Organic electroluminescent element and electronic apparatus
A dual emitting layer structure with optimized triplet energy and orientation ratios in OLEDs addresses inefficiencies in luminous efficiency, enhancing performance and efficiency in organic electroluminescence elements.
Patent Information
- Application Number
- JP2022092448
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2022-06-07
- Publication Date
- 2025-09-10
- Estimated Expiration
- Not applicable · inactive patent
AI Technical Summary
Existing organic electroluminescence elements (OLEDs) suffer from inefficiencies in luminous efficiency due to the statistical generation of singlet and triplet excitons, which affect performance metrics such as brightness, emission wavelength, chromaticity, and lifespan.
The use of a dual emitting layer structure with different host materials and emitting compounds, where the triplet energy and orientation ratios are optimized to enhance the recombination of holes and electrons, thereby improving luminous efficiency.
The optimized dual emitting layer structure enhances the luminous efficiency of OLEDs, leading to improved performance and efficiency in organic electroluminescence elements.
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Figure 2025131943000001_ABST
Abstract
Description
[Technical Field]
[0001] The present invention relates to an organic electroluminescence element and an electronic device. [Background technology]
[0002] Organic electroluminescent elements (hereinafter sometimes referred to as "organic EL elements") are used in full-color displays such as those for mobile phones and televisions. When a voltage is applied to an organic EL element, holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. The injected holes and electrons then recombine in the light-emitting layer 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 at a rate of 75%. In order to improve the performance of organic EL elements, for example, Patent Document 1 discloses various studies on compounds used in organic EL elements. The performance of an organic EL element includes, for example, brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan. [Prior art documents] [Patent documents]
[0003] [Patent Document 1] International Publication No. 2021 / 210305 Summary of the Invention [Problem to be solved by the invention]
[0004] An object of the present invention is to provide an organic electroluminescence element with improved performance. Another object of the present invention is to provide an organic electroluminescence element with improved luminous efficiency, and to provide an electronic device equipped with the organic electroluminescence element. [Means for solving the problem]
[0005] According to one aspect of the present invention, there is provided an organic electroluminescence device comprising an anode, a cathode, and an emitting region disposed between the anode and the cathode, the emitting region including a first emitting layer and a second emitting layer, the first emitting layer containing a first host material and a first emitting compound, the second emitting layer containing a second host material and a second emitting compound, the first host material and the second host material being different from each other, the first emitting compound and the second emitting compound being the same or different from each other, and a triplet electron transport molecule of the first host material being a triplet electron transport molecule. The present invention provides an organic electroluminescent element in which the triplet energy T1(H1) of the first light-emitting compound and the triplet energy T1(H2) of the second host material satisfy the relationship of the following mathematical formula (1), the first light-emitting compound exhibits a first orientation (σ1) in a first film containing the first host material and the first light-emitting compound, the second light-emitting compound exhibits a second orientation (σ2) in a second film containing the second host material and the second light-emitting compound, and the ratio of the first orientation (σ1) to the second orientation (σ2) satisfies the relationship of the following mathematical formula (2). T1(H1)>T1(H2) ... (Number 1) σ1 / σ2≧0.9 …(Equation 2)
[0006] According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescence element according to the above-described aspect of the present invention. [Effects of the Invention]
[0007] According to one aspect of the present invention, an organic electroluminescence element with improved performance can be provided. Furthermore, according to another aspect of the present invention, an organic electroluminescence element with improved luminous efficiency can be provided. Furthermore, according to another aspect of the present invention, an electronic device incorporating the organic electroluminescence element can be provided. [Brief explanation of the drawings]
[0008] [Figure 1]1 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to an embodiment of the present invention. [Figure 2] FIG. 2 is a diagram showing a schematic configuration of another example of an organic electroluminescence element according to one embodiment of the present invention. [Figure 3] FIG. 2 is an explanatory diagram illustrating a method for measuring a first orientation and a second orientation. [Figure 4] FIG. 2 is an explanatory diagram illustrating a method for measuring a first orientation and a second orientation. [Figure 5] FIG. 2 is an explanatory diagram illustrating a method for measuring a first orientation and a second orientation. [Figure 6] FIG. 2 is a schematic diagram illustrating an example of an apparatus used in a method for measuring a first orientation and a second orientation. [Figure 7] 1 is a graph showing an example of the angle dependence of p-polarized PL intensity at 465 nm in a PL spectrum. [Figure 8] FIG. 1 is a diagram showing a measurement system for transient EL waveforms. [Figure 9] FIG. 1 is a diagram showing a method for measuring the TTF-derived luminescence intensity ratio, and a graph showing the change over time in the luminescence intensity of an EL element. [Figure 10] FIG. 1 is a diagram showing a method for measuring the TTF-derived luminescence intensity ratio, and is a graph showing the time change of the reciprocal of the square root of the light intensity. DETAILED DESCRIPTION OF THE INVENTION
[0009] [Definition] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.
[0010] In this specification, in a chemical structural formula, a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom is assumed to be bonded to a possible bonding position that is not explicitly marked with a symbol such as "R" or "D" representing a deuterium atom.
[0011] As used herein, the term "number of ring carbon atoms" refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. For example, a 9,9-diphenylfluorenyl group has 13 ring carbon atoms, and a 9,9'-spirobifluorenyl group has 25 ring carbon atoms. Furthermore, when a benzene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Therefore, the number of ring carbon atoms of the benzene ring substituted with an alkyl group is 6. Furthermore, when a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.
[0012] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, or a ring assembly). Atoms that do not constitute the ring (e.g., hydrogen atoms terminating the bonds of atoms constituting the ring) and atoms contained in the substituent when the ring is substituted with a substituent are not included in the number of ring atoms. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms or atoms constituting a substituent bonded to a pyridine ring is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. Furthermore, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring, so the number of ring atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.
[0013] In this specification, the "number of carbon atoms XX to YY" in the expression "substituted or unsubstituted ZZ group having carbon atoms XX to YY" refers to the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.
[0014] In this specification, the "number of atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having XX to YY atoms" refers to the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituent when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.
[0015] In this specification, an unsubstituted ZZ group refers to a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to a case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group". In this specification, "unsubstituted" in the context of a "substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is not replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protist atom, a deuterium atom, or a tritium atom. In this specification, "substituted" in the context of "a substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. Similarly, "substituted" in the context of "a BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced with an AA group.
[0016] "Substituents described herein" The substituents described in this specification will be explained below.
[0017] The "unsubstituted aryl group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30 ring carbon atoms, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30 ring atoms, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification. The "unsubstituted alkyl group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification. Unless otherwise specified in this specification, the "unsubstituted alkenyl group" described in this specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms. Unless otherwise specified in this specification, the "unsubstituted alkynyl group" described in this specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms. The "unsubstituted cycloalkyl group" described in this specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted arylene group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30 ring carbon atoms, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted divalent heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30 ring atoms, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification. The "unsubstituted alkylene group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.
[0018] "Substituted or unsubstituted aryl group" Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B). (Here, the term "unsubstituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and the term "substituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" simply refers to both an "unsubstituted aryl group" and a "substituted aryl group." A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent. Examples of the "substituted aryl group" include groups in which one or more hydrogen atoms of the "unsubstituted aryl group" are replaced with a substituent, and examples of the substituted aryl group in the specific example group G1A below. The examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed here are merely examples, and the "substituted aryl group" described in this specification also includes groups in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group" in the specific example group G1B below is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted aryl group" in the specific example group G1B below is further replaced with a substituent.
[0019] Unsubstituted aryl groups (specific example group G1A): phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, benzanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, chrysenyl group, benzochrysenyl group, a triphenylenyl group, benzotriphenylenyl group, tetracenyl group, pentacenyl group, fluorenyl groups, 9,9'-spirobifluorenyl group, benzofluorenyl groups, dibenzofluorenyl groups, fluoranthenyl group, benzofluoranthenyl group, A perylenyl group, or a monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).
[0020] [ka]
[0021] [ka]
[0022] Substituted aryl groups (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, cyanophenyl groups, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl groups and monovalent groups derived from the ring structures represented by the general formulae (TEMP-1) to (TEMP-15) above, in which one or more hydrogen atoms are replaced with substituents.
[0023] "Substituted or unsubstituted heterocyclic group" The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom among the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom. The "heterocyclic groups" described herein are either monocyclic or fused ring groups. The "heterocyclic group" described herein may be an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group," and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group.") In this specification, the term "heterocyclic group" simply includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group." A "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with a substituent. Specific examples of the "substituted heterocyclic group" include the groups in which a hydrogen atom of the "unsubstituted heterocyclic group" in the specific example group G2A below is replaced, and the examples of the substituted heterocyclic group in the specific example group G2B below are also included. The examples of the "unsubstituted heterocyclic group" and the "substituted heterocyclic group" listed here are merely examples, and the "substituted heterocyclic group" described in this specification also includes groups in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic group" in the specific example group G2B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted heterocyclic group" in the specific example group G2B is further replaced with a substituent.
[0024] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).
[0025] Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4).
[0026] Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): pyrrolyl group, imidazolyl group, pyrazolyl group, a triazolyl group, tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, isothiazolyl group, a thiadiazolyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, a triazinyl group, Indolyl groups, isoindolyl groups, an indolizinyl group, a quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, a quinazolinyl group, quinoxalinyl group, benzimidazolyl group, an indazolyl group, a phenanthrolinyl group, a phenanthridinyl group, acridinyl group, phenazinyl group, a carbazolyl group, a benzocarbazolyl group, morpholino group, phenoxazinyl group, a phenothiazinyl group, Azacarbazolyl group and diazacarbazolyl group.
[0027] Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl groups, benzoisoxazolyl group, phenoxazinyl group, morpholino group, a dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, Azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.
[0028] Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): a thienyl group, a thiazolyl group, isothiazolyl group, a thiadiazolyl group, Benzothiophenyl group (benzothienyl group), isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), naphthobenzothiophenyl group (naphthobenzothienyl group), benzothiazolyl group, benzoisothiazolyl group, a phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), diazadibenzothiophenyl group (diazadibenzothienyl group), Azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).
[0029] Monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4):
[0030] [ka]
[0031] [ka]
[0032] In the general formulae (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2. A and Y A At least one of is an oxygen atom, a sulfur atom, or NH. In the general formulae (TEMP-16) to (TEMP-33), X A and Y A When at least one of is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from NH or CH2.
[0033] Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): a (9-phenyl)carbazolyl group, a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a (9-naphthyl)carbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, methylbenzimidazolyl group, ethylbenzimidazolyl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, a phenylquinazolinyl group, and a biphenylylquinazolinyl group.
[0034] Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, t-Butyldibenzofuranyl group, and the monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].
[0035] Substituted heterocyclic groups containing sulfur atoms (specific example group G2B3): phenyldibenzothiophenyl group, methyldibenzothiophenyl group, t-Butyldibenzothiophenyl group, and the monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].
[0036] Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the above general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4):
[0037] The "one or more hydrogen atoms of the monovalent heterocyclic group" refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, X A and Y A a hydrogen atom bonded to a nitrogen atom when at least one of A and Y A or more hydrogen atoms selected from the hydrogen atoms of a methylene group when one of the groups is CH2.
[0038] "Substituted or unsubstituted alkyl groups" Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described herein include the following unsubstituted alkyl group (specific example group G3A) and substituted alkyl group (specific example group G3B). (Here, the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereinafter, when simply referring to an "alkyl group," both an "unsubstituted alkyl group" and a "substituted alkyl group" are included. The term "substituted alkyl group" refers to an "unsubstituted alkyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted alkyl group" include the following "unsubstituted alkyl group" (specific example group G3A) in which one or more hydrogen atoms have been replaced with a substituent, and the examples of the substituted alkyl group (specific example group G3B). In this specification, the alkyl group in the "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the "unsubstituted alkyl group" includes a linear "unsubstituted alkyl group" and a branched "unsubstituted alkyl group." Note that the examples of the "unsubstituted alkyl group" and the "substituted alkyl group" listed here are merely examples, and the "substituted alkyl group" described in this specification also includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" in specific example group G3B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkyl group" in specific example group G3B is further replaced with a substituent.
[0039] Unsubstituted alkyl groups (specific example group G3A): methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group and t-butyl group.
[0040] Substituted alkyl groups (specific example group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group and trifluoromethyl group.
[0041] "Substituted or unsubstituted alkenyl group" Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described herein include the following unsubstituted alkenyl group (specific example group G4A) and substituted alkenyl group (specific example group G4B). (Here, the term "unsubstituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and the term "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply includes both an "unsubstituted alkenyl group" and a "substituted alkenyl group." A "substituted alkenyl group" refers to an "unsubstituted alkenyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl groups" (specific example group G4A) having a substituent, and the examples of substituted alkenyl groups (specific example group G4B). The examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed here are merely examples, and the "substituted alkenyl group" described in this specification also includes groups in the "substituted alkenyl groups" of specific example group G4B in which a hydrogen atom of the alkenyl group itself has been further replaced with a substituent, and groups in the "substituted alkenyl groups" of specific example group G4B in which a hydrogen atom of a substituent has been further replaced with a substituent.
[0042] Unsubstituted alkenyl groups (specific example group G4A): vinyl groups, Allyl groups, a 1-butenyl group, 2-butenyl group and 3-butenyl group.
[0043] Substituted alkenyl groups (specific example group G4B): 1,3-butadienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group and 1,2-dimethylallyl group.
[0044] "Substituted or unsubstituted alkynyl group" Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in this specification include the following unsubstituted alkynyl groups (specific example group G5A). (Here, the unsubstituted alkynyl group refers to a case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, when simply referring to an "alkynyl group," it includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group." A "substituted alkynyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced with substituents. Specific examples of the "substituted alkynyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl group" (specific example group G5A) are replaced with substituents, etc.
[0045] Unsubstituted alkynyl groups (specific example group G5A): Ethynyl group.
[0046] "Substituted or unsubstituted cycloalkyl groups" Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described herein include the following unsubstituted cycloalkyl group (specific example group G6A) and substituted cycloalkyl group (specific example group G6B). (Here, the unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group," and the substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group.") In this specification, when the term "cycloalkyl group" is simply used, it includes both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group." A "substituted cycloalkyl group" refers to an "unsubstituted cycloalkyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (specific example group G6A) in which one or more hydrogen atoms have been replaced with a substituent, and the examples of the substituted cycloalkyl group (specific example group G6B). The examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed here are merely examples, and the "substituted cycloalkyl group" described in this specification also includes a group in the "substituted cycloalkyl group" of specific example group G6B in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself have been replaced with a substituent, and a group in the "substituted cycloalkyl group" of specific example group G6B in which a hydrogen atom of a substituent has been further replaced with a substituent.
[0047] Unsubstituted cycloalkyl groups (specific example group G6A): a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group and 2-norbornyl group.
[0048] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.
[0049] -Si(R 901 )(R 902 )(R 903 ) a group represented by -Si(R) 901 )(R 902 )(R 903 Specific examples (specific example group G7) of the group represented by -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6. The multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other. The multiple G2s in -Si(G1)(G2)(G2) are the same as or different from each other. The multiple G1s in —Si(G1)(G1)(G2) are the same as or different from each other. The multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other. The multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other. The multiple G6s in -Si(G6)(G6)(G6) are the same as or different from each other.
[0050] -O-(R 904 ) a group represented by As described herein, —O—(R 904 Specific examples (specific example group G8) of the group represented by -O(G1), -O(G2), -O(G3) and -O(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.
[0051] -S-(R 905 ) a group represented by -S-(R 905 Specific examples (specific example group G9) of the group represented by -S(G1), -S(G2), -S(G3) and -S(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.
[0052] -N(R 906 )(R 907 ) a group represented by -N(R 906 )(R 907 Specific examples (specific example group G10) of the group represented by -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3) and -N(G6)(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6. -The multiple G1s in N(G1)(G1) are the same as or different from each other. The multiple G2's in -N(G2)(G2) are the same as or different from each other. -The multiple G3s in N(G3)(G3) are the same as or different from each other. The multiple G6s in -N(G6)(G6) are the same as or different from each other.
[0053] "Halogen atoms" Specific examples (specific example group G11) of the "halogen atom" described in this specification include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
[0054] "Substituted or unsubstituted fluoroalkyl groups" The term "substituted or unsubstituted fluoroalkyl group" as used herein refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). Unless otherwise specified herein, the number of carbon atoms in an "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The term "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. The term "substituted fluoroalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in a "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in a "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include the examples of the above-mentioned "alkyl group" (specific example group G3) in which one or more hydrogen atoms are replaced with a fluorine atom.
[0055] "Substituted or unsubstituted haloalkyl groups" The term "substituted or unsubstituted haloalkyl group" as used herein refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The number of carbon atoms in an "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. The term "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms in a "haloalkyl group" are replaced with a substituent. The term "substituted haloalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom in the alkyl chain in a "substituted haloalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in a "substituted haloalkyl group" are further replaced with a substituent. Specific examples of "unsubstituted haloalkyl groups" include the examples of the above-mentioned "alkyl groups" (specific example group G3) in which one or more hydrogen atoms are replaced with halogen atoms. Haloalkyl groups are sometimes referred to as halogenated alkyl groups.
[0056] "Substituted or unsubstituted alkoxy group" A specific example of the "substituted or unsubstituted alkoxy group" described herein is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified herein, the "unsubstituted alkoxy group" has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms.
[0057] "Substituted or unsubstituted alkylthio group" A specific example of the "substituted or unsubstituted alkylthio group" described herein is a group represented by -S(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified herein, the "unsubstituted alkylthio group" has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms.
[0058] "Substituted or unsubstituted aryloxy group" A specific example of the "substituted or unsubstituted aryloxy group" described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
[0059] "Substituted or unsubstituted arylthio group" A specific example of the "substituted or unsubstituted arylthio group" described in this specification is a group represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
[0060] "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described herein is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) may be the same or different. 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 group" A specific example of the "substituted or unsubstituted aralkyl group" described herein is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. Thus, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one embodiment of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group," and the number of carbon atoms in the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified herein. Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl groups.
[0062] Unless otherwise specified in the present specification, the substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, or the like.
[0063] Unless otherwise specified in the present specification, the substituted or unsubstituted heterocyclic group described herein is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an aza Examples include a dibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group (a (9-phenyl)carbazol-1-yl group, a (9-phenyl)carbazol-2-yl group, a (9-phenyl)carbazol-3-yl group, or a (9-phenyl)carbazol-4-yl group), a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, and a phenyldibenzothiophenyl group.
[0064] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.
[0065] [ka]
[0066] In this specification, unless otherwise specified in this specification, a (9-phenyl)carbazolyl group specifically means any of the following groups:
[0067] [ka]
[0068] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.
[0069] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.
[0070] [ka]
[0071] In the general formulae (TEMP-34) to (TEMP-41), * represents a bonding position.
[0072] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, and the like.
[0073] "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group". Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1.
[0074] "Substituted or unsubstituted divalent heterocyclic group" Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom on the heterocycle from the above-mentioned "substituted or unsubstituted heterocyclic group". Specific examples (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group" include divalent groups derived by removing one hydrogen atom on the heterocycle from the "substituted or unsubstituted heterocyclic group" described in specific example group G2.
[0075] "Substituted or unsubstituted alkylene group" Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group." Specific examples of the "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3.
[0076] Unless otherwise specified in the present specification, the substituted or unsubstituted arylene group described in the present specification is preferably any one of the groups represented by the following general formulae (TEMP-42) to (TEMP-68).
[0077] [ka]
[0078] [ka]
[0079] In the general formulae (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-42) to (TEMP-52), * represents a bonding position.
[0080] [ka]
[0081] In the general formulae (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent. Equations Q9 and Q 10 may be bonded to each other via a single bond to form a ring. In the general formulae (TEMP-53) to (TEMP-62), * represents a bonding position.
[0082] [ka]
[0083] In the general formulae (TEMP-63) to (TEMP-68), Q1 to Q8 each independently represent a hydrogen atom or a substituent. In the general formulae (TEMP-63) to (TEMP-68), * represents a bonding position.
[0084] Unless otherwise specified in the present specification, the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the groups represented by the following general formulae (TEMP-69) to (TEMP-102).
[0085] [ka]
[0086] [ka]
[0087] [ka]
[0088] In the general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 each independently represent a hydrogen atom or a substituent.
[0089] [ka]
[0090] [ka]
[0091] [ka]
[0092] [ka]
[0093] In the general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 each independently represent a hydrogen atom or a substituent.
[0094] The above is the explanation of "substituents described in this specification."
[0095] - "When bonded to form a ring" In this specification, the phrase "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted monocycle, bond with each other to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted monocycle", the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted fused ring", or the case where "one or more pairs of adjacent groups do not bond with each other". In this specification, the cases where "one or more groups of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocyclic ring" and "one or more groups of two or more adjacent groups bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "a case where they bond to form a ring") will be explained below. The case of an anthracene compound represented by the following general formula (TEMP-103), in which the main skeleton is an anthracene ring, will be explained as an example.
