other than the light-emitting unit being measured.
[0615] [Second embodiment] <Organic electroluminescence element> The configuration of an organic EL element according to a second embodiment will be described. In the description of the second embodiment, the same components as those in the first embodiment will be denoted by the same reference numerals or names, and the description thereof will be omitted or simplified. Furthermore, in the second embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the first embodiment can be used.
[0616] The organic EL element according to the second embodiment is an organic EL element having one light-emitting unit. The other points are the same as those of the first embodiment. The organic electroluminescent element according to the second embodiment has an anode, a cathode, and a first light-emitting zone disposed between the anode and the cathode. A first electron-transporting zone is disposed between the first light-emitting zone and the cathode. The first electron-transporting zone includes one or more layers, one of which is an light-emitting-layer-side electron-transporting layer that is in direct contact with the first light-emitting zone. A cathode-side electron-transporting layer is disposed between the first electron-transporting zone and the cathode. The light-emitting-layer-side electron-transporting layer contains a first electron-transporting zone material. The first electron-transporting zone material is a compound having a fused polycyclic skeleton and satisfies the following mathematical formulas (Mathematical Formula 1) and (Mathematical Formula 2). T 1 (E1) ≧ 1.90 eV (Equation 1) Af(E1) ≧ 1.55 eV (Equation 2) (T 1(E1) is the triplet energy of the first electron transporting band material, and Af(E1) is the affinity of the first electron transporting band material.
[0617] The present inventors have found that by adjusting the triplet energy and affinity of the first electron-transporting region material, the recombination probability of carriers in the first emission region in the light-emitting layer can be increased, thereby improving the TTF efficiency. The organic EL device according to the second embodiment can improve the external quantum efficiency.
[0618] <First Emission Band> In the organic EL element according to the second embodiment, the first emission band preferably has the same configuration as the first emission band described in the first embodiment. The first emission band includes at least one emission layer (e.g., a first emission layer). In one aspect of the organic EL element according to the second embodiment, the emission layer included in the first emission band preferably has the same configuration as the first emission layer described in the first embodiment.
[0619] <First Electron Transporting Zone> In one aspect of the organic EL element according to the second embodiment, the light-emitting layer-side electron transporting layer is a first electron transporting layer. This light-emitting layer-side electron transporting layer may be a hole-blocking layer. In one aspect of the organic EL element according to the second embodiment, the cathode-side electron transporting layer and the first electron transporting zone are in direct contact with each other. In one aspect of the organic EL element according to the second embodiment, the cathode-side electron transporting layer and the first electron transporting zone do not have to be in direct contact with each other.
[0620] In one aspect of the organic EL element according to the second embodiment, the first light-emitting layer and the light-emitting-layer-side electron-transporting layer are in direct contact with each other. In one aspect of the organic EL element according to the second embodiment, the first electron-transporting region includes two or more layers, one of which is the light-emitting-layer-side electron-transporting layer.
[0621] In one aspect of the organic EL element according to the second embodiment, the light-emitting layer-side electron-transporting layer contains a first electron-transporting region material.
[0622] In one aspect of the organic EL element according to the second embodiment, the first electron-transporting region includes one layer, and the one layer is a first hole-blocking layer or a first electron-transporting layer. In one aspect of the organic EL element according to the second embodiment, the first electron-transporting region includes one layer, and the one layer is a first hole-blocking layer, and the first hole-blocking layer and the cathode-side electron-transporting layer are in direct contact with each other. In one aspect of the organic EL element according to the second embodiment, the first electron-transporting region includes one layer, and the one layer is a first electron-transporting layer, and the first electron-transporting layer and the cathode-side electron-transporting layer are in direct contact with each other.
[0623] In one aspect of the organic EL element according to the second embodiment, the first electron-transporting region includes, in order from the first emission region side, a first hole-blocking layer and a first electron-transporting layer. In one aspect of the organic EL element according to the second embodiment, the first hole-blocking layer is an emission-layer-side electron-transporting layer. In one aspect of the organic EL element according to the second embodiment, the first hole-blocking layer and the first emission region are in direct contact with each other, and the first electron-transporting layer and the cathode-side electron-transporting layer are in direct contact with each other.
[0624] In one aspect of the organic EL element according to the second embodiment, the first hole blocking layer contains a first electron transporting region material. In one aspect of the organic EL element according to the second embodiment, the first electron transporting region material. The first electron transporting region material contained in the first hole blocking layer and the first electron transporting region material contained in the first electron transporting region material may be the same compound or different compounds.
[0625] In the organic EL element according to the second embodiment, the first electron-transporting region material contained in the light-emitting layer-side electron-transporting layer preferably satisfies the above-described formula (Mathematical Formula 1A), and more preferably satisfies the above-described formula (Mathematical Formula 1B).
[0626] In one aspect of the organic EL element according to the second embodiment, when the first electron-transporting region includes a first electron-transporting layer, the triplet energy T 1 (H1) and the triplet energy T of the first electron transport band material contained in the first electron transport layer 1 (E ET 1) satisfies the relationship of the above-mentioned formula (Formula 1A).
[0627] In one aspect of the organic EL element according to the second embodiment, when the first electron-transporting region includes a first hole-blocking layer, the triplet energy T 1 (H1) and the triplet energy T of the first electron transporting region material contained in the first hole blocking layer 1 (E HB 1) satisfies the relationship of the above-mentioned formula (Formula 1B).
[0628] In one aspect of the organic EL element according to the second embodiment, the relationships of both the above-mentioned formula (1A) and formula (1B) are satisfied.
[0629] In the organic EL element according to the second embodiment, the first electron-transporting region material contained in the light-emitting layer-side electron-transporting layer preferably satisfies the above-described formula (Formula 2A), and more preferably satisfies the above-described formula (Formula 21).
