Organic electroluminescent elements and electronic devices
The organic electroluminescent element with a structured arrangement of light-emitting units and specific host materials addresses performance limitations, improving brightness and efficiency and extending the lifespan of the device.
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- IDEMITSU KOSAN CO LTD
- Filing Date
- 2024-12-26
- Publication Date
- 2026-07-08
AI Technical Summary
Existing organic electroluminescent elements require further performance improvements in brightness, emission wavelength, chromaticity, luminous efficiency, and lifespan.
An organic electroluminescent element with a specific arrangement of light-emitting units, including a first and second light-emitting unit, each containing distinct host materials, and adhering to triplet energy conditions to enhance performance.
The solution provides an organic electroluminescent element with improved performance, enhancing brightness and efficiency while extending the lifespan of the device.
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Figure 2026114822000001_ABST
Abstract
Description
[Technical Field]
[0001] This invention relates to organic electroluminescent elements and electronic devices. [Background technology]
[0002] Organic electroluminescent elements (hereinafter sometimes referred to as "organic EL elements") are used in full-color displays. 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%. When singlet excitons return to the ground state, they release energy as fluorescence, and when triplet excitons return to the ground state, they release energy as phosphorescence. Various studies are being conducted on the compounds and device structures used in organic EL elements to improve their performance. Examples of organic EL element performance include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan. For example, Patent Document 1 describes a tandem-type organic EL element having a stacked light-emitting unit that includes a first light-emitting layer and a second light-emitting layer. [Prior art documents] [Patent Documents]
[0003] [Patent Document 1] International Publication No. 2021 / 162057 [Overview of the project] [Problems that the invention aims to solve]
[0004] Although various studies have been conducted on compounds and device structures used in organic EL elements, further performance improvements are required for organic EL elements. The object of the present invention is to provide an organic electroluminescent element with improved element performance, and to provide an electronic device equipped with the organic electroluminescent element. [Means for solving the problem]
[0005] According to one aspect of the present invention, an organic electroluminescent element, The organic electroluminescent element comprises an anode, a cathode, and two or more light-emitting units disposed between the anode and the cathode. The two or more light-emitting units include at least a first light-emitting unit having a first light-emitting band and a second light-emitting unit having a second light-emitting band. The anode, the first light-emitting unit, the second light-emitting unit, and the cathode are arranged in this order from the anode side toward the cathode side. The first light-emitting band includes a first light-emitting layer containing a first host material and a second light-emitting layer containing a second host material. The first light-emitting layer is positioned closer to the anode than the second light-emitting layer. The second emission band includes a third emission layer containing a third host material and a fourth emission layer containing a fourth host material. The third light-emitting layer is positioned closer to the anode than the fourth light-emitting layer. The first light-emitting layer, the second light-emitting layer, the third light-emitting layer, and the fourth light-emitting layer each independently contain a light-emitting compound that exhibits light emission with a maximum peak wavelength of 500 nm or less. The first host material and the third host material are different from each other. Unlike the second and fourth host materials, the first host material is The third host material differs from the second host material and the fourth host material, The second host material and the fourth host material are either identical or different from each other. The triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material satisfy the following equation (Equation 1), The triplet energy T1(H3) of the third host material and the triplet energy T1(H4) of the fourth host material satisfy the following equation (Equation 2): An organic electroluminescent element is provided. T1(H1)>T1(H2) …(Math 1) T1(H3)>T1(H4) …(Math 2)
[0006] According to one aspect of the present invention, an electronic device is provided that incorporates an organic electroluminescent element according to one aspect of the present invention. [Effects of the Invention]
[0007] According to one aspect of the present invention, an organic electroluminescent element with improved performance can be provided. Furthermore, according to one aspect of the present invention, an electronic device equipped with the organic electroluminescent element can be provided. [Brief explanation of the drawing]
[0008] [Figure 1] This figure shows a schematic configuration of an example of an organic electroluminescent element according to one embodiment of the present invention. [Modes for carrying out the invention]
[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 the "ring-forming carbon number" described below unless otherwise specified. For example, a benzene ring has 6 ring-forming carbon atoms, a naphthalene ring has 10 ring-forming carbon atoms, a pyridine ring has 5 ring-forming carbon atoms, and a furan ring has 4 ring-forming carbon atoms. Also, for example, the ring-forming carbon number of a 9,9-diphenylfluorenyl group is 13, and the ring-forming carbon number of a 9,9'-spirobifluorenyl group is 25. Furthermore, when a benzene ring is substituted with an alkyl group, for example, the number of carbon atoms in that alkyl group is not included in the number of ring-forming carbon atoms of the benzene ring. Therefore, the number of ring-forming carbon atoms in a benzene ring substituted with an alkyl group is 6. Similarly, when a naphthalene ring is substituted with an alkyl group, for example, 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 aggregates) (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 substituents, 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" represents 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 of XX to YY" means that "atom count XX to YY" represents 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", where "XX" is an integer of 1 or more, and "YY" is 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 "unsubstituted ZZ group," and a substituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is "substituted ZZ group." In this specification, "unsubstituted" in the context of a "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. Furthermore, in this specification, "substituted" in the context of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. Similarly, "substituted" in the context of "BB group substituted with AA group" means that one or more hydrogen atoms in the BB group are replaced by an AA group.
[0016] "Substituents as described herein" The substituents described herein will be explained below.
[0017] The number of ring-forming carbon atoms in the "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring-forming atoms in the "unsubstituted heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkyl group" as described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkenyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkynyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "unsubstituted cycloalkyl groups" described herein is 3 to 50, preferably 3 to 20, and 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] • "substituted or unsubstituted aryl groups" Specific examples of "substituted or unsubstituted aryl groups" as described herein (Specific Examples Group G1) include the following unsubstituted aryl groups (Specific Examples Group G1A) and substituted aryl groups (Specific Examples Group G1B), etc. (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, the term "aryl group" simply includes both "unsubstituted aryl groups" and "substituted aryl groups." A "substituted aryl group" refers to 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 groups in which one or more hydrogen atoms of an "unsubstituted aryl group" in specific example group G1A below are replaced by substituents, and the examples of substituted aryl groups in specific example group G1B below. Note that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and 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 group" in specific example group G1B below are further replaced by substituents, and groups in which the hydrogen atoms of the substituent in the "substituted aryl group" in specific example 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, Chrysenyl group, Benzocrisenyl group, Triphenylenyl group, benzotriphenylenyl group, Tetraceryl group, Pentacenyl group, Fluorenyl group, 9,9'-Spirobifluorenyl group, Benzofluorenyl group, Dibenzofluorenyl group, Fluoranthenyl group, Benzofluoranthenyl group, Perilenyl group, and A monovalent aryl group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).
[0020] [ka]
[0021] [ka]
[0022] • Substitutive aryl groups (Specific examples group G1B): o-Tryl group, m-tolyl group, p-tril group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, Meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, Cyanophenyl group, Triphenylsilylphenyl group, Trimethylsilylphenyl group, Phenylnaphthyl group, Naphthylphenyl group, and A group obtained by replacing one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the general formulas (TEMP-1) to (TEMP-15) above with substituents.
[0023] • "Substitutable or unsubstituted heterocyclic groups" The “heterocyclic group” as described herein is a cyclic group containing at least one heteroatom in its ring-forming atoms. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron. The "heterocyclic group" as described herein is either a monocyclic group or a fused-cyclic group. The term "heterocyclic group" as used herein refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples of "substituted or unsubstituted heterocyclic groups" as described herein (Specific Examples Group G2) include the following unsubstituted heterocyclic groups (Specific Examples Group G2A) and substituted heterocyclic groups (Specific Examples Group G2B), etc. (Here, "unsubstituted heterocyclic group" refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group," and "substituted heterocyclic group" refers to the case where "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group.") In this specification, the term "heterocyclic group" simply includes both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups." A "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by substituents. Specific examples of "substituted heterocyclic groups" include the groups in specific example group G2A below in which hydrogen atoms of an "unsubstituted heterocyclic group" are replaced, and the examples of substituted heterocyclic groups in specific example group G2B below. Note that 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 hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself are further replaced by substituents, and groups in which hydrogen atoms of substituents are further replaced by substituents.
[0024] The specific examples group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).
[0025] Specific examples group G2B includes, for example, 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 a nitrogen atom (specific examples group G2A1): Pyrrolyl group, imidazolyl group, Pyrazolyl group, Triazolyl group, Tetrazolyl group, Oxazolyl group, isoxazolyl group, Oxadiazolyl group, Thiazolyl group, isothiazolyl group, Thiadianzolyl group, Pyridyl group, Pyridazinyl 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, Phenantridinyl group, Acridinyl group, Phenazinyl group, Carbazolyl group, Benzocarbazolyl group, Morpholino group, Phenoxadinyl group, Phenothiazinyl group, Azacarbazolyl group and diazacarbazolyl group.
[0027] • Unsubstituted heterocyclic groups containing an oxygen atom (specific examples group G2A2): Frill group, Oxazolyl group, isoxazolyl group, Oxadiazolyl group, xanthenyl group, Benzofuranyl group, Isobenzofuranyl group, Dibenzofuranyl group, Naphthobenzofuranyl group, Benzoxazolyl group, Benzoisoxazolyl group, Phenoxadinyl group, Morpholino group, Dinaphthofuranyl group, Azadibenzofuranyl group, Diazadibenzofuranyl group, Azanaftobenzofuranyl group, and Diazanaphthobenzofuranyl group.
[0028] • Unsubstituted heterocyclic groups containing a sulfur atom (specific examples group G2A3): Thienyl group, Thiazolyl group, isothiazolyl group, Thiadianzolyl 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), Azanaphtobenzothiophenyl group (azanaphthobenzothienyl group), and Diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).
[0029] • 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):
[0030] [ka]
[0031] [ka]
[0032] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each of these is independently an oxygen atom, a sulfur atom, NH, or CH2. However, X A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH. In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A If at least one of the members is NH or CH2, the monovalent heterocyclic groups derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) include monovalent groups obtained by removing one hydrogen atom from these NH or CH2 members.
[0033] • Heterocyclic groups with substitutions containing a nitrogen atom (Specific examples group G2B1): (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-Naphthyl)carbazolyl group, Diphenylcarbazol-9-yl group, Phenylcarbazol-9-yl group, Methylbenzimidazolyl group, Ethylbenzimidazolyl group, Phenyltriazinyl group, Biphenylyltriazinyl group, Diphenyltriazinyl group, Phenylquinazolinyl group, and Biphenylylquinazolinyl group.
[0034] ·Substituted heterocyclic group containing an oxygen atom (specific example group G2B2): Phenyldibenzofuranyl group, Methyldibenzofuranyl group, t-Butyldibenzofuranyl group, and Monovalent residue of spiro[9H-xanthene-9,9’-[9H]fluorene].
[0035] ·Substituted heterocyclic group containing a sulfur atom (specific example group G2B3): Phenyldibenzothiophenyl group, Methyldibenzothiophenyl group, t-Butyldibenzothiophenyl group, and Monovalent residue of spiro[9H-thioxanthene-9,9’-[9H]fluorene].
[0036] ·A group in which one or more hydrogen atoms of the monovalent heterocyclic group derived from the ring structures represented by the general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific example group G2B4):
[0037] Said "one or more hydrogen atoms of the monovalent heterocyclic group" refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, X A and Y A when at least one of which is NH, a hydrogen atom bonded to a nitrogen atom, and X A and Y AThis refers to one or more hydrogen atoms selected from the hydrogen atoms of the methylene group when one of the atoms is CH2.
[0038] • "Substituted 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 "unsubstituted alkyl group," and "substituted alkyl group" refers to the case where "substituted or unsubstituted alkyl group" is "substituted alkyl group.") Hereafter, "alkyl group" simply refers to both "unsubstituted alkyl groups" and "substituted alkyl groups." A "substituted alkyl group" refers to 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 groups in which one or more hydrogen atoms in the "unsubstituted alkyl groups" (specific example group G3A) below are replaced by substituents, and examples of substituted alkyl groups (specific example group G3B). In this specification, the alkyl group in "unsubstituted alkyl group" refers to a linear alkyl group. Therefore, "unsubstituted alkyl groups" include both linear "unsubstituted alkyl groups" and branched "unsubstituted alkyl groups". The examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed here are merely examples, and the "substituted alkyl groups" described herein also include groups in which the hydrogen atoms of the alkyl group itself in the "substituted alkyl groups" of specific example group G3B are further replaced by substituents, and groups in which the hydrogen atoms of the substituent in the "substituted alkyl groups" of specific example group G3B 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] • "Substituted 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), etc. (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" refers to a group in which one or more hydrogen atoms of an "unsubstituted alkenyl group" are replaced by substituents. Specific examples of "substituted alkenyl groups" include groups in which the "unsubstituted alkenyl group" (Specific Example Group G4A) has 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 group" of Specific Example Group G4B are further replaced by substituents, and groups in which the hydrogen atoms of the substituent in the "substituted alkenyl group" 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] • Substitutive 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, "unsubstituted alkynyl group" refers to the case where "substituted or unsubstituted alkynyl group" is "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" refers to 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 groups in which one or more hydrogen atoms in an "unsubstituted alkynyl group" (specific example group G5A) are replaced by substituents.
[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), etc. (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, the term "cycloalkyl group" simply includes both "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups." A "substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced by a substituent. Specific examples of "substituted cycloalkyl groups" include the groups in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" (specific example group G6A) are replaced by a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed here are merely examples, and 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 a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted cycloalkyl group" of specific example group G6B are further replaced by a substituent.
[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] • Substituting cycloalkyl groups (specific examples group G6B): 4-methylcyclohexyl group.
[0049] · "-Si(R 901 )(R 902 )(R 903 ) represented by the base -Si(R 901 )(R 902 )(R 903 ) Examples of the base represented by (Example Group G7) are: -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 are some examples. G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6. In -Si(G1)(G1)(G1), the multiple G1s are either identical or different from one another. In -Si(G1)(G2)(G2), the multiple G2s are either identical or different from one another. In -Si(G1)(G1)(G2), the multiple G1s are either identical or different from one another. In -Si(G2)(G2)(G2), the multiple G2s are either identical or different from one another. In -Si(G3)(G3)(G3), the multiple G3s are either identical or different from one another. In -Si(G6)(G6)(G6), the multiple G6s are either identical or different from one another.
[0050] ·「-O-(R 904 ) represented by the base The following information pertains to the -O-(R904 ) Examples of the base represented by (Example Group G8) are: -O(G1), -O(G2), -O(G3), and -O(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6.
[0051] · "-S-(R 905 ) represented by the base The following information pertains to the -S-(R 905 ) Examples of the base represented by (Example Group G9) are: -S(G1), -S(G2), -S(G3), and -S(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6.
[0052] · "-N(R 906 )(R 907 ) represented by the base -N(R) as described in this specification 906 )(R 907 ) Examples of the base represented by (Example Group G10) are: -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6. In -N(G1)(G1), multiple G1s are either identical or different from one another. In -N(G2)(G2), multiple G2s are either identical or different from one another. In -N(G3)(G3), multiple G3s are either identical or different from one another. In -N(G6)(G6), multiple G6s are either identical or different from one another.
[0053] • "Halogen atom" Specific examples of "halogen atoms" as described herein (Specific Examples Group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.
[0054] • "Substituted or unsubstituted fluoroalkyl groups" The terms "substituted or unsubstituted fluoroalkyl groups" as used 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. A "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced by substituents. The terms "substituted fluoroalkyl groups" as used 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 the example of a group 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 terms "substituted or unsubstituted haloalkyl groups" as used 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. A "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of a "haloalkyl group" are replaced by substituents. The terms "substituted haloalkyl groups" as used 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 of the aforementioned "alkyl group" (specific example group G3) are replaced by halogen atoms. Haloalkyl groups are sometimes referred to as alkyl halogens.
[0056] • "Substituted or unsubstituted alkoxy groups" A specific example of a "substituted or unsubstituted alkoxy group" as described herein is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" as 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 groups" 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 groups" A specific example of a "substituted or unsubstituted aryloxy group" as described herein is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" as 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 groups" 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 groups" A specific example of the "trialkylsilyl group" described herein is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) are either identical or different from one another. Unless otherwise specified herein, 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.
[0061] • "Substituted or unsubstituted aralkyl groups" Specific examples of the "substituted or unsubstituted aralkyl group" described herein include the 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] [ka]
[0066] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically one of the following groups:
[0067] [ka]
[0068] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bond position.
[0069] In this specification, unless otherwise specified, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups:
[0070] [ka]
[0071] In the general formulas (TEMP-34) to (TEMP-41) above, * represents a 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 the "substituted or unsubstituted arylene group" (Specific Examples Group G12) include the divalent group 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 refer to 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 the 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 groups" Unless otherwise specified, the "substituted or unsubstituted alkylene groups" described herein are divalent groups derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl groups" described above. Specific examples of "substituted or unsubstituted alkylene groups" (Specific Examples Group G14) include the divalent groups derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl groups" 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] [ka]
[0078] [ka]
[0079] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each of these is independently either a hydrogen atom or a substituent. In the general formulas (TEMP-42) to (TEMP-52) above, * represents a bond position.
[0080] [ka]
[0081] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each of these is independently either a hydrogen atom or a substituent. Equations Q9 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) above, * represents a bond position.
[0082] [ka]
[0083] In the general formulas (TEMP-63) to (TEMP-68) above, Q1 to Q8 are each independently a hydrogen atom or a substituent. In the general formulas (TEMP-63) to (TEMP-68) above, * 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] [ka]
[0086] [ka]
[0087] [ka]
[0088] In the general formulas (TEMP-69) to (TEMP-82) above, Q1 to Q9 are each independently a hydrogen atom or a substituent.
[0089] [ka]
[0090] [ka]
[0091] [ka]
[0092] [ka]
[0093] In the general formulas (TEMP-83) to (TEMP-102) above, Q1 to Q8 are each independently 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, the phrase "one or more pairs of adjacent elements join together to form a substituted or unsubstituted monoring, join together to form a substituted or unsubstituted fused ring, or do not join together" means the case where "one or more pairs of adjacent elements join together to form a substituted or unsubstituted monoring," the case where "one or more pairs of adjacent elements join together to form a substituted or unsubstituted fused ring," and the case where "one or more pairs of adjacent elements do not join together." In this specification, the cases in which "one or more pairs of adjacent elements bond to each other to form a substituted or unsubstituted monoring" and "one or more pairs of adjacent elements bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "cases where elements bond to form a ring") will be explained below. An example will be given of an anthracene compound represented by the following general formula (TEMP-103), whose parent skeleton is an anthracene ring.
[0096] [ka]
[0097] For example, R921 ~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 pair, R 922 and R 923 The pair, R 923 and R 924 The pair, R 924 and R 930 The pair, R 930 and R 925 The pair, R 925 and R 926 The pair, R 926 and R 927 The pair, R 927 and R 928 The pair, R 928 and R 929 The pair with, and R 929 and R 921 They are a pair.
[0098] The phrase "one or more pairs" above means that two or more pairs of adjacent pairs may simultaneously form a ring. For example, R 921 and R 922 and are joined to form a ring Q A Forms R 925 and R 926 and are joined 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] [ka]
[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 form a ring Q A Forms R 922 and R923 and are joined to form a ring Q C It forms three adjacent (R 921 , R 922 and R 923 This refers to the case where a set consisting of ) is bonded to each other to form a ring and condenses onto the anthracene matrix skeleton, in which case the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C R 922 Share.
[0101] [ka]
[0102] The formed "mono-ring" or "condensed-ring" may be saturated or unsaturated, based solely on the structure of the formed ring. Even when "a pair of adjacent rings" forms a "mono-ring" or "condensed-ring," the "mono-ring" or "condensed-ring" can be saturated or unsaturated. For example, ring Q formed in the general formula (TEMP-104) A and ring Q B These are, respectively, a "single ring" or a "condensed ring". Also, ring Q formed in the general formula (TEMP-105) is A , and ring Q C This is a "condensed ring". The ring Q of the general formula (TEMP-105) A and Q C This refers to the Q environment. A and Q C The ring Q of the general formula (TMEP-104) is formed by the condensation of the two rings. A If it is a benzene ring, then ring Q A It is a single ring. The ring Q of the general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a condensed ring.