[0096] [ka]
[0097] For example, R921 ~R 930 In the case where "one or more pairs of adjacent two or more groups are bonded to each other to form a ring," one pair of adjacent two groups is R 921 and R 922 Paired with R 922 and R 923 Paired with R 923 and R 924 Paired with R 924 and R 930 Paired with R 930 and R 925 Paired with R 925 and R 926 Paired with R 926 and R 927 Paired with R 927 and R 928 Paired with R 928 and R 929 Pairs with and R 929 and R 921 It is paired with.
[0098] The above "one or more pairs" means that two or more pairs of adjacent two or more groups may simultaneously form a ring. For example, R 921 and R 922 and are bonded to each other to form ring Q A At the same time, R 925 and R 926 and are bonded to each other to form ring Q B When the anthracene compound represented by the general formula (TEMP-103) is formed, the anthracene compound represented by the general formula (TEMP-104) is represented by the following general formula (TEMP-104).
[0099] [ka]
[0100] When a "set of two or more adjacent units" forms a ring, it does not only mean that a set of two adjacent units is bonded, as in the previous example, but also that a set of three or more adjacent units is bonded. For example, R 921 and R 922 and are bonded to each other to form ring Q A and R 922 and R923 and are bonded to each other to form ring Q C and form three adjacent (R 921 , R 922 and R 923 In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105): A and Ring Q C is R 922 Share.
[0101] [ka]
[0102] The "monocyclic ring" or "fused ring" formed may be a saturated ring or an unsaturated ring as the structure of only the ring formed. Even when "one pair of adjacent two" forms a "monocyclic ring" or a "fused ring", the "monocyclic ring" or the "fused ring" may form a saturated ring or an unsaturated ring. For example, in the case of the ring Q formed in the general formula (TEMP-104), A and Ring Q B are "monocyclic rings" or "fused rings", respectively. A , and ring Q C is a "fused ring". A and Tamaki Q C That is, Tamaki Q A and Tamaki Q C The ring Q in the general formula (TMEP-104) is fused to form a fused ring. A If is a benzene ring, then ring Q A The ring Q in the general formula (TMEP-104) is a monocyclic ring. A If is a naphthalene ring, then ring Q A is a fused ring.
[0103] The term "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The term "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of the aromatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G1 are terminated with a hydrogen atom. Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in the specific example group G2 are terminated with a hydrogen atom. Specific examples of the aliphatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom. The term "forming a ring" means that a ring is formed only with a plurality of atoms of the main skeleton, or with a plurality of atoms of the main skeleton and one or more optional elements. For example, R 921 and R 922 and are bonded to form a ring Q A is R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 It means a ring formed by the carbon atom of the anthracene skeleton to which R is bonded and one or more arbitrary elements. 921 and R 922 Todekan Q A In the case where R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 When a monocyclic unsaturated ring is formed with the carbon atom of the anthracene skeleton to which R is bonded and four carbon atoms, 921 and R 922 The ring formed by
[0104] Here, unless otherwise specified in this specification, the "arbitrary element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur. In the arbitrary element (for example, in the case of carbon or nitrogen), the bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below. When an arbitrary element other than carbon is included, the formed ring is a heterocycle. Unless otherwise specified in this specification, the "one or more arbitrary elements" constituting the monocyclic or fused ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less. Unless otherwise specified in this specification, of the "monocyclic ring" and the "fused ring", the "monocyclic ring" is preferred. Unless otherwise specified in this specification, of the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred. Unless otherwise specified herein, a "monocyclic ring" is preferably a benzene ring. Unless otherwise specified herein, the "unsaturated ring" is preferably a benzene ring. When "one or more pairs of adjacent two or more groups" "combine with each other to form a substituted or unsubstituted monocyclic ring" or "combine with each other to form a substituted or unsubstituted fused ring," unless otherwise specified in this specification, preferably, one or more pairs of adjacent two or more groups combine with each other to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.
[0105] When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents described in this specification." When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents described in this specification." The above is an explanation of the case where "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring" ("when bonded to form a ring").
[0106] Substituents in "substituted or unsubstituted" In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituent" in the present specification) includes, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms; an unsubstituted alkenyl group having 2 to 50 carbon atoms; an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms; -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring carbon atoms and an unsubstituted heterocyclic group having 5 to 50 ring atoms, where R 901 ~R 907 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R 901 If there are two or more, there are two or more R 901 are identical to or different from each other, R 902 If there are two or more, there are two or more R 902 are identical to or different from each other, R 903 If there are two or more, there are two or more R 903are identical to or different from each other, R 904 If there are two or more, there are two or more R 904 are identical to or different from each other, R 905 If there are two or more, there are two or more R 905 are identical to or different from each other, R 906 If there are two or more, there are two or more R 906 are identical to or different from each other, R 907 If there are two or more, there are two or more R 907 are the same or different from each other.
[0107] In one embodiment, the substituents in the "substituted or unsubstituted" are: an alkyl group having 1 to 50 carbon atoms; The group is selected from the group consisting of aryl groups having 6 to 50 ring carbon atoms and heterocyclic groups having 5 to 50 ring atoms.
[0108] In one embodiment, the substituents in the "substituted or unsubstituted" are: an alkyl group having 1 to 18 carbon atoms; The group is selected from the group consisting of aryl groups having 6 to 18 ring carbon atoms and heterocyclic groups having 5 to 18 ring atoms.
[0109] Specific examples of each group of the above optional substituents are the specific examples of the substituents described above in the section "Substituents described in this specification."
[0110] Unless otherwise specified in this specification, any adjacent substituents may be bonded to each other to form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring. Unless otherwise specified in this specification, any optional substituent may further have a substituent. The substituent that the optional substituent further has is the same as the optional substituent described above.
[0111] In this specification, a numerical range expressed using "AA to BB" means a range that includes the number AA written before "AA to BB" as the lower limit and the number BB written after "AA to BB" as the upper limit.
[0112] First Embodiment (organic electroluminescence element) The organic electroluminescent device according to this embodiment has an anode, a cathode, and a light-emitting region disposed between the anode and the cathode. The light-emitting region includes a first light-emitting layer and a second light-emitting layer. The first light-emitting layer contains a first host material and a first light-emitting compound. The second light-emitting layer contains a second host material and a second light-emitting compound. The first host material and the second host material are different from each other. The first light-emitting compound and the second light-emitting compound are the same as or different from each other. The first host material and the second light-emitting compound are 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 relationship of the following mathematical formula (Mathematical Formula 1), the first luminescent compound exhibits a first orientation (σ1) in a first film containing the first host material and the first luminescent compound, the second luminescent compound exhibits a second orientation (σ2) in a second film containing the second host material and the second luminescent compound, and the ratio of the first orientation (σ1) to the second orientation (σ2) satisfies the relationship of the following mathematical formula (Mathematical Formula 2). T1(H1)>T1(H2) ... (Number 1) σ1 / σ2≧0.9 …(Equation 2)
[0113] According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescence element according to the above-described aspect of the present invention.
[0114] According to this embodiment, it is possible to provide an organic electroluminescence element with improved luminous efficiency. Triplet-Triplet-Annhilation (sometimes referred to as TTA) has been known as a technique for improving the luminous efficiency of organic electroluminescence devices. TTA is a mechanism in which triplet excitons collide with other triplet excitons to generate singlet excitons. The TTA mechanism is also sometimes referred to as the TTF (Triplet-Triplet Fusion) mechanism.
[0115] The TTF phenomenon will be explained. Holes injected from the anode and electrons injected from the cathode recombine in the light-emitting layer to generate excitons. As has been conventionally known, the spin state of these excitons is 25% singlet excitons and 75% triplet excitons. In conventional fluorescent elements, 25% of the singlet excitons emit light when they relax to the ground state, but the remaining 75% of the triplet excitons return to the ground state through a thermal deactivation process without emitting light. Therefore, the theoretical limit of the internal quantum efficiency of conventional fluorescent elements was said to be 25%. On the other hand, the behavior of triplet excitons generated inside organic materials has been theoretically investigated. According to S.M. Bachilo et al. (J.Phys.Chem.A,104,7711(2000)), assuming that higher-order excitons such as quintets immediately return to triplets, triplet excitons (hereinafter referred to as triplet excitons) 3 A * When the density of triplet excitons (hereinafter referred to as triplet excitons) increases, triplet excitons collide with each other, causing the reaction shown in the following formula: 1 A represents the ground state, 1 A * represents the lowest excited singlet exciton. 3 A * + 3 A * →(4 / 9) 1 A+(1 / 9) 1 A * +(13 / 9) 3 A * That is, 5 3 A *→4 1 A+1A * It is predicted that 1 / 5, or 20%, of the 75% of triplet excitons initially generated will convert to singlet excitons. Therefore, the singlet excitons contributing to light are 40%, calculated by adding 75% × (1 / 5) = 15% to the initially generated 25%. In this case, the TTF ratio (TTF ratio) of the total luminescence intensity is 15 / 40, or 37.5%. Furthermore, if we assume that singlet excitons are generated by collisions between the initially generated 75% triplet excitons (i.e., one singlet exciton is generated from two triplet excitons), then an extremely high internal quantum efficiency of 62.5% is obtained by adding 75% × (1 / 2) = 37.5% to the initially generated 25% singlet excitons. In this case, the TTF ratio is 37.5 / 62.5 = 60%.
[0116] According to the organic electroluminescent device of this embodiment, triplet excitons generated by recombination of holes and electrons in the first light-emitting layer are thought to be less likely to be quenched at the interface between the first light-emitting layer and the organic layer, even if excess carriers are present at the interface between the first light-emitting layer and the organic layer that is in direct contact with the first light-emitting layer. For example, when the recombination region is locally present at the interface between the first light-emitting layer and the hole transport layer or the electron blocking layer, quenching by excess electrons is thought to be possible. On the other hand, when the recombination region is locally present at the interface between the first light-emitting layer and the electron transport layer or the hole blocking layer, quenching by excess holes is thought to be possible. The organic electroluminescent device according to this embodiment 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, and 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 above-described mathematical formula (Mathematical Formula 1). By providing the first and second light-emitting layers so as to satisfy the relationship of the above mathematical formula (Mathematical Formula 1), triplet excitons generated in the first light-emitting layer can migrate to the second light-emitting layer without being quenched by excess carriers, and reverse migration from the second light-emitting layer to the first light-emitting layer can be suppressed. As a result, the TTF mechanism is exerted in the second light-emitting layer, singlet excitons are efficiently generated, and luminous efficiency is improved. In this way, the organic electroluminescent device has 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 transferred from the first light-emitting layer, as distinct regions. By using a compound having a smaller triplet energy than the first host material in the first light-emitting layer as the second host material in the second light-emitting layer, and by creating a difference in triplet energy, the luminous efficiency is improved.
[0117] In the organic EL device according to 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 of the following mathematical formula (Mathematical Formula 5). T1(H1)-T1(H2)>0.03eV …(Math 1A)
[0118] In addition, an organic electroluminescent device having a light-emitting region in which multiple light-emitting layers are stacked emits light that is the sum of two light-emitting components: a prompt light-emitting component and a light-emitting component due to the TTF mechanism. The organic electroluminescent device has a light-emitting region including a first light-emitting layer containing a first host material and a first light-emitting compound, and a second light-emitting layer containing a second host material and a second light-emitting compound. In the first light-emitting layer, holes and electrons recombine, and in the second light-emitting layer, the TTF mechanism occurs. In conventional organic electroluminescent devices, the TTF mechanism is exerted in the second light-emitting layer, resulting in efficient generation of singlet excitons and improved luminous efficiency. However, the light extraction efficiency of the promptly emitted light component is low in the first light-emitting layer, and therefore the effect of improving the luminous efficiency of the organic electroluminescent device as a whole is low.
[0119] In the study of the present invention, it was found that in the organic electroluminescent device, the orientation of the light-emitting compound contained in the first light-emitting layer tends to be lower than the orientation of the light-emitting compound contained in the second light-emitting layer. When the light-emitting region is in an ideal state, the proportion of the promptly emitting component is 62.5%, and the proportion of the light-emitting component due to the TTF mechanism is 37.5%. Therefore, the orientation of the light-emitting compound contained in the first light-emitting layer has a significant impact on the luminous efficiency of the entire organic electroluminescent device.
[0120] According to the organic electroluminescent element of this embodiment, the orientation (first orientation (σ1)) of the first light-emitting compound in the first film containing a first host material and a first light-emitting compound and the orientation (second orientation (σ2)) of the second light-emitting compound in the second film containing a second host material and a second light-emitting compound are easily maintained at the same level. This makes it possible to extract more of the promptly emitting component of light in the stacking direction of the first light-emitting layer, thereby suppressing a decrease in the light extraction efficiency of the promptly emitting component in the first light-emitting layer and further improving the luminous efficiency of the organic electroluminescent element as a whole.
[0121] (First orientation and second orientation) In the organic electroluminescent device according to this embodiment, the ratio (σ1 / σ2) of the first alignment (σ1) to the second alignment (σ2) is preferably 0.91 or more, more preferably 0.94 or more, and even more preferably 0.97 or more. The ratio (σ1 / σ2) of the first alignment (σ1) to the second alignment (σ2) may exceed 1. In the organic electroluminescent device according to this embodiment, when the first light-emitting layer and the second light-emitting layer contain the same light-emitting compound, it is preferable to combine them so that the orientation of the first light-emitting compound in the first film made of the components of the first light-emitting layer and the orientation of the second light-emitting compound in the second film made of the components of the second light-emitting layer are similar to each other. In this regard, it is preferable that the ratio (σ1 / σ2) of the first orientation (σ1) to the second orientation (σ2) is close to 1. As a result, the luminous efficiency of the organic electroluminescent device as a whole is further improved.
[0122] In the organic electroluminescent device according to this embodiment, the first alignment (σ1) is preferably 0.80 or more, more preferably 0.82 or more, even more preferably 0.85 or more, and even more preferably 0.90 or more.
[0123] In the organic electroluminescent device according to this embodiment, the second alignment property (σ2) is preferably 0.90 or more, more preferably 0.91 or more, and even more preferably 0.92 or more.
[0124] (Method of measuring first orientation and second orientation) The method for calculating the first orientation (σ1) and the second orientation (σ2) from the angle-resolved PL is as follows.
[0125] As shown in Figure 3, the refractive index within the substrate is n s、 The refractive index in the organic film is n0. When light generated in the organic film is incident on the interface between the organic film and the substrate at an angle θ0, reflected light is generated in the organic film at an angle θ0, and transmitted light is generated at an angle θ s The electric field of the p-polarized incident light is expressed as E ip , magnetic flux density B ip Similarly, the electric field of the reflected light is defined as E rp , magnetic flux density B rp , the electric field of the transmitted light is Etp , magnetic flux density B tp From the boundary conditions of the electromagnetic wave, the following formulas (F1) and (F2) hold.
[0126]
number
[0127] The electric field E and magnetic flux density B are expressed by the following formula (F2A) using the speed of light c and the refractive index n in the medium. Substituting the following formula (F2A) into the above formula (F2) and rearranging, we obtain the following formula (F3).
[0128]
number
[0129]
number
[0130] From the formula (F1) and the formula (F3), E tp By eliminating and rearranging, the amplitude reflection coefficient of p-polarized light r p is expressed by the following formula (F4): Similarly, the amplitude transmission coefficient t p is expressed by the following formula (F5).
[0131]
number
[0132] When light propagating from different positions overlaps, optical interference occurs due to the superposition of waves. This optical interference can also be observed in thin films formed on substrates, and the change in amplitude is determined by the phase shift. If the distance from point A to point B in Figure 4 is defined as AB- (the "-" after "B" is originally written above "AB" as shown in formula (F6) below. Note that BC-, AD-, and AC- in formulas (F6) to (F8) also have the same meaning as AB-), then when the wavelength of the propagating light is λ and the thickness of the organic film is d, the phase change α is expressed by formula (F6) below.
[0133]
number
[0134] By substituting the following formulas (F7) and (F8) into the formula (F6) and rearranging the formula, the phase change α can be expressed by formula (F9).
[0135]
number
[0136]
number
[0137] The phase change α is the phase change when the light is reflected back and forth, so the phase film thickness β is expressed by the following equation (F10):
[0138]
number
[0139] In the case of actual EL emission, the light-emitting compound in the organic film emits light, so the state shown in Figure 5 is assumed. Of the amplitude reflection coefficients of p-polarized light mentioned above, the reflection at the interface between the organic film and the substrate is r pos and the reflection at the interface between the organic film and air is defined as r poaSimilarly, the transmission and reflection coefficient of p-polarized light is defined as t pos When reflected at the interface between the organic film and air, t poa When a single luminescent compound is located at a position where the distance to the substrate interface is d1 and the distance to the air interface is d2, the electric field E of p-polarized light in the direction perpendicular to the substrate side is py is expressed by the following formula (F11).
[0140]
number
[0141] The PL intensity of p-polarized light can be calculated using the following formula (F12).
[0142]
number
[0143] Based on the above-mentioned principle, the angle dependence of the intensity of p-polarized light can be calculated by simulation by defining the refractive index of the layer, the thickness of the organic film, and the orientation angle of the light-emitting compound. In this embodiment, the degree of orientation of the luminescent compound can be calculated by comparing the simulation results obtained using optical simulation software Setfos 5.0 (manufactured by Fluxim AG) with experimental values.
[0144] (|λ1-λ2| and |FWHM1-FWHM2|) In the organic electroluminescence element according to this embodiment, it is preferable that the maximum peak wavelength λ1 and half width FWHM1 of the PL spectrum of the first film, and the maximum peak wavelength λ2 and half width FWHM2 of the PL spectrum of the second film satisfy the following mathematical expressions (Mathematical Expression 20) and (Mathematical Expression 30). |λ1-λ2| ≦ 3 nm … (Equation 20) |FWHM1-FWHM2| ≦ 2 nm … (Number 30)
[0145] By combining the first film made of the components of the first light-emitting layer and the second film made of the components of the second light-emitting layer in a way that minimizes the change (difference) in the PL spectrum, the loss when light is extracted from the upper electrode (cathode) or the lower electrode (anode) is reduced, which is thought to result in improved luminous efficiency.
[0146] In the organic EL element according to this embodiment, the maximum peak wavelength λ1 of the PL spectrum of the first film and the maximum peak wavelength λ2 of the PL spectrum of the second film preferably satisfy the following formula (Formula 20A), and more preferably satisfy the following formula (Formula 20B): |λ1-λ2| ≦ 2 nm … (several tens of amps) |λ1-λ2| ≦ 1 nm … (number 20B)
[0147] In the organic EL element according to the first embodiment, it is preferable that the full width at half maximum FWHM1 of the PL spectrum of the first film and the full width at half maximum FWHM2 of the PL spectrum of the second film satisfy the following mathematical formula (Mathematical Formula 30A). |FWHM1-FWHM2| ≦ 1 nm … (several tens of Å)
[0148] The maximum peak wavelength λ1 and half width FWHM1 of the PL spectrum of the first film, and the maximum peak wavelength λ2 and half width FWHM2 of the PL spectrum of the second film can be measured by the following method. First, a first film measurement sample is prepared by the following method so as to have the same structure as the first light-emitting layer. A second film measurement sample is prepared by the following method so as to have the same structure as the second light-emitting layer. "Having the same composition as the first emitting layer" means that the first film is made of the same materials as the first emitting layer. Specifically, when the first emitting layer is made of a first host material and a first emitting compound, the ratio (by mass) of the first emitting compound to the first host material contained in the first emitting layer (first emitting compound / first host material) is the same as the ratio (by mass) of the first emitting compound to the first host material contained in the first film (first emitting compound / first host material). The same applies to "the same configuration as the second light-emitting layer."
[0149] The first film measurement sample and the second film measurement sample were prepared as follows. A first host material (BH1) and a first luminescent compound (BD1) were co-deposited on a quartz substrate (25 x 25 mm) so that the ratio (by mass) of the first luminescent compound to the first host material contained in the first luminescent layer (first luminescent compound / first host material) was the same, forming a 50 nm thick first film measurement sample. A sealing glass (outer dimensions 17 x 17 mm, inner dimensions 13 x 13 mm, recessed depth 0.5 mm) coated with a coating-type desiccant (Futaba Corporation, OleDry-P2) was then sealed with a UV-curable resin (ThreeBond Fine Chemicals, TB3124N(IE)). A second film measurement sample was similarly formed. For the PL spectrum measurement, a fluorescence spectrum measurement device (fluorescence spectrophotometer F-7000 (manufactured by Hitachi High-Tech Science Corporation)) is used. The measurement conditions are as follows. The film measurement sample is excited at a specific wavelength (a wavelength 30 nm shorter than the maximum peak wavelength of the absorption spectrum) and the maximum peak wavelength λ (unit: nm) and full width at half maximum FWHM (unit: nm) of the film are calculated from the obtained PL spectrum.
