Organic electroluminescent element and electronic device
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- IDEMITSU KOSAN CO LTD
- Filing Date
- 2025-12-25
- Publication Date
- 2026-06-26
AI Technical Summary
[0025]根据本发明的一个方案,可以提供性能提高了的有机电致发光元件。另外,根据本发明的一个方案,可以提供搭载了该有机电致发光元件的电子设备。
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Figure CN122294722A_ABST
Abstract
Description
Technical Field
[0001] This invention relates to organic electroluminescent elements and electronic devices. Background Technology
[0002] Organic electroluminescent elements (hereinafter sometimes referred to as "organic EL elements") are used in full-color displays. When a voltage is applied to an organic EL element, holes are injected from the anode into the emissive layer, and electrons are injected from the cathode into the emissive layer. Then, in the emissive layer, the injected holes recombine with the electrons to form excitons. At this time, according to the statistical law of electron spin, singlet excitons are generated at a ratio of 25%, and triplet excitons are generated at a ratio of 75%. Singlet excitons release energy in the form of fluorescence when they return to the ground state, and triplet excitons release energy in the form of phosphorescence when they return to the ground state.
[0003] To improve the performance of organic EL devices, various studies have been conducted on compounds and device structures used in organic EL devices. Performance characteristics of organic EL devices include, for example, brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime.
[0004] For example, in document 1 (International Publication No. 2021 / 162057), a series-connected organic EL element with stacked light-emitting units including a first light-emitting layer and a second light-emitting layer was studied. Summary of the Invention
[0005] Although various studies have been conducted on compounds and device structures for organic EL devices, further improvements in the performance of organic EL devices are still being pursued.
[0006] The object of the present invention is to provide an organic electroluminescent element with improved component performance, and to provide an electronic device equipped with the organic electroluminescent element.
[0007] According to one aspect of the present invention, an organic electroluminescent element is provided, wherein,
[0008] The aforementioned organic electroluminescent element has an anode, a cathode, and two or more light-emitting units disposed between the anode and the cathode.
[0009] The aforementioned two or more light-emitting units include at least a first light-emitting unit having a first light-emitting region and a second light-emitting unit having a second light-emitting region.
[0010] The anode, the first light-emitting unit, the second light-emitting unit, and the cathode are arranged sequentially from the anode side toward the cathode side.
[0011] The aforementioned first luminescent region includes a first luminescent layer containing a first host material and a second luminescent layer containing a second host material.
[0012] The first light-emitting layer is disposed closer to the anode side than the second light-emitting layer.
[0013] The aforementioned second luminescent region includes a third luminescent layer containing a third host material and a fourth luminescent layer containing a fourth host material.
[0014] The third light-emitting layer is disposed closer to the anode side than the fourth light-emitting layer.
[0015] The first, second, third, and fourth light-emitting layers each independently contain a luminescent compound exhibiting a maximum peak wavelength of less than 500 nm.
[0016] The first main material mentioned above is different from the third main material mentioned above.
[0017] The first main material mentioned above is different from the second and fourth main materials mentioned above.
[0018] The third main material mentioned above differs from the second and fourth main materials mentioned above.
[0019] The second main material mentioned above may be the same as or different from the fourth main material mentioned above.
[0020] The triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material satisfy the following mathematical expression (Mathematical Expression 1).
[0021] The triplet energy T1(H3) of the third host material and the triplet energy T1(H4) of the fourth host material satisfy the following mathematical formula (Mathematical Formula 2).
[0022] T1(H1)>T1(H2) …(Mathematical Expression 1)
[0023] T1(H3)>T1(H4) …(Mathematical expression 2).
[0024] According to one aspect of the present invention, an electronic device incorporating an organic electroluminescent element according to one aspect of the present invention is provided.
[0025] According to one aspect of the present invention, an organic electroluminescent element with improved performance can be provided. Furthermore, according to another aspect of the present invention, an electronic device incorporating the organic electroluminescent element can be provided. Attached Figure Description
[0026] Figure 1 This is a diagram illustrating the general configuration of an example of an organic electroluminescent element according to one embodiment of the present invention. Detailed Implementation
[0027] [definition]
[0028] In this specification, a hydrogen atom means an isotope containing different numbers of neutrons, namely protium, deuterium, and tritium.
[0029] In this specification, the chemical structural formula does not explicitly show that the bonding positions of symbols such as "R" and "D" representing deuterium atoms are bonded to hydrogen atoms, i.e., protium atoms, deuterium atoms, or tritium atoms.
[0030] In this specification, the number of carbon atoms forming a ring refers to the number of carbon atoms in the ring itself of a compound whose atoms are bonded in a ring (e.g., monocyclic compounds, fused-ring compounds, bridged-ring compounds, carbocyclic compounds, and heterocyclic compounds). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of carbon atoms forming the ring. The term "number of carbon atoms forming a ring" is used as such unless otherwise specified. For example, the number of carbon atoms forming a ring is 6 for a benzene ring, 10 for a naphthalene ring, 5 for a pyridine ring, and 4 for a furan ring. Additionally, for example, the number of carbon atoms forming a ring is 13 for 9,9-diphenylfluorene and 25 for 9,9'-spirobifluorene.
[0031] Furthermore, when a benzene ring is substituted with an alkyl group, the carbon number of the alkyl group is not included in the number of carbon atoms in the ring-forming process of the benzene ring. Therefore, the number of carbon atoms in the cyclic benzene ring substituted with an alkyl group is 6. Similarly, when a naphthalene ring is substituted with an alkyl group, the carbon number of the alkyl group is not included in the number of carbon atoms in the ring-forming process of the naphthalene ring. Therefore, the number of carbon atoms in the cyclic naphthalene ring substituted with an alkyl group is 10.
[0032] In this specification, the number of cyclic atoms refers to the number of atoms constituting the ring itself in compounds with a cyclic structure (e.g., monocyclic, fused-ring, and ring assemblies). Atoms that do not constitute the ring (e.g., hydrogen atoms ending the bonds of the ring-forming atoms) and atoms contained in substituents when the ring is substituted are not included in the number of cyclic atoms. The term "number of cyclic atoms" as used below is the same unless otherwise stated. For example, the number of cyclic atoms in a pyridine ring is 6, in a quinazoline ring it is 10, and in a furan ring it is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or atoms constituting substituents are not included in the number of cyclic atoms in pyridine. Therefore, the number of cyclic atoms in a pyridine ring bonded with hydrogen atoms or substituents is 6. Furthermore, hydrogen atoms bonded to the carbon atoms of the quinazoline ring, or atoms constituting substituents, are not included in the number of cyclic atoms of the quinazoline ring. Therefore, the number of cyclic atoms in a quinazoline ring with bonded hydrogen atoms or substituents is 10.
[0033] In this specification, the phrase "ZZ group with substituted or unsubstituted carbon numbers of XX to YY" indicates the number of carbons when the ZZ group is unsubstituted; the number of carbons in substituents is not included. Here, "YY" is greater than "XX," where "XX" refers to an integer greater than 1, and "YY" refers to an integer greater than 2.
[0034] In this specification, the phrase "ZZ group with substituted or unsubstituted atoms of XX to YY" refers to the number of atoms when the ZZ group is unsubstituted, excluding the number of atoms of substituents when substitution has occurred. Here, "YY" is greater than "XX", where "XX" is an integer greater than or equal to 1, and "YY" is an integer greater than or equal to 2.
[0035] In this specification, "unsubstituted ZZ group" means "substituted or unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".
[0036] In this specification, "unsubstituted" when referred to as "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group has not been substituted with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.
[0037] Furthermore, in this specification, "substitution" when expressed as "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group have been replaced by a substituent. Similarly, "substitution" when expressed as "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group have been replaced by an AA group.
[0038] Substituents described in this specification
[0039] The substituents described in this specification are explained below.