[0630] In one aspect of the organic EL element according to the second embodiment, the affinity Af(H1) of the first host material contained in the first emitting layer and the affinity Af(E1) of the first electron-transporting region material contained in the emitting-layer-side electron-transporting layer satisfy the relationship of the above-mentioned mathematical formula (Mathematical Formula 3). In one aspect of the organic EL element according to the second embodiment, the affinity Af(H1) of the first host material and the affinity Af(E1) of the first electron-transporting region material satisfy the relationship of the above-mentioned mathematical formula (Mathematical Formula 3A), (Mathematical Formula 3B), (Mathematical Formula 3C), (Mathematical Formula 3D), (Mathematical Formula 3E), (Mathematical Formula 3F), or (Mathematical Formula 3G).
[0631] In one aspect of the organic EL element according to the second embodiment, the emitter-side electron transport layer preferably has the same configuration as the emitter-side electron transport layer described in the first embodiment. In one aspect of the organic EL element according to the second embodiment, the emitter-side electron transport layer is, for example, the first electron transport layer described in the first embodiment. The first electron transport layer may be a hole-blocking layer. In one aspect of the organic EL element according to the second embodiment, materials that can be used for the emitter-side electron transport layer include, for example, known materials that can be used for the emitter-side electron transport layer of a tandem organic EL element. In one aspect of the organic EL element according to the second embodiment, the emitter-side electron transport layer contains a first electron-transporting region material. The first electron-transporting region material can be, for example, the first electron-transporting region material described in the first embodiment.
[0632] In one aspect of the organic EL element according to the second embodiment, the first electron-transporting region material contained in the emission-layer-side electron-transporting layer is not a compound having an anthracene skeleton. In the organic EL element according to the second embodiment, the first electron-transporting region material is a compound having a fused polycyclic skeleton. The fused polycyclic skeleton is preferably a fused aromatic hydrocarbon ring having from 10 to 30 ring carbon atoms or a fused aromatic heterocycle having from 14 to 30 ring atoms, and at least one of the fused polycyclic skeletons is more preferably at least one ring selected from the group consisting of a pyrene ring, a fluoranthene ring, a benzofluoranthene ring, a phenanthrene ring, a benzophenanthrene ring, a chrysene ring, a benzochrysene ring, a triphenylene ring, a benzotriphenylene ring, a benzoxanthene ring, and a benzanthracene ring.
[0633] In one aspect of the organic EL element according to the second embodiment, the cathode-side electron transport layer preferably has the same configuration as the cathode-side electron transport layer described in the first embodiment. In one aspect of the organic EL element according to the second embodiment, the cathode-side electron transport layer is a layer that supplies electrons to a layer located on the anode side, and is, for example, an N-type charge generation layer. The N-type charge generation layer corresponds to the first charge generation layer or the second electron injection layer described in the first embodiment. In one aspect of the organic EL element according to the second embodiment, materials that can be used for the cathode-side electron transport layer include, for example, known materials that can be used for the cathode-side electron transport layer of a tandem organic EL element. In one aspect of the organic EL element according to the second embodiment, the cathode-side electron transport layer contains a first charge generation material. The first charge generation material can be, for example, the first charge generation material described in the first embodiment. In one aspect of the organic EL element according to the second embodiment, the material that can be used for the cathode-side electron transport layer can be, for example, a known material that can be used for the electron injection layer described in the first embodiment.
[0634] In one aspect of the organic EL element according to the second embodiment, the cathode-side electron transport layer and the emitter-side electron transport layer do not need to be in direct contact with each other. In one aspect of the organic EL element according to the second embodiment, another layer (e.g., an electron transport layer) may be disposed between the cathode-side electron transport layer and the emitter-side electron transport layer. For example, when the other layer is an electron transport layer, materials that can be used for the electron transport layer include, for example, known materials that can be used for the electron transport layers described in the first embodiment (e.g., the first electron transport layer and the second electron transport layer).
[0635] (Example of Schematic Configuration of Organic EL Element) Figure 2 shows a schematic configuration of an example of an organic EL element according to the second embodiment. The organic EL element 1 shown in Figure 2 includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 includes, in order from the anode 3 side, a first hole transporting zone 6, a first light-emitting zone 5, and a first electron transporting zone 7. The first hole transporting zone 6, the first light-emitting zone 5, and the first electron transporting zone 7 are disposed in this order from the anode 3 side. The first hole transporting zone 6 includes, in order from the anode 3 side, a first hole injection layer 63, a first hole transporting layer 62, and a first electron blocking layer 61. The first light-emitting zone 5 includes a first light-emitting layer 50. The first electron-transporting region 7 includes, in order from the anode 3 side, an emission-layer-side electron-transporting layer (first electron-transporting layer in the case of FIG. 2 ) 71 and a cathode-side electron-transporting layer (first electron-injection layer in the case of FIG. 2 ). The first emission layer 50 and the emission-layer-side electron-transporting layer 71 are in direct contact with each other. The present invention is not limited to the configuration of the organic EL element shown in FIG. 2 .
[0636] Third Embodiment (Electronic Device) An electronic device according to this embodiment is equipped with an organic electroluminescence element according to the above-described embodiment. Examples of the electronic device include a display device and a light-emitting device. Examples of the display device include display components (e.g., an organic EL panel module), televisions, mobile phones, tablets, and personal computers. Examples of the light-emitting device include lighting and vehicle lighting fixtures. The light-emitting device can be used in a display device, and can also be used, for example, as a backlight for a display device.
[0637] [Modifications of the Embodiment] The present invention is not limited to the above-described embodiment, and any modifications, improvements, etc. that can achieve the object of the present invention are included in the present invention.
[0638] For example, the number of light-emitting layers is not limited to one or two, and more than two light-emitting layers may be stacked. For example, the other light-emitting layer may be a fluorescent light-emitting layer or a phosphorescent light-emitting layer that utilizes light emission due to electron transition from a triplet excited state directly to the ground state.
[0639] In addition, the specific structure and shape in carrying out the present invention may be other structures within the scope that the object of the present invention can be achieved.
[0640] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples in any way.
[0641] <Compounds> The structures of the first electron-transporting region materials used in the production of the organic EL devices according to Examples 1 to 5 are shown below.
[0642]
[0643]
[0644] The structure of the comparative compound used in the production of the organic EL device according to Comparative Example 1 is shown below.
