Organic electroluminescence element and electronic device
Patent Information
- Application Number
- PCT/JP2026/011280
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2025-08-05
- Filing Date
- 2026-03-23
- Publication Date
- 2026-10-01
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Figure JP2026011280_01102026_PF_FP_ABST
Abstract
Description
Organic electroluminescent elements and electronic devices
[0001] This invention relates to organic electroluminescent elements and electronic devices.
[0002] Organic electroluminescent elements (hereinafter sometimes referred to as "organic EL elements") are used in full-color displays for mobile phones and televisions. When a voltage is applied to an organic EL element, holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. In the light-emitting layer, the injected holes and electrons recombine to form excitons. At this time, according to the statistical laws of electron spin, singlet excitons are generated at a rate of 25%, and triplet excitons are generated at a rate of 75%. In order to improve the performance of organic EL elements, for example, Patent Documents 1 and 2 have examined various compounds used in organic EL elements. Examples of performance characteristics of organic EL elements include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan.
[0003] International Publication No. 2021 / 210582, U.S. Patent Application Publication No. 2024 / 0244969, Specification
[0004] The object of the present invention is to provide an organic electroluminescent element that emits light with high efficiency and long lifespan, and to provide an electronic device equipped with the organic electroluminescent element.
[0005] According to one aspect of the present invention, an organic electroluminescent element comprises: an anode; a cathode; and a light-emitting band disposed between the anode and the cathode, wherein the anode, the light-emitting band, and the cathode are arranged in this order, the light-emitting band includes a first light-emitting layer and a second light-emitting layer, the first light-emitting layer contains a first host material and a first dopant material, the second light-emitting layer contains a second host material and a second dopant material, the first host material and the second host material are different from each other, the first dopant material is a light-emitting compound with a maximum peak wavelength of 500 nm or less, the second dopant material is a light-emitting compound with a maximum peak wavelength of 500 nm or less, the first dopant material and the second dopant material are different from each other, and the triplet energy T of the first host material 1 (H1) and the triplet energy T of the second host material 1 An organic electroluminescent element is provided in which (H2) and satisfy the relationship shown in the following formula (Equation 1), and the first dopant material HOMO(D1) and the second dopant material HOMO(D2) satisfy the relationship shown in the following formula (Equation 2). 1 (H1)>T 1 (H2) ... (Equation 1) HOMO(D1) - HOMO(D2) > 0.25 eV ... (Equation 2)
[0006] According to one aspect of the present invention, an electronic device equipped with an organic electroluminescent element according to one aspect of the present invention is provided.
[0007] According to one aspect of the present invention, it is possible to provide an organic electroluminescent element that emits light with high efficiency and long lifespan, and to provide an electronic device equipped with the organic electroluminescent element.
[0008] This figure shows a schematic configuration of a first example of an organic EL element according to the first embodiment. This figure shows a schematic configuration of a second example of an organic EL element according to the first embodiment.
[0009] [Definition] In this specification, the term "hydrogen atom" includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.
[0010] In this specification, in chemical structural formulas, any bondable positions where symbols such as "R" or "D" representing a deuterium atom are not explicitly indicated shall be assumed to be bonded to hydrogen atoms, i.e., light hydrogen atoms, deuterium atoms, or tritium atoms.
[0011] In this specification, the ring-forming carbon number refers to the number of carbon atoms among the atoms constituting the ring itself in a compound with a structure in which atoms are bonded in a ring (e.g., monocyclic compounds, fused ring compounds, crosslinked compounds, carbocyclic compounds, and heterocyclic compounds). If the ring is substituted by a substituent, the carbon atoms in the substituent are not included in the ring-forming carbon number. The same applies to "ring-forming carbon number" as described below unless otherwise specified. For example, a benzene ring has 6 ring-forming carbon atoms, a naphthalene ring has 10 ring-forming carbon atoms, a pyridine ring has 5 ring-forming carbon atoms, and a furan ring has 4 ring-forming carbon atoms. Also, for example, a 9,9-diphenylfluorenyl group has 13 ring-forming carbon atoms, and a 9,9'-spirobifluorenyl group has 25 ring-forming carbon atoms. Furthermore, if a benzene ring is substituted with an alkyl group as a substituent, the number of carbon atoms in the alkyl group is not included in the ring-forming carbon number of the benzene ring. Therefore, the ring-forming carbon number of a benzene ring substituted with an alkyl group is 6. Furthermore, if an alkyl group is substituted as a substituent on the naphthalene ring, the number of carbon atoms in that alkyl group is not included in the number of ring-forming carbon atoms of the naphthalene ring. Therefore, the number of ring-forming carbon atoms in a naphthalene ring substituted with an alkyl group is 10.
[0012] In this specification, the number of ring-forming atoms refers to the number of atoms that constitute the ring itself in compounds with a ring-bonded structure (e.g., monocyclic compounds, fused rings, and ring assemblies) (e.g., monocyclic compounds, fused ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of ring-forming atoms) and atoms included in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. The same applies to "number of ring-forming atoms" as described below unless otherwise specified. For example, the number of ring-forming atoms in a pyridine ring is 6, the number of ring-forming atoms in a quinazoline ring is 10, and the number of ring-forming atoms in a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring, or the number of atoms constituting a substituent, are not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms in a pyridine ring to which hydrogen atoms or substituents are bonded is 6. Furthermore, for example, hydrogen atoms bonded to the carbon atom of the quinazoline ring, or atoms constituting substituents, are not included in the number of ring-forming atoms of the quinazoline ring. Therefore, the number of ring-forming atoms of a quinazoline ring to which hydrogen atoms or substituents are bonded is 10.
[0013] In this specification, the expression "substituted or unsubstituted ZZ group having XX to YY carbon atoms" means that "XX to YY carbon atoms" refers to the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of substituents when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.
[0014] In this specification, the expression "ZZ group with substituted or unsubstituted atoms number XX to YY" means that "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 substituent atoms when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.
[0015] In this specification, an unsubstituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group," and a substituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is a "substituted ZZ group." In this specification, "unsubstituted" in the case of "substituted or unsubstituted ZZ group" means that the hydrogen atoms in the ZZ group are not replaced by substituents. The hydrogen atoms in an "unsubstituted ZZ group" are light hydrogen atoms, deuterium atoms, or tritium atoms. Also, in this specification, "substituted" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by substituents. Similarly, "substituted" in the case of "BB group substituted with AA group" means that one or more hydrogen atoms in the BB group are replaced by AA group.
[0016] "Substituents described herein" Hereinafter, substituents described herein will be explained.
[0017] The number of ring-forming carbon atoms in the "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified herein. The number of ring-forming atoms in the "unsubstituted heterocyclic group" described herein is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkyl group" described herein is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkenyl group" described herein is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkynyl group" described herein is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "unsubstituted cycloalkyl group" described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "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-forming atoms in the "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 in the "unsubstituted alkylene group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein.
[0018] ・"Substitutable or unsubstituted aryl groups" Specific examples of "substituted or unsubstituted aryl groups" as described herein (Specific Example Group G1) include the following unsubstituted aryl groups (Specific Example Group G1A) and substituted aryl groups (Specific Example Group G1B). (Here, "unsubstituted aryl group" refers to the case where "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and "substituted aryl group" refers to the case where "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, when simply referred to as "aryl group," it includes both "unsubstituted aryl groups" and "substituted aryl groups." A "substituted aryl group" means a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced by substituents. Examples of "substituted aryl groups" include the group in which one or more hydrogen atoms of an "unsubstituted aryl group" in Specific Example Group G1A below are replaced by substituents, and the example of a substituted aryl group in Specific Example Group G1B below. The examples of "unsubstituted aryl groups" and "substituted aryl groups" listed herein are merely examples. The "substituted aryl groups" described herein also include groups in which the hydrogen atoms bonded to the carbon atom of the aryl group itself in the "substituted aryl groups" of specific examples group G1B below are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted aryl groups" of specific examples group G1B below are further replaced by substituents.
[0019] - Unsubstituted aryl groups (specific examples group G1A): Phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, benzoantryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, crisenyl group, benzocrisenyl group, triphenylenyl group, benzotriphenylenyl group, tetracerenyl group, pentaceryl group, fluorenyl group, 9,9'-spirobifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, fluoranthenyl group, benzofluoranthenyl group, perilenyl group, and monovalent aryl groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).
[0020]
[0021]
[0022] Substitutive aryl groups (specific examples 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, A naphthylphenyl group, and a monovalent group derived from the ring structure represented by the general formulas (TEMP-1) to (TEMP-15) in which one or more hydrogen atoms are replaced by substituents.
[0023] - "Substituted or unsubstituted heterocyclic groups" The "heterocyclic groups" described herein are cyclic groups containing at least one heteroatom in the ring-forming atoms. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron. The "heterocyclic groups" described herein are monocyclic groups or fused ring groups. The "heterocyclic groups" described herein are aromatic heterocyclic groups or non-aromatic heterocyclic groups. Specific examples of "substituted or unsubstituted heterocyclic groups" described herein (Specific Examples Group G2) include the following unsubstituted heterocyclic groups (Specific Examples Group G2A) and substituted heterocyclic groups (Specific Examples Group G2B). (Here, "unsubstituted heterocyclic group" refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group," and "substituted heterocyclic group" refers to the case where "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group.") In this specification, the term "heterocyclic group" alone includes both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups." A "substituted heterocyclic group" means a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by substituents. Specific examples of "substituted heterocyclic groups" include the groups in the following example group G2A in which hydrogen atoms of an "unsubstituted heterocyclic group" are replaced, and the examples of substituted heterocyclic groups in the following example group G2B. Furthermore, the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic groups" described herein also include groups in which the hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself in the "substituted heterocyclic groups" of specific examples group G2B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted heterocyclic groups" of specific examples group G2B are further replaced by substituents.
[0024] The specific examples group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (Specific Examples Group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (Specific Examples Group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (Specific Examples Group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (Specific Examples Group G2A4).
[0025] Specific examples group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (Specific Examples Group G2B1), substituted heterocyclic groups containing an oxygen atom (Specific Examples Group G2B2), substituted heterocyclic groups containing a sulfur atom (Specific Examples Group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (Specific Examples Group G2B4).
[0026] ・Unsubstituted heterocyclic groups containing nitrogen atoms (specific examples group G2A1): Pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyridyl group, pyridadinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, indolyl group, isoindolyl group, indolidinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, indazolyl group, phenanthrolinyl group, phenanthridineyl group, acridinyl group, phenadinyl group, carbazolyl group, Benzocarbazolyl group, morpholino group, phenoxazinyl group, phenothiazinyl group, azacarbazolyl group, and diazacarbazolyl group.
[0027] - Unsubstituted heterocyclic groups containing an oxygen atom (specific examples group G2A2): furyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzoisoxazolyl group, phenoxazinyl group, morpholino group, dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, azanaphtobenzofuranyl group, and diazanaphtobenzofuranyl group.
[0028] • Unsubstituted heterocyclic groups containing a sulfur atom (Specific Example Group G2A3): thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, benzothiophenyl group (benzothienyl group), isobenzothiophenyl group (isobenzothienyl group), dibenzothiophenyl group (dibenzothienyl group), naphthobenzothiophenyl group (naphthobenzothienyl group), benzothiazolyl group, benzoisothiazolyl group, phenothiazinyl group, dinaphthothiophenyl group (dinaphthothienyl group), azadibenzothiophenyl group (azadibenzothienyl group), diazadibenzothiophenyl group (diazadibenzothienyl group), azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).
[0029] • Monovalent heterocyclic groups derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (Specific Example Group G2A4):
[0030]
[0031]
[0032] In the general formulas (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH 2 . Provided that at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH. In the general formulas (TEMP-16) to (TEMP-33), when at least one of X A and Y A is NH or CH 2 , the monovalent heterocyclic group derived from the ring structure represented by general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from said NH or CH 2 .
[0033] - Substitutive heterocyclic groups containing a nitrogen atom (specific examples group G2B1): (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazole-9-yl group, phenylcarbazole-9-yl group, methylbenzimidazolyl group, ethylbenzimidazolyl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenylquinazolinyl group, and biphenylylquinazolinyl group.
[0034] - Heterocyclic groups with oxygen atoms substituted (specific examples group G2B2): Phenyldibenzofuranyl group, methyldibenzofuranyl group, t-butyldibenzofuranyl group, and monovalent residues of spiro[9H-xanthene-9,9'-[9H]fluorene].
[0035] - Substitutive heterocyclic groups containing a sulfur atom (specific examples group G2B3): Phenyldibenzothiophenyl group, methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, and monovalent residues of spiro[9H-thioxanthene-9,9'-[9H]fluorene].
[0036] - Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific examples group G2B4):
[0037] The aforementioned "one or more hydrogen atoms of a monovalent heterocyclic group" refers to hydrogen atoms bonded to the ring-forming carbon atoms of the monovalent heterocyclic group, X A and Y A A hydrogen atom bonded to a nitrogen atom when at least one of them is NH, and X A and Y A One of them is CH 2 This refers to one or more hydrogen atoms selected from the hydrogen atoms of the methylene group in that case.
[0038] ・"Substitutable or unsubstituted alkyl groups" Specific examples of "substituted or unsubstituted alkyl groups" as described herein (Specific Examples Group G3) include the following unsubstituted alkyl groups (Specific Examples Group G3A) and substituted alkyl groups (Specific Examples Group G3B). (Here, "unsubstituted alkyl group" refers to the case where "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and "substituted alkyl group" refers to the case where "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereafter, when simply referred to as "alkyl group," it includes both "unsubstituted alkyl groups" and "substituted alkyl groups." "Substitutable alkyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced by substituents. Specific examples of "substituted alkyl groups" include the group in which one or more hydrogen atoms in the following "unsubstituted alkyl group" (Specific Examples Group G3A) are replaced by substituents, and examples of substituted alkyl groups (Specific Examples Group G3B). In this specification, the alkyl group in "unsubstituted alkyl group" means a chain-like alkyl group. Therefore, "unsubstituted alkyl groups" include both linear and branched "unsubstituted alkyl groups." The examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed here are merely examples; the "substituted alkyl groups" described herein also include groups in which the hydrogen atoms of the alkyl group itself are further replaced by substituents, as well as groups in which the hydrogen atoms of the substituents are further replaced by substituents.
[0039] Unsubstituted alkyl groups (specific examples group G3A): methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group.
[0040] Substituting alkyl groups (specific examples group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group, and trifluoromethyl group.
[0041] - "Substitutable or unsubstituted alkenyl groups" Specific examples of "substituted or unsubstituted alkenyl groups" as described herein (Specific Examples Group G4) include the following unsubstituted alkenyl groups (Specific Examples Group G4A) and substituted alkenyl groups (Specific Examples Group G4B). (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply includes both "unsubstituted alkenyl groups" and "substituted alkenyl groups." A "substituted alkenyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are replaced by substituents. Specific examples of "substituted alkenyl groups" include groups in which the "unsubstituted alkenyl groups" (specific example group G4A) have substituents, and examples of substituted alkenyl groups (specific example group G4B). Note that the examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed here are merely examples, and the "substituted alkenyl groups" described herein also include groups in which the hydrogen atoms of the alkenyl group itself in the "substituted alkenyl groups" of specific example group G4B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted alkenyl groups" of specific example group G4B are further replaced by substituents.
[0042] - Unsubstituted alkenyl groups (specific examples group G4A): vinyl group, allyl group, 1-butenyl group, 2-butenyl group, and 3-butenyl group.
[0043] Substitutable alkenyl groups (specific examples group G4B): 1,3-butanedienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl group.
[0044] ・"Substituted or unsubstituted alkynyl groups" Specific examples of "substituted or unsubstituted alkynyl groups" as described herein (Specific Examples Group G5) include the following unsubstituted alkynyl groups (Specific Examples Group G5A), etc. (Here, an unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl groups" is an "unsubstituted alkynyl group.") Hereafter, when simply referred to as "alkynyl group," it includes both "unsubstituted alkynyl groups" and "substituted alkynyl groups." A "substituted alkynyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced by substituents. Specific examples of "substituted alkynyl groups" include the following groups in which one or more hydrogen atoms in an "unsubstituted alkynyl group" (Specific Examples Group G5A) are replaced by substituents, etc.
[0045] • Unsubstituted alkynyl groups (specific examples group G5A): Ethynyl group
[0046] ・"Substituted or unsubstituted cycloalkyl groups" Specific examples of "substituted or unsubstituted cycloalkyl groups" as described herein (Specific Examples Group G6) include the following unsubstituted cycloalkyl groups (Specific Examples Group G6A) and substituted cycloalkyl groups (Specific Examples Group G6B). (Here, "unsubstituted cycloalkyl group" refers to the case where "substituted or unsubstituted cycloalkyl group" is "unsubstituted cycloalkyl group," and "substituted cycloalkyl group" refers to the case where "substituted or unsubstituted cycloalkyl group" is "substituted cycloalkyl group.") In this specification, "cycloalkyl group" simply includes both "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups." "Substituted cycloalkyl group" means a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced by substituents. Specific examples of "substituted cycloalkyl groups" include the following groups in which one or more hydrogen atoms in the "unsubstituted cycloalkyl group" (Specific Examples Group G6A) are replaced by substituents, and examples of substituted cycloalkyl groups (Specific Examples Group G6B). The examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed herein are merely examples. The "substituted cycloalkyl groups" described herein also include groups in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself are replaced by substituents, as well as groups in which the hydrogen atoms of the substituents in the "substituted cycloalkyl groups" of specific examples group G6B are further replaced by substituents.
[0047] Unsubstituted cycloalkyl groups (specific examples group G6A): cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.
[0048] Substitutive cycloalkyl groups (specific examples group G6B): 4-methylcyclohexyl group.
[0049] - Si(R 901 ) (Caution 902 ) (Caution 903 The group represented by ) as described herein -Si(R 901 ) (Caution 902) (Caution 903 Specific examples of the group represented by (Specific Examples Group G7) 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" as described in Specific Examples Group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in Specific Examples Group G2. G3 is a "substituted or unsubstituted alkyl group" as described in Specific Examples Group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Examples Group G6. In -Si(G1)(G1)(G1), the multiple G1s are either identical or different from one another. - In Si(G1)(G2)(G2), multiple G2s are either identical or different from each other. - In Si(G1)(G1)(G2), multiple G1s are either identical or different from each other. - In Si(G2)(G2)(G2), multiple G2s are either identical or different from each other. - In Si(G3)(G3)(G3), multiple G3s are either identical or different from each other. - In Si(G6)(G6)(G6), multiple G6s are either identical or different from each other.
[0050] ・"-O-(R 904 The group represented by ) as described herein -O-(R 904 Specific examples of the group represented by (Specific Examples Group G8) include -O(G1), -O(G2), -O(G3), and -O(G6). Here, G1 is a "substituted or unsubstituted aryl group" as described in Specific Examples Group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in Specific Examples Group G2. G3 is a "substituted or unsubstituted alkyl group" as described in Specific Examples Group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Examples Group G6.
[0051] ・"-S-(R 905 The group represented by ) as described herein -S-(R 905Specific examples of the group represented by (Specific Examples Group G9) include -S (G1), -S (G2), -S (G3), and -S (G6). Here, G1 is a "substituted or unsubstituted aryl group" as described in Specific Examples Group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in Specific Examples Group G2. G3 is a "substituted or unsubstituted alkyl group" as described in Specific Examples Group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Examples Group G6.
[0052] -N(R) 906 ) (Caution 907 The group represented by ) as described herein -N(R 906 ) (Caution 907 Specific examples of the group represented by (Specific Examples Group G10) 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" as described in Specific Examples Group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in Specific Examples Group G2. G3 is a "substituted or unsubstituted alkyl group" as described in Specific Examples Group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Examples Group G6. In -N(G1)(G1), the multiple G1s are either identical or different from each other. In -N(G2)(G2), the multiple G2s are either identical or different from each other. In -N(G3)(G3), the multiple G3s are either identical or different from each other. -N(G6)(G6) The multiple G6s are either identical or different from one another.
[0053] ・"Halogen atom" Specific examples of "halogen atom" as described herein (Specific Examples Group G11) include fluorine atom, chlorine atom, bromine atom, and iodine atom.
[0054] - "Substituted or unsubstituted fluoroalkyl groups" The "substituted or unsubstituted fluoroalkyl groups" described herein refer to groups in which at least one hydrogen atom bonded to the carbon atoms constituting the alkyl group is replaced by a fluorine atom, and also include groups in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group are replaced by fluorine atoms (perfluoro groups). The number of carbon atoms in an "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. "Substituted fluoroalkyl groups" refer to groups in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced by substituents. The "substituted fluoroalkyl groups" described herein also include groups in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent are further replaced by substituents. Specific examples of "unsubstituted fluoroalkyl groups" include groups in which one or more hydrogen atoms in the aforementioned "alkyl group" (specific example group G3) are replaced by fluorine atoms.
[0055] - "Substituted or unsubstituted haloalkyl groups" The "substituted or unsubstituted haloalkyl groups" described herein refer to groups in which at least one hydrogen atom bonded to the carbon atoms constituting the alkyl group is replaced by a halogen atom, and also include groups in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group are replaced by 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. "Substituted haloalkyl groups" refer to groups in which one or more hydrogen atoms of a "haloalkyl group" are replaced by substituents. The "substituted haloalkyl groups" described herein also include groups in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent are further replaced by substituents. Specific examples of "unsubstituted haloalkyl groups" include groups in which one or more hydrogen atoms in the aforementioned "alkyl group" (specific example group G3) are replaced by halogen atoms. Haloalkyl groups are sometimes referred to as alkyl halides.
[0056] - "Substituted or unsubstituted alkoxy groups" Specific examples of "substituted or unsubstituted alkoxy groups" as described herein include the group represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. The number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein.
[0057] - "substituted or unsubstituted alkylthio group" A specific example of the "substituted or unsubstituted alkylthio group" described herein is the group represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. The number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein.
[0058] - "substituted or unsubstituted aryloxy group" A specific example of the "substituted or unsubstituted aryloxy group" described herein is a group represented by -O(G1), where G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein.
[0059] - "substituted or unsubstituted arylthio group" A specific example of the "substituted or unsubstituted arylthio group" described herein is the group represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein.
[0060] - "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described herein is a group represented by -Si(G3)(G3)(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) are either the same or different from each other. 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, unless otherwise specified herein.
[0061] - "Substituted or unsubstituted aralkyl group" A specific example of the "substituted or unsubstituted aralkyl group" described herein is a group represented by -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3, and G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. Therefore, an "aralkyl group" is a group in which the hydrogen atom of an "alkyl group" is replaced by an "aryl group" as a substituent, and is one form of a "substituted alkyl group". An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" in which an "unsubstituted aryl group" is substituted, 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 herein. Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.
[0062] Unless otherwise specified herein, the substituted or unsubstituted aryl groups are preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, pyrenyl, chrysenyl, triphenylenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl.
[0063] Unless otherwise specified herein, the substituted or unsubstituted heterocyclic groups are preferably pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, benzimidazolyl, phenanthrolinyl, carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, or 9-carbazolyl), benzocarbazolyl, azacarbazolyl, diazacarbazolyl, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, aza These include dibenzothiophenyl group, diazadibenzothiophenyl group, (9-phenyl)carbazolyl group ((9-phenyl)carbazole-1-yl group, (9-phenyl)carbazole-2-yl group, (9-phenyl)carbazole-3-yl group, or (9-phenyl)carbazole-4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazole-9-yl group, phenylcarbazole-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group, etc.
[0064] In this specification, unless otherwise specified, the carbazolyl group is specifically one of the following groups:
[0065]
[0066] In this specification, the (9-phenyl)carbazolyl group is, unless otherwise specified herein, one of the following groups:
[0067]
[0068] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents the bond position.
[0069] In this specification, unless otherwise specified, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups:
[0070]
[0071] In the general formulas (TEMP-34) to (TEMP-41) above, * represents the bond position.
[0072] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and t-butyl groups.
[0073] - "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described herein is a divalent group derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described above. Specific examples of "substituted or unsubstituted arylene groups" (Specific Examples Group G12) include divalent groups derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described in Specific Examples Group G1.
[0074] - "Substitutable or unsubstituted divalent heterocyclic groups" Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic groups" described herein are divalent groups derived by removing one hydrogen atom from the heterocycle of the "substituted or unsubstituted heterocyclic groups" described above. Specific examples of "substituted or unsubstituted divalent heterocyclic groups" (Specific Examples Group G13) include divalent groups derived by removing one hydrogen atom from the heterocycle of the "substituted or unsubstituted heterocyclic groups" described in Specific Examples Group G2.