[0040] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted aryl group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.
[0041] Unless otherwise stated in this specification, the number of cyclic atoms in the "unsubstituted heterocyclic group" is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.
[0042] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.
[0043] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkenyl group" is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
[0044] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkynyl group" is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
[0045] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted cycloalkyl group" is 3 to 50, preferably 3 to 20, and more preferably 3 to 6.
[0046] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted aryl group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.
[0047] Unless otherwise specified in this specification, the number of cyclic atoms in the "unsubstituted divalent heterocyclic group" is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.
[0048] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkylene group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.
[0049] • "Substituted or unsubstituted aryl groups"
[0050] Specific examples of "substituted or unsubstituted aryl" as described in this specification (specific example group G1) include unsubstituted aryl (specific example group G1A) and substituted aryl (specific example group G1B), etc. (Here, unsubstituted aryl refers to the case where "substituted or unsubstituted aryl" is "unsubstituted aryl", and substituted aryl refers to the case where "substituted or unsubstituted aryl" is "substituted aryl".) In this specification, when referred to only as "aryl", both "unsubstituted aryl" and "substituted aryl" are included.
[0051] "Substituted aryl" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl" group have been substituted with a substituent. Examples of "substituted aryl" include the group in Specific Example Group G1A below in which one or more hydrogen atoms of an "unsubstituted aryl" group have been substituted with a substituent, and the substituted aryl group in Specific Example Group G1B below. It should be noted that the examples of "unsubstituted aryl" and "substituted aryl" listed here are only examples. The "substituted aryl" described in this specification also includes the group in Specific Example Group G1B below in which hydrogen atoms bonded to the carbon atom of the aryl group itself have been further substituted with a substituent, and the group in Specific Example Group G1B below in which hydrogen atoms of the substituent have been further substituted with a substituent.
[0052] • Unsubstituted aryl groups (specific example group G1A):
[0053] Phenyl,
[0054] p-phenyl,
[0055] metaphenyl,
[0056] o-phenyl,
[0057] p-terphenyl-4-yl,
[0058] p-terphenyl-3-yl,
[0059] p-terphenyl-2-yl,
[0060] m-terphenyl-4-yl,
[0061] m-terphenyl-3-yl,
[0062] m-terphenyl-2-yl,
[0063] o-terphenyl-4-yl
[0064] o-terphenyl-3-yl
[0065] o-terphenyl-2-yl,
[0066] 1-Naphthyl,
[0067] 2-Naphthyl,
[0068] anthracene,
[0069] Benzanthracene,
[0070] Fiki,
[0071] Benzphenanthrene,
[0072] Finadenyl,
[0073] Pyrene
[0074] Chrysenyl,
[0075] Benzochrysenyl,
[0076] Triphenylenyl,
[0077] Benzo[ghi]triphenylenyl,
[0078] Tetracenyl,
[0079] Pentacenyl,
[0080] Fluorenyl,
[0081] 9,9'-Spirobi[fluorenyl],
[0082] Benzo[h]fluorenyl,
[0083] Dibenzo[def,p]fluorenyl,
[0084] Fluorenyl,
[0085] Benzo[def]chrysenyl,
[0086] Perylenyl and
[0087] a monovalent aryl group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-1) to (TEMP-15).
[0088]
[0089]
[0090] · Substituted aryl (specific example group G1B):
[0091] o-Tolyl,
[0092] m-Tolyl,
[0093] p-Tolyl,
[0094] p-Xylyl,
[0095] m-Xylyl,
[0096] o-Xylyl,
[0097] p-Isopropylphenyl,
[0098] m-Isopropylphenyl,
[0099] o-Isopropylphenyl,
[0100] p-tert-Butylphenyl,
[0101] m-tert-Butylphenyl,
[0102] o-tert-Butylphenyl,
[0103] 3,4,5-Trimethylphenyl
[0104] 9,9-Dimethylfluorenyl,
[0105] 9,9-Diphenylfluorenyl
[0106] 9,9-Bis(4-methylphenyl)fluorenyl,
[0107] 9,9-Bis(4-isopropylphenyl)fluorenyl,
[0108] 9,9-Bis(4-tert-butylphenyl)fluorenyl,
[0109] cyanophenyl,
[0110] Triphenylsilylphenyl
[0111] Trimethylsilylphenyl
[0112] Phenynaphthyl,
[0113] Naphthylphenyl and
[0114] A group derived from the ring structure shown in the above general formulas (TEMP-1) to (TEMP-15) by substitution of one or more hydrogen atoms of a monovalent group with a substituent.
[0115] • "Substituted or unsubstituted heterocyclic groups"
[0116] The term "heterocyclic group" as used in this specification refers to a cyclic group whose cyclic atoms contain at least one heteroatom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.
[0117] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.
[0118] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.
[0119] Specific examples of "substituted or unsubstituted heterocyclic groups" described in this specification (specific example group G2) include unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B), etc. (Here, unsubstituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group", and substituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group".) In this specification, the term "heterocyclic group" includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".
[0120] "Substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" have been substituted with a substituent. Specific examples of "substituted heterocyclic groups" include the group in example group G2A below where the hydrogen atoms of the "unsubstituted heterocyclic group" have been substituted, and the example of a substituted heterocyclic group in example group G2B below. It should be noted that the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are only examples. The "substituted heterocyclic groups" described in this specification also include the group in example group G2B where the hydrogen atoms bonded to the cyclic atoms of the heterocyclic group itself have been further substituted with a substituent, and the group in example group G2B where the hydrogen atoms of the substituent have been further substituted with a substituent.
[0121] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1), unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2), unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).
[0122] Specific example group G2B includes, for example, the following: a nitrogen-containing substituted heterocyclic group (specific example group G2B1), an oxygen-containing substituted heterocyclic group (specific example group G2B2), a sulfur-containing substituted heterocyclic group (specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) have been substituted with a substituent (specific example group G2B4).
[0123] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1):
[0124] pyrrole,
[0125] Imidazole group,
[0126] Pyrazolyl,
[0127] Triazole group,
[0128] Tetrazolyl,
[0129] Oxazolyl,
[0130] Isoxazolyl,
[0131] Oxadiazole group,
[0132] Thiazole group,
[0133] Isothiazolyl,
[0134] Thiadiazole group,
[0135] pyridyl,
[0136] pyridazinyl,
[0137] Pyrimidine group,
[0138] Pyrazinyl,
[0139] Triazine group
[0140] Indole,
[0141] Isoindolyl,
[0142] Indazine-based
[0143] Quinazine-based
[0144] Quinoline,
[0145] Isoquinoline,
[0146] Crenoline group
[0147] Phthaloazine
[0148] Quinazolinyl,
[0149] Quinoxaloyl,
[0150] Benzimidazole group,
[0151] Indazole group,
[0152] phenanthroline,
[0153] phenanthridine,
[0154] acridine group,
[0155] Phenazine group,
[0156] Carbazolyl,
[0157] Benzocarbazolyl,
[0158] Morpholinyl,
[0159] phenoxazine group,
[0160] phenothiazine group,
[0161] Azacarbazolyl, and
[0162] Diazacarbazolyl.
[0163] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2):
[0164] furanyl,
[0165] Oxazolyl,
[0166] Isoxazolyl,
[0167] Oxadiazole group,
[0168] Xuton base,
[0169] Benzofuranyl,
[0170] Isobenzofuranyl,
[0171] Dibenzofuranyl,
[0172] Naphthobenzofuranyl,
[0173] Benzoxazolyl,
[0174] Benzisoxazole group,
[0175] phenoxazine group,
[0176] Morpholinyl,
[0177] Dinaphthylfuranyl,
[0178] Azadibenzofuranyl,
[0179] diazadibenzofuranyl,
[0180] Azanaphthalenebenzofuranyl and
[0181] Diazanaphthenebenzofuranyl.