[0645]
[0646] The structures of other compounds used in the production of the organic EL devices according to Examples 1 to 5 and Comparative Example 1 are shown below.
[0647]
[0648]
[0649] <Fabrication of Organic EL Device> [Example 1] A substrate for fabricating an element was prepared by laminating, in this order, a metal Ag layer as a reflective layer and an ITO layer as a transparent conductive layer with a thickness of 10 nm on a glass substrate (25 mm × 75 mm × 0.7 mm). In this substrate for fabricating an element, the conductive material layer consisted of the metal Ag layer and the ITO layer. Subsequently, using conventional lithography techniques, this conductive material layer was patterned by etching using a resist pattern as a mask to form a lower electrode (anode).
[0650] (First Light-Emitting Unit) Compound HT1 and compound HA were co-deposited to cover the lower electrode (anode) to form a first hole injection layer with a thickness of 10 nm. The proportion of compound HT1 in this first hole injection layer was 97% by mass, and the proportion of compound HA was 3% by mass. Compound HT1 was deposited on the first hole injection layer to form a first hole transport layer with a thickness of 25 nm. Next, compound EBL1 was deposited on the first hole transport layer to form a first electron blocking layer with a thickness of 5 nm. Compound BH as a first host material and compound BD as a first light-emitting compound were co-deposited on the first electron blocking layer to form a first light-emitting layer with a thickness of 19 nm. The proportion of compound BH in this first light-emitting layer was 99% by mass, and the proportion of compound BD was 1% by mass. On the first light-emitting layer, compound ET-11 was deposited as a first electron-transporting region material to form a 15-nm-thick light-emitting layer-side electron-transporting layer (first electron-transporting layer). In this manner, a first light-emitting unit including the first hole-injection layer, the first hole-transporting layer, the first electron-blocking layer, the first light-emitting layer, and the light-emitting-layer-side electron-transporting layer was formed.
[0651] (First Charge Generation Zone) On the light-emitting layer-side electron transport layer of the first light-emitting unit, compound Ref-1 as a first charge generation zone material and ytterbium (Yb) were co-deposited to form a cathode-side electron transport layer (first charge generation layer) with a film thickness of 7.5 nm. The proportion of compound Ref-1 in the cathode-side electron transport layer was 97.5 mass%, and the proportion of Yb was 2.5 mass%. Next, on the cathode-side electron transport layer, compound HT3 and compound HA as second charge generation zone materials were co-deposited to form a second charge generation layer with a film thickness of 10 nm. The proportion of compound HT3 in this second charge generation layer was 93 mass%, and the proportion of compound HA was 7 mass%. As described above, a first charge generation zone including a cathode-side electron transport layer and a second charge generation layer was formed.
[0652] (Second Light-Emitting Unit) Compound HT3 was deposited on the second charge generating layer in the first charge generating zone to form a second hole transport layer with a thickness of 40 nm. Next, compound EBL1 was deposited on the second hole transport layer to form a second electron blocking layer with a thickness of 5 nm. Compound BH as a second host material and compound BD as a second light-emitting compound were co-deposited on the second electron blocking layer to form a second light-emitting layer with a thickness of 19 nm. The proportion of compound BH in this second light-emitting layer was 99% by mass, and the proportion of compound BD was 1% by mass. Compound HBL2 was deposited on the second light-emitting layer to form a second hole blocking layer with a thickness of 5 nm. Compound ET2 and Liq were co-deposited on the second hole blocking layer to form a second electron transport layer with a thickness of 31 nm. The proportion of compound ET2 in this second electron transport layer was 50% by mass, and the proportion of Liq was 50% by mass. Note that Liq is an abbreviation for (8-quinolinolato)lithium. A second electron injection layer with a film thickness of 1 nm was formed on the second electron transport layer by vapor deposition of ytterbium (Yb). As described above, a second light-emitting unit including a second hole transport layer, a second electron blocking layer, a second light-emitting layer, a second hole blocking layer, a second electron transport layer, and a second electron injection layer was formed.
[0653] Next, on the second electron injection layer in the second light-emitting unit, Mg and Ag were co-deposited at a mixture ratio (mass % ratio) of 10%:90%, to form a semi-transparent upper electrode (cathode) made of an MgAg alloy with a total thickness of 13 nm. Next, compound HT-x was deposited over the entire surface of the upper electrode (cathode) to form a capping layer with a thickness of 65 nm. In this manner, a top-emission organic EL device according to Example 1 was fabricated. The device configuration of Example 1 is schematically shown as follows: Ag / ITO(10) / HT1:HA(10,97%:3%) / HT1(25) / EBL1(5) / BH:BD(19,99%:1%) / ET-11(15) / Ref-1:Yb(7.5,97.5%:2.5%) / HT3:HA( 10,93%:7%) / HT3(40) / EBL1(5) / BH:BD(19,99%:1%) / HBL2(5) / ET2:Liq(31,50%:50%) / Yb(1) / Mg:Ag(13,10%:90%) / HT-x(65)
[0654] [Examples 2 to 5] The organic EL devices of Examples 2 to 5 were fabricated in the same manner as in Example 1, except that the compound ET-11 used in the electron transport layer on the light-emitting layer side of Example 1 was changed to the compounds shown in Table 1, respectively.
[0655] Comparative Example 1 The organic EL device of Comparative Example 1 was prepared in the same manner as in Example 1, except that the compound ET-11 used in the electron transport layer on the light-emitting layer side of Example 1 was changed to a compound shown in Table 1.
[0656] <Evaluation of Organic EL Device> The fabricated organic EL devices were evaluated as follows. The evaluation results are shown in Table 1. In addition, the triplet energy T 1 and affinity Af are also shown in Table 1. In Table 1, |ΔAf| represents |Af(H1)-Af(E1)|.