[0103] "Unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. "Saturated ring" means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of the aromatic hydrocarbon ring include structures in which the groups listed as specific examples in Specific Example Group G1 are terminated by hydrogen atoms. Specific examples of the aromatic heterocyclic ring include structures in which the aromatic heterocyclic groups listed as specific examples in Specific Example Group G2 are terminated by hydrogen atoms. Specific examples of the aliphatic hydrocarbon ring include structures in which the groups listed as specific examples in Specific Example Group G6 are terminated by hydrogen atoms. "Forming a ring" means forming a ring with only a plurality of atoms of the mother skeleton or with a plurality of atoms of the mother skeleton and one or more arbitrary elements. For example, in the general formula (TEMP-104), the ring Q formed by bonding R 921 and R 922 to each other means a ring formed by a carbon atom of the anthracene skeleton to which R A is bonded, a carbon atom of the anthracene skeleton to which R 921 is bonded, and one or more arbitrary elements. Specific examples include, when forming the ring Q 922 with R 921 and R 922 , when forming a monocyclic unsaturated ring with a carbon atom of the anthracene skeleton to which R A is bonded, a carbon atom of the anthracene skeleton to which R 921 is bonded, and four carbon atoms, the ring formed by R 922 and R 921 is a benzene ring. 922 Here, "arbitrary element" is preferably at least one element selected from the group consisting of carbon element, nitrogen element, oxygen element, and sulfur element, unless otherwise specified in this specification. In an arbitrary element (for example, in the case of a carbon element or a nitrogen element), a bond that does not form a ring may be terminated by a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described later. When an arbitrary element other than the carbon element is included, the formed ring is a heterocyclic ring. [[ID=*]] The "one or more arbitrary elements" constituting the monoring or fused ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5, unless otherwise specified herein. Unless otherwise specified herein, the preferred form is a "mono-ring" and a "condensed ring." Unless otherwise specified herein, the "unsaturated ring" is preferred over the "saturated ring". Unless otherwise specified herein, “monocyclic” is preferably a benzene ring. Unless otherwise specified herein, the “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] When the above-mentioned "monocyclic ring" or "fused ring" has substituents, the substituents are, for example, "any substituents" as described later. Specific examples of substituents when the above-mentioned "monocyclic ring" or "fused ring" has substituents are the substituents described in the section "Substituents as described herein" above. When the above-mentioned "saturated ring" or "unsaturated ring" has substituents, the substituents are, for example, "any substituents" as described later. Specific examples of substituents when the above-mentioned "mono-ring" or "fused ring" has substituents are the substituents described in the section "Substituents as described herein" above. The above explains the cases in which "one or more pairs of adjacent elements combine to form a substituted or unsubstituted monoring" and "one or more pairs of adjacent elements combine to form a substituted or unsubstituted fused ring" ("the case of combining to form a ring").
[0106] · Substituents in the case of "substituted or unsubstituted" In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (which may be referred to as "any substituent" in the present specification) is, for example, An unsubstituted alkyl group having 1 to 50 carbon atoms, An unsubstituted alkenyl group having 2 to 50 carbon atoms, An unsubstituted alkynyl group having 2 to 50 carbon atoms, An unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), A halogen atom, a cyano group, a nitro group, An unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and An unsubstituted heterocyclic group having 5 to 50 ring-forming atoms And groups selected from the group consisting of, etc., Here, R 901 ~R 907 Are each independently A hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. R 901 When two or more R 901 Exist, two or more R R 902 When two or more R 902 Exist, two or more R R903 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: Alkyl alkyl groups with 1 to 50 carbon atoms, A ring-forming aryl group with 6 to 50 carbon atoms, and Heterocyclic groups with 5 to 50 ring-forming atoms It is a group selected from the group consisting of the following.
[0108] In one embodiment, the substituent in the case of "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 18 carbon atoms, Ring-forming aryl groups with 6 to 18 carbon atoms, and Heterocyclic groups with 5 to 18 ring-forming atoms It is a group selected from the group consisting of the following.
[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, 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, such as those described above.
[0111] In this specification, a numerical range expressed using "AA~BB" means a range that includes the numerical value AA, which is listed before "AA~BB", as the lower limit, and the numerical value BB, which is listed after "AA~BB", as the upper limit.
[0112] [First Embodiment] <Organic electroluminescent element> The organic electroluminescent element according to the first embodiment includes an anode, a cathode, and two or more light-emitting units disposed between the anode and the cathode, The two or more light-emitting units include at least a first light-emitting unit having a first light-emitting band and a second light-emitting unit having a second light-emitting band. The anode, the first light-emitting unit, the second light-emitting unit, and the cathode are arranged in this order from the anode side toward the cathode side. The first light-emitting band includes a first light-emitting layer containing a first host material and a second light-emitting layer containing a second host material. The first light-emitting layer is positioned closer to the anode than the second light-emitting layer. The second emission band includes a third emission layer containing a third host material and a fourth emission layer containing a fourth host material. The third light-emitting layer is positioned closer to the anode than the fourth light-emitting layer. The first light-emitting layer, the second light-emitting layer, the third light-emitting layer, and the fourth light-emitting layer each independently contain a light-emitting compound that exhibits light emission with a maximum peak wavelength of 500 nm or less. The first host material and the third host material are different from each other. Unlike the second and fourth host materials, the first host material is The third host material differs from the second host material and the fourth host material, The second host material and the fourth host material are either identical or different from each other. The triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material satisfy the following equation (Equation 1), The triplet energy T1(H3) of the third host material and the triplet energy T1(H4) of the fourth host material satisfy the following equation (Equation 2). T1(H1)>T1(H2) …(Math 1) T1(H3)>T1(H4) …(Math 2)
[0113] In this specification, an organic electroluminescent element having two or more light-emitting units arranged between an anode and a cathode may be referred to as a tandem organic electroluminescent element (tandem organic EL element). Also in this specification, a light-emitting unit including multiple stacked light-emitting layers may be referred to as a stacked light-emitting unit.
[0114] The organic EL element according to this embodiment can achieve improved luminous efficiency by satisfying equations (Equation 1) and (Equation 2). Conventionally, Triplet-Triplet-Annihilation (sometimes referred to as TTA) is known as a technique for improving the luminous efficiency of organic EL devices. TTA is a mechanism in which triplet excitons collide with other triplet excitons to generate singlet excitons. The TTA mechanism is sometimes also referred to as the TTF mechanism.
[0115] 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 previously known, their spin states 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, while 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%. Meanwhile, the behavior of triplet excitons generated within organic matter has been theoretically investigated. According to SMBachilo et al. (J.Phys.Chem.A,104,7711(2000)), assuming that higher-order excitons such as quintets quickly revert to triplets, 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 be converted 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%.
[0116] According to the organic EL element of this embodiment, triplet excitons generated by the recombination of holes and electrons in the first light-emitting layer of the first light-emitting unit 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. In the organic EL element according to this embodiment, the first light-emitting unit includes 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 T1(H1) of the first host material in the first light-emitting layer and the triplet energy T1(H2) of the second host material in the second light-emitting layer satisfy the relationship of the formula (Equation 1). By providing a first light-emitting unit that includes a first light-emitting layer and a second light-emitting layer satisfying the relationship in the above formula (Equation 1), triplet excitons generated in the first light-emitting layer can 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 activated in the second light-emitting layer, singlet excitons are efficiently generated, and the luminescence efficiency is improved. Thus, the light-emitting unit in an organic electroluminescent device comprises a first light-emitting layer that mainly generates triplet excitons and a second light-emitting layer that mainly exhibits the TTF mechanism by utilizing triplet excitons that have moved from the first light-emitting layer, as separate regions. By using a compound with a lower 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 light-emitting efficiency.
[0117] The organic EL element according to this embodiment also has a second light-emitting unit. The second light-emitting unit includes a third light-emitting layer and a fourth light-emitting layer that satisfy the relationship in formula (Equation 2). The explanation above regarding the relationship between the first light-emitting layer and the second light-emitting layer in the first light-emitting unit, the manifestation of the TTF mechanism, and the improvement of luminous efficiency also applies to the third light-emitting layer and the fourth light-emitting layer in the second light-emitting unit. The luminous efficiency is improved when the third host material and the fourth host material satisfy formula (Equation 2).
[0118] In this embodiment, it is preferable that the triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material satisfy the relationship shown in the following formula (Equation 1A). T1(H1)-T1(H2)>0.03eV …(Math 1A)
[0119] In this embodiment, it is preferable that the triplet energy T1(H3) of the third host material and the triplet energy T1(H4) of the fourth host material satisfy the relationship shown in the following formula (Equation 2A). T1(H3)-T1(H4)>0.03eV …(Math 1A)
[0120] According to this embodiment, it is possible to provide an organic EL element with improved element performance. In the organic EL element according to this embodiment, the charge balance is optimized and the performance of the organic EL element is improved by using different compounds for the first host material in the first light-emitting layer of the first light-emitting unit and the third host material in the third light-emitting layer of the second light-emitting unit. According to one embodiment of the organic EL element present in this model, the luminous efficiency and lifespan of the organic EL element are improved.
[0121] <Light-emitting unit> The organic EL element according to this embodiment is an element that includes two or more light-emitting units between the anode and the cathode. The two or more light-emitting units include at least a first light-emitting unit and a second light-emitting unit. For example, three or more light-emitting units may be included between the anode and the cathode. That is, in the organic EL element according to this embodiment, the two or more light-emitting units may be three or more light-emitting units, in which case the three or more light-emitting units include at least a first light-emitting unit, a second light-emitting unit and a third light-emitting unit.
[0122] In the organic EL element according to this embodiment, it is preferable that a first light-emitting unit is arranged between the anode and the cathode, and a second light-emitting unit is arranged between the first light-emitting unit and the cathode. In this embodiment, it is preferable that, of the two or more light-emitting units, the first light-emitting unit is the light-emitting unit closest to the anode.
[0123] As a way of counting multiple light-emitting units arranged between the anode and the cathode, for example, if N light-emitting units are arranged between the anode and the cathode, they may be numbered sequentially from the light-emitting unit closest to the anode as the 1st stage, 2nd stage, 3rd stage, ..., (N-1)th stage, Nth stage, and so on. The organic EL element according to this embodiment, which includes two or more light-emitting units, includes at least a 1st stage light-emitting unit and a 2nd stage light-emitting unit. In one aspect of this embodiment, it is preferable that the first light-emitting unit is the 1st stage light-emitting unit closest to the anode, and the second light-emitting unit is the 2nd stage light-emitting unit.
[0124] Each light-emitting unit in an organic EL element typically contains one or more layers independently, with at least one of the layers in each light-emitting unit being a light-emitting layer. Each light-emitting unit in an organic EL element may also independently contain one or more layers other than the light-emitting layer, which are selected from the group consisting of organic compounds and inorganic materials. Inorganic materials are at least one of inorganic compounds and elemental materials. Preferably, each light-emitting unit independently contains one or more layers selected from the group consisting of layers composed solely of organic compounds, layers composed solely of inorganic materials, and layers composed of both organic compounds and inorganic materials. Examples of layers other than the light-emitting layer that may be included in each light-emitting unit include layers that can be used in organic EL elements. There are no particular limitations on layers other than the light-emitting layer that can be used in organic EL elements, but preferably, each light-emitting unit independently contains at least one layer selected from the group consisting of, for example, hole injection layers, hole transport layers, electron barrier layers, hole barrier layers, electron transport layers, and electron injection layers.
[0125] <Emission Band> (First, second, third, and fourth light-emitting layers) In the organic EL element according to this embodiment, the first light-emitting unit has a first light-emitting band, and the second light-emitting unit has a second light-emitting band. In this embodiment, the first light-emitting band and the second light-emitting band each independently include two or more light-emitting layers.
[0126] The first light-emitting band includes a first light-emitting layer containing a first host material and a second light-emitting layer containing a second host material. The first light-emitting layer is positioned closer to the anode than the second light-emitting layer. The first light-emitting layer is positioned between the anode and the second light-emitting layer. Preferably, the first light-emitting layer is the layer closest to the anode among the multiple layers of the first light-emitting band, and the second light-emitting layer is the layer closest to the cathode among the multiple layers of the first light-emitting band.
[0127] The second light-emitting band includes a third light-emitting layer containing a third host material and a fourth light-emitting layer containing a fourth host material. The third light-emitting layer is positioned closer to the anode than the fourth light-emitting layer. The fourth light-emitting layer is positioned between the third light-emitting layer and the cathode. Preferably, the third light-emitting layer is the layer closest to the anode among the multiple layers of the second light-emitting band, and the fourth light-emitting layer is the layer closest to the cathode among the multiple layers of the second light-emitting band.
[0128] In this specification, "first light-emitting layer, second light-emitting layer, third light-emitting layer, and fourth light-emitting layer" may be referred to as "first, second, third, and fourth light-emitting layers."
[0129] In this embodiment, it is preferable that at least one light-emitting layer selected from the group consisting of the first, second, third, and fourth light-emitting layers does not contain a metal complex. It is preferable that the first, second, third, and fourth light-emitting layers do not contain a metal complex.
[0130] In this embodiment, it is preferable that at least one light-emitting layer selected from the group consisting of the first, second, third, and fourth light-emitting layers does not contain a boron-containing complex. It is preferable that the first, second, third, and fourth light-emitting layers all do not contain a boron-containing complex.
[0131] In this embodiment, it is preferable that at least one light-emitting layer selected from the group consisting of the first, second, third, and fourth light-emitting layers does not contain a phosphorescent material. It is preferable that the first, second, third, and fourth light-emitting layers do not contain a phosphorescent material.
[0132] In this embodiment, it is also preferable that at least one light-emitting layer selected from the group consisting of the first, second, third, and fourth light-emitting layers does not contain heavy metal complexes and phosphorescent rare-earth metal complexes. It is preferable that none of the first, second, third, and fourth light-emitting layers contain heavy metal complexes and phosphorescent rare-earth metal complexes.
[0133] In this embodiment, it is also preferable that at least one light-emitting layer selected from the group consisting of the first, second, third, and fourth light-emitting layers does not contain heavy metal complexes such as iridium complexes, osmium complexes, and platinum complexes. It is preferable that none of the first, second, third, and fourth light-emitting layers contain heavy metal complexes such as iridium complexes, osmium complexes, and platinum complexes.
[0134] (Host material) Each light-emitting layer within the light-emitting band independently contains a host material. In this specification, "host material" refers to a material that makes up, for example, "50% by mass or more of the layer." For example, the host material content of each light-emitting layer within the light-emitting band is preferably 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more, independently. Alternatively, for example, the host material content of each light-emitting layer within the light-emitting band is preferably 99.5% by mass or less, or 99% by mass or less, independently.
[0135] In this embodiment, the first, second, third, and fourth light-emitting layers each contain a first host material, a second host material, a third host material, and a fourth host material as host materials, respectively. In this specification, "first host material, second host material, third host material, and fourth host material" may be written as "first, second, third, and fourth host materials."
[0136] In this embodiment, the host material contained in each light-emitting layer (preferably the first, second, third, and fourth host materials) is preferably one of the compounds selected from the group consisting of the compound represented by formula (2), the compound represented by formula (H11), the compound represented by formula (H12), the compound represented by formula (H13), the compound represented by formula (H14), the compound represented by formula (H15), and the compound represented by formula (H16).
[0137] (First host material and third host material) In this embodiment, the first host material and the third host material are different from each other. In this embodiment, the first host material is different from the second host material and the fourth host material. In this embodiment, the third host material is different from the second host material and the fourth host material.
[0138] In this embodiment, it is preferable that at least one of the first host material and the third host material is a compound selected from the group consisting of the compound represented by formula (H11), the compound represented by formula (H12), the compound represented by formula (H13), the compound represented by formula (H14), the compound represented by formula (H15), and the compound represented by formula (H16).
[0139] In this embodiment, the first host material is preferably a compound selected from the group consisting of a compound represented by the following formula (H11), a compound represented by the following formula (H12), a compound represented by the following formula (H13), a compound represented by the following formula (H14), a compound represented by the following formula (H15), and a compound represented by the following formula (H16).
[0140] In this embodiment, the third host material is preferably a compound selected from the group consisting of the compound represented by formula (H11), the compound represented by formula (H12), the compound represented by formula (H13), the compound represented by formula (H14), the compound represented by formula (H15), and the compound represented by formula (H16).
[0141] In this embodiment, the first host material and the third host material are preferably each independently selected from the group consisting of the compound represented by formula (H11), the compound represented by formula (H12), the compound represented by formula (H13), the compound represented by formula (H14), the compound represented by formula (H15), and the compound represented by formula (H16).
[0142] [ka]
[0143] (In the above formula (H11), R 101 ~R 110 , and R 111 ~R 120 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. However, R 101 ~R 110 One of them is L 101 This indicates the bonding position with R 111 ~R 120 One of them is L 101 It shows the bonding position with, L 101 teeth, single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 24 carbon atoms, or A divalent heterocyclic group having 5 to 24 substituted or unsubstituted ring-forming atoms, mx is 0, 1, 2, 3, 4, or 5. L 101 If there are 2 or more, then 2 or more L 101 They are either identical or different to one another.
[0144] R in the above formula (H11) 101 ~R 110 , and R 111 ~R 120 Any pair consisting of two or more adjacent elements cannot be combined with each other.
[0145] [ka]
[0146] (In the above formula (H12), Xa consists of an oxygen atom, a sulfur atom, and C(R 1201 )(R 1202 ), or Si(R 1203 )(R 1204 ) and R 1201 ~R 1204 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 121 ~R 130 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 121 ~R 130 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Nitro group, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or The group is represented by the above formula (H121), However, R 121 ~R 130 At least one of them is a group represented by the formula (H121), If there are multiple groups represented by the formula (H121), the multiple groups represented by the formula (H121) may be identical or different from each other. L 12 teeth, single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, ma is 0, 1, 2, or 3. L 12 If there are 2 or more, then 2 or more L 12 They are either identical or different from one another. Ar 12 This 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. Ar 12 If there are 2 or more Ar 12 They are either identical or different from one another. In the above formula (H121), * indicates the bond position.
[0147] [ka]
[0148] (In the above formula (H13), R 131 ~R 134 and R 139 ~R 140 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a substituted or unsubstituted monoring, or They do not bind to each other, R 135 ~R 138 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a substituted or unsubstituted monoring, or They do not bind to each other, Ar 131 Ar 132 , and R that does not form a monoring with or without substitution 131 ~R 140 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Cyano group, Nitro group, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or The group is represented by the above formula (H131), However, R 131 ~R 140 Ar 131 and Ar 132 At least one of them is a group represented by the formula (H131), If there are multiple groups represented by the above formula (H131), the multiple groups represented by the above formula (H131) may be identical or different from each other. L13 teeth, single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, Ar 13 teeth, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. mb is 0, 1, 2, 3, 4, or 5. L 13 If there are 2 or more, then 2 or more L 13 They are either identical or different from one another. Ar 13 If there are 2 or more Ar 13 They are either identical or different from one another. The asterisk (*) in formula (H131) indicates the bonding position with the benz[a]anthracene ring in formula (H13).
[0149] [ka]
[0150] (In the above formula (H14), R 1A and R 1B Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 15 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 17 carbon atoms, or These are heterocyclic groups with 5 to 17 substituted or unsubstituted ring-forming atoms. However, R 1A and R 1B At least one of them is a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, R 141 ~R 144 A set of two or more adjacent items from among them, and R 145 ~R 148 Any one of the pairs of two or more adjacent items is They combine with each other to form a substituted or unsubstituted monoring, or They bond to each other, forming substituted or unsubstituted fused rings. The group represented by the above formula (H141) is, If a substituted or unsubstituted monoring or a substituted or unsubstituted fused ring is formed on ring A, R 142 The carbon atom of ring A that is bonded to the carbon atom of ring B, or the carbon atom of the monoring on ring A and the fused ring on ring A that is bonded to the carbon atom of ring A that is furthest from the carbon atom C1 of ring A that is bonded by a single bond to carbon atom C2 on ring B, When a substituted or unsubstituted monoring or a substituted or unsubstituted fused ring is not formed on ring A but is formed on ring B, R 142 Bonded to a carbon atom, R is not a group represented by the above formula (H141). 142 R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring. 141 , R 143 , R 144 and R 145 ~R 148 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 17 carbon atoms, or These are heterocyclic groups with 5 to 17 substituted or unsubstituted ring-forming atoms. In the above formula (H141), Ar 14 This is a substituted or unsubstituted aryl group formed by the fusion of four or more rings, or a substituted or unsubstituted heterocyclic group formed by the fusion of four or more rings. L 14 teeth, single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 17 carbon atoms, or A divalent heterocyclic group having 5 to 17 substituted or unsubstituted ring-forming atoms, mc is 0, 1, or 2. * indicates the bonding position with the atoms constituting the ring in formula (H14) above. However, the compound represented by formula (H14) does not contain three or more substituted or unsubstituted aryl groups formed by the condensation of four or more rings, or substituted or unsubstituted heterocyclic groups formed by the condensation of four or more rings, in its molecule.