[0182] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3):
[0183] Thiophene group
[0184] Thiazole group,
[0185] Isothiazolyl,
[0186] Thiadiazole group,
[0187] benzothienyl
[0188] isobenzothienyl
[0189] dibenzothienyl
[0190] Naphthobenzothienyl
[0191] Benzothiazolyl,
[0192] Benzisothiazolyl,
[0193] phenothiazine group,
[0194] dinaphthothienyl
[0195] azadibenzothienyl
[0196] diazadibenzothienyl
[0197] azanaphthobenzothienyl and
[0198] diazanaphthobenzothienyl.
[0199] • A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):
[0200]
[0201]
[0202] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each can be independently composed of an oxygen atom, a sulfur atom, NH, or CH2. Among them, X... A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH.
[0203] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A When at least one of them is NH or CH2, the monovalent heterocyclic group derived from the ring structure shown in the above general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.
[0204] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1):
[0205] (9-phenyl)carbazole group,
[0206] (9-Biphenyl)carbazolyl,
[0207] (9-Phenyl)phenylcarbazolyl,
[0208] (9-Naphthyl)carbazole,
[0209] Diphenylcarbazole-9-yl,
[0210] Phenylexacarbazole-9-yl,
[0211] Methylbenzimidazole,
[0212] Ethylbenzimidazole,
[0213] Phenylacetyl,
[0214] Biphenyltriazine,
[0215] diphenyltriazine group,
[0216] phenylquinazolinyl, and
[0217] Biphenylquinazolinyl.
[0218] • Heterocyclic groups containing oxygen atoms (specific example group G2B2):
[0219] Phenyl dibenzofuranyl,
[0220] Methyldibenzofuranyl,
[0221] tert-butyldibenzofuranyl and
[0222] The monovalent residue of [9H-xanton-9,9'-[9H]fluorene].
[0223] • Heterocyclic groups containing sulfur atoms (specific example group G2B3):
[0224] Phenyl dibenzothiophene,
[0225] Methyldibenzothiophene,
[0226] tert-butyldibenzothiophene and
[0227] The monovalent residue of [9H-thiophene-9,9'-[9H]fluorene].
[0228] • Groups derived from the ring structures shown in the above general formulas (TEMP-16) to (TEMP-33) in which one or more hydrogen atoms of a monovalent heterocyclic group have been substituted with substituents (specific example group G2B4):
[0229] The aforementioned "one or more hydrogen atoms in a monovalent heterocyclic group" refers to hydrogen atoms bonded to the cyclic carbon atoms of the monovalent heterocyclic group, X A and Y A The hydrogen atom bonded to the nitrogen atom when at least one of them is NH and X A and Y A One of them is one or more hydrogen atoms in the methylene group when CH2 is present.
[0230] • "Substituted or unsubstituted alkyl groups"
[0231] As specific examples of "substituted or unsubstituted alkyl" described in this specification (specific example group G3), the following unsubstituted alkyl (specific example group G3A) and substituted alkyl (specific example group G3B) can be cited. (Here, unsubstituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when referred to as "alkyl", both "unsubstituted alkyl" and "substituted alkyl" are included.
[0232] "Substituted alkyl" refers to a group in which one or more hydrogen atoms of an "unsubstituted alkyl" have been substituted with a substituent. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms of an "unsubstituted alkyl" (specific example group G3A) have been substituted with a substituent, and examples of substituted alkyl (specific example group G3B). In this specification, "unsubstituted alkyl" refers to a chain-like alkyl group. Therefore, "unsubstituted alkyl" includes both straight-chain and branched-chain unsubstituted alkyl groups. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples; the "substituted alkyl" described in this specification also includes groups in which the hydrogen atoms of the alkyl group in specific example group G3B have been further substituted with a substituent, and groups in which the hydrogen atoms of the substituents in specific example group G3B have been further substituted with a substituent.
[0233] • Unsubstituted alkyl groups (specific example group G3A):
[0234] methyl,
[0235] Ethyl,
[0236] n-propyl,
[0237] Isopropyl,
[0238] n-Butyl,
[0239] Isobutyl,
[0240] sec-butyl and
[0241] tert-butyl.
[0242] • Substituted alkyl groups (specific example group G3B):
[0243] Heptafluoropropyl (including isomers),
[0244] Pentafluoroethyl,
[0245] 2,2,2-Trifluoroethyl and
[0246] Trifluoromethyl
[0247] • "Substituted or unsubstituted alkenyl groups"
[0248] Specific examples of "substituted or unsubstituted alkenyl groups" (specific example group G4) described in this specification include unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "substituted alkenyl group".) In this specification, when simply referred to as "alkenyl group", both "unsubstituted alkenyl group" and "substituted alkenyl group" are included.
[0249] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" group have been substituted with a substituent. Specific examples of "substituted alkenyl" include the "unsubstituted alkenyl" group (specific example group G4A) having a substituent and examples of substituted alkenyl groups (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples; the "substituted alkenyl" described in this specification also includes groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the alkenyl itself have been further substituted with a substituent, and groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the substituent have been further substituted with a substituent.
[0250] • Unsubstituted alkenyl groups (specific example group G4A):
[0251] vinyl,
[0252] Allyl
[0253] 1-Butenyl,
[0254] 2-Butenyl and
[0255] 3-Butenyl.
[0256] • Substituted alkenyl groups (specific example group G4B):
[0257] 1,3-Butadienyl,
[0258] 1-Methylvinyl
[0259] 1-Methylallyl,
[0260] 1,1-Dimethylallyl,
[0261] 2-Methylallyl and
[0262] 1,2-Dimethylallyl.
[0263] • "Substituted or unsubstituted alkynyl groups"
[0264] As specific examples of "substituted or unsubstituted alkynyl groups" described in this specification (specific example group G5), the following unsubstituted alkynyl groups (specific example group G5A) can be cited. (Here, unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group".) The following description of "alkynyl group" includes both "unsubstituted alkynyl group" and "substituted alkynyl group".
[0265] "Substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" have been replaced by a substituent. Specific examples of "substituted alkynyl group" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl group" (specific example group G5A) have been replaced by a substituent.
[0266] • Unsubstituted alkynyl group (specific example group G5A):
[0267] Acetylene group.
[0268] • "Substituted or unsubstituted cycloalkyl groups"
[0269] Specific examples of "substituted or unsubstituted cycloalkyl" described in this specification (specific example group G6) include unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B), etc. (Here, unsubstituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl".) In this specification, when referred to only as "cycloalkyl", both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.
[0270] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group have been substituted with a substituent. Specific examples of "substituted cycloalkyl" include the group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group (specific example group G6A) have been substituted with a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples. The "substituted cycloalkyl" described in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl" group of specific example group G6B have been substituted with a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted cycloalkyl" group of specific example group G6B have been further substituted with a substituent.
[0271] • Unsubstituted cycloalkyl groups (specific example group G6A):
[0272] Cyclopropyl,
[0273] Cyclobutyl,
[0274] Cyclopentyl,
[0275] Cyclohexyl,
[0276] 1-Adamantyl,
[0277] 2-Adamantyl,
[0278] 1-norborneol and
[0279] 2-norborneol.
[0280] • Substituted cycloalkyl groups (specific example group G6B):
[0281] 4-Methylcyclohexyl.
[0282] ·"-Si(R 901 (R) 902 (R) 903 The group shown in the figure”
[0283] As described in this specification, -Si(R) 901 (R) 902 (R) 903 Specific examples of the group shown in the figure (specific example group G7) can be given as follows:
[0284] -Si(G1)(G1)(G1),
[0285] -Si(G1)(G2)(G2),
[0286] -Si(G1)(G1)(G2),
[0287] -Si(G2)(G2)(G2),
[0288] -Si(G3)(G3)(G3) and
[0289] -Si(G6)(G6)(G6). Here.