[0657] (Current efficiency L / J and "L / J / CIEy") The current density of the fabricated organic EL element was 10.00 mA / cm 2The spectral radiance spectrum when a voltage was applied so that the value was 0.05 was measured using a spectroradiometer CS-1000 (manufactured by Konica Minolta, Inc.). From the obtained spectral radiance spectrum, the CIE 1931 chromaticity coordinates (CIEx and CIEy), current efficiency L / J (unit: cd / A), and "L / J / CIEy" were calculated. The value of "L / J / CIEy" was calculated by dividing the value of current efficiency L / J by the value of CIEy. The value of "L / J / CIEy" is sometimes referred to as the blue index (BI). In this evaluation, the value of the blue index (BI) was used as an index of luminous efficiency. Table 1 shows the relative value of "L / J / CIEy". The relative value of "L / J / CIEy" was calculated based on the "L / J / CIEy" of each example of Examples 1 to 5 and Comparative Example 1, and the following mathematical formula (Math X1). The unit of the relative value of "L / J / CIEy" is %. EQE (relative value) = ("L / J / CIEy" of each example / "L / J / CIEy" of Comparative Example 1) × 100 (number X1).
[0658]
[0659] In the organic EL devices according to Examples 1 to 5, an emission-layer-side electron transport layer is disposed in direct contact with the first emission band of the first emission unit, and the triplet energy and affinity of the first electron-transporting band material contained in the emission-layer-side electron transport layer satisfy the above-described mathematical formulas (Mathematical Formula 1) and (Mathematical Formula 2), respectively. This improves the light extraction efficiency of the emission layer in the second emission band of the second emission unit. The organic EL devices according to Examples 1 to 5, which have such emission-layer-side electron transport layers, exhibit improved light extraction efficiency and, as a result, improved external quantum efficiency. In the organic EL device according to Comparative Example 1, the emission-layer-side electron transport layer contains a first electron-transporting band material that is outside the range of the above-described mathematical formula (Mathematical Formula 1). Therefore, the light extraction efficiency was not improved and the external quantum efficiency was lower than in Example 1.
[0660] <Compound evaluation> (triplet energy T 1The compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol / L, and this solution was placed in a quartz cell to prepare a measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this measurement sample was measured at low temperature (77 [K]), and a tangent was drawn to the rising edge of the short wavelength side of this phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent and the horizontal axis was determined. edge Based on [nm], the amount of energy calculated from the following conversion formula (F1) is the triplet energy T 1 The triplet energy T 1 Depending on the measurement conditions, an error of about 0.02 eV may occur. 1 [eV]=1239.85 / λ edge
[0661] The tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows. When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum among the spectral maxima, consider the tangent at each point on the curve toward the long wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope is at its maximum (i.e., the tangent at the inflection point) is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that maximum points with peak intensities of 15% or less of the maximum peak intensity of the spectrum are not included in the shortest wavelength maximum, and the tangent drawn at the point where the slope is closest to the shortest wavelength maximum is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Phosphorescence was measured using an F-4500 spectrofluorometer manufactured by Hitachi High-Technologies Corporation.
[0662] (Energy level of lowest unoccupied molecular orbital (LUMO)) For the chemical structural formulas of the first host material and the first electron transport band material used in Examples 1 to 5 and Comparative Example 1, the energy level of the lowest unoccupied molecular orbital (LUMO) was calculated using a quantum chemistry calculation program (Gaussian 09, Revision E (Gaussian Inc.); calculation method: B3LYP / 6-31G* (meaning that the functional B3LYP for DFT calculation and 6-31G* were used as the basis function)). The calculated LUMO values were replaced with affinity Af values and are shown in Table 1. The units of LUMO and affinity Af are eV.
[0663] (Fluorescence emission maximum peak wavelength λ FL The compound to be measured was dissolved in toluene and 5.0 x 10 -6 The resulting solution was placed in a quartz cell (optical path length 1.0 cm), and the maximum peak wavelength λ of fluorescence emission when excited at 400 nm was measured using a fluorescence spectrum measuring device "Spectrofluorometer FP-8300" (manufactured by JASCO Corporation). FL The maximum peak wavelength λ of the fluorescence emission of Compound BD was measured (unit: nm). FL was 456 nm.
[0664] 1,100...organic EL element, 10, 10A...organic layer, 2, 20...substrate, 3, 30...anode, 4, 40...cathode, 110...first light-emitting unit, 120...second light-emitting unit, 5,510...first light-emitting zone, 50, 511...first light-emitting layer, 520...second light-emitting zone, 521...second light-emitting layer, 6,610...first hole-transporting zone, 61, 611...first electron blocking layer, 62, 612...first hole-transporting layer, 63, 613...first Hole injection layer, 620...second hole transport region, 621...second electron blocking layer, 622...second hole transport layer, 7,710...first electron transport region, 71,712...light-emitting layer side electron transport layer, 720...second electron transport region, 721...second hole blocking layer, 722...second electron transport layer, 723...second electron injection layer, 810...first charge generation region, 73,811...cathode side electron transport layer, 812...second charge generation layer, 90...capping layer.
Claims
1. An organic electroluminescence device, the organic electroluminescence device having 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 including at least a first light-emitting unit and a second light-emitting unit, the first light-emitting unit and the second light-emitting unit being arranged in this order from the anode side toward the cathode side, the first light-emitting unit including a first emission band, the second light-emitting unit including a second emission band, a first electron transport band being disposed between the first emission band and the second emission band, the first electron transport band including one or more layers, one of the one or more layers included in the first electron transport band being an electron transport layer on the light-emitting layer side that is in direct contact with the first emission band, a cathode-side electron transport layer being disposed between the first electron transport band and the second emission band, the electron transport layer on the light-emitting layer side containing a first electron transport band material, the first electron transport band material satisfying the following mathematical formulas (Equation 1) and (Equation 2): Organic electroluminescence device. T 1 T(E1) ≥ 1.90 eV... (Equation 1) Af(E1) ≥ 1.55 eV... (Equation 2) (T 1 (E1) is the triplet energy of the first electron transport band material, and Af(E1) is the affinity of the first electron transport band material.) 2. Charge generation regions are respectively disposed between the light-emitting units of the two or more light-emitting units, and each of the charge generation regions independently includes at least one charge generation layer. The organic electroluminescence device according to claim 1.