[0150] In this specification, the term "host material" refers to a material that is contained in, for example, "50% by mass or more of the layer." Thus, for example, the first light-emitting layer contains the first host material in an amount of 50% by mass or more of the total mass of the first light-emitting layer. The second light-emitting layer contains, for example, the second host material in an amount of 50% by mass or more of the total mass of the second light-emitting layer.
[0151] (Light-emitting area) The light-emitting region is disposed between the anode and the cathode. In the organic EL device according to this embodiment, the light-emitting region includes a first light-emitting layer and a second light-emitting layer.
[0152] In the organic EL device according to this embodiment, the first light-emitting layer may be disposed between the anode and the second light-emitting layer, or the first light-emitting layer may be disposed between the cathode and the second light-emitting layer. In the organic EL device according to this embodiment, the first light-emitting layer is preferably disposed between the anode and the second light-emitting layer.
[0153] In the organic EL device according to this embodiment, one of the first light-emitting layer and the second light-emitting layer is preferably the layer disposed closest to the cathode among the multiple layers in the light-emitting region.
[0154] The organic EL device according to this embodiment may have an anode, a first light-emitting layer, a second light-emitting layer, and a cathode in this order, or the order of the first light-emitting layer and the second light-emitting layer may be reversed, i.e., an anode, a second light-emitting layer, a first light-emitting layer, and a cathode in this order.
[0155] In the organic EL device according to this embodiment, the first light-emitting compound and the second light-emitting compound are preferably each independently a compound that emits light with a maximum peak wavelength of 500 nm or less.
[0156] (First light-emitting layer) The first light-emitting layer contains a first host material and a first light-emitting compound. The first host material is a compound different from the second host material contained in the second light-emitting layer.
[0157] In the organic EL device according to this embodiment, the first light-emitting compound more preferably emits light having a maximum peak wavelength of 480 nm or less. In the organic EL device according to this embodiment, the first light-emitting compound preferably emits light with a maximum peak wavelength of 430 nm or more.
[0158] In the organic EL device according to this embodiment, the first light-emitting compound is preferably a fluorescent compound. In the organic EL device according to this embodiment, the first light-emitting compound preferably exhibits fluorescent emission with a maximum peak wavelength of 500 nm or less, and more preferably exhibits fluorescent emission with a maximum peak wavelength of 480 nm or less. In the organic EL device according to this embodiment, the first light-emitting compound preferably exhibits fluorescent emission with a maximum peak wavelength of 430 nm or more.
[0159] The maximum peak wavelength of a compound is measured as follows: A 5 μmol / L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the emission spectrum of this sample (vertical axis: emission intensity, horizontal axis: wavelength) is measured at room temperature (300 K). The emission spectrum can be measured using a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measurement device is not limited to the device used here. In the emission spectrum, the peak wavelength at which the emission intensity is maximum is defined as the maximum peak wavelength. In this specification, the maximum peak wavelength of fluorescent emission may be referred to as the maximum fluorescent emission peak wavelength (FL-peak).
[0160] In the emission spectrum of the first light-emitting compound, the peak at which the emission intensity is greatest is defined as the maximum peak, and when the height of the maximum peak is defined as 1, the heights of other peaks appearing in the emission spectrum are preferably less than 0.6. Note that the peaks in the emission spectrum are defined as local maxima. In addition, it is preferable that the number of peaks in the emission spectrum of the first luminescent compound is less than three.
[0161] In the organic EL device according to this embodiment, the first light-emitting compound is preferably a compound that does not contain an azine ring structure in the molecule.
[0162] In the organic EL device according to this embodiment, the first light-emitting compound is preferably not a boron-containing complex, and more preferably not a complex.
[0163] In the organic EL device according to this embodiment, the first light-emitting layer preferably does not contain a metal complex. Also, in the organic EL device according to this embodiment, the first light-emitting layer preferably does not contain a boron-containing complex.
[0164] In the organic EL device according to this embodiment, the first light-emitting layer preferably does not contain a phosphorescent material (dopant material). The first light-emitting layer preferably does not contain a heavy metal complex or a phosphorescent rare earth metal complex, such as an iridium complex, an osmium complex, or a platinum complex.
[0165] In the organic EL device according to 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 light-emitting compound satisfy the relationship of the following mathematical formula (Mathematical Formula 3). T1(D1)>T1(H1) ... (Number 3)
[0166] When the first host material and the first light-emitting compound satisfy the relationship of mathematical formula (Mathematical Formula 3), triplet excitons generated in the first light-emitting layer move over the first host material rather than the first light-emitting compound, which has a higher triplet energy, and are therefore more likely to move to the second light-emitting layer.
[0167] In the organic EL device according to 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 light-emitting compound satisfy the relationship shown in the following mathematical formula (Mathematical Formula 4). The singlet energy S1 refers to the energy difference between the lowest excited singlet state and the ground state. S1(H1)>S1(D1) ... (Number 4)
[0168] When the first host material and the first light-emitting compound satisfy the relationship of mathematical formula (Mathematical Formula 4), singlet excitons generated on the first host material can easily transfer energy from the first host material to the first light-emitting compound, contributing to the fluorescent emission of the first light-emitting compound.
[0169] The organic EL element according to this embodiment preferably satisfies the relationship of the following mathematical formula (Mathematical Formula 3B). T1(D1)>T1(H1)>T1(H2)…(Number 3B)
[0170] (Triplet energy T1) The triplet energy T1 can be measured by the following method. The compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) at 10 -5 mol / L or more 10 -4 The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this sample is measured at low temperature (77[K]), and a tangent line is 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 is determined. edge Based on [nm], the amount of energy calculated using the following conversion formula (F1) is taken as the triplet energy T1. Conversion formula (F1): T1[eV]=1239.85 / λ edge
[0171] The tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows: When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum of the spectral maxima, consider the tangent at each point on the curve toward the long wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope is at its maximum (i.e., the tangent at the inflection point) is the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that a maximum point having a peak intensity that is 15% or less of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and the tangent drawn at the point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side is defined as the tangent to the rising edge on the short wavelength side of the phosphorescence spectrum. Phosphorescence can be measured using an F-4500 spectrofluorophotometer manufactured by Hitachi High-Technologies Corp. However, the measuring device is not limited to this, and measurements may be performed by combining a cooling device, a cryogenic container, an excitation light source, and a light-receiving device.
[0172] (singlet energy S1) The following method can be mentioned as a method for measuring the singlet energy S1 using a solution (sometimes referred to as a solution method). 10 of the compounds to be measured -5 mol / L or more 10 -4 A toluene solution of 1000 mol / L or less is prepared and placed in a quartz cell, and the absorption spectrum (vertical axis: absorption intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300 K). A tangent line is drawn to the falling edge on the long wavelength side of this absorption spectrum, and the wavelength value λedge [nm] at the intersection of this tangent line and the horizontal axis is substituted into the following conversion formula (F2) to calculate the singlet energy. Conversion formula (F2): S1[eV]=1239.85 / λedge An example of an absorption spectrum measuring device is a spectrophotometer manufactured by Hitachi (device name: U3310), but is not limited to this.
[0173] The tangent to the fall on the long wavelength side of the absorption spectrum is drawn as follows. When moving along the spectral curve from the longest maximum value on the longest wavelength side of the absorption spectrum toward longer wavelengths, consider the tangent at each point on the curve. 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 slope is minimum on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is considered to be the tangent to the fall on the long wavelength side of the absorption spectrum. Note that maximum points with absorbance values of 0.2 or less are not included in the maximum values on the longest wavelength side.
[0174] In the organic EL device according to this embodiment, the first light-emitting compound is preferably contained in the first light-emitting layer in an amount of 0.5% by mass or more. That is, the first light-emitting layer preferably contains the first light-emitting compound in an amount of 0.5% by mass or more of the total mass of the first light-emitting layer, more preferably 1.0% by mass or more of the total mass of the first light-emitting layer, even more preferably 1.2% by mass or more of the total mass of the first light-emitting layer, and even more preferably 1.5% by mass or more of the total mass of the first light-emitting layer. The first light-emitting layer preferably contains the first light-emitting compound in an amount of 10 mass % or less of the total mass of the first light-emitting layer, more preferably 7 mass % or less of the total mass of the first light-emitting layer, and even more preferably 5 mass % or less of the total mass of the first light-emitting layer.
[0175] In the organic EL device according to this embodiment, the first emitting layer preferably contains the first compound as a first host material in an amount of 60 mass % or more of the total mass of the first emitting layer, more preferably 70 mass % or more of the total mass of the first emitting layer, even more preferably 80 mass % or more of the total mass of the first emitting layer, still more preferably 90 mass % or more of the total mass of the first emitting layer, and even more preferably 95 mass % or more of the total mass of the first emitting layer. The first emitting layer preferably contains the first host material in an amount of 99% by mass or less of the total mass of the first emitting layer. However, 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.
[0176] In this embodiment, the first light-emitting layer may contain a material other than the first host material and the first light-emitting compound. The first light-emitting layer may contain only one type of first host material or two or more types of first light-emitting compounds.
[0177] In the organic EL device according to this embodiment, the thickness of the first light-emitting layer is preferably 3 nm or more, more preferably 5 nm or more, which is sufficient to cause recombination of holes and electrons in the first light-emitting layer. In the organic EL device according to this embodiment, the thickness of the first emitting layer is preferably 15 nm or less, more preferably 10 nm or less, which is thin enough to allow triplet excitons to migrate to the second emitting layer. In the organic EL device according to this embodiment, the thickness of the first light-emitting layer is more preferably 3 nm or more and 15 nm or less.
[0178] (Second light-emitting layer) In the organic EL device according to this embodiment, the second light-emitting layer contains a second host material and a second light-emitting compound. The second host material is a compound different from the first host material contained in the first light-emitting layer. In the organic EL device according to this embodiment, the first light-emitting compound and the second light-emitting compound may be the same or different.
[0179] In the organic EL device according to this embodiment, the second light-emitting compound more preferably emits light having a maximum peak wavelength of 480 nm or less. In the organic EL device according to this embodiment, the second light-emitting compound preferably emits light with a maximum peak wavelength of 430 nm or more.
[0180] In the organic EL device according to this embodiment, the second light-emitting compound is preferably a fluorescent compound. In the organic EL device according to this embodiment, the second light-emitting compound preferably exhibits fluorescent emission with a maximum peak wavelength of 500 nm or less, and more preferably exhibits fluorescent emission with a maximum peak wavelength of 480 nm or less. In the organic EL device according to this embodiment, the second light-emitting compound preferably exhibits fluorescent emission with a maximum peak wavelength of 430 nm or more. The method for measuring the maximum peak wavelength of the compound is as described above.
[0181] In the organic EL device according to this embodiment, the half width of the maximum peak of the second light-emitting compound is preferably 1 nm or more and 20 nm or less.
[0182] In the organic EL device according to this embodiment, it is preferable that the triplet energy T1(D2) of the second light-emitting compound and the triplet energy T1(H2) of the second host material satisfy the relationship of the following mathematical formula (Mathematical Formula 5). T1(D2)>T1(H2) ... (Number 5)
[0183] In the organic EL device according to this embodiment, the second light-emitting compound and the second host material satisfy the relationship of the above mathematical formula (Mathematical Formula 5), so that triplet excitons generated in the first light-emitting layer transfer energy to molecules of the second host material, rather than to the second light-emitting compound having a higher triplet energy, when they move to the second light-emitting layer. Furthermore, triplet excitons generated by recombination of holes and electrons on the second host material do not transfer to the second light-emitting compound having a higher triplet energy. Triplet excitons generated by recombination on molecules of the second light-emitting compound quickly transfer energy to molecules of the second host material. Triplet excitons in the second host material do not transfer to the second light-emitting compound, but instead efficiently collide with each other on the second host material due to the TTF phenomenon, generating singlet excitons.
[0184] In the organic EL device according to 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 light-emitting compound satisfy the relationship shown in the following formula (6). S1(H2)>S1(D2)…(Math 6)
[0185] In the organic EL device according to this embodiment, the second light-emitting compound and the second host material satisfy the relationship of the above mathematical formula (Mathematical Formula 6), and therefore the singlet energy of the second light-emitting compound is smaller than the singlet energy of the second host material. Therefore, the singlet excitons generated by the TTF phenomenon transfer energy from the second host material to the second light-emitting compound, contributing to the fluorescent emission of the second light-emitting compound.
[0186] In the organic EL device according to this embodiment, the second light-emitting compound is preferably a compound that does not contain an azine ring structure in the molecule.
[0187] In the organic EL device according to this embodiment, the second light-emitting compound is preferably not a boron-containing complex, and more preferably not a complex.
[0188] In the organic EL device according to this embodiment, the second light-emitting layer preferably does not contain a metal complex. Also, in the organic EL device according to this embodiment, the second light-emitting layer preferably does not contain a boron-containing complex.
[0189] In the organic EL device according to this embodiment, the second light-emitting layer preferably does not contain a phosphorescent material (dopant material). The second light-emitting layer preferably does not contain a heavy metal complex or a phosphorescent rare earth metal complex, such as an iridium complex, an osmium complex, or a platinum complex.
[0190] In the organic EL device according to this embodiment, the second light-emitting compound is preferably contained in the second light-emitting layer in an amount of 0.5% by mass or more. That is, the second light-emitting layer preferably contains the second light-emitting compound in an amount of 0.5% by mass or more of the total mass of the second light-emitting layer, more preferably 1.0% by mass or more of the total mass of the second light-emitting layer, even more preferably 1.2% by mass or more of the total mass of the second light-emitting layer, and even more preferably 1.5% by mass or more of the total mass of the second light-emitting layer. The second light-emitting layer preferably contains the second light-emitting compound in an amount of 10 mass % or less of the total mass of the second light-emitting layer, more preferably 7 mass % or less of the total mass of the second light-emitting layer, and even more preferably 5 mass % or less of the total mass of the second light-emitting layer.
[0191] The second emitting layer preferably contains the second compound as a second host material in an amount of 60 mass% or more of the total mass of the second emitting layer, more preferably 70 mass% or more of the total mass of the second emitting layer, even more preferably 80 mass% or more of the total mass of the second emitting layer, still more preferably 90 mass% or more of the total mass of the second emitting layer, and even more preferably 95 mass% or more of the total mass of the second emitting layer. The second emitting layer preferably contains the second host material in an amount of 99% by mass or less of the total mass of the second emitting layer. When 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.
[0192] Note that this embodiment does not exclude the case where the second light-emitting layer contains a material other than the second host material and the second light-emitting compound. The second light-emitting layer may contain only one type of second host material or two or more types of second light-emitting compounds.
[0193] In the organic EL device according to this embodiment, the thickness of the second emitting layer is preferably 5 nm or more, more preferably 15 nm or more. When the thickness of the second emitting layer is 5 nm or more, triplet excitons that have migrated from the first emitting layer to the second emitting layer can be easily prevented from returning to the first emitting layer. Furthermore, when the thickness of the second emitting layer is 5 nm or more, triplet excitons can be sufficiently separated from the recombination site in the first emitting layer. In the organic EL device according to this embodiment, the thickness of the second light-emitting layer is preferably 20 nm or less, which can increase the density of triplet excitons in the second light-emitting layer and make the TTF phenomenon more likely to occur. In the organic EL device according to this embodiment, the second light-emitting layer preferably has a thickness of 5 nm or more and 20 nm or less.
[0194] In the organic EL device according to this embodiment, it is preferable that the triplet energy T1(DX) of the compound contained in the first emitting layer and exhibiting fluorescent emission with a main peak wavelength of 500 nm or less or the triplet energy T1(DX) of the compound contained in the second emitting layer and exhibiting fluorescent emission with a main peak wavelength of 500 nm or less, 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 (Formula 10). 2.6eV>T1(DX)>T1(H1)>T1(H2)…(Number 10)
[0195] When the first emitting layer contains a first emitting compound, the triplet energy T1(D1) of the first emitting compound preferably satisfies the relationship of the following mathematical formula (Mathematical Formula 10A). 2.6eV>T1(D1)>T1(H1)>T1(H2) ... (several tens of amperes)
[0196] When the second emitting layer contains a second emitting compound, the triplet energy T1(D2) of the second emitting compound preferably satisfies the relationship of the following mathematical formula (Mathematical Formula 10B). 2.6eV>T1(D2)>T1(H1)>T1(H2)…(Several 10B)
[0197] In the organic EL device according to this embodiment, it is preferable that the triplet energy T1(DX) of the compound contained in the first emitting layer and exhibiting fluorescent emission with a main peak wavelength of 500 nm or less or the triplet energy T1(H1) of the compound contained in the second emitting layer and exhibiting fluorescent emission with a main peak wavelength of 500 nm or less satisfies the relationship of the following mathematical formula (Mathematical Formula 11): 0 eV < T1(DX) - T1(H1) < 0.6 eV …(Equation 11)
[0198] When the first light-emitting layer contains a first light-emitting compound, the triplet energy T1(D1) of the first light-emitting compound material preferably satisfies the relationship of the following mathematical formula (Equation 11A). 0 eV < T1(D1) - T1(H1) < 0.6 eV …(Equation 11A)
[0199] When the second light-emitting layer contains a second light-emitting compound, the triplet energy T1(D2) of the second light-emitting compound preferably satisfies the relationship of the following mathematical formula (Equation 11B). 0 eV < T1(D2) - T1(H2) < 0.8 eV …(Equation 11B)
[0200] In the organic EL element according to the present embodiment, the triplet energy T1(H1) of the first host material preferably satisfies the relationship of the following mathematical formula (Equation 12). T1(H1) > 2.0 eV …(Equation 12)
[0201] In the organic EL element according to the present embodiment, it is also preferable that the triplet energy T1(H1) of the first host material satisfies the relationship of the following mathematical formula (Equation 12A), and it is also preferable that the triplet energy T1(H1) satisfies the relationship of the following mathematical formula (Equation 12B). T1(H1) > 2.10 eV …(Equation 12A) T1(H1) > 2.15 eV …(Equation 12B)
[0202] In the organic EL element according to the present embodiment, when the triplet energy T1(H1) of the first host material satisfies the relationship of the mathematical formula (Equation 12A) or the mathematical formula (Equation 12B), the triplet excitons generated in the first light-emitting layer are likely to move to the second light-emitting layer, and it is also likely to suppress the reverse movement from the second light-emitting layer to the first light-emitting layer. As a result, singlet excitons are efficiently generated in the second light-emitting layer, and the luminous efficiency is improved.
[0203] In the organic EL device according to this embodiment, the triplet energy T1(H1) of the first host material preferably satisfies the relationship of the following mathematical formula (12C), and also preferably satisfies the relationship of the following mathematical formula (12D). 2.08eV>T1(H1)>1.87eV …(math 12C) 2.05eV>T1(H1)>1.90eV …(math 12D)
[0204] In the organic EL element according to this embodiment, when the triplet energy T1(H1) of the first host material satisfies the relationship of the above-mentioned formula (12C) or (12D), the energy of the triplet excitons generated in the first emitting layer becomes small, and the lifetime of the organic EL element can be expected to be extended.
[0205] In the organic EL device according to this embodiment, it is preferable that the triplet energy T1(F1) of the compound contained in the first emitting layer, which exhibits fluorescent emission with a main peak wavelength of 500 nm or less, satisfies the relationship of the following mathematical formula (14A), and it is also preferable that the triplet energy T1(F1) of the compound contained in the first emitting layer satisfies the relationship of the following mathematical formula (14B): 2.60eV>T1(F1) ... (Number 14A) 2.50eV>T1(F1) ... (Math 14B) When the first light-emitting layer contains a compound that satisfies the relationship of the above mathematical formula (14A) or (14B), the life of the organic EL device is extended.
[0206] In the organic EL device according to this embodiment, it is preferable that the triplet energy T1(F2) of the compound contained in the second emitting layer, which exhibits fluorescent emission with a main peak wavelength of 500 nm or less, satisfies the relationship of the following mathematical formula (14C), and it is also preferable that the triplet energy T1(F2) of the compound contained in the second emitting layer satisfies the relationship of the following mathematical formula (14D): 2.60eV>T1(F2) ...(Number 14C) 2.50eV>T1(F2) ...(Math 14D) When the second light-emitting layer contains a compound that satisfies the relationship of the above-mentioned formula (14C) or (14D), the life of the organic EL device is extended.
[0207] In the organic EL device according to this embodiment, it is preferable that the triplet energy T1(H2) of the second host material satisfies the relationship of the following mathematical formula (Mathematical Formula 13). T1(H2)≧1.9 eV … (Equation 13)
[0208] (Other layers of organic EL element) The organic EL device according to this embodiment may have one or more organic layers in addition to the first and second light-emitting layers, such as at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron injection layer, and an electron transport layer.
[0209] The organic EL device according to this embodiment may be configured with only the first light-emitting layer and the second light-emitting layer, or may further include, for example, at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron injection layer, and an electron transport layer.