[0151] [ka]
[0152] (In the above formula (H15), R 150 ~R 159 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Cyano group, Nitro group, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or The group is represented by the above formula (H150), However, R 150 ~R 159 At least one of them is a group represented by the formula (H150), If there are multiple groups represented by the formula (H150), the multiple groups represented by the formula (H150) may be identical or different from each other. L 151 teeth, single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, Ar 151 teeth, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. mg is 0, 1, 2, 3, 4, or 5. L 151If there are 2 or more, then 2 or more L 151 They are either identical or different from one another. Ar 151 If there are 2 or more Ar 151 They are either identical or different from one another. The asterisk (*) in formula (H150) indicates the bonding position with the pyrene ring in formula (H15).
[0153] R in the above formula (H15) 150 ~R 159 Any pair consisting of two or more adjacent elements cannot be combined with each other.
[0154] [ka]
[0155] (In the above formula (H16), R 160 ~R 169 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 160 ~R 169 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R904 A base represented by ) -S-(R 905 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Cyano group, Nitro group, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or The group is represented by the above formula (H161), However, the substituents in the case where the substituted or unsubstituted monoring has substituents, the substituents in the case where the substituted or unsubstituted fused ring has substituents, and R 160 ~R 169 At least one of these is a group represented by formula (H161), If there are multiple groups represented by the above formula (H161), the multiple groups represented by the above formula (H161) may be identical or different from each other. L 16 teeth, single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, Ar 16 teeth, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. mf is 0, 1, 2, 3, 4, or 5. L 16 If there are 2 or more, then 2 or more L 16 They are either identical or different from one another. Ar 16 If there are 2 or more Ar 16 They are either identical or different from one another. The asterisk (*) in formula (H161) indicates the bonding position with the ring represented by formula (H16).
[0156] (A compound represented by any of the above formulas (H11) to (H16) (for example, in the first host material and the third host material), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. R 801 If multiple R801 They are either identical or different from one another. R 802 If multiple R 802 They are either identical or different to one another.
[0157] In one embodiment of this design, Ar in formulas (H11), (H12), (H13), (H14), (H15), and (H16) 12 Ar 13 Ar 14 Ar 151 , and Ar 16 These are, independently, condensed polycyclic aromatic hydrocarbon groups.
[0158] In one embodiment of this design, Ar in formulas (H11), (H12), (H13), (H14), (H15), and (H16) 12 Ar 13 Ar 14 Ar 151 , and Ar 16 These are, independently, fused polycyclic heterocyclic groups.
[0159] In this embodiment, R in formula (H11) 101 , R 103 , R 106 or R 108 is L 101 This indicates the bonding position with R 112 , R 115 , R 117 or R 120 is L 101 It is preferable to indicate the bonding position with R in formula (H11). 101 and R 112 is L 101 When indicating the bonding position with, the compound represented by formula (H11) is the compound represented by the following formula (H111). In this embodiment, it is also preferable that at least one of the first host material and the third host material is the compound represented by the following formula (H111).
[0160] [ka]
[0161] (In the above formula (H111), R 102 ~R 111 , R 113 ~R 120 , L 101 and mx are, respectively, R in formula (H11) above. 102 ~R 111 , R 113 ~R 120 , L 101 (And it is synonymous with MX.)
[0162] In this embodiment, Xa in formula (H12) is preferably an oxygen atom. In this embodiment, R in formula (H12) 124 or R 129 is L 12 It is preferable to show the bonding position with. In the above formula (H12), Xa is an oxygen atom, and R 124 is L 12 When indicating the bonding position with, the compound represented by formula (H12) can be represented, for example, by the following formula (H122). In formula (H12), Xa is an oxygen atom, and R 129 is L 12 When indicating the bonding position with, the compound represented by formula (H12) can be represented, for example, by the following formula (H123).
[0163] In this embodiment, the compound represented by formula (H12) may also preferably be the compound represented by formula (H122) or the compound represented by formula (H123).
[0164] [ka]
[0165] (In the above formulas (H122) and (H123), R 121 ~R 130 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. Ar 12 , L 12 and ma are, respectively, Ar in formula (H121) 12 , L 12 (And is synonymous with ma.)
[0166] In one embodiment of this model, Ar in formulas (H122) and (H123) 12 This is a condensed polycyclic aromatic hydrocarbon group.
[0167] In one embodiment of this model, Ar in formulas (H122) and (H123) 12 It is a fused polycyclic heterocyclic group.
[0168] In this embodiment, Ar in formula (H13) 131 Or Ar 132is L 13 It is preferable to indicate the bonding position with the Ar in formula (H13). 131 is L 13 When indicating the bonding position with, the compound represented by formula (H13) can be represented, for example, by the following formula (H132). The Ar in formula (H13) 132 is L 13 When indicating the bonding position with, the compound represented by formula (H13) can be represented, for example, by the following formula (H133).
[0169] In this embodiment, the compound represented by formula (H13) may also preferably be the compound represented by formula (H132) or the compound represented by formula (H133).
[0170] [ka]
[0171] (In the above formulas (H132) and (H133), R 131 ~R 140 Ar 131 and Ar 132 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801A base represented by -COOR 802 A base represented by halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. L 13 Ar 13 and mb are, respectively, L in formula (H131) 13 Ar 13 (And is synonymous with mb.)
[0172] In one embodiment of this model, Ar in formulas (H132) and (H133) 131 and Ar 132 This is a condensed polycyclic aromatic hydrocarbon group.
[0173] In one embodiment of this model, Ar in formulas (H132) and (H133) 131 and Ar 132 It is a fused polycyclic heterocyclic group.
[0174] In one embodiment of this present invention, R in formula (H14) 145 ~R 148 Any one of two or more adjacent pairs of these pairs may bond to each other to form a substituted or unsubstituted monoring, or bond to each other to form a substituted or unsubstituted fused ring, and the group represented by formula (H141) is R 142 It is preferable that the bond is to a carbon atom that is bonded to the carbon atom.
[0175] In one embodiment of this design, the compound represented by formula (H14) is a compound represented by the following formulas (H142), (H143), or (H144).
[0176] [ka]
[0177] [ka]
[0178] (In formulas (H142), (H143), or (H144) above, R 1A , R 1B , R 141 , R 143 , R 144 , R 145 , R 146 , R 147 and R 148 These are, respectively, R in the above formula (H14). 1A , R 1B , R 141 , R 143 , R 144 , R 145 , R 146 , R 147 and R 148 It is synonymous with, Ar 14 , L 14 and mc are, respectively, Ar in formula (H141) 14 , L 14 And is synonymous with mc, R 1401 ~R 1404 Of the pairs of adjacent elements, one or more pairs are not connected to each other. R 1401 ~R 1404 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 17 carbon atoms, or It is a heterocyclic group with 5 to 17 ring-forming atoms, either substituted or unsubstituted.
[0179] In this embodiment, Ar in formula (H14), formula (H143), or formula (H144) 14 However, it is also preferable that the group be derived from a substituted or unsubstituted pyrene ring, a substituted or unsubstituted fluorantene ring, a substituted or unsubstituted benzofluorantene ring, a substituted or unsubstituted benzoanthracene ring, or a substituted or unsubstituted benzoxanthene ring.
[0180] In this embodiment, it is also preferable that at least one of the first host material and the third host material is a compound selected from the group consisting of the compound represented by formula (H111), the compound represented by formula (H122), the compound represented by formula (H123), the compound represented by formula (H132), the compound represented by formula (H133), the compound represented by formula (H142), the compound represented by formula (H143), and the compound represented by formula (H144).
[0181] In one embodiment of this design, at least one of the first host material and the third host material is a compound having at least one group represented by the following formula (HX1) in its molecule.
[0182] [ka]
[0183] (In the above formula (HX1), R X1 ~R X8 and R X11 ~R X14 Each of them operates independently. hydrogen atom, halogen atom, Cyano group, Nitro group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 ~R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If multiple R 901 They are either identical or different from one another. R 902If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. nx is 0, 1, or 2. however, When nx is 0, R X1 ~R X8 One of the options is a single bond that joins *ex, When nx is 1, one condition is satisfied which can be selected from the group consisting of (a1) to (a6) below, When nx is 2, it satisfies two conditions selected from the group consisting of (a1) to (a6) below, where (a1) and (a2) cannot be satisfied simultaneously, (a2) and (a3) cannot be satisfied simultaneously, (a4) and (a5) cannot be satisfied simultaneously, and (a5) and (a6) cannot be satisfied simultaneously. R X11 ~R X14 , as well as R which is not a single bond attached to *cx and *dx X1 ~R X8 One of the options is a single bond that joins *ex, Z1 is an oxygen atom or a sulfur atom. *fx indicates the bonding position with an atom in the first or third host material. (a1)R X1 and R X2 One of them is a single bond that connects to *cx, and R X1 and R X2The other side is a single bond that connects to *dx. (a2)R X2 and R X3 One of them is a single bond that connects to *cx, and R X2 and R X3 The other side is a single bond that connects to *dx. (a3)R X3 and R X4 One of them is a single bond that connects to *cx, and R X3 and R X4 The other side is a single bond that connects to *dx. (a4)R X5 and R X6 One of them is a single bond that connects to *cx, and R X5 and R X6 The other side is a single bond that connects to *dx. (a5)R X6 and R X7 One of them is a single bond that connects to *cx, and R X6 and R X7 The other side is a single bond that connects to *dx. (a6)R X7 and R X8 One of them is a single bond that connects to *cx, and R X7 and R X8 The other bond is a single bond connecting to *dx.
[0184] In one embodiment of this design, when nx in formula (HX1) is 0, the base represented by formula (HX1) is represented by the following formula (HX10).
[0185] In one embodiment of this design, at least one of the first host material and the third host material is a compound having at least one group represented by the following formula (HX10) in its molecule.
[0186] [ka]
[0187] (In the above formula (HX10), R X1 ~R X8, and Z1 are, respectively, R in formula (HX1) X1 ~R X8 , and is synonymous with Z1, However, R X1 ~R X8 One of the options is a single bond that joins *ex, *fx indicates the bonding position with an atom in the first or third host material.
[0188] In one embodiment of this invention, at least one of the first host material and the third host material is a compound having at least one group represented by the formula (HX1) in its molecule and nx = 1.
[0189] In one embodiment of this invention, at least one of the first host material and the third host material is a compound having at least one group selected from the group consisting of a group represented by the following formula (HX11), a group represented by the formula (HX12), and a group represented by the formula (HX13) in its molecule. The group represented by the following formula (HX11) corresponds to a group that satisfies condition (a3), the group represented by formula (HX12) corresponds to a group that satisfies condition (a2), and the group represented by formula (HX13) corresponds to a group that satisfies condition (a1).
[0190] [ka]
[0191] [ka]
[0192] [ka]
[0193] (In the above formulas (HX11), (HX12), and (HX13), R X1 ~R X8 , R X11 ~R X14, and Z1 are, respectively, R in formula (HX1) X1 ~R X8 , R X11 ~R X14 , and is synonymous with Z1, However, R in the above formulas (HX11), (HX12), and (HX13) X1 ~R X8 and R X11 ~R X14 Of these, one is a single bond that connects to *ex, *fx indicates the bonding position with an atom in the first or third host material.
[0194] In one embodiment of this present invention, Ar in the compound represented by formula (H13) 131 Ar 132 , and Ar 13 At least one selected from the group consisting of is one of the groups consisting of the group represented by formula (HX11), the group represented by (HX12), and the group represented by (HX13).
[0195] In one embodiment of this present invention, Ar in the compound represented by formula (H132) 132 , and Ar 13 At least one selected from the group consisting of is one of the groups consisting of the group represented by formula (HX11), the group represented by formula (HX12), and the group represented by formula (HX13).
[0196] In one embodiment of this present invention, Ar in the compound represented by formula (H133) 131 , and Ar 13 At least one selected from the group consisting of is one of the groups consisting of the group represented by formula (HX11), the group represented by formula (HX12), and the group represented by formula (HX13).
[0197] In this embodiment, the compound represented by formula (H13) is also preferably a compound represented by the following formula (H134) or formula (H135).
[0198] [ka]
[0199] [ka]
[0200] (In the above formulas (H134) and (H135), R 131 ~R 140 , and Ar 132 These are, respectively, R in the above formula (H13). 131 ~R 140 , and Ar 132 It is synonymous with, L 13 , and mb are, respectively, L in formula (H131) 13 , and are synonymous with mb, R X1 , R X2 , R X4 , R X5 ~R X7 , R X11 ~R X14 , and Z1 are, respectively, R in formula (HX1) X1 , R X2 , R X4 , R X5 ~R X7 , R X11 ~R X14 (This is synonymous with Z1.)
[0201] In one embodiment of this present invention, the condensed polycyclic heterocyclic group in the first host material and the third host material is a group selected from the group consisting of the group represented by formula (HX1), the group represented by formula (HX10), the group represented by formula (HX11), the group represented by formula (HX12), the group represented by formula (HX13), and the group represented by formula (HX2).
[0202] In one embodiment of this invention, the hole implantability of the host material is improved (more specifically, with respect to the aryl groups in the host material molecule) by having at least one group selected from the group consisting of the group represented by formula (HX1), the group represented by formula (HX10), the group represented by formula (HX11), the group represented by formula (HX12), and the group represented by formula (HX13) in the host material molecule. Hole implantability is more easily improved when the host material has a benz[a]anthracene structure, such as the compound represented by formula (H13).
[0203] In one embodiment of this design, at least one of the first host material and the third host material is a compound having at least one group represented by the following formula (HX2) in its molecule.
[0204] [ka]
[0205] (In the above formula (HX2), R 171 ~R 180 One of the selected is a single bond that joins *gx, R 171 ~R 180 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. *hx indicates the bonding position with an atom in the first or third host material. R 901 ~R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different to one another.
[0206] R in the above formula (HX2) 171 ~R 180 Any pair consisting of two or more adjacent elements cannot be combined with each other.
[0207] In this embodiment, Ar in formulas (H12), (H122), and (H123) 12 However, it is preferable that the group is represented by the above formula (HX2).
[0208] In this embodiment, R in formula (HX2) 174 or R 179 However, it is preferable that the bond is a single bond connected to *gx.
[0209] In this embodiment, the compound represented by formula (H12) is also preferably the compound represented by the following formula (H124).
[0210] [ka]
[0211] (In the above formula (H124), R 121 ~R 123 , R 125 ~R 130 , L 12 and ma are, respectively, R in formula (H12) 121 ~R 123 , R 125 ~R 130 , L 12 And is synonymous with ma, R 171 ~R 173 , and R 175 ~R 180 These are, respectively, R in the above formula (HX2). 171 ~R 173 , and R 175 ~R 180 (This is synonymous with...)
[0212] In one embodiment of this design, the group represented by formula (H150) is the group represented by the following formula (H151).
[0213] [ka]
[0214] (In the above formula (H151), X 15 C(R 1511 )(R 1512 ), oxygen atom, or sulfur atom, L 15 teeth, single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, md is 0, 1, 2, 3, 4, or 5. L 15 If there are 2 or more, then 2 or more L 15 They are either identical or different from one another. R 1500 ~R 1504 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R 1511 and R 1512 A group consisting of, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 1500 ~R 1504 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. Multiple R 1500 They are either identical or different from one another. R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 1511 and R 1512 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. The asterisk (*) in formula (H151) indicates the bonding position with the pyrene ring in formula (H15).
[0215] In this embodiment, it is also preferable that the compound represented by formula (H15) is a monopyrene compound containing only one pyrene ring in its molecule.
[0216] In this embodiment, R in formula (H15) 151 , R 153 , R 156 or R 158 However, it is preferable that the group is represented by the above formula (H150).
[0217] In this embodiment, R in formula (H15) 151 , R 153 , R 156 or R 158 However, it is preferable that the group is represented by the above formula (H151).
[0218] In the organic EL element according to this embodiment, it is also preferable that one of the first host material and the third host material is a compound represented by formula (H11), and the other of the first host material and the third host material is a compound represented by formula (H13). It is more preferable that the first host material is a compound represented by formula (H11) and the third host material is a compound represented by formula (H13). It is even more preferable that the first host material is a compound represented by formula (H111) and the third host material is a compound represented by formula (H132) or formula (H133). It is even more preferable that the first host material is a compound represented by formula (H111) and the third host material is a compound represented by formula (H134) or formula (H135). The element performance is easily improved when the first host material and the third host material are included in the first and second light-emitting units in such combinations of compounds.
[0219] In the organic EL element according to this embodiment, it is also preferable that one of the first host material and the third host material is a compound represented by formula (H14) or formula (H15), and the other of the first host material and the third host material is a compound represented by formula (H13). It is more preferable that the first host material is a compound represented by formula (H14) or formula (H15), and the third host material is a compound represented by formula (H13). It is even more preferable that the first host material is a compound represented by formula (H142), formula (H143), or formula (H144), and the third host material is a compound represented by formula (H132) or formula (H133). It is even more preferable that the first host material is a compound represented by formula (H142), formula (H143), or formula (H144), and the third host material is a compound represented by formula (H134) or formula (H135). The inclusion of the first host material and the third host material in such a compound combination in the first and second light-emitting units makes it easier to improve the performance of the device.
[0220] In the organic EL element according to this embodiment, it is also preferable that one of the first host material and the third host material is a compound represented by formula (H12), and the other of the first host material and the third host material is a compound represented by formula (H13). It is more preferable that the first host material is a compound represented by formula (H12) and the third host material is a compound represented by formula (H13). It is even more preferable that the first host material is a compound represented by formula (H122) or formula (H123) and the third host material is a compound represented by formula (H132) or formula (H133). It is even more preferable that the first host material is a compound represented by formula (H124) and the third host material is a compound represented by formula (H134) or formula (H135). The element performance is easily improved when the first host material and the third host material are included in the first and second light-emitting units in such combinations of compounds.
[0221] In the organic EL element according to this embodiment, it is preferable that one or both of the first host material and the third host material are compounds containing one or more deuterium atoms in their molecules.
[0222] In the organic EL element according to this embodiment, it is also preferable that one or both of the first host material and the third host material are compounds that do not contain deuterium atoms in their molecules.
[0223] In this embodiment, it is also preferable that one or both of the first host material and the third host material contain only carbon atoms and hydrogen atoms in their molecules.
[0224] In this embodiment, it is also preferable that one or both of the first host material and the third host material contain carbon atoms, hydrogen atoms, and heteroatoms in their molecules. If one or both of the first host material and the third host material contain heteroatoms, it is preferable that the heteroatoms are one or more selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, silicon atoms, phosphorus atoms, and boron atoms.
[0225] In this embodiment, it is also preferable that the first host material is a compound containing only carbon atoms and hydrogen atoms in its molecule, and the third host material is a compound containing carbon atoms, hydrogen atoms, and heteroatoms in its molecule.
[0226] In this embodiment, it is also preferable that both the first host material and the third host material contain carbon atoms, hydrogen atoms, and heteroatoms in their molecules.
[0227] In this embodiment, L 101 , L 12 , L 13 , L 14 , L 15 , L 151 , and L 16 Each of these is preferably a single bond or a group represented by the following formulas (L1), (L2), (L3), (L4), (L5), (L6), (L7), (L8), (L9), or (L10).
[0228] [ka]
[0229] In the above formulas (L1) to (L10), * indicates a bond position. Each of the groups represented by the above formulas (L1) to (L10) may independently have one or more of the above-mentioned "any substituents" or not (i.e., may be unsubstituted). Each of the groups represented by the above formulas (L1) to (L10) may independently have one or more deuterium atoms.
[0230] In the first host material and the third host material, the substituents in the case of "substituted or unsubstituted" are preferably, independently, a halogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring-forming atoms.
[0231] In the first host material and the third host material, the substituents in the case of "substituted or unsubstituted" are preferably, independently, an unsubstituted C1-C6 alkyl group, an unsubstituted ring-forming C6-C13 aryl group, or an unsubstituted ring-forming C5-C13 heterocyclic group.
[0232] In the first host material and the third host material, the substituents in the case of "substituted or unsubstituted" are preferably, independently, an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 10 ring-forming atoms.
[0233] In one embodiment of the organic EL display device according to this embodiment, the groups described as "substituted or unsubstituted" in the first host material and the third host material are all "unsubstituted" groups.
[0234] (Method for manufacturing the first host material and the third host material) The first host material and the third host material can be manufactured by known methods. Alternatively, the first host material and the third host material can also be manufactured by following known methods and using known alternative reactions and raw materials tailored to the target product.
[0235] (Specific examples of the first and third host materials) Specific examples of the first and third host materials include, for example, the following compounds. However, the present invention is not limited to these specific examples of the first and third host materials.
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[0401] (Second host material and fourth host material) In one embodiment of the organic EL element according to this embodiment, the second host material and the fourth host material are identical to each other. Alternatively, in one embodiment of the organic EL element according to this embodiment, the second host material and the fourth host material are different to each other.