3. The organic electroluminescence device according to claim 2, wherein at least one of the charge generation regions includes two or more charge generation layers.
4. A first charge generation region is disposed between the first light-emitting unit and the second light-emitting unit, and the first charge generation region includes at least a first charge generation layer. The organic electroluminescence device according to claim 2 or claim 3.
5. The organic electroluminescence device according to claim 4, wherein the first charge generation layer is the cathode-side electron transport layer.
6. The first electron transport region is disposed between the first light-emitting region and the first charge generation layer. The organic electroluminescence device according to claim 4 or claim 5.
7. The first charge generation region further includes a second charge generation layer, and the second charge generation layer is disposed between the first charge generation layer and the second light-emitting region. The organic electroluminescence device according to any one of claims 4 to 6.
8. The organic electroluminescence device according to claim 7, wherein the first charge generation layer and the second charge generation layer are in direct contact with each other.
9. The organic electroluminescence device according to claim 7 or claim 8, wherein a second hole transport layer is disposed between the second charge generation layer and the second light-emitting region.
10. The organic electroluminescence device according to any one of claims 1 to 9, wherein the cathode-side electron transport layer and the first electron transport region are in direct contact with each other.
11. The first light-emitting region contains a first light-emitting compound, the second light-emitting region 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, and 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. The organic electroluminescence device according to any one of claims 1 to 10.
12. The organic electroluminescence device according to any one of claims 1 to 11, wherein the two or more light-emitting units further include a third light-emitting unit.
13. The organic electroluminescence device according to any one of claims 1 to 12, wherein the first electron transport band material is a compound having a condensed polycyclic skeleton.
14. An organic electroluminescence device having an anode, a cathode, and a first light-emitting band disposed between the anode and the cathode, wherein a first electron transport band is disposed between the first light-emitting band and the cathode, the first electron transport band includes one or more layers, and one of the one or more layers included in the first electron transport band is an electron transport layer on the light-emitting layer side that is in direct contact with the first light-emitting band, a cathode-side electron transport layer is disposed between the first electron transport band and the cathode, the electron transport layer on the light-emitting layer side contains a first electron transport band material, the first electron transport band material is a compound having a condensed polycyclic skeleton, and satisfies the following formulas (Formula 1) and (Formula 2). T 1 (E1) ≥ 1.90 eV... (Formula 1) Af(E1) ≥ 1.55 eV... (Formula 2) (T 1 (E1) is the triplet energy of the first electron transport band material, and Af(E1) is the affinity of the first electron transport band material.) 15. The organic electroluminescence device according to claim 13 or 14, wherein the condensed polycyclic skeleton is a condensed aromatic hydrocarbon ring having 10 to 30 ring-forming carbon atoms or a condensed aromatic heterocyclic ring having 14 to 30 ring-forming atoms.
16. The organic electroluminescence device according to any one of claims 13 to 15, wherein at least one of the condensed polycyclic skeletons is at least one ring selected from the group consisting of a pyrene ring, a fluoranthene ring, a benzofluoranthene ring, a phenanthrene ring, a benzophenanthrene ring, a chrysene ring, a benzochrysene ring, a triphenylene ring, a benzotriphenylene ring, a benzoxanthene ring, and a benzoanthracene ring.
17. The organic electroluminescence device according to any one of claims 13 to 16, wherein the first electron transport band material is a compound represented by the following formula (E1). (In the formula (E1), R 101 to 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, a group represented by -Si(R 901 )(R 902 )(R 903 ), a group represented by -O-(R 904 ), a group represented by -S-(R 905 ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by -C(=O)R 801 , a group represented by -COOR 802 , 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 at least one of R 101 to R 110 is a group represented by the formula (E11), and when there are a plurality of groups represented by the formula (E11), 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 there are two or more, two or more Ls 101 are the same as or different from each other, and Ar 101 When there are two or more, two or more Ars 101 are the same as or different from each other. The * 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. When there are a plurality of Rs 901 , the plurality of Rs 901 are the same as or different from each other. When there are a plurality of Rs 902 , the plurality of Rs 902 are the same as or different from each other. When there are a plurality of Rs 903 , the plurality of Rs 903 are the same as or different from each other. When there are a plurality of Rs 904 , the plurality of Rs 904 are the same as or different from each other. When there are a plurality of Rs 905 , the plurality of Rs 905 are the same as or different from each other. When there are a plurality of Rs 801 , the plurality of Rs 801 are the same as or different from each other. When there are a plurality of Rs 802 , the plurality of Rs 802 are the same as or different from each other.) 18. The organic electroluminescence device according to any one of claims 13 to 16, wherein the first electron transport band material is a compound represented by the following formula (E2). (In the formula (E2), R 201 ~R 212 Among them, one or more sets of two or more adjacent ones are combined with each other to form a substituted or unsubstituted monocyclic ring, or are combined 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 ~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 ), a group represented by -O-(R 904 ), a group represented by -S-(R 905 ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by -C(=O)R 801 , a group represented by -COOR 802 , 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 at least one of R 201 ~R 212 that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 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, and when two or more L 201 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, and when two or more Ar 201 are present, the two or more Ar 201 are the same as or different from each other. 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 to R 212 form the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted condensed ring, * 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. When a plurality of R 901 are present, the plurality of R 901 are the same as or different from each other. When a plurality of R 902 are present, the plurality of R 902 are the same as or different from each other. When a plurality of R 903 are present, the plurality of R 903 are the same as or different from each other. When a plurality of R 904 When there are a plurality of them, the plurality of Rs 904 are the same as or different from each other, and when there are a plurality of Rs 905 When there are a plurality of them, the plurality of Rs 905 are the same as or different from each other, and when there are a plurality of Rs 801 When there are a plurality of them, the plurality of Rs 801 are the same as or different from each other, and when there are a plurality of Rs 802 When there are a plurality of them, the plurality of Rs 802 are the same as or different from each other.) 