[0075] - "Substituted or unsubstituted alkylene group" Unless otherwise specified, the "substituted or unsubstituted alkylene group" described herein is a divalent group derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl group" described above. Specific examples of the "substituted or unsubstituted alkylene group" (Specific Examples Group G14) include the divalent group derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl group" described in Specific Examples Group G3.
[0076] Unless otherwise specified herein, the substituted or unsubstituted arylene groups are preferably any of the following general formulas (TEMP-42) to (TEMP-68).
[0077]
[0078]
[0079] In the above general formulas (TEMP-42) to (TEMP-52), Q 1 ~Q 10 Each of these is independently a hydrogen atom or a substituent. In the general formulas (TEMP-42) to (TEMP-52) above, * represents a bond position.
[0080]
[0081] In the above general formulas (TEMP-53) to (TEMP-62), Q 1 ~Q 10 Each of these is independently either a hydrogen atom or a substituent. Formula Q 9 and Q 10 These elements may be bonded to each other via single bonds to form a ring. In the general formulas (TEMP-53) to (TEMP-62), * indicates a bond position.
[0082]
[0083] In the above general formulas (TEMP-63) to (TEMP-68), Q 1 ~Q 8 Each of these is independently a hydrogen atom or a substituent. In the general formulas (TEMP-63) to (TEMP-68), * represents a bond position.
[0084] Unless otherwise specified herein, the substituted or unsubstituted divalent heterocyclic groups described herein are preferably any of the following general formulas (TEMP-69) to (TEMP-102).
[0085]
[0086]
[0087]
[0088] In the above general formulas (TEMP-69) to (TEMP-82), Q 1 ~Q 9 Each of these is independently either a hydrogen atom or a substituent.
[0089]
[0090]
[0091]
[0092]
[0093] In the above general formulas (TEMP-83) to (TEMP-102), Q 1 ~Q 8 Each of these is independently either a hydrogen atom or a substituent.
[0094] The above is a description of the substituents described herein.
[0095] ・"When they combine to form a ring" In this specification, "one or more pairs of adjacent elements combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine with each other" means the case in which "one or more pairs of adjacent elements combine to form a substituted or unsubstituted monoring," the case in which "one or more pairs of adjacent elements combine to form a substituted or unsubstituted fused ring," and the case in which "one or more pairs of adjacent elements do not combine with each other." The cases in this specification where "one or more pairs of adjacent elements combine to form a substituted or unsubstituted monoring" and the case where "one or more pairs of adjacent elements combine to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "when they combine to form a ring") will be explained below. We will explain using the example of an anthracene compound represented by the following general formula (TEMP-103), whose parent skeleton is an anthracene ring.
[0096]
[0097] For example, R 921~R 930 In the case where "one or more pairs of adjacent groups are joined together to form a ring," the pairs of adjacent groups that make up one set are R 921 and R 922 The group, R 922 and R 923 The group, R 923 and R 924 The group, R 924 and R 930 The group, R 930 and R 925 The group, R 925 and R 926 The group, R 926 and R 927 The group, R 927 and R 928 The group, R 928 and R 929 The pair with, and R 929 and R 921 They are a pair.
[0098] The phrase "one or more sets" above means that two or more sets of the above-mentioned sets of two or more adjacent elements may simultaneously form a ring. For example, R 921 and R 922 and are joined to each other to form a ring Q A Forms R 925 and R 926 and are joined to each other to form a ring Q B If the above general formula (TEMP-103) is formed, the anthracene compound represented by the above general formula (TEMP-104) is represented by the following general formula (TEMP-104).
[0099]
[0100] The case where "two or more adjacent elements form a ring" includes not only cases where two adjacent elements are joined, as in the example above, but also cases where three or more adjacent elements are joined. For example, R 921 and R 922 and are joined to each other to form a ring Q A Forms R 922 and R 923 and are joined to each other to form a ring Q C It forms three adjacent (R 921 , R 922 and R923 means a case where a pair of ) bonds to each other to form a ring that is fused to the anthracene parent skeleton; in this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C share R 922 .
[0101]
[0102] The formed "monocyclic ring" or "fused ring" may be a saturated ring or an unsaturated ring, when considered only as the structure of the formed ring. Even in a case where "one pair consisting of two adjacent groups" forms a "monocyclic ring" or a "fused ring", the "monocyclic ring" or "fused ring" can form a saturated ring or an unsaturated ring. For example, ring Q formed in the general formula (TEMP-104) A and ring Q B are each a "monocyclic ring" or a "fused ring". Further, ring Q formed in the general formula (TEMP-105) A and ring Q C are "fused rings". Ring Q of the general formula (TEMP-105) A and ring Q C form a fused ring as a result of the fusion of ring Q A and ring Q C . If ring Q of the general formula (TMEP-104) A is a benzene ring, ring Q A is a monocyclic ring. If ring Q of the general formula (TMEP-104) A is a naphthalene ring, ring Q A is a fused ring.
[0103] 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 the aromatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G1 are terminated with a hydrogen atom. Specific examples of the aromatic heterocyclic ring include structures in which the aromatic heterocyclic groups exemplified as specific examples in Specific Example Group G2 are terminated with a hydrogen atom. Specific examples of the aliphatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G6 are terminated with a hydrogen atom. The phrase "form a ring" means forming a ring with only a plurality of atoms of the mother skeleton, or with a plurality of atoms of the mother skeleton and one or more additional arbitrary elements. For example, R shown in the general formula (TEMP-104) described above 921 and R 922 are bonded to each other to form ring Q A means a ring formed by the carbon atom of the anthracene skeleton to which R 921 binds, the carbon atom of the anthracene skeleton to which R 922 binds, and one or more arbitrary elements. As a specific example, when R 921 and R 922 form ring Q A in the case of forming, the carbon atom of the anthracene skeleton to which R 921 binds, the carbon atom of the anthracene skeleton to which R 922 binds, and four carbon atoms form a monocyclic unsaturated ring, the ring formed by R 921 and R 922 is a benzene ring.
[0104] Here, "any element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur, unless otherwise specified herein. In any element (for example, carbon or nitrogen), bonds that do not form a ring may be terminated with a hydrogen atom or the like, or substituted with "any substituent" as described later. If any element other than carbon is included, the formed ring is a heterocycle. Unless otherwise specified herein, "one or more any elements" constituting a 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 "monocycle" and "fused ring," "monocycle" is preferred. Unless otherwise specified herein, of "saturated ring" and "unsaturated ring," "unsaturated ring" is preferred. Unless otherwise specified herein, "monocycle" is preferably a benzene ring. Unless otherwise specified herein, "unsaturated ring" is preferably a benzene ring. When "one or more sets of two or more adjacent elements" "bond to each other to form a substituted or unsubstituted monoring" or "bond to each other to form a substituted or unsubstituted fused ring", unless otherwise specified herein, preferably, one or more sets of two or more adjacent elements bond to each other to form a substituted or unsubstituted "unsaturated ring" consisting of multiple atoms of the parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur elements, ranging from one to fifteen.
[0105] The substituents in the case where the above-mentioned "mono-ring" or "fused ring" has substituents are, for example, "any substituents" as described later. Specific examples of substituents in the case where the above-mentioned "mono-ring" or "fused ring" has substituents are the substituents described in the section "Substituents as described in this specification" above. The substituents in the case where the above-mentioned "saturated ring" or "unsaturated ring" has substituents are, for example, "any substituents" as described later. Specific examples of substituents in the case where the above-mentioned "mono-ring" or "fused ring" has substituents are the substituents described in the section "Substituents as described in this specification" above. The above explains the cases where "one or more sets of two or more adjacent elements are bonded to each other to form a substituted or unsubstituted mono-ring" and where "one or more sets of two or more adjacent elements are bonded to each other to form a substituted or unsubstituted fused ring" ("when they are bonded to form a ring").
[0106] - Substituents in the case of "substituted or unsubstituted" In one embodiment of this specification, the substituents in the case of "substituted or unsubstituted" (which may be referred to as "any substituents" in this specification) are, for example, unsubstituted C1-C50 alkyl groups, unsubstituted C2-C50 alkenyl groups, unsubstituted C2-C50 alkynyl groups, unsubstituted ring-forming C3-C50 cycloalkyl groups, -Si(R 901 ) (Caution 902 ) (Caution 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 ) (Caution 907 ), a group selected from the group consisting of halogen atoms, cyano groups, nitro groups, unsubstituted aryl groups with 6 to 50 ring-forming atoms, and unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms, where R 901 ~R 907 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group. 901 If there are two or more of them, then there are two or more R901 They are either identical or different from each other, R 902 If there are two or more of them, then there are two or more R 902 They are either identical or different from each other, R 903 If there are two or more of them, then there are two or more R 903 They are either identical or different from each other, R 904 If there are two or more of them, then there are two or more R 904 They are either identical or different from each other, R 905 If there are two or more of them, then there are two or more R 905 They are either identical or different from each other, R 906 If there are two or more of them, then there are two or more R 906 They are either identical or different from each other, R 907 If there are two or more of them, then there are two or more R 907 They are either identical or different from one another.
[0107] In one embodiment, the substituent in the case of "substituted or unsubstituted" is a group selected from the group consisting of alkyl groups having 1 to 50 carbon atoms, aryl groups having 6 to 50 ring-forming carbon atoms, and heterocyclic groups having 5 to 50 ring-forming atoms.
[0108] In one embodiment, the substituent in the case of "substituted or unsubstituted" is a group selected from the group consisting of alkyl groups having 1 to 18 carbon atoms, aryl groups having 6 to 18 ring-forming carbon atoms, and heterocyclic groups having 5 to 18 ring-forming atoms.
[0109] Specific examples of each of the above-mentioned substituents are the specific examples of substituents described in the section "Substituents as described herein" above.
[0110] Unless otherwise specified herein, any adjacent substituents may form a "saturated ring" or an "unsaturated ring," preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, and more preferably a benzene ring. Unless otherwise specified herein, any substituent may have further substituents, the same as those described above for any substituent.
[0111] In this specification, a numerical range expressed using "AA to BB" means a range that includes the numerical value AA, which is written before "AA to BB", as the lower limit, and the numerical value BB, which is written after "AA to BB", as the upper limit.
[0112] [First Embodiment] <Organic Electroluminescent Element> One embodiment of the organic EL element according to this embodiment includes a cathode, an anode, and a light-emitting unit disposed between the cathode and the anode. The light-emitting unit includes a light-emitting band. In the organic EL element according to this embodiment, the light-emitting band is disposed between the anode and the cathode. In the organic EL element according to this embodiment, the light-emitting band includes a first light-emitting layer and a second light-emitting layer. In addition to the first light-emitting layer and the second light-emitting layer included in the light-emitting band, the light-emitting unit may have one or more layers containing at least one selected from the group consisting of organic compounds and inorganic substances. Inorganic substances are at least one of inorganic compounds and elemental substances. Preferably, the light-emitting unit includes one or more layers selected from the group consisting of layers composed of organic compounds, layers composed of inorganic substances, and layers composed of both organic compounds and inorganic substances. Examples of layers that the light-emitting unit may include in addition to the first light-emitting layer and the second light-emitting layer include layers that can be used in organic EL elements. The layers that can be used in an organic EL device are not particularly limited, but examples include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a barrier layer.
[0113] The organic EL element according to this embodiment includes the organic EL element according to the first embodiment described below.
[0114] The organic EL element according to the first embodiment of this embodiment has an anode, a cathode, and a light-emitting band disposed between the anode and the cathode, and in the organic EL element according to this first embodiment, the anode, the light-emitting band, and the cathode are arranged in this order, the light-emitting band includes a first light-emitting layer and a second light-emitting layer, the first light-emitting layer contains a first host material and a first dopant material, the second light-emitting layer contains a second host material and a second dopant material, the first host material and the second host material are different from each other, the first dopant material is a light-emitting compound with a maximum peak wavelength of 500 nm or less, the second dopant material is a light-emitting compound with a maximum peak wavelength of 500 nm or less, the first dopant material and the second dopant material are different from each other, and the triplet energy T of the first host material 1 (H1) and the triplet energy T of the second host material 1 (H2) and satisfy the relationship in equation (Equation 1), and the first dopant material HOMO(D1) and the second dopant material HOMO(D2) satisfy the relationship in equation (Equation 2C) below. 1 (H1)>T 1 (H2)...(Math. 1) HOMO(D1)-HOMO(D2)>0.25eV...(Math. 2C)
[0115] In the organic EL element according to this embodiment, the stacked first light-emitting layer and the second light-emitting layer contain compounds that satisfy the relationship between formulas (Equation 1) and (Equation 2C) as the first host material, first dopant material, second host material, and second dopant material. Therefore, the organic EL element according to this embodiment can emit light with high efficiency and long lifespan.
[0116] <Relationship between the first and second light-emitting layers> (TTF mechanism) Conventionally, Triplet-Triple-Annihilation (sometimes referred to as TTA) is known as a technique for improving the luminescence efficiency of organic electroluminescent elements. TTA is a mechanism in which triplet excitons collide with triplet excitons to produce singlet excitons. The TTA mechanism is sometimes referred to as the TTF mechanism. The TTF mechanism is described, for example, in International Publication No. 2007 / 138906.
[0117] This explains the TTF phenomenon. Holes injected from the anode and electrons injected from the cathode recombine in the light-emitting layer to generate excitons. As has been known, the spin states of these excitons are 25% singlet excitons and 75% triplet excitons. In conventionally known fluorescent devices, 25% of singlet excitons emit light when they relax to the ground state, but the remaining 75% of 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 devices was said to be 25%. On the other hand, the behavior of triplet excitons generated inside organic materials has been theoretically investigated. According to S. M. Bachilo et al. (J. Phys. Cem. A, 104, 7711 (2000)), assuming that higher-order excitons such as quintet excitons immediately return to the triplet state, triplet excitons (hereinafter, 3 A * When the density of (described as) increases, triplet excitons collide with each other, and the reaction shown in the following equation occurs. Here, 1 A represents the ground state, 1 A * This 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 *Therefore, it is predicted that 1 / 5, or 20%, of the 75% of triplet excitons initially generated will change into singlet excitons. Consequently, the singlet excitons contributing as light will be 40%, which is the initial 25% plus 75% × (1 / 5) = 15%. In this case, the ratio of emission from TTF to the total emission intensity (TTF ratio) will be 15 / 40, or 37.5%. Furthermore, if we assume that the 75% of the initially generated triplet excitons collide with each other to generate singlet excitons (one singlet exciton is generated from two triplet excitons), then a very high internal quantum efficiency of 62.5% is obtained, which is the initial 25% of singlet excitons plus 75% × (1 / 2) = 37.5%. In this case, the TTF ratio is 37.5 / 62.5 = 60%.
[0118] According to the organic electroluminescent element of this embodiment, triplet excitons generated by the recombination of holes and electrons in the first light-emitting layer are less likely to be quenched at the interface between the first light-emitting layer and the organic layer in direct contact with the first light-emitting layer, even if there is an excess of carriers at the interface between the first light-emitting layer and the organic layer in direct contact with the first light-emitting layer. For example, if the recombination region is locally located at the interface between the first light-emitting layer and the hole transport layer or electron barrier layer, quenching by an excess of electrons is possible. On the other hand, if the recombination region is locally located at the interface between the first light-emitting layer and the electron transport layer or hole barrier layer, quenching by an excess of holes is possible.
[0119] The organic electroluminescent element according to this embodiment comprises at least two light-emitting layers (i.e., a first light-emitting layer and a second light-emitting layer) that satisfy a predetermined relationship, wherein the triplet energy T of the first host material in the first light-emitting layer 1 (H1) and the triplet energy T of the second host material in the second light-emitting layer 1(H2) satisfies the relationship in formula (Equation 1). By providing a first light-emitting layer and a second light-emitting layer that satisfy the relationship in formula (Equation 1), triplet excitons generated in the first light-emitting layer move to the second light-emitting layer without being quenched by excess carriers, and the reverse movement from the second light-emitting layer to the first light-emitting layer can be suppressed. As a result, the TTF mechanism is expressed in the second light-emitting layer, singlet excitons are efficiently generated, and the luminescence efficiency is improved. Thus, the organic electroluminescent element is provided with a first light-emitting layer that mainly generates triplet excitons and a second light-emitting layer that mainly expresses the TTF mechanism by utilizing triplet excitons that have moved from the first light-emitting layer as different regions, and by using a compound with a smaller triplet energy than the first host material in the first light-emitting layer as the second host material in the second light-emitting layer, a difference in triplet energy is created, thereby improving the luminescence efficiency.
[0120] In the organic EL element of this embodiment, the triplet energy T of the first host material 1 (H1) and the triplet energy T of the second host material 1 It is preferable that (H2) and satisfy the relationship shown in the following formula (Equation 5). 1 (H1)-T 1 (H2) > 0.03 eV ... (Math 5)
[0121] In this specification, "host material" refers to a material that is included in the layer in an amount of, for example, "50% by mass or more". Therefore, the first light-emitting layer contains, for example, the first host material in an amount of 50% by mass or more of the total mass of the first light-emitting layer. The second light-emitting layer contains, for example, the second host material in an amount of 50% by mass or more of the total mass of the second light-emitting layer.
[0122] (Emission Wavelength of Organic EL Element) In this embodiment, it is preferable that the organic electroluminescent element emits light with a maximum peak wavelength of 500 nm or less when the element is driven. More preferably, in this embodiment, the organic electroluminescent element emits light with a maximum peak wavelength of 430 nm or more and 480 nm or less when the element is driven. The maximum peak wavelength of the light emitted by the organic EL element when the element is driven is measured as follows: Current density is 10 mA / cm².2 The spectral radiance spectrum of an organic EL element is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) when a voltage is applied to the element in such a manner. The peak wavelength of the emission spectrum with the maximum emission intensity is measured from the obtained spectral radiance spectrum and defined as the maximum peak wavelength (unit: nm).
[0123] The organic EL element according to this embodiment may have a first light-emitting layer and a second light-emitting layer in this order from the anode side to the cathode side, or it may have a second light-emitting layer and a first light-emitting layer in this order from the anode side to the cathode side. In either case of the order of the first and second light-emitting layers, by selecting a combination of materials that satisfies the relationship in the above formula (Equation 1), the effects of a laminated configuration of light-emitting layers can be expected.
[0124] In the organic EL element of this embodiment, the triplet energy T of the first host material 1 It is preferable that (H1) satisfies the relationship shown in the following formula (Equation 12). 1 (H1) > 2.0 eV ... (Math 12)
[0125] In the organic EL element according to this embodiment, the triplet energy T of the second host material 1 It is preferable that (H2) satisfies the relationship in the following formula (Equation 13X), and more preferably that it satisfies the relationship in the following formula (Equation 13).
[0126] In the organic EL element of this embodiment, the triplet energy T of the second host material 1 It is also preferable that (H2) satisfies the following relationship (Equation 14): 1.9eV≧T 1 (H2) ... (Number 14)
[0127] In the organic EL element according to this embodiment, the triplet energy T of the second host material 1 It is also preferable that (H2) satisfies the following relationship (Equation 13A): 1.90 eV > T 1 (H2) ≥ 1.80 eV …(Equation 13A)
[0128] In the organic EL element of this embodiment, the triplet energy T of the second host material 1(D2) and the triplet energy T of the second dopant material. 1 It is preferable that (H2) and satisfy the relationship shown in the following formula (Equation 3). 1 (D2) > T 1 (H2) ... (Math 3)
[0129] In the organic EL element of this embodiment, it is preferable that the first dopant material HOMO(D1) and the second dopant material HOMO(D2) satisfy the following relationship (Equation 21): HOMO(D1) - HOMO(D2) ≥ 0.28 eV …(Equation 21)
[0130] In the organic EL element of this embodiment, it is preferable that the first dopant material HOMO(D1) and the second dopant material HOMO(D2) satisfy the following relationship (Equation 22): HOMO(D1) - HOMO(D2) ≤ 0.50 eV …(Equation 22)
[0131] In one embodiment of the organic EL element of this embodiment, it is preferable that the first host material HOMO(H1), the first dopant material HOMO(D1), the second host material HOMO(H2), and the second dopant material HOMO(D2) satisfy the following relationship (Equation 3A) or the following relationship (Equation 3D): HOMO(D1) - HOMO(H1) > HOMO(D2) - HOMO(H2) ... (Equation 3A) HOMO(D1) - HOMO(H1) < HOMO(D2) - HOMO(H2) ... (Equation 3D)
[0132] In the organic EL element of this embodiment, it is preferable that the first host material HOMO(H1) and the first dopant material HOMO(D1) satisfy the following relationship (Equation 3B): HOMO(D1) - HOMO(H1) < 0.80 eV ... (Equation 3B)
[0133] In the organic EL element of this embodiment, it is preferable that the second host material HOMO(H2) and the second dopant material HOMO(D2) satisfy the following relationship (Equation 3C): HOMO(D2) - HOMO(H2) < 0.50 eV ... (Equation 3C)
[0134] In the organic EL element according to this embodiment, it is preferable to include a first light-emitting layer between the anode and the cathode, and a second light-emitting layer between the first light-emitting layer and the cathode.
[0135] In the organic EL element according to this embodiment, it is preferable that the first light-emitting layer and the second light-emitting layer are in direct contact.
[0136] In this specification, the layer structure in which "the first light-emitting layer and the second light-emitting layer are in direct contact" may also include, for example, any of the following embodiments (LS1), (LS2), and (LS3): (LS1) An embodiment in which, during the process of vapor deposition of the compound relating to the first light-emitting layer and the process of vapor deposition of the compound relating to the second light-emitting layer, a region is created in which both the first host material and the second host material are mixed, and this region is located at the interface between the first light-emitting layer and the second light-emitting layer. (LS2) An embodiment in which, when the first light-emitting layer and the second light-emitting layer contain a luminescent compound, a region is created in which the first host material, the second host material, and the luminescent compound are mixed during the process of vapor deposition of the compound relating to the first light-emitting layer and the process of vapor deposition of the compound relating to the second light-emitting layer, and this region is located at the interface between the first light-emitting layer and the second light-emitting layer. (LS3) A configuration in which, when the first light-emitting layer and the second light-emitting layer contain a light-emitting compound, a region made of the light-emitting compound, a region made of the first host material, or a region made of the second host material is generated during the process of vapor deposition of the compound relating to the first light-emitting layer and the vapor deposition of the compound relating to the second light-emitting layer, and such region is located at the interface between the first light-emitting layer and the second light-emitting layer.
[0137] In the above embodiments (LS1) to (LS3), the luminescent compound is, for example, at least one of the first dopant material and the second dopant material.
[0138] In the organic EL element of this embodiment, the triplet energy T of the first dopant material or the second dopant material 1 (DX) and the triplet energy T of the first host material. 1 (H1) and the triplet energy T of the second host material 1It is preferable that (H2) and satisfy the relationship of the following formula (Equation 10X) or (Equation 10), and it is more preferable that they satisfy the relationship of the following formula (Equation 10). 2.70 eV > T 1 (DX) > T 1 (H1)>T 1 (H2) ... (Math 10X) 2.60 eV > T 1 (DX) > T 1 (H1)>T 1 (H2) ... (Number 10)
[0139] In one embodiment of the organic EL element according to this embodiment, the triplet energy T of the first dopant material 1 (D1) preferably satisfies the relationship in the following formula (Equation 10AX), and more preferably satisfies the relationship in the following formula (Equation 10A). 2.70 eV > T 1 (D1) > T 1 (H1)>T 1 (H2) ... (Math 10AX) 2.60 eV > T 1 (D1) > T 1 (H1)>T 1 (H2) ... (Mathematics 10A)
[0140] In one embodiment of the organic EL element according to this embodiment, the triplet energy T of the second dopant material 1 (D2) preferably satisfies the relationship in the following formula (Equation 10BX), and more preferably satisfies the relationship in the following formula (Equation 10B): 2.70 eV > T 1 (D2) > T 1 (H1)>T 1 (H2) ... (Number 10BX) 2.60 eV > T 1 (D2) > T 1 (H1)>T 1 (H2) ...(Number 10B)
[0141] In the organic EL element according to this embodiment, the triplet energy T of the first dopant material or the second dopant material 1 (DX) and the triplet energy T of the first host material. 1 It is preferable that (H1) and satisfy the relationship in the following formula (Equation 11X), and it is also preferable that they satisfy the relationship in the following formula (Equation 11): 0 eV < T 1(DX)-T 1 (H1) < 0.70 eV ... (Equation 11X) 0 eV < T 1 (DX)-T 1 (H1) < 0.60 eV ... (Equation 11)
[0142] In the organic EL element according to this embodiment, the triplet energy T of the first dopant material 1 (D1) preferably satisfies the relationship in the following formula (Equation 11AX), and also preferably satisfies the relationship in the following formula (Equation 11A): 0 eV < T 1 (D1)-T 1 (H1) < 0.70 eV ... (Equation 11AX) 0 eV < T 1 (D1)-T 1 (H1) < 0.60 eV ... (Mathematics 11A)
[0143] In the organic EL element according to this embodiment, the triplet energy T of the second dopant material 1 (D2) preferably satisfies the relationship in the following formula (Equation 11BX), and also preferably satisfies the relationship in the following formula (Equation 11B): -0.15eV < T 1 (D2)-T 1 (H1) < 0.70 eV ... (Equation 11BX) 0 eV < T 1 (D2)-T 1 (H2) < 0.80 eV ... (Math 11B)
[0144] In the organic EL element according to this embodiment, when the stacking order of the first light-emitting layer and the second light-emitting layer is from the anode side, in the order of the first light-emitting layer and the second light-emitting layer, it is also preferable that the electron mobility μe(H1) of the first host material and the electron mobility μe(H2) of the second host material satisfy the following equation (Equation 30): μe(H2) > μe(H1) ... (Equation 30) When the first host material and the second host material satisfy the above equation (Equation 30), the recombination ability of holes and electrons in the first light-emitting layer is improved.