[0210] In the organic EL element according to this embodiment, when the first emitting layer and the second emitting layer are stacked in the order of the first emitting layer and the second emitting layer from the anode side, it is preferable that the electron mobility μe(H1) of the first host material and the electron mobility μe(H2) of the second host material satisfy the relationship of the following mathematical formula (Mathematical Formula 30). μe(H2)>μe(H1) …(Number 70) When the first host material and the second host material satisfy the relationship of the above mathematical formula (70), the recombination ability of holes and electrons in the first light-emitting layer is improved.
[0211] In the organic EL element according to this embodiment, when the first emitting layer and the second emitting layer are stacked in the order of the first emitting layer and the second emitting layer from the anode side, it is also preferable that the hole mobility μh(H1) of the first host material and the hole mobility μh(H2) of the second host material satisfy the relationship shown in the following formula (Formula 71). μh(H1)>μh(H2) …(Equation 71)
[0212] In the organic EL element according to this embodiment, when the first emitting layer and the second emitting layer are stacked in the order of the first emitting layer and the second emitting layer from the anode side, it is also preferable that the hole mobility μh(H1) of the first host material, the electron mobility μe(H1) of the first host material, the hole mobility μh(H2) of the second host material, and the electron mobility μe(H2) of the second host material satisfy the relationship shown in the following formula (72). (μe(H2) / μh(H2))>(μe(H1) / μh(H1)) …(Number 72)
[0213] The electron mobility can be measured by measuring impedance using a mobility evaluation element fabricated by the following procedure. The mobility evaluation element is fabricated, for example, by the following procedure. A compound (Target) whose electron mobility is to be measured is vapor-deposited on a glass substrate with an aluminum electrode (anode) so as to cover the aluminum electrode, thereby forming a measurement target layer. An electron transport layer is formed on this measurement target layer by vapor-depositing the following compound bET-1. An electron injection layer is formed on this electron transport layer by vapor-depositing LiF. A metal cathode is formed on this electron injection layer by vapor-depositing metallic aluminum (Al). The above-mentioned configuration of the device for evaluating mobility can be shown in simplified form as follows. glass / Al(50) / Target(200) / bET-1(10) / LiF(1) / Al(50) The numbers in parentheses indicate the film thickness (nm).
[0214] [ka]
[0215] The element for evaluating electron mobility is placed in an impedance measurement device and impedance measurement is performed. The impedance measurement is performed by sweeping the measurement frequency from 1 Hz to 1 MHz. At this time, a DC voltage V is applied to the element simultaneously with an AC amplitude of 0.1 V. The modulus M is calculated from the measured impedance Z using the relationship in the following calculation formula (C1). Calculation formula (C1): M=jωZ In the above formula (C1), j is an imaginary unit whose square is -1, and ω is the angular frequency [rad / s]. In a Bode plot with the imaginary part of the modulus M on the vertical axis and frequency [Hz] on the horizontal axis, the electrical time constant τ of the mobility evaluation element is calculated from the frequency fmax showing the peak using the following calculation formula (C2). Calculation formula (C2): τ=1 / (2πfmax) In the above formula (C2), π is the symbol representing the ratio of the circumference of a circle to its diameter. Using the above τ, the electron mobility μe is calculated from the relationship of the following calculation formula (C3-1). Calculation formula (C3-1):μe=d 2 / (Vτ) In the above formula (C3-1), d is the total film thickness of the organic thin films that make up the device, and in the case of the device configuration for evaluating the electron mobility, d=210 [nm].
[0216] The hole mobility can be measured by measuring impedance using a mobility evaluation device fabricated by the following procedure. The mobility evaluation device is fabricated, for example, by the following procedure. On a glass substrate with an ITO transparent electrode (anode), the following compound HIL-1 is vapor-deposited so as to cover the transparent electrode to form a hole injection layer. On this hole injection layer, the following compound HTL-1 is vapor-deposited to form a hole transport layer. Subsequently, a compound Target, whose hole mobility is to be measured, is vapor-deposited to form a measurement target layer. On this measurement target layer, metallic aluminum (Al) is vapor-deposited to form a metal cathode. The above-mentioned configuration of the device for evaluating mobility can be shown in simplified form as follows. ITO(130) / HIL-1(5) / HTL-1(10) / Target(200) / Al(80) The numbers in parentheses indicate the film thickness (nm).
[0217] [ka]
[0218] The hole mobility evaluation device is placed in an impedance measurement device, and impedance measurement is performed. The impedance measurement is performed by sweeping the measurement frequency from 1 Hz to 1 MHz. At this time, a DC voltage V is applied to the device simultaneously with an AC amplitude of 0.1 V. The modulus M is calculated from the measured impedance Z using the relationship in the above calculation formula (C1). In a Bode plot with the imaginary part of the modulus M on the vertical axis and frequency [Hz] on the horizontal axis, the electrical time constant τ of the mobility evaluation element is calculated from the frequency fmax showing the peak using the above calculation formula (C2). Using τ obtained from the above formula (C2), the hole mobility μh is calculated from the relationship of the following formula (C3-2). Calculation formula (C3-2):μh=d 2 / (Vτ) In the above formula (C3-2), d is the total film thickness of the organic thin films that make up the device, and in the case of the device configuration for evaluating hole mobility, d=215 [nm].
[0219] The electron and hole mobilities herein are expressed as the square root of the electric field strength, E 1 / 2 =500[V 1 / 2 / cm 1 / 2 The square root of the electric field strength E 1 / 2 can be calculated from the relationship of the following calculation formula (C4). Calculation formula (C4): E 1 / 2 =V 1 / 2 / d 1 / 2 The impedance measurement is performed using a Solartron 1260 model impedance measuring device, and for higher accuracy, a Solartron 1296 model dielectric constant measurement interface can also be used.
[0220] In the organic EL device according to this embodiment, the first light-emitting layer and the second light-emitting layer are preferably in direct contact with each other.
[0221] In this specification, a layer structure in which "the first light-emitting layer and the second light-emitting layer are in direct contact with each other" can include, for example, any of the following embodiments (LS1), (LS2), and (LS3). (LS1) An embodiment in which a region in which both the first host material and the second host material are mixed is generated during the process of vapor-depositing the compound for the first emitting layer and the compound for the second emitting layer, and this region is present at the interface between the first emitting layer and the second emitting layer. (LS2) When the first emitting layer and the second emitting layer contain a light-emitting compound, a region in which the first host material, the second host material, and the light-emitting compound are mixed is generated during the process of vapor-depositing the compound for the first emitting layer and the process of vapor-depositing the compound for the second emitting layer, and this region is present at the interface between the first emitting layer and the second emitting layer. (LS3) When the first emitting layer and the second 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-depositing the compound for the first emitting layer and the compound for the second emitting layer, and the region is present at the interface between the first emitting layer and the second emitting layer.
[0222] (Schematic structure of organic EL element) An example of the schematic configuration of an organic EL element according to this embodiment is shown in Fig. 1. The organic EL element 1 shown in Fig. 1 is a top-emission organic EL element, and the light extraction side is the cathode 4 side. The organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is configured by laminating, in this order from the anode 3 side, a hole injection layer 61, a hole transport layer 62, a first light-emitting layer 51, a second light-emitting layer 52, an electron transport layer 71, and an electron injection layer 72. The anode 3 of the organic EL element 1 includes a conductive layer 31 and a light-reflecting layer 32, and the conductive layer 31 is disposed between the light-reflecting layer 32 and the hole injection layer 61. The light-emitting region 5 of the organic EL element 1 includes the first light-emitting layer 51 on the anode 3 side and the second light-emitting layer 52 on the cathode 4 side.
[0223] A schematic configuration of another example of the organic EL element according to this embodiment is shown in Fig. 2. The organic EL element 1A shown in Fig. 2 is a bottom-emission organic EL element, and the light extraction side is the anode 3A side. The organic EL element 1A includes a light-transmitting substrate 2A, an anode 3A, a cathode 4A, and an organic layer 10 disposed between the anode 3A and the cathode 4A. The organic layer 10 is formed by stacking, in this order from the anode 3A side, a hole injection layer 61, a hole transport layer 62, a first light-emitting layer 51, a second light-emitting layer 52, an electron transport layer 71, and an electron injection layer 72. The organic EL element 1A also includes a color conversion section 8 that transmits light emitted from the first light-emitting layer 51 and the second light-emitting layer 52. In the organic EL element 1A, the color conversion section 8 is a color filter. The color conversion section 8 is disposed on the anode 3A side, which is the light extraction side of the organic EL element 1A. In the example shown in FIG. 2, the color conversion section 8 is disposed on the surface of the substrate 2A opposite to the surface facing the anode 3A.
[0224] The organic EL element according to this embodiment is not limited to the configuration of the organic EL element shown in FIGS. An example of an organic EL element having a different configuration is an organic EL element including organic layers in which a hole injection layer, a hole transport layer, a second light-emitting layer, a first light-emitting layer, an electron transport layer, and an electron injection layer are stacked in this order from the anode side. Another example of an organic EL element having a different configuration is a top-emission organic EL element in which a color conversion unit is disposed on the cathode side, which is the light extraction side. In this embodiment, the color conversion unit (e.g., a color filter and quantum dots) is disposed on the cathode. An example of an organic EL element having a different configuration is a top-emission organic EL element in which a light-reflecting layer, a substrate, and a conductive layer are arranged in this order. Furthermore, examples of organic EL elements with different configurations include bottom-emission organic EL elements in which a color conversion section is disposed between a substrate and an anode. Furthermore, examples of organic EL elements with different configurations include bottom-emission organic EL elements that do not have a color conversion section.
[0225] The structure of the organic EL element will be further described below. Hereinafter, the reference numerals may be omitted.
[0226] In the organic EL device according to this embodiment, an organic layer may be disposed between the first light-emitting layer and the second light-emitting layer.
[0227] (intervening layer) The organic EL device according to this embodiment may also have an intervening layer as an organic layer disposed between the first light-emitting layer and the second light-emitting layer. In this embodiment, in order to prevent the Singlet light-emitting region and the TTF light-emitting region from overlapping, the intervening layer does not contain a light-emitting compound to the extent that this can be achieved. For example, the content of the luminescent compound in the intervening layer is not limited to 0% by mass, but if the luminescent compound is, for example, a component unintentionally mixed in during the manufacturing process or a component contained as an impurity in the raw materials, the intervening layer is allowed to contain these components. For example, if all materials constituting the intervening layer are material A, material B, and material C, the content of each of material A, material B, and material C in the intervening layer is 10 mass% or more, and the total content of material A, material B, and material C is 100 mass%. Hereinafter, the intervening layer may be referred to as a "non-doped layer," and the layer containing the light-emitting compound may be referred to as a "doped layer."
[0228] In general, when the light-emitting layer has a laminated structure, the Singlet light-emitting region and the TTF light-emitting region are easily separated, which is said to improve the light-emitting efficiency. In the organic EL device of this embodiment, when an intervening layer (non-doped layer) is disposed between the first and second light-emitting layers in the light-emitting region, the overlapping area between the Singlet light-emitting region and the TTF light-emitting region is reduced, and it is expected that the decrease in TTF efficiency caused by collisions between triplet excitons and carriers is suppressed. In other words, it is believed that the insertion of an intervening layer (non-doped layer) between the light-emitting layers contributes to improving the efficiency of TTF light emission.
[0229] The intermediate layer is a non-doped layer. The intervening layer does not contain metal atoms, and therefore does not contain a metal complex. The intervening layer includes an intervening layer material that is not a light-emitting compound. The material for the intervening layer is not particularly limited as long as it is a material other than a light-emitting compound. Examples of materials for the intervening layer include: 1) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives; 2) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and chrysene derivatives; and 3) aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives.
[0230] The material for the intervening layer can be either or both of the first host material and the second host material, but is not particularly limited as long as it separates the Singlet emission region and the TTF emission region and does not inhibit the Singlet emission and the TTF emission.
[0231] In the organic EL device according to this embodiment, the content of each of the materials constituting the intervening layer in the intervening layer is 10% by mass or more. The intermediate layer includes the intermediate layer material as a material constituting the intermediate layer. The intervening layer preferably contains the intervening layer material in an amount of 60% by mass or more of the total mass of the intervening layer, more preferably 70% by mass or more of the total mass of the intervening layer, even more preferably 80% by mass or more of the total mass of the intervening layer, even more preferably 90% by mass or more of the total mass of the intervening layer, and even more preferably 95% by mass or more of the total mass of the intervening layer. The intervening layer may contain only one type of intervening layer material, or may contain two or more types. When the intervening layer contains two or more types of intervening layer materials, the upper limit of the total content of the two or more intervening layer materials is 100% by mass. It should be noted that this embodiment does not exclude the case where the intervening layer contains a material other than the intervening layer material.
[0232] The intervening layer may be composed of a single layer or may be composed of two or more layers laminated together.
[0233] The thickness of the intervening layer is not particularly limited as long as it can prevent the Singlet light-emitting region and the TTF light-emitting region from overlapping, but it is preferably 3 nm or more and 15 nm or less per layer, and more preferably 5 nm or more and 10 nm or less. If the thickness of the intervening layer is 3 nm or more, it becomes easier to separate the Singlet emission region from the emission region derived from TTF. If the thickness of the intervening layer is 15 nm or less, it becomes easier to prevent the host material of the intervening layer from emitting light.
[0234] The intervening layer includes an intervening layer material as a material constituting the intervening layer, and has a triplet energy T1(H1) of the first host material, a triplet energy T1(H2) of the second host material, and a triplet energy T1(M mid ) preferably satisfies the relationship of the following mathematical formula (Mathematical Formula 21). T1(H1) ≧ T1(M mid ) ≧ T1(H2) … (Equation 21)
[0235] When the intervening layer contains two or more intervening layer materials as materials constituting the intervening layer, the triplet energy T1(H1) of the first host material, the triplet energy T1(H2) of the second host material, and the triplet energy T1(M EA ) more preferably satisfy the relationship of the following mathematical formula (Math. 21A). T1(H1) ≧ T1(M EA ) ≧ T1(H2) …(Number 21A)
[0236] (substrate) The substrate is used as a support for the organic EL element. Examples of materials that can be used for the substrate include glass, quartz, and plastic. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate. Examples of materials for forming the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Inorganic vapor-deposited films may also be used.
[0237] (anode) The anode formed on the substrate is preferably made of a metal, alloy, electrically conductive compound, or mixture thereof with a large work function (specifically, 4.0 eV or higher). Specific examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metal materials (e.g., titanium nitride).
[0238] These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1% by mass or more and 10% by mass or less of zinc oxide added to indium oxide. Furthermore, for example, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5% by mass or more and 5% by mass or less of tungsten oxide and 0.1% by mass or more and 1% by mass or less of zinc oxide relative to indium oxide. Alternatively, the films may be formed by vacuum deposition, coating, inkjet printing, spin coating, or the like.
[0239] Of the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that easily injects holes regardless of the work function of the anode, so materials that can be used as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures of these, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.
[0240] Materials with low work functions, such as elements belonging to Group 1 or 2 of the periodic table, can also be used. These include 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 metals (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these metals. Vacuum deposition and sputtering methods can be used to form the anode using alkali metals, alkaline earth metals, and alloys containing these metals. Furthermore, when using silver paste, coating methods and inkjet methods can be used.
[0241] When the organic EL element is a bottom-emission type, the anode is a light-transmitting electrode having light-transmitting properties. The light-transmitting electrode is preferably formed of a light-transmitting or semi-transmitting metal material that transmits light emitted from the light-emitting layer. In this specification, light-transmitting or semi-transmitting means the property of transmitting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The light-transmitting or semi-transmitting metal material can be appropriately selected from the materials listed in the anode section. The light-transmitting or semi-transmitting metal material may be a material listed as a material used for the conductive layer (or transparent conductive layer) described below.
[0242] When the organic EL device is a top-emission type, the anode is a light-reflective electrode having a light-reflective layer. The light-reflective layer is preferably formed of a metal material having light reflectivity. In this specification, light reflectivity means the property of reflecting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The metal material having light reflectivity can be appropriately selected from the materials listed in the above section on the anode. Examples of metal materials used for the light-reflecting layer include a simple metal material selected from the group consisting of Al, Ag, Ta, Zn, Mo, W, Ni, and Cr, or an alloy material containing a metal selected from this group as the main component (preferably 50% by mass or more of the total); an amorphous alloy selected from the group consisting of NiP, NiB, CrP, and CrB; and a microcrystalline alloy selected from the group consisting of NiAl and silver alloys. In addition, the metal material used for the light-reflecting layer may be at least one alloy selected from the group consisting of APC (an alloy of silver, palladium, and copper), ARA (an alloy of silver, rubidium, and gold), MoCr (an alloy of molybdenum and chromium), and NiCr (an alloy of nickel and chromium). The light-reflecting layer may be a single layer or multiple layers.
[0243] The anode as a light-reflective electrode may be composed of only a light-reflecting layer, or may have a multilayer structure including a light-reflecting layer and a conductive layer (preferably a transparent conductive layer). When the anode has a light-reflecting layer and a conductive layer, the conductive layer is preferably disposed between the reflective layer and a layer including a hole-transporting region (e.g., a hole-injection layer or a hole-transporting layer). The anode may also have a multilayer structure in which a light-reflecting layer is disposed between two conductive layers (a first conductive layer and a second conductive layer). In such a multilayer structure, the first conductive layer and the second conductive layer may be formed of the same material or different materials. The material used for the conductive layer can be appropriately selected from the materials listed in the anode section. In addition, the conductive layer (transparent conductive layer) serving as a transparent electrode can also be made of a metal, alloy, electrically conductive compound, or mixture thereof having a large work function (specifically, 4.0 eV or more). Furthermore, the conductive layer may 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.
[0244] (cathode) The cathode is preferably made of a metal, alloy, electrically conductive compound, or mixture thereof, each having a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.
[0245] When an alkali metal, an alkaline earth metal, or an alloy containing these is used to form a cathode, a vacuum deposition method or a sputtering method can be used. When a silver paste or the like is used, a coating method or an inkjet method can be used.
[0246] By providing an electron injection layer, the cathode can be formed using various conductive materials, regardless of the magnitude of the work function, such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, etc. These conductive materials can be deposited by sputtering, inkjet printing, spin coating, etc.
[0247] When the organic EL element is a bottom-emission type, the cathode is a light-reflective electrode. The light-reflective electrode is preferably formed of a metal material having light reflectivity. The light-reflective metal material can be appropriately selected from the materials listed in the cathode section. In addition, the light-reflective metal material may be the material listed as the metal material used for the light-reflecting layer.
[0248] When the organic EL element is a top-emission type, the cathode is a light-transmitting electrode having light-transmitting properties. The light-transmitting electrode is preferably formed of a light-transmitting or semi-transmitting metal material that transmits light emitted from the light-emitting layer. Light-transmitting or semi-transmitting means the property of transmitting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The light-transmitting or semi-transmitting metal material can be appropriately selected from the materials listed in the section on the cathode. The light-transmitting or semi-transmitting metal material may be the material listed above as the material used for the conductive layer (or transparent conductive layer).
[0249] (capping layer) A top-emission organic EL device may have a capping layer on top of the cathode, which may be disposed on the surface of the cathode opposite to the surface facing the anode. The capping layer may contain, for example, at least one compound selected from the group consisting of polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitride, and silicon compounds (such as silicon oxide). The capping layer may also contain at least one compound selected from the group consisting of, for example, aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, and dibenzofuran derivatives. Furthermore, a laminate in which two or more layers containing compounds that can be used in the capping layer are laminated can also be used as the capping layer.
[0250] (Color conversion section) The color conversion section is provided on the light extraction side of the organic EL element, and serves to convert the light extracted from the light extraction side into light of a desired color. The color conversion section is preferably disposed on the electrode (transparent electrode) of the anode and cathode that is disposed on the light extraction side. The color conversion section may be, for example, a color filter, a material containing quantum dots, or a combination of a color filter and a material containing quantum dots.
[0251] Color filters Examples of materials for the color filter include the following dyes, or solid materials in which the dyes are dissolved or dispersed in a binder resin.
[0252] Red (R) dye: A single pigment selected from the group consisting of perylene pigments, lake pigments, azo pigments, quinacridone pigments, anthraquinone pigments, anthracene pigments, isoindoline pigments, and isoindolinone pigments, or a mixture containing two or more pigments can be used.
[0253] Green (G) dye: A single product selected from the group consisting of halogen-substituted phthalocyanine pigments, halogen-substituted copper phthalocyanine pigments, triphenthane-based basic dyes, isoindoline-based pigments, and isoindolinone-based pigments, or a mixture containing two or more products can be used.
[0254] Blue (B) dye: A single pigment selected from the group consisting of copper phthalocyanine pigments, indanthrone pigments, indophenol pigments, cyanine pigments, dioxazine pigments, etc., or a mixture containing two or more pigments can be used.
[0255] It is preferable to use a transparent material as the binder resin used in the color filter material, and for example, it is preferable to use a material having a transmittance of 50% or more in the visible light region. The binder resin used in the color filter material is preferably a transparent resin (polymer), etc. The binder resin used in the color filter material is preferably one or a mixture containing two or more selected from the group consisting of polymethyl methacrylate, polyacrylate, polycarbonate, polyvinyl alcohol, polyvinylpyrrolidone, hydroxyethyl cellulose, carboxymethyl cellulose, etc.