19. The organic electroluminescence device according to any one of claims 13 to 16, wherein the first electron transport band material is a compound represented by the following formula (E3). (In the formula (E3), 307 one of R 312 and R 307 represents a single bond with *1, and the other of R 312 and R 301 represents a single bond with *2, 306 R 308 to R 311 , R 322 to R 325 are each independently 901 a hydrogen atom, 902 a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, 903 a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, 904 a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, 905 a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, 906 a group represented by -Si(R 907 )(R 321 ), 31 a group represented by -O-(R 31 ), 32 is, independently of one another, 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 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, 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; 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; when there are a plurality of R 905 , the plurality of R 905 are the same as or different from each other; when there are a plurality of R 906 , the plurality of R 906 are the same as or different from each other, and R 907 when there are a plurality of them, the plurality of Rs 907 are the same as or different from each other.) 20. The organic electroluminescence device according to any one of claims 13 to 16, wherein the first electron transport band material is a compound represented by the following formula (E4). (In the formula (E4), 2 X 42 is N or C-(L 2 )m 42 -(Ar 21 )m 4 X 44 is N or C-(L 4 )m 44 -(Ar 41 )m 5 X 45 is N or C-(L 5 )m 45 -(Ar 51 )m 6 X 46 is N or C-(L 6 )m 46 -(Ar 61 )m 2 X 4 X 5 and X 6 Among them, at least one is a nitrogen atom, 41 L 46 to L 1 m 1 is 0, 1, 2 or 3. When m 41 is 0, -(L 0 ) 2 m 2 is 0, 1, 2 or 3. When m 42 is 0, -(L 0 ) 3 m 3 is 0, 1, 2 or 3. When m 43 is 0, -(L 0 ) 4 m 4 is 0, 1, 2 or 3. When m 44 ) 0 - represents a single bond, and m 5 is 0, 1, 2, or 3. When m 5 is 0, -(L 45 ) 0 - represents a single bond, and m 6 is 0, 1, 2, or 3. When m 6 is 0, -(L 46 ) 0 - represents a single bond, and m 1 is 2 or more. When 2 or more L 41 are the same as or different from each other, and m 2 is 2 or more. When 2 or more L 42 are the same as or different from each other, and m 3 is 2 or more. When 2 or more L 43 are the same as or different from each other, and m 4 is 2 or more. When 2 or more L 44 are the same as or different from each other, and m 5 is 2 or more. When 2 or more L 45 are the same as or different from each other, and m 6 is 2 or more. When 2 or more L 46 are the same as or different from each other, and 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 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 substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R 920 ), a group represented by —COOR 921 ), 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 at least one of Ar 41 to 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, and when m 11 is 2 or more, two or more Ar 41 are the same as or different from each other, and when m 21 is 2 or more, two or more Ar 42 are the same as or different from each other, and when m 31 is 2 or more, two or more Ar 43 are the same as or different from each other, and when m 41 is 2 or more, two or more Ar 44 are the same as or different from each other, and when m 51 is 2 or more, two or more Ar 45 are the same as or different from each other, and when m 61 is 2 or more, two or more Ar 46 are the same as or different from each other. (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 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 911 when a plurality of Rs exist, the plurality of Rs 911 are the same as or different from one another, and R 912 when a plurality of Rs exist, the plurality of Rs 912 are the same as or different from one another, and R 913 when a plurality of Rs exist, the plurality of Rs 913 are the same as or different from one another, and R 914 when a plurality of Rs exist, the plurality of Rs 914 are the same as or different from one another, and R 915 when a plurality of Rs exist, the plurality of Rs 915 are the same as or different from one another, and R 916 when a plurality of Rs exist, the plurality of Rs 916 are the same as or different from one another, and R 917 when a plurality of Rs exist, the plurality of Rs 917 are the same as or different from one another, and R 918 when a plurality of Rs exist, the plurality of Rs 918 are the same as or different from one another, and R 919 when a plurality of Rs exist, the plurality of Rs 919 are the same as or different from one another, and R 920 when a plurality of Rs exist, the plurality of Rs 920 are the same as or different from one another, and R 921 when a plurality of Rs exist, the plurality of Rs 921 are the same as or different from one another.) 21. The organic electroluminescence device according to claim 20, wherein the first electron transport band material is a compound represented by the following formula (E41). (In the formula (E41), L 41 , L 43 , and L 45 are each synonymous with L 41 , L 43 , and L 45 in the formula (E4), m 1 , m 3 , and m 5 are each synonymous with m 1 , m 3 , and m 5 in the formula (E4), and one of R A and R B 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 "substituted or unsubstituted" in the substituent S as R A or R B , when it is "substituted", it has one or more substituents T, and R 401 to 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 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 there are two or more substituents R, 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 being a single bond with *3 A and R B among two or more adjacent ones do not bond to each other, X 6 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, Ar 41 and Ar 45 in the case of "substituted or unsubstituted" in the substituent X, in the case of "substituted", it has one or more substituents U, Ar not being a substituent X 41 and Ar 45 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 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 heterocyclic group represented by the following formula (E412). When there are two or more substituents X, the two or more substituents X are the same as or different from each other. When there are two or more substituents U, 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" for the substituent T, Ar 41 and Ar 45 In the case of "substituted or unsubstituted" for the substituent U, and Ar 46 The substituent V, as each, is 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 ), 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, and is selected from the group consisting of; when there are two or more substituents T, the two or more substituents T are the same as or different from each other.) X 41 is N(R 429 ), an oxygen atom, or a sulfur atom. One of R 421 to R 429 represents a single bond with L 41 or L 45 ; one or more sets of two or more adjacent ones among R 421 to R 429 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, do not represent a single bond with L 41 or L 45 , do not form the substituted or unsubstituted monocyclic ring, and do not form the substituted or unsubstituted condensed ring, and R 421 to R 429 is, independently of each other, 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 ), 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 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. One of R 431 to R 437 represents a single bond with L 41 or L 45 . One or more sets of two or more adjacent ones among R 431 to R 437 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other, and do not represent a single bond with L 41 or L 45 , do not form the substituted or unsubstituted monocyclic ring, and do not form the substituted or unsubstituted condensed ring. R 431 to R 437 are, independently of each other, 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 ), 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms and not containing a nitrogen atom, which is selected from the group consisting of.) (In the above formulas (E41), (E411) and (E412), R 911 to 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 when there are a plurality of R 911 , the plurality of R 911 are the same as or different from each other, and when there are a plurality of R 912 , the plurality of R 912 are the same as or different from each other, and when there are a plurality of R 913 , the plurality of R 913 are the same as or different from each other, and when there are a plurality of R 914 , the plurality of R 914 are the same as or different from each other, and when there are a plurality of R 915 , the plurality of R 915 are the same as or different from each other, and when there are a plurality of R 916 , the plurality of R 916 are the same as or different from each other, and when there are a plurality of R 917 , the plurality of R 917 are the same as or different from each other, and when there are a plurality of R 918 , the plurality of R 918 are the same as or different from each other, and when there are a plurality of R 919 When there are a plurality of them, the plurality of Rs 919 are the same as or different from each other.) 