[0145] In the organic EL element according to this embodiment, when the stacking order of the first light-emitting layer and the second light-emitting layer is from the anode side to the second light-emitting layer, it is also preferable that the hole mobility μh(H1) of the first host material and the hole mobility μh(H2) of the second host material satisfy the following relationship (Equation 31): μh(H1) > μh(H2) ... (Equation 31)
[0146] In the organic EL element according to this embodiment, when the stacking order of the first light-emitting layer and the second light-emitting layer is from the anode side to the second light-emitting layer, it is also preferable that the hole mobility μh(H1) of the first host material, the electron mobility μe(H1) of the first host material, the hole mobility μh(H2) of the second host material, and the electron mobility μe(H2) of the second host material satisfy the following equation (Equation 32): (μe(H2) / μh(H2)) > (μe(H1) / μh(H1)) ... (Equation 32)
[0147] Electron mobility can be measured by impedance measurement using a mobility evaluation element fabricated according to the following procedure. The mobility evaluation element is fabricated, for example, according to the following procedure. A target layer is formed by depositing the compound Target, which is the target of electron mobility measurement, onto a glass substrate with an aluminum electrode (anode), covering the aluminum electrode. An electron transport layer is formed by depositing the compound ET-A shown below onto this target layer. An electron injection layer is formed by depositing LiF onto this electron transport layer. A metallic cathode is formed by depositing metallic aluminum (Al) onto this electron injection layer. The above mobility evaluation element configuration is schematically shown as follows: glass / Al(50) / Target(200) / ET-A(10) / LiF(1) / Al(50) The numbers in parentheses indicate the film thickness (nm).
[0148]
[0149] An element for evaluating electron mobility is installed in an impedance measuring device, and impedance measurement is performed. The impedance measurement is performed by sweeping the measurement frequency from 1 Hz to 1 MHz. At that time, a DC voltage V is applied to the element simultaneously with an AC amplitude of 0.1 V. From the measured impedance Z, the modulus M is calculated using the relationship in the following formula (C1). Formula (C1): M = jωZ In the above formula (C1), j is the imaginary unit whose square is -1, and ω is the angular frequency [rad / s]. In a Bode plot with the imaginary part of the modulus M on the vertical axis and frequency [Hz] on the horizontal axis, the electrical time constant τ of the mobility evaluation element is obtained from the frequency fmax that shows the peak using the following formula (C2). Formula (C2): τ = 1 / (2πfmax) In the above formula (C2), π is the symbol for pi. Using the above τ, the electron mobility μe is calculated from the relationship in the following formula (C3-1). Calculation formula (C3-1): μe=d 2 / (Vτ) In the above calculation formula (C3-1), d is the total thickness of the organic thin film constituting the device, and in the case of a device configuration for evaluating electron mobility, d = 210 [nm].
[0150] Hole mobility can be measured by impedance measurement using a mobility evaluation element fabricated according to the following procedure. The mobility evaluation element is fabricated, for example, according to the following procedure: A hole injection layer is formed by depositing the following compound HA-2 onto a glass substrate with an ITO transparent electrode (anode), covering the transparent electrode. A hole transport layer is formed by depositing the following compound HT-A on top of this hole injection layer. Subsequently, a measurement target layer is formed by depositing the compound Target, whose hole mobility is to be measured. A metallic cathode is formed by depositing metallic aluminum (Al) on top of this measurement target layer. The above mobility evaluation element configuration is schematically shown as follows: ITO(130) / HA-2(5) / HT-A(10) / Target(200) / Al(80) The numbers in parentheses indicate the film thickness (nm).
[0151]
[0152] An element for evaluating hole mobility is installed in an impedance measuring device, and impedance measurement is performed. The impedance measurement is performed by sweeping the measurement frequency from 1 Hz to 1 MHz. At that time, a DC voltage V is applied to the element simultaneously with an AC amplitude of 0.1 V. From the measured impedance Z, the modulus M is calculated using the relationship in the calculation formula (C1). In a Bode plot with the imaginary part of the modulus M on the vertical axis and frequency [Hz] on the horizontal axis, the electrical time constant τ of the mobility evaluation element is determined from the frequency fmax showing the peak using the calculation formula (C2). Using the τ obtained from the calculation formula (C2), the hole mobility μh is calculated from the relationship in the following calculation formula (C3-2). Calculation formula (C3-2): μh = d 2 / (Vτ) In the above calculation formula (C3-2), d is the total thickness of the organic thin film constituting the element, and in the case of an element configuration for evaluating hole mobility, d = 215 [nm].
[0153] In this specification, electron mobility and hole mobility are defined as the square root of the electric field strength E. 1/2 = 500 [V] 1/2 / cm 1/2 This is the value at the time of [ ]. The square root of the electric field strength E 1/2 This can be calculated from the relationship shown in the following formula (C4). Formula (C4): E 1/2 = V 1/2 / d 1/2 For the impedance measurement, Solartron's Model 1260 impedance measuring device is used, and for higher accuracy, Solartron's Model 1296 dielectric constant measurement interface can also be used in conjunction.
[0154] (First light-emitting layer) In the organic EL element according to this embodiment, the first light-emitting layer contains a first host material and a first dopant material.
[0155] In the organic EL element according to this embodiment, it is preferable that the first light-emitting layer does not contain a metal complex.
[0156] In the organic EL element according to this embodiment, it is also preferable that the first light-emitting layer does not contain a boron-containing complex.
[0157] In the organic EL element according to this embodiment, it is preferable that the first light-emitting layer does not contain a phosphorescent material.
[0158] In the organic EL element according to this embodiment, it is preferable that the first light-emitting layer does not contain heavy metal complexes and phosphorescent rare earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.
[0159] In the organic EL element according to this embodiment, the singlet energy S of the first host material 1 (H1) and the singlet energy S of the first dopant material 1 It is preferable that (D1) and satisfy the relationship shown in the following formula (Formula 2). 1 (H1) > S 1 (D1) ... (Math 2)
[0160] When the first host material and the first dopant material satisfy the relationship shown in equation (Equation 2), singlet excitons generated on the first host material can easily transfer energy from the first host material to the first dopant material, contributing to the fluorescence emission of the first dopant material.
[0161] In the organic EL element of this embodiment, the triplet energy T of the first host material 1 (H1) and the triplet energy T of the first dopant material 1 It is preferable that (D1) and satisfy the relationship shown in the following formula (Equation 2A). 1 (D1) > T 1 (H1) ...(Math 2A)
[0162] Because the first host material and the first dopant material satisfy the relationship shown in the above formula (Equation 2A), triplet excitons generated in the first light-emitting layer move over the first host material rather than the first dopant material which has a higher triplet energy, making it easier for them to move to the second light-emitting layer.
[0163] The organic EL element according to this embodiment preferably satisfies the relationship shown in the following formula (Equation 2B). 1 (D1) > T 1 (H1)>T 1(H2) ...(Math 2B)
[0164] In the organic EL element according to this embodiment, the triplet energy T of the first host material 1 (H1) and the triplet energy T of the first dopant material 1 It is also preferable that (D1) and (Equation 2C) satisfy the following relationship. 1 (H1)>T 1 (D1) ... (Math 2C)
[0165] (Triplet energy T 1 ) Triplet energy T 1 The following methods can be used to measure the compound to be measured. -5 mol / L or more 10 -4 Dissolve the substance to a concentration of mol / L or less, and place this solution in a quartz cell to prepare the measurement sample. Measure the phosphorescence spectrum of this sample at a low temperature (77 K) (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength). Draw a tangent line to the rising edge of the short-wavelength side of this phosphorescence spectrum, and measure the wavelength λ at the intersection of this tangent line and the horizontal axis. edge Based on [nm], the amount of energy calculated from the following conversion formula (F1) is the triplet energy T 1 Let's assume the following. Conversion formula (F1): T 1 [eV]=1239.85 / λ edge
[0166] The tangent to the rise 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 wavelength maximum value of the spectrum, 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 value is maximum (i.e., the tangent at the inflection point) is taken as the tangent to the rise of the phosphorescence spectrum on the short-wavelength side. Note that maximum values with a peak intensity of 15% or less of the maximum peak intensity of the spectrum are not included in the shortest wavelength maximum value mentioned above, and the tangent drawn at the point closest to the shortest wavelength maximum value where the slope value is maximum is taken as the tangent to the rise of the phosphorescence spectrum on the short-wavelength side. For phosphorescence measurement, the Hitachi High-Technologies Corporation F-4500 spectrofluorometer can be used. However, the measuring apparatus is not limited to this; measurements may also be taken by combining a cooling device, a low-temperature container, an excitation light source, and a light-receiving device.
[0167] (Singlet energy S 1 ) Singlet energy S using solution 1 The following methods can be used to measure the compound to be measured (sometimes referred to as the solution method): -5 mol / L or more 10 -4 Prepare a toluene solution of mol / L or less and place it in a quartz cell. Measure the absorption spectrum of this sample at room temperature (300 K) (vertical axis: absorption intensity, horizontal axis: wavelength). Draw a tangent line to the falling edge on the long-wavelength side of this absorption spectrum, and substitute the wavelength value λedge [nm] at the intersection of the tangent line and the horizontal axis into the following conversion formula (F2) to calculate the singlet energy. Conversion formula (F2): S 1 [eV] = 1239.85 / λedge An example of an absorption spectrum measuring device is a spectrophotometer manufactured by Hitachi (device name: U3310), but it is not limited to this.
[0168] The tangent to the falling edge of the absorption spectrum on the longer wavelength side is drawn as follows: Consider the tangent at each point on the spectral curve as you move along the curve in the longer wavelength direction from the maximum value on the longest wavelength side of the absorption spectrum. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the value of the slope is minimized on the longest wavelength side (except when the absorbance is 0.1 or less) is taken as the tangent to the falling edge of the absorption spectrum on the longer wavelength side. Note that maximum values with absorbance of 0.2 or less are not included in the maximum value on the longest wavelength side mentioned above.
[0169] In the organic EL element according to this embodiment, the first dopant material is preferably contained in the first light-emitting layer in an amount exceeding 1.1% by mass. That is, the first light-emitting layer preferably contains the first dopant material in an amount exceeding 1.1% by mass of the total mass of the first light-emitting layer, more preferably 1.2% by mass or more of the total mass of the first light-emitting layer, even more preferably 1.5% by mass or more of the total mass of the first light-emitting layer, and even more preferably 2% by mass or more of the total mass of the first light-emitting layer. The first light-emitting layer preferably contains the first dopant material in an amount of 10% by mass or less of the total mass of the first light-emitting layer, more preferably 7% by mass or less of the total mass of the first light-emitting layer, and even more preferably 5% by mass or less of the total mass of the first light-emitting layer.
[0170] In the organic EL element according to this embodiment, the first light-emitting layer preferably contains the first compound as the first host material in an amount of 60% by mass or more of the total mass of the first light-emitting layer, more preferably 70% by mass or more of the total mass of the first light-emitting layer, even more preferably 80% by mass or more of the total mass of the first light-emitting layer, even more preferably 90% by mass or more of the total mass of the first light-emitting layer, and still more preferably 95% by mass or more of the total mass of the first light-emitting layer. The first light-emitting layer preferably contains the first host material in an amount of 99% by mass or less of the total mass of the first light-emitting layer, more preferably 98.8% by mass or less of the total mass of the first light-emitting layer, and even more preferably 98% by mass or less of the total mass of the first light-emitting layer. However, if the first light-emitting layer contains the first host material and the first dopant material, the upper limit of the total content of the first host material and the first dopant material is 100% by mass.
[0171] This embodiment does not exclude the first light-emitting layer from containing materials other than the first host material and the first dopant material. The first light-emitting layer may contain only one type of first host material, or two or more types. The first light-emitting layer may contain only one type of first dopant material, or two or more types.
[0172] In the organic EL element according to this embodiment, the thickness of the first light-emitting layer is preferably 3 nm or more, and more preferably 5 nm or more. If the thickness of the first light-emitting layer is 3 nm or more, it is a sufficient thickness for hole-electron recombination to occur in the first light-emitting layer. In the organic EL element according to this embodiment, the thickness of the first light-emitting layer is preferably 15 nm or less, and more preferably 10 nm or less. If the thickness of the first light-emitting layer is 15 nm or less, it is a sufficiently thin thickness for triplet excitons to move to the second light-emitting layer. In the organic EL element according to this embodiment, the thickness of the first light-emitting layer is preferably 3 nm or more and more preferably 15 nm or less.
[0173] (Second light-emitting layer)
[0174] In the organic EL element according to this embodiment, the second light-emitting layer contains a second host material and a second dopant material.
[0175] In the organic EL element according to this embodiment, it is preferable that the second light-emitting layer does not contain a metal complex.
[0176] In the organic EL element according to this embodiment, it is also preferable that the second light-emitting layer does not contain a boron-containing complex.
[0177] In the organic EL element according to this embodiment, it is preferable that the second light-emitting layer does not contain phosphorescent material (dopant material). In the organic EL element according to this embodiment, it is preferable that the second light-emitting layer does not contain heavy metal complexes and phosphorescent rare earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.
[0178] In the organic EL element according to this embodiment, the triplet energy T of the second dopant material 1 (D2) and the triplet energy T of the second host material 1 It is preferable that (H2) and satisfy the relationship shown in the following formula (Equation 3). 1 (D2) > T 1 (H2) ... (Math 3)
[0179] In the organic EL element according to this embodiment, the second dopant material and the second host material satisfy the relationship shown in equation (Equation 3). As a result, when triplet excitons generated in the first light-emitting layer move to the second light-emitting layer, they transfer energy to the molecules of the second host material, not to the second dopant material which has a higher triplet energy. Furthermore, triplet excitons generated by the recombination of holes and electrons on the second host material do not move to the second dopant material which has a higher triplet energy. Triplet excitons generated by recombination on the molecules of the second dopant material quickly transfer energy to the molecules of the second host material. Singlet excitons are generated on the second host material by the TTF phenomenon, where triplet excitons collide efficiently with each other without the triplet excitons of the second host material moving to the second dopant material.
[0180] In the organic EL element according to this embodiment, the singlet energy S of the second host material 1 (H2) and the singlet energy S of the second dopant material 1 It is preferable that (D2) and satisfy the relationship shown in the following formula (Equation 4). 1 (H2) > S 1 (D2) ... (Math 4)
[0181] In the organic EL element according to this embodiment, the second dopant material and the second host material satisfy the relationship shown in equation (Equation 4). As a result, the singlet energy of the second dopant material is smaller than the singlet energy of the second host material. Therefore, singlet excitons generated by the TTF phenomenon transfer energy from the second host material to the second dopant material, contributing to the fluorescence emission of the second dopant material.
[0182] In the organic EL element according to this embodiment, the second dopant material is preferably contained in the second light-emitting layer in an amount exceeding 1.1% by mass. That is, the second light-emitting layer preferably contains the second dopant material in an amount exceeding 1.1% by mass of the total mass of the second light-emitting layer, more preferably 1.2% by mass or more of the total mass of the second light-emitting layer, even more preferably 1.5% by mass or more of the total mass of the second light-emitting layer, and even more preferably 2% by mass or more of the total mass of the second light-emitting layer. The second light-emitting layer preferably contains the second dopant material in an amount of 10% by mass or less of the total mass of the second light-emitting layer, more preferably 7% by mass or less of the total mass of the second light-emitting layer, and even more preferably 5% by mass or less of the total mass of the second light-emitting layer.
[0183] In the organic EL element according to this embodiment, the second light-emitting layer preferably contains the second compound as the second host material in an amount of 60% by mass or more of the total mass of the second light-emitting layer, more preferably 70% by mass or more of the total mass of the second light-emitting layer, even more preferably 80% by mass or more of the total mass of the second light-emitting layer, even more preferably 90% by mass or more of the total mass of the second light-emitting layer, and still more preferably 95% by mass or more of the total mass of the second light-emitting layer. The second light-emitting layer preferably contains the second host material in an amount of 99% by mass or less of the total mass of the second light-emitting layer, more preferably 98.8% by mass or less of the total mass of the second light-emitting layer, and even more preferably 98% by mass or less of the total mass of the second light-emitting layer. However, if the second light-emitting layer contains the second host material and the second dopant material, the upper limit of the total content of the second host material and the second dopant material is 100% by mass.
[0184] This embodiment does not exclude the possibility that the second light-emitting layer may contain materials other than the second host material and the second dopant material. The second light-emitting layer may contain only one type of second host material, or two or more types. The second light-emitting layer may contain only one type of second dopant material, or two or more types.
[0185] In the organic EL element according to this embodiment, the film thickness of the second light-emitting layer is preferably 5 nm or more, more preferably 10 nm or more, and even more preferably 15 nm or more. If the film thickness of the second light-emitting layer is 5 nm or more, it is easier to suppress triplet excitons that have moved from the first light-emitting layer to the second light-emitting layer from returning to the first light-emitting layer. Also, if the film thickness of the second light-emitting layer is 5 nm or more, triplet excitons can be completely separated from the recombination portion in the first light-emitting layer. In the organic EL element according to this embodiment, the film thickness of the second light-emitting layer is preferably 30 nm or less, more preferably 28 nm or less, and even more preferably 25 nm or less. If the film thickness of the second light-emitting layer is 30 nm or less, the density of triplet excitons in the second light-emitting layer can be increased, making the TTF phenomenon even more likely to occur. In the organic EL element according to this embodiment, the film thickness of the second light-emitting layer is preferably 5 nm or more and 30 nm or less.
[0186] In the organic EL element according to this embodiment, it is also preferable that the thickness of the second light-emitting layer is greater than the thickness of the first light-emitting layer.
[0187] (First Dopant Material and Second Dopant Material) In the organic EL element according to this embodiment, the first dopant material and the second dopant material are not particularly limited as long as they are compounds that satisfy the relationship of formula (Equation 2C). In the organic EL element according to this embodiment, one embodiment of the first dopant material and the second dopant material is a compound containing one or more boron atoms, independently. One embodiment of the first dopant material and the second dopant material is a compound containing one or more and five or less boron atoms, a compound containing one or more and three or less boron atoms, a compound containing one or two boron atoms, or a compound containing one boron atom. In the organic EL element according to this embodiment, as the first dopant material and the second dopant material, for example, compounds that satisfy the relationship of formula (Equation 2C) can be selected and used from compounds containing one or more boron atoms and compounds selected from the group of polycyclic aromatic compounds represented by the following formula (DX). In the organic EL element according to this embodiment, the first dopant material and the second dopant material are each independently selected from the group of polycyclic aromatic compounds represented by the following formula (DX).
[0188]
[0189] (In the above formula (DX), ring a, ring b, and ring c are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle having 5 to 50 ring-forming atoms, Y 1 These are boron atoms, phosphorus atoms, P=O, P=S, aluminum atoms, gallium atoms, arsenic atoms, Si-R 40 , or Ge-R 42 And R 40 and R 42 Each of these is independently a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group, X 1 and X 2 These are, independently, an oxygen atom and N-R41 , a sulfur atom or a selenium atom, R 41 R either bonds with ring a, ring b, or ring c to form a substituted or unsubstituted monoring, or bonds with ring a, ring b, or ring c to form a substituted or unsubstituted condensed ring, or does not bond with ring a, ring b, and ring c, does not form a substituted or unsubstituted monoring, and does not form a substituted or unsubstituted condensed ring. 41 These are substituted or unsubstituted C1-C50 alkyl groups, substituted or unsubstituted C2-C50 alkenyl groups, substituted or unsubstituted C2-C50 alkynyl groups, substituted or unsubstituted ring-forming C3-C50 cycloalkyl groups, substituted or unsubstituted ring-forming C6-C50 aryl groups, or substituted or unsubstituted ring-forming heterocyclic groups with 5-50 atoms, and multiple R 41 They are either identical or different to one another.
[0190] In the organic EL element according to this embodiment, Y in formula (DX) 1 It is preferable that it is a boron atom.
[0191] In the organic EL element according to this embodiment, X in formula (DX) 1 and X 2 Both are NR 41 If so, at least one R 41 Preferably, the group is represented by the following formula (Ar-1).
[0192]
[0193] (In the above formula (Ar-1), B 1 The rings a, b, or c are connected to each other by a linking group L A They are bonded via a single bond, or they are bonded to each other via single bonds with ring a, ring b, or ring c, or they are not bonded to each other with ring a, ring b, and ring c, B 1 R A It combines with R to form a substituted or unsubstituted monoring, or A It combines with R to form a substituted or unsubstituted fused ring or AIt does not bond with, and does not bond with ring a, ring b and ring c, and R A B does not combine with 1 R is a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, a substituted or unsubstituted ring-forming C6-C50 aryloxy group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group. A , R B , R C , and R D R consists of two or more adjacent groups of which either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine to form a substituted or unsubstituted monoring and do not form a substituted or unsubstituted fused ring. A , R B , R C , and R D Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, a substituted or unsubstituted ring-forming C6-C50 aryloxy group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group, where * indicates a bond site with the N atom.) (Linking group L) A is, >C(-R F ) 2 , >O, >S, or >CO, and the aforementioned >C(-R F ) 2 The two R's FR is either bonded to each other to form a substituted or unsubstituted monoring, or bonded to each other to form a substituted or unsubstituted fused ring, or does not bond to each other, does not form the substituted or unsubstituted monoring, and does not form the substituted or unsubstituted fused ring. F Each of these is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms.
[0194] In the organic EL element according to this embodiment, B in formula (Ar-1) 1 , R B and R D However, each is preferably independently a substituted or unsubstituted C1-C50 alkyl group or a substituted or unsubstituted ring-forming C6-C50 aryl group, more preferably a substituted or unsubstituted C1-C30 alkyl group or a substituted or unsubstituted ring-forming C6-C30 aryl group, even more preferably a substituted or unsubstituted C1-C10 alkyl group or a substituted or unsubstituted ring-forming C6-C18 aryl group, and still more preferably a substituted or unsubstituted C1-C6 alkyl group or a substituted or unsubstituted ring-forming C6-C12 aryl group.
[0195] In the organic EL element according to this embodiment, B in formula (Ar-1) 1 and R B However, each is preferably independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, more preferably a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, even more preferably a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, and still more preferably a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms.
[0196] In the organic EL element according to this embodiment, B in formula (Ar-1) 1 and R BHowever, each is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, more preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, even more preferably a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and still more preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.
[0197] In the organic EL element according to this embodiment, B in formula (Ar-1) 1 and R B However, it is also preferable that they be the same group.
[0198] In the organic EL element according to this embodiment, B in formula (Ar-1) 1 and R B However, it is also preferable that the groups be different.
[0199] In the organic EL element according to this embodiment, B in formula (Ar-1) 1 and R D However, it is also preferable that they be the same group.
[0200] In the organic EL element according to this embodiment, B in formula (Ar-1) 1 and R D However, it is the same group, R B B 1 and R D It is also preferable that the group be different from the one mentioned above.
[0201] In the organic EL element according to this embodiment, R in formula (Ar-1) A and R C However, it is also preferable that the atom be a hydrogen atom.
[0202] In the organic EL element according to this embodiment, R in formula (Ar-1) A , R C , and R D However, it is also preferable that the atom be a hydrogen atom.
[0203] In the organic EL element according to this embodiment, it is preferable that the first dopant material and the second dopant material are each independently compounds represented by the following formulas (D-a), (D-b), (D-c), (D-d), (D-e), (D-f), (D-g), (D-h), (D-i), (D-j), or (D-k).