[0256] Quantum dots Examples of materials containing quantum dots include materials in which quantum dots are dispersed in a resin, etc. The quantum dots may be at least one selected from the group consisting of CdSe, ZnSe, CdS, CdSeS / ZnS, InP, InP / ZnS, CdS / CdSe, CdS / ZnS, PbS, and CdTe.
[0257] The color conversion unit may have a red conversion region that converts blue light to red light, a green conversion region that converts blue light to green light, and a blue transmission region that transmits blue light. The color conversion unit is also preferably configured to obtain three colors of light or a mixture of these colors from the organic EL element. For example, if the blue light emitted from the first and second light-emitting layers has a narrow half-width at half maximum and high color purity, the emitted light that passes through the red conversion region is converted into red light with high color purity, and the emitted light that passes through the green conversion region is converted into green light with high color purity.
[0258] (hole injection layer) The hole injection layer is a layer containing a substance with high hole injection properties, such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, or manganese oxide.
[0259] In addition, materials with high hole injection properties include low-molecular-weight organic compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DNTPD). [N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), and other aromatic amine compounds, such as dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), are also included.
[0260] Furthermore, polymeric compounds (oligomers, dendrimers, polymers, etc.) can also be used as materials with high hole injection properties. Examples include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD). Acid-added polymeric compounds such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can also be used.
[0261] (Hole transport layer) The hole transport layer is a layer containing a substance with high hole transport properties. In the organic EL device according to this embodiment, a hole transport layer is preferably disposed between the anode and the light-emitting region, and more preferably between the anode and the first light-emitting layer.
[0262] In the organic EL device according to this embodiment, the hole transport layer preferably contains a third compound represented by the following general formula (H1) or (H2).
[0263] [ka]
[0264] (In the general formula (H1), L 31 , L 32 and L 33 are each independently, a single bond, or a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, Ar 31 , Ar32 and Ar 33 are each independently, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or -Si(R C1 )(R C2 )(R C3 ) is a group represented by R C1、 R C2 and R C3 each independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, R C1 If there are multiple R C1 are the same or different from each other, R C2 If there are multiple R C2 are the same or different from each other, R C3 If there are multiple R C3 are either identical or different.)
[0265] [ka]
[0266] (In the general formula (H2), A 41 and A 42 are each independently, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, R 410 ~R 414 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 420 ~R 424One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 410 ~R 414 and R 420 ~R 424 are each independently, hydrogen atoms, cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by halogen atoms, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, m1 is 3, and three R 410 are the same or different from each other, m2 is 3, and 3 R 420 are the same or different from each other, L 41 and L 42 are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or It is a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
[0267] (In the third compound represented by the general formula (H2), R 901 , R 902 , R 903 and R 904 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are either identical or different.)
[0268] In the organic EL device according to this embodiment, the third compound, Ar 31 , Ar 32 and Ar 33 It is also preferable that at least one of the above is a group represented by the following general formula (H1A).
[0269] [ka]
[0270] (In the general formula (H1A), X3 is an oxygen atom, a sulfur atom, or NR 319 or C(R 320 )(R 321 ) and R 311 ~R 318 A pair of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 320 and R 321 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 311 ~R 321 One of the bonds is a single bond that connects to *e, or R 311 ~R 318 a carbon atom constituting the ring skeleton of the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted fused ring formed by bonding together a pair of adjacent two or more of the above is bonded to *a by a single bond, or R 320 and R 321 a carbon atom constituting a ring skeleton of the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted fused ring formed by bonding together a pair consisting of: R that does not form the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted fused ring and is not a single bond bonded to *a 311 ~R 318 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 10 ring atoms, *R that is not a single bond attached to a 319 teeth, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, *R is not a single bond bonded to a, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring320 and R 321 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, ** indicates independently L 31 , L 32 Or L 33 or the bonding position to the nitrogen atom of the amino group.
[0271] In at least one group represented by the general formula (H1A) of the third compound, R 311 ~R 318 It is also preferred that at least one pair of adjacent two or more of the above groups be bonded to each other to form a substituted or unsubstituted monocycle or a substituted or unsubstituted fused ring.
[0272] In at least one group represented by the general formula (H1A) of the third compound, R 311 ~R 318 It is also preferred that at least one pair of adjacent two or more of the above be bonded to each other to form a substituted or unsubstituted benzene ring.
[0273] In at least one group represented by the general formula (H1A) of the third compound, R 311 ~R 318 It is also preferred that one or two pairs of adjacent two or more of the above be bonded to each other to form a substituted or unsubstituted benzene ring.
[0274] In at least one group represented by the general formula (H1A) of the third compound, R 311 ~R 318 It is also preferred that no pair of adjacent two or more of the above is bonded to each other.
[0275] In the organic EL device according to this embodiment, the third compound is a monoamine compound having one substituted or unsubstituted amino group in the molecule; a diamine compound having two substituted or unsubstituted amino groups in the molecule; a triamine compound having three substituted or unsubstituted amino groups in the molecule, and It is also preferable that the amine compound is at least one selected from the group consisting of tetraamine compounds having four substituted or unsubstituted amino groups in the molecule.
[0276] In the organic EL device according to this embodiment, the third compound is preferably at least one amine compound selected from the group consisting of monoamine compounds and diamine compounds.
[0277] In the organic EL device according to this embodiment, the third compound is also preferably a monoamine compound.
[0278] In the organic EL device according to this embodiment, the hole transport layer can be made of an aromatic amine compound, a carbazole derivative, an anthracene derivative, etc. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl ... Aromatic amine compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) can be used. The substances mentioned here are mainly 10 -6 cm 2 A material with a hole mobility of at least / (V·s).
[0279] The hole transport layer may be made of carbazole derivatives such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (PCzPA), or anthracene derivatives such as t-BuDNA, DNA, and DPAnth. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) may also be used.
[0280] However, other substances may be used as long as they have a higher hole-transporting property than an electron-transporting property. Note that the layer containing the substance having a high hole-transporting property may be not only a single layer, but also a stack of two or more layers containing the above-mentioned substances.
[0281] (electron barrier layer) The electron blocking layer is preferably a layer that transports holes and prevents electrons from reaching a layer (e.g., a hole transport layer) closer to the anode than the electron blocking layer. The compound contained in the electron blocking layer is, for example, a compound used in known electron blocking layers, and is preferably at least one compound selected from the group consisting of aromatic amine compounds and carbazole derivatives. The compound contained in the electron blocking layer may also be a monoamine compound having only one substituted or unsubstituted amino group in the molecule. The compound contained in the electron blocking layer may also be a compound having a substituted or unsubstituted carbazolyl group and one substituted or unsubstituted amino group in the molecule. The electron blocking layer may be a layer that prevents excitons generated in the light-emitting layer from migrating to a layer closer to the anode than the electron blocking layer (e.g., a hole transport layer and a hole injection layer) so that excitation energy does not leak from the light-emitting layer to a peripheral layer.
[0282] (hole blocking layer) The hole blocking layer is preferably a layer that transports electrons and prevents holes from reaching a layer (e.g., an electron transport layer) closer to the cathode than the hole blocking layer. The compound contained in the hole blocking layer is, for example, a compound used in known hole blocking layers. The compound contained in the hole blocking layer is preferably at least one compound selected from the group consisting of metal complexes, heteroaromatic compounds, and polymer compounds, similar to the compounds that can be used in the electron transport layer described below. The compound contained in the hole blocking layer may also be, for example, at least one compound selected from the group consisting of imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives. It is also preferable that the hole blocking layer is a layer that prevents excitons generated in the light-emitting layer from migrating to a layer closer to the cathode than the hole blocking layer (for example, an electron transport layer or an electron injection layer) so that excitation energy does not leak from the light-emitting layer to a peripheral layer.
[0283] (electron transport layer) The electron transport layer is a layer containing a substance with a high electron transport property. In the organic EL device according to this embodiment, an electron transport layer is preferably disposed between the light-emitting region and the cathode, and more preferably between the second light-emitting layer and the cathode.
[0284] In the organic EL device according to this embodiment, the electron transport layer preferably contains a fourth compound represented by the following general formula (E1).
[0285] [ka]
[0286] (In the general formula (E1), X 51 , X 52 and X 53 are each independently a nitrogen atom or CR5, However, X 51, X 52 and X 53 at least one of which is a nitrogen atom, R5 is hydrogen atoms, cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, Ax is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms, Bx is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms, L5 is single bond, a substituted or unsubstituted (n+1)-valent aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted (n+1)-valent heterocyclic group having 5 to 13 ring atoms, n is 1, 2 or 3, and when n is 2 or 3, L5 is not a single bond, Cx is independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 60 ring atoms, When there are multiple Cx, the multiple Cx may be the same or different.
[0287] (In the fourth compound, R 901 , R 902 , R903 and R 904 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are either identical or different.)
[0288] In the organic EL device according to this embodiment, X of the fourth compound 51 , X 52 and X 53 Among these, it is preferred that two or three are nitrogen atoms.
[0289] In the organic EL device according to this embodiment, the fourth compound is preferably a compound represented by the following general formula (E11), (E12), (E13) or (E14).
[0290] [ka]
[0291] (In the general formulae (E11) to (E14), Ax, Bx, Cx, R5, L5 and n are each as defined in the general formula (E1).)
[0292] In the organic EL device according to this embodiment, the electron transport layer may be formed using 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.Specific examples of low-molecular-weight organic compounds that may be used include 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. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: Heteroaromatic compounds such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), bathophenanthroline (abbreviated as BPhen), bathocuproine (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviated as BzOs) can also be used. In this embodiment, benzimidazole compounds can be preferably used. The substances mentioned here are mainly 10 -6 cm 2 / (V·s) or more. Note that other substances may be used as the electron-transporting layer as long as they have a higher electron-transporting property than a hole-transporting property. The electron-transporting layer may be formed as a single layer or as a stack of two or more layers made of the above-mentioned substances.
[0293] The electron transport layer can also be made of a polymer compound, such as poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) or poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).
[0294] (electron injection layer) The electron injection layer is a layer containing a substance with high electron injection properties. In the organic EL device according to this embodiment, the electron injection layer can be made of an alkali metal, alkaline earth metal, or compound thereof, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF), or lithium oxide (LiOx). Alternatively, an electron-transporting substance containing an alkali metal, alkaline earth metal, or compound thereof, such as magnesium (Mg) in Alq, can be used. In this case, electrons can be injected from the cathode more efficiently.
[0295] Alternatively, the electron injection layer may be formed using a composite material obtained by mixing an organic compound and an electron donor (donor). Such composite materials have excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material that is excellent at transporting the generated electrons. Specifically, for example, the above-mentioned substances constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) can be used. The electron donor may 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 (TTF) can also be used.
[0296] (Layer formation method) The method for forming each layer of the organic EL element of this embodiment is not limited to those specifically mentioned above, but known methods can be used, such as dry film formation methods such as vacuum deposition, sputtering, plasma deposition, and ion plating, and wet film formation methods such as spin coating, dipping, flow coating, and inkjet deposition.
[0297] (film thickness) The thickness of each organic layer in the organic EL device of this embodiment is not limited unless otherwise specified above. Generally, if the thickness is too thin, defects such as pinholes are likely to occur, and if the thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, the thickness of each organic layer in the organic EL device is usually preferably in the range of several nm to 1 μm.
[0298] (Emission wavelength of organic EL element) The organic electroluminescent element according to this embodiment preferably emits light having a maximum peak wavelength of 500 nm or less when the element is in operation. The organic electroluminescent element according to this embodiment preferably emits light having a maximum peak wavelength of 430 nm or more and 480 nm or less when the element is driven. The maximum peak wavelength of light emitted from the organic EL element when the element is driven is measured as follows: 2 A voltage is applied to the organic EL element so that the spectral radiance spectrum is measured using a spectroradiometer CS-2000 (Konica Minolta, Inc.) In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is measured and this is defined as the maximum peak wavelength (unit: nm).
[0299] (First Host Material) In the organic EL device according to this embodiment, the first host material is not particularly limited, and examples thereof include a compound represented by the following general formula (H11), a compound represented by the general formula (H12), a compound represented by the general formula (H13), a compound represented by the general formula (H14), a compound represented by the general formula (H15), and a compound represented by the general formula (H16).
[0300] <First compound> In one aspect of the organic EL device according to this embodiment, the first host material is preferably a first compound selected from the group consisting of compounds represented by the following general formula (H11), compounds represented by the general formula (H12), compounds represented by the general formula (H13), compounds represented by the general formula (H14), compounds represented by the general formula (H15), and compounds represented by the general formula (H16).
[0301] (Compound represented by general formula (H11)) The compound represented by general formula (H11) will be explained.
[0302] [ka]
[0303] (In the general formula (H11), R 101 ~R 110 , and R 111 ~R 120 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, However, R 101 ~R 110 One of them is L 101 indicates the bond position with R 111 ~R 120 One of them is L 101 indicates the bonding position with L 101 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 24 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 24 ring atoms, mx is 0, 1, 2, 3, 4 or 5; L 101 If there are two or more, there are two or more L 101 are either identical or different.)
[0304] (In the first compound, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 906 If there are multiple R 906 are the same or different from each other, R 907 If there are multiple R 907 are the same or different from each other, R 801If there are multiple R 801 are the same or different from each other, R 802 If there are multiple R 802 are either identical or different.)
[0305] In one aspect of the organic EL device according to this embodiment, the compound represented by general formula (H11) is a compound represented by the following general formula (H111).
[0306] [ka]
[0307] (In the general formula (H111), R 101 , R 102 , R 104 ~R 110 , and R 111 ~R 119 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L 101 and mx respectively represent L in the general formula (H11). 101 and mx.)
[0308] In one aspect of the organic EL element according to this embodiment, mx is 1 or 2.
[0309] In one aspect of the organic EL element according to this embodiment, L 101 represents a substituted or unsubstituted arylene group having 6 to 24 ring carbon atoms.
[0310] In one aspect of the organic EL device according to this embodiment, the first compound is a compound having only two pyrene rings in the molecule (sometimes referred to as a bispyrene compound). In one aspect of the organic EL device according to this embodiment, the compound represented by the general formula (H11) is a bispyrene compound.
[0311] (Compound represented by general formula (H12)) The compound represented by general formula (H12) will be explained.
[0312] [ka]
[0313] (In the general formula (H12), Xa is an oxygen atom, a sulfur atom, or a C(R 1201 )(R 1202 ), or Si(R 1203 )(R 1204 ) and R 1201 ~R 1204 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 121 ~R 130 At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 121 ~R 130 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the general formula (H121), However, R 121 ~R 130 at least one of is a group represented by general formula (H121) above, When a plurality of groups represented by the general formula (H121) are present, the plurality of groups represented by the general formula (H121) are the same or different from each other, L 12 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, ma is 0, 1, 2 or 3; L 12 If there are two or more, there are two or more L 12 are identical to or different from each other, Ar 12 represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, Ar 12 If there are two or more, there are two or more Ar 12 are identical to or different from each other, In the general formula (H121), * indicates the bonding position.
[0314] In one aspect of the organic EL element of this embodiment, L 12 represents a single bond, a substituted or unsubstituted arylene group having 6 to 15 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 15 ring atoms.
[0315] In one aspect of the organic EL element according to this embodiment, Ar 12 is a substituted or unsubstituted aryl group containing four or more rings or a substituted or unsubstituted heterocyclic group containing four or more rings.
[0316] In one aspect of the organic EL element according to this embodiment, Ar 12 is a substituted or unsubstituted aryl group containing four or more rings.
[0317] In one aspect of the organic EL element according to this embodiment, R 129 is a group represented by the general formula (H121).
[0318] In one aspect of the organic EL device according to this embodiment, Xa is an oxygen atom.
[0319] In one aspect of the organic EL device according to this embodiment, the compound represented by the general formula (H12) is a compound represented by the following general formula (H122).
[0320] [ka]
[0321] (In the general formula (H122), R 121 ~R 128 and R 130 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, Ar 12 , L 12 and ma each represent Ar in the general formula (H121). 12 , L 12 and ma).
[0322] In one aspect of the organic EL device according to this embodiment, ma is 1 or 2.
[0323] (Compound represented by general formula (H13)) The compound represented by general formula (H13) will be explained.
[0324] [ka]
[0325] (In the general formula (H13), R131 ~R 140 , Ar 131 and Ar 132 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by general formula (H131), However, R 131 ~R 140 , Ar 131 and Ar 132 at least one of is a group represented by general formula (H131) above, When a plurality of groups represented by the general formula (H131) are present, the plurality of groups represented by the general formula (H131) are the same or different from each other, L 13 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, Ar 13 teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mb is 0, 1, 2, 3, 4 or 5; L 13 If there are two or more, there are two or more L 13 are identical to or different from each other, Ar 13 If there are two or more, there are two or more Ar 13 are identical to or different from each other, In the general formula (H131), * indicates the bonding position to the benz[a]anthracene ring in the general formula (H13).
[0326] In one aspect of the organic EL element according to this embodiment, Ar 131 and Ar 132 At least one of these is a group represented by general formula (H131).
[0327] In one aspect of the organic EL device according to this embodiment, the compound represented by the general formula (H13) is a compound represented by the following general formula (H132) or (H133).
[0328] [ka]
[0329] (In the general formulae (H132) and (H133), R 131 ~R 140 , Ar 131 and Ar 132 are, respectively, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L 13 , Ar 13 and mb respectively represent L in the general formula (H131). 13 , Ar 13 and mb.)
[0330] In one aspect of the organic EL device according to this embodiment, mb is 0, 1, or 2.
[0331] (Compound represented by general formula (H14)) The compound represented by general formula (H14) will be explained.
[0332] [ka]
[0333] (In the general formula (H14), R 1A and R 1B are each independently, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 17 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 17 ring atoms, However, R 1A and R 1B at least one of the groups is a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, R 141 ~R 144 A pair of two or more adjacent 145 ~R 148 Any one of the pairs of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, The group represented by the general formula (H141) is When a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring is formed on the ring A side, R 142 or, among the carbon atoms constituting the monocyclic ring on the ring A side and the fused ring on the ring A side, the carbon atom C1 of ring A is bonded to the carbon atom C2 on the ring B side by a single bond, which is the farthest from the carbon atom C1 of ring A, When a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring is not formed on the ring A side but is formed on the ring B side, R 142 Attached to a carbon atom attached to R that is not a group represented by general formula (H141) 142 R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 141 , R 143 , R 144 and R 145 ~R 148 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 17 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 17 ring atoms, In the general formula (H141), Ar 14 is a substituted or unsubstituted aryl group having four or more fused rings or a substituted or unsubstituted heterocyclic group having four or more fused rings, L 14 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 17 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 17 ring atoms, mc is 0, 1 or 2; * indicates the bonding position to an atom constituting the ring of general formula (H14), However, the compound represented by the general formula (H14) does not contain three or more substituted or unsubstituted aryl groups having four or more fused rings and three or more substituted or unsubstituted heterocyclic groups having four or more fused rings in the molecule of the compound represented by the general formula (H14).
[0334] In one aspect of the organic EL element according to this embodiment, R 142 is a group represented by the general formula (H141).
[0335] In one aspect of the organic EL device according to this embodiment, in the compound represented by general formula (H14), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 17 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 17 ring atoms.
[0336] In one aspect of the organic EL device according to this embodiment, the compound represented by the general formula (H14) is a compound represented by the following general formula (H142), general formula (H143), or general formula (H144).
[0337] [ka]
[0338] [ka]
[0339] (In the general formula (H142), general formula (H143) or general formula (H144), R 1A , R 1B , R 141, R 143 , R 144 , R 145 , R 146 , R 147 and R 148 respectively represent R in the general formula (H14). 1A , R 1B , R 141 , R 143 , R 144 , R 145 , R 146 , R 147 and R 148 is synonymous with Ar 14 , L 14 and mc are each Ar in the general formula (H141). 14 , L 14 and mc, R 1401 ~R 1404 one or more pairs of adjacent pairs of R 1401 ~R 1404 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 17 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 17 ring atoms.
[0340] In one aspect of the organic EL device according to this embodiment, mc is 0, 1, or 2.
[0341] (Compound represented by general formula (H15)) The compound represented by general formula (H15) will be explained.
[0342] [ka]
[0343] (In the general formula (H15), R 150 ~R 159 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the general formula (H150), However, R 150 ~R 159 at least one of is a group represented by general formula (H150) above, When a plurality of groups represented by the general formula (H150) are present, the plurality of groups represented by the general formula (H150) are the same or different from each other, L 151 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, Ar 151 teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mg is 0, 1, 2, 3, 4 or 5; L 151 If there are two or more, there are two or more L 151 are identical to or different from each other, Ar 151 If there are two or more, there are two or more Ar 151 are identical to or different from each other, In the general formula (H150), * indicates the bonding position to the pyrene ring in the general formula (H15).