22. The organic electroluminescence device according to claim 20, wherein the first electron transport band material is a compound represented by the following formula (E42). (In the formula (E42), X 2 , X 4 , X 6 , L 41 , L 43 , L 45 , Ar 41 and Ar 45 are respectively synonymous with X 2 , X 4 , X 6 , L 41 , L 43 , L 45 , Ar 41 and Ar 45 in the formula (E4), and m 1 , m 3 , m 31 and m 5 are respectively synonymous with m 1 , m 3 , m 31 and m 5 in the formula (E4). Among R 4001 to R 4008 , one or more sets of two or more adjacent ones are combined with each other to form a substituted or unsubstituted monocyclic ring, or are combined with each other to form a substituted or unsubstituted condensed ring, or are not combined with each other. R 4009 , and R 4001 to R 4008 that 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 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, 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 ), 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 R 4009 , and 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 4001 ~R 4008 at least one of is a single bond with *4, and *4 indicates the bonding position with the carbazole ring in the formula (E42). However, R 4001 ~R 4008 If one or more of the groups consisting of two or more adjacent ones among form the above-mentioned substituted or unsubstituted monocyclic ring or the above-mentioned 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).) 23. The organic electroluminescence device according to claim 20, wherein the first electron transport band material is a compound represented by the following formula (E43). (In the formula (E43), X 2 , X 4 , X 6 , L 41 , L 43 , L 45 , Ar 41 and Ar 45 are respectively synonymous with X 2 , X 4 , X 6 , L 41 , L 43 , L 45 , Ar 41 and Ar 45 in the formula (E4), and m 1 , m 3 , m 31 and m 5 are respectively synonymous with m 1 , m 3 , m 31 and m 5 in the formula (E4). Among R 5001 to R 5008 , one or more sets of two or more adjacent ones are combined with each other to form a substituted or unsubstituted monocyclic ring, or combined with each other to form a substituted or unsubstituted condensed ring, or not combined with each other, not forming the substituted or unsubstituted monocyclic ring, and not forming the substituted or unsubstituted condensed ring. R 5001 to 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, 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 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 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 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 of the groups consisting of two or more adjacent ones among 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 mother 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).) 24. The organic electroluminescence device according to claim 20, wherein the first electron transport band material is a compound represented by the following formula (E44). (In the formula (E44), X 2 , X 4 , X 6 , L 41 , L 43 , L 45 , Ar 41 and Ar 45 are each synonymous with X 2 , X 4 , X 6 , L 41 , L 43 , L 45 , Ar 41 and Ar 45 in the formula (E4), and m 1 , m 3 , m 31 and m 5 are each synonymous with m 1 , m 3 , m 31 and m 5 in the formula (E4). R 6009 and R 6010 form a group that either combines with each other to form a substituted or unsubstituted monocyclic ring, combines with each other to form a substituted or unsubstituted condensed ring, or does not combine with each other. One or more groups of two or more adjacent ones among R 6001 to R 6008 either 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. R 6001 to R 6010 that 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 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 is a single bond with *6, and *6 indicates the bonding position with the fluorene ring in the above formula (E44). However, when one or more of the sets 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 above formula (E44) indicates the bonding position with the parent skeleton of the formed ring structure.) (In the above 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 above formula (E4).) 25. The organic electroluminescence device according to any one of claims 13 to 16, wherein the first electron transport band material is a compound represented by the following formula (E5). (In the formula (E5), R 501 ~R 508 Among them, one or more of the sets consisting of two or more adjacent ones are combined with each other to form a substituted or unsubstituted monocyclic ring, or combined with each other to form a substituted or unsubstituted condensed ring, or not combined with each other, and do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring. R 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, a group represented by -O-(R 904 ), a group represented by -S-(R 905 ), a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a carboxy group, a group represented by -N(R 905N )(R 906N ), 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. 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 L 501 are the same as or different from each other. Two or more HAr 501 are identical to or different from each other, and * in the formula (E51) indicates the bonding position with the phenanthroline ring in the formula (E5). However, R 501 ~R 508 If 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, * in the formula (E51) indicates the bonding position with the mother 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 R 904 , the plurality of R 904 are identical to or different from each other. When there are a plurality of R 905 , the plurality of R 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 R 905N , the plurality of R 905N are identical to or different from each other. When there are a plurality of R 906N , the plurality of R 906N are identical to or different from each other.) 26. R 501 ~R 508 At 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 (E511) to (E515). The organic electroluminescence element according to claim 25. (In the formula (E511), R 511 , R 512 , R 513 , R 514 and R 515 Any one of them represents a single bond with L 501 . 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 them represents a single bond with L 501 . In the formula (E514), R 523 , R 524 , R 525 and R 526 Any one of them represents a single bond with L 501 . In the formula (E515), R 527 , R 528 , R 529 and R 530 Any one of them represents a single bond with L 501 . One or more sets of two or more adjacent ones among R 511 ~R 530 either 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, and do not represent a single bond with L 501 , do not form the substituted or unsubstituted monocyclic ring, and do not form the substituted or unsubstituted condensed ring. R 511 ~R 530 is, independently of one another, 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, a group represented by -O-(R 904 ), a group represented by -S-(R 905 ), 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 a group represented by -N(R 905N )(R 906N ), where 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 the bonding position.) 