[0204]
[0205]
[0206]
[0207]
[0208]
[0209]
[0210]
[0211] (In the above formulas (D-a) to (D-k), R a1 ~R a3 , R b1 ~R b4 , R x1 , R x2 , R c1 ~R c4 , R g1 ~R g5 , R m1 ~R m4 and R k1 ~R k3 R consists of two or more adjacent groups of which either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine to form a substituted or unsubstituted monoring and do not form a substituted or unsubstituted fused ring. a1 ~R a3 , R b1 ~R b4 , R c1 ~R c4 , R g1 ~R g5 , R m1 ~R m4 and R k1 ~Rk3 Each of these independently consists of a hydrogen atom, a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group with 5 to 50 carbon atoms, a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming cycloalkyl group with 3 to 50 carbon atoms, and -Si(R 301 ) (Caution 302 ) (Caution 303 A group represented by ) -O-(R 304 A group represented by ) -S-(R 305 A group represented by ) -N(R 306 ) (Caution 307 A group represented by ) -B(R 308 ) (Caution 309 A group represented by ), a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a cyano group, or a halogen atom, which does not form the substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring. x1 and R x2 Each of these independently consists of a hydrogen atom, a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group with 5 to 50 carbon atoms, a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming cycloalkyl group with 3 to 50 carbon atoms, and -Si(R 301 ) (Caution 302 ) (Caution 303 A group represented by ) -O-(R 304 A group represented by ) -S-(R 305 A group represented by ) -B(R 308 ) (Caution 309 A group represented by ), a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a cyano group, or a halogen atom, Ar 1 Ar 2 and Ar 3 Each of these independently represents R in the above formula (DX). 41 This is synonymous with Z 1 , >O, >N-R NZ , >C(-R CZ ) 2, >Si(-R IZ ) 2 , >S, or >Se, and multiple Z 1 They are either identical or different from each other, >C(-R CZ ) 2 The two R's CZ They either bond to each other to form a substituted or unsubstituted monoring, or bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other, >Si(-R IZ ) 2 The two R's IZ They either bond to each other to form a substituted or unsubstituted monoring, or bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other, R NZ , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring CZ and R IZ Each of these is independently a hydrogen atom, a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, and ring f is a substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming aliphatic hydrocarbon ring having 5 to 50 carbon atoms, Y 1 is a single bond or a linking group, Y 2 is a single bond or a linking group, Y 3 is a single bond or linking group, m is 0 or 1, n is 0 or 1, p is 0 or 1, the sum of n and p is 0 or 1, and when m is 0, -(Y 1 ) 0 - is not a single bond or linking group connecting ring f and ring b, but when n is 0, -(Y 2 ) 0 - is not a single bond or linking group connecting ring k and ring c, but when p is 0, -(Y 3 ) 0 - is not a single bond or linking group connecting ring k and ring a, but rather a linking group Y1 , Y 2 and Y 3 These are, independently, >C(-R Y ) 2 , >O, >S, or >CO, and the aforementioned >C(-R Y ) 2 The two R's Y R is either bonded to each other to form a substituted or unsubstituted monoring, or bonded to each other to form a substituted or unsubstituted fused ring, or does not bond to each other, does not form the substituted or unsubstituted monoring, and does not form the substituted or unsubstituted fused ring. Y Each of these independently consists of a hydrogen atom, a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group with 5 to 50 carbon atoms, a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming cycloalkyl group with 3 to 50 carbon atoms, and -Si(R 301 ) (Caution 302 ) (Caution 303 A group represented by ) -O-(R 304 A group represented by ) -S-(R 305 A group represented by ) -N(R 306 ) (Caution 307 A group represented by ) -B(R 308 ) (Caution 309 A group represented by ), a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a cyano group, or a halogen atom, wherein at least one aromatic hydrocarbon ring or heterocycle in each of the formulas (D-a) to (D-k) may be condensed with at least one cycloalkane, and the cycloalkane may be substituted with at least one substituent, and at least one -CH in the cycloalkane 2 - may be replaced with -O-, and at least one hydrogen atom in each of the formulas (D-a) to (D-k) may be replaced with a halogen atom.) (In the first dopant material, R 306 and R 307 The set consisting of these elements is linked to each other by a linking base L NThey are bonded via R, or bonded to each other via single bonds, or not bonded to each other at all. 308 and R 309 The set consisting of these elements is linked to each other by a linking base L B They are bonded via R, or bonded to each other via single bonds, or not bonded to each other at all. 301 ~R 305 , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring 306 ~R 309 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group, and R 301 If multiple R 301 They are either identical or different from each other, R 302 If multiple R 302 They are either identical or different from each other, R 303 If multiple R 303 They are either identical or different from each other, R 304 If multiple R 304 They are either identical or different from each other, R 305 If multiple R 305 They are either identical or different from each other, R 306 If multiple R 306 They are either identical or different from each other, R 307 If multiple R 307 They are either identical or different from each other, R 308 If multiple R 308 They are either identical or different from each other, R 309 If multiple R 309 They are either identical or different from each other.) (Connecting base L) N and linking base L B These are, independently, >C(-R F )2 , >O, >S, or >CO, and the aforementioned >C(-R F ) 2 The two R's F R is either bonded to each other to form a substituted or unsubstituted monoring, or bonded to each other to form a substituted or unsubstituted fused ring, or does not bond to each other, does not form the substituted or unsubstituted monoring, and does not form the substituted or unsubstituted fused ring. F Each of these is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms.
[0212] When at least one aromatic hydrocarbon ring or heterocycle in each of the formulas (D-a) to (D-f) is condensed with at least one cycloalkane, at least one substituent of the cycloalkane is independently: a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, or -Si(R 301 ) (Caution 302 ) (Caution 303 A group represented by ) -O-(R 304 A group represented by ) -S-(R 305 A group represented by ) -N(R 306 ) (Caution 307 A group represented by ) -B(R 308 ) (Caution 309 The group is preferably represented by ), a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a cyano group, or a halogen atom.
[0213] In the organic EL element according to this embodiment, Ar in formula (D-a) 1 This is equation (Ar-1), and in equation (Ar-1) B 1However, an example of a compound in which ring b is bonded to each other via a single bond is represented by the following formula (D-aa). In the organic EL element according to this embodiment, Ar in formula (D-a) 1 This is equation (Ar-1), and in equation (Ar-1) B 1 However, an example of a compound in which ring a and other rings are bonded via single bonds is represented by the following formula (D-ab).
[0214]
[0215] (In the above formula (D-aa) or formula (D-ab), R a1 ~R a3 , R b1 ~R b4 , R x1 , R x2 , and R c1 ~R c4 These are, respectively, R in the above formula (D-a). a1 ~R a3 , R b1 ~R b4 , R x1 , R x2 , and R c1 ~R c4 This is synonymous with R A , R B , R C , and R D R in the above formula (Ar-1) is A , R B , R C , and R D (This is synonymous with...)
[0216] In the organic EL element according to this embodiment, it is also preferable that either the first dopant material or the second dopant material is a compound represented by formula (D-aa) or formula (D-ab).
[0217] In the organic EL element according to this embodiment, it is preferable that either the first dopant material or the second dopant material is a compound represented by the following formulas (D-a1), (D-a2), (D-a3), (D-a4), (D-a5), (D-a6), (D-a7), (D-b1), (D-b2), (D-b3), (D-c1), (D-c2), (D-c3), (D-c4), (D-d1), (D-d2), (D-d3), or (D-d4).
[0218]
[0219]
[0220]
[0221]
[0222] (In the above formulas (D-a1) to (D-a7), R a1 ~R a3 , R b1 ~R b4 and R c1 ~R c4 These are, respectively, R in the above formula (D-a). a1 ~R a3 , R b1 ~R b4 and R c1 ~R c4 This is synonymous with R x1 and R x2 These are, respectively, R in the above formula (D-a). x1 and R x2 This is synonymous with R d1 ~R d4 and R e1 ~R e5 R consists of two or more adjacent groups of which either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine to form a substituted or unsubstituted monoring and do not form a substituted or unsubstituted fused ring. d1 ~R d4 and R e1 ~R e5Each of these independently consists of a hydrogen atom, a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group with 5 to 50 carbon atoms, a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming cycloalkyl group with 3 to 50 carbon atoms, and -Si(R 301 ) (Caution 302 ) (Caution 303 A group represented by ) -O-(R 304 A group represented by ) -S-(R 305 A group represented by ) -N(R 306 ) (Caution 307 A group represented by ) -B(R 308 ) (Caution 309 The group represented by ) is a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a cyano group, or a halogen atom, where Me represents a methyl group.
[0223]
[0224]
[0225] (In the above formulas (D-b1) to (D-b3), R a1 ~R a3 , R b1 ~R b4 , R c1 ~R c4 , R x1 Ar 1 and Ar 2 These are, respectively, R in the above formula (D-b). a1 ~R a3 , R b1 ~R b4 , R c1 ~R c4 , R x1 Ar 1 and Ar 2 (This is synonymous with...)
[0226]
[0227]
[0228]
[0229]
[0230] (In the above formulas (D-c1) to (D-c4), R a1 ~R a3 , R b1 ~R b4 , R c1 ~R c4 , R g1 ~R g5 Ar 1 , and Ar 2 These are, respectively, R in the above formula (D-c). a1 ~R a3 , R b1 ~R b4 , R c1 ~R c4 , R g1 ~R g5 Ar 1 , and Ar 2 This is synonymous with Z 1 is >S, >O, or >C(-CH 3 ) 2 And R h1 ~R h8 R consists of two or more adjacent groups of which either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine to form a substituted or unsubstituted monoring and do not form a substituted or unsubstituted fused ring. h1 ~R h8 Each of these independently consists of a hydrogen atom, a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group with 5 to 50 carbon atoms, a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming cycloalkyl group with 3 to 50 carbon atoms, and -Si(R 301 ) (Caution 302 ) (Caution 303 A group represented by ) -O-(R 304 A group represented by ) -S-(R 305 A group represented by ) -N(R 306 ) (Caution 307 A group represented by ) -B(R 308 ) (Caution 309(These are groups represented by ), substituted or unsubstituted alkenyl groups, cyano groups, or halogen atoms having 2 to 50 carbon atoms.)
[0231]
[0232]
[0233]
[0234]
[0235] (In the above formulas (D-d1) to (D-d4), R a1 ~R a3 , R b1 ~R b4 , R c1 ~R c4 , R g1 ~R g5 Ar 1 , and Ar 2 Each of these independently corresponds to R in the above formula (D-d). a1 ~R a3 , R b1 ~R b4 , R c1 ~R c4 , R g1 ~R g5 Ar 1 , and Ar 2 This is synonymous with R h1 ~R h8 R consists of two or more adjacent groups of which either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine to form a substituted or unsubstituted monoring and do not form a substituted or unsubstituted fused ring. h1 ~R h8 Each of these independently consists of a hydrogen atom, a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group with 5 to 50 carbon atoms, a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming cycloalkyl group with 3 to 50 carbon atoms, and -Si(R 301 ) (Caution 302 ) (Caution 303A group represented by ) -O-(R 304 A group represented by ) -S-(R 305 A group represented by ) -N(R 306 ) (Caution 307 A group represented by ) -B(R 308 ) (Caution 309 (These are groups represented by ), substituted or unsubstituted alkenyl groups, cyano groups, or halogen atoms having 2 to 50 carbon atoms.)
[0236] The compound represented by formula (D-b1) is Z in formula (D-b). 1 This corresponds to the compound when >S. The compound represented by formula (D-b2) is Z in formula (D-b). 1 This corresponds to the compound when > O. The compound represented by formula (D-b3) is Z in formula (D-b). 1 > C(-R CZ ) 2 and two R CZ This corresponds to a compound where the group is a methyl group.
[0237] The compound represented by the above formula (D-c1) is one in which m in the above formula (D-c) is 0, and -(Y 1 ) 0 This corresponds to an example of a compound where - is not a single bond or linking group connecting ring f and ring b. In the case where m in formula (D-c) is 0, as in the compound represented by formula (D-c1), Y 1 There is no bond between ring f and ring b via . The compound represented by formula (D-c2) or (D-c4) is one in which m in formula (D-c) is 1, Y 1 This corresponds to an example of a compound in which there is a single bond. The compound represented by the above formula (D-c3) is one in which m in the above formula (D-c) is 1, Y 1 > C(-R Y ) 2 This corresponds to the compound in the case of [this condition].
[0238] The compound represented by the formula (D-d1) is one in which m in the formula (D-d) is 0, and -(Y 1 ) 0This corresponds to an example of a compound where - is not a single bond or linking group connecting ring f and ring b. In the case where m in formula (D-d) is 0, as in the compound represented by formula (D-d1), Y 1 There is no bond between ring f and ring b via . The compound represented by formula (D-d2) or (D-d4) is one in which m in formula (D-d) is 1, Y 1 This corresponds to an example of a compound in which there is a single bond. The compound represented by the formula (D-d3) is one in which m in the formula (D-d) is 1, and Y 1 > C(-R Y ) 2 This corresponds to the compound in the case of [this condition].
[0239] (Formula (D-a1), Formula (D-a2), Formula (D-a3), Formula (D-a4), Formula (D-a5), Formula (D-a6), Formula (D-a7), Formula (D-b1), Formula (D-b2), Formula (D-b3), formula (D-c1), formula (D-c2), formula (D-c3), formula (D-c4), formula (D-d1), formula (D-d2), formula (D-d3), or formula (D-d4), R a1 ~R a3 , R b1 ~R b4 , R x1 , R x2 , R c1 ~R c4 and R g1 ~R g5 R consists of two or more adjacent groups of which either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine to form a substituted or unsubstituted monoring and do not form a substituted or unsubstituted fused ring. a1 ~R a3 , R b1 ~R b4 , R c1 ~R c4 and R g1 ~R g5Each of these independently consists of a hydrogen atom, a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group with 5 to 50 carbon atoms, a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming cycloalkyl group with 3 to 50 carbon atoms, and -Si(R 301 ) (Caution 302 ) (Caution 303 A group represented by ) -O-(R 304 A group represented by ) -S-(R 305 A group represented by ) -N(R 306 ) (Caution 307 A group represented by ) -B(R 308 ) (Caution 309 A group represented by ), a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a cyano group, or a halogen atom, which does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted fused ring. x1 and R x2 Each of these independently consists of a hydrogen atom, a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group with 5 to 50 carbon atoms, a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming cycloalkyl group with 3 to 50 carbon atoms, and -Si(R 301 ) (Caution 302 ) (Caution 303 A group represented by ) -O-(R 304 A group represented by ) -S-(R 305 A group represented by ) -B(R 308 ) (Caution 309 A group represented by ), a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a cyano group, or a halogen atom, where Me represents a methyl group, and R d1 ~R d4 and R e1 ~R e5R consists of two or more adjacent groups of which either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine to form a substituted or unsubstituted monoring and do not form a substituted or unsubstituted fused ring. d1 ~R d4 and R e1 ~R e5 Each of these independently consists of a hydrogen atom, a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group with 5 to 50 carbon atoms, a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming cycloalkyl group with 3 to 50 carbon atoms, and -Si(R 301 ) (Caution 302 ) (Caution 303 A group represented by ) -O-(R 304 A group represented by ) -S-(R 305 A group represented by ) -N(R 306 ) (Caution 307 A group represented by ) -B(R 308 ) (Caution 309 A group represented by ), a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a cyano group, or a halogen atom, Z 1 is >S, >O, or >C(-CH 3 ) 2 And R h1 ~R h8 R consists of two or more adjacent groups of which either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine to form a substituted or unsubstituted monoring and do not form a substituted or unsubstituted fused ring. h1 ~R h8Each of these independently consists of a hydrogen atom, a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group with 5 to 50 carbon atoms, a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming cycloalkyl group with 3 to 50 carbon atoms, and -Si(R 301 ) (Caution 302 ) (Caution 303 A group represented by ) -O-(R 304 A group represented by ) -S-(R 305 A group represented by ) -N(R 306 ) (Caution 307 A group represented by ) -B(R 308 ) (Caution 309 A group represented by ), a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a cyano group, or a halogen atom, Ar 1 and Ar 2 Each of these is independently a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, a substituted or unsubstituted ring-forming C5-C50 heterocyclic group, or a group represented by the formula (Ar-1), Ar 1 and Ar 2 At least one of them is a group represented by the formula (Ar-1), and in the formula (Ar-1), B 1 R a1 , R b1 , R a3 or R c4 It combines with R to form a substituted or unsubstituted monoring, or a1 , R b1 , R a3 or R c4 It combines with R to form a substituted or unsubstituted fused ring, or a1 , R b1 , R a3 and R c4 B does not combine with 1 RA It combines with R to form a substituted or unsubstituted monoring, or A It combines with R to form a substituted or unsubstituted fused ring, or A It does not bind with R a1 , R b1 , R a3 and R c4 It does not bind with R A B does not combine with 1 R is a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, a substituted or unsubstituted ring-forming C6-C50 aryloxy group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group. A , R B , R C , and R D R consists of two or more adjacent groups of which either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine to form a substituted or unsubstituted monoring and do not form a substituted or unsubstituted fused ring. A , R B , R C , and R D Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, a substituted or unsubstituted ring-forming C6-C50 aryloxy group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group, where * indicates a bond site with the N atom.
[0240] In the organic EL element according to this embodiment, it is also preferable that either the first dopant material or the second dopant material is a compound represented by formula (D-a1), formula (D-a2), formula (D-a3), formula (D-a4), formula (D-a5), formula (D-a6), or formula (D-a7).
[0241] In the organic EL element according to this embodiment, it is also preferable that either the first dopant material or the second dopant material is a compound represented by formula (D-b1), formula (D-b2), or formula (D-b3).
[0242] In the organic EL element according to this embodiment, it is also preferable that either the first dopant material or the second dopant material is a compound represented by formula (D-c1), formula (D-c2), formula (D-c3), or formula (D-c4).
[0243] In the organic EL element according to this embodiment, it is also preferable that either the first dopant material or the second dopant material is a compound represented by formula (D-d1), formula (D-d2), formula (D-d3), or formula (D-d4).
[0244] In the organic EL element according to this embodiment, the first dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-a1) to (D-a7), and the second dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-a1) to (D-a7), or the first dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-a1) to (D-a7), and the second dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-b1) to (D-b3), or the first dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-a1) to (D-a7), and the second dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-c1) to (D-c4), It is also preferable that the first dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-a1) to (D-a7), and the second dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-d1) to (D-d4), or that the first dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-a1) to (D-a7), and the second dopant material is a compound represented by formula (D-e) or formula (D-f).
[0245] In the organic EL element according to this embodiment, the first dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-b1) to (D-b3), and the second dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-a1) to (D-a7), or the first dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-b1) to (D-b3), and the second dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-b1) to (D-b3), or the first dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-b1) to (D-b3), and the second dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-c1) to (D-c4), It is also preferable that the first dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-b1) to (D-b3), and the second dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-d1) to (D-d4), or that the first dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-b1) to (D-b3), and the second dopant material is a compound represented by formula (D-e) or formula (D-f).
[0246] In the organic EL element according to this embodiment, the first dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-c1) to (D-c4), and the second dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-a1) to (D-a7), or the first dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-c1) to (D-c4), and the second dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-b1) to (D-b3), or the first dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-c1) to (D-c4), and the second dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-c1) to (D-c4), It is also preferable that the first dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-c1) to (D-c4), and the second dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-d1) to (D-d4), or that the first dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-c1) to (D-c4), and the second dopant material is a compound represented by formula (D-e) or formula (D-f).
[0247] In the organic EL element according to this embodiment, the first dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-d1) to (D-d4), and the second dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-a1) to (D-a7), or the first dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-d1) to (D-d4), and the second dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-b1) to (D-b3), or the first dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-d1) to (D-d4), and the second dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-c1) to (D-c4), It is also preferable that the first dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-d1) to (D-d4), and the second dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-d1) to (D-d4), or that the first dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-d1) to (D-d4), and the second dopant material is a compound represented by formula (D-e) or formula (D-f).
[0248] In the organic EL element according to this embodiment, the first dopant material is a compound represented by formula (D-e) or formula (D-f), and the second dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-a1) to (D-a7), or the first dopant material is a compound represented by formula (D-e) or formula (D-f), and the second dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-b1) to (D-b3), or the first dopant material is a compound represented by formula (D-e) or formula (D-f), and the second dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-c1) to (D-c4), or the first dopant material is a compound represented by formula (D-e) or formula (D-f), and the second dopant material is a compound represented by any one formula selected from the group consisting of formulas (D-d1) to (D-d4), It is also preferable that the first dopant material is a compound represented by formula (D-e) or formula (D-f), and the second dopant material is a compound represented by formula (D-e) or formula (D-f).
[0249] In the organic EL element according to this embodiment, the first dopant material is also preferably a compound that does not contain an azine ring structure in its molecule.
[0250] In the organic EL element according to this embodiment, the first dopant material is preferably not a boron-containing complex, and more preferably not a complex.
[0251] In the organic EL element according to this embodiment, the second dopant material is also preferably a compound that does not contain an azine ring structure in its molecule.
[0252] In the organic EL element according to this embodiment, the second dopant material is preferably not a boron-containing complex, and more preferably not a complex.
[0253] In the organic EL element according to this embodiment, -O-(R 304 R in the group represented by ) 304It is also preferable that this is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.
[0254] In the organic EL element according to this embodiment, -S-(R 305 R in the group represented by ) 305 It is also preferable that this is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.
[0255] In the organic EL element according to this embodiment, -N(R 306 ) (Caution 307 R in the group represented by ) 306 and R 307 These may each be independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
[0256] In the organic EL element according to this embodiment, -B(R 308 ) (Caution 309 R in the group represented by ) 308 and R 309 It is also preferable that each of these groups independently be a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.
[0257] In the organic EL element according to this embodiment, the substituents in the first dopant material and the second dopant material, when referred to as "substituted or unsubstituted," are preferably unsubstituted C1-C18 alkyl groups, unsubstituted ring-forming C3-C18 cycloalkyl groups, unsubstituted ring-forming C6-C18 aryl groups, or unsubstituted ring-forming C5-C18 heterocyclic groups.
[0258] In the organic EL element according to this embodiment, it is also preferable that the substituents in the first dopant material and the second dopant material, when referred to as "substituted or unsubstituted," are unsubstituted C1-C6 alkyl groups, unsubstituted ring-forming C3-C10 cycloalkyl groups, unsubstituted ring-forming C6-C12 aryl groups, or unsubstituted ring-forming C5-C13 heterocyclic groups.
[0259] In the organic EL element according to this embodiment, it is also preferable that the groups described as "substituted or unsubstituted" in the first dopant material and the second dopant material are both "unsubstituted" groups.
[0260] In the organic EL element according to this embodiment, the first dopant material is preferably a compound that exhibits light emission with a maximum peak wavelength of 430 nm or more and 480 nm or less.
[0261] In the organic EL element according to this embodiment, the first dopant material is preferably a compound that exhibits light emission with a maximum peak wavelength of 475 nm or less.
[0262] In the organic EL element according to this embodiment, the first dopant material is preferably a compound that exhibits light emission with a maximum peak wavelength of 440 nm or higher.
[0263] In the organic EL element according to this embodiment, the first dopant material is preferably a fluorescent compound.
[0264] In the organic EL element according to this embodiment, the second dopant material is preferably a compound that exhibits light emission with a maximum peak wavelength of 430 nm or more and 480 nm or less.
[0265] In the organic EL element according to this embodiment, the second dopant material is preferably a compound that exhibits light emission with a maximum peak wavelength of 475 nm or less.
[0266] In the organic EL element according to this embodiment, the second dopant material is preferably a compound that exhibits light emission with a maximum peak wavelength of 440 nm or higher.
[0267] In the organic EL element according to this embodiment, the second dopant material is preferably a fluorescent compound.
[0268] (Maximum Peak Wavelength) The maximum peak wavelength of the compounds described herein can be determined by measuring the PL spectrum of a film containing the compound to be measured. The specific method for measuring the maximum peak wavelength is as follows: A dopant material (the compound to be measured for the maximum peak wavelength) and a host material are co-deposited onto a quartz substrate (25 × 25 mm) so that the mass-based ratio of the dopant material to the host material contained in the light-emitting layer (dopant material / host material) is the same, and a film for measurement with a thickness of 50 nm is formed. Next, the quartz substrate on which the film for measurement is formed and a sealing glass coated with a desiccant are joined using an ultraviolet-curing resin to seal the film for measurement. The outer dimensions of the sealing glass are 17 × 17 mm, the inner dimensions are 13 × 13 mm, and the recess depth is 0.5 mm. As the desiccant, for example, OleDry-P2 manufactured by Futaba Corporation can be used. As the UV-curing resin, for example, TB3124N (IE) manufactured by ThreeBond Fine Chemicals, Inc. can be used. A fluorescence spectrum analyzer is used for PL spectrum measurement. The measurement conditions are as follows: The maximum peak wavelength λ (unit: nm) of the film is calculated from the PL spectrum obtained by exciting the film sample with a specific wavelength (a value obtained by shortening the maximum peak wavelength of the absorption spectrum by 30 nm). The maximum peak wavelength obtained in this way is sometimes called the maximum peak wavelength of fluorescence emission (FL-peak). As the fluorescence spectrum analyzer, for example, a spectrofluorometer F-7000 (manufactured by Hitachi High-Tech Science Corporation) can be used. The maximum peak wavelength of the absorption spectrum used to determine the wavelength of light that excites the film sample is the singlet energy S using the solution described above. 1 This can be measured using a solution method. In this solution method, a toluene solution of the compound to be measured (dopant material) is prepared, and the absorption spectrum of the toluene solution is measured.