[0344] In one aspect of the organic EL device according to this embodiment, R 153 is a group represented by the general formula (H150).
[0345] In one aspect of the organic EL element according to this embodiment, L 151 is a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, and Ar 151 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0346] In one aspect of the organic EL element according to this embodiment, L 151 is a single bond or a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms, and Ar 151 is a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms.
[0347] In one aspect of the organic EL device according to this embodiment, the group represented by the general formula (H150) is a group represented by the following general formula (H151).
[0348] [ka]
[0349] (In the general formula (H151), X 15 is an oxygen atom or a sulfur atom, L 15 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, md is 0, 1, 2, 3, 4 or 5; L 15 If there are two or more, there are two or more L 15 are identical to or different from each other, R 1500 ~R 1504 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 1500 ~R 1504 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, Multiple R 1500 are the same or different from each other, When a plurality of groups represented by the general formula (H151) are present, the plurality of groups represented by the general formula (H151) are the same or different from each other, In the general formula (H151), * indicates the bonding position to the pyrene ring in the general formula (H15).
[0350] In one aspect of the organic EL device according to this embodiment, the compound represented by the general formula (H15) is a compound represented by the following general formula (H152): 153 When is a group represented by the general formula (H151), it is represented by the following general formula (H152).
[0351] [ka]
[0352] (In the general formula (H152), R 150 ~R 152 and R 154 ~R 159 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, X 15 , L 15 and md respectively represent X in the general formula (H151). 15 , L 15 and md, R 1500 ~R 1504 each independently represents R in general formula (H151). 1500 ~R 1504 is equivalent to
[0353] In one aspect of the organic EL device according to this embodiment, md is 0, 1, or 2. In one aspect of the organic EL device according to this embodiment, when md is 0, the compound represented by general formula (H152) is represented by the following general formula (H153).
[0354] [ka]
[0355] (In the general formula (H153), R 150 ~R 152 , R 154 ~R 159 , R 1500 ~R 1504 , and X 15 respectively represent R in the general formula (H152). 150 ~R 152 , R 154 ~R 159 , R 1500 ~R 1504 , and X 15 is equivalent to
[0356] In one aspect of the organic EL device according to this embodiment, the first compound is a compound having only one pyrene ring in the molecule (sometimes referred to as a monopyrene compound). In one aspect of the organic EL device according to this embodiment, the compound represented by the general formula (H15) is a monopyrene compound.
[0357] (Compound represented by general formula (H16)) The compound represented by general formula (H16) will be explained.
[0358] [ka]
[0359] (In the general formula (H16), R 160 ~R 169 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 160 ~R 169 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by general formula (H161), However, when the substituted or unsubstituted monocyclic ring has a substituent, the substituent when the substituted or unsubstituted fused ring has a substituent, and R 160 ~R 169 at least one of the above is a group represented by general formula (H161), When a plurality of groups represented by the general formula (H161) are present, the plurality of groups represented by the general formula (H161) are the same or different from each other, L 16 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, Ar 16 teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mf is 0, 1, 2, 3, 4 or 5; L 16 If there are two or more, there are two or more L 16 are identical to or different from each other, Ar 16 If there are two or more, there are two or more Ar 16 are identical to or different from each other, In the general formula (H161), * indicates the bonding position to the ring represented by the general formula (H16).
[0360] In one aspect of the organic EL device according to this embodiment, the first compound is a compound represented by the following general formula (H162).
[0361] [ka]
[0362] (In the general formula (H162), R 161 ~R 167 and R 1601 ~R 1604 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, Ar 16 , L 16 and mf respectively represent Ar in the general formula (H16). 16 , L 16 and mf.)
[0363] In one aspect of the organic EL device according to this embodiment, mf is 0, 1, or 2.
[0364] In one aspect of the organic EL element according to this embodiment, it is preferable that the first compounds are each independently any compound selected from the group consisting of compounds represented by general formula (H111), compounds represented by general formula (H122), compounds represented by general formula (H132), and compounds represented by general formula (H133).
[0365] In one aspect of the organic EL device according to this embodiment, the first compound preferably does not have a bis-carbazole structure or an amine structure in the molecule.
[0366] In one aspect of the organic EL device according to this embodiment, the first compound does not contain a compound having a bis-carbazole structure or a compound having an amine structure.
[0367] In one aspect of the organic EL device according to this embodiment, all of the groups described as "substituted or unsubstituted" in the first compound are "unsubstituted" groups.
[0368] In the organic EL device according to this embodiment, it is also preferable that the first host material has a linking structure in the molecule including a benzene ring and a naphthalene ring linked by a single bond, and that the benzene ring and the naphthalene ring in the linking structure are each independently further fused with a single ring or a fused ring, or are not fused with a single ring or a fused ring, and that the benzene ring and the naphthalene ring in the linking structure are further linked by a crosslink at at least one portion other than the single bond. When the first host material has a linking structure including such a crosslink, it is expected that deterioration of the chromaticity of the organic EL device can be suppressed. In this case, the first host material only needs to have, as a minimum unit in the molecule, a linked structure containing a benzene ring and a naphthalene ring linked by a single bond, as represented by the following formula (X1) or (X2) (sometimes referred to as a benzene-naphthalene linked structure), and the benzene ring may be further fused with a single ring or a fused ring, or the naphthalene ring may be further fused with a single ring or a fused ring. For example, even when the first host material has, in the molecule, a linked structure containing a naphthalene ring and a naphthalene ring linked by a single bond, as represented by the following formula (X3), (X4), or (X5) (sometimes referred to as a naphthalene-naphthalene linked structure), one of the naphthalene rings contains a benzene ring, and therefore contains a benzene-naphthalene linked structure.
[0369] [ka]
[0370] In the organic EL device according to this embodiment, it is also preferable that the crosslink contains a double bond, i.e., the benzene ring and the naphthalene ring are further linked by a crosslinked structure containing a double bond at a portion other than the single bond.
[0371] When the benzene ring and the naphthalene ring in the benzene-naphthalene linked structure are further linked by a bridge at at least one portion other than a single bond, for example, in the case of the formula (X1), the linked structure (fused ring) is represented by the following formula (X11), and in the case of the formula (X3), the linked structure (fused ring) is represented by the following formula (X31). When the benzene ring and the naphthalene ring in the benzene-naphthalene linked structure are further linked by a bridge containing a double bond at a portion other than the single bond, for example, in the case of the formula (X1), the linked structure (fused ring) is represented by the following formula (X12); in the case of the formula (X2), the linked structure (fused ring) is represented by the following formula (X21) or formula (X22); in the case of the formula (X4), the linked structure (fused ring) is represented by the following formula (X41); and in the case of the formula (X5), the linked structure (fused ring) is represented by the following formula (X51). When the benzene ring and the naphthalene ring in the benzene-naphthalene linked structure are further linked by a bridge containing a heteroatom (e.g., an oxygen atom) in at least one portion other than the single bond, for example, in the case of the above formula (X1), the linked structure (fused ring) is represented by the following formula (X13).
[0372] [ka]
[0373] In the organic EL device according to this embodiment, it is also preferable that the first host material has a biphenyl structure in which a first benzene ring and a second benzene ring are linked by a single bond in the molecule, and that the first benzene ring and the second benzene ring in the biphenyl structure are further linked by a bridge at at least one portion other than the single bond.
[0374] In the organic EL device according to this embodiment, it is also preferable that the first benzene ring and the second benzene ring in the biphenyl structure are further connected by the bridge at a portion other than the single bond. When the first host material has a biphenyl structure including such a bridge, deterioration in chromaticity of the organic EL device can be expected to be suppressed.
[0375] In the organic EL device according to this embodiment, it is also preferable that the crosslink contains a double bond. In the organic EL device according to this embodiment, it is also preferable that the crosslink does not contain a double bond.
[0376] It is also preferred that the first and second benzene rings in the biphenyl structure are further linked by the bridge at two sites other than the single bond.
[0377] In the organic EL device according to this embodiment, it is also preferable that the first and second benzene rings in the biphenyl structure are further connected by the bridge at two positions other than the single bond, and the bridge does not contain a double bond. When the first host material has a biphenyl structure including such a bridge, it is expected that deterioration in chromaticity of the organic EL device can be suppressed.
[0378] For example, when the first benzene ring and the second benzene ring in the biphenyl structure represented by the following formula (BP1) are further linked by a bridge at at least one moiety other than a single bond, the biphenyl structure becomes a linked structure (fused ring) such as those of the following formulae (BP11) to (BP15).
[0379] [ka]
[0380] The formula (BP11) is a structure in which the units are linked by a bridge that does not contain a double bond in one part other than the single bond. The formula (BP12) is a structure in which the units are linked by a bridge containing a double bond in one part other than the single bond. The formula (BP13) has a structure in which the two parts other than the single bond are linked by a bridge that does not contain a double bond. The formula (BP14) has a structure in which one of the two moieties other than the single bond is linked by a bridge that does not contain a double bond, and the other of the two moieties other than the single bond is linked by a bridge that contains a double bond. The formula (BP15) has a structure in which the two moieties other than the single bond are linked by a bridge containing a double bond.
[0381] In the first compound and the second compound, it is preferable that the groups described as "substituted or unsubstituted" are both "unsubstituted" groups.
[0382] (Method for producing the first compound) The first compound can be produced by a known method. Alternatively, the first compound can be produced by following a known method and using known alternative reactions and raw materials suited to the target compound.
[0383] (Specific Examples of the First Compound) Specific examples of the first compound include the following compounds, however, the present invention is not limited to these specific examples of the first compound. In the present specification, in specific examples of compounds, D represents a deuterium atom, Me represents a methyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.
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[0525] (Second Host Material) In one aspect of the organic EL device according to this embodiment, the second host material is preferably a second compound. In the organic EL device according to this embodiment, the second host material is not particularly limited, but examples thereof include a second compound represented by the following general formula (2):
[0526] <Second Compound> In the organic EL device according to this embodiment, the second compound is preferably a compound represented by the following general formula (2): The second host material is preferably a second compound represented by the following general formula (2).
[0527] (Compound represented by general formula (2)) The compound represented by general formula (2) will be explained.
[0528] [ka]
[0529] (In the general formula (2), R 201 ~R 208 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L 201 and L 202 are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, Ar 201 and Ar 202 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0530] In the second compound, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 906 If there are multiple R 906 are the same or different from each other, R 907If there are multiple R 907 are the same or different from each other, R 801 If there are multiple R 801 are the same or different from each other, R 802 If there are multiple R 802 are the same or different from each other.
[0531] In the organic EL element according to this embodiment, R 201 ~R 208 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, a cyano group, or is a nitro group, L 201 and L 202 are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, Ar 201 and Ar 202 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0532] In the organic EL element according to this embodiment, L 201 and L 202 are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, and Ar 201 and Ar 202 are preferably each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0533] In the organic EL element according to this embodiment, Ar 201 and Ar 202 are preferably each independently a phenyl group, a naphthyl group, a phenanthryl group, a biphenyl group, a terphenyl group, a diphenylfluorenyl group, a dimethylfluorenyl group, a benzodiphenylfluorenyl group, a benzodimethylfluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, a naphthobenzofuranyl group, or a naphthobenzothienyl group.
[0534] In the organic EL device according to this embodiment, the second compound represented by the general formula (2) is preferably a compound represented by the following general formula (201), general formula (202), general formula (203), general formula (204), general formula (205), general formula (206), general formula (207), general formula (208), or general formula (209).
[0535] [ka]
[0536] [ka]
[0537] [ka]
[0538] [ka]
[0539] [ka]
[0540] [ka]
[0541] [ka]
[0542] [ka]
[0543] [ka]
[0544] (In the general formulas (201) to (209), L 201 and Ar 201 is L in the general formula (2). 201 and Ar 201 is synonymous with R 201 ~R 208 are each independently R in the general formula (2). 201 ~R 208 is equivalent to
[0545] The second compound represented by the general formula (2) is also preferably a compound represented by the following general formula (221), general formula (222), general formula (223), general formula (224), general formula (225), general formula (226), general formula (227), general formula (228), or general formula (229).
[0546] [ka]
[0547] [ka]
[0548] [ka]
[0549] [ka]
[0550] [ka]
[0551] [ka]
[0552] [ka]
[0553] [ka]
[0554] [ka]
[0555] (In the general formula (221), the general formula (222), the general formula (223), the general formula (224), the general formula (225), the general formula (226), the general formula (227), the general formula (228) and the general formula (229), R 201 and R 203 ~R 208 are each independently R in the general formula (2). 201 and R 203 ~R 208 is synonymous with L 201 and Ar 201 respectively represent L in the general formula (2). 201 and Ar 201 is synonymous with L 203 is L in the general formula (2). 201 is synonymous with L 203 and L 201 are identical to or different from each other, Ar 203 represents Ar in the general formula (2). 201 is synonymous with Ar 203 and Ar 201 are either identical or different.)
[0556] The second compound represented by the general formula (2) is also preferably a compound represented by the following general formula (241), general formula (242), general formula (243), general formula (244), general formula (245), general formula (246), general formula (247), general formula (248), or general formula (249).
[0557] [ka]
[0558] [ka]
[0559] [ka]
[0560] [ka]
[0561] [ka]
[0562] [ka]
[0563] [ka]
[0564] [ka]
[0565] [ka]
[0566] (In the general formula (241), the general formula (242), the general formula (243), the general formula (244), the general formula (245), the general formula (246), the general formula (247), the general formula (248) and the general formula (249), R 201 , R 202 and R 204 ~R 208 are each independently R in the general formula (2). 201 , R 202 and R 204 ~R 208 is synonymous with L 201 and Ar 201 respectively represent L in the general formula (2). 201 and Ar 201 is synonymous with L203 is L in the general formula (2). 201 is synonymous with L 203 and L 201 are identical to or different from each other, Ar 203 represents Ar in the general formula (2). 201 is synonymous with Ar 203 and Ar 201 are either identical or different.)
[0567] In the second compound represented by the general formula (2), R 201 ~R 208 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or —Si(R 901 )(R 902 )(R 903 ) is preferably a group represented by the formula (I).
[0568] L 201 is a single bond or an unsubstituted arylene group having 6 to 22 ring carbon atoms, and Ar 201 is preferably a substituted or unsubstituted aryl group having 6 to 22 ring carbon atoms.
[0569] In the organic EL device according to this embodiment, in the second compound represented by the general formula (2), R 201 ~R 208 is preferably a hydrogen atom in order to prevent the suppression of intermolecular interactions and the decrease in electron mobility. 201 ~R 208 may be a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R 201 ~R 208When the second compound is a bulky substituent such as an alkyl group or a cycloalkyl group, the intermolecular interaction is suppressed, the electron mobility with respect to the first host material is reduced, and the relationship μe(H2)>μe(H1) in the above formula (70) may not be satisfied. When the second compound is used in the second emitting layer, satisfying the relationship μe(H2)>μe(H1) is expected to suppress a decrease in the recombination ability of holes and electrons in the first emitting layer and a decrease in luminous efficiency. The substituent may be a haloalkyl group, an alkenyl group, an alkynyl group, -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 ), an aralkyl group, -C(=O)R 801 a group represented by -COOR 802 The group represented by the formula (I), the halogen atom, the cyano group, and the nitro group may be bulky, and the alkyl group and the cycloalkyl group may be even more bulky. In the second compound represented by the general formula (2), R 201 ~R 208 is preferably not a bulky substituent, is preferably not an alkyl group or a cycloalkyl group, and is preferably not an alkyl group, a cycloalkyl group, a haloalkyl group, an alkenyl group, an alkynyl group, -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 ), an aralkyl group, -C(=O)R 801 a group represented by -COOR 802 It is more preferable that the aryl group is not a group represented by the formula (I), a halogen atom, a cyano group, or a nitro group.
[0570] In the organic EL device according to this embodiment, in the second compound represented by the general formula (2), R201 ~R 208 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or —Si(R 901 )(R 902 )(R 903 ) is also preferred.
[0571] In the organic EL device according to this embodiment, in the second compound represented by the general formula (2), R 201 ~R 208 is preferably a hydrogen atom.
[0572] In the second compound, R 201 ~R 208 It is also preferable that the substituent in the case of "substituted or unsubstituted" does not include the above-mentioned potentially bulky substituents, particularly substituted or unsubstituted alkyl groups and substituted or unsubstituted cycloalkyl groups. 201 ~R 208 In the case of "substituted or unsubstituted" in the above, the substituent does not include a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group, so that suppression of intermolecular interactions due to the presence of bulky substituents such as alkyl groups and cycloalkyl groups can be prevented, and a decrease in electron mobility can be prevented. Furthermore, when such a second compound is used in the second light-emitting layer, a decrease in the recombination ability of holes and electrons in the first light-emitting layer and a decrease in luminous efficiency can be suppressed.
[0573] R, a substituent of the anthracene skeleton 201 ~R 208 R is not a bulky substituent, but rather a substituent 201 ~R 208 It is more preferable that R is unsubstituted. 201 ~R 208 is not a bulky substituent, R as a non-bulky substituent 201 ~R 208When a substituent is bonded to R, the substituent is preferably not a bulky substituent. 201 ~R 208 The substituent bonded to is preferably not an alkyl group or a cycloalkyl group, and is preferably an alkyl group, a cycloalkyl group, a haloalkyl group, an alkenyl group, an alkynyl group, or —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 ), an aralkyl group, -C(=O)R 801 a group represented by -COOR 802 It is more preferable that the aryl group is not a group represented by the formula (I), a halogen atom, a cyano group, or a nitro group.
[0574] In the second compound, any group described as "substituted or unsubstituted" is preferably an "unsubstituted" group.
[0575] (Method for producing the second compound) The second compound can be produced by a known method. Alternatively, the second compound can be produced by following a known method and using known alternative reactions and raw materials suited to the target compound.
[0576] (Specific Example of the Second Compound) Specific examples of the second compound include the following compounds. However, the present invention is not limited to these specific examples of the second compound. In the following specific examples, D represents a deuterium atom.
[0577] [ka]
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[0607] (luminescent compounds) <Third Compound> In one aspect of the organic EL device according to this embodiment, the first light-emitting compound and the second light-emitting compound may be the same or different from each other. In one aspect of the organic EL device according to this embodiment, the first light-emitting compound and the second light-emitting compound are preferably the same as each other.
[0608] In one aspect of the organic EL device according to this embodiment, the light-emitting compounds such as the first light-emitting compound and the second light-emitting compound are not particularly limited, but are preferably the third compound. The third compound is also preferably, for example, independently one or more compounds selected from the group consisting of a compound represented by the following general formula (4), a compound represented by the following general formula (5), and a compound represented by the following general formula (6).
[0609] (Compound represented by general formula (4)) The compound represented by general formula (4) will be explained.
[0610] [ka]
[0611] (In the general formula (4), Each Z is independently CRa or a nitrogen atom; Ring A1 and ring A2 each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, When there are a plurality of Ra, one or more pairs of adjacent two or more of the plurality of Ra are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, n21 and n22 each independently represent 0, 1, 2, 3, or 4; When a plurality of Rb's are present, one or more pairs of adjacent two or more Rb's are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, When there are a plurality of Rc's, one or more pairs of adjacent two or more Rc's are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, Ra, Rb, and Rc which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring each independently represent a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0612] In the third compound, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 906 If there are multiple R 906 are the same or different from each other, R 907 If there are multiple R 907 are the same or different from each other, R 801 If there are multiple R 801 are the same or different from each other, R 802 If there are multiple R 802 are the same or different from each other.
[0613] (Specific examples of compounds represented by formula (4)) Specific examples of the compound represented by the general formula (4) include the compounds shown below: In the specific examples below, Ph represents a phenyl group, and D represents a deuterium atom.
[0614] [ka]
[0615] [ka]
[0616] [ka]
[0617] [ka]
[0618] [ka]
[0619] [ka]
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[0624] (Compound represented by general formula (5)) The compound represented by general formula (5) will be explained.
[0625] [ka]
[0626] (In the general formula (5), R 501 ~R 507 and R 511 ~R 517 At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 521 , R 522 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 501 ~R 507 and R 511 ~R 517 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0627] (Specific examples of compounds represented by formula (5)) Specific examples of the compound represented by the general formula (5) include the compounds shown below.
[0628] [ka]
[0629] [ka]
[0630] [ka]
[0631] [ka]
[0632] [ka]
[0633] [ka]
[0634] [ka]
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[0644] (Compound represented by general formula (6)) The compound represented by general formula (6) will be explained below: The second light-emitting compound is preferably a compound represented by the following general formula (6).
[0645] [ka]
[0646] (In the general formula (6), Ring a, ring b and ring c each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, R 601 and R 602each independently bond to the ring a, the ring b, or the ring c to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle, R that does not form the substituted or unsubstituted heterocycle 601 and R 602 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0647] At least one of the ring a, the ring b, and the ring c is —N(R 6A )(R 6B ) and has one or more groups represented by R 6A and R 6B are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 6A If there are two or more, there are two or more R 6A are identical to or different from each other, R 6B If there are two or more, there are two or more R 6B are preferably the same as or different from each other.