[0402] In this embodiment, the second host material and the fourth host material are not particularly limited. Preferably, at least one of the second host material and the fourth host material is an anthracene derivative.
[0403] In this embodiment, the second host material and the fourth host material are more preferably compounds represented by the following formula (2), independently of each other.
[0404] [ka]
[0405] (In the above formula (2), R 201 ~R 208 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. L 201 and L 202 Each of them operates independently. single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, Ar 201 and Ar 202 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0406] (In the compound represented by formula (2) above (for example, in the second host material and the fourth host material), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. R 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 They are either identical or different to one another.
[0407] R in equation (2) above 201 ~R 208 Any pair consisting of two or more adjacent elements cannot be combined with each other.
[0408] In this embodiment, the second host material and the fourth host material may both be compounds represented by formula (2), and may be different compounds from each other.
[0409] In this embodiment, Ar 202 The ring-forming arylene group having 6 to 50 carbon atoms, whether substituted or unsubstituted, preferably contains at least one deuterium atom. In this embodiment, L 202 The aryl group is preferably a substituted or unsubstituted ring-forming group having 6 to 50 carbon atoms, and preferably contains at least one deuterium atom. In this embodiment, -L 202 -Ar 202 The group represented by preferably contains at least one deuterium atom.
[0410] In this embodiment, the compound represented by formula (2) is preferably a compound represented by the following formulas (H21), (H22), (H23), (H24), (H25), (H26), (H27), (H28), or (H29).
[0411] [ka]
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[0416] (In the above formulas (H21) to (H29), 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 208 These are, respectively, R in the above formula (H2). 201 ~R 208 (This is synonymous with...)
[0417] In this embodiment, the second host material and the fourth host material are preferably compounds selected independently from the group consisting of the compounds represented by formula (H21), formula (H22), formula (H23), formula (H24), formula (H25), formula (H26), formula (H27), formula (H28), and formula (H29).
[0418] In one embodiment of the organic EL element according to this embodiment, at least one of the second host material and the fourth host material is a compound having at least one group represented by the following formula (HY1) in its molecule.
[0419] [ka]
[0420] (In the above formula (HY1), R Y1 ~R Y8 and R Y11 ~R Y14 Each of them operates independently. hydrogen atom, halogen atom, Cyano group, Nitro group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. ny is either 0 or 1. however, When ny is 0, R Y1 ~R Y8 One of the selected options is a single bond that joins *ey, When ny is 1, one condition is satisfied which is selected from the group consisting of (b1) to (b3) below, and R Y5 ~R Y8 , R Y11 ~R Y14 , as well as R which is not a single bond attached to *cy and *dy Y1 ~R Y4 One of the selected options is a single bond that joins *ey, Z2 is either an oxygen atom or a sulfur atom. *fy indicates the bonding position with atoms in the second host material. (b1)R Y1 and R Y2 One of them is a single bond that connects to *cy, R Y1 and R Y2 The other bond is a single bond that connects to *dy. (b2)R Y2 and R Y3 One of them is a single bond that connects to *cy, R Y2 and R Y3 The other bond is a single bond that connects to *dy. (b3)R Y3 and R Y4 One of them is a single bond that connects to *cy, R Y3 and R Y4 The other bond is a single bond that connects to *dy.
[0421] In one embodiment of the organic EL element according to this embodiment, when ny in formula (HY1) is 0, the group represented by formula (HY1) is represented by the following formula (HY10). In one embodiment of the organic EL element according to this embodiment, at least one of the second host material and the fourth host material is a compound having at least one group represented by the following formula (HY10) in its molecule.
[0422] [ka]
[0423] (In the above formula (HY10), R Y1 ~R Y8 , and Z2 are, respectively, R in formula (HY1). Y1 ~R Y8 , and is synonymous with Z2, However, R Y1 ~R Y8 One of the selected options is a single bond that joins *ey, *fy indicates the bonding position with the atom in the second host material.
[0424] In one embodiment of the organic EL element according to this embodiment, at least one of the second host material and the fourth host material is a compound having at least one group represented by the formula (HY1) in its molecule and ny is 1.
[0425] In one embodiment of the organic EL element according to this embodiment, at least one of the second host material and the fourth host material is a compound having at least one group selected from the group consisting of groups represented by the following formulas (HY11), (HY12), and (HY13) in its molecule. The group represented by formula (HY11) corresponds to a group that satisfies condition (b3), the group represented by formula (HY12) corresponds to a group that satisfies condition (b2), and the group represented by formula (HY13) corresponds to a group that satisfies condition (b1).
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[0429] (In the above formulas (HY11), (HY12), and (HY13), R Y1 ~R Y8 , R Y11 ~R Y14 , and Z2 are, respectively, R in formula (HY1). Y1 ~R Y8 , R Y11 ~R Y14 , and is synonymous with Z2, However, R Y1 ~R Y8 and R Y11 ~R Y14 Of these, one is a single bond that connects to *ey, *fy indicates the bonding position with an atom in the second or fourth host material.
[0430] In one embodiment of the organic EL element according to this embodiment, at least one of the second host material and the fourth host material is a compound represented by formula (2), and the molecule of the compound represented by formula (2) contains at least one group represented by formula (HY1).
[0431] In one embodiment of the organic EL element according to this embodiment, Ar in formula (2) 201 and Ar 202 At least one of them is a group represented by the formula (HY1).
[0432] In one embodiment of the organic EL element according to this embodiment, Ar 201 However, this is the group represented by the above formula (HY1).
[0433] In one embodiment of the organic EL element according to this embodiment, Ar in formula (2) 201 Or Ar 202However, this is the group represented by the above formula (HY1).
[0434] In one embodiment of the organic EL element according to this embodiment, at least one of the second host material and the fourth host material is a compound represented by formula (2), and the molecule of the compound represented by formula (2) has at least one group selected from the group consisting of groups represented by formulas (HY11), (HY12), and (HY13).
[0435] In one embodiment of the organic EL element according to this embodiment, Ar in formula (2) 201 and Ar 202 At least one of them is a group selected from the group consisting of the groups represented by formulas (HY11), (HY12), and (HY13).
[0436] In one embodiment of the organic EL element according to this embodiment, Ar in formula (2) 201 Or Ar 202 However, it is one of the groups selected from the group consisting of the groups represented by formulas (HY11), (HY12), and (HY13).
[0437] In one embodiment of the organic EL element according to this embodiment, Ar 201 However, it is a group represented by formula (HY11), formula (HY12), or formula (HY13).
[0438] In one embodiment of the organic EL device according to this embodiment, the excitation resistance of the host material is improved by having at least one group selected from the group consisting of groups represented by formulas (HY1), (HY10), (HY11), (HY12), and (HY13) in the molecule. By using such a host material in the second light-emitting layer, the lifespan of the organic EL device is easily extended.
[0439] In one embodiment of the organic EL element according to this embodiment, Ar in formula (2) 201 and Ar 202However, each of these is independently a substituted or unsubstituted ring-forming aryl group with 6 to 18 carbon atoms.
[0440] In one embodiment of the organic EL element according to this embodiment, Ar 201 However, these are substituted or unsubstituted ring-forming aryl groups with 6 to 18 carbon atoms.
[0441] In one embodiment of the organic EL element according to this embodiment, R in formula (2) 201 ~R 208 At least one of them is a deuterium atom. In one embodiment of the organic EL element according to this embodiment, R in formula (2) 201 ~R 208 At least one of them is a deuterium atom. In one embodiment of the organic EL element according to this embodiment, R in formula (2) 201 ~R 208 However, they are all deuterium atoms. In one embodiment of the organic EL element according to this embodiment, R in formula (2) 201 ~R 208 However, they are all light hydrogen atoms.
[0442] In one embodiment of the organic EL element according to this embodiment, Ar in formula (2) 201 Ar 202 , L 201 and L 202 At least one of the hydrogen atoms it possesses is a deuterium atom. In one embodiment of the organic EL element according to this embodiment, Ar in formula (2) 201 Ar 202 , L 201 and L 202 All of the hydrogen atoms it possesses are deuterium atoms. In one embodiment of the organic EL element according to this embodiment, Ar in formula (2) 201 Ar 202 , L 201 and L 202 All of the hydrogen atoms it possesses are light hydrogen atoms.
[0443] In one embodiment of the organic EL element according to this embodiment, R in formulas (HY1), (HY10), (HY11), (HY12), and (HY13) Y1 ~R Y8 , R Y11 ~R Y14 At least one of them is a deuterium atom.
[0444] In this embodiment, it is also preferable that one or both of the second host material and the fourth host material are compounds containing one or more deuterium atoms in their molecules.
[0445] In this embodiment, it is also preferable that one or both of the second host material and the fourth host material are compounds that do not contain deuterium atoms in their molecules.
[0446] In this embodiment, it is also preferable that one or both of the second host material and the fourth host material contain only carbon atoms and hydrogen atoms in their molecules.
[0447] In this embodiment, it is also preferable that one or both of the second host material and the fourth host material contain carbon atoms, hydrogen atoms, and heteroatoms in their molecules. If one or both of the second host material and the fourth host material contain heteroatoms, it is preferable that the heteroatoms are one or more selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, silicon atoms, phosphorus atoms, and boron atoms.
[0448] In this embodiment, it is also preferable that one or both of the second light-emitting layer and the fourth light-emitting layer further contain a cohost material, and that the cohost material contained in the second light-emitting layer and the cohost material contained in the fourth light-emitting layer are identical or different from each other, the second host material is different from the cohost material contained in the second light-emitting layer and the cohost material contained in the fourth light-emitting layer, and the fourth host material is different from the cohost material contained in the second light-emitting layer and the cohost material contained in the fourth light-emitting layer.
[0449] In one embodiment of the organic EL element according to this embodiment, the cohost material is an anthracene derivative. In one embodiment of the organic EL element according to this embodiment, the cohost material is a compound represented by any of formulas (2) and (H21) to (H29).
[0450] In the second and fourth host materials, the substituents in the case of "substituted or unsubstituted" are preferably, independently, a halogen atom, an unsubstituted C1-C25 alkyl group, an unsubstituted ring-forming C6-C25 aryl group, or an unsubstituted ring-forming C5-C25 heterocyclic group.
[0451] In the second and fourth host materials, the substituents in the case of "substituted or unsubstituted" are preferably, independently, an unsubstituted C1-C6 alkyl group, an unsubstituted ring-forming C6-C13 aryl group, or an unsubstituted ring-forming C5-C13 heterocyclic group.
[0452] In the second and fourth host materials, the substituents in the case of "substituted or unsubstituted" are preferably, independently, an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 10 ring-forming atoms.
[0453] In one embodiment of the organic EL element according to this embodiment, the groups described as "substituted or unsubstituted" in the second host material and the fourth host material are all "unsubstituted" groups.
[0454] (Method for manufacturing the second host material and the fourth host material) The second and fourth host materials according to this embodiment can be manufactured by known methods, or by following such methods and using known alternative reactions and raw materials suited to the target material.
[0455] (Specific examples of the second and fourth host materials) Specific examples of the second and fourth host materials according to this embodiment include, for example, the following compounds. However, the present invention is not limited to these specific examples.
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[0498] (Luminescent compounds) Preferably, each light-emitting layer within the light-emitting band independently further contains a luminescent compound. Each luminescent compound contained in each light-emitting layer is independently either fluorescent or phosphorescent. In this embodiment, it is preferable that at least one of the light-emitting layers contains a fluorescent compound. In this embodiment, when a light-emitting layer contains a host material and a luminescent compound, the upper limit of the sum of the host material content and the luminescent compound content in the light-emitting layer is 100% by mass.
[0499] In this embodiment, the first, second, third, and fourth light-emitting layers each independently contain a host material and a light-emitting compound that exhibits light emission with a maximum peak wavelength of 500 nm or less.
[0500] In the organic EL element according to this embodiment, it is preferable that at least one of the luminescent compounds contained in the first light-emitting layer, second light-emitting layer, third light-emitting layer, and fourth light-emitting layer is a luminescent compound that exhibits light emission with a maximum peak wavelength of 430 nm or more and 480 nm or less.
[0501] In the organic EL element according to this embodiment, it is preferable that at least one of the luminescent compounds contained in the first light-emitting layer, second light-emitting layer, third light-emitting layer, and fourth light-emitting layer is a fluorescent compound.
[0502] In the organic EL element according to this embodiment, it is also preferable that the luminescent compounds contained in the first light-emitting layer, second light-emitting layer, third light-emitting layer, and fourth light-emitting layer are all fluorescent compounds.
[0503] In the organic EL element according to this embodiment, it is preferable that at least one of the light-emitting layers selected from the group consisting of a first light-emitting layer, a second light-emitting layer, a third light-emitting layer, and a fourth light-emitting layer does not contain a phosphorescent material. In the organic EL element according to this embodiment, it is preferable that the first light-emitting layer, the second light-emitting layer, the third light-emitting layer, and the fourth light-emitting layer do not contain phosphorescent material.
[0504] In this specification, the luminescent compound contained in the first luminescent layer may be referred to as the first luminescent compound, the luminescent compound contained in the second luminescent layer may be referred to as the second luminescent compound, the luminescent compound contained in the third luminescent layer may be referred to as the third luminescent compound, and the luminescent compound contained in the fourth luminescent layer may be referred to as the fourth luminescent compound.
[0505] In this specification, "first luminescent compound, second luminescent compound, third luminescent compound, and fourth luminescent compound" may be referred to as "first, second, third, and fourth luminescent compounds."
[0506] In this embodiment, it is preferable that the first, second, third, and fourth luminescent compounds each independently exhibit luminescence with a maximum peak wavelength of 480 nm or less, or luminescent compounds exhibiting luminescence with a maximum peak wavelength of 470 nm or less.
[0507] In this embodiment, it is preferable that the first, second, third, and fourth luminescent compounds each independently exhibit luminescence with a maximum peak wavelength of 430 nm or higher, or luminescent compounds exhibiting luminescence with a maximum peak wavelength of 440 nm or higher.
[0508] In this embodiment, it is preferable that at least one compound selected from the group consisting of the first, second, third, and fourth luminescent compounds is a fluorescent compound, and it is more preferable that all of the first, second, third, and fourth luminescent compounds are fluorescent compounds.
[0509] In this embodiment, it is preferable that at least one compound selected from the group consisting of the first, second, third, and fourth luminescent compounds is a compound that exhibits blue light emission, and it is more preferable that all of the first, second, third, and fourth luminescent compounds are compounds that exhibit blue light emission.
[0510] In this embodiment, it is preferable that at least one compound selected from the group consisting of the first, second, third, and fourth luminescent compounds is a compound that does not contain an azine ring structure in its molecule, and it is more preferable that all of the first, second, third, and fourth luminescent compounds are compounds that do not contain an azine ring structure in their molecules.
[0511] Preferably, at least one compound selected from the group consisting of the first, second, third, and fourth luminescent compounds is not a boron-containing complex, and more preferably, none of the first, second, third, and fourth luminescent compounds are boron-containing complexes.
[0512] Preferably, at least one compound selected from the group consisting of the first, second, third, and fourth luminescent compounds is not a complex, and more preferably, none of the first, second, third, and fourth luminescent compounds are complexes.
[0513] In this embodiment, the first, second, third, and fourth luminescent compounds are either identical or different from each other. In this embodiment, it is preferable that the first luminescent compound and the second luminescent compound are the same compound. In this embodiment, it is preferable that the third luminescent compound and the fourth luminescent compound are the same compound. In this embodiment, it is preferable that the first luminescent compound and the third luminescent compound are the same compound. In this embodiment, it is preferable that the second luminescent compound and the fourth luminescent compound are the same compound.
[0514] In this embodiment, it is also preferable that the luminescent compounds contained in the first, second, third, and fourth luminescent layers are the same compound. That is, it is also preferable that the first, second, third, and fourth luminescent compounds are the same compound.
[0515] In one embodiment of the organic EL element according to this embodiment, the first, second, third, and fourth light-emitting compounds are each independently at least one compound selected from the group consisting of compounds represented by formula (5), compounds represented by formula (6), and compounds represented by formula (3A).
[0516] (The compound represented by formula (5)) In one embodiment of the organic EL element according to this embodiment, the light-emitting compound is a compound represented by the following formula (5).
[0517] [ka]
[0518] (In formula (5) above, R 501 ~R 507 and R 511 ~R 517 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 501 ~R 507 and R 511 ~R 517 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 521 and R 522 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0519] In luminescent compounds, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. Preferably, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another.
[0520] "R 501 ~R 507 and R 511 ~R 517 "A set of two or more adjacent elements" is, for example, R 501 and R 502 A group consisting of R 502 and R 503 A group consisting of R 503 and R 504 A group consisting of R 505 and R 506A group consisting of R 506 and R 507 A group consisting of R 501 and R 502 and R 503 This is a combination of sets and other elements.
[0521] In one embodiment, the compound represented by formula (5) is the compound represented by the following formula (52).
[0522] [ka]
[0523] (In the above formula (52), R 531 ~R 534 and R 541 ~R 544 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 531 ~R 534 , R 541 ~R 544 , and R 551 and R 552 Each of them operates independently. hydrogen atom, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 561 ~R 564 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0524] R 561 ~R 564Each of these groups is preferably independently a substituted or unsubstituted aryl group having 6 to 18 carbon atoms in the ring, more preferably a substituted or unsubstituted aryl group having 6 to 14 carbon atoms in the ring, and even more preferably a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.
[0525] (The compound represented by formula (6)) In one embodiment of the organic EL element according to this embodiment, the light-emitting compound is a compound represented by the following formula (6).
[0526] [ka]
[0527] (In the above formula (6), Rings a, b, and c are each independent of the others. A substituted or unsubstituted ring-forming aromatic hydrocarbon ring with 6 to 50 carbon atoms, or These are heterocycles with 5 to 50 ring-forming atoms, either substituted or unsubstituted. R 601 and R 602 Each of these rings independently bonds with the a, b, or c ring to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R that does not form the aforementioned substituted or unsubstituted heteroalgebra 601 and R 602 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0528] In one embodiment of the organic EL element according to this embodiment, the a-ring, b-ring, and c-ring are rings that condense into the central condensed bi-ring structure of formula (6) composed of a boron atom and two nitrogen atoms (substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 ring-forming carbon atoms, or substituted or unsubstituted heterocycles with 5 to 50 ring-forming atoms).
[0529] The aromatic hydrocarbon rings of rings a, b, and c have the same structure as compounds in which a hydrogen atom has been introduced to an aryl group. The "aromatic hydrocarbon ring" of ring a includes three carbon atoms on the central condensed biring structure of formula (6) as ring-forming atoms. The "aromatic hydrocarbon rings" of rings b and c include two carbon atoms on the central condensed two-ring structure of formula (6) as ring-forming atoms.
[0530] Specific examples of "substituted or unsubstituted ring-forming aromatic hydrocarbon rings with 6 to 50 carbon atoms" include compounds in which a hydrogen atom has been introduced to the "aryl group" described in specific example group G1. The heterocyclic rings of the a, b, and c rings have the same structure as compounds in which a hydrogen atom is introduced into the heterocyclic group described above. The heterocycle of ring a contains three carbon atoms on the central fused biring structure of formula (6) as ring-forming atoms. The heterocycles of rings b and c contain two carbon atoms on the central fused biring structure of formula (6) as ring-forming atoms. Specific examples of "heterocycles with 5 to 50 substituted or unsubstituted ring-forming atoms" include compounds in which hydrogen atoms are introduced into the "heterocycle group" described in specific example group G2.
[0531] R 601 and R 602 Each of these may independently bond with a ring a, a ring b, or a ring c to form a substituted or unsubstituted heterocycle. In this case, the heterocycle contains a nitrogen atom on the central fused biring structure of formula (6). In this case, the heterocycle may also contain heteroatoms other than nitrogen. 601 and R 602 Specifically, when it is said that it bonds with ring a, ring b, or ring c, it means that it bonds with an atom constituting ring a, ring b, or ring c and R 601 and R602 This means that the atoms that make up the compound are bonded together. For example, R 601 It binds to the a ring, R 601 A nitrogen-containing heterocycle of two-ring condensation (or three-ring condensation or more) may be formed by the condensation of a ring containing a nitrogen ring with an a-ring. Specific examples of such nitrogen-containing heterocycles include compounds from specific example group G2 that correspond to two-ring condensation or more heterocyclic groups containing nitrogen. R 601 When it bonds with the b ring, R 602 When it bonds with the a ring, and R 602 The same applies when it is bonded to a c-ring. R 601 and R 602 Each of these elements does not necessarily have to be bonded to an a-ring, b-ring, or c-ring independently.