[0269] The method for measuring the maximum peak wavelength of a compound is as follows: First, the compound to be measured is divided into 10 sections. -6 mol / L or more 10 -5A toluene solution (sample for measurement) is prepared by dissolving the compound in toluene at a concentration of mol / L or less. Next, this toluene solution is 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 maximum peak wavelength of the compound is the peak wavelength of the emission spectrum at which the emission intensity is maximum in the measured emission spectrum. The emission spectrum can be measured using a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measuring device is not limited to the device used here.
[0270] (Method for producing the first and second dopant materials) The first and second dopant materials can be produced by known methods. Alternatively, the first and second dopant materials can also be produced by following known methods and using known alternative reactions and raw materials suited to the target product.
[0271] (Specific examples of the first and second dopant materials) Examples of the first and second dopant materials include the following compounds. However, the present invention is not limited to these specific examples of the first and second dopant materials.
[0272]
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[0332] (First host material and second host material) In the organic EL element according to this embodiment, the first host material and the second host material are not particularly limited as long as they are compounds that satisfy the relationship in formula (Equation 1). In one embodiment of the organic EL element according to this embodiment, the first host material is a compound that does not contain an anthracene structure with 14 ring-forming carbon atoms. "Does not contain an anthracene structure with 14 ring-forming carbon atoms" means that the molecular structure of the compound does not contain the "anthracene structure with 14 ring-forming carbon atoms" itself. For example, the benzanthracene structure has a structure in which one more benzene ring is condensed onto the anthracene structure, but the benzanthracene structure has 18 ring-forming carbon atoms and is not the "anthracene structure with 14 ring-forming carbon atoms" itself. Furthermore, for example, the naphthacene structure has a structure in which one more benzene ring is fused to the anthracene structure, and the pentacene structure has a structure in which two more benzene rings are fused to the anthracene structure (or a structure in which one naphthalene ring is fused to the anthracene structure). However, the naphthacene structure has 18 ring-forming carbon atoms, and the pentacene structure has 22 ring-forming carbon atoms, and neither is the "anthracene structure with 14 ring-forming carbon atoms" itself. Thus, any structure in which one or more rings are fused to the anthracene structure does not qualify as the "anthracene structure with 14 ring-forming carbon atoms."
[0333] In one embodiment of the organic EL element according to this embodiment, the second host material is a compound containing an anthracene structure with 14 ring-forming carbon atoms. "Containing an anthracene structure with 14 ring-forming carbon atoms" means that the molecular structure of the compound contains the "anthracene structure with 14 ring-forming carbon atoms" itself. Therefore, for example, even if the second host material has only a structure in which one or more rings are condensed on an anthracene structure as a ring structure, it does not meet the condition of "containing an anthracene structure with 14 ring-forming carbon atoms".
[0334] In one embodiment of the organic EL element according to this embodiment, the first host material is a compound containing an anthracene structure with 14 ring-forming carbon atoms. In one embodiment of the organic EL element according to this embodiment, the second host material is a compound that does not contain an anthracene structure with 14 ring-forming carbon atoms.
[0335] (First host material) In the organic EL element according to this embodiment, the first host material is a substituted or unsubstituted pyrene skeleton, a substituted or unsubstituted benzanthracene skeleton, a substituted or unsubstituted xanthene skeleton, a substituted or unsubstituted benzoxanthene skeleton, a substituted or unsubstituted chrysene skeleton, a substituted or unsubstituted benzochrysene skeleton, a substituted or unsubstituted fluorantene skeleton, a substituted or unsubstituted benzofluorantene skeleton, a substituted or unsubstituted triphenylene skeleton, a substituted or unsubstituted benzotriphenylene skeleton, a substituted or unsubstituted phenanthrene skeleton, a substituted or unsubstituted benzophenanthrene skeleton, a substituted or unsubstituted phenanthrofuran skeleton, a substituted or unsubstituted fluorene skeleton, a substituted or unsubstituted benzofluorene skeleton, a substituted or unsubstituted dibenzofuran skeleton, a substituted or unsubstituted naphthobenzofuran skeleton, a substituted or unsubstituted dinaphthofuran skeleton, a substituted or unsubstituted dibenzothiophene skeleton, It is also preferable to have one or more skeletons selected from the group consisting of substituted or unsubstituted naphthobenzothiophene skeletons, substituted or unsubstituted dinaphthothiophene skeletons, and substituted or unsubstituted indolocarbazole skeletons, and the first host material may have two or more of the same skeletons selected from the group.
[0336] In the organic EL element according to this embodiment, the first host material may also preferably have one or more skeletons selected from the group consisting of a substituted or unsubstituted pyrene skeleton, a substituted or unsubstituted benzanthracene skeleton, a substituted or unsubstituted benzoxanthene skeleton, a substituted or unsubstituted chrysene skeleton, a substituted or unsubstituted triphenylene skeleton, a substituted or unsubstituted benzotriphenylene skeleton, a substituted or unsubstituted phenanthrene skeleton, a substituted or unsubstituted phenanthrofuran skeleton, a substituted or unsubstituted fluorene skeleton, a substituted or unsubstituted benzofluorene skeleton, a substituted or unsubstituted dibenzofuran skeleton, a substituted or unsubstituted naphthobenzofuran skeleton, a substituted or unsubstituted dinaphthofuran skeleton, a substituted or unsubstituted dibenzothiophene skeleton, and a substituted or unsubstituted indolocarbazole skeleton, and the first host material may have two or more of the same type of skeletons selected from the group.
[0337] In the organic EL element according to this embodiment, the substituted or unsubstituted fluorene skeleton is preferably a 9,9-dimethylfluorene skeleton or a 9,9-diphenylfluorene skeleton, the substituted or unsubstituted benzoxanthene skeleton is preferably a substituted or unsubstituted benzo[kl]xanthene skeleton, the substituted or unsubstituted phenanthrofuran skeleton is preferably a substituted or unsubstituted phenanthrofuran skeleton, and the substituted or unsubstituted indrocarbazole skeleton is preferably an indro[3,2,1-jk]carbazole skeleton.
[0338] In the organic EL element according to this embodiment, the first host material is preferably a compound represented by the following formula (H1-1) or formula (H1-2).
[0339] In the organic EL element according to this embodiment, the first host material is also preferably a compound represented by the following formula (H1-1).
[0340]
[0341] (In the above formula (H1-1), R 150 ~R 159Each of these independently consists of a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C1-C50 haloalkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -Si(R 901 ) (Caution 902 ) (Caution 903 A group represented by ) -O-(R 904 A group represented by ) -S-(R 905 A group represented by ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 The base represented by -COOR 802 A group represented by (H150), 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 above formula (H150), however R 150 ~R 159 At least one of the groups is a group represented by formula (H150), and if there are multiple groups represented by formula (H150), the multiple groups represented by formula (H150) are either identical or different from each other. 151 This 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, and Ar 151 is a substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 ring-forming atoms, mg is 0, 1, 2, 3, 4, or 5, and when mg is 0, -(L 151 ) 0 - represents a single bond, L 151 If there are two or more, then there are two or more L 151 They are either identical or different from each other, Ar 151 If there are two or more Ar 151 (These are either identical or different from each other, and * in formula (H150) indicates the bonding position.) (In the first host material, R901 ~R 905 , R 801 and R 802 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group, and R 901 If multiple R 901 They are either identical or different from each other, R 902 If multiple R 902 They are either identical or different from each other, R 903 If multiple R 903 They are either identical or different from each other, R 904 If multiple R 904 They are either identical or different from each other, R 905 If multiple R 905 They are either identical or different from each other, R 801 If multiple R 801 They are either identical or different from each other, R 802 If multiple R 802 (They are either identical or different to each other.)
[0342] In the above formula (H150), mg is preferably 0, 1, or 2, and more preferably 0 or 1. In the above formula (H150), L 151 It is preferably a substituted or unsubstituted ring-forming arylene group having 6 to 14 carbon atoms, and more preferably a substituted or unsubstituted ring-forming arylene group having 6 to 12 carbon atoms. In the above formula (H150), L 151 It is also preferable that Ar be a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group. In the above formula (H150), 151This includes substituted or unsubstituted anthryl groups, substituted or unsubstituted benzoantryl groups, substituted or unsubstituted phenanthryl groups, substituted or unsubstituted benzophenanthryl groups, substituted or unsubstituted phenalenyl groups, substituted or unsubstituted pyrenyl groups, substituted or unsubstituted crisenyl groups, substituted or unsubstituted benzocrisenyl groups, substituted or unsubstituted triphenylenyl groups, substituted or unsubstituted benzotriphenylenyl groups, substituted or unsubstituted tetracenyl groups, substituted or unsubstituted pentacenyl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted 9,9'-spirobifluorenyl groups, and substituted or unsubstituted groups. It is preferable that the group is a substituted benzofluorenyl group, a substituted or unsubstituted dibenzofluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted benzofluoranthenyl group, a substituted or unsubstituted perilenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted dinaphthofuranyl group, a substituted or unsubstituted benzoxanthenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted naphthobenzothiophenyl group, a substituted or unsubstituted dinaphthothiophenyl group, or a substituted or unsubstituted benzothioxanthenyl group. 151 It is more preferable that the group is a substituted or unsubstituted benzoanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted benzoxanthenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted naphthobenzothiophenyl group, or a substituted or unsubstituted benzothioxanthenyl group.
[0343] In the organic EL element according to this embodiment, the first host material is also preferably a compound represented by the following formula (H152).
[0344]
[0345] (In the above formula (H152), R 150 ~R 152 And R 154 ~R159 Each of these independently consists of a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C1-C50 haloalkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -Si(R 901 ) (Caution 902 ) (Caution 903 A group represented by ) -O-(R 904 A group represented by ) -S-(R 905 A group represented by ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 The base represented by -COOR 802 A group represented by , a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, X 15 L is an oxygen atom or a sulfur atom. 151 and mg are, respectively, L in formula (H150). 151 And is synonymous with mg, R 1500 ~R 1504 R consists of two or more adjacent groups of which either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine to form a substituted or unsubstituted monoring and do not form a substituted or unsubstituted fused ring. 1500 ~R 1504 Each of these independently consists of a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C1-C50 haloalkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -Si(R 901 ) (Caution 902 ) (Caution 903 A group represented by ) -O-(R904 A group represented by ) -S-(R 905 A group represented by ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 The base represented by -COOR 802 A group represented by , a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, and multiple R 1500 (These are either identical or different from each other.) (In the compound represented by the above formula (H152), R 901 ~R 905 , R 801 and R 802 These are, respectively, R in the above formula (H1-1). 901 ~R 905 , R 801 and R 802 (This is synonymous with...)
[0346] In the organic EL element according to this embodiment, the first host material is also preferably a compound represented by the following formula (H153) or formula (H154).
[0347]
[0348]
[0349] (In the above formula (H153) or formula (H154), R 150 ~R 152 and R 154 ~R 159 These are, respectively, R in the above formula (H1-1). 150 ~R 152 and R 154 ~R 159 It is synonymous with L 151 and mg are, respectively, L in formula (H150). 151 And is synonymous with mg, X 3 is an oxygen atom or a sulfur atom, R 1510 ~R 1517 , and R 1520 ~R 1526Each of these independently consists of a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C1-C50 haloalkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -Si(R 901 ) (Caution 902 ) (Caution 903 A group represented by ) -O-(R 904 A group represented by ) -S-(R 905 A group represented by ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 The base represented by -COOR 802 A group represented by , a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, and multiple R 1510 These are either identical or different from each other, and multiple R 1520 (These are either identical or different from each other.) (In the compound represented by formula (H153) or formula (H154), R 901 ~R 905 , R 801 and R 802 These are, respectively, R in the above formula (H1-1). 901 ~R 905 , R 801 and R 802 (This is synonymous with...)
[0350] In the organic EL element according to this embodiment, the first host material is also preferably a compound represented by the following formula (H1-2).
[0351]
[0352] (In the above formula (H1-2), R 131 ~R 140 Ar 131 and Ar 132Each of these independently consists of a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C1-C50 haloalkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -Si(R 901 ) (Caution 902 ) (Caution 903 A group represented by ) -O-(R 904 A group represented by ) -S-(R 905 A group represented by ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 The base represented by -COOR 802 A group represented by , a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, or a group represented by the above formula (H131), however R 131 ~R 140 Ar 131 and Ar 132 At least one of the groups is a group represented by formula (H131), and if there are multiple groups represented by formula (H131), the multiple groups represented by formula (H131) are either identical or different from each other. 13 This 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, and Ar 13 is a substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 ring-forming atoms, and mb is 0, 1, 2, 3, 4, or 5, and when mb is 0, -(L 13 ) 0 - represents a single bond, L 13 If there are two or more, then there are two or more L 13 They are either identical or different from each other, Ar 13 If there are two or more Ar 13(These are either identical or different from each other, and * in formula (H131) indicates the bonding position.) (In the first host material, R 901 ~R 905 , R 801 and R 802 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group, and R 901 If multiple R 901 They are either identical or different from each other, R 902 If multiple R 902 They are either identical or different from each other, R 903 If multiple R 903 They are either identical or different from each other, R 904 If multiple R 904 They are either identical or different from each other, R 905 If multiple R 905 They are either identical or different from each other, R 801 If multiple R 801 They are either identical or different from each other, R 802 If multiple R 802 (They are either identical or different to each other.)
[0353] In the organic EL element according to this embodiment, the first host material is also preferably a compound represented by the following formula (H132) or (H133).
[0354]
[0355] (In the above formulas (H132) and (H133), R 131 ~R 140 Ar 131 and Ar 132each independently represent 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, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms; and L 13 , Ar 13 and mb have the same definitions as L 13 , Ar 13 and mb in formula (H131), respectively.) (In the compound represented by formula (H132) and the compound represented by (H133), R 901 to R 905 , R 801 and R 802 have the same definitions as R 901 to R 905 , R 801 and R 802 in the compound represented by formula (H1-2), respectively.)
[0356] In the above formulas (H131), (H132) and (H133), mb is preferably 0, 1 or 2, and more preferably 0 or 1.
[0357] In the above formulas (H131), (H132) and (H133), it is also preferable that mb is 0.
[0358] In the above formulas (H131), (H132) and (H133), L 13It is preferably a substituted or unsubstituted ring-forming arylene group having 6 to 14 carbon atoms, and more preferably a substituted or unsubstituted ring-forming arylene group having 6 to 12 carbon atoms.
[0359] In the above formulas (H131), (H132), and (H133), L 13 It is also preferable that this is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.
[0360] In the above formulas (H131), (H132), and (H133), Ar 13 This includes substituted or unsubstituted benzoanthryl groups, substituted or unsubstituted phenanthryl groups, substituted or unsubstituted benzophenanthryl groups, substituted or unsubstituted phenalenyl groups, substituted or unsubstituted pyrenyl groups, substituted or unsubstituted crisenyl groups, substituted or unsubstituted benzocrisenyl groups, substituted or unsubstituted triphenylenyl groups, substituted or unsubstituted benzotriphenylenyl groups, substituted or unsubstituted tetracenyl groups, substituted or unsubstituted pentacenyl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted 9,9'-spirobifluorenyl groups, and substituted or unsubstituted benzofluor Preferably, the group is an orenyl group, a substituted or unsubstituted dibenzofluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted benzofluoranthenyl group, a substituted or unsubstituted perilenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted dinaphthofuranyl group, a substituted or unsubstituted benzoxanthenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted naphthobenzothiophenyl group, a substituted or unsubstituted dinaphthothiophenyl group, or a substituted or unsubstituted benzothioxanthenyl group.
[0361] In the above formulas (H131), (H132), and (H133), Ar 13It is more preferable that the group is a substituted or unsubstituted benzoanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted benzoxanthenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted naphthobenzothiophenyl group, or a substituted or unsubstituted benzothioxanthenyl group.
[0362] Ar in the above formula (H150) 151 It is preferable that the group is represented by one of the following formulas selected from the group consisting of formulas (H141) to (H149). The Ar in formulas (H131), (H132) and (H133) 13 Preferably, the group is represented by one of the formulas selected from the group consisting of the following formulas (H141) to (H149).
[0363]
[0364]
[0365]
[0366]
[0367] (In the above formulas (H141) to (H149), X 4 is an oxygen atom or a sulfur atom, Rp 1 ~Rp 11 One or more pairs of adjacent elements from among them either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine with each other, Rq 1 ~Rq 11 One or more pairs of adjacent elements from among them either bond to each other to form a substituted or unsubstituted monoring, or bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other, Rr 1 ~Rr 9One or more pairs of adjacent elements from among them either bond to each other to form a substituted or unsubstituted monoring, or bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other, Rs 1 ~Rs 9 One or more pairs of adjacent elements from among them either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine with each other, Rt 1 ~RT 8 One or more pairs of adjacent elements from among them either bond to each other to form a substituted or unsubstituted monoring, or bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other. Ru 1 ~Ru 10 One or more pairs of adjacent elements from among them either bond to each other to form a substituted or unsubstituted monoring, or bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other, Rv 1 ~Rv 10 One or more pairs of adjacent elements from among them either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine with each other, Rw 1 ~Rw 10 One or more pairs of adjacent elements from among them either bond to each other to form a substituted or unsubstituted monoring, or bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other, Rx 1 ~Rx 10 One or more pairs of adjacent Rp elements either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine to form the substituted or unsubstituted monoring and do not form the substituted or unsubstituted fused ring. 1 ~Rp 11 , Rq 1 ~Rq 11 , Rr 1 ~Rr 9, Rs 1 to Rs 9 , Rt 1 to Rt 8 , Ru 1 to Ru 10 , Rv 1 to Rv 10 , Rw 1 to Rw 10 , and Rx 1 to Rx 10 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, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms; * represents a bonding position to L in formula (H150) or a bonding position to L in formula (H131); one selected from the group consisting of Rt 151 to L in the above formula (H150) or to L in the above formula (H131), and one selected from the group consisting of Rt 13 represents a single bond bonded to L in the above formula (H150) or a single bond bonded to L in the above formula (H131), one selected from the group consisting of Ru 1 to Ru 8 represents a single bond bonded to L in the above formula (H150) or a single bond bonded to L in the above formula (H131), one selected from the group consisting of Ru 151 to Rv 13 represents a single bond bonded to L in the above formula (H150) or a single bond bonded to L in the above formula (H131), and Rv 1 to Rv 10 represents a single bond bonded to L in the above formula (H150) or a single bond bonded to L in the above formula (H131), and Rv 151 to Rv 13 represents a single bond bonded to L in the above formula (H150) or a single bond bonded to L in the above formula (H131), and Rv 1 to Rv10 One selected from the group consisting of is L in formula (H150). 151 A single bond that combines with or L in formula (H131) 13 Rw represents a single bond that connects to it. 1 ~Rw 10 One selected from the group consisting of is L in formula (H150). 151 A single bond that combines with or L in formula (H131) 13 This represents a single bond that connects with Rx 1 ~Rx 10 One selected from the group consisting of is L in formula (H150). 151 A single bond that combines with or L in formula (H131) 13 This represents a single bond that connects with (H141) to (H149) above. 901 ~R 905 , R 801 and R 802 These are, respectively, R in the above formula (H1-1). 901 ~R 905 , R 801 and R 802 (This is synonymous with...)
[0368] In the organic EL element according to this embodiment, Ar in formula (H150) 151 , and Ar in formulas (H131), (H132) and (H133) 13This includes a substituted or unsubstituted pyrene skeleton, a substituted or unsubstituted benzanthracene skeleton, a substituted or unsubstituted xanthene skeleton, a substituted or unsubstituted benzoxanthene skeleton, a substituted or unsubstituted chrysene skeleton, a substituted or unsubstituted benzochrysene skeleton, a substituted or unsubstituted fluorantene skeleton, a substituted or unsubstituted benzofluorantene skeleton, a substituted or unsubstituted triphenylene skeleton, a substituted or unsubstituted benzotriphenylene skeleton, a substituted or unsubstituted phenanthrene skeleton, a substituted or unsubstituted benzophenanthrene skeleton, a substituted or unsubstituted phenanthrofuran skeleton, a substituted or unsubstituted fluorene skeleton, a substituted or unsubstituted benzofluorene skeleton, a substituted or unsubstituted dibenzofuran skeleton, a substituted or unsubstituted naphthobenzofuran skeleton, a substituted or unsubstituted dinaphthofuran skeleton, a substituted or unsubstituted dibenzothiophene skeleton, and a substituted or unsubstituted naphthobenzothiophene skeleton. It is also preferable that the group be derived from a skeleton selected from the group consisting of substituted or unsubstituted dinaphthothiophene skeletons and substituted or unsubstituted indolocarbazole skeletons.
[0369] In the organic EL element according to this embodiment, Ar in formula (H150) 151 , and Ar in formulas (H131), (H132) and (H133) 13 It is also preferable that the group is derived from a skeleton selected from the group consisting of a substituted or unsubstituted pyrene skeleton, a substituted or unsubstituted benzanthracene skeleton, a substituted or unsubstituted benzoxanthene skeleton, a substituted or unsubstituted chrysene skeleton, a substituted or unsubstituted triphenylene skeleton, a substituted or unsubstituted benzotriphenylene skeleton, a substituted or unsubstituted phenanthrene skeleton, a substituted or unsubstituted phenanthrofuran skeleton, a substituted or unsubstituted fluorene skeleton, a substituted or unsubstituted benzofluorene skeleton, a substituted or unsubstituted dibenzofuran skeleton, a substituted or unsubstituted naphthobenzofuran skeleton, a substituted or unsubstituted dinaphthofuran skeleton, a substituted or unsubstituted dibenzothiophene skeleton, and a substituted or unsubstituted indolocarbazole skeleton.
[0370] In the organic EL element according to this embodiment, the first host material is preferably a compound having one or more deuterium atoms.
[0371] In the organic EL element according to this embodiment, the first host material is preferably a compound having a deuterated content of 50% or more, 60% or more, 70% or more, 80% or more, 90% or more, or 95% or more. The deuterated content of the compound is the number of deuterium atoms in the molecule of the compound N D And the number of light hydrogen atoms in the molecule of the compound, N H And the total number of hydrogen atoms in the molecule of the compound, N. A (=N D +N H Based on ) and , it can be calculated using the following formula (formula W1). In formula (formula W1), R D This represents the deuteration rate of the compound. D = (N D / N A ) × 100 … (Number W1)
[0372] In the organic EL element according to this embodiment, it is also preferable that the substituent in the first host material, when referred to as "substituted or unsubstituted," is an unsubstituted C1-C18 alkyl group, an unsubstituted ring-forming C3-C18 cycloalkyl group, an unsubstituted ring-forming C6-C18 aryl group, or an unsubstituted ring-forming C5-C18 heterocyclic group.
[0373] In the organic EL element according to this embodiment, it is also preferable that the substituent in the first host material, when referred to as "substituted or unsubstituted," is an unsubstituted C1-C6 alkyl group, an unsubstituted ring-forming C3-C10 cycloalkyl group, an unsubstituted ring-forming C6-C12 aryl group, or an unsubstituted ring-forming C5-C13 heterocyclic group.
[0374] In the organic EL element according to this embodiment, it is also preferable that all groups described as "substituted or unsubstituted" in the first host material are "unsubstituted" groups.
[0375] (Method for producing the first host material) The first host material can be produced by known methods. Alternatively, the first host material can also be produced by following known methods and using known alternative reactions and raw materials suited to the target product.
[0376] (Specific examples of the first host material) Examples of the first host material include the following compounds. However, the present invention is not limited to these specific examples of the first host material.
[0377]
[0378]
[0379]
[0380]
[0381]
[0382]
[0383]
[0384]
[0385]
[0386]
[0387]
[0388]
[0389]
[0390]
[0391]
[0392]
[0393]
[0394]
[0395]
[0396]
[0397]
[0398]
[0399]
[0400]
[0401]
[0402]
[0403]
[0404]
[0405]
[0406] (Second host material) In the organic EL element according to this embodiment, the second host material is preferably a compound represented by the following formula (H2).