[0648] The rings a, b, and c are rings (substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring carbon atoms, or substituted or unsubstituted heterocyclic rings having 5 to 50 ring atoms) fused to the central fused bicyclic structure of the general formula (6) composed of a boron atom and two nitrogen atoms.
[0649] The "aromatic hydrocarbon rings" of rings a, b, and c have the same structure as the compounds in which a hydrogen atom has been introduced into the above-mentioned "aryl group." The "aromatic hydrocarbon ring" of ring a contains the three carbon atoms on the central fused two-ring structure of the general formula (6) as ring-forming atoms. The "aromatic hydrocarbon ring" of ring b and ring c contains the two carbon atoms on the central fused two-ring structure of general formula (6) as ring-forming atoms.
[0650] Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms" include compounds in which a hydrogen atom has been introduced into the "aryl group" described in specific example group G1. The "heterocycles" of ring a, ring b, and ring c have the same structure as the compounds in which a hydrogen atom has been introduced into the above-mentioned "heterocyclic group." The "heterocycle" of ring a contains three carbon atoms on the central fused bicyclic structure of general formula (6) as ring-forming atoms. The "heterocycle" of rings b and c contains two carbon atoms on the central fused bicyclic structure of general formula (6) as ring-forming atoms. Specific examples of "substituted or unsubstituted heterocycles having 5 to 50 ring atoms" include compounds in which a hydrogen atom has been introduced into the "heterocyclic group" described in specific example group G2.
[0651] R 601 and R 602 may each independently bond to ring a, ring b, or ring c to form a substituted or unsubstituted heterocyclic ring. In this case, the heterocyclic ring contains the nitrogen atom on the central fused bicyclic structure of the general formula (6). In this case, the heterocyclic ring may contain a heteroatom other than the nitrogen atom. R 601 and R 602 is bonded to ring a, ring b, or ring c specifically means that an atom constituting ring a, ring b, or ring c is bonded to R 601 and R 602 It means that the atoms that make up R are bonded together. 601 is bonded to the a ring, and R 601and ring a may be fused to form a two-ring (or three- or more-ring) fused nitrogen-containing heterocycle. Specific examples of the nitrogen-containing heterocycle include compounds corresponding to the nitrogen-containing two- or more-ring fused heterocyclic groups in specific example group G2. R 601 When is bonded to ring b, R 602 When R is bonded to ring a, 602 The same applies when is bonded to ring c.
[0652] In one embodiment, the ring a, ring b, and ring c in the general formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms. In one embodiment, the ring a, ring b, and ring c in the general formula (6) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.
[0653] In one embodiment, R in general formula (6) 601 and R 602 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms is preferred.
[0654] In one embodiment, the compound represented by the general formula (6) is a compound represented by the following general formula (62):
[0655] [ka]
[0656] [(In the general formula (62), R 601A is R 611 and R 624 to form a substituted or unsubstituted heterocycle, or not to form a substituted or unsubstituted heterocycle, R that does not form the substituted or unsubstituted heterocycle 601A teeth, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 602A is R 613 and R 631 to form a substituted or unsubstituted heterocycle, or not to form a substituted or unsubstituted heterocycle, R that does not form the substituted or unsubstituted heterocycle 602A teeth, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or A group represented by the following general formula (621): R 611 ~R 613 , R 621 ~R 624 , and R 631 ~R 634 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted heterocyclic ring, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring 611 ~R 613 , R 621 ~R 624 , and R 631 ~R 634 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 906 a group represented by -COOR 907 a group represented by -N(R 6A )(R 6B ) a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0657] [ka]
[0658] (In the general formula (621), R 651 ~R 658One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 651 ~R 658 One of them is the binding site with L6, R does not form the substituted or unsubstituted monocyclic ring, does not form the substituted or unsubstituted fused ring, and is not a bonding position with L 651 ~R 658 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 906 a group represented by -COOR 907 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 65A ~R 65B The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring; 65A ~R 65B are each independently, a substituted or unsubstituted alkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L6 is single bond, a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms; a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, * 62 indicates the bonding position with the nitrogen atom, * 65 is R 651 ~R 658 indicates the bond position with one of the following:
[0659] R in the general formula (62) 601A and R 602A are R in the general formula (6), respectively. 601 and R 602 is a group corresponding to For example, R 601A and R 611 may be bonded to form a two-ring (or three- or more-ring) nitrogen-containing heterocyclic ring in which a ring containing the ring is fused with a benzene ring corresponding to ring a. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing two- or more-ring fused heterocyclic groups in specific example group G2. 601A and R 624 If R 602A and R 613When R is bonded, 602A and R 631 The same applies when the two are combined.
[0660] R 611 ~R 613 , R 621 ~R 624 , and R 631 ~R 634 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or They may be bonded to each other to form a substituted or unsubstituted fused ring. For example, R 611 and R 612 may be bonded to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, or the like is fused to the six-membered ring to which they are bonded, and the fused ring formed is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring.
[0661] In one embodiment, R that does not contribute to ring formation 611 ~R 613 , R 621 ~R 624 , and R 631 ~R 634 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or -N(R 6A )(R 6B ) is a group represented by the formula:
[0662] In one embodiment, R that does not contribute to ring formation 611 ~R 613 , R 621 ~R 624 , and R 631 ~R 634 are each independently, hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or -N(R 6A )(R 6B ) is a group represented by the formula:
[0663] In one embodiment, R that does not contribute to ring formation 613 , R 621 ~R 624 , and R 631 ~R 634 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or -N(R 6A )(R 6B ) is a group represented by the formula:
[0664] In one embodiment, R that does not contribute to ring formation 611 ~R 613 , R 621 ~R 624 , and R 631 ~R 634 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or -N(R 6A )(R 6B ) is a group represented by R 611 ~R 613 , R 621 ~R 624 , and R 631 ~R 634 At least one of the groups is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and —N(R 6A )(R 6B ) is at least one of the groups represented by the formula (I).
[0665] In one embodiment, R that does not contribute to ring formation 611 ~R 613 , R 621 ~R 624 , and R631 ~R 634 are each independently, a hydrogen atom, or -N(R 6A )(R 6B ) is a group represented by R 611 ~R 613 , R 621 ~R 624 , and R 631 ~R 634 At least one of the -N(R 6A )(R 6B ) is a group represented by the formula:
[0666] In one embodiment, R 6 is a cyclic group that does not contribute to ring formation and is not involved in bonding with L 6 . 651 ~R 658 is a hydrogen atom.
[0667] In one embodiment, the group represented by general formula (621) is the following general formula (622):
[0668] [ka]
[0669] (In the general formula (622), R 655 ~R 658 One of the R 655 ~R 658 are each independently R in the general formula (621). 655 ~R 658 is synonymous with R 651 ~R 654 , and R 65A ~R 65B is R in the general formula (621). 651 ~R 654 , and R 65A ~R 65B is synonymous with * 62 is * in the general formula (621). 62 is equivalent to
[0670] In one embodiment, the compound represented by the general formula (62) is a compound represented by the following general formula (62A):
[0671] [ka]
[0672] (In the general formula (62A), R 641 ~R 645 , R 661 ~R 665 , and R 671 ~R 675 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 641 ~R 645 , R 661 ~R 665 , and R 671 ~R 675 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 6A )(R 6B ) a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 612 , and R 631 ~R 634 are each independently R in the general formula (62). 612 , and R 631 ~R 634 is synonymous with R 651 ~R 658 , and R 65A ~R 65B are each independently R in the general formula (622). 651 ~R 658 , and R 65A ~R 65B is equivalent to
[0673] In one embodiment, the compound represented by the general formula (62) is a compound represented by the following general formula (62B):
[0674] [ka]
[0675] (In the general formula (62B), R 641 ~R 645 , R 681 ~R 685 , and R 691 ~R 695 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 641 ~R 645 , R 681 ~R 685 , and R691 ~R 695 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 6A )(R 6B ) a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 612 , and R 621 ~R 624 are as defined in the general formula (62), and R 612 , and R 621 ~R 624 are each independently R in the general formula (62). 612 , and R 621 ~R 624 is synonymous with R 651 ~R 658 , and R 65A ~R 65B is as defined in the general formula (622), and R 651 ~R 658 , and R 65A ~R 65B are each independently R in the general formula (622). 651 ~R 658 , and R 65A ~R65B is equivalent to
[0676] In one embodiment, the compound represented by the general formula (62) is a compound represented by the following general formula (62C):
[0677] [ka]
[0678] (In the general formula (62C), R 641 ~R 645 , R 661 ~R 665 , R 671 ~R 675 , R 681 ~R 685 , and R 691 ~R 695 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 641 ~R 645 , R 661 ~R 665 , R 671 ~R 675 , R 681 ~R 685 , and R 691 ~R 695 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 6A )(R 6B ) a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 612 is as defined in the general formula (62), and R 612 is R in general formula (62) 612 is synonymous with R 651 ~R 658 , and R 65A ~R 65B is as defined in the general formula (622), and R 651 ~R 658 , and R 65A ~R 65B are each independently R in the general formula (622). 651 ~R 658 , and R 65A ~R 65B is equivalent to
[0679] In one embodiment, the compound represented by the general formula (62A) is a compound represented by the following general formula (62A-1):
[0680] [ka]
[0681] (In the general formula (62A-1), R 612 , R 633 , R 643 , R 661 ~R 665 , R 671 ~R675 , R 651 ~R 658 , and R 65A ~R 65B are each independently R in the general formula (62A). 612 , R 633 , R 643 , R 661 ~R 665 , R 671 ~R 675 , R 651 ~R 658 , and R 65A ~R 65B is equivalent to
[0682] In one embodiment, the compound represented by the general formula (62B) is a compound represented by the following general formula (62B-1):
[0683] [ka]
[0684] (In the general formula (62B-1), R 612 , R 622 , R 643 , R 681 ~R 685 , R 691 ~R 695 , R 651 ~R 658 , and R 65A ~R 65B are each independently R in the general formula (62B). 612 , R 622 , R 643 , R 681 ~R 685 , R 691 ~R 695 , R 651 ~R 658 , and R 65A ~R 65B is equivalent to
[0685] In one embodiment, the compound represented by general formula (62C) is a compound represented by the following general formula (62C-1):
[0686] [ka]
[0687] (In the general formula (62C-1), R 612 , R 643 , R 681 ~R 685 , R 691 ~R 695 , R 651 ~R 658 , and R 65A ~R 65B are each independently R in the general formula (62C). 612 , R 622 , R 643 , R 681 ~R 685 , R 691 ~R 695 , R 651 ~R 658 , and R 65A ~R 65B is equivalent to
[0688] In one embodiment, R in the general formulae (62A), (62B), (62C), (62A-1), (62B-1), and (62C-1) 612 , R 622 , R 633 , R 643 , R 661 ~R 665 , R 671 ~R 675 , R 681 ~R 685 , R 691 ~R 695 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0689] In one embodiment, R in the general formulae (62A), (62B), (62C), and the general formulae (62A-1), (62B-1), and (62C-1) 612 , R 622 , R 633 , R 643 , R 661 ~R 665 , R 671 ~R 675 , R 681 ~R 685 , R 691 ~R 695 are each independently, a hydrogen atom, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0690] The compound represented by the general formula (6) is first prepared by connecting the ring a, ring b, and ring c to a linking group (NR 601 and groups containing NR 602 The intermediate is produced by linking the rings a, b, and c with a linking group (a group containing a boron atom) (reaction 2), and the final product is produced by linking the rings a, b, and c with a linking group (a group containing a boron atom) (reaction 2). In reaction 1, an amination reaction such as the Bachburt-Hartwig reaction can be applied. In reaction 2, a tandem hetero-Friedel-Crafts reaction can be applied.
[0691] (Compounds represented by general formulas (64-1) to (64-5)) The compounds represented by general formulas (64-1) to (64-5) will be explained.
[0692] In one embodiment, the compound represented by the general formula (6) is selected from the group consisting of compounds represented by the following general formulae (64-1) to (64-5).
[0693] [ka]
[0694] (In the general formula (64-1), X is O, S, Se, C(R403 )(R 404 ), or NR 405 is. R 401 and R 421 Paired with R 421 ~R 423 A set of two or more adjacent 423 and R 402 Paired with R 402 and R 424 Paired with R 424 ~R 427 A set of two or more adjacent 427 and R 412 Pairs with and R 412 and R 411 One or more pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 401 and R 402 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R 403 ~R 405 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 411 , R 412 , and R 421 ~R 427 are each independently a hydrogen atom or a substituent R, The substituents R are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ) halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 ~R 907 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 , which are identical or different from each other, R905 If there are multiple R 905 are the same or different from each other, R 906 If there are multiple R 906 are the same or different from each other, R 907 If there are multiple R 907 are either identical or different.)
[0695] (In the general formula (64-2), X is O, S, Se, C(R 403 )(R 404 ), or NR 405 is. R 401 and R 421 Paired with R 421 ~R 423 A set consisting of two or more adjacent R 423 and R 402 Paired with R 402 and R 424 Paired with R 424 ~R 427 A set of two or more adjacent 413 and R 414 Pairs with and R 414 and R 401 One or more pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 401 and R 402 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R 403 ~R 405 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 413 , R 414 , and R 421 ~R 427 are each independently a hydrogen atom or a substituent R, and the substituent R has the same meaning as the substituent R in the general formula (64-1).
[0696] (In the general formula (64-3), X and X' are each independently O, S, Se, C(R 403 )(R 404 ), or NR 405 is. R 401 and R 421 Paired with R 421 ~R 423 A set of two or more adjacent 423 and R 402 Paired with R 415 and R 416 Paired with R 416 and R 412 Pairs with and R 412 and R 411 One or more pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 401 and R 402 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R 403 ~R 405 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 411 , R 412 , R 415 , R 416 , and R 421 ~R 423 are each independently a hydrogen atom or a substituent R, and the substituent R has the same meaning as the substituent R in the general formula (41-1). R 403 If there are multiple R 403 are identical to or different from each other, R 404 If there are multiple R 404 are identical to or different from each other, R 405 If there are multiple R 405 are either identical or different.)
[0697] (In the general formula (64-4), X and X' are each independently O, S, Se, C(R 403 )(R 404 ), or NR 405 is. R 401 and R 421 Paired with R 421 ~R 423 A set of two or more adjacent 423 and R 402 Paired with R 402 and R 418 Paired with R 418 and R 417 Pairs with and R 412 and R 411 One or more pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 401 and R 402 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R 403 ~R 405 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 411 , R 412 , R 417 , R 418 , and R 421 ~R 423 are each independently a hydrogen atom or a substituent R, and the substituent R has the same meaning as the substituent R in the general formula (41-1). R 403 If there are multiple R 403 are identical to or different from each other, R 404 If there are multiple R 404 are identical to or different from each other, R 405 If there are multiple R 405 are either identical or different.)
[0698] (In the general formula (64-5), X and X' are each independently O, S, Se, C(R 403 )(R 404 ), or NR 405 is. R401 and R 421 Paired with R 421 ~R 423 A set of two or more adjacent 423 and R 402 Paired with R 402 and R 418 Paired with R 418 and R 417 Paired with R 413 and R 414 Pairs with and R 414 and R 401 One or more pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 401 and R 402 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R 403 ~R 405 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 411 , R 412 , R 417 , R 418 , and R 421 ~R 423 are each independently a hydrogen atom or a substituent R, and the substituent R has the same meaning as the substituent R in the general formula (41-1). R 403 If there are multiple R 403 are identical to or different from each other, R 404 If there are multiple R 404 are identical to or different from each other, R 405 If there are multiple R 405 are either identical or different.)
[0699] In one embodiment, the compound represented by the general formula (62) is a compound represented by the following general formula (64-2A):
[0700] [ka]
[0701] (In the general formula (64-2A), R 441 and R 421 Paired with R 421 ~R 423 A set consisting of two or more adjacent R 423 and R 442 Paired with R 442 and R 443 Paired with R 443 ~R 446 A set of two or more adjacent 447 ~R 450 A pair consisting of two or more adjacent 450 and R 441 One or more pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 441 and R 442 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 421 ~R 423 , and R 443 ~R 450 are each independently a hydrogen atom or a substituent R, and the substituent R has the same meaning as the substituent R in the general formula (64-1). X is O or S.
[0702] In one embodiment, the substituent in the case of "substituted or unsubstituted" in the general formulae (64-1) to (64-5) is an unsubstituted alkyl group having 1 to 50 carbon atoms; an unsubstituted haloalkyl group having 1 to 50 carbon atoms; an unsubstituted alkenyl group having 2 to 50 carbon atoms; an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms; an unsubstituted alkoxy group having 1 to 50 carbon atoms; an unsubstituted alkylthio group having 1 to 50 carbon atoms, an unsubstituted aryloxy group having 6 to 50 ring carbon atoms, an unsubstituted arylthio group having 6 to 50 ring carbon atoms, an unsubstituted aralkyl group having 7 to 50 carbon atoms; -Si(R 41 )(R 42 )(R 43 ), -C(=O)R 44 , -COOR 45 , -S(=O)2R 46 , -P(=O)(R 47 )(R 48 ), -Ge(R 49 )(R 50 )(R 51 ), -N(R 52 )(R 53 ), (where R 41 ~R 53 R are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms. 41 If there are two or more, there are two or more R 41 are the same or different, and R 42 If there are two or more, there are two or more R 42 are the same or different, and R 43 If there are two or more, there are two or more R 43 are the same or different, and R 44 If there are two or more, there are two or more R 44 are the same or different, and R 45 If there are two or more, there are two or more R 45 are the same or different, and R 46 If there are two or more, there are two or more R 46 are the same or different, and R 47 If there are two or more, there are two or more R 47 are the same or different, and R 48 If there are two or more, there are two or more R 48 are the same or different, and R 49 If there are two or more, there are two or more R 49 are the same or different, and R 50 If there are two or more, there are two or more R 50 are the same or different, and R 51 If there are two or more, there are two or more R 51 are the same or different, and R 52 If there are two or more, there are two or more R 52 are the same or different, and R 53 If there are two or more, there are two or more R53 are either identical or different.) hydroxy groups, halogen atoms, cyano group, nitro group, an aryl group having 6 to 50 ring carbon atoms, and It is selected from the group consisting of monovalent heterocyclic groups having 5 to 50 ring atoms.
[0703] In one embodiment, the substituent in the case of "substituted or unsubstituted" in the general formulae (64-1) to (64-5) is an unsubstituted alkyl group having 1 to 18 carbon atoms; an unsubstituted aryl group having 6 to 18 ring carbon atoms, and It is selected from the group consisting of unsubstituted heterocyclic groups having 5 to 18 ring atoms.
[0704] The compounds represented by general formulae (64-1) to (64-5) can be synthesized by using known alternative reactions and raw materials suited to the target compound.
[0705] (Specific examples of compounds represented by general formula (6)) Specific examples of the compound represented by the general formula (6) are listed below, but these are merely illustrative, and the compound represented by the general formula (6) is not limited to the following specific examples.
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[0745] Second Embodiment (electronic equipment) The electronic device according to this embodiment is equipped with the organic EL element according to any one of the above-described embodiments. Examples of the electronic device include a display device and a light-emitting device. Examples of the display device include display components (e.g., an organic EL panel module), televisions, mobile phones, tablets, and personal computers. Examples of the light-emitting device include lighting and vehicle lighting fixtures. The light-emitting device can be used in a display device, for example, as a backlight for a display device.
[0746] [Modifications of the embodiment] The present invention is not limited to the above-described embodiment, and any modifications and improvements that can achieve the object of the present invention are included in the present invention.
[0747] For example, the number of light-emitting layers in the organic EL element is not limited to two, and three or more light-emitting layers may be stacked. When the organic EL element has three or more light-emitting layers, it is sufficient that at least two of the light-emitting layers (the first light-emitting layer and the second light-emitting layer) satisfy the conditions described in the above embodiment. For example, the other light-emitting layers may be fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize light emission due to electron transition from a triplet excited state directly to the ground state.
[0748] Furthermore, when the organic EL element has a plurality of light-emitting layers, these light-emitting layers may be provided adjacent to each other, or the organic EL element may be a so-called tandem type organic EL element in which a plurality of light-emitting units are stacked via an intermediate layer.
[0749] In addition, the specific structure and shape in carrying out the present invention may be other structures within the scope of achieving the object of the present invention. [Example]
[0750] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples in any way.
[0751] <Compound> The structures of the compounds used as the first host material in the production of the organic EL devices according to Examples 1 to 6 and Reference Examples 1 and 2 are shown below.
[0752] [ka]
[0753] The structures of the compounds used as the second host material in the production of the organic EL devices according to Examples 1 to 6 and Reference Examples 1 and 2 are shown below.
[0754] [ka]
[0755] The structures of the first light-emitting compounds or second light-emitting compounds used in the production of the organic EL devices according to Examples 1 to 6 and Reference Examples 1 and 2 are shown below.