[0290] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.
[0291] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
[0292] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.
[0293] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.
[0294] In -Si(G1)(G1)(G1), multiple G1s may be identical or different from each other.
[0295] In -Si(G1)(G2)(G2), multiple G2s may be the same or different from each other.
[0296] In -Si(G1)(G1)(G2), multiple G1s may be the same or different from each other.
[0297] In -Si(G2)(G2)(G2), multiple G2s may be the same or different from each other.
[0298] In -Si(G3)(G3)(G3), multiple G3s may be identical or different from each other.
[0299] In -Si(G6)(G6)(G6), multiple G6s may be identical or different from each other.
[0300] ·“-O-(R 904 The group shown in the figure”
[0301] As described in this specification, -O-(R) 904 Specific examples of the group shown in the figure (specific example group G8) can be given as follows:
[0302] -O(G1)
[0303] -O(G2),
[0304] -O(G3) and
[0305] -O(G6).
[0306] Here,
[0307] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.
[0308] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
[0309] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.
[0310] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.
[0311] ·“-S-(R 905 The group shown in the figure”
[0312] As described in this specification, -S-(R) 905 Specific examples of the group shown in the figure (specific example group G9) can be given as follows:
[0313] -S(G1)
[0314] -S(G2),
[0315] -S(G3) and
[0316] -S(G6).
[0317] Here,
[0318] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.
[0319] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
[0320] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.
[0321] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.
[0322] ·"-N(R 906 (R) 907 The group shown in the figure”
[0323] As described in this specification, -N(R) 906 (R) 907 Specific examples of the group shown (specific example group G10) can be given as follows:
[0324] -N(G1)(G1),
[0325] -N(G2)(G2),
[0326] -N(G1)(G2),
[0327] -N(G3)(G3) and
[0328] -N(G6)(G6).
[0329] Here,
[0330] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.
[0331] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
[0332] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.
[0333] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.
[0334] In -N(G1)(G1), multiple G1s may be the same or different from each other.
[0335] In -N(G2)(G2), multiple G2s may be the same or different from each other.
[0336] In -N(G3)(G3), multiple G3s may be the same or different from each other.
[0337] In -N(G6)(G6), multiple G6s may be the same or different from each other.
[0338] • "Halogen atom"
[0339] Specific examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.
[0340] • "Substituted or unsubstituted fluoroalkyl groups"
[0341] The term "substituted or unsubstituted fluoroalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group has been replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group have been replaced by fluorine atoms (perfluorinated groups). Unless otherwise specified in this specification, the number of carbon atoms in an "unsubstituted fluoroalkyl" group is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted fluoroalkyl" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl" group have been replaced by a substituent. It should be noted that the term "substituted fluoroalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in a "substituted fluoroalkyl" group have been further replaced by a substituent, and groups in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl" group have been further replaced by a substituent. As a specific example of "unsubstituted fluoroalkyl", examples can be given of groups in which one or more hydrogen atoms in the above-mentioned "alkyl" (specific example group G3) have been replaced by fluorine atoms.
[0342] • "Substituted or unsubstituted haloalkyl groups"
[0343] The term "substituted or unsubstituted haloalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group has been replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group have been replaced by halogen atoms. Unless otherwise specified in this specification, the number of carbon atoms in an "unsubstituted haloalkyl" group is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted haloalkyl" refers to a group in which one or more hydrogen atoms of a "haloalkyl" group have been replaced by a substituent. It should be noted that "substituted haloalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in a "substituted haloalkyl" group have been further replaced by a substituent, and groups in which one or more hydrogen atoms of a substituent in a "substituted haloalkyl" group have been further replaced by a substituent. As a specific example of "unsubstituted haloalkyl", examples can be given of groups in which one or more hydrogen atoms of the above-mentioned "alkyl" (specific example group G3) have been substituted with halogen atoms. Haloalkyl is sometimes called haloalkyl.
[0344] • "Substituted or unsubstituted alkoxy groups"
[0345] As a specific example of "substituted or unsubstituted alkoxy group" as described in this specification, it is the group indicated by -O (G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
[0346] • "Substituted or unsubstituted alkylthio groups"
[0347] As a specific example of "substituted or unsubstituted alkylthio group" as described in this specification, it is the group indicated by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
[0348] • "Substituted or unsubstituted aryloxy groups"
[0349] As a specific example of "substituted or unsubstituted aryloxy group" as described in this specification, it is the group indicated by -O (G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of carbon atoms in the ring 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.
[0350] • "Substituted or unsubstituted arylthio groups"
[0351] As a specific example of "substituted or unsubstituted arylthio group" as described in this specification, it is the group indicated by -S(G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of carbon atoms in the ring 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.
[0352] • "Substituted or unsubstituted trialkylsilyl groups"
[0353] As a specific example of "trialkylsilyl" as described in this specification, it is the group represented by -Si(G3)(G3)(G3), where G3 refers to the "substituted or unsubstituted alkyl" described in the specific example group G3. The plurality of G3s in -Si(G3)(G3)(G3) may be identical or different from each other. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the "trialkylsilyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.
[0354] • "Substituted or unsubstituted aralkyl groups"
[0355] As a specific example of "substituted or unsubstituted aralkyl" as described in this specification, it is the group shown as -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl" described in specific example group G3, and G1 is the "substituted or unsubstituted aryl" described in specific example group G1. Therefore, "aralkyl" is a group in which the hydrogen atom of "alkyl" is replaced by "aryl" as a substituent, and is one embodiment of "substituted alkyl". "Unsubstituted aralkyl" is an "unsubstituted alkyl" that is substituted with "unsubstituted aryl", and the number of carbon atoms of "unsubstituted aralkyl" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.
[0356] Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-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.
[0357] Unless otherwise specified in this specification, the substituted or unsubstituted aryl groups described herein are preferably phenyl, p-biphenyl, meta-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, meta-terphenyl-4-yl, meta-terphenyl-3-yl, meta-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthraceneyl, phenanthryl, pyrene, phenyl, triphenylene, fluorene, 9,9'-spirobisfluorene, 9,9-dimethylfluorene, and 9,9-diphenylfluorene, etc.
[0358] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic groups described herein are preferably pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, phenanthrolinel, carbazole (1-carbazole, 2-carbazole, 3-carbazole, 4-carbazole or 9-carbazole), benzocarbazole, azacarbazole, diazacarbazole, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophene, and naphtho-benzofuranyl. Benzothiophene, azadibenzothiophene, diazadibenzothiophene, (9-phenyl)carbazoyl ((9-phenyl)carbazo-1-yl, (9-phenyl)carbazo-2-yl, (9-phenyl)carbazo-3-yl or (9-phenyl)carbazo-4-yl), (9-biphenyl)carbazoyl, (9-phenyl)phenylcarbazoyl, diphenylcarbazo-9-yl, phenylcarbazo-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl and phenyldibenzothiophene, etc.
[0359] In this specification, the carbazoyl group, unless otherwise specified herein, specifically refers to any one of the following groups.
[0360]
[0361] In this specification, (9-phenyl)carbazolyl refers specifically to any one of the following groups unless otherwise specified herein.
[0362]
[0363] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.
[0364] In this specification, dibenzofuranyl and dibenzothiopheneyl are specifically any one of the following groups unless otherwise stated in this specification.
[0365]
[0366] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.
[0367] Unless otherwise specified in this specification, the substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and tert-butyl.
[0368] • "Substituted or unsubstituted aryl groups"
[0369] Unless otherwise stated, the "substituted or unsubstituted aryl group" described in this specification is a divalent group derived from the "substituted or unsubstituted aryl group" by removing one hydrogen atom from the aryl ring. Specific examples of "substituted or unsubstituted aryl group" (specific example group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in specific example group G1 by removing one hydrogen atom from the aryl ring.