[0407]
[0408] (In the above formula (H2), R 201 ~R 208 Each of these independently consists of a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C1-C50 haloalkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -Si(R 901 ) (Caution 902 ) (Caution 903 A group represented by ) -O-(R 904 A group represented by ) -S-(R 905 A group represented by ) -N(R 906 ) (Caution 907 A group represented by ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 The base represented by -COOR 802The group represented by R is 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. 201 ~R 208 Any set of two or more adjacent elements among them does not combine with each other, L 201 and L 202 Each is independently an arylene group with 6 to 50 ring-forming carbon atoms, either single-bonded, substituted, or unsubstituted, or a divalent heterocyclic group with 5 to 50 ring-forming atoms, and Ar 201 and Ar 202 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.) (In the second host material, R 901 ~R 907 , R 801 and R 802 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group, and R 901 If multiple R 901 They are either identical or different from each other, R 902 If multiple R 902 They are either identical or different from each other, R 903 If multiple R 903 They are either identical or different from each other, R 904 If multiple R 904 They are either identical or different from each other, R 905 If multiple R 905 They are either identical or different from each other, R 906 If multiple R 906 They are either identical or different from each other, R 907 If multiple R 907They are either identical or different from each other, R 801 If multiple R 801 They are either identical or different from each other, R 802 If multiple R 802 (They are either identical or different to each other.)
[0409] In the organic EL element according to this embodiment, R in the second host material 201 ~R 208 Each of these independently comprises a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C1-C50 haloalkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -Si(R 901 ) (Caution 902 ) (Caution 903 A group represented by ) -O-(R 904 A group represented by -S-(R 905 A group represented by ), -N(R 906 ) (Caution 907 A group represented by ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 The base represented by -COOR 802 The group represented by L is a halogen atom, a cyano group, or a nitro group. 201 and L 202 Each is independently an arylene group with 6 to 50 ring-forming carbon atoms, either single-bonded, substituted, or unsubstituted, or a divalent heterocyclic group with 5 to 50 ring-forming atoms, Ar 201 and Ar 202 Preferably, each of these is independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
[0410] In the organic EL element according to this embodiment, L in the second host material 201 and L 202 Each is independently a single bond, or a substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, Ar 201 and Ar202 These are also preferably independently substituted or unsubstituted aryl groups having 6 to 50 carbon atoms in a ring.
[0411] In the organic EL element according to this embodiment, Ar in the second host material 201 and Ar 202 It is also preferable that each of these groups independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted benzodiphenylfluorenyl group, a substituted or unsubstituted benzodimethylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted naphthobenzothienyl group.
[0412] In the organic EL element according to this embodiment, the second host material is also preferably a compound represented by the following formulas (H201), (H202), (H203), (H204), (H205), (H206), (H207), (H208), or (H209).
[0413]
[0414]
[0415]
[0416]
[0417]
[0418] (In the above formulas (H201) to (H209), L 201 and Ar 201 These are, respectively, L in the above formula (H2). 201 and Ar 201 It is synonymous with R 201 ~R 208Each of these corresponds to R in the above formula (H2). 201 ~R 208 (This is synonymous with...)
[0419] In the organic EL element according to this embodiment, R in the second host material 201 ~R 208 Each of these independently comprises a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, or -Si(R 901 ) (Caution 902 ) (Caution 903 It is preferable that the group is represented by ).
[0420] In the organic EL element according to this embodiment, L in the second host material 201 Ar is a single bond, or a substituted or unsubstituted ring-forming arylene group with 6 to 22 carbon atoms, 201 It is also preferable that the ring-forming aryl group has 6 to 22 carbon atoms and is either substituted or unsubstituted.
[0421] In the organic EL element according to this embodiment, L in the second host material 201 Ar is a single bond, or a substituted or unsubstituted ring-forming arylene group with 6 to 14 carbon atoms, 201 It is also preferable that the ring-forming aryl group has 6 to 14 carbon atoms and is substituted or unsubstituted.
[0422] In the organic EL element according to this embodiment, L in the second host material 201 Ar is a single bond, or a substituted or unsubstituted ring-forming arylene group with 6 to 12 carbon atoms, 201 It is also preferable that the ring-forming aryl group has 6 to 12 carbon atoms and is substituted or unsubstituted.
[0423] In the organic EL element according to this embodiment, L in the second host material 201 is a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group, Ar 201 It is also preferable that this be a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.
[0424] In the organic EL element according to this embodiment, Ar in the second host material 201 and Ar 202 Preferably, at least one of the following is represented by the formula (H2a), Ar 201 However, it is more preferable that it be represented by the following formula (H2a).
[0425]
[0426] (In the above formula (H2a), X 20 is an oxygen atom or a sulfur atom, R 11 and R 12 Group R 12 and R 13 The group, and R 13 and R 14 One set selected from the group consisting of sets of either combines with each other to form a ring represented by formula (H2aa), or does not combine with each other, where * in formula (H2aa) indicates the position of combination with formula (H2a), and R in formula (H2a) 11 ~R 18 , and R in the above formula (H2aa) 21 ~R 24 One of the groups consisting of is L 201 R represents a single bond that connects to another element, and R represents a bond that is not a single bond. 11 ~R 18 and R 21 ~R 24 Each of these independently consists of a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C1-C50 haloalkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -Si(R 901 ) (Caution 902 ) (Caution 903 A group represented by ) -O-(R 904 A group represented by ) -S-(R 905 A group represented by ) -N(R 906 ) (Caution 907A group represented by ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 The base represented by -COOR 802 The group represented by is 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.) (In the above formulas (H2a) and (H2aa), R 901 ~R 907 , R 801 and R 802 These are, respectively, R in the above formula (H2). 901 ~R 907 , R 801 and R 802 (This is synonymous with...)
[0427] Ar 202 However, when it is represented by the above formula (H2a), R in the above formula (H2a) 11 ~R 18 , and R in the above formula (H2aa) 21 ~R 24 One of the groups consisting of is L 202 This represents a single bond that connects to [another element].
[0428] In the organic EL element according to this embodiment, the second host material is also preferably a compound represented by the following formula (H21).
[0429]
[0430] (In the above formula (H21), R 201 ~R 208 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 11 ~R 13 and R 15 ~R 18Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 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, L 202 This is an arylene group with 6 to 50 ring-forming carbon atoms, either single-bonded, substituted, or unsubstituted, or a divalent heterocyclic group with 5 to 50 ring-forming atoms, and Ar 202 (This refers to a substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 ring-forming atoms.)
[0431] In the organic EL element according to this embodiment, Ar in the second host material 201 and Ar 202 Preferably, at least one of them is represented by the following formula (H2b), Ar 201 However, it is preferable that it be represented by the following formula (H2b).
[0432]
[0433] (In the above formula (H2b), X 21 is an oxygen atom or a sulfur atom, R 31 ~R 38 Each of these independently consists of a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C1-C50 haloalkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -Si(R 901 ) (Caution 902 ) (Caution 903 A group represented by ) -O-(R 904 A group represented by ) -S-(R 905 A group represented by ) -N(R 906 ) (Caution 907 A group represented by ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 The base represented by -COOR 802The group represented by R is 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. 31 ~R 38 One of them is L 201 This represents a single bond that connects with (H2b). ) (In the above formula (H2b), R 901 ~R 907 , R 801 and R 802 These are, respectively, R in the above formula (H2). 901 ~R 907 , R 801 and R 802 (This is synonymous with...)
[0434] Ar 202 However, when expressed by the above formula (H2b), R 31 ~R 38 One of them is L 202 This represents a single bond that connects to [another element].
[0435] In the organic EL element according to this embodiment, the second host material is preferably a compound having one or more deuterium atoms.
[0436] In the organic EL element according to this embodiment, it is preferable that the first host material is a compound having one or more deuterium atoms, and the second host material is a compound having one or more deuterium atoms.
[0437] In the organic EL element according to this embodiment, the second host material is preferably a compound having a deuteration rate of 50% or more, 60% or more, 70% or more, 80% or more, 90% or more, or 95% or more.
[0438] In the organic EL element according to this embodiment, it is preferable that the first host material is a compound with a deuteration rate of 80% or more, and the second host material is a compound with a deuteration rate of 80% or more.
[0439] In the organic EL element according to this embodiment, R is a substituent of the anthracene skeleton in the second host material. 201 ~R 208It is preferable that the atom is a hydrogen atom in order to prevent the suppression of intermolecular interactions and to suppress the decrease in electron mobility, 201 ~R 208 This may be a substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 ring-forming atoms. 201 ~R 208 When the substituent is a bulky alkyl group or cycloalkyl group, intermolecular interactions are suppressed, reducing electron mobility to the first host material, and potentially failing to satisfy the relationship μe(H2) > μe(H1) described in the aforementioned formula (Equation 30). When the second host material is used as the second light-emitting layer, it is expected that the relationship μe(H2) > μe(H1) will be satisfied, thereby suppressing the decrease in the recombination ability of holes and electrons in the first light-emitting layer and the decrease in luminescence efficiency. The substituents include haloalkyl groups, alkenyl groups, alkynyl groups, and -Si(R 901 ) (Caution 902 ) (Caution 903 A group represented by ) -O-(R 904 A group represented by -S-(R 905 A group represented by ), -N(R 906 ) (Caution 907 A group represented by ), an aralkyl group, -C(=O)R 801 The base represented by -COOR 802 The group represented by, halogen atoms, cyano groups, and nitro groups may become bulky, and alkyl groups and cycloalkyl groups may become even bulkier. In the second host material, the substituent R of the anthracene skeleton 201 ~R 208 Preferably, the substituent is not bulky, and is not alkyl or cycloalkyl group, but alkyl, cycloalkyl, haloalkyl, alkenyl group, alkynyl group, -Si(R 901 ) (Caution 902 ) (Caution 903 A group represented by ) -O-(R 904 A group represented by -S-(R 905 A group represented by ), -N(R 906 ) (Caution 907 A group represented by ), an aralkyl group, -C(=O)R801 The base represented by -COOR 802 It is more preferable that the group is not a halogen atom, a cyano group, or a nitro group.
[0440] In the organic EL element according to this embodiment, in the second host material, R 201 ~R 208 Each of these independently comprises a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, or -Si(R 901 ) (Caution 902 ) (Caution 903 It is also preferable that the group be represented by ).
[0441] In the organic EL element according to this embodiment, in the second host material, R 201 ~R 208 It is preferable that it be a hydrogen atom.
[0442] In the second host material, R 201 ~R 208 In the case of "substituted or unsubstituted" in the above, it is preferable that the substituents do not include the substituents that may increase bulk as described above, particularly substituted or unsubstituted alkyl groups and substituted or unsubstituted cycloalkyl groups. 201 ~R 208 In the case of "substituted or unsubstituted" in this context, the substituents do not include substituted or unsubstituted alkyl groups and substituted or unsubstituted cycloalkyl groups. This prevents the suppression of intermolecular interactions caused by the presence of bulky substituents such as alkyl and cycloalkyl groups, thereby preventing a decrease in electron mobility. Furthermore, when such a second host material is used as the second light-emitting layer, it is possible to suppress a decrease in the recombination ability of holes and electrons in the first light-emitting layer, as well as a decrease in luminescence efficiency.
[0443] R is a substituent on the anthracene skeleton. 201 ~R 208 However, R is not a bulky substituent, but rather a substituent. 201 ~R 208 It is even more preferable that it is unsubstituted. Also, R, which is a substituent on the anthracene skeleton. 201 ~R208 When R is not a bulky substituent, 201 ~R 208 When a substituent is attached to it, it is preferable that the substituent is not bulky, and R as a substituent 201 ~R 208 The substituent bonded to is preferably not an alkyl group or a cycloalkyl group, but rather an alkyl group, a cycloalkyl group, a haloalkyl group, an alkenyl group, an alkynyl group, or -Si(R 901 ) (Caution 902 ) (Caution 903 A group represented by ) -O-(R 904 A group represented by -S-(R 905 A group represented by ), -N(R 906 ) (Caution 907 A group represented by ), an aralkyl group, -C(=O)R 801 The base represented by -COOR 802 It is more preferable that the group is not a halogen atom, a cyano group, or a nitro group.
[0444] In the organic EL element according to this embodiment, it is also preferable that the substituent in the second host material, when referred to as "substituted or unsubstituted," is an unsubstituted C1-C18 alkyl group, an unsubstituted ring-forming C3-C18 cycloalkyl group, an unsubstituted ring-forming C6-C18 aryl group, or an unsubstituted ring-forming C5-C18 heterocyclic group.
[0445] In the organic EL element according to this embodiment, it is also preferable that the substituent in the second host material, when referred to as "substituted or unsubstituted," is an unsubstituted C1-C6 alkyl group, an unsubstituted ring-forming C3-C10 cycloalkyl group, an unsubstituted ring-forming C6-C12 aryl group, or an unsubstituted ring-forming C5-C13 heterocyclic group.
[0446] In the organic EL element according to this embodiment, it is also preferable that all groups described as "substituted or unsubstituted" in the second host material are "unsubstituted" groups.
[0447] (Method for manufacturing the second host material) The second host material can be manufactured by known methods. Alternatively, the second host material can also be manufactured by following known methods and using known alternative reactions and raw materials suited to the target substance.
[0448] (Specific examples of the second host material) Examples of the second host material include the following compounds. However, the present invention is not limited to these specific examples of the second host material.
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[0450]
[0451]
[0452]
[0453]
[0454]
[0455]
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[0457]
[0458]
[0459]
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[0461]
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[0475]
[0476] Let's further explain the configuration of the organic EL element.
[0477] (Substrate) The substrate is used as a support for the organic EL element. Examples of substrates include glass, quartz, and plastic. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples include plastic substrates. Examples of materials for forming a plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. An inorganic vapor-deposited film may also be used.
[0478] (Anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof with a large work function (specifically, 4.0 eV or more). Specifically, examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, etc. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metallic materials (e.g., titanium nitride).
[0479] These materials are typically deposited by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1% to 10% by mass of zinc oxide relative to indium oxide. Similarly, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5% to 5% by mass of tungsten oxide and 0.1% to 1% by mass of zinc oxide relative to indium oxide. Other methods such as vacuum deposition, coating, inkjet, and spin coating may also be used.
[0480] 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 anode's work function. Therefore, any material suitable for electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.
[0481] Materials with low work functions, such as elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these, can also be used. When forming an anode using alkali metals, alkaline earth metals, or alloys containing these, vacuum deposition or sputtering methods can be used. Furthermore, when using silver paste or similar materials, coating methods or inkjet methods can be employed.
[0482] When the organic EL element is of the bottom emission type, the anode is preferably formed of a metallic material that is light-transmitting or semi-transparent, allowing light from the light-emitting layer to pass through. In this specification, light-transmitting or semi-transparent means the property of transmitting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The metallic material having light transmission or semi-transparency can be appropriately selected from the materials listed in the anode section.
[0483] When the organic EL element is of the top-emission type, the anode is a reflective electrode having a reflective layer. The reflective layer is preferably formed of a metallic material having light reflectivity. In this specification, light reflectivity means the property of reflecting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The metallic material having light reflectivity can be appropriately selected from the materials listed in the anode section. The anode may consist only of a reflective layer, or it may be a multilayer structure having a reflective layer and a conductive layer (preferably a transparent conductive layer). When the anode has a reflective layer and a conductive layer, it is preferable that the conductive layer is placed between the reflective layer and the hole transport band. The conductive layer can be appropriately selected from the materials listed in the anode section.
[0484] (Cathode) For the cathode, it is preferable to use metals, alloys, electrically conductive compounds, and mixtures thereof that have a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.
[0485] Furthermore, when forming a cathode using alkali metals, alkaline earth metals, or alloys containing these, vacuum deposition or sputtering methods can be used. Additionally, when using silver paste or similar materials, coating or inkjet methods can be employed.
[0486] Furthermore, by providing an electron injection layer, cathodes can be formed using various conductive materials such as Al, Ag, ITO, graphene, silicon, or indium oxide-tin oxide containing silicon oxide, regardless of the magnitude of the work function. These conductive materials can be deposited using methods such as sputtering, inkjet printing, or spin coating.
[0487] When the organic EL element is of the bottom emission type, the cathode is a reflective electrode. The reflective electrode is preferably formed from a light-reflecting metallic material. The light-reflecting metallic material can be appropriately selected from the materials listed in the cathode section.
[0488] When the organic EL element is of the top-emission type, the cathode is preferably formed of a metallic material that is light-transmitting or semi-transparent, allowing light from the light-emitting layer to pass through. The light-transmitting or semi-transparent metallic material can be appropriately selected from the materials listed in the cathode section.
[0489] The organic EL element according to the first embodiment may be a bottom-emission type organic EL element. Alternatively, the organic EL element according to this embodiment may be a top-emission type organic EL element. When the organic EL element is a bottom-emission type, it is preferable that the anode is a light-transmitting electrode and the cathode is a light-reflecting electrode. When the organic EL element is a top-emission type, it is preferable that the anode is a light-reflecting electrode and the cathode is a light-transmitting electrode.
[0490] (Capping Layer) When an organic EL element is of the top-emission type, the organic EL element usually has a capping layer above 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 in which layers containing these materials are stacked can also be used as a capping layer.
[0491] (Hole Injection Layer) The hole injection layer is a layer containing a material with high hole injection properties. Examples of materials 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, substances with high hole injection potential include low-molecular-weight organic compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviated as TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviated as DNTPD), 1, Aromatic amine compounds such as 3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviated as DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviated as PCzPCN1) can also be used. Furthermore, high molecular weight compounds (oligomers, dendrimers, polymers, etc.) can be used as substances with high hole injection capabilities. Examples of high molecular weight compounds include poly(N-vinylcarbazole) (abbreviated as PVK), poly(4-vinyltriphenylamine) (abbreviated as PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD).Furthermore, polymer compounds to which acids such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS) have been added can also be used.
[0492] (Hole Transport Layer) The hole transport layer is a layer containing a substance with high hole transport properties. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used in the hole transport layer. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl Aromatic amine compounds such as phenyl (abbreviated as DFLDPBi), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviated as TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB) can be used. The substances described here are mainly 10 -6 cm 2 The material has a hole mobility of 1 / Vs or higher. Carbazole derivatives such as CBP, CzPA, and PCzPA, or anthracene derivatives such as t-BuDNA, DNA, and DPANth may be used for the hole transport layer. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) may also be used. However, other materials may be used as long as they have higher hole transport capabilities than electron transport capabilities. The layer containing the material with high hole transport capabilities may be a single layer or a layer consisting of two or more layers of the above materials stacked together.
[0493] (Electron Barrier Layer) The electron barrier layer is preferably a layer that transports holes and prevents electrons from reaching the anode-side layer (e.g., the hole transport layer). In the organic EL device of this embodiment, the compound contained in the electron barrier layer is, for example, a compound used in known electron barrier layers, and includes at least one compound selected from the group consisting of aromatic amine compounds and carbazole derivatives. The compound contained in the electron barrier layer may also be a monoamine compound having only one substituted or unsubstituted amino group in the molecule. The compound contained in the electron barrier layer may also have a substituted or unsubstituted carbazolyl group and one substituted or unsubstituted amino group in the molecule. The electron barrier layer may also be a layer that prevents excitons generated in the light-emitting layer from moving to the anode-side layer (e.g., the hole transport layer and the hole injection layer) so that excitation energy does not leak from the light-emitting layer to the surrounding layers.
[0494] (Hole Barrier Layer) The hole barrier layer is preferably a layer that transports electrons and prevents holes from reaching the cathode-side layer (e.g., the electron transport layer). The compound contained in the hole barrier layer is, for example, a compound used in known hole barrier layers. The compound contained in the hole barrier layer is preferably at least one compound selected from the group consisting of metal complexes, heteroaromatic compounds, and polymer compounds, similar to the compounds that can be used in the electron transport layer described later. Alternatively, the compound contained in the hole barrier layer may be at least one compound selected from the group consisting of imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives. In the organic EL element according to this embodiment, the electron transport band material contained in the hole barrier layer is preferably a diazine derivative or a triazine derivative, and more preferably a pyrimidine derivative or a 1,3,5-triazine derivative. The hole barrier layer is also preferably a layer that prevents excitons generated in the light-emitting layer from moving to layers on the cathode side of the hole barrier layer (for example, electron transport layers and electron injection layers) so that excitation energy does not leak from the light-emitting layer to the surrounding layers.
[0495] (Electron Transport Layer) The electron transport layer is a layer containing a material with high electron transport properties. The electron transport layer can contain: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) polymer compounds. Specifically, low-molecular-weight organic compounds such as Alq and tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq) can be used. 3 ), bis(10-hydroxybenzo[h]quinolinate)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-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: Heteroaromatic compounds such as (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), vasophenanthroline (abbreviated as BPhen), vasocuproin (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviated as BzOs) can also be used. The substances described here are mainly 10 -6 cm 2The material has an electron mobility of 1 / Vs or higher. However, any material with higher electron transport properties than hole transport properties may be used as the electron transport layer. Furthermore, the electron transport layer may be a single layer or a layer consisting of two or more layers of the above material. Polymer compounds can also be used for the electron transport layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy), etc., can be used.
[0496] (Electron injection layer) The electron injection layer is a layer containing a material with high electron injection potential. The electron injection layer contains lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF) 2Alkali metals such as lithium oxide (LiOx), alkaline earth metals, or compounds thereof can be used. In addition, materials containing alkali metals, alkaline earth metals, or compounds thereof in an electron-transporting substance, specifically those containing magnesium (Mg) in Alq, may be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, a composite material made by mixing an organic compound and an electron donor may be used in the electron injection layer. Such a composite material has 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 in transporting the generated electrons, and specifically, for example, the substances that constitute the electron transport layer described above (metal complexes, heteroaromatic compounds, etc.) can be used. As for the electron donor, any substance that exhibits electron-donating properties to the organic compound is acceptable. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples include lithium, cesium, magnesium, calcium, erbium, and ytterbium. Furthermore, alkali metal oxides and alkaline earth metal oxides are preferred, including 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.
[0497] (Layer Formation Method) The method for forming each layer of the organic EL element according to any of the embodiments described above is not limited to those specifically mentioned above, but known methods such as dry deposition methods such as vacuum deposition, sputtering, plasma deposition, and ion plating, and wet deposition methods such as spin coating, dipping, flow coating, and inkjet deposition can be employed.
[0498] (Film Thickness) The film thickness of each layer included in the light-emitting unit of the organic EL element according to the first embodiment is not limited unless otherwise 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 layer included in the light-emitting unit of the organic EL element is usually preferably in the range of a few nanometers to 1 μm.
[0499] <Schematic Configuration of Organic EL Element> Figure 1 shows a schematic configuration of a first example of an organic EL element according to this embodiment. The organic EL element 1 shown in Figure 1 includes a light-transmitting substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10 disposed between the anode 3 and the cathode 4. The light-emitting unit 10 includes, from the anode 3 side, a hole transport band 6, a light-emitting band 5, and an electron transport band 7 in that order. The hole transport band 6 includes, from the anode 3 side, a hole injection layer 61 and a hole transport layer 62 in that order. The light-emitting band 5 includes, from the anode 3 side, a first light-emitting layer 51 and a second light-emitting layer 52 in that order. The electron transport band 7 includes, from the anode 3 side, an electron transport layer 71 and an electron injection layer 72 in that order. The present invention is not limited to the configuration of the organic EL element shown in Figure 1. For example, in the organic EL element 1, a barrier layer may be included between the hole transport layer 62 and the first light-emitting layer 51, and it is preferable that the barrier layer is an electron barrier layer. Also, in the organic EL element 1, a barrier layer may be included between the second light-emitting layer 52 and the electron transport layer 71, and it is preferable that the barrier layer is a hole barrier layer.
[0500] Figure 2 shows a schematic configuration of a second example of an organic EL element according to this embodiment. The organic EL element 1A shown in Figure 2 includes a light-transmitting substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10A disposed between the anode 3 and the cathode 4. The light-emitting unit 10A includes, from the anode 3 side, a hole transport band 6, a light-emitting band 5A, and an electron transport band 7 in that order. The hole transport band 6 and electron transport band 7 in the organic EL element 1A are the same as those in the organic EL element 1. The light-emitting band 5A includes, from the anode 3 side, a second light-emitting layer 52 and a first light-emitting layer 51 in that order. The present invention is not limited to the configuration of the organic EL element shown in Figure 2. For example, in the organic EL element 1A, a barrier layer may be included between the hole transport layer 62 and the second light-emitting layer 52, and it is preferable that the barrier layer is an electron barrier layer. Furthermore, in the organic EL element 1A, a barrier layer may be included between the first light-emitting layer 51 and the electron transport layer 71, and it is preferable that the barrier layer is a hole barrier layer.