[0532] In one embodiment, the a-ring, b-ring, and c-ring in formula (6) are each independently substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring-forming carbon atoms. In one embodiment, the a-ring, b-ring, and c-ring in formula (6) are each independently a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring.
[0533] In one embodiment, R in formula (6) 601 and R 602 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, preferably a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.
[0534] In one embodiment, the compound represented by formula (6) is the compound represented by the following formula (62).
[0535] [ka]
[0536] (In formula (62) above, R 601A R611 and R 621 It combines with one or more elements selected from the group consisting of to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R 602A R 613 and R 614 It combines with one or more elements selected from the group consisting of to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R that does not form the aforementioned substituted or unsubstituted heteroalgebra 601A and R 602A Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 611 ~R 621 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted heterocycle, does not form the aforementioned substituted or unsubstituted monocycle, and does not form the aforementioned substituted or unsubstituted fused ring. 611 ~R 621 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted. (In the above formula (62), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905are the same as or different from each other, R 906 when there are a plurality of R, the plurality of R 906 are the same as or different from each other, R 907 when there are a plurality of R, the plurality of R 907 are the same as or different from each other.)
[0537] R in the formula (62) 601A and R 602A each correspond to R in the formula (6) 601 and R 602 respectively. For example, R 601A and R 611 may combine to form a nitrogen-containing heterocyclic ring in which a benzene ring corresponding to the a-ring is condensed with a ring containing these, such as a bicyclic condensation (or tricyclic condensation or more). Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the bicyclic condensation or more heterocyclic groups containing nitrogen among the specific example group G2. When R 601A and R 621 combine, when R 602A and R 613 combine, and when R 602A and R 614 combine, it is the same as above. [[ID= [ka]
[0541] (In the above formula (42-2), R 611 ~R 617 , R 601A and R 602A Each of these independently corresponds to R in equation (62) above. 611 ~R 617 , R 601A and R 602A It is synonymous with, X4 is an oxygen atom or a sulfur atom. R 701 ~R 704 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 701 ~R 704 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. In the above equation (42-2), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 Each of these independently corresponds to R in equation (62) above. 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 (This is synonymous with...)
[0542] (The compound represented by formula (3A)) In one embodiment of the organic EL element according to this embodiment, the light-emitting compound is a compound represented by the following formula (3A).
[0543] [ka]
[0544] (In the above formula (3A), Ra 301 Ra 302 Ra 303 Ra 304 Ra 305 Ra 306 Ra 307 Ra 308 Ra 309 and Ra 310 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, Ra 301 ~Ra 310 At least one of them is a monovalent group represented by the following formula (31A), Ra which does not form the single ring, does not form the condensed ring, and is not a monovalent group represented by the following formula (31A) 301 ~Ra 310 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, 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 group represented by -N(R 906 )(R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.)
[0545]
Chemical formula
[0546] (In the above formula (31A), Ara 301 and Ara 302 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, and La 301 , La 302 and La 303 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms, and * indicates the bonding position in the pyrene ring in the above formula (3A).)
[0547] (Specific examples of the luminescent compound) Specific examples of the luminescent compound are described below, but these are merely illustrative, and the luminescent compound is not limited to the following specific examples.
[0548]
Chemical formula
[0549] (Relationship between host material and luminescent compound) In this embodiment, it is preferable that the triplet energy T1(H1) of the first host material and the triplet energy T1(D1) of the first luminescent compound satisfy the relationship shown in the following formula (Equation 1B). T1(D1)>T1(H1) …(Math 1B)
[0550] Because the first host material and the first luminescent compound satisfy the relationship shown in equation (Equation 1B), triplet excitons generated in the first luminescent layer move over the first host material rather than the first luminescent compound, which has a higher triplet energy, making it easier for them to move to the second luminescent layer.
[0551] In this embodiment, it is preferable that the singlet energy S1(H1) of the first host material and the singlet energy S1(D1) of the first luminescent compound satisfy the relationship shown in the following formula (Equation 1C). The singlet energy S1 refers to the energy difference between the lowest excited singlet state and the ground state. S1(H1)>S1(D1) …(Math 1C)
[0552] When the first host material and the first luminescent compound satisfy the relationship shown in equation (Equation 1C), singlet excitons generated on the first host material can easily transfer energy from the first host material to the first luminescent compound, contributing to the fluorescence emission of the first luminescent compound.
[0553] In this embodiment, it is preferable that the singlet energy S1(H2) of the second host material and the singlet energy S1(D2) of the second luminescent compound satisfy the relationship shown in the following formula (Equation 1D). S1(H2)>S1(D2) …(Math 1D)
[0554] In this embodiment, the second luminescent compound and the second host material satisfy the relationship shown in equation (Equation 1D). As a result, the singlet energy of the second luminescent compound 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 luminescent compound, contributing to the fluorescence emission of the second luminescent compound.
[0555] In this embodiment, it is preferable that the triplet energy T1(D2) of the second luminescent compound and the triplet energy T1(H2) of the second host material satisfy the following equation (Equation 1E). T1(D2)>T1(H2) …(Math 1E)
[0556] In this embodiment, the relationship between the second luminescent compound and the second host material satisfies the relationship shown in equation (Equation 1E). As a result, when triplet excitons generated in the first luminescent layer move to the second luminescent layer, they transfer energy to the molecules of the second host material rather than to the second luminescent compound, 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 luminescent compound, which has a higher triplet energy. Triplet excitons generated by recombination on the molecules of the second luminescent compound rapidly transfer energy to the molecules of the second host material. Singlet excitons are generated on the second host material by the TTF phenomenon, through efficient collisions between triplet excitons on the second host material without the triplet excitons moving to the second luminescent compound.
[0557] In this embodiment, it is preferable that the triplet energy T1(H3) of the third host material and the triplet energy T1(D3) of the third luminescent compound satisfy the relationship shown in the following formula (Equation 2B). T1(D3)>T1(H3) …(Math 2B)
[0558] Because the third host material and the third luminescent compound satisfy the relationship shown in equation (Equation 2B), triplet excitons generated in the third luminescent layer move along the third host material rather than the third luminescent compound, which has a higher triplet energy, making it easier for them to move to the fourth luminescent layer.
[0559] In this embodiment, it is preferable that the singlet energy S1(H3) of the third host material and the singlet energy S1(D3) of the third luminescent compound satisfy the relationship shown in the following formula (Equation 2C). S1(H3)>S1(D3) …(Math 2C)
[0560] When the third host material and the third luminescent compound satisfy the relationship shown in equation (Equation 2C), singlet excitons generated on the third host material can easily transfer energy from the third host material to the third luminescent compound, contributing to the fluorescence emission of the third luminescent compound.
[0561] In this embodiment, it is preferable that the triplet energy T1(D4) of the fourth luminescent compound and the triplet energy T1(H4) of the fourth host material satisfy the following equation (Equation 2D). T1(D4)>T1(H4) …(Math 2D)
[0562] In this embodiment, the fourth luminescent compound and the fourth host material satisfy the relationship shown in equation (Equation 2D). As a result, when triplet excitons generated in the third luminescent layer move to the fourth luminescent layer, they transfer energy to the molecules of the fourth host material rather than to the fourth luminescent compound, which has a higher triplet energy. Furthermore, triplet excitons generated by the recombination of holes and electrons on the fourth host material do not move to the fourth luminescent compound, which has a higher triplet energy. Triplet excitons generated by recombination on the molecules of the fourth luminescent compound rapidly transfer energy to the molecules of the fourth host material. Singlet excitons are generated on the fourth host material by the TTF phenomenon, through efficient collisions between triplet excitons on the fourth host material without the triplet excitons moving to the fourth luminescent compound.
[0563] In this embodiment, it is preferable that the singlet energy S1(H4) of the fourth host material and the singlet energy S1(D4) of the fourth luminescent compound satisfy the relationship shown in the following formula (Equation 2E). S1(H4)>S1(D4) …(Math 2E)
[0564] In this embodiment, the fourth luminescent compound and the fourth host material satisfy the relationship shown in equation (Equation 2E). As a result, the singlet energy of the fourth luminescent compound is smaller than the singlet energy of the fourth host material. Therefore, singlet excitons generated by the TTF phenomenon transfer energy from the fourth host material to the fourth luminescent compound, contributing to the fluorescence emission of the fourth luminescent compound.
[0565] In this embodiment, it is also preferable that the first light-emitting layer and the second light-emitting layer are in direct contact.
[0566] 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) A configuration in which, during the process of depositing the compound relating to the first light-emitting layer and the process of depositing 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) In a configuration in which the first light-emitting layer and the second light-emitting layer contain a luminescent compound, a region in which the first host material, the second host material, and the luminescent compound are mixed 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 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.
[0567] In this embodiment, it is also preferable that the third light-emitting layer and the fourth light-emitting layer are in direct contact.
[0568] In this specification, the layer structure in which "the third light-emitting layer and the fourth light-emitting layer are in direct contact" may also include, for example, any of the following embodiments (LS4), (LS5), and (LS6). (LS4) A configuration in which, during the process of depositing the compound relating to the third light-emitting layer and the process of depositing the compound relating to the fourth light-emitting layer, a region is created in which both the third host material and the fourth host material are mixed, and this region is located at the interface between the third light-emitting layer and the fourth light-emitting layer. (LS5) In a configuration in which the third light-emitting layer and the fourth light-emitting layer contain a luminescent compound, a region in which the third host material, the fourth host material, and the luminescent compound are mixed is generated during the process of vapor deposition of the compound relating to the third light-emitting layer and the vapor deposition of the compound relating to the fourth light-emitting layer, and this region is located at the interface between the third light-emitting layer and the fourth light-emitting layer. (LS6) A configuration in which, when the third light-emitting layer and the fourth light-emitting layer contain a light-emitting compound, a region made of the light-emitting compound, a region made of the third host material, or a region made of the fourth host material is generated during the process of vapor deposition of the compound relating to the third light-emitting layer and the compound relating to the fourth light-emitting layer, and such region is located at the interface between the third light-emitting layer and the fourth light-emitting layer.
[0569] (Content in the luminescent layer) In one embodiment of the organic EL element according to this embodiment, the first light-emitting layer contains a first light-emitting compound in an amount of 0.5% by mass or more of the total mass of the first light-emitting layer. In one embodiment of the organic EL element according to this embodiment, the first light-emitting layer contains a first light-emitting compound in an amount of 10% by mass or less, 7% by mass or less, or 5% by mass or less of the total mass of the first light-emitting layer.
[0570] In one embodiment of the organic EL element according to this embodiment, the first light-emitting layer contains the first host material in an amount of 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more of the total mass of the first light-emitting layer. In one embodiment of the organic EL element according to this embodiment, the first light-emitting layer contains the first host material in an amount of 99.5% by mass or less, or 99% by mass or less, of the total mass of the first light-emitting layer. When the first light-emitting layer contains a first host material and a first light-emitting compound, the upper limit of the total content of the first host material and the first light-emitting compound is 100% by mass.
[0571] In this embodiment, the first light-emitting layer may contain only the first host material and the first light-emitting compound.
[0572] In one embodiment of the organic EL element according to this embodiment, the content of the third host material and the third luminescent compound in the third light-emitting layer can be within the range of the content of the first host material and the first luminescent compound in the first light-emitting layer described above.
[0573] In this embodiment, the third light-emitting layer may contain only the third host material and the third light-emitting compound.
[0574] In one embodiment of the organic EL element according to this embodiment, the second light-emitting layer contains a second light-emitting compound in an amount of 0.5% by mass or more of the total mass of the second light-emitting layer. In one embodiment of the organic EL element according to this embodiment, the second light-emitting layer contains a second light-emitting compound in an amount of 10% by mass or less, 7% by mass or less, or 5% by mass or less of the total mass of the second light-emitting layer.
[0575] In one embodiment of the organic EL element according to this embodiment, the second light-emitting layer contains the second host material in an amount of 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more of the total mass of the second light-emitting layer. In one embodiment of the organic EL element according to this embodiment, the second light-emitting layer contains the second host material in an amount of 99.5% by mass or less, or 99% by mass or less, of the total mass of the second light-emitting layer. If the second light-emitting layer contains a second host material and a second light-emitting compound, the upper limit of the total content of the second host material and the second light-emitting compound is 100% by mass.
[0576] In this embodiment, the second light-emitting layer may contain only the second host material and the second light-emitting compound.
[0577] In one embodiment of the organic EL element according to this embodiment, the content of the fourth host material and the fourth luminescent compound in the fourth light-emitting layer can be within the range of the content of the second host material and the second luminescent compound in the second light-emitting layer described above.
[0578] In this embodiment, the fourth light-emitting layer may contain only the fourth host material and the fourth light-emitting compound.
[0579] (film thickness of the light-emitting layer) In one embodiment of the organic EL element according to this embodiment, the film thickness of the first light-emitting layer and the third light-emitting layer are each independently 3 nm or more. If the film thickness of the first light-emitting layer and the third light-emitting layer is 3 nm or more, it is a sufficient film thickness for hole-electron recombination to occur in the first light-emitting layer and the third light-emitting layer. In one embodiment of the organic EL element according to this embodiment, the film thickness of the first light-emitting layer and the third light-emitting layer are independently 15 nm or less. If the film thickness of the first light-emitting layer and the third light-emitting layer is 15 nm or less, the film thickness is thin enough for the movement of triplet excitons from the first light-emitting layer to the second light-emitting layer and from the third light-emitting layer to the fourth light-emitting layer to occur. In one embodiment of the organic EL element according to this embodiment, the film thickness of the first light-emitting layer and the third light-emitting layer are, independently, 3 nm or more and 15 nm or less.
[0580] In one embodiment of the organic EL element according to this embodiment, the film thickness of the second light-emitting layer and the fourth light-emitting layer are, independently, 5 nm or more, or 10 nm or more. If the film thickness of the second light-emitting layer and the fourth 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 and return to the first light-emitting layer, and also suppress triplet excitons that have moved from the third light-emitting layer to the fourth light-emitting layer and return to the first light-emitting layer. Furthermore, if the film thickness of the second light-emitting layer and the fourth light-emitting layer is 5 nm or more, triplet excitons can be fully separated from the recombination portion in the first light-emitting layer and the recombination portion in the third light-emitting layer. In the organic EL element according to this embodiment, the film thickness of the second light-emitting layer and the fourth light-emitting layer are preferably 25 nm or less, independently of each other. If the film thickness of the second light-emitting layer and the fourth light-emitting layer are 25 nm or less, the density of triplet excitons in the second light-emitting layer and the triplet excitons in the fourth light-emitting layer can be increased, making the TTF phenomenon more likely to occur. In one embodiment of the organic EL element according to this embodiment, the film thickness of the second light-emitting layer and the fourth light-emitting layer are, independently, 5 nm or more and 25 nm or less.
[0581] In the organic EL element according to this embodiment, it is preferable that the film thickness of the first light-emitting layer is smaller than the film thickness of the second light-emitting layer, and the film thickness of the third light-emitting layer is smaller than the film thickness of the fourth light-emitting layer.
[0582] <Charge generation band> In this embodiment, it is preferable that the charge generation band is located between at least one pair of light-emitting units selected from two or more light-emitting units.
[0583] In this embodiment, it is preferable that the first charge generation band is located between the first light-emitting unit and the second light-emitting unit.
[0584] In this embodiment, it is preferable that each charge generation band independently includes at least one charge generation layer. It is preferable that at least one of the charge generation bands includes two or more charge generation layers. It is also preferable that each charge generation band independently includes two or more charge generation layers. The charge generation layer may also be called an intermediate layer, intermediate electrode, intermediate conductive layer, electron extraction layer, connecting layer, or intermediate insulating layer.
[0585] The charge generation band is the band in which at least one of holes and electrons is generated when a voltage is applied to an organic EL element. The charge generation band supplies electrons to the layer located on the anode side of the charge generation band. The charge generation band also supplies holes to the layer located on the cathode side of the charge generation band.
[0586] In this embodiment, it is preferable that at least one of the charge generation bands includes two charge generation layers, namely a first charge generation layer and a second charge generation layer. The first charge generation band may consist of one charge generation layer, or it may consist of two charge generation layers, including the first charge generation layer and the second charge generation layer.
[0587] In this embodiment, a first charge generation band is included between the first light-emitting unit and the second light-emitting unit, and it is preferable that the first charge generation band includes a first charge generation layer and a second charge generation layer located closer to the second light-emitting unit than the first charge generation layer.
[0588] In this embodiment, when the charge generation band is composed of a plurality of charge generation layers, it is preferable that the charge generation band has an N-type charge generation layer that injects electrons into the light-emitting unit and a P-type charge generation layer that injects holes into the light-emitting unit. It is preferable that the N-type charge generation layer is in direct contact with the light-emitting unit located on the anode side of the charge generation band. It is preferable that the P-type charge generation layer is in direct contact with the light-emitting unit located on the cathode side of the charge generation band.
[0589] In this embodiment, it is preferable that one of the N-type charge generation layer and the P-type charge generation layer is the first charge generation layer. In this embodiment, it is also preferable that the N-type charge generation layer is the first charge generation layer and the P-type charge generation layer is the second charge generation layer.
[0590] In this embodiment, examples of materials that can be used for the charge generation layer in the charge generation band include known materials that can be used for the charge generation layer of a tandem type organic EL element.
[0591] In this embodiment, the first charge generation layer preferably contains an electron transport band material. The electron transport band material contained in the first charge generation layer and the electron transport band material contained in the layer within the electron transport band are either the same compound or different compounds. The first charge generation layer preferably contains at least one derivative selected from the group consisting of phenanthroline derivatives, imidazole derivatives, benzimidazole derivatives, azine derivatives, and carbazole derivatives.
[0592] In this embodiment, the first charge generation layer may contain at least one selected from the group consisting of metals and metal compounds. In this embodiment, the first charge generation layer may also preferably contain an electron transport band material and at least one selected from the group consisting of metals and metal compounds. In this embodiment, the metal that may be contained in the first charge generation layer is, for example, at least one metal selected from the group consisting of rare earth metals, alkali metals, and alkaline earth metals. The metal that may be contained in the first charge generation layer is, for example, at least one metal selected from the group consisting of ytterbium, erbium, lithium, cesium, magnesium, and calcium. The metal compound that may be contained in the first charge generation layer is, for example, at least one metal compound selected from the group consisting of alkali metal compounds and alkaline earth metal compounds. The metal compound that the first charge generation layer may contain is, for example, at least one metal compound selected from the group consisting of 8-(quinolinolato)lithium (abbreviated as Liq), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), 2-(2-pyridyl)phenolate (abbreviated as LiPP), 2-(2-pyridyl)-3-pyridinolatritium (abbreviated as LiPPy), 4-phenyl-2-(2-pyridyl)phenolate (abbreviated as LiPPP), lithium oxide (LiOx), and cesium carbonate.
[0593] In this embodiment, the second charge generation layer preferably contains a hole transport band material and an acceptor material. The hole transport band material contained in the second charge generation layer and the hole transport band material contained in the layer within the hole transport band are either the same compound or different compounds. The second charge generation layer preferably contains at least one derivative selected from the group consisting of aromatic amine derivatives and carbazole derivatives.
[0594] <Hole transport band> In this embodiment, it is preferable that two or more light-emitting units each independently include a hole transport band. Each hole transport band independently includes one or more layers. In this embodiment, it is preferable that each hole transport band in each light-emitting unit independently includes at least one selected from the group consisting of an electron barrier layer, a hole transport layer, and a hole injection layer.
[0595] In this embodiment, the first light-emitting unit preferably includes a first hole transport band, and the second light-emitting unit preferably includes a second hole transport band. The first hole transport band is preferably located between the first light-emitting band and the anode. If the first light-emitting unit is the light-emitting unit located closest to the anode, it is preferable that the first hole transport band and the anode are in direct contact.
[0596] In this embodiment, the second hole transport band is preferably located between the first light emission band and the second light emission band. If the first charge generation band is located between the first light emission unit and the second light emission unit, the second hole transport band is preferably located between the first charge generation band and the second light emission band. In this case, the second hole transport band is preferably in direct contact with the first charge generation band, and more preferably in direct contact with the second charge generation layer. The second hole transport band is preferably in direct contact with the second light emission band.
[0597] In this embodiment, the first light-emitting unit includes a first hole transport band, the second light-emitting unit includes a second hole transport band, the first hole transport band is included between the anode and the first light-emitting band, the second hole transport band is included between the first charge generation band and the second light-emitting band, the first hole transport band and the second hole transport band each independently include one or more layers, and preferably at least one of the one or more layers included in the first hole transport band and at least one of the one or more layers included in the second hole transport band each independently contain a monoamine compound.