[0370] • "Substituted or unsubstituted divalent heterocyclic groups"
[0371] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived from the aforementioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom from the heterocycle. Specific examples of "substituted or unsubstituted divalent heterocyclic groups" (specific example group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in specific example group G2 by removing one hydrogen atom from the heterocycle.
[0372] • "Substituted or unsubstituted alkylene compounds"
[0373] Unless otherwise stated, "substituted or unsubstituted alkylene groups" as described in this specification are divalent groups derived from "substituted or unsubstituted alkylene groups" by removing one hydrogen atom from the alkyl chain. Specific examples of "substituted or unsubstituted alkylene groups" (specific example group G14) include divalent groups derived from "substituted or unsubstituted alkylene groups" described in specific example group G3 by removing one hydrogen atom from the alkyl chain.
[0374] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described herein is preferably any one of the groups in the following general formulas (TEMP-42) to (TEMP-68).
[0375]
[0376]
[0377] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10Each can be a hydrogen atom or a substituent independently.
[0378] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.
[0379]
[0380] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.
[0381] Formulas Q9 and Q 10 They can form rings by bonding with each other via single bonds.
[0382] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.
[0383]
[0384] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.
[0385] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.
[0386] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described herein is preferably any group of the following general formulas (TEMP-69) to (TEMP-102).
[0387]
[0388]
[0389]
[0390] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.
[0391]
[0392]
[0393]
[0394]
[0395] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.
[0396] The above is an explanation of "substituents described in this specification".
[0397] • "Cases where bonds form rings"
[0398] In this specification, the description of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring, or bonded together to form a substituted or unsubstituted fused ring, or not bonded together" refers to the cases of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring", "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted fused ring", and "one or more groups of two or more adjacent elements not bonded together".
[0399] The following description addresses the cases described in this specification as "forming a substituted or unsubstituted monocyclic ring by bonding one or more groups of two or more adjacent elements together" and "forming a substituted or unsubstituted fused ring by bonding one or more groups of two or more adjacent elements together" (hereinafter, these cases are sometimes collectively referred to as "forming a ring by bonding"). The case of anthracene compounds represented by the following general formula (TEMP-103) with an anthracene ring as the parent skeleton will be used as an example.
[0400]
[0401] For example, in the case of R 921 ~R 930 In the case of "one or more groups of two or more adjacent elements bonded together to form a loop", a group consisting of two adjacent elements is referred to as R. 921 With R 922 group, R 922 With R 923 group, R 923 With R 924 group, R 924 With R 930 group, R 930 With R 925 group, R 925 With R 926 group, R 926 With R 927 group, R 927 With R 928 group, R 928 With R 929 The group, and R 929 With R 921 The group.
[0402] The phrase "one or more groups" refers to the fact that two or more of the aforementioned groups consisting of two or more adjacent elements can simultaneously form a loop. For example, in R... 921 With R 922 They bond together to form a ring Q A Moreover, R 925 With R 926 They bond together to form a ring Q B In this case, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).
[0403]
[0404] The formation of rings from "groups consisting of two or more adjacent elements" includes not only the case of bonds formed by groups consisting of "two" adjacent elements, as in the previous example, but also the case of bonds formed by groups consisting of "three or more" adjacent elements. For example, it refers to R... 921 With R 922 They bond together to form a ring Q A And R 922 With R 923 They bond together to form a ring Q C , consisting of 3 adjacent (R) 921 R 922 and R 923 When the groups of components Q bond together to form a ring and fuse to the anthracene matrix, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q... A and ring Q C There are a total of R 922 .
[0405]
[0406] In the formed "single ring" or "fused ring," the structure of the ring alone can be either a saturated ring or an unsaturated ring. Even when a "single ring" or "fused ring" is formed from "one group of two adjacent rings," the "single ring" or "fused ring" can still form a saturated ring or an unsaturated ring. For example, the ring Q formed in the above general formula (TEMP-104) A and ring Q B Each is either a "single ring" or a "fused ring". Additionally, the ring Q formed in the above general formula (TEMP-105) A and Q ring C It is a "fused ring". The ring Q of the above general formula (TEMP-105) A With ring Q C Through ring Q A With ring QC Fusing together forms a fused ring. The ring Q of the above general formula (TMEP-104) A If it is a benzene ring, then ring Q A It is a single ring. The ring Q in the above general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a fused ring.
[0407] "Unsaturated rings" refer to aromatic hydrocarbon rings or aromatic heterocycles. "Saturated rings" refer to aliphatic hydrocarbon rings or non-aromatic heterocycles.
[0408] As a specific example of an aromatic hydrocarbon ring, the structure formed by the hydrogen atom-terminated group in specific example group G1 can be cited.
[0409] As a specific example of an aromatic heterocycle, one can cite the structure formed by end-capping an aromatic heterocycle group with hydrogen atoms in specific example group G2.
[0410] As a specific example of an aliphatic hydrocarbon ring, the structure formed by the hydrogen atom-terminated group in specific example group G6 can be cited.
[0411] "Ring formation" refers to the formation of a ring solely by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton forming a ring with one or more other optional elements. For example, R shown in the above general formula (TEMP-104) 921 With R 922 The ring Q formed by mutual bonding A It refers to R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 The carbon atoms of the bonded anthracene framework form rings with one or more optional elements. As a specific example, in the case of R... 921 With R 922 Forming ring Q A In the case of R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 When the bonded anthracene skeleton carbon atoms and four carbon atoms form a monocyclic unsaturated ring, R 921 With R 922 The resulting ring is a benzene ring.
[0412] Here, "optional element" is preferably selected from at least one element chosen from the group consisting of carbon, nitrogen, oxygen, and sulfur, unless otherwise specified in this specification. In the case of optional elements (e.g., carbon or nitrogen), non-ring bonds can be capped by hydrogen atoms or replaced by "optional substituents" described later. When optional elements other than carbon are included, the resulting ring is a heterocycle.
[0413] Unless otherwise specified in this specification, the "one or more optional elements" constituting a monocyclic or fused ring are preferably two or more and 15 or less, more preferably three or more and 12 or less, and even more preferably three or more and 5 or less.
[0414] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".
[0415] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".
[0416] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.
[0417] Unless otherwise stated in this specification, the "unsaturated ring" is preferably a benzene ring.
[0418] In the case of “one or more groups consisting of two or more adjacent elements”, “forming a substituted or unsubstituted monocyclic ring by mutual bonding”, or “forming a substituted or unsubstituted fused ring by mutual bonding”, unless otherwise stated in this specification, it is preferred that one or more groups consisting of two or more adjacent elements are mutually bonded to form a substituted or unsubstituted “unsaturated ring” consisting of a plurality of atoms of a parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur.
[0419] When the aforementioned "monocyclic" or "fused-ring" rings have substituents, the substituents are, for example, the "optional substituents" described later. Specific examples of substituents when the aforementioned "monocyclic" or "fused-ring" rings have substituents are the substituents described in the section "Substituents Represented in This Specification" above.
[0420] When the aforementioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of substituents when the aforementioned "monocyclic" or "fused ring" has a substituent are the substituents described in the section "Substituents Represented in This Specification" above.
[0421] The above explains the cases of "a single ring formed by bonding one or more groups of two or more adjacent elements together" and "a fused ring formed by bonding one or more groups of two or more adjacent elements together" ("the case of forming a ring by bonding").
[0422] Substituents when described as "substituted or unsubstituted"
[0423] In one embodiment of this specification, the substituents described above as "substituted or unsubstituted" (sometimes referred to as "optional substituents" in this specification) are, for example, selected from...