[0501] [Second Embodiment] (Electronic Device) The electronic device according to this embodiment is equipped with an organic electroluminescent element according to any of the embodiments described above. Examples of electronic devices include display devices and light-emitting devices. Examples of display devices include display components (e.g., organic EL panel modules), televisions, mobile phones, tablets, and personal computers. Examples of light-emitting devices include lighting and vehicle lights.
[0502] [Modifications of Embodiments] The present invention is not limited to the embodiments described above, and any modifications, improvements, etc., that can achieve the objectives of the present invention are included in the present invention.
[0503] For example, the light-emitting layer is not limited to two layers, but may consist of more than two light-emitting layers stacked together. When an organic EL element has more than two light-emitting layers, it is sufficient that at least two of the light-emitting layers satisfy the conditions described in the above embodiment. For example, the other light-emitting layers may be fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize light emission due to electron transitions from a triplet excited state to a direct ground state. Furthermore, when an organic EL element has multiple light-emitting layers, these light-emitting layers may be arranged adjacent to each other, or it may be a so-called tandem type organic EL element in which multiple light-emitting units are stacked with an intermediate layer in between.
[0504] Furthermore, for example, a barrier layer may be provided adjacent to at least one of the anode and cathode sides of the light-emitting layer. The barrier layer is preferably placed in contact with the light-emitting layer and blocks at least one of holes, electrons, and excitons. For example, if the barrier layer is placed in contact with the cathode side of the light-emitting layer, the barrier layer transports electrons and prevents holes from reaching the layer on the cathode side of the barrier layer (e.g., the electron transport layer). If the organic EL element includes an electron transport layer, it is preferable to include the barrier layer between the light-emitting layer and the electron transport layer. Also, if the barrier layer is placed in contact with the anode side of the light-emitting layer, the barrier layer transports holes and prevents electrons from reaching the layer on the anode side of the barrier layer (e.g., the hole transport layer). If the organic EL element includes a hole transport layer, it is preferable to include the barrier layer between the light-emitting layer and the hole transport layer. Furthermore, the barrier layer may be provided adjacent to the light-emitting layer to prevent excitation energy from leaking from the light-emitting layer to its surrounding layers. The barrier layer prevents excitons generated in the light-emitting layer from moving to the electrode-side layer (e.g., the electron transport layer and the hole transport layer). It is preferable that the light-emitting layer and the barrier layer are joined together.
[0505] Furthermore, the specific structure and shape in the implementation of the present invention may be other structures, etc., to the extent that the objectives of the present invention can be achieved.
[0506] The present invention will be described in more detail below with reference to examples. The present invention is not limited to these examples.
[0507] <Compounds> The structure of the first host material used in the manufacture of the organic EL elements in each example and comparative example is shown below.
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[0509]
[0510]
[0511]
[0512]
[0513]
[0514]
[0515]
[0516]
[0517]
[0518] The structures of the first or second dopant material used in the manufacture of the organic EL elements in each example and comparative example are shown below.
[0519]
[0520]
[0521] The structure of the second host material used in the manufacture of the organic EL elements in each example and comparative example is shown below.
[0522]
[0523]
[0524] The structures of other compounds used in the manufacture of the organic EL elements in each example and comparative example are shown below.
[0525]
[0526]
[0527] <Fabrication of Organic EL Devices 1> Organic EL devices were fabricated and evaluated as follows.
[0528] [Example 1] A glass substrate (manufactured by Geomatec Co., Ltd.) with a 25 mm x 75 mm x 1.1 mm thick ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes. The film thickness of the ITO transparent electrode was set to 135 nm. The glass substrate with the transparent electrode line after cleaning was mounted in the substrate holder of a vacuum deposition apparatus, and first, compound HT-1 and compound HA were co-deposited on the side where the transparent electrode line was formed, so as to cover the transparent electrode, forming a hole injection layer with a film thickness of 15 nm. The content of compound HT-1 in the hole injection layer was set to 90% by mass, and the content of compound HA was set to 10% by mass. Next, compound HT-1 and compound HT-2 were co-deposited on the hole injection layer to form a first hole transport layer with a film thickness of 70 nm. The first hole transport layer was configured with a content of 50% by mass of compound HT-1 and a content of 50% by mass of compound HT-2. Next, compound EBL was deposited on the first hole transport layer to form a second hole transport layer (also called an electron barrier layer) with a thickness of 15 nm. Compound BH1-1 (first host material) and compound BD-1 (first dopant material) were co-deposited on the second hole transport layer to form a first light-emitting layer with a thickness of 6 nm. The first light-emitting layer was configured with a content of 97% by mass of compound BH1-1 and a content of 3% by mass of compound BD-1. Compound BH2 (second host material) and compound BD-2 (second dopant material) were co-deposited on the first light-emitting layer to form a second light-emitting layer with a thickness of 24 nm. The second light-emitting layer was configured with a content of 97% by mass of compound BH2 and a content of 3% by mass of compound BD-2. Compounds ET-1 and ET-2 were co-deposited on the second light-emitting layer to form a first electron transport layer (also called a hole barrier layer) with a thickness of 20 nm. The content of compound ET-1 in the first electron transport layer was 50% by mass, and the content of compound ET-2 was 50% by mass. LiF was deposited on the first electron transport layer to form an electron injection layer with a thickness of 1 nm. Metallic Al was deposited on the electron injection layer to form a cathode with a thickness of 80 nm. The device configuration of Example 1 is schematically shown below.ITO(135) / HT-1:HA(15,90%:10%) / HT-1:HT-2(70,50%:50%) / EBL(15) / BH1-1:BD-1(6,97%:3%) / BH2:BD-2(24,97%:3%) / ET-1:ET-2(20,50%:50%) / LiF(1) / Al(80) The numbers in parentheses indicate the film thickness (unit: nm). Similarly, the percentage numbers in parentheses (90%:10%) indicate the mass %) content of compounds HT-1 and HA in the hole injection layer. The percentage numbers (50%:50%) indicate the mass %) content of compounds HT-1 and HT-2 in the first hole transport layer. The percentage figures (97%:3%) indicate the proportion (mass%) of the host material (compound BH1-1 or compound BH2) and dopant material (compound BD-1 or compound BD-2) in the first or second light-emitting layer. The percentage figures (50%:50%) indicate the content (mass%) of compound ET-1 and compound ET-2 in the first electron transport layer.
[0529] [Comparative Example 1-1] The organic EL element of Comparative Example 1-1 was manufactured in the same manner as in Example 1, except that, as shown in Table 1, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0530] [Comparative Example 1-2] The organic EL element of Comparative Example 1-2 was manufactured in the same manner as in Example 1, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 1.
[0531] [Comparative Examples 1-3, 1-4, and 1-5] The organic EL elements of Comparative Examples 1-3, 1-4, and 1-5 were manufactured in the same manner as in Example 1, except that the compounds used in the first and second light-emitting layers of Example 1 were replaced with the compounds listed in Table 1, and the first and second light-emitting layers were formed accordingly.
[0532] <Fabrication of Organic EL Devices 2> [Example 2] The organic EL device of Example 2 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 1 to form the first light-emitting layer.
[0533] [Comparative Example 2-1] The organic EL element of Comparative Example 2-1 was manufactured in the same manner as in Example 2, except that, as shown in Table 1, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0534] [Comparative Example 2-2] The organic EL element of Comparative Example 2-2 was manufactured in the same manner as in Example 2, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 1.
[0535] [Comparative Examples 2-3, 2-4, and 2-5] The organic EL elements of Comparative Examples 2-3, 2-4, and 2-5 were manufactured in the same manner as in Example 2, except that the compounds used in the first and second light-emitting layers of Example 2 were replaced with the compounds listed in Table 1, as shown in Table 1, to form the first and second light-emitting layers.
[0536] <Fabrication of Organic EL Devices 3> [Example 3] The organic EL device of Example 3 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 2, and the first light-emitting layer was formed using the same method as in Example 1.
[0537] [Comparative Example 3-1] The organic EL element of Comparative Example 3-1 was manufactured in the same manner as in Example 3, except that, as shown in Table 2, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0538] [Comparative Example 3-2] The organic EL element of Comparative Example 3-2 was manufactured in the same manner as in Example 3, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 2.
[0539] [Comparative Examples 3-3, 3-4, and 3-5] The organic EL elements of Comparative Examples 3-3, 3-4, and 3-5 were manufactured in the same manner as in Example 3, except that the compounds used in the first and second light-emitting layers of Example 3 were replaced with the compounds listed in Table 2, as shown in Table 2, to form the first and second light-emitting layers.
[0540] <Fabrication of Organic EL Devices 4> [Example 4] The organic EL device of Example 4 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 2, and the first light-emitting layer was formed using the same method as in Example 1.
[0541] [Comparative Example 4-1] The organic EL element of Comparative Example 4-1 was manufactured in the same manner as in Example 4, except that, as shown in Table 2, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0542] [Comparative Example 4-2] The organic EL element of Comparative Example 4-2 was manufactured in the same manner as in Example 4, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 2.
[0543] [Comparative Examples 4-3, 4-4, and 4-5] The organic EL elements of Comparative Examples 4-3, 4-4, and 4-5 were manufactured in the same manner as in Example 4, except that the compounds used in the first and second light-emitting layers of Example 4 were replaced with the compounds listed in Table 2, as shown in Table 2, to form the first and second light-emitting layers.
[0544] <Fabrication of Organic EL Devices 5> [Example 5] The organic EL device of Example 5 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 3, and the first light-emitting layer was formed in the same manner as in Example 1.
[0545] [Comparative Example 5-1] The organic EL element of Comparative Example 5-1 was manufactured in the same manner as in Example 5, except that, as shown in Table 3, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0546] [Comparative Example 5-2] The organic EL element of Comparative Example 5-2 was manufactured in the same manner as in Example 5, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 3.
[0547] [Comparative Examples 5-3, 5-4, and 5-5] The organic EL elements of Comparative Examples 5-3, 5-4, and 5-5 were manufactured in the same manner as in Example 5, except that the compounds used in the first and second light-emitting layers of Example 5 were replaced with the compounds listed in Table 3, as shown in Table 3, to form the first and second light-emitting layers.
[0548] <Fabrication of Organic EL Devices 6> [Example 6] The organic EL device of Example 6 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 3, and the first light-emitting layer was formed using the same method as in Example 1.
[0549] [Comparative Example 6-1] The organic EL element of Comparative Example 6-1 was manufactured in the same manner as in Example 6, except that, as shown in Table 3, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0550] [Comparative Example 6-2] The organic EL element of Comparative Example 6-2 was manufactured in the same manner as in Example 6, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 3.
[0551] [Comparative Examples 6-3, 6-4, and 6-5] The organic EL elements of Comparative Examples 6-3, 6-4, and 6-5 were manufactured in the same manner as in Example 6, except that the compounds used in the first and second light-emitting layers of Example 6 were replaced with the compounds listed in Table 3, as shown in Table 3, to form the first and second light-emitting layers.
[0552] <Fabrication of Organic EL Devices 7> [Example 7] The organic EL device of Example 7 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 4, and the first light-emitting layer was formed using the same method as in Example 1.
[0553] [Comparative Example 7-1] The organic EL element of Comparative Example 7-1 was manufactured in the same manner as in Example 7, except that, as shown in Table 4, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0554] [Comparative Example 7-2] The organic EL element of Comparative Example 7-2 was manufactured in the same manner as in Example 7, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 4.
[0555] [Comparative Examples 7-3, 7-4, and 7-5] The organic EL elements of Comparative Examples 7-3, 7-4, and 7-5 were manufactured in the same manner as in Example 7, except that the compounds used in the first and second light-emitting layers of Example 7 were replaced with the compounds listed in Table 4, as shown in Table 4, to form the first and second light-emitting layers.
[0556] <Fabrication of Organic EL Devices 8> [Example 8] The organic EL device of Example 8 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 4, and the first light-emitting layer was formed using the same method as in Example 1.
[0557] [Comparative Example 8-1] The organic EL element of Comparative Example 8-1 was manufactured in the same manner as in Example 8, except that, as shown in Table 4, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0558] [Comparative Example 8-2] The organic EL element of Comparative Example 8-2 was manufactured in the same manner as in Example 8, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 4.
[0559] [Comparative Examples 8-3, 8-4, and 8-5] The organic EL elements of Comparative Examples 8-3, 8-4, and 8-5 were manufactured in the same manner as in Example 8, except that the compounds used in the first and second light-emitting layers of Example 8 were replaced with the compounds listed in Table 4, as shown in Table 4, to form the first and second light-emitting layers.
[0560] <Fabrication of Organic EL Devices 9> [Example 9] The organic EL device of Example 9 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 5, and the first light-emitting layer was formed using the same method as in Example 1.
[0561] [Comparative Example 9-1] The organic EL element of Comparative Example 9-1 was manufactured in the same manner as in Example 9, except that, as shown in Table 5, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0562] [Comparative Example 9-2] The organic EL element of Comparative Example 9-2 was manufactured in the same manner as in Example 9, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 5.
[0563] [Comparative Examples 9-3, 9-4, and 9-5] The organic EL elements of Comparative Examples 9-3, 9-4, and 9-5 were manufactured in the same manner as in Example 9, except that the compounds used in the first and second light-emitting layers of Example 9 were replaced with the compounds listed in Table 5, as shown in Table 5, to form the first and second light-emitting layers.
[0564] <Fabrication of Organic EL Device 10> [Example 10] The organic EL device of Example 10 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 5, and the first light-emitting layer was formed using the compound listed in Table 5.
[0565] [Comparative Example 10-1] The organic EL element of Comparative Example 10-1 was manufactured in the same manner as in Example 10, except that, as shown in Table 5, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0566] [Comparative Example 10-2] The organic EL element of Comparative Example 10-2 was manufactured in the same manner as in Example 10, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 5.
[0567] [Comparative Examples 10-3, 10-4, and 10-5] The organic EL elements of Comparative Examples 10-3, 10-4, and 10-5 were manufactured in the same manner as in Example 10, except that the compounds used in the first and second light-emitting layers of Example 10 were replaced with the compounds listed in Table 5, as shown in Table 5, to form the first and second light-emitting layers.
[0568] <Fabrication of Organic EL Device 11> [Example 11] The organic EL device of Example 11 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 6 to form the first light-emitting layer.
[0569] [Comparative Example 11-1] The organic EL element of Comparative Example 11-1 was manufactured in the same manner as in Example 11, except that, as shown in Table 6, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0570] [Comparative Example 11-2] The organic EL element of Comparative Example 11-2 was manufactured in the same manner as in Example 11, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 6.
[0571] [Comparative Examples 11-3, 11-4, and 11-5] The organic EL elements of Comparative Examples 11-3, 11-4, and 11-5 were manufactured in the same manner as in Example 11, except that the compounds used for the first and second light-emitting layers in Example 11 were replaced with the compounds listed in Table 6, as shown in Table 6, to form the first and second light-emitting layers.
[0572] <Fabrication of Organic EL Device 12> [Example 12] The organic EL device of Example 12 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 6 to form the first light-emitting layer.
[0573] [Comparative Example 12-1] The organic EL element of Comparative Example 12-1 was manufactured in the same manner as in Example 12, except that, as shown in Table 6, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0574] [Comparative Example 12-2] The organic EL element of Comparative Example 12-2 was manufactured in the same manner as in Example 12, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 6.
[0575] [Comparative Examples 12-3, 12-4, and 12-5] The organic EL elements of Comparative Examples 12-3, 12-4, and 12-5 were manufactured in the same manner as in Example 12, except that the compounds used for the first and second light-emitting layers in Example 12 were replaced with the compounds listed in Table 6, and the first and second light-emitting layers were formed accordingly.
[0576] <Fabrication of Organic EL Device 13> [Example 13] The organic EL device of Example 13 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 7 to form the first light-emitting layer.
[0577] [Comparative Example 13-1] The organic EL element of Comparative Example 13-1 was manufactured in the same manner as in Example 13, except that, as shown in Table 7, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0578] [Comparative Example 13-2] The organic EL element of Comparative Example 13-2 was manufactured in the same manner as in Example 13, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 7.
[0579] [Comparative Examples 13-3, 13-4, and 13-5] The organic EL elements of Comparative Examples 13-3, 13-4, and 13-5 were manufactured in the same manner as in Example 13, except that the compounds used for the first and second light-emitting layers in Example 13 were replaced with the compounds listed in Table 7, as shown in Table 7, to form the first and second light-emitting layers.
[0580] <Fabrication of Organic EL Device 14> [Example 14] The organic EL device of Example 14 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 7, and the first light-emitting layer was formed using the same method as in Example 1.
[0581] [Comparative Example 14-1] The organic EL element of Comparative Example 14-1 was manufactured in the same manner as in Example 14, except that, as shown in Table 7, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0582] [Comparative Example 14-2] The organic EL element of Comparative Example 14-2 was manufactured in the same manner as in Example 14, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 7.
[0583] [Comparative Examples 14-3, 14-4, and 14-5] The organic EL elements of Comparative Examples 14-3, 14-4, and 14-5 were manufactured in the same manner as in Example 14, except that the compounds used in the first and second light-emitting layers of Example 14 were replaced with the compounds listed in Table 7, as shown in Table 7, to form the first and second light-emitting layers.
[0584] <Fabrication of Organic EL Device 15> [Example 15] The organic EL device of Example 15 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 8 to form the first light-emitting layer.
[0585] [Comparative Example 15-1] The organic EL element of Comparative Example 15-1 was manufactured in the same manner as in Example 15, except that, as shown in Table 8, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0586] [Comparative Example 15-2] The organic EL element of Comparative Example 15-2 was manufactured in the same manner as in Example 15, except that, as shown in Table 8, a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer.
[0587] [Comparative Examples 15-3, 15-4, and 15-5] The organic EL elements of Comparative Examples 15-3, 15-4, and 15-5 were manufactured in the same manner as in Example 15, except that the compounds used in the first and second light-emitting layers of Example 15 were replaced with the compounds listed in Table 8, as shown in Table 8, to form the first and second light-emitting layers.
[0588] <Fabrication of Organic EL Device 16> [Example 16] The organic EL device of Example 16 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 8 to form the first light-emitting layer.
[0589] [Comparative Example 16-1] The organic EL element of Comparative Example 16-1 was manufactured in the same manner as in Example 16, except that, as shown in Table 8, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0590] [Comparative Example 16-2] The organic EL element of Comparative Example 16-2 was manufactured in the same manner as in Example 16, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 8.
[0591] [Comparative Examples 16-3, 16-4, and 16-5] The organic EL elements of Comparative Examples 16-3, 16-4, and 16-5 were manufactured in the same manner as in Example 16, except that the compounds used for the first and second light-emitting layers in Example 16 were replaced with the compounds listed in Table 8, as shown in Table 8, to form the first and second light-emitting layers.
[0592] <Fabrication of Organic EL Device 17> [Example 17] The organic EL device of Example 17 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 9 to form the first light-emitting layer.
[0593] [Comparative Example 17-1] The organic EL element of Comparative Example 17-1 was manufactured in the same manner as in Example 17, except that, as shown in Table 9, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0594] [Comparative Example 17-2] The organic EL element of Comparative Example 17-2 was manufactured in the same manner as in Example 17, except that, as shown in Table 9, a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer.
[0595] [Comparative Examples 17-3, 17-4, and 17-5] The organic EL elements of Comparative Examples 17-3, 17-4, and 17-5 were manufactured in the same manner as in Example 17, except that the compounds used in the first and second light-emitting layers of Example 17 were replaced with the compounds listed in Table 9 to form the first and second light-emitting layers, as shown in Table 9.
[0596] <Fabrication of Organic EL Device 18> [Example 18] The organic EL device of Example 18 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 9 to form the first light-emitting layer.
[0597] [Comparative Example 18-1] The organic EL element of Comparative Example 18-1 was manufactured in the same manner as in Example 18, except that, as shown in Table 9, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0598] [Comparative Example 18-2] The organic EL element of Comparative Example 18-2 was manufactured in the same manner as in Example 18, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 9.
[0599] [Comparative Examples 18-3, 18-4, and 18-5] The organic EL elements of Comparative Examples 18-3, 18-4, and 18-5 were manufactured in the same manner as in Example 18, except that the compounds used in the first and second light-emitting layers of Example 18 were replaced with the compounds listed in Table 9 to form the first and second light-emitting layers, as shown in Table 9.
[0600] <Fabrication of Organic EL Device 19> [Example 19] The organic EL device of Example 19 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to one of the compounds listed in Table 10 to form the first light-emitting layer.
[0601] [Comparative Example 19-1] The organic EL element of Comparative Example 19-1 was manufactured in the same manner as in Example 19, except that, as shown in Table 10, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0602] [Comparative Example 19-2] The organic EL element of Comparative Example 19-2 was manufactured in the same manner as in Example 19, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 10.
[0603] [Comparative Examples 19-3, 19-4, and 19-5] The organic EL elements of Comparative Examples 19-3, 19-4, and 19-5 were manufactured in the same manner as in Example 19, except that the compounds used in the first and second light-emitting layers of Example 19 were replaced with the compounds listed in Table 10 to form the first and second light-emitting layers.
[0604] <Fabrication of Organic EL Device 20> [Example 20] The organic EL device of Example 20 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to one of the compounds listed in Table 10 to form the first light-emitting layer.
[0605] [Comparative Example 20-1] The organic EL element of Comparative Example 20-1 was manufactured in the same manner as in Example 20, except that, as shown in Table 10, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0606] [Comparative Example 20-2] The organic EL element of Comparative Example 20-2 was manufactured in the same manner as in Example 20, except that, as shown in Table 10, a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer.
[0607] [Comparative Examples 20-3, 20-4, and 20-5] The organic EL elements of Comparative Examples 20-3, 20-4, and 20-5 were manufactured in the same manner as in Example 20, except that the compounds used in the first and second light-emitting layers of Example 20 were replaced with the compounds listed in Table 10, as shown in Table 10, to form the first and second light-emitting layers.
[0608] <Fabrication of Organic EL Device 21> [Example 21] The organic EL device of Example 21 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to one of the compounds listed in Table 11 to form the first light-emitting layer.
[0609] [Comparative Example 21-1] The organic EL element of Comparative Example 21-1 was manufactured in the same manner as in Example 21, except that, as shown in Table 11, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0610] [Comparative Example 21-2] The organic EL element of Comparative Example 21-2 was manufactured in the same manner as in Example 21, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 11.
[0611] [Comparative Examples 21-3, 21-4, and 21-5] The organic EL elements of Comparative Examples 21-3, 21-4, and 21-5 were manufactured in the same manner as in Example 21, except that the compounds used in the first and second light-emitting layers of Example 21 were replaced with the compounds listed in Table 11 to form the first and second light-emitting layers.
[0612] <Fabrication of Organic EL Device 22> [Example 22] The organic EL device of Example 22 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to one of the compounds listed in Table 11 to form the first light-emitting layer.
[0613] [Comparative Example 22-1] The organic EL element of Comparative Example 22-1 was manufactured in the same manner as in Example 22, except that, as shown in Table 11, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0614] [Comparative Example 22-2] The organic EL element of Comparative Example 22-2 was manufactured in the same manner as in Example 22, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 11.
[0615] [Comparative Examples 22-3, 22-4, and 22-5] The organic EL elements of Comparative Examples 22-3, 22-4, and 22-5 were manufactured in the same manner as in Example 22, except that the compounds used in the first and second light-emitting layers of Example 22 were replaced with the compounds listed in Table 11, and the first and second light-emitting layers were formed accordingly.
[0616] <Fabrication of Organic EL Device 23> [Example 23] The organic EL device of Example 23 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 12 to form the first light-emitting layer.
[0617] [Comparative Example 23-1] The organic EL element of Comparative Example 23-1 was manufactured in the same manner as in Example 23, except that, as shown in Table 12, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0618] [Comparative Example 23-2] The organic EL element of Comparative Example 23-2 was manufactured in the same manner as in Example 23, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 12.
[0619] [Comparative Examples 23-3, 23-4, and 23-5] The organic EL elements of Comparative Examples 23-3, 23-4, and 23-5 were manufactured in the same manner as in Example 23, except that the compounds used in the first and second light-emitting layers of Example 23 were replaced with the compounds listed in Table 12, as shown in Table 12, to form the first and second light-emitting layers.
[0620] <Fabrication of Organic EL Device 24> [Example 24] The organic EL device of Example 24 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 12 to form the first light-emitting layer.
[0621] [Comparative Example 24-1] The organic EL element of Comparative Example 24-1 was manufactured in the same manner as in Example 24, except that, as shown in Table 12, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0622] [Comparative Example 24-2] The organic EL element of Comparative Example 24-2 was manufactured in the same manner as in Example 24, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 12.