[0598] In this embodiment, it is preferable that the first hole transport band and the second hole transport band each independently include at least one selected from the group consisting of an electron barrier layer, a hole transport layer, and a hole injection layer.
[0599] In this embodiment, it is preferable that each of the layers in the hole transport band (e.g., the electron barrier layer, the hole transport layer, and the hole injection layer) independently contains a hole transport band material.
[0600] (Hole transport zone material) In this embodiment, the material containing the hole transport band is referred to as the hole transport band material. Preferably, the hole transport band material is a material that can be used in layers that may be included in the hole transport band (e.g., an electron barrier layer, a hole transport layer, and a hole injection layer). The hole transport band material can also be used in the charge generation band.
[0601] In one embodiment of the organic EL element according to this embodiment, the hole transport band material may be at least one compound selected from the group consisting of compounds represented by the following formula (C1) and compounds represented by the formula (C3).
[0602] [ka]
[0603] (In the above formula (C1), L A1 , L A2 and L A3 Each of them operates independently. single bond, Substituted or unsubstituted ring-forming arylene groups with 6 to 50 carbon atoms, A substituted or unsubstituted divalent heterocyclic group with 5 to 50 ring-forming atoms, or A divalent group formed by bonding two or three groups selected from the group consisting of substituted or unsubstituted arylene groups having 6 to 50 ring-forming carbon atoms and substituted or unsubstituted divalent heterocyclic groups having 5 to 50 ring-forming atoms. Ar 111 Ar 112 and Ar 113 Each of them operates independently. Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or -Si(R C1 )(R C2 )(R C3 ) and R C1 , RC2 and R C3 These are, independently, substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms. R C1 If multiple R C1 They are either identical or different from each other. R C2 If multiple R C2 They are either identical or different from each other. R C3 If multiple R C3 They are either identical or different to one another.
[0604] [ka]
[0605] (In the above formula (C3), L C1 , L C2 , L C3 and L C4 Each of them operates independently. single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, n2 is 1, 2, 3, or 4. If n2 is 1, L C5 teeth, A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, If n2 is 2, 3, or 4, then multiple L C5 They are either identical or different from each other. If n2 is 2, 3, or 4, then multiple L C5 teeth, They combine with each other to form a substituted or unsubstituted monoring, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, L that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring C5 teeth, A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, Ar 131 Ar 132 Ar 133 and Ar 134 Each of them operates independently. Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or -Si(R C1 )(R C2 )(R C3 ) and R C1 , R C2 and R C3 These are, independently, substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms. R C1 If multiple R C1 They are either identical or different from each other. R C2 If multiple R C2 They are either identical or different from each other. R C3 If multiple R C3 They are either identical or different to one another.
[0606] In one embodiment of the organic EL element according to this embodiment, the first amino group represented by the following formula (C3-1) and the second amino group represented by the following formula (C3-2) in the compound represented by formula (C3) are the same group.
[0607] [ka]
[0608] (In the above formulas (C3-1) and (C3-2), * represents LC5 This is the bonding position.
[0609] In one embodiment of the organic EL element according to this embodiment, the first amino group represented by formula (C3-1) and the second amino group represented by formula (C3-2) may be different groups from each other.
[0610] In this embodiment, the hole transport band material is preferably at least one amine compound selected from the group consisting of a monoamine compound having one substituted or unsubstituted amino group in the molecule, a diamine compound having two substituted or unsubstituted amino groups in the molecule, a triamine compound having three substituted or unsubstituted amino groups in the molecule, and a tetraamine compound having four substituted or unsubstituted amino groups in the molecule.
[0611] In this embodiment, the hole transport band material is more preferably a monoamine compound having one substituted or unsubstituted amino group in the molecule, or a diamine compound having two substituted or unsubstituted amino groups in the molecule, and even more preferably a monoamine compound having one substituted or unsubstituted amino group in the molecule.
[0612] (Specific examples of hole transport zone materials) Specific examples of hole transport band materials include the following compounds. However, the present invention is not limited to these specific examples of hole transport band materials.
[0613] [ka]
[0614] [ka]
[0615] (Electron barrier layer) The electron barrier layer is preferably a layer that transports holes and prevents electrons from reaching the layer on the anode side of the electron barrier layer (for example, the hole transport layer). In the organic EL element 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 hole transport band material. 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 be a layer that prevents excitons generated in the light-emitting layer from moving to layers on the anode side of the electron barrier layer (for example, hole transport layers and hole injection layers) so that excitation energy does not leak from the light-emitting layer to the surrounding layers.
[0616] (Hole injection layer) In one embodiment of the organic EL element according to this embodiment, a hole injection layer is arranged between the anode and the light-emitting band. In one embodiment of the organic EL element according to this embodiment, the anode and the hole injection layer are in direct contact. In one embodiment of the organic EL element according to this embodiment, the hole injection layer and the hole transport layer are in direct contact.
[0617] The hole injection layer is a layer containing a material with high hole injection properties. Suitable 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) are also examples. Furthermore, polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used as materials with high hole injection properties. Examples of polymer 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). In addition, 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.
[0618] In one embodiment of the organic EL element according to this embodiment, a compound that can be used in the hole transport layer (hole transport band material) can also be used in the hole injection layer. In this case, it is preferable that the hole injection layer contains both a hole transport band material and an acceptor material.
[0619] (Acceptor material) The acceptor material includes at least one of a first ring structure represented by the following formula (P11) and a second ring structure represented by the following formula (P12).
[0620] [ka]
[0621] (The first ring structure represented by formula (P11) is condensed in the molecule of the acceptor material with at least one of the ring structures of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted heterocycle having 5 to 50 ring-forming atoms.) = Z 10 The structure represented by (P11a), (P11b), (P11c), (P11d), (P11e), (P11f), (P11g), (P11h), (P11i), (P11j), (P11k), or (P11m) is represented by the following formulas:
[0622] [ka]
[0623] [ka]
[0624] (In the above formulas (P11a), (P11b), (P11c), (P11d), (P11e), (P11f), (P11g), (P11h), (P11i), (P11j), (P11k), or (P11m), R 11 ~R 14 R 111 ~R 120Each of them operates independently. hydrogen atom, halogen atom, Hydroxyl group, Cyano group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0625] (In the above formula (P12), Z1 to Z5 are each independent of each other.) Nitrogen atom, R 15 A carbon atom that bonds with it, or The carbon atom that bonds with other atoms in the molecule of the acceptor material, Of Z1 to Z5, at least one is a carbon atom that bonds with other atoms in the molecule of the acceptor material. R 15 teeth, hydrogen atom, halogen atom, Cyano group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, Carboxy group, Substituted or unsubstituted ester groups, Substituted or unsubstituted carbamoyl groups, Nitro group, and Selected from the group consisting of substituted or unsubstituted siloxanil groups, R 15 If multiple R 15 They are either identical or different.
[0626] (In the aforementioned acceptor material, R 901 ~R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If there are multiple R 901 They are either identical or different from each other. R 902 If there are multiple R 902 They are either identical or different from each other. R 903 If there are multiple R 903They are either identical or different from each other. R 904 If there are multiple R 904 They are either identical or different from each other. R 905 If there are multiple R 905 They are either identical or different from each other. R 906 If there are multiple R 906 They are either identical or different from each other. R 907 If there are multiple R 907 They are either identical or different to one another.
[0627] In one embodiment of the organic EL element according to this embodiment, the acceptor material has at least one cyano group.
[0628] In one embodiment of the organic EL element according to this embodiment, the hole injection layer contains a hole transport band material, the acceptor material and the hole transport band material are different from each other, and the content of the acceptor material in the hole injection layer is less than 50% by mass.
[0629] In one embodiment of the organic EL element according to this embodiment, the content of acceptor material in the hole injection layer is 10% by mass or less, or 5% by mass or less.
[0630] In one embodiment of the organic EL element according to this embodiment, the content of the acceptor material in the hole injection layer is 0.5% by mass or more, 1% by mass or more, or 3% by mass or more.
[0631] In one embodiment of the organic EL element according to this embodiment, when the hole injection layer contains an acceptor material and a hole transport band material, the content of the hole transport band material in the hole injection layer is preferably 40% by mass or more, more preferably 45% by mass or more, and even more preferably 50% by mass or more. The content of the hole transport band material in the hole injection layer is preferably 99.5% by mass or less. The total content of the acceptor material and the hole transport band material in the hole injection layer is 100% by mass or less.
[0632] In this specification, an ester group is at least one group selected from the group consisting of alkyl ester groups and aryl ester groups.
[0633] In this specification, alkyl ester groups are, for example, -C(=O)OR E It is represented as R E For example, this is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 10 carbon atoms).
[0634] In this specification, the aryl ester group is, for example, -C(=O)OR Ar It is represented as R Ar These are, for example, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms forming a ring.
[0635] In this specification, the siloxanyl group is a silicon compound group via an ether bond, such as a trimethylsiloxanyl group.
[0636] In this specification, the carbamoyl group is represented by -CONH2. Substituted carbamoyl groups in this specification are, for example, -CONH-Ar C , or -CONH-R C It is represented as Ar C This is, for example, at least one group selected from the group consisting of substituted or unsubstituted aryl groups with 6 to 50 (preferably 6 to 10) ring-forming carbon atoms and heterocyclic groups with 5 to 50 (preferably 5 to 14) ring-forming atoms. CThis may be a group formed by bonding a substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms to a substituted or unsubstituted heterocyclic group with 5 to 50 ring-forming atoms. C For example, this is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 6 carbon atoms).
[0637] In acceptor materials, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.
[0638] (Specific examples of acceptor materials) Examples of acceptor materials include the following compounds. However, the present invention is not limited to these specific examples of acceptor materials.
[0639] [ka]
[0640] [ka]
[0641] (Hole transport layer) The hole transport layer is a layer containing a substance with high hole transport capabilities. In one embodiment of the organic EL element according to this embodiment, the hole transport layer contains a hole transport band material. In one embodiment of the organic EL device according to this embodiment, the hole transport layer may contain a compound different from the hole transport band material described above. The hole transport layer may contain, for example, one or more compounds selected from the group consisting of aromatic amine compounds, carbazole derivatives, and anthracene derivatives. Specifically, the hole transport layer may contain 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), or 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino It may also contain aromatic amine compounds such as ]biphenyl (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), or 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB). The substances described herein are mainly 10 -6 cm 2 It is a substance having a hole mobility of / (V·s) or greater. The hole transport layer may use carbazole derivatives such as CBP, CzPA, and PCzPA, or anthracene derivatives such as t-BuDNA, DNA, and DPAnth. Alternatively, polymer compounds such as poly(N-vinylcarbazole) (PVK) or poly(4-vinyltriphenylamine) (PVTPA) can be used for the hole transport layer. However, any material with higher hole transport capabilities than electron transport may be used for the hole transport layer, different from those mentioned above. The hole transport layer may be a single layer or a multilayer structure consisting of two or more layers.
[0642] <Electron transport band> In this embodiment, it is preferable that two or more light-emitting units each independently include an electron transport band. Each electron transport band independently includes one or more layers. In this embodiment, it is preferable that each electron transport band in each light-emitting unit independently includes at least one selected from the group consisting of a hole barrier layer, an electron transport layer, and an electron injection layer.
[0643] In this embodiment, it is preferable that the first light-emitting unit includes a first electron transport band, and it is preferable that the second light-emitting unit includes a second electron transport band.
[0644] In this embodiment, the first electron transport band is preferably located between the first light emission band and the second hole transport band. If the first charge generation band is located between the first light emission unit and the second light emission unit, the first electron transport band is preferably located between the first light emission band and the first charge generation band. In this case, the first electron transport band is preferably in direct contact with the first charge generation band, and more preferably in direct contact with the first charge generation layer.
[0645] In this embodiment, it is preferable that the second electron transport band is located between the second light emission band and the cathode. If the second light emission unit is the light emission unit located closest to the cathode, it is preferable that the second electron transport band and the cathode are in direct contact.
[0646] In this embodiment, it is preferable that the first electron transport band and the second electron transport band each independently include at least one selected from the group consisting of a hole barrier layer, an electron transport layer, and an electron injection layer.
[0647] In this embodiment, the electron transport band may independently include two or more layers. In this case, the electron transport band preferably includes a hole barrier layer and an electron transport layer. It is also preferable that the electron transport band includes an electron transport layer and an electron injection layer.
[0648] In this embodiment, the electron transport band may include three or more layers, each independently. It is also preferable that the electron transport band includes three layers: a hole barrier layer, an electron transport layer, and an electron injection layer.
[0649] In the organic EL element according to this embodiment, the first light-emitting unit includes a first electron transport band, the second light-emitting unit includes a second electron transport band, the first electron transport band is included between the first light-emitting band and the first charge generation band, the second electron transport band is included between the second light-emitting band and the cathode, the first electron transport band and the second electron transport band each independently include one or more layers, and it is preferable that at least one layer among the one or more layers included in the first electron transport band and at least one layer among the one or more layers included in the second electron transport band each independently contain an azine compound.
[0650] In the organic EL element according to this embodiment, it is preferable that each layer in the electron transport band (for example, a hole barrier layer, an electron transport layer, and an electron injection layer) independently contains an electron transport band material.
[0651] (Electron transport band materials) In the organic EL element according to this embodiment, the material containing the electron transport band is referred to as the electron transport band material. The electron transport band material is preferably a material that can be used in layers that may be included in the electron transport band (for example, a hole barrier layer, an electron transport layer, and an electron injection layer). The electron transport band material can also be used in the charge generation band.
[0652] In one embodiment of the organic EL element according to this embodiment, the electron transport band material is a nitrogen-containing compound. Preferably, the nitrogen-containing compound as the electron transport band material has at least one of a five-membered ring containing a nitrogen atom and a six-membered ring containing a nitrogen atom.
[0653] In one embodiment of the organic EL device according to this embodiment, the electron transport band material is at least one compound selected from the group consisting of imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives. In one embodiment of the organic EL element according to this embodiment, the electron transport band contains at least one compound selected from the group consisting of imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives.
[0654] In one embodiment of the organic EL element according to this embodiment, the layer included in the electron transport band may contain at least one selected from the group consisting of metals and metal compounds. In one embodiment of the organic EL display device according to this embodiment, the layer included in the electron transport band may contain at least one selected from the group consisting of metals and metal compounds, and an electron transport band material. The metals and metal compounds that the electron transport band may contain are the same as the metals and metal compounds that the first charge generation layer described above may contain.
[0655] In this embodiment, if the first charge generation layer contains a phenanthroline derivative, it is also preferable that the first electron transport band of the first light-emitting unit does not contain a phenanthroline derivative. If the first charge generation layer contains a phenanthroline derivative, it is also preferable that the first hole barrier layer and the second light-emitting layer do not contain a phenanthroline derivative.
[0656] (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, for example, an electron transport band material. It is also preferable that the compound contained in the hole barrier layer is 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. Furthermore, 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 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.
[0657] (electron transport layer) The electron transport layer is a layer containing a material with high electron transport properties. The aforementioned electron transport band materials can be used in the electron transport layer. In addition, the electron transport layer can also use 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, as low molecular weight organic compounds, metal complexes such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviated as BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to metal complexes, there are also 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 2 It is a substance having an electron mobility of / (V·s) or greater. Furthermore, polymer compounds can also be used in the electron transport layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy) can be used. In the organic EL element according to this embodiment, the electron transport layer preferably contains an azine derivative as an electron transport band material. In the organic EL element according to this embodiment, the electron transport band material is preferably a diazine derivative or a triazine derivative, and more preferably a pyrimidine derivative or a 1,3,5-triazine derivative. Furthermore, any material with higher electron transport properties than hole transport properties may be used for the electron transport layer, different from the materials mentioned above. Also, the electron transport layer may be a single layer or a multilayer structure consisting of two or more layers stacked together.
[0658] In addition to the electron transport band materials mentioned above, other specific examples of electron transport band materials include the following compounds. However, the present invention is not limited to these specific examples of electron transport band materials.
[0659] [ka]
[0660] [ka]
[0661] [ka]
[0662] [ka]
[0663] (Phenanthroline derivative) The phenanthroline derivative is preferably a compound that has at least one group represented by the following formula (21) and is represented by the following formula (20).
[0664] [ka]
[0665] (In the above formula (20), X21 ~X 28 Each of these is independently a nitrogen atom and CR. 21 , or a carbon atom bonded to the group represented by formula (21), X 21 ~X 28 At least one of these is a carbon atom bonded to the group represented by formula (21), If there are multiple groups represented by formula (21), the multiple groups represented by formula (21) may be identical or different from each other. Multiple R 21 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 21 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 931 A base represented by -COOR 932A base represented by -S(=O)2R 933 A base represented by -B(R 934 )(R 935 A base represented by ) -P(=O)(R 936 )(R 937 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0666] (In the above formula (21), Ar2 is A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. p is 1, 2, 3, 4, or 5. If there are two or more Ar2 atoms, then the two or more Ar2 atoms are either identical or different from each other. L2 is a single bond or a linking group. L2 as a linking group, Substituted or unsubstituted linear, branched, or cyclic polyvalent aliphatic hydrocarbon groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming polyvalent aromatic hydrocarbon groups with 6 to 50 carbon atoms, A polyvalent heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or A polyvalent multiple linkage group formed by the bonding of two or three groups selected from the polyvalent aromatic hydrocarbon group and the polyvalent heterocyclic group, The aromatic hydrocarbon groups and heterocyclic groups constituting the plurality of linking groups are either identical or different from each other, and adjacent groups may bond to each other to form a ring, or they may not bond to each other. Ar2 and L2 as a linking group either bond to each other to form a ring, or they do not bond to each other. L2 acts as a linking group, and X is adjacent to the carbon atom bonded to L2.21 ~X 28 Any carbon atom or CR 21 R 21 They either bond to each other to form a ring, or they do not bond to each other. The asterisk (*) in formula (21) indicates the bonding position with the ring represented by formula (20).
[0667] (In the phenanthroline derivative, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 931 , R 932 , R 933 , R 934 , R 935 , R 936 and R 937 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. R 931 If multiple R 931 They are either identical or different from one another. R 932 If multiple R 932 They are either identical or different from one another. R 933 If multiple R 933 They are either identical or different from one another. R 934 If multiple R 934 They are either identical or different from one another. R 935 If multiple R 935 They are either identical or different from one another. R 936 If multiple R 936 They are either identical or different from one another. R 937 If multiple R 937 They are either identical or different to one another.
[0668] In this specification, -O-(R 904 The group represented by ) is R 904 If it is a hydrogen atom, it is a hydroxyl group. In this specification, -S-(R 905 The group represented by ) is R 905 If it is a hydrogen atom, it is a thiol group. In this specification, -S(=O)2R 933 The group represented by R 933 If it is a substituent, it is a substituted sulfo group. In this specification, -B(R 934 )(R 935 The group represented by ) is R 934 and R 935 If it is a substituent, it is a substituted boryl group. In this specification, -P(=O)(R 936 )(R 937 The group represented by ) is R 936 and R 937 If it is a substituent, it is a substituted phosphine oxide group, and R 936 and R 937 If it is an aryl group, it is an arylphosphoryl group.
[0669] The number of carbon atoms in the "unsubstituted linear, branched, or cyclic polyvalent aliphatic hydrocarbon group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "unsubstituted polyvalent aromatic hydrocarbon 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 polyvalent heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein.
[0670] In the Ar2 of formula (21), it is preferable that the heterocyclic group having 5 to 50 ring-forming atoms includes a substituted or unsubstituted group derived from the ring structure represented by formula (20).
[0671] X in equation (20) above 21 and X 28 However, it is also preferable that the carbon atom bonded to the group represented by formula (21) is a carbon atom. X in equation (20) above 21 and X 28 One of them is a carbon atom bonded to the group represented by formula (21), and X 21 and X 28 It is also preferable that the other atom is a carbon atom bonded to a hydrogen atom.
[0672] X in equation (20) above 21 ~X 28 Each of them independently, CR 21 Alternatively, it is preferable that it is a carbon atom bonded to the group represented by formula (21) above. X in equation (20) above 21 ~X 28 Of these, the carbon atoms other than those bonded to the group represented by formula (21) are CR 21 It is preferable that the compound represented by formula (20) is a 1,10-phenanthroline derivative.
[0673] In formula (21), Ar2 is preferably a substituted or unsubstituted ring-forming condensed aromatic hydrocarbon group having 8 to 20 carbon atoms.
[0674] The ring-forming condensed aromatic hydrocarbon group having 8 to 20 carbon atoms is also preferably a group derived from any aromatic hydrocarbon selected from the group consisting of naphthalene, anthracene, acephenanthrylene, acetanthrylene, benzoanthracene, triphenylene, pyrene, chrysene, naphthacene, fluorene, phenanthrene, fluoranthene, and benzofluoranthene.