27. R 501 ~R 508 At 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 of the following formulas (E516) to (E526). The organic electroluminescence element according to claim 25. (In the formulas (E516) to (E526), R E Any one of them represents a single bond with L 501 , and one or more of the sets consisting of two or more adjacent ones among the plurality of R E are combined with each other to form a substituted or unsubstituted monocyclic ring, or are combined with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other, and do not represent a single bond with L 501 , do not form the substituted or unsubstituted monocyclic ring, and do not form the substituted or unsubstituted condensed ring. Each R E is 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, a group represented by -O-(R 904 ), a group represented by -S-(R 905 ), 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 a group represented by -N(R 905N )(R 906N ), and R 904 , R 905 , R 905N and R 906N are respectively synonymous with R 904 , R 905 , R 905N and R 906N in the formula (E5), and the plurality of R E are the same as or different from each other, and * represents the bonding position.) 28. The organic electroluminescence device according to any one of claims 13 to 16, wherein the first electron transport band material is a compound represented by the following formula (E61) or (E62). (In the formulas (E61) and (E62), Cz is independently any of the carbazolyl groups or indolyl groups represented by any of the following formulas (E63), (E64), (E65), (E66), (E67) and (E68), L 6 is 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 a plurality of Ls exist, the plurality of Ls 6 are the same as or different from each other. When a plurality of Cz exist, the plurality of Cz are the same as or different from each other. FA is independently a substituted or unsubstituted condensed ring group having 6 to 50 ring-forming carbon atoms, provided that FA is not an unsubstituted carbazolyl group.) (In the formulas (E63), (E64), (E65), (E66), (E67) and (E68), Z 6 is independently 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 604 and R 605 is, independently of each other, 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 of each other, 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; and a plurality of R 6 in which 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, and do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring, R 6 is, independently of each other, 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, a group represented by -O-(R 904 ), a group represented by -S-(R 905 ), 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; when a plurality of R 601 are present, the plurality of R 601 are the same as or different from each other; when a plurality of R 602 are present, the plurality of R 602 are the same as or different from each other; when a plurality of R 603 are present, the plurality of R 603 are the same as or different from each other; when a plurality of R 604 are present, the plurality of R 604 are the same as or different from each other; when a plurality of R 605 When there are a plurality of them, the plurality of Rs 605 are the same as or different from each other, and the plurality of Rs 6 are the same as 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, and when there are a plurality of Rs 904 the plurality of Rs 904 are the same as or different from each other, and when there are a plurality of Rs 905 the plurality of Rs 905 are the same as or different from each other.) 29. The group represented by the formula (E63) is a group represented by any one of the formulas selected from the group consisting of the following formulas (E631), (E632), (E633), and (E634). The organic electroluminescence element according to claim 28. (In the formulas (E631), (E632), (E633), and (E634), R 6 and a are respectively synonymous with R 6 and a in the formula (E63), bx is 4, by is 3, and R 61 to R 68 are each independently synonymous with R 6 in the formula (E63), and a plurality of R 6 are the same as or different from each other, and * represents a bonding position.) 30. The group represented by the formula (E65) is a group represented by any one of the formulas selected from the group consisting of the following formulas (E651), (E652), (E653) and (E654). The organic electroluminescence device according to claim 28. (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, and R 61 to R 68 are each independently synonymous with R 6 in the formula (E65), and a plurality of R 6 are the same as or different from each other, and * represents a bonding position.) 31. The organic electroluminescence device according to any one of claims 13 to 16, wherein the first electron transporting region material is a compound represented by the following formula (E7): (In the formula (E7), R 701 ~R 710 each independently represents 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 carbon atoms, -Si(R 901 ) (R 902 ) (R 903 ), a group represented by —O—(R 904 ) group, -S-(R 905 a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R 801 A group represented by the formula: 802 a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (E71), wherein R 701 ~R 710 is a group represented by the formula (E71), and when a plurality of groups represented by the formula (E71) are present, the plurality of groups represented by the formula (E71) are the same or different from each other, L 701 represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, 701 is 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, mx7 is 0, 1, 2, 3, 4, or 5, provided that when mx7 is 0, -(L 701 ) 0 - is a single bond, L 701 If there are two or more Ls 701 they are the same as or different from each other, and Ar 701 If there are two or more Ars 701 they 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, and when there are a plurality of Rs 901 the plurality of Rs 901 are the same as or different from each other, and when there are a plurality of Rs 902 the plurality of Rs 902 are the same as or different from each other, and when there are a plurality of Rs 903 the plurality of Rs 903 are the same as or different from each other, and when there are a plurality of Rs 904 the plurality of Rs 904 are the same as or different from each other, and when there are a plurality of Rs 905 the plurality of Rs 905 are the same as or different from each other, and when there are a plurality of Rs 801 the plurality of Rs 801 are the same as or different from each other, and when there are a plurality of Rs 802 the plurality of Rs 802 are the same as or different from each other.) 32. The organic electroluminescence device according to any one of claims 1 to 31, wherein the first electron transport band material satisfies the following mathematical formula (Formula 21). Af(E1) ≧ 1.65 eV... (Formula 21) (Af(E1) is the affinity of the first electron transport band material.) 33. The first light-emitting band includes a first light-emitting layer. The first light-emitting layer contains a first host material. The affinity Af(H1) of the first host material and the affinity Af(E1) of the first electron transport band material satisfy the relationship of the following mathematical formula (Formula 3). The first host material and the first electron transport band material are the same as or different from each other. The organic electroluminescence device according to any one of claims 1 to 32. |Af(H1) - Af(E1)| ≦ 0.20 eV... (Formula 3) 34. An electronic device equipped with the organic electroluminescence device according to any one of claims 1 to 33.
Citation Information
Patent Citations
Organic electroluminescent element
JP2013543250A
Organic electroluminescent element
JP2014503979A
Organic light-emitting element
JP2024109027A
Organic electroluminescent element
WO2010134350A1
Organic electroluminescent element
WO2010143434A1