[0623] [Comparative Examples 24-3, 24-4, and 24-5] The organic EL elements of Comparative Examples 24-3, 24-4, and 24-5 were manufactured in the same manner as in Example 24, except that the compounds used in the first and second light-emitting layers of Example 24 were replaced with the compounds listed in Table 12, as shown in Table 12, to form the first and second light-emitting layers.
[0624] <Fabrication of Organic EL Device 25> [Example 25] The organic EL device of Example 25 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 13 to form the first light-emitting layer.
[0625] [Comparative Example 25-1] The organic EL element of Comparative Example 25-1 was manufactured in the same manner as in Example 25, except that, as shown in Table 13, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0626] [Comparative Example 25-2] The organic EL element of Comparative Example 25-2 was manufactured in the same manner as in Example 25, except that, as shown in Table 13, a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer.
[0627] [Comparative Examples 25-3, 25-4, and 25-5] The organic EL elements of Comparative Examples 25-3, 25-4, and 25-5 were manufactured in the same manner as in Example 25, except that the compounds used in the first and second light-emitting layers of Example 25 were replaced with the compounds listed in Table 13, as shown in Table 13, to form the first and second light-emitting layers.
[0628] <Fabrication of Organic EL Device 26> [Example 26] The organic EL device of Example 26 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 13 to form the first light-emitting layer.
[0629] [Comparative Example 26-1] The organic EL element of Comparative Example 26-1 was manufactured in the same manner as in Example 26, except that, as shown in Table 13, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0630] [Comparative Example 26-2] The organic EL element of Comparative Example 26-2 was manufactured in the same manner as in Example 26, except that, as shown in Table 13, a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer.
[0631] [Comparative Examples 26-3, 26-4, and 26-5] The organic EL elements of Comparative Examples 26-3, 26-4, and 26-5 were manufactured in the same manner as in Example 26, except that the compounds used in the first and second light-emitting layers of Example 26 were replaced with the compounds listed in Table 13, as shown in Table 13, to form the first and second light-emitting layers.
[0632] <Fabrication of Organic EL Device 27> [Example 27] The organic EL device of Example 27 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 14 to form the first light-emitting layer.
[0633] [Comparative Example 27-1] The organic EL element of Comparative Example 27-1 was manufactured in the same manner as in Example 27, except that, as shown in Table 14, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0634] [Comparative Example 27-2] The organic EL element of Comparative Example 27-2 was manufactured in the same manner as in Example 27, except that, as shown in Table 14, a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer.
[0635] [Comparative Examples 27-3, 27-4, and 27-5] The organic EL elements of Comparative Examples 27-3, 27-4, and 27-5 were manufactured in the same manner as in Example 27, except that the compounds used in the first and second light-emitting layers of Example 27 were replaced with the compounds listed in Table 14, as shown in Table 14, to form the first and second light-emitting layers.
[0636] <Fabrication of Organic EL Device 28> [Example 28] The organic EL device of Example 28 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 14 to form the first light-emitting layer.
[0637] [Comparative Example 28-1] The organic EL element of Comparative Example 28-1 was manufactured in the same manner as in Example 28, except that, as shown in Table 14, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0638] [Comparative Example 28-2] The organic EL element of Comparative Example 28-2 was manufactured in the same manner as in Example 28, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 14.
[0639] [Comparative Examples 28-3, 28-4, and 28-5] The organic EL elements of Comparative Examples 28-3, 28-4, and 28-5 were manufactured in the same manner as in Example 28, except that the compounds used in the first and second light-emitting layers of Example 28 were replaced with the compounds listed in Table 14, and the first and second light-emitting layers were formed accordingly.
[0640] <Fabrication of Organic EL Device 29> [Example 29] The organic EL device of Example 29 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 15 to form the first light-emitting layer.
[0641] [Comparative Example 29-1] The organic EL element of Comparative Example 29-1 was manufactured in the same manner as in Example 29, except that, as shown in Table 15, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0642] [Comparative Example 29-2] The organic EL element of Comparative Example 29-2 was manufactured in the same manner as in Example 29, except that, as shown in Table 15, a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer.
[0643] [Comparative Examples 29-3, 29-4, and 29-5] The organic EL elements of Comparative Examples 29-3, 29-4, and 29-5 were manufactured in the same manner as in Example 29, except that the compounds used in the first and second light-emitting layers of Example 29 were replaced with the compounds listed in Table 15, as shown in Table 15, to form the first and second light-emitting layers.
[0644] <Fabrication of Organic EL Device 30> [Example 30] The organic EL device of Example 30 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 15 to form the first light-emitting layer.
[0645] [Comparative Example 30-1] The organic EL element of Comparative Example 30-1 was manufactured in the same manner as in Example 30, except that, as shown in Table 15, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0646] [Comparative Example 30-2] The organic EL element of Comparative Example 30-2 was manufactured in the same manner as in Example 30, except that, as shown in Table 15, a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer.
[0647] [Comparative Examples 30-3, 30-4, and 30-5] The organic EL elements of Comparative Examples 30-3, 30-4, and 30-5 were manufactured in the same manner as in Example 30, except that the compounds used in the first and second light-emitting layers of Example 30 were replaced with the compounds listed in Table 15, as shown in Table 15, to form the first and second light-emitting layers.
[0648] <Fabrication of Organic EL Device 31> [Example 31] The organic EL device of Example 31 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to one of the compounds listed in Table 16 to form the first light-emitting layer.
[0649] [Comparative Example 31-1] The organic EL element of Comparative Example 31-1 was manufactured in the same manner as in Example 31, except that, as shown in Table 16, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0650] [Comparative Example 31-2] The organic EL element of Comparative Example 31-2 was manufactured in the same manner as in Example 31, except that, as shown in Table 16, a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer.
[0651] [Comparative Examples 31-3, 31-4, and 31-5] The organic EL elements of Comparative Examples 31-3, 31-4, and 31-5 were manufactured in the same manner as in Example 31, except that the compounds used for the first and second light-emitting layers in Example 31 were replaced with the compounds listed in Table 16 to form the first and second light-emitting layers.
[0652] <Fabrication of Organic EL Device 32> [Example 32] The organic EL device of Example 32 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to one of the compounds listed in Table 16 to form the first light-emitting layer.
[0653] [Comparative Example 32-1] The organic EL element of Comparative Example 32-1 was manufactured in the same manner as in Example 32, except that, as shown in Table 16, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0654] [Comparative Example 32-2] The organic EL element of Comparative Example 32-2 was manufactured in the same manner as in Example 32, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 16.
[0655] [Comparative Examples 32-3, 32-4, and 32-5] The organic EL elements of Comparative Examples 32-3, 32-4, and 32-5 were manufactured in the same manner as in Example 32, except that the compounds used in the first and second light-emitting layers of Example 32 were replaced with the compounds listed in Table 16, and the first and second light-emitting layers were formed accordingly.
[0656] <Fabrication of Organic EL Device 33> [Example 33] The organic EL device of Example 33 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 17 to form the first light-emitting layer.
[0657] [Comparative Example 33-1] The organic EL element of Comparative Example 33-1 was manufactured in the same manner as in Example 33, except that, as shown in Table 17, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0658] [Comparative Example 33-2] The organic EL element of Comparative Example 33-2 was manufactured in the same manner as in Example 33, except that, as shown in Table 17, a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer.
[0659] [Comparative Examples 33-3, 33-4, and 33-5] The organic EL elements of Comparative Examples 33-3, 33-4, and 33-5 were manufactured in the same manner as in Example 33, except that the compounds used in the first and second light-emitting layers of Example 33 were replaced with the compounds listed in Table 17, as shown in Table 17, to form the first and second light-emitting layers.
[0660] <Fabrication of Organic EL Device 34> [Example 34] The organic EL device of Example 34 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to one of the compounds listed in Table 17 to form the first light-emitting layer.
[0661] [Comparative Example 34-1] The organic EL element of Comparative Example 34-1 was manufactured in the same manner as in Example 34, except that, as shown in Table 17, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0662] [Comparative Example 34-2] The organic EL element of Comparative Example 34-2 was manufactured in the same manner as in Example 34, except that, as shown in Table 17, a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer.
[0663] [Comparative Examples 34-3, 34-4, and 34-5] The organic EL elements of Comparative Examples 34-3, 34-4, and 34-5 were manufactured in the same manner as in Example 34, except that the compounds used in the first and second light-emitting layers of Example 34 were replaced with the compounds listed in Table 17, as shown in Table 17, to form the first and second light-emitting layers.
[0664] <Fabrication of Organic EL Device 35> [Example 35] The organic EL device of Example 35 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to one of the compounds listed in Table 18 to form the first light-emitting layer.
[0665] [Comparative Example 35-1] The organic EL element of Comparative Example 35-1 was manufactured in the same manner as in Example 35, except that, as shown in Table 18, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0666] [Comparative Example 35-2] The organic EL element of Comparative Example 35-2 was manufactured in the same manner as in Example 35, except that, as shown in Table 18, a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer.
[0667] [Comparative Examples 35-3, 35-4, and 35-5] The organic EL elements of Comparative Examples 35-3, 35-4, and 35-5 were manufactured in the same manner as in Example 35, except that the compounds used in the first and second light-emitting layers of Example 35 were replaced with the compounds listed in Table 18, as shown in Table 18, to form the first and second light-emitting layers.
[0668] <Fabrication of Organic EL Device 36> [Example 36] The organic EL device of Example 36 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 18 to form the first light-emitting layer.
[0669] [Comparative Example 36-1] The organic EL element of Comparative Example 36-1 was manufactured in the same manner as in Example 36, except that, as shown in Table 18, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0670] [Comparative Example 36-2] The organic EL element of Comparative Example 36-2 was manufactured in the same manner as in Example 36, except that, as shown in Table 18, a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer.
[0671] [Comparative Examples 36-3, 36-4, and 36-5] The organic EL elements of Comparative Examples 36-3, 36-4, and 36-5 were manufactured in the same manner as in Example 36, except that the compounds used in the first and second light-emitting layers of Example 36 were replaced with the compounds listed in Table 18, as shown in Table 18, to form the first and second light-emitting layers.
[0672] <Fabrication of Organic EL Device 37> [Example 37] The organic EL device of Example 37 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 19 to form the first light-emitting layer.
[0673] [Comparative Example 37-1] The organic EL element of Comparative Example 37-1 was manufactured in the same manner as in Example 37, except that, as shown in Table 19, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0674] [Comparative Example 37-2] The organic EL element of Comparative Example 37-2 was manufactured in the same manner as in Example 37, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 19.
[0675] [Comparative Examples 37-3, 37-4, and 37-5] The organic EL elements of Comparative Examples 37-3, 37-4, and 37-5 were manufactured in the same manner as in Example 37, except that the compounds used in the first and second light-emitting layers of Example 37 were replaced with the compounds listed in Table 19 to form the first and second light-emitting layers.
[0676] <Fabrication of Organic EL Device 38> [Example 38] The organic EL device of Example 38 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 19 to form the first light-emitting layer.
[0677] [Comparative Example 38-1] The organic EL element of Comparative Example 38-1 was manufactured in the same manner as in Example 38, except that, as shown in Table 19, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0678] [Comparative Example 38-2] The organic EL element of Comparative Example 38-2 was manufactured in the same manner as in Example 38, except that, as shown in Table 19, a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer.
[0679] [Comparative Examples 38-3, 38-4, and 38-5] The organic EL elements of Comparative Examples 38-3, 38-4, and 38-5 were manufactured in the same manner as in Example 38, except that the compounds used in the first and second light-emitting layers of Example 38 were replaced with the compounds listed in Table 19 to form the first and second light-emitting layers.
[0680] <Fabrication of Organic EL Device 39> [Example 39] The organic EL device of Example 39 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to one of the compounds listed in Table 20 to form the first light-emitting layer.
[0681] [Comparative Example 39-1] The organic EL element of Comparative Example 39-1 was manufactured in the same manner as in Example 39, except that, as shown in Table 20, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0682] [Comparative Example 39-2] The organic EL element of Comparative Example 39-2 was manufactured in the same manner as in Example 39, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 20.
[0683] [Comparative Examples 39-3, 39-4, and 39-5] The organic EL elements of Comparative Examples 39-3, 39-4, and 39-5 were manufactured in the same manner as in Example 39, except that the compounds used in the first and second light-emitting layers of Example 39 were replaced with the compounds listed in Table 20, as shown in Table 20, to form the first and second light-emitting layers.
[0684] <Fabrication of Organic EL Device 40> [Example 40] The organic EL device of Example 40 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 20 to form the first light-emitting layer.
[0685] [Comparative Example 40-1] The organic EL element of Comparative Example 40-1 was manufactured in the same manner as in Example 40, except that, as shown in Table 20, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0686] [Comparative Example 40-2] The organic EL element of Comparative Example 40-2 was manufactured in the same manner as in Example 40, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 20.
[0687] [Comparative Examples 40-3, 40-4, and 40-5] The organic EL elements of Comparative Examples 40-3, 40-4, and 40-5 were manufactured in the same manner as in Example 40, except that the compounds used in the first and second light-emitting layers of Example 40 were replaced with the compounds listed in Table 20, as shown in Table 20, to form the first and second light-emitting layers.
[0688] <Fabrication of Organic EL Device 41> [Example 41] The organic EL device of Example 41 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 21 to form the first light-emitting layer.
[0689] [Comparative Example 41-1] The organic EL element of Comparative Example 41-1 was manufactured in the same manner as in Example 41, except that, as shown in Table 21, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0690] [Comparative Example 41-2] The organic EL element of Comparative Example 41-2 was manufactured in the same manner as in Example 41, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 21.
[0691] [Comparative Examples 41-3, 41-4, and 41-5] The organic EL elements of Comparative Examples 41-3, 41-4, and 41-5 were manufactured in the same manner as in Example 41, except that the compounds used in the first and second light-emitting layers of Example 41 were replaced with the compounds listed in Table 21 to form the first and second light-emitting layers.
[0692] <Fabrication of Organic EL Device 42> [Example 42] The organic EL device of Example 42 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 21 to form the first light-emitting layer.
[0693] [Comparative Example 42-1] The organic EL element of Comparative Example 42-1 was manufactured in the same manner as in Example 42, except that, as shown in Table 21, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0694] [Comparative Example 42-2] The organic EL element of Comparative Example 42-2 was manufactured in the same manner as in Example 42, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 21.
[0695] [Comparative Examples 42-3, 42-4, and 42-5] The organic EL elements of Comparative Examples 42-3, 42-4, and 42-5 were manufactured in the same manner as in Example 42, except that the compounds used in the first and second light-emitting layers of Example 42 were replaced with the compounds listed in Table 21, and the first and second light-emitting layers were formed accordingly.
[0696] <Fabrication of Organic EL Device 43> [Example 43] The organic EL device of Example 43 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 22 to form the first light-emitting layer.
[0697] [Comparative Example 43-1] The organic EL element of Comparative Example 43-1 was manufactured in the same manner as in Example 43, except that, as shown in Table 22, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0698] [Comparative Example 43-2] The organic EL element of Comparative Example 43-2 was manufactured in the same manner as in Example 43, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 22.
[0699] [Comparative Examples 43-3, 43-4, and 43-5] The organic EL elements of Comparative Examples 43-3, 43-4, and 43-5 were manufactured in the same manner as in Example 43, except that the compounds used in the first and second light-emitting layers of Example 43 were replaced with the compounds listed in Table 22, as shown in Table 22, to form the first and second light-emitting layers.
[0700] <Fabrication of Organic EL Device 44> [Example 44] The organic EL device of Example 44 was fabricated in the same manner as in Example 1, except that the compound used for the first light-emitting layer in Example 1 was changed to the compound listed in Table 22, and the first light-emitting layer was formed in the same manner as in Example 1.
[0701] [Comparative Example 44-1] The organic EL element of Comparative Example 44-1 was manufactured in the same manner as in Example 44, except that, as shown in Table 22, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0702] [Comparative Example 44-2] The organic EL element of Comparative Example 44-2 was manufactured in the same manner as in Example 44, except that a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 22.
[0703] [Comparative Examples 44-3, 44-4, and 44-5] The organic EL elements of Comparative Examples 44-3, 44-4, and 44-5 were manufactured in the same manner as in Example 44, except that the compounds used in the first and second light-emitting layers of Example 44 were replaced with the compounds listed in Table 22, as shown in Table 22, to form the first and second light-emitting layers.
[0704] <Fabrication of Organic EL Device 45> [Example 45] The organic EL device of Example 45 was fabricated in the same manner as in Example 1, except that the compounds used for the first and second light-emitting layers in Example 1 were changed to the compounds listed in Table 23, and the first and second light-emitting layers were formed in the same manner as in Example 1.
[0705] [Comparative Example 45-1] The organic EL element of Comparative Example 45-1 was manufactured in the same manner as in Example 45, except that, as shown in Table 23, a second light-emitting layer with a thickness of 30 nm was formed by co-depositing compound BH2-2 (second host material) and compound BD-1 (second dopant material) on the second hole transport layer without forming a first light-emitting layer.
[0706] [Comparative Example 45-2] The organic EL element of Comparative Example 45-2 was manufactured in the same manner as in Example 45, except that, as shown in Table 23, a second light-emitting layer with a thickness of 30 nm was formed on the second hole transport layer without forming the first light-emitting layer.
[0707] [Comparative Examples 45-3, 45-4, and 45-5] The organic EL elements of Comparative Examples 45-3, 45-4, and 45-5 were manufactured in the same manner as in Example 45, except that the compounds used in the first and second light-emitting layers of Example 45 were replaced with the com...
Claims
1. An organic electroluminescent element comprising: an anode; a cathode; and a light-emitting band disposed between the anode and the cathode, wherein the anode, the light-emitting band, and the cathode are arranged in this order; the light-emitting band includes a first light-emitting layer and a second light-emitting layer; the first light-emitting layer contains a first host material and a first dopant material; the second light-emitting layer contains a second host material and a second dopant material; the first host material and the second host material are different from each other; the first dopant material is a light-emitting compound with a maximum peak wavelength of 500 nm or less; the second dopant material is a light-emitting compound with a maximum peak wavelength of 500 nm or less; the first dopant material and the second dopant material are different from each other; and the triplet energy T of the first host material 1 (H1) and the triplet energy T of the second host material 1 An organic electroluminescent element in which (H2) and satisfy the relationship shown in the following formula (Equation 1), and the first dopant material HOMO(D1) and the second dopant material HOMO(D2) satisfy the relationship shown in the following formula (Equation 2C). 1 (H1)>T 1 (H2)...(Math. 1) HOMO(D1)-HOMO(D2)>0.25eV...(Math. 2C) 2. An organic electroluminescent element according to claim 1, wherein the HOMO(H2) of the second host material and the HOMO(D2) of the second dopant material satisfy the following relationship (Equation 3C): HOMO(D2) - HOMO(H2) < 0.50 eV ... (Equation 3C) 3. In the organic electroluminescent element according to claim 1 or claim 2, the singlet energy S of the first host material 1 (H1) and the singlet energy S of the first dopant material 1 An organic electroluminescent element in which (D1) and satisfies the relationship shown in the following equation (Equation 2). 1 (H1) > S 1 (D1) ... (Math 2) 4. The organic electroluminescent element according to any one of claims 1 to 3, wherein the triplet energy T of the first host material 1 (H1) and the triplet energy T of the first dopant material 1 (D1) satisfy the relationship of the following mathematical formula (Formula 2A): An organic electroluminescent element. T 1 (D1) > T 1 (H1) ... (Formula 2A) 5. An organic electroluminescent element according to any one of claims 1 to 4, wherein the singlet energy S of the second host material 1 (H2) and the singlet energy S of the second dopant material. 1 An organic electroluminescent element in which (D2) and satisfies the relationship shown in the following equation (Equation 4). 1 (H2) > S 1 (D2) ... (Math 4) 6. An organic electroluminescent element according to any one of claims 1 to 5, wherein the triplet energy T of the second host material 1 (D2) and the triplet energy T of the second dopant material. 1 An organic electroluminescent element in which (H2) and satisfies the relationship shown in the following formula (Equation 3). 1 (D2) > T 1 (H2) ... (Math 3) 7. An organic electroluminescent element according to any one of claims 1 to 6, wherein the triplet energy T of the first dopant material or the second dopant material 1 (DX) and the triplet energy T of the first host material. 1 (H1) and the triplet energy T of the second host material 1 An organic electroluminescent element in which (H2) and satisfies the following relationship (equation 10X): 2.7 eV > T 1 (DX) > T 1 (H1)>T 1 (H2) ... (Number 10X) 8. An organic electroluminescent element according to any one of claims 1 to 7, wherein the triplet energy T of the first dopant material or the second dopant material 1 (DX) and the triplet energy T of the first host material. 1 An organic electroluminescent element in which (H1) and satisfies the following relationship (Equation 11X): 0 eV < T 1 (DX)-T 1 (H1) < 0.7eV ... (Equation 11X) 9. An organic electroluminescent element according to any one of claims 1 to 8, wherein the first dopant material is not a complex.
10. An organic electroluminescent element according to any one of claims 1 to 9, wherein the first dopant material is a compound containing one or more boron atoms.
11. An organic electroluminescent element according to any one of claims 1 to 10, wherein the first dopant material is contained in the first light-emitting layer in an amount exceeding 1.0% by mass.
12. An organic electroluminescent element according to any one of claims 1 to 11, wherein the second dopant material is not a complex.
13. An organic electroluminescent element according to any one of claims 1 to 12, wherein the second dopant material is a compound containing one or more boron atoms.
14. An organic electroluminescent element according to any one of claims 1 to 13, wherein the second dopant material is contained in the second light-emitting layer in an amount exceeding 1.0% by mass.
15. An organic electroluminescent element according to any one of claims 1 to 14, wherein the electron mobility μe(H1) of the first host material and the electron mobility μe(H2) of the second host material satisfy the following relationship (Equation 30): μe(H2) > μe(H1) ... (Equation 30) 16. An organic electroluminescent element according to any one of claims 1 to 15, wherein the triplet energy T of the first host material 1 (H1) and the triplet energy T of the second host material. 1 An organic electroluminescent element in which (H2) and satisfies the relationship shown in the following equation (Equation 5). 1 (H1)-T 1 (H2) > 0.03 eV ... (Math 5) 17. An organic electroluminescent element according to any one of claims 1 to 16, wherein the triplet energy T of the first host material 1 (H1) is an organic electroluminescent element that satisfies the relationship in the following equation (Equation 12). 1 (H1) > 2.0 eV ... (Math 12) 18. An organic electroluminescent element according to any one of claims 1 to 17, wherein the triplet energy T of the second host material 1 (H2) is an organic electroluminescent element that satisfies the following equation (Equation 14): 1.9 eV ≥ T 1 (H2) ... (Number 14) 19. An organic electroluminescent element according to any one of claims 1 to 18, wherein the first dopant material HOMO(D1) and the second dopant material HOMO(D2) satisfy the following equation (Equation 21): HOMO(D1) - HOMO(D2) ≥ 0.28 eV …(Equation 21) 20. An organic electroluminescent element according to any one of claims 1 to 19, wherein the first dopant material HOMO(D1) and the second dopant material HOMO(D2) satisfy the following relationship (Equation 22): HOMO(D1) - HOMO(D2) ≤ 0.50 eV …(Equation 22) 21. An organic electroluminescent element according to any one of claims 1 to 20, wherein the first light-emitting layer does not contain a metal complex.
22. An organic electroluminescent element according to any one of claims 1 to 21, wherein the second light-emitting layer does not contain a metal complex.
23. An organic electroluminescent element according to any one of claims 1 to 22, wherein the thickness of the first light-emitting layer is 3 nm or more and 15 nm or less.
24. An organic electroluminescent element according to any one of claims 1 to 23, wherein the thickness of the second light-emitting layer is 5 nm or more and 25 nm or less.
25. An organic electroluminescent element according to any one of claims 1 to 24, wherein the first light-emitting layer and the second light-emitting layer are in direct contact.
26. An organic electroluminescent element according to any one of claims 1 to 25, wherein the first light-emitting layer is included between the anode and the cathode, and the second light-emitting layer is included between the first light-emitting layer and the cathode.
27. An organic electroluminescent element according to any one of claims 1 to 26, wherein the first light-emitting layer emits light having a maximum peak wavelength of 500 nm or less when the element is driven.
28. An organic electroluminescent element according to any one of claims 1 to 27, wherein the second light-emitting layer emits light having a maximum peak wavelength of 500 nm or less when the element is driven.
29. An organic electroluminescent element according to any one of claims 1 to 28, wherein the organic electroluminescent element emits light with a maximum peak wavelength of 500 nm or less when the element is driven.
30. An electronic device equipped with an organic electroluminescent element according to any one of claims 1 to 29.