[0675] In formula (21), Ar2 may also preferably be a substituted or unsubstituted anthyl group.
[0676] In formula (21), Ar2 is preferably a substituted or unsubstituted heterocyclic group having 5 to 40 ring-forming carbon atoms.
[0677] The Ar2 in formula (21) may also preferably be a substituted or unsubstituted group derived from the ring structure represented by formula (20).
[0678] (Specific examples of phenanthroline derivatives) Specific examples of phenanthroline derivatives include the following compounds. However, the present invention is not limited to these specific examples of phenanthroline derivatives.
[0679] [ka]
[0680] (electron injection layer) The electron injection layer is a layer containing a material with high electron injection potential. The electron injection layer can contain alkali metals, alkaline earth metals, rare earth metals, or compounds thereof, such as lithium (Li), cesium (Cs), calcium (Ca), ytterbium (Yb), erbium (Er), 8-(quinolinolato)lithium (Liq), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx). Alternatively, a material containing alkali metals, alkaline earth metals, rare earth metals, or compounds thereof in an electron-transporting material, specifically one 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 formed by mixing an organic compound and an electron donor may be used in the electron injection layer. Such a composite material exhibits 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 with excellent electron transport properties, and specifically, for example, electron transport band materials or materials mentioned in the description of the electron transport layer can be used. The electron donor can be any substance that exhibits electron-donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides and alkaline earth metal oxides are also preferred, such as lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (abbreviated as TTF) can also be used.
[0681] <Other components of the OLED display element> The configuration of the organic EL element according to this embodiment will be further described.
[0682] (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), such as a plastic substrate. 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.
[0683] (anode) In the organic EL element according to this embodiment, it is preferable to use metals, alloys, electrically conductive compounds, and mixtures thereof, each independently having a large work function (specifically, 4.0 eV or more), for the anode. 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). 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. Among the layers formed on the anode, for example, the layer formed in contact with the anode is formed using a composite material that allows for easy hole injection regardless of the anode's work function. Therefore, materials 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. 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.
[0684] When the organic EL element is of the bottom emission type, the anode is a light-transmitting electrode. The light-transmitting electrode is preferably formed of a metal material that is light-transmitting or semi-transmitting, allowing light emitted from the light-emitting layer to pass through. In this specification, light-transmitting or semi-transmitting means the property of transmitting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The light-transmitting or semi-transmitting metal material can be appropriately selected from the materials listed in the anode section above. The light-transmitting or semi-transmitting metal material may also be one of the materials listed below as materials to be used for the conductive layer (or transparent conductive layer).
[0685] When the organic EL element is of the top-emission type, the anode is a light-reflective electrode having a light-reflecting layer. The light-reflecting layer is preferably formed of a light-reflective metallic material. 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 light-reflective metallic material can be appropriately selected from the materials listed in the anode section. Examples of metallic materials used for the light-reflecting layer include: a single metal material selected from the group consisting of Al, Ag, Ta, Zn, Mo, W, Ni, and Cr; or an alloy material having a metal selected from this group as the main component (preferably 50% by mass or more of the total); an amorphous alloy selected from the group consisting of NiP, NiB, CrP, and CrB; or a microcrystalline alloy selected from the group consisting of NiAl and silver alloys. Furthermore, as the metal material used for the light-reflecting layer, at least one alloy selected from the group consisting of APC (an alloy of silver, palladium, and copper), ARA (an alloy of silver, rubidium, and gold), MoCr (an alloy of molybdenum and chromium), and NiCr (an alloy of nickel and chromium) may be used. The light-reflecting layer may be a single layer or a multi-layer layer.
[0686] The anode, as a light-reflective electrode, may consist only of a light-reflective layer, or it may be a multilayer structure having a light-reflective layer and a conductive layer (preferably a transparent conductive layer). When the anode is a multilayer structure having a light-reflective layer and a conductive layer, it is preferable that the conductive layer is placed between the reflective layer and a layer containing a hole transport band (for example, a hole injection layer or a first hole transport layer). Alternatively, the anode may be a multilayer structure in which a light-reflective layer is placed between two conductive layers (a first conductive layer and a second conductive layer). In such a multilayer structure, the first conductive layer and the second conductive layer may be formed of the same material or of different materials. In this specification, these multilayer structures may also be referred to as conductive material layers. The material used for the conductive layer can be appropriately selected from the materials listed in the section on the anode. Furthermore, for the conductive layer as a transparent electrode (transparent conductive layer), metals, alloys, electrically conductive compounds, and mixtures thereof with a large work function (specifically, 4.0 eV or higher) can also be used. Furthermore, the conductive layer may also be made of, for example, alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca) and strontium (Sr), alloys containing at least one selected from the group consisting of alkali metals and alkaline earth metals (e.g., MgAg and AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing at least one selected from rare earth metals.
[0687] (cathode) In the organic EL element according to this embodiment, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof with a small work function (specifically, 3.8 eV or less) for the cathode. Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these. 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. Furthermore, by providing an electron injection layer, cathodes can be formed using various conductive materials such as Al, Ag, ITO, graphene, silicon, or indium 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.
[0688] When the organic EL element is of the bottom emission type, the cathode is a light-reflective electrode. The light-reflective electrode is preferably formed from a light-reflective metallic material. The light-reflective metallic material can be appropriately selected from the materials listed in the cathode section. Alternatively, the light-reflective metallic material may be one of the materials listed above for use in the light-reflective layer.
[0689] When the organic EL element is of the top-emission type, the cathode is a light-transmitting electrode. The light-transmitting electrode is preferably made of a metal material that is light-transmitting or semi-transmitting, allowing light emitted from the light-emitting layer to pass through. Light-transmitting or semi-transmitting means the property of transmitting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The light-transmitting or semi-transmitting metal material can be appropriately selected from the materials listed in the cathode section above. The light-transmitting or semi-transmitting metal material may also be one of the materials listed above as materials used for the conductive layer (or transparent conductive layer).
[0690] (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 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). Alternatively, the capping layer may contain at least one compound selected from the group consisting of aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, or dibenzofuran derivatives. Furthermore, a laminate in which layers containing these materials are stacked can also be used as a capping layer.
[0691] The organic EL element according to this 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 of the 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 of the top-emission type, it is preferable that the anode is a light-reflecting electrode with light-reflecting properties and the cathode is a light-transmitting electrode with light-transmitting properties.
[0692] (film thickness) In this embodiment, the film thickness of each layer included in the organic EL element 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 organic compound layer of the organic EL element is usually preferably in the range of a few nanometers to 1 μm.
[0693] (Layer formation method) In this embodiment, the method for forming each layer of the organic EL element is not limited to those specifically mentioned above, but each layer of the organic EL element can be independently formed by selecting from known methods such as dry deposition and wet deposition. Examples of dry deposition methods include vacuum deposition, sputtering, plasma deposition, and ion plating. Examples of wet deposition methods include spin coating, dipping, flow coating, and inkjet deposition.
[0694] (Schematic configuration of an organic EL element) Figure 1 shows a schematic configuration of the organic EL element according to this embodiment. The organic EL element 1 shown in Figure 1 comprises a substrate 2, an anode 3, a cathode 4, a first light-emitting unit 10, a second light-emitting unit 20, and a first charge generation band 8.
[0695] The first light-emitting unit 10 is positioned between the anode 3 and the cathode 4. The first light-emitting unit 10 includes a first hole transport band 61, a first light emission band 51, and a first electron transport band 71. In the first light-emitting unit 10, the first hole transport band 61, the first light emission band 51, and the first electron transport band 71 are stacked in this order from the anode 3 side to the cathode 4 side. The first hole transport zone 61 includes a first hole injection layer 611, a first hole transport layer 612, and a first electron barrier layer 613. In the first hole transport zone 61, the first hole injection layer 611, the first hole transport layer 612, and the first electron barrier layer 613 are stacked in this order from the anode 3 side to the cathode 4 side. The first light-emitting band 51 includes a first light-emitting layer 511 and a second light-emitting layer 512. In the first light-emitting band 51, the first light-emitting layer 511 and the second light-emitting layer 512 are stacked in this order from the anode 3 side to the cathode 4 side. The first electron transport band 71 includes the first hole barrier layer 711.
[0696] The second light-emitting unit 20 is positioned between the first light-emitting unit 10 and the cathode 4. The second light-emitting unit 20 includes a second hole transport band 62, a second light emission band 52, and a second electron transport band 72. In the second light-emitting unit 20, the second hole transport band 62, the second light emission band 52, and the second electron transport band 72 are stacked in this order from the anode 3 side to the cathode 4 side. The second hole transport zone 62 includes a second hole transport layer 621 and a second electron barrier layer 622. In the second hole transport zone 62, the second hole transport layer 621 and the second electron barrier layer 622 are stacked in this order from the anode 3 side to the cathode 4 side. The second light-emitting band 52 includes the third light-emitting layer 521 and the fourth light-emitting layer 522. In the second light-emitting band 52, the third light-emitting layer 521 and the fourth light-emitting layer 522 are stacked in this order from the anode 3 side toward the cathode 4 side. The second electron transport band 72 includes a second hole barrier layer 721, a second electron transport layer 722, and a second electron injection layer 723. In the second electron transport band 72, the second hole barrier layer 721, the second electron transport layer 722, and the second electron injection layer 723 are stacked in this order from the anode 3 side to the cathode 4 side.
[0697] The first charge generation zone 8 is located between the first light-emitting unit 10 and the second light-emitting unit 20. The first charge generation zone 8 includes a first charge generation layer 81 and a second charge generation layer 82. In the first charge generation zone 8, the first charge generation layer 81 and the second charge generation layer 82 are stacked in this order from the anode 3 side to the cathode 4 side.
[0698] The present invention is not limited to the configuration of the organic EL element shown in Figure 1. For example, in an organic EL element with a different configuration, the number of stages of the light-emitting unit positioned between the anode and cathode may be three or more. Furthermore, in the case of a top-emission type organic EL element, a capping layer may be laminated on top of the cathode. The anode may also have the aforementioned multilayer structure; for example, a reflective layer and a conductive layer may be laminated in that order from the substrate side.
[0699] (Emitting color of organic EL elements) The organic EL element according to this embodiment preferably emits blue light. In this specification, blue light emission refers to light emission in which the maximum peak wavelength in the emission spectrum is in the range of 430 nm or more and 480 nm or less. The maximum peak wavelength is the peak wavelength in the emission spectrum at which the emission intensity is maximum.
[0700] In this embodiment, the maximum peak wavelength of light emitted from the organic EL element is preferably 430 nm or more and 480 nm or less.
[0701] When driving an organic EL element, the maximum peak wavelength of light emitted from the organic EL element is measured as follows: Current density is 10 mA / cm². 2The 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).
[0702] <Measurement method> (Triplet energy T1) The following methods can be used to measure the triplet energy T1. The compound to be measured is placed in EPA (diethyl ether:isopentane:ethanol = 5:5:2 (volume ratio)) and 10 -5 mol / L or more 10 -4 Dissolve the substance to a concentration of mol / L or less to obtain a solution, and place this solution in a quartz cell to use as 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 defined as the triplet energy T1. Conversion formula (F1): T1[eV]=1239.85 / λ edge
[0703] 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 considered the tangent to the rise of the phosphorescence spectrum on the short-wavelength side. Furthermore, maxima with peak intensity less than 15% of the maximum peak intensity of the spectrum are not included in the shortest wavelength maxima mentioned above. Instead, the tangent line drawn at the point closest to the shortest wavelength maxima, where the slope value is at its maximum, is considered the tangent line to the rising edge of the phosphorescence spectrum on the short wavelength side. For phosphorescence measurement, a Hitachi High-Technologies Corporation F-4500 spectrofluorometer can be used. However, the measuring apparatus is not limited to this; measurements may also be performed by combining a cooling device, a low-temperature container, an excitation light source, and a light-receiving device.
[0704] (Singlet energy S1) The following methods can be used to measure the singlet energy S1 using a solution (sometimes referred to as the solution method). 10 compounds to be measured -5 mol / L or more 10 -4 Prepare a toluene solution with a concentration of mol / L or less and place it in a quartz cell. Measure the absorption spectrum of this sample at room temperature (300K) (vertical axis: absorption intensity, horizontal axis: wavelength). Draw a tangent line to the falling edge of the absorption spectrum at longer wavelengths, 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): S1[eV]=1239.85 / λedge Examples of absorption spectrum measuring devices include, but are not limited to, Hitachi's spectrophotometer (device name: U3310).
[0705] The tangent to the falling edge of an absorption spectrum on the longer wavelength side is drawn as follows: Consider the tangents at each point on the spectral curve as we move along the spectral 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 absorbance values of 0.2 or less are not included in the maximum value at the longest wavelength mentioned above.
[0706] (Maximum peak wavelength of the compound) The method for measuring the maximum peak wavelength of a compound is as follows: 10 -6 mol / L or more 10 -5 Prepare a toluene solution with a concentration of mol / L or less and place it in a quartz cell. Measure the emission spectrum of this sample at room temperature (300K) (vertical axis: emission intensity, horizontal axis: wavelength). The emission spectrum can be measured using a spectrofluorometer (instrument 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. In the emission spectrum, the peak wavelength of the emission spectrum with the maximum emission intensity is defined as the maximum emission peak wavelength. In this specification, the maximum peak wavelength of fluorescence emission may be referred to as the maximum fluorescence emission peak wavelength (FL-peak).
[0707] [Second Embodiment] (electronic equipment) The electronic device according to this embodiment is equipped with an organic EL element according to one 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, smartphones, tablets, and personal computers. Examples of light-emitting devices include lighting and vehicle lights. The light-emitting device can also be used in a display device, for example, as a backlight for a display device.
[0708] In one embodiment of the electronic device of this embodiment, the display device and light-emitting device are equipped with the organic EL element of the above embodiment. In one embodiment of the electronic device of this embodiment, the display device and light-emitting device preferably have the organic EL element of the above embodiment and a color conversion layer. The display device and light-emitting device preferably have a color filter. The color conversion layer is preferably located between the organic EL element and the color filter. The color conversion layer preferably contains a substance that absorbs light and emits light, and the substance that absorbs light and emits light is preferably a quantum dot. In the light-emitting device, the color conversion layer is preferably arranged so that the light emitted from the organic EL element irradiates the color conversion layer.
[0709] [Variations of the Embodiment] It should be noted that the present invention is not limited to the embodiments described above. Modifications, improvements, etc., that can achieve the objectives of the present invention are included in the present invention. The light-emitting layers included in the first and second light-emitting bands of the organic EL element are not limited to two layers, but may consist of three or more layers, each independently. If an organic EL element includes additional emission bands in addition to the first and second emission bands, the emission layers included in each of these additional emission bands may be not limited to one or two layers, but may consist of three or more stacked emission layers. The multiple emission layers included in each emission band may be of the same emission type or different emission types. Each emission layer may be a fluorescent emission layer or a phosphorescent emission layer that utilizes emission due to electron transitions from a triplet excited state to a direct ground state.
[0710] 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. [Examples]
[0711] The present invention will be described in more detail below with reference to examples. The present invention is not limited to these examples.
[0712] <Compound> The structures of the compounds used as the first or third host material in the manufacture of the organic EL elements in Examples 1-4 and Comparative Examples 1-3 are shown below.
[0713] [ka]
[0714] [ka]
[0715] The structures of the compounds used as the second or fourth host material in the manufacture of the organic EL elements in Examples 1-4 and Comparative Examples 1-3 are shown below.
[0716] [ka]
[0717] The structures of other compounds used in the production of organic EL elements in Examples 1-4 and Comparative Examples 1-3 are shown below.
[0718] [ka]
[0719] [ka]
[0720] [ka]
[0721] [ka]
[0722] [Fabrication of Organic EL Devices (1)] <Example 1> A glass substrate (manufactured by Geomatec Co., Ltd.) with a 25mm x 75mm x 1.1mm thick ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was set to 130 nm.
[0723] (First light-emitting unit) • First hole transport band Next, compound HT1 as a hole transport band material and compound HA as an acceptor material were co-deposited onto the anode using vacuum deposition to form a first hole injection layer with a thickness of 10 nm. The content of compound HT1 in the first hole injection layer was set to 97% by mass, and the content of compound HA was set to 3% by mass. Next, compound HT1 was deposited on the first hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, compound HT2 was deposited on the first hole transport layer to form a first electron barrier layer with a thickness of 10 nm. Thus, in the first stage light-emitting unit (first light-emitting unit), a first hole transport band was formed, including a first hole injection layer, a first hole transport layer, and a first electron barrier layer.
[0724] • First emission band Next, compound BH1-1 as the first host material and compound BD1 as the first luminescent compound were co-deposited onto the first electron barrier layer to form a first luminescent layer with a thickness of 5 nm. The content of compound BH1-1 in the first luminescent layer was set to 98% by mass, and the content of compound BD1 was set to 2% by mass. Next, compound BH2-1, as a second host material, and compound BD1, as a second luminescent compound, were co-deposited onto the first luminescent layer to form a second luminescent layer with a thickness of 20 nm. The content of compound BH2-1 in the second luminescent layer was set to 98% by mass, and the content of compound BD1 was set to 2% by mass. In this way, a first light-emitting band, including a first light-emitting layer and a second light-emitting layer, was formed in the first light-emitting unit.
[0725] • First electron transport band Next, compound ET1 was deposited on the second light-emitting layer to form a first hole barrier layer with a thickness of 10 nm. In this way, a first electron transport band including the first hole barrier layer was formed in the first light-emitting unit.
[0726] (First charge generation band) Next, compound ET2, used as an electron transport band material, and lithium were co-deposited onto the first hole barrier layer to form a first charge generation layer with a thickness of 20 nm. The compound ET2 content in the first charge generation layer was set to 97% by mass, and the lithium content to 3% by mass. Next, compound HT3 as a hole transport band material and compound HA as an acceptor material were co-deposited onto the first charge generation layer to form a second charge generation layer with a thickness of 10 nm. The content of compound HT3 in the second charge generation layer was set to 90% by mass, and the content of compound HA was set to 10% by mass. Thus, a first charge generation band, including a first charge generation layer and a second charge generation layer, was formed between the first light-emitting unit and the second light-emitting unit.
[0727] (Second light-emitting unit) • Second hole transport band Next, compound HT3, used as a hole transport band material, was deposited onto the second charge generation layer to form a second hole transport layer with a thickness of 80 nm. Next, compound HT2, used as a hole transport band material, was deposited onto the second hole transport layer to form a second electron barrier layer with a thickness of 10 nm. Thus, in the second stage light-emitting unit (second light-emitting unit), a second hole transport band including a second hole transport layer and a second electron barrier layer was formed.
[0728] • Second emission band Next, compound BH1-2 as a third host material and compound BD1 as a third luminescent compound were co-deposited onto the second electron barrier layer to form a third luminescent layer with a thickness of 5 nm. The content of compound BH1-2 in the third luminescent layer was set to 98% by mass, and the content of compound BD1 was set to 2% by mass. Next, compound BH2-1, as the fourth host material, and compound BD1, as the fourth luminescent compound, were co-deposited onto the third luminescent layer to form a fourth luminescent layer with a thickness of 20 nm. The content of compound BH2-1 in the fourth luminescent layer was set to 98% by mass, and the content of compound BD1 was set to 2% by mass. Thus, in the second light-emitting unit, a second light-emitting band including the third light-emitting layer and the fourth light-emitting layer was formed.
[0729] • Second electron transport band Next, compound ET1 was deposited on the fourth light-emitting layer to form a second hole barrier layer with a thickness of 10 nm. Next, compound ET3 was deposited on the second hole barrier layer to form a second electron transport layer with a thickness of 20 nm. Next, LiF was deposited on the second electron transport layer to form a second electron injection layer with a thickness of 1 nm. Thus, in the second light-emitting unit, a second electron transport band was formed, including a second hole barrier layer, a second electron transport layer, and a second electron injection layer.
[0730] Then, metallic aluminum was deposited on the second electron injection layer to form a cathode with a thickness of 80 nm. As described above, a bottom-emission type organic EL element according to Example 1 was fabricated. The element configuration of the organic EL element according to Example 1 is schematically shown below.