[0424] Unsubstituted alkyl groups having 1 to 50 carbon atoms
[0425] Unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0426] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms
[0427] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0428] -Si(R 901 (R) 902 (R) 903 ),
[0429] -O-(R 904 ),
[0430] -S-(R 905 ),
[0431] -N(R 906 (R) 907 ),
[0432] Halogen atom, cyano group, nitro group,
[0433] Unsubstituted aryl groups with 6 to 50 carbon atoms and
[0434] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms
[0435] Groups, etc., in the composition group
[0436] Here, R 901 ~R 907 Each independently
[0437] hydrogen atom,
[0438] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0439] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0440] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0441] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[0442] In R 901 When there are more than two, more than two R 901 They are the same or different.
[0443] In R902 When there are more than two, more than two R 902 They are the same or different.
[0444] In R 903 When there are more than two, more than two R 903 They are the same or different.
[0445] In R 904 When there are more than two, more than two R 904 They are the same or different.
[0446] In R 905 When there are more than two, more than two R 905 They are the same or different.
[0447] In R 906 When there are more than two, more than two R 906 They are the same or different.
[0448] In R 907 When there are more than two, more than two R 907 They are the same or different.
[0449] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.
[0450] Alkyl groups with 1 to 50 carbon atoms
[0451] Aryl groups with 6 to 50 carbon atoms and
[0452] Groups in the group consisting of heterocyclic groups with 5 to 50 cyclic atoms.
[0453] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.
[0454] Alkyl groups having 1 to 18 carbon atoms
[0455] aryl groups with 6 to 18 carbon atoms and
[0456] Groups in the group consisting of heterocyclic groups with 5 to 18 cyclic atoms.
[0457] Specific examples of the substituents mentioned above are those described in the section "Substituents as set forth in this specification".
[0458] Unless otherwise stated in this specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring" with each other, preferably forming a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably forming a benzene ring.
[0459] Unless otherwise stated in this specification, optional substituents may also have other substituents. Any further substituents that may be present as optional substituents are the same as those described above.
[0460] In this specification, the numerical range represented by "AA~BB" refers to the range included by taking the value AA, which is written before "AA~BB", as the lower limit and the value BB, which is written after "AA~BB", as the upper limit.
[0461] [First Implementation]
[0462] Organic electroluminescent devices
[0463] The organic electroluminescent element according to the first embodiment has an anode, a cathode, and two or more light-emitting units disposed between the anode and the cathode.
[0464] The aforementioned two or more light-emitting units include at least a first light-emitting unit having a first light-emitting region and a second light-emitting unit having a second light-emitting region.
[0465] The anode, the first light-emitting unit, the second light-emitting unit, and the cathode are arranged sequentially from the anode side toward the cathode side.
[0466] The aforementioned first luminescent region includes a first luminescent layer containing a first host material and a second luminescent layer containing a second host material.
[0467] The first light-emitting layer is disposed closer to the anode side than the second light-emitting layer.
[0468] The aforementioned second luminescent region includes a third luminescent layer containing a third host material and a fourth luminescent layer containing a fourth host material.
[0469] The third light-emitting layer is disposed closer to the anode side than the fourth light-emitting layer.
[0470] The first, second, third, and fourth light-emitting layers each independently contain a luminescent compound exhibiting a maximum peak wavelength of less than 500 nm.
[0471] The first main material mentioned above is different from the third main material mentioned above.
[0472] The first main material mentioned above is different from the second and fourth main materials mentioned above.
[0473] The third main material mentioned above differs from the second and fourth main materials mentioned above.
[0474] The second main material mentioned above may be the same as or different from the fourth main material mentioned above.
[0475] The triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material satisfy the following mathematical expression (Mathematical Expression 1).
[0476] The triplet energy T1(H3) of the third host material and the triplet energy T1(H4) of the fourth host material satisfy the following mathematical formula (Mathematical Formula 2).
[0477] T1(H1)>T1(H2) …(Mathematical Expression 1)
[0478] T1(H3)>T1(H4) …(Mathematical expression 2).
[0479] In this specification, an organic electroluminescent element having two or more light-emitting units disposed between the anode and the cathode is sometimes referred to as a tandem organic electroluminescent element (tandem organic EL element). Additionally, in this specification, a light-emitting unit comprising multiple stacked light-emitting layers is sometimes referred to as a stacked light-emitting unit.
[0480] The organic EL element involved in this embodiment can improve luminous efficiency by satisfying mathematical formulas (Mathematical Formula 1) and (Mathematical Formula 2).
[0481] Previously, Triplet-Triplet-Annihilation (sometimes called TTA) was known as a technique for improving the luminescence efficiency of organic EL devices. TTA is a mechanism in which triplet excitons collide with each other to generate singlet excitons. It should be noted that the TTA mechanism is sometimes also referred to as the TTF mechanism.
[0482] The TTF phenomenon is explained. Holes injected from the anode recombine with electrons injected from the cathode within the emissive layer to generate excitons. Their spin states, as previously known, are 25% singlet excitons and 75% triplet excitons. In previously known fluorescent elements, 25% of the singlet excitons relax to the ground state and emit light, while the remaining 75% of the triplet excitons do not emit light but recover to the ground state through thermal deactivation. Therefore, the theoretical limit of the internal quantum efficiency of previous fluorescent elements was claimed to be 25%.
[0483] On the other hand, the behavior of triplet excitons generated within organic matter has been theoretically studied. According to SMBachilo et al. (J. Phys. Chem. A, 104, 7711 (2000)), if we assume that excitons of higher orders, such as quintet, immediately revert to the triplet state, then in triplet excitons (hereinafter referred to as...) 3 A * As the density of ) gradually increases, triplet excitons collide with each other, resulting in the reaction shown in the following equation. Here, 1 A represents the ground state. 1 A * This represents the lowest excited singlet exciton.
[0484] 3 A * + 3 A * →(4 / 9) 1 A + (1 / 9) 1 A * +(13 / 9) 3 A *
[0485] That is, to become 5 3 A * →4 1 A+1A * It is predicted that of the initially generated 75% of triplet excitons, 1 / 5, or 20%, will transform into singlet excitons. Therefore, the singlet excitons contributing in the form of light become 40%, which is the initial 25% plus 75% × (1 / 5) = 15%. At this point, the proportion of light emitted from TTF (TTF ratio) in the total luminescence intensity becomes 15 / 40, or 37.5%. Furthermore, if the initially generated 75% of triplet excitons collide with each other to generate singlet excitons (two triplet excitons generate one singlet exciton), a very high internal quantum efficiency of 62.5% can be obtained, which is the initial 25% of singlet excitons plus 75% × (1 / 2) = 37.5%. At this point, the TTF ratio is 37.5 / 62.5 = 60%.
[0486] According to the organic EL element of this embodiment, it is believed that for triplet excitons generated by the recombination of holes and electrons in the first light-emitting layer of the first light-emitting unit, even if there are excess carriers at the interface between the first light-emitting layer and the directly connected organic layer, the triplet excitons at the interface between the first light-emitting layer and the organic layer are not easily quenched. For example, if 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 due to excess electrons can be considered. On the other hand, if 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 due to excess holes can be considered.
[0487] In the organic EL element of this embodiment, the first light-emitting unit includes at least two light-emitting layers (i.e., the first light-emitting layer and the second light-emitting layer) that satisfy a specified relationship. 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 mathematical formula (mathematical formula 1).
[0488] By having a first luminescent unit comprising a first luminescent layer and a second luminescent layer satisfying the aforementioned mathematical formula (Formula 1), triplet excitons generated in the first luminescent layer are not quenched by excess carriers and migrate to the second luminescent layer. Furthermore, reverse migration from the second luminescent layer to the first luminescent layer is suppressed. As a result, the second luminescent layer exhibits a TTF mechanism, efficiently generating singlet excitons and improving luminescence efficiency.