[0756] [ka]
[0757] The structures of other compounds used in the production of the organic EL devices according to Examples 1 to 6 and Reference Examples 1 and 2 are shown below.
[0758] [ka]
[0759] <Fabrication of organic EL elements> An organic EL device was fabricated and evaluated as follows.
[0760] Example 1 A 25mm x 75mm x 1.1mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an 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 ITO transparent electrode had a film thickness of 130nm. The cleaned glass substrate with transparent electrode lines was attached to a substrate holder in a vacuum deposition apparatus, and compound HIL-1 was first deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 5 nm. Next, the compound HTL-1 was vapor-deposited on this hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, compound EBL-1 was vapor-deposited on the first hole transport layer to form a second hole transport layer (sometimes referred to as an electron blocking layer) having a thickness of 10 nm. Next, on the second hole transport layer, the compound BH1-1 (first host material) and the compound BD1 (first light-emitting compound) were co-deposited to form a first light-emitting layer having a thickness of 5 nm, in which the proportion of the compound BH1-1 in the first light-emitting layer was 98 mass % and the proportion of the compound BD1 in the first light-emitting layer was 2 mass %. Next, compound BH-2 (second host material) and compound BD1 (second light-emitting compound) were co-deposited on the first light-emitting layer to form a second light-emitting layer having a thickness of 20 nm, in which the proportion of compound BH-2 in the second light-emitting layer was 98 mass % and the proportion of compound BD1 in the second light-emitting layer was 2 mass %. Next, the compound aET-1 was vapor-deposited on the second light-emitting layer to form a first electron transporting layer (sometimes referred to as a hole blocking layer) having a thickness of 10 nm. Next, the compound bET-1 was vapor-deposited on the first electron transport layer to form a second electron transport layer having a thickness of 15 nm. Next, a compound Liq (8-quinolinolato)lithium was vapor-deposited on the second electron-transporting layer to form a 1-nm-thick electron-injecting layer. Liq is an abbreviation for (8-quinolinolato)lithium. Next, metal Al was vapor-deposited on the electron injection layer to form a cathode with a thickness of 80 nm. The device configuration of Example 1 is shown in outline below. ITO(130) / HIL-1(5) / HTL-1(80) / EBL-1(10) / BH1-1:BD1(5,98%:2%) / BH-2:BD1(2025,98%:2%) / aET-1(10) / bET-1(15) / Liq(1) / Al(80) In the device configurations shown in simplified form, the numbers in parentheses indicate film thicknesses (unit: nm). Similarly, the numbers in parentheses expressed as percentages (98%:2%) indicate the proportions (mass %) of the host material (compound BH1-1 or BH-2) and the light-emitting compound (compound BD1) in the first or second light-emitting layer. The same notation is used hereinafter.
[0761] [Examples 2 and 3] The organic EL devices of Examples 2 and 3 were fabricated in the same manner as the organic EL device of Example 1, except that the compound BH1-1 used as the first host material in forming the first emitting layer was changed to the compound shown in Table 1.
[0762] Examples 4 to 6 The organic EL devices of Examples 4 to 6 were fabricated in the same manner as the organic EL device of Example 1, except that the compound BH1-1 used as the first host material in forming the first emitting layer was changed to the compound shown in Table 2, and the compound BD1 used as the first emitting compound and the second emitting compound material was changed to the compound BD2.
[0763] [Reference example 1] The organic EL element of Reference Example 1 was fabricated in the same manner as the organic EL element of Example 1, except that the first emitting layer and the second emitting layer in Example 1 were replaced with only the second emitting layer, and the film thickness was set to 25 nm.
[0764] [Reference example 2] The organic EL element of Reference Example 2 was fabricated in the same manner as the organic EL element of Example 4, except that the first emitting layer and the second emitting layer in Example 4 were replaced with only the second emitting layer, and the film thickness was set to 25 nm.
[0765] <Evaluation of organic EL elements> The organic EL devices prepared in Examples 1 to 6 and Reference Examples 1 and 2 were evaluated as follows. The evaluation results are shown in Tables 1 and 2.
[0766] [First orientation σ1 and second orientation σ2] The orientation of the luminescent compound was calculated by comparing the simulation results obtained using the optical simulation software Setfos 5.0 (manufactured by Fluxim AG) with the experimental values obtained using the device 100 shown in Figure 6.
[0767] (Calculation of experimental values) A 50 nm thick film (see Sample (BH:BD) in FIG. 6) containing a host material (see BH in FIG. 6) and a light-emitting compound (see BD in FIG. 6) was formed by vacuum deposition on a quartz substrate (see Quartz sub. in FIG. 6) with a refractive index of 1.46 at 460 nm. The mass ratio of the host material to the light-emitting compound in this film was host material:light-emitting compound=98:2. The quartz substrate on which the film was formed was set in a jig of an IMS 5000 apparatus (apparatus 100 shown in FIG. 6) manufactured by ASAHI SPECTRA, with the film surface facing downward. A thin layer of immersion oil with a refractive index of 1.515 (see Immersion oil in Figure 6) was applied to the quartz substrate side, and a hemisphere prism (see Hemisphere prism in Figure 6) was placed in place so that no air was trapped between the silicone oil and the hemisphere prism. An LED light source (see LED in Figure 6) with 365 nm excitation light, which the host material absorbs, was irradiated onto the film surface from below through a diffusion film (see diffusion film in Figure 6), exciting the host material, and the PL spectrum of the light emitted by the luminescent compound resulting from energy transfer from the host was measured using a detector (see Detector in Figure 6). The detector is equipped with a p-polarizer (see p-polarized film in Figure 6), and the spectrum can be measured through the polarizing film, which is set to transmit only p-polarized light. The detector's measurement angle can be changed, so the PL spectrum was measured in the wavelength range of 350 nm to 800 nm while changing the angle in 3° increments from 0° to 72°, with the vertical direction being 0°.
[0768] (Calculation of simulation values) The optical simulation software Setfos 5.0 was launched, and the film thicknesses were entered in the order of air / host material:luminescent compound / quartz substrate / oil immersion oil / hemispherical prism so that the film thickness would be the same as in the experiment. The refractive index of air was 1.00, that of the quartz substrate was 1.46, that of the immersion oil was 1.515, that of the hemispherical prism was 1.52, and the refractive index of the host material was the n and k data files obtained from spectroscopic ellipsometry measurements. The detection angle dependence of p-polarized light intensity was calculated for each molecular orientation value, which indicates the degree of orientation of the luminescent compound, in the range of 0.70 to 1.00. The experimental and simulation values were superimposed, and the molecular orientation value of the simulation curve that best matched the experimental curve in the detection angle range of 45° to 72° was determined as the orientation value of the luminescent compound. Figure 7 shows an example of a graph showing experimental and simulated values, where the p-polarized PL intensity at 465 nm in the PL spectrum (range 350 nm to 800 nm) is plotted against the detection angle. In Figure 7, σ' represents molecular orientation. Figure 7 shows that the experimental values are close to the simulated values when the molecular orientation is 0.88.
[0769] Relative value of external quantum efficiency (EQE) Current density is 10mA / cm 2 The spectral radiance spectrum when a voltage was applied to the element so that the value was as follows 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 Lambertian radiation was used. Using the following formula (Number 100), the EQE (%) of each example (Examples 1 to 3 and Reference Example 1) was calculated as "EQE (relative value: %)" when the EQE (%) of Reference Example 1 was set to 100. EQE of each example (relative value: %) = (EQE of each example (%) / EQE of Reference Example 1 (%)) × 100 ... (number 100) Using the following formula (Equation 101), the EQE (%) of each example (Examples 4 to 6 and Reference Example 2) was calculated as "EQE (relative value: %)" when the EQE (%) of Reference Example 2 was set to 100. EQE of each example (relative value: %) = (EQE of each example (%) / EQE of Reference Example 2 (%)) × 100 ... (Number 101)
[0770] [Emission efficiency of the promptly emitting component EQE Prompt Relative value of The external quantum efficiency (EQE) is the luminescence efficiency (EQE) of the luminescence component (prompt component) from the singlet exciton generated by the first recombination. Prompt and the luminous efficiency EQE of the luminescent component due to the TTF mechanism TFT Luminous efficiency (EQE) Prompt The luminescence efficiency EQE is calculated from the TTF-derived luminescence intensity ratio and the external quantum efficiency EQE is calculated. TFT It can be found by subtracting
[0771] The TTF-derived luminescence intensity ratio can be measured by the transient EL method. The transient EL method is a technique for measuring the decay behavior (transient characteristics) of EL luminescence after the DC voltage applied to the element is removed. The EL luminescence intensity is divided into the luminescence component from singlet excitons generated in the first recombination and the luminescence component from singlet excitons generated via the TTF phenomenon. The lifetime of singlet excitons is extremely short, on the order of nanoseconds, so they decay quickly after the DC voltage is removed.
[0772] On the other hand, the TTF phenomenon occurs due to the emission from singlet excitons, which are generated via triplet excitons, which have a long lifetime, and therefore decays slowly. Because there is a large time difference between the emission from singlet excitons and the emission from triplet excitons, the emission intensity derived from TTF can be determined. Specifically, it can be determined using the following method.
[0773] The transient EL waveform is measured as follows (see Figure 8). A pulse voltage waveform output from a voltage pulse generator (PG) is applied to the EL element. The applied voltage waveform is captured by an oscilloscope (OSC). When a pulse voltage is applied to the EL element, the EL element emits pulsed light. This light emission is captured by the oscilloscope (OSC) via a photomultiplier tube (PMT). The voltage waveform and pulsed light emission are synchronized and captured in a personal computer (PC).
[0774] Furthermore, the TTF-derived luminescence intensity ratio is determined by analyzing the transient EL waveform as follows.
[0775] The decay behavior of the emission intensity based on the TTF phenomenon is modeled by solving the rate equation for the decay behavior of triplet excitons. The triplet exciton density n T The decay time of triplet excitons is the decay rate v A and the decay rate v of triplet excitons due to collisions C can be expressed by the following rate equation using
[0776]
number
[0777] By approximately solving this differential equation, we obtain the following equation, where I TTF is the luminescence intensity derived from TTF, and A is a constant. In this way, if the transient EL luminescence is based on TTF, the reciprocal of the square root of the intensity can be expressed by a linear approximation. Therefore, the measured transient EL waveform data is fitted to the following approximation formula to find the constant A. In this case, the luminescence intensity at time t=0 when the DC voltage is removed is 1 / A 2 is defined as the TTF-derived luminescence intensity ratio.
[0778]
number
[0779] The graph in Figure 9 shows an example of measurements when a certain DC voltage is applied to the EL element and then the voltage is removed, and shows the change in the luminous intensity of the EL element over time. -8 The DC voltage was removed at 10 seconds. The graph shows the brightness when the voltage was removed as 1. After that, the brightness increased by approximately 2 × 10 -7 After a rapid decay up to 10 seconds, a gradual decay component appears. The graph in Figure 10 has the origin at the time of voltage removal, and -5 This graph plots the reciprocal of the square root of the light intensity up to 1 / 2.41 seconds, and shows that it can be well approximated by a straight line. When the straight line is extended to the time origin, the value of the intersection point A with the vertical axis is 2.41. Therefore, the TTF-derived luminescence intensity ratio obtained from this transient EL waveform is 1 / 2.41. 2 =0.17, which means that 17% of the total luminescence intensity comes from TTF. The fitting to the straight line is preferably performed by the least squares method. -5 Fitting using values down to the second is preferred.
[0780] Emission efficiency EQE from singlet excitons generated upon first recombination Prompt(Emission efficiency EQE of prompt emission component Prompt ) (unit: %) is calculated using the external quantum efficiency EQE (unit: %) of the entire device by the following formula:
[0781]
number
[0782] The organic EL devices of the Examples and Reference Examples were prepared by the above-mentioned method, and a voltage pulse waveform (pulse width: 500 microseconds, frequency: 20 Hz, voltage: 0.1 to 100 mA / cm) was output from a pulse generator (Agilent Technologies, high-speed pulse power supply 8114A). 2 A voltage equivalent to 100 kJ / s was applied, and the EL emission was input to a photomultiplier tube (Hamamatsu Photonics, R928). The pulse voltage waveform and the EL emission were synchronized and captured on an oscilloscope (Tektronix, 2440) to obtain a transient EL waveform. The organic EL devices of the examples and reference examples were energized at room temperature for a time of about 3×10 -8 At 200 s, the pulse voltage was removed. The point at which the voltage is removed is taken as the origin, and after the voltage is removed, 1.5 x 10 -5 From the graph plotting the reciprocal of the square root of the light intensity up to seconds, it was found that the current density was 10 mA / cm 2 Instantaneous luminous efficiency (EQE) Prompt (Unit: %) was calculated.
[0783] Using the following formula (Equation 102), the instantaneous luminous efficiency EQE of Reference Example 1 Prompt EQE (%) of each example (Examples 1 to 3 and Reference Example 1) when the EQE is 100 Prompt (%) to "EQE Prompt The results were calculated as "(relative value: %)". EQE for each example Prompt (Relative value:%) = (EQE of each example Prompt (%) / EQE of Reference Example 1 Prompt (%)) x 100 ... (number 102) Using the following formula (Equation 103), the EQE of Reference Example 2 PromptEQE of each example (Examples 4 to 6 and Reference Example 2) when (%) is taken as 100 Prompt (%) to "EQE Prompt The results were calculated as "(relative value: %)". EQE for each example Prompt (Relative value:%) = (EQE of each example Prompt (%) / EQE of Reference Example 2 Prompt (%)) x 100 ... (number 103)
[0784] [|λ1-λ2| and |FWHM1-FWHM2|] The first and second films were prepared using the method described above, and the maximum peak wavelength λ1 and full width at half maximum FWHM1 of the PL spectrum of the first film (with the same composition as the first light-emitting layer) and the maximum peak wavelength λ2 and full width at half maximum FWHM2 of the PL spectrum of the second film (with the same composition as the second light-emitting layer) were measured. FWHM is an abbreviation for full width at half maximum. From the obtained values, |λ1-λ2| (unit: nm) and |FWHM1-FWHM2| (unit: nm) were calculated. In Tables 1 and 2, Δλ represents |λ1−λ2|, and ΔFWHM represents |FWHM1−FWHM2|.
[0785] [Table 1]
[0786] [Table 2]
[0787] In the organic EL devices according to Examples 1 to 6, the external quantum efficiency EQE was improved by satisfying the relationships of the above formula (Formula 1) and the above formula (Formula 2), and the luminous efficiency of the entire device was improved.
[0788] According to the organic EL devices of Examples 1 to 3, the closer the value of σ1 / σ2 is to 1, the higher the instantaneous luminous efficiency EQE Prompt is the instantaneous luminous efficiency EQE of Reference Example 1 Prompt, and the light extraction efficiency of the promptly emitted light component in the first light-emitting layer was improved. According to the organic EL devices of Examples 4 to 6, the closer the value of σ1 / σ2 is to 1, the higher the instantaneous luminous efficiency EQE Prompt is the instantaneous luminous efficiency EQE of Reference Example 2 Prompt , and the light extraction efficiency of the promptly emitted light component in the first light-emitting layer was improved. [Explanation of symbols]
[0789] 1...organic EL element, 2...substrate, 3...anode, 4...cathode, 51...first light-emitting layer, 52...second light-emitting layer, 6...hole injection layer, 7...hole transport layer, 8...electron transport layer, 9...electron injection layer
Claims
1. An organic electroluminescence element, an anode; A cathode; a light-emitting region disposed between the anode and the cathode; the light-emitting region includes a first light-emitting layer and a second light-emitting layer; the first light-emitting layer contains a first host material and a first light-emitting compound; the second light-emitting layer contains a second host material and a second light-emitting compound; the first host material and the second host material are different from each other, the first luminescent compound and the second luminescent compound are the same or different from each other, The triplet energy T of the first host material 1 (H1) and the triplet energy T 1 (H2) satisfies the relationship of the following formula (Formula 1), The first light-emitting compound exhibits a first orientation (σ 1 ) and The second light-emitting compound exhibits a second orientation (σ 2 ) and The second orientation (σ 2 ) to the first orientation (σ 1 ) satisfies the relationship of the following formula (Formula 2): Organic electroluminescent element. T 1 (H1)>T 1 (H2)…(Number 1) σ 1 / σ 2 ≥0.9 …(Equation 2)
2. The first orientation (σ 1 ) is 0.80 or more, The organic electroluminescence device according to claim 1 .
3. The second orientation (σ 2 ) is 0.90 or more; 3. The organic electroluminescence device according to claim 1 or 2.
4. The maximum peak wavelength λ1 and half width FWHM1 of the PL spectrum of the first film, and the maximum peak wavelength λ2 and half width FWHM2 of the PL spectrum of the second film satisfy the following mathematical expressions (Mathematical Expression 20) and (Mathematical Expression 30): The organic electroluminescence device according to claim 1 . |λ1-λ2| ≦ 3nm…(Math. 20) |FWHM1-FWHM2| ≦ 2 nm (Equation 30)
5. the first light-emitting layer is disposed between the anode and the second light-emitting layer; The organic electroluminescence device according to claim 1 .
6. the first light-emitting layer and the second light-emitting layer are in direct contact with each other; The organic electroluminescence device according to claim 1 .
7. The triplet energy T of the first luminescent compound 1 (D1) and the triplet energy T 1 (H1) satisfies the relationship of the following formula (Formula 3), The organic electroluminescence device according to claim 1 . T 1 (D1)>T 1 (H1) …(number 3)
8. The singlet energy S of the first host material 1 (H1) and the singlet energy S 1 (D1) satisfies the relationship of the following formula (Formula 4): The organic electroluminescence device according to claim 1 . S 1 (H1)>S 1 (D1) …(Number 4)
9. The triplet energy T of the second luminescent compound 1 (D2) and the triplet energy T 1 (H2) satisfies the relationship of the following formula (Formula 5), The organic electroluminescence device according to claim 1 . T 1 (D2)>T 1 (H2) …(Number 5)
10. The singlet energy S of the second host material 1 (H2) and the singlet energy S of the second luminescent compound 1 (D2) satisfies the relationship of the following formula (Formula 6): The organic electroluminescence device according to claim 1 . S 1 (H2)>S 1 (D2) …(Number 6)
11. the first luminescent compound and the second luminescent compound are each independently a compound that emits light having a maximum peak wavelength of 500 nm or less; The organic electroluminescence device according to claim 1 .
12. The first light-emitting compound and the second light-emitting compound are each independently represented by the following general formula (6): The organic electroluminescence device according to claim 1 . 【Chemical 1】 (In the general formula (6), Ring a, ring b and ring c each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, R 601 and R 602 each independently bond to the ring a, the ring b, or the ring c to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle, R that does not form a substituted or unsubstituted heterocycle 601 and R 602 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
13. At least one of the ring a, the ring b, and the ring c is —N(R 6A ) (R 6B ) and has one or more groups represented by R 6A and R 6B are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 6A When two or more R 6A are identical to or different from each other, R 6B When two or more R 6B are the same as or different from each other, The organic electroluminescence device according to claim 12 .
14. The organic electroluminescent device according to any one of claims 1 to 13, the first host material has a linking structure including a benzene ring and a naphthalene ring linked by a single bond in a molecule; the benzene ring and the naphthalene ring in the linking structure are each independently further fused with a single ring or a fused ring, or are not fused with a single ring or a fused ring; the benzene ring and the naphthalene ring in the linked structure are further linked by a bridge at at least one portion other than the single bond; Organic electroluminescent element.
15. The organic electroluminescent device according to claim 14, the bridge comprises a double bond; Organic electroluminescent element.
16. The organic electroluminescent device according to any one of claims 1 to 13, the first host material has a biphenyl structure in which a first benzene ring and a second benzene ring are connected by a single bond in a molecule; the first benzene ring and the second benzene ring in the biphenyl structure are further linked by a bridge at at least one moiety other than the single bond; Organic electroluminescent element.
17. The organic electroluminescence device according to claim 16, the first benzene ring and the second benzene ring in the biphenyl structure are further linked by the bridge at one site other than the single bond; Organic electroluminescent element.
18. 18. The organic electroluminescence device according to claim 16 or 17, the bridge comprises a double bond; Organic electroluminescent element.
19. The organic electroluminescence device according to claim 16, the first benzene ring and the second benzene ring in the biphenyl structure are further connected by the bridge at two portions other than the single bond, the crosslink does not contain a double bond; Organic electroluminescent element.
20. 20. The organic electroluminescence device according to claim 1, wherein the first light-emitting compound and the second light-emitting compound are identical to each other.
21. a hole transport layer disposed between the anode and the light-emitting region; The organic electroluminescence device according to any one of claims 1 to 20.
22. an electron transport layer disposed between the cathode and the light-emitting region; The organic electroluminescence device according to any one of claims 1 to 21.
23. An electronic device equipped with the organic electroluminescence element according to any one of claims 1 to 22.
Citation Information
Patent Citations
Organic electroluminescent element and electronic device
WO2021210305A1