[0731] ITO(130) / HT1:HA(10,97%:3%) / HT1(80) / HT2(10) / BH1-1:BD1(5,98%:2%) / BH2-1:BD1(20,98%:2%) / ET1(10) / ET2:Li(20,97%:3 %) / HT3:HA(10,90%:10%) / HT3(80) / HT2(10) / BH1-2:BD1(5,98%:2%) / BH2-1:BD1(20,98%:2%) / ET1(10) / ET3(20) / LiF(1) / Al(80)
[0732] In the simplified device configuration described above, the numbers in parentheses indicate the film thickness (in nm). Similarly, the numbers in parentheses, expressed as percentages, indicate the content of the component contained in the corresponding layer (in mass %). For example, the percentage (97%:3%) indicates the content of HT1 and HA in the first hole injection layer (in mass %), the percentage (98%:2%) indicates the content of the host material and luminescent compound in the first, second, third, or fourth light-emitting layer (in mass %), the percentage (97%:3%) indicates the content of ET2 and Li in the first charge generation layer (in mass %), and the percentage (90%:10%) indicates the content of HT3 and HA in the second charge generation layer (in mass %). The same applies to the following examples and comparative examples.
[0733] <Example 2> The organic EL element of Example 2 was fabricated in the same manner as the organic EL element of Example 1, except that the second and fourth host materials were changed from compound BH2-1 to compound BH2-2 as listed in Table 1.
[0734] <Example 3> The organic EL element of Example 3 was fabricated in the same manner as the organic EL element of Example 1, except that the first host material was changed from compound BH1-1 to compound BH1-3 listed in Table 1, and the third host material was changed from compound BH1-2 to compound BH1-4 listed in Table 1.
[0735] <Example 4> The organic EL element of Example 4 was fabricated in the same manner as the organic EL element of Example 1, except that the first host material was changed from compound BH1-1 to compound BH1-B listed in Table 1, and the third host material was changed from compound BH1-2 to compound BH1-4 listed in Table 1.
[0736] <Comparative Example 1> The organic EL element of Comparative Example 1 was manufactured in the same manner as the organic EL element of Example 1, except that the first host material was changed from compound BH1-1 to compound BH1-A listed in Table 1, and the third host material was changed from compound BH1-2 to compound BH1-A listed in Table 1. In other words, in the organic EL element of Comparative Example 1, the first host material and the third host material were the same compound.
[0737] <Comparative Example 2> The organic EL element of Comparative Example 2 was manufactured in the same manner as the organic EL element of Example 1, except that the first host material was changed from compound BH1-1 to compound BH1-B listed in Table 1, and the third host material was changed from compound BH1-2 to compound BH1-B listed in Table 1. In other words, in the organic EL element of Comparative Example 2, the first host material and the third host material were the same compound.
[0738] <Comparative Example 3> The organic EL element of Comparative Example 3 was manufactured in the same manner as in Example 1, except that a second light-emitting layer with a thickness of 25 nm was formed on the first electron barrier layer without forming the first light-emitting layer of the organic EL element of Example 1, and a fourth light-emitting layer with a thickness of 25 nm was formed on the second electron barrier layer without forming the third light-emitting layer.
[0739] <Evaluation of Organic EL Devices> The fabricated organic EL elements were evaluated as follows. The evaluation results are shown in Table 1. The triplet energies T1 of the first, second, third, and fourth host materials and the first, second, third, and fourth luminescent compounds used in the light-emitting layers of each example and comparative example are also shown in Table 1.
[0740] (External quantum efficiency EQE) The current density for the fabricated organic EL element was 10 mA / cm². 2The spectral radiance spectrum was measured when a voltage was applied in such a manner. The spectral radiance spectrum was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming that lambassian emission was performed.
[0741] (Life span LT95) The current density for the fabricated organic EL element was 50 mA / cm². 2 A voltage was applied to achieve the desired result, and the time it took for the brightness to reach 95% of the initial brightness (LT95 (unit: hours)) was measured as the lifespan. Brightness was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.).
[0742] [Table 1]
[0743] As in the organic EL elements of Examples 1 to 4, the first host material in the first light-emitting layer of the first light-emitting unit and the third host material in the third light-emitting layer of the second light-emitting unit are different compounds. Therefore, compared to the organic EL elements of Comparative Examples 1 to 2, where the first host material and the third host material are the same compound, the luminous efficiency and lifespan of the organic EL elements were improved.
[0744] <Evaluation of Compounds> (Measurement of the maximum fluorescence emission peak wavelength (FL-peak)) Compound BD1, 4.9 × 10 -6 Compound BD1 was dissolved in toluene at a concentration of mol / L to prepare a toluene solution. The maximum fluorescence emission peak wavelength when the toluene solution of compound BD1 was excited at 390 nm was measured using a fluorescence spectroscopy instrument. A Hitachi High-Tech Science Corporation F-7000 spectrofluorometer was used as the fluorescence spectroscopy instrument. The peak fluorescence wavelength of compound BD1 was 453 nm.
[0745] (Triplet energy T1) The compound to be measured was dissolved in EPA (diethyl ether:isopentane:ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol / L to obtain a solution, which was then placed in a quartz cell to be used as the measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) of this measurement sample was measured at a low temperature (77 [K]), and a tangent line was drawn to the rising edge of the short-wavelength side of this phosphorescence spectrum. The wavelength value λ at the intersection of this tangent line and the horizontal axis was measured. edge Based on [nm], the energy amount calculated from the following conversion formula (F1) was defined as the triplet energy T1. Note that the triplet energy T1 may have an error of approximately ±0.02 eV depending on the measurement conditions. Conversion formula (F1): T1[eV]=1239.85 / λ edge
[0746] 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 considered the tangent to the rise of the phosphorescence spectrum on the short-wavelength side. Furthermore, maxima with peak intensity less than 15% of the maximum peak intensity of the spectrum are not included in the shortest wavelength maxima mentioned above. Instead, the tangent line drawn at the point closest to the shortest wavelength maxima, where the slope value is at its maximum, is considered the tangent line to the rising edge of the phosphorescence spectrum on the short wavelength side. For phosphorescence measurements, a Hitachi High-Technologies Corporation F-4500 spectrofluorometer was used. [Explanation of Symbols]
[0747] 1: Organic EL element, 3: Anode, 4: Cathode, 8: First charge generation band, 10: First light-emitting unit, 20: Second light-emitting unit, 51: First light-emitting band, 52: Second light-emitting band, 61: First hole transport band, 62: Second hole transport band, 71: First electron transport band, 72: Second electron transport band, 81: First charge generation layer, 82: Second charge generation layer, 511: First light-emitting layer, 512: Second light-emitting layer, 521: Third light-emitting layer, 522: Fourth light-emitting layer.
Claims
1. An organic electroluminescent element, The organic electroluminescent element comprises an anode, a cathode, and two or more light-emitting units disposed between the anode and the cathode. The two or more light-emitting units include at least a first light-emitting unit having a first light-emitting band and a second light-emitting unit having a second light-emitting band. The anode, the first light-emitting unit, the second light-emitting unit, and the cathode are arranged in this order from the anode side toward the cathode side. The first light-emitting band includes a first light-emitting layer containing a first host material and a second light-emitting layer containing a second host material. The first light-emitting layer is positioned closer to the anode than the second light-emitting layer. The aforementioned second light-emitting band includes a third light-emitting layer containing a third host material and a fourth light-emitting layer containing a fourth host material. The third light-emitting layer is positioned closer to the anode than the fourth light-emitting layer. The first light-emitting layer, the second light-emitting layer, the third light-emitting layer, and the fourth light-emitting layer each independently contain a light-emitting compound that exhibits light emission with a maximum peak wavelength of 500 nm or less. The first host material and the third host material are different from each other. Unlike the second host material and the fourth host material, the first host material is The third host material differs from the second host material and the fourth host material, The second host material and the fourth host material are either identical or different from each other. 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 following equation (Equation 1), The triplet energy T of the third host material 1 (H3) and the triplet energy T of the fourth host material 1 (H4) and satisfy the following formula (Equation 2), Organic electroluminescent element. T 1 (H1) > T 1 (H2)…(Number 1) T 1 (H3) > T 1 (H4) …(Number 2)
2. In the organic electroluminescent element according to claim 1, The second host material and the fourth host material are identical to each other. Organic electroluminescent element.
3. In the organic electroluminescent element according to claim 1, The second host material and the fourth host material are different from each other. Organic electroluminescent element.
4. In an organic electroluminescent element according to any one of claims 1 to 3, The second host material and the fourth host material are each independently a compound represented by the following formula (2): Organic electroluminescent element. 【Chemistry 1】 (In the above formula (2), R 201 ~R 208 are each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R) 906 ) (Caution 907 ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by - COOR 802 A base represented by halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, L 201 and L 202 Each of them operates independently. single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, Ar 201 and Ar 202 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted. (In the second host material and the fourth host material, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. R 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 (They are either identical or different to each other.)
5. In an organic electroluminescent element according to any one of claims 1 to 4, The second host material and the fourth host material, or both thereof, are compounds containing one or more deuterium atoms in their molecules. Organic electroluminescent element.
6. In an organic electroluminescent element according to any one of claims 1 to 5, One or both of the second host material and the fourth host material are compounds that do not contain deuterium atoms in their molecules. Organic electroluminescent element.
7. In an organic electroluminescent element according to any one of claims 1 to 6, The second host material and the fourth host material, or both thereof, contain only carbon atoms and hydrogen atoms in their molecules. Organic electroluminescent element.
8. In an organic electroluminescent element according to any one of claims 1 to 7, The second host material and the fourth host material, or both, contain carbon atoms, hydrogen atoms and heteroatoms in their molecules. Organic electroluminescent element.
9. In an organic electroluminescent element according to any one of claims 1 to 8, The second light-emitting layer and the fourth light-emitting layer, or both, further contain a cohost material. The cohost material contained in the second light-emitting layer and the cohost material contained in the fourth light-emitting layer are either identical or different from each other. The second host material differs from the cohost material contained in the second light-emitting layer and the cohost material contained in the fourth light-emitting layer. The fourth host material is different from the cohost material contained in the second light-emitting layer and the cohost material contained in the fourth light-emitting layer. Organic electroluminescent element.
10. In an organic electroluminescent element according to any one of claims 1 to 9, At least one of the first host material and the third host material is a compound selected from the group consisting of a compound represented by the following formula (H11), a compound represented by the formula (H12), a compound represented by the formula (H13), a compound represented by the formula (H14), a compound represented by the formula (H15), and a compound represented by the formula (H16). Organic electroluminescent element. 【Chemistry 2】 (In the above formula (H11), R 101 ~R 110 , and R 111 ~R 120 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by - COOR 802 A base represented by halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, However, R 101 ~R 110 One of them is L 101 The bond position with R is shown, 111 ~R 120 One of them is L 101 It shows the bonding position with, L 101 teeth, single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 24 carbon atoms, or A divalent heterocyclic group having 5 to 24 substituted or unsubstituted ring-forming atoms, mx is 0, 1, 2, 3, 4, or 5. L 101 If there are two or more, then there are two or more L 101 (They are either identical or different to each other.) 【Transformation 3】 (In the above formula (H12), Xa is an oxygen atom, a sulfur atom, C(R) 1201 ) (Caution 1202 ), or Si (R 1203 ) (Caution 1204 ) and R 1201 ~R 1204 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R) 906 ) (Caution 907 ) a base represented by halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, R 121 ~R 130 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 121 ~R 130 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R) 906 ) (Caution 907 ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by - COOR 802 A base represented by halogen atom, Nitro group, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, or The group is represented by the above formula (H121), However, R 121 ~R 130 at least one of which is a group represented by the formula (H121), If there are multiple groups represented by the formula (H121), the multiple groups represented by the formula (H121) may be identical or different from each other. L 12 teeth, single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, ma is 0, 1, 2, or 3. L 12 If there are two or more, then there are two or more L 12 They are either identical or different from one another. Ar 12 This is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. Ar 12 If there are two or more Ar 12 They are either identical or different from one another. In the above formula (H121), * indicates the bonding position. 【Chemistry 4】 (In the above formula (H13), R 131 ~R 134 and R 139 ~R 140 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a substituted or unsubstituted monoring, or They do not bind to each other, R 135 ~R 138 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a substituted or unsubstituted monoring, or They do not bind to each other, Ar 131 Ar 132 , and R that does not form a monoring of the substituted or unsubstituted form. 131 ~R 140 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by - COOR 802 A base represented by halogen atom, Cyano group, Nitro group, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, or The group is represented by the above formula (H131), However, R 131 ~R 140 Ar 131 and Ar 132 At least one of them is a group represented by formula (H131), If there are multiple groups represented by the formula (H131), the multiple groups represented by the formula (H131) may be identical or different from each other. L 13 teeth, single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, Ar 13 teeth, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, MB is 0, 1, 2, 3, 4, or 5. L 13 If there are two or more, then there are two or more L 13 They are either identical or different from one another. Ar 13 If there are two or more Ar 13 They are either identical or different from one another. In formula (H131), the asterisk (*) indicates the bonding position with the benz[a]anthracene ring in formula (H13). 【Transformation 5】 (In the above formula (H14), R 1A and R 1B Each of them operates independently. Substituted or unsubstituted alkyl groups having 1 to 15 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 17 carbon atoms, or These are heterocyclic groups with 5 to 17 substituted or unsubstituted ring-forming atoms. However, R 1A and R 1B At least one of them is a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, R 141 ~R 144 A set of two or more adjacent items and R 145 ~R 148 Any one of the pairs of two or more adjacent items is They combine with each other to form a substituted or unsubstituted monoring, or They bond to each other, forming substituted or unsubstituted fused rings. The group represented by the above formula (H141) is If a substituted or unsubstituted monoring or a substituted or unsubstituted fused ring is formed on ring A, R 142 The carbon atom of ring A that is bonded to, or the carbon atoms constituting the monoring on ring A and the fused ring on ring A, the carbon atom C on ring B. 2 The carbon atom of ring A is bonded to it by a single bond. 1 Bonded to the carbon atom furthest from it, When a substituted or unsubstituted monoring or a substituted or unsubstituted fused ring is not formed on ring A but is formed on ring B, R 142 Bonded to a carbon atom, R is not a group represented by the above formula (H141). 142 R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring. 141 , R 143 , R 144 and R 145 ~R 148 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R) 906 ) (Caution 907 ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by - COOR 802 A base represented by halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 17 carbon atoms, or These are heterocyclic groups with 5 to 17 substituted or unsubstituted ring-forming atoms. In the above formula (H141), Ar 14 This is a substituted or unsubstituted aryl group formed by the fusion of four or more rings, or a substituted or unsubstituted heterocyclic group formed by the fusion of four or more rings. L 14 teeth, single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 17 carbon atoms, or A divalent heterocyclic group having 5 to 17 substituted or unsubstituted ring-forming atoms, mc is 0, 1, or 2. * indicates the bonding position with the atoms constituting the ring in formula (H14) above. However, the compound represented by formula (H14) does not contain three or more substituted or unsubstituted aryl groups formed by the condensation of four or more rings, or substituted or unsubstituted heterocyclic groups formed by the condensation of four or more rings, in the molecule of the compound represented by formula (H14). 【Transformation 6】 (In the above formula (H15), R 150 ~R 159 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by - COOR 802 A base represented by halogen atom, Cyano group, Nitro group, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, or The group is represented by the above formula (H150), However, R 150 ~R 159 At least one of them is a group represented by the formula (H150), If there are multiple groups represented by the formula (H150), the multiple groups represented by the formula (H150) may be identical or different from each other. L 151 teeth, single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, Ar 151 teeth, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, mg is 0, 1, 2, 3, 4, or 5. L 151 If there are two or more, then there are two or more L 151 They are either identical or different from one another. Ar 151 If there are two or more Ar 151 They are either identical or different from one another. In formula (H150), the asterisk (*) indicates the bonding position with the pyrene ring in formula (H15). 【Transformation 7】 (In the above formula (H16), R 160 ~R 169 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 160 ~R 169 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by - COOR 802 A base represented by halogen atom, Cyano group, Nitro group, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, or The group is represented by the above formula (H161), However, the substituents when the substituted or unsubstituted monoring has substituents, the substituents when the substituted or unsubstituted fused ring has substituents, and R 160 ~R 169 At least one of these is a group represented by formula (H161), If there are multiple groups represented by the above formula (H161), the multiple groups represented by the above formula (H161) may be identical or different from each other. L 16 teeth, single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, Ar 16 teeth, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, mf is 0, 1, 2, 3, 4, or 5. L 16 If there are two or more, then there are two or more L 16 They are either identical or different from one another. Ar 16 If there are two or more Ar 16 They are either identical or different from one another. The asterisk (*) in formula (H161) indicates the bonding position with the ring represented by formula (H16). (In the first host material and the third host material, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. R 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 (They are either identical or different to each other.)
11. In the organic electroluminescent element according to claim 10, The first host material and the third host material are each independently a compound selected from the group consisting of the compound represented by formula (H11), the compound represented by formula (H12), the compound represented by formula (H13), the compound represented by formula (H14), the compound represented by formula (H15), and the compound represented by formula (H16). Organic electroluminescent element.
12. In the organic electroluminescent element according to claim 10 or claim 11, One of the first host material and the third host material is a compound represented by formula (H11), and the other of the first host material and the third host material is a compound represented by formula (H13). Organic electroluminescent element.
13. In the organic electroluminescent element according to claim 10 or claim 11, One of the first host material and the third host material is a compound represented by formula (H14) or formula (H15), and the other of the first host material and the third host material is a compound represented by formula (H13). Organic electroluminescent element.
14. In the organic electroluminescent element according to claim 10 or claim 11, One of the first host material and the third host material is a compound represented by formula (H12), and the other of the first host material and the third host material is a compound represented by formula (H13). Organic electroluminescent element.
15. In an organic electroluminescent element according to any one of claims 1 to 14, One or both of the first host material and the third host material are compounds containing one or more deuterium atoms in their molecules. Organic electroluminescent element.
16. In an organic electroluminescent element according to any one of claims 1 to 15, One or both of the first host material and the third host material are compounds that do not contain deuterium atoms in their molecules. Organic electroluminescent element.
17. In an organic electroluminescent element according to any one of claims 1 to 16, Of the luminescent compounds contained in the first luminescent layer, the second luminescent layer, the third luminescent layer, and the fourth luminescent layer, at least one is a luminescent compound that exhibits luminescence with a maximum peak wavelength of 430 nm or more and 480 nm or less. Organic electroluminescent element.
18. In an organic electroluminescent element according to any one of claims 1 to 17, The luminescent compounds contained in the first, second, third, and fourth light-emitting layers are the same compound. Organic electroluminescent element.
19. In an organic electroluminescent element according to any one of claims 1 to 18, At least one of the luminescent compounds contained in the first luminescent layer, the second luminescent layer, the third luminescent layer, and the fourth luminescent layer is a fluorescent compound. Organic electroluminescent element.
20. In an organic electroluminescent element according to any one of claims 1 to 19, The luminescent compounds contained in the first, second, third, and fourth light-emitting layers are all fluorescent compounds. Organic electroluminescent element.
21. In an organic electroluminescent element according to any one of claims 1 to 20, The first light-emitting layer, the second light-emitting layer, the third light-emitting layer, and the fourth light-emitting layer do not contain phosphorescent material. Organic electroluminescent element.
22. In an organic electroluminescent element according to any one of claims 1 to 21, A first charge generation band is included between the first light-emitting unit and the second light-emitting unit. The first charge generation band includes a first charge generation layer and a second charge generation layer located closer to the second light-emitting unit than the first charge generation layer. Organic electroluminescent element.
23. In the organic electroluminescent element according to claim 22, The first light-emitting unit includes a first hole transport band, The second light-emitting unit includes a second hole transport band, The first hole transport band is included between the anode and the first light emission band. The second hole transport band is included between the first charge generation band and the second light emission band. The first hole transport band and the second hole transport band each independently include one or more layers. At least one of the one or more layers included in the first hole transport zone, and at least one of the one or more layers included in the second hole transport zone, each independently contains a monoamine compound. Organic electroluminescent element.
24. In the organic electroluminescent element according to claim 22 or claim 23, The first light-emitting unit described above includes a first electron transport band, The second light-emitting unit includes a second electron transport band, The first electron transport band is included between the first emission band and the first charge generation band. The second electron transport band is included between the second emission band and the cathode. The first electron transport band and the second electron transport band each independently include one or more layers. At least one of the one or more layers included in the first electron transport band, and at least one of the one or more layers included in the second electron transport band, each independently contains an azine compound. Organic electroluminescent element.
25. In an organic electroluminescent element according to any one of claims 1 to 24, The thickness of the first light-emitting layer is smaller than the thickness of the second light-emitting layer. The thickness of the third light-emitting layer is smaller than the thickness of the fourth light-emitting layer. Organic electroluminescent element.
26. In an organic electroluminescent element according to any one of claims 1 to 25, The first light-emitting unit is the first stage light-emitting unit closest to the anode, The aforementioned second light-emitting unit is the second stage light-emitting unit. Organic electroluminescent element.
27. An electronic device equipped with an organic electroluminescent element according to any one of claims 1 to 26.