[0489] Thus, the light-emitting unit in the organic electroluminescent element has a first light-emitting layer that mainly generates triplet excitons and a second light-emitting layer that effectively utilizes the triplet excitons that move from the first light-emitting layer and mainly exhibits the TTF mechanism as different regions. As the second host material in the second light-emitting layer, a compound with a smaller triplet energy than the first host material in the first light-emitting layer is used to set the triplet energy difference, thereby improving the luminous efficiency.
[0490] The organic EL element involved in this embodiment also has a second light-emitting unit. The second light-emitting unit includes a third light-emitting layer and a fourth light-emitting layer that satisfy the relationship described above in mathematical formula (Mathematical Formula 2). The description of the correlation between the first and second light-emitting layers in the first light-emitting unit, the manifestation of the TTF mechanism, and the improvement of luminous efficiency also applies to the third and fourth light-emitting layers in the second light-emitting unit. By satisfying the mathematical formula (Mathematical Formula 2) between the third and fourth host materials, the luminous efficiency is improved.
[0491] In this embodiment, it is preferable that the triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material satisfy the following mathematical formula (Mathematical Formula 1A).
[0492] T1(H1)-T1(H2)>0.03eV …(Mathematical Formula 1A)
[0493] In this embodiment, it is preferable that the triplet energy T1(H3) of the third host material and the triplet energy T1(H4) of the fourth host material satisfy the following mathematical formula (Mathematical Formula 2A).
[0494] T1(H3)-T1(H4)>0.03eV …(Mathematical expression 2A)
[0495] According to this embodiment, an organic EL element with improved component performance can be provided.
[0496] In the organic EL element of this embodiment, the charge balance is optimized and the performance of the organic EL element is improved because the first host material in the first light-emitting layer of the first light-emitting unit and the third host material in the third light-emitting layer of the second light-emitting unit are different compounds.
[0497] According to one embodiment of the organic EL element, the luminous efficiency and lifetime of the organic EL element are improved.
[0498] In one embodiment of this invention, the triplet energy T1(H1) of the first host material and the triplet energy T1(H3) of the third host material satisfy the following mathematical formula (Formula 3A), (Formula 3B), or (Formula 3C).
[0499] T1(H1)>T1(H3) …(Mathematical expression 3A)
[0500] T1(H1) = T1(H3) …(Mathematical expression 3B)
[0501] T1(H1)<T1(H3) …(Mathematical expression 3C)
[0502] In one embodiment of this invention, the triplet energy T1(H2) of the second host material and the triplet energy T1(H4) of the fourth host material satisfy the following mathematical formula (Formula 4A), (Formula 4B), or (Formula 4C).
[0503] T1(H2)>T1(H4) …(Mathematical expression 4A)
[0504] T1(H2) = T1(H4) …(Mathematical expression 4B)
[0505] T1(H2)<T1(H4) …(Mathematical expression 4C)
[0506] <Light-emitting unit>
[0507] The organic EL element involved in this embodiment is an element that includes two or more light-emitting units between the anode and the cathode. The two or more light-emitting units include at least a first light-emitting unit and a second light-emitting unit. For example, three or more light-emitting units may be included between the anode and the cathode. That is, in the organic EL element involved in this embodiment, the two or more light-emitting units can be three or more light-emitting units, and in this case, the three or more light-emitting units include at least a first light-emitting unit, a second light-emitting unit, and a third light-emitting unit.
[0508] In the organic EL element of this embodiment, it is preferable that a first light-emitting unit is disposed between the anode and the cathode, and a second light-emitting unit is disposed between the first light-emitting unit and the cathode. In this embodiment, it is preferable that the first light-emitting unit among the two or more light-emitting units is the light-emitting unit closest to the anode.
[0509] As a counting method for multiple light-emitting units disposed between the anode and cathode, for example, when N light-emitting units are disposed between the anode and cathode, they are sometimes counted sequentially from the light-emitting unit closest to the anode as level 1, level 2, level 3, ..., level (N-1), level N. The organic EL element according to this embodiment, which includes two or more light-emitting units, includes at least level 1 and level 2 light-emitting units. In one aspect of this embodiment, it is preferred that the first light-emitting unit is the level 1 light-emitting unit closest to the anode, and the second light-emitting unit is the level 2 light-emitting unit.
[0510] Organic EL devices typically have one or more light-emitting units, each of which independently comprises one or more layers, at least one of which is a light-emitting layer. In addition to the light-emitting layer, each light-emitting unit of an organic EL device may also have one or more layers containing at least one of organic compounds and inorganic substances. The inorganic substance may be at least one of inorganic compounds and elements. Preferably, each light-emitting unit independently comprises one or more layers selected from those composed solely of organic compounds, those composed solely of inorganic substances, and those composed of both organic compounds and inorganic substances. Examples of layers that may be included in each light-emitting unit besides the light-emitting layer include those suitable for organic EL devices. There is no particular limitation on the layers suitable for use in organic EL devices besides the light-emitting layer, but preferably, each light-emitting unit independently comprises at least one layer selected from, for example, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
[0511] <Emitting Area>
[0512] (First, second, third, and fourth light-emitting layers)
[0513] In the organic EL element according to this embodiment, the first light-emitting unit has a first light-emitting region, and the second light-emitting unit has a second light-emitting region. In this embodiment, the first light-emitting region and the second light-emitting region each independently contain two or more light-emitting layers.
[0514] The first luminescent region includes a first luminescent layer containing a first host material and a second luminescent layer containing a second host material. The first luminescent layer is disposed closer to the anode than the second luminescent layer. The first luminescent layer is disposed between the anode and the second luminescent layer. Preferably, the first luminescent layer is the layer closest to the anode among the plurality of layers in the first luminescent region, and the second luminescent layer is the layer closest to the cathode among the plurality of layers in the first luminescent region.
[0515] The second light-emitting region includes a third light-emitting layer containing a third host material and a fourth light-emitting layer containing a fourth host material. The third light-emitting layer is disposed closer to the anode side than the fourth light-emitting layer. The fourth light-emitting layer is disposed between the third light-emitting layer and the cathode. Preferably, the third light-emitting layer is the layer closest to the anode among the multiple layers of the second light-emitting region, and the fourth light-emitting layer is the layer closest to the cathode among the multiple layers of the second light-emitting region.
[0516] In this specification, "the first light-emitting layer, the second light-emitting layer, the third light-emitting layer and the fourth light-emitting layer" are sometimes referred to as "the first, the second, the third and the fourth light-emitting layers".
[0517] In this embodiment, preferably, at least one of the light-emitting layers selected from the group consisting of the first, second, third, and fourth light-emitting layers does not contain a metal complex. Preferably, none of the first, second, third, and fourth light-emitting layers contain a metal complex.
[0518] In this embodiment, preferably, at least one of the light-emitting layers selected from the group consisting of the first, second, third, and fourth light-emitting layers does not contain boron-containing complexes. Preferably, none of the first, second, third, and fourth light-emitting layers contain boron-containing complexes.
[0519] In this embodiment, preferably, at least one of the light-emitting layers selected from the group consisting of the first, second, third, and fourth light-emitting layers does not contain phosphorescent materials. Preferably, none of the first, second, third, and fourth light-emitting layers contain phosphorescent materials.
[0520] In this embodiment, it is also preferred that at least one of the light-emitting layers selected from the group consisting of the first, second, third, and fourth light-emitting layers does not contain heavy metal complexes or phosphorescent rare earth metal complexes. Preferably, all of the first, second, third, and fourth light-emitting layers do not contain heavy metal complexes or phosphorescent rare earth metal complexes.
[0521] In this embodiment, it is also preferable that at least one of the light-emitting layers selected from the group consisting of the first, second, third, and fourth light-emitting layers does not contain heavy metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Preferably, none of the first, second, third, and fourth light-emitting layers contains heavy metal complexes such as iridium complexes, osmium complexes, and platinum complexes.
[0522] (Main material)
[0523] Each light-emitting layer within the light-emitting region independently contains a host material. In this specification, "host material" refers to, for example, a material with a content of "50% by mass or more of the layer." For example, preferably, the content of the host material in each light-emitting layer within the light-emitting region is independently 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more. Furthermore, for example, the content of the host material in each light-emitting layer within the light-emitting region is preferably independently 99.5% by mass or less, or 99% by mass or less.
[0524] In this embodiment, the first, second, third, and fourth light-emitting layers respectively contain a first main material, a second main material, a third main material, and a fourth main material as main materials. In this specification, "the first main material, the second main material, the third main material, and the fourth main material" are sometimes referred to as "the first, second, third, and fourth main materials".
[0525] In this embodiment, it is preferred that the host material contained in each light-emitting layer (preferably the first, second, third and fourth host materials) is each independently selected from the group consisting of the compound shown in formula (2), the compound shown in formula (H11), the compound shown in formula (H12), the compound shown in formula (H13), the compound shown in formula (H14), the compound shown in formula (H15), the compound shown in formula (H16), the compound shown in formula (H17), the compound shown in formula (H18) and the compound shown in formula (H19).
[0526] (Main Material 1 and Main Material 3)
[0527] In this embodiment, the first main material and the third main material are different from each other.
[0528] In this embodiment, the first main material is different from the second and fourth main materials.
[0529] In this embodiment, the third body material is different from the second and fourth body materials.
[0530] In this embodiment, preferably, at least one of the first main material and the third main material is any one of the compounds selected from the group consisting of the compound shown in formula (H11), the compound shown in formula (H12), the compound shown in formula (H13), the compound shown in formula (H14), the compound shown in formula (H15), the compound shown in formula (H16), the compound shown in formula (H17), the compound shown in formula (H18), and the compound shown in formula (H19).
[0531] In this embodiment, preferably, the first main material is any one of the compounds selected from the group consisting of the compound shown in formula (H11), the compound shown in formula (H12), the compound shown in formula (H13), the compound shown in formula (H14), the compound shown in formula (H15), the compound shown in formula (H16), the compound shown in formula (H17), the compound shown in formula (H18), and the compound shown in formula (H19).
[0532] In this embodiment, it is preferred that the third main material is any one of the compounds selected from the group consisting of the compound shown in formula (H11), the compound shown in formula (H12), the compound shown in formula (H13), the compound shown in formula (H14), the compound shown in formula (H15), the compound shown in formula (H16), the compound shown in formula (H17), the compound shown in formula (H18), and the compound shown in formula (H19).
[0533] In this embodiment, preferably, the first main material and the third main material are each independently selected from the group consisting of the compound shown in formula (H11), the compound shown in formula (H12), the compound shown in formula (H13), the compound shown in formula (H14), the compound shown in formula (H15), the compound shown in formula (H16), the compound shown in formula (H17), the compound shown in formula (H18), and the compound shown in formula (H19).
[0534]
[0535] (In the above formula (H11),
[0536] R 101 ~R 110 and R 111 ~R 120 Each independently
[0537] hydrogen atom,
[0538] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0539] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0540] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0541] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0542] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0543] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0544] -O-(R 904 The groups shown in the figure,
[0545] -S-(R 905 The groups shown in the figure,
[0546] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0547] -C(=O)R 801 The groups shown
[0548] -COOR 802 The groups shown
[0549] Halogen atoms,
[0550] cyano,
[0551] Nitro,
[0552] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0553] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0554] Among them, R 101 ~R 110 One of them represents L 101 The bonding position, R 111 ~R 120 One of them represents L 101 The bonding position,
[0555] L 101 for
[0556] single bond,
[0557] Substituted or unsubstituted arylene groups with 6 to 24 carbon atoms, or
[0558] Divalent heterocyclic groups with 5–24 cyclic atoms, substituted or unsubstituted.
[0559] mx is 0, 1, 2, 3, 4, or 5.
[0560] In L 101 When there are more than two, more than two L 101 (They may be the same or different.)
[0561] In the above formula (H11), R 101 ~R 110 and R 111 ~R 120 Two or more adjacent groups are not bonded to each other.
[0562]
[0563] (In the above formula (H12),
[0564] Xa represents oxygen atoms, sulfur atoms, and C(R) atoms. 1201 (R) 1202 ) or Si(R 1203 (R) 1204 ),
[0565] R 1201 ~R 1204 Each independently
[0566] hydrogen atom,
[0567] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0568] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0569] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0570] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0571] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0572] -O-(R 904 The groups shown in the figure,
[0573] -S-(R 905 The groups shown in the figure,
[0574] -N(R 906 (R) 907 The groups shown in the figure,
[0575] Halogen atoms,
[0576] cyano,
[0577] Nitro,
[0578] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0579] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0580] By R 121 ~R 130 One or more groups consisting of two or more adjacent elements.
[0581] They bond together to form substituted or unsubstituted monocyclic rings.
[0582] They bond together to form substituted or unsubstituted fused rings, or
[0583] They do not bond with each other.
[0584] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 121 ~R 130 Each independently
[0585] hydrogen atom,
[0586] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0587] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0588] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0589] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0590] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0591] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0592] -O-(R 904 The groups shown in the figure,
[0593] -S-(R 905 The groups shown in the figure,
[0594] -N(R 906 (R) 907 The groups shown in the figure,
[0595] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0596] -C(=O)R 801 The groups shown
[0597] -COOR 802 The groups shown
[0598] Halogen atoms,
[0599] Nitro,
[0600] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[0601] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[0602] The group represented by the above formula (H121),
[0603] Among them, R 121 ~R 130 At least one of them is a group represented by the above formula (H121),
[0604] When multiple groups represented by the above formula (H121) exist, the multiple groups represented by the above formula (H121) may be the same as or different from each other.
[0605] L 12 for
[0606] single bond,
[0607] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[0608] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0609] ma is 0, 1, 2, or 3.
[0610] In L 12 When there are more than two, more than two L 12 They are the same or different.
[0611] Ar 12 It is an aryl group with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted, or a heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[0612] In Ar 12 In the case of two or more Ar, two or more Ar 12 They are the same or different.
[0613] In the above formula (H121), * indicates the bonding location.
[0614]
[0615] (In the above formula (H13),
[0616] By R 131 ~R134 and R 139 ~R 140 One or more groups consisting of two or more adjacent elements.
[0617] They bond together to form substituted or unsubstituted monocyclic rings, or
[0618] They do not bond with each other.
[0619] By R 135 ~R 138 One or more groups consisting of two or more adjacent elements.
[0620] They bond together to form substituted or unsubstituted monocyclic rings, or
[0621] They do not bond with each other.
[0622] Ar 131 Ar 132 R and the monocyclic compounds that do not form the aforementioned substituted or unsubstituted ones 131 ~R 140 Each independently
[0623] hydrogen atom,
[0624] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0625] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0626] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0627] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0628] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0629] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0630] -O-(R 904 The groups shown in the figure,
[0631] -S-(R 905 The groups shown in the figure,
[0632] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0633] -C(=O)R 801 The groups shown
[0634] -COOR 802 The groups shown
[0635] Halogen atoms,
[0636] cyano,
[0637] Nitro,
[0638] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[0639] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[0640] The group represented by the above formula (H131),
[0641] Among them, R 131 ~R 140 Ar 131 and Ar 132 At least one of them is a group represented by the above formula (H131),
[0642] When multiple groups represented by the above formula (H131) exist, the multiple groups represented by the above formula (H131) may be the same as or different from each other.
[0643] L 13 for
[0644] single bond,
[0645] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[0646] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0647] Ar 13 for
[0648] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0649] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0650] mb can be 0, 1, 2, 3, 4, or 5.
[0651] In L 13 When there are more than two, more than two L 13 They are the same or different.
[0652] In Ar 13 In the case of two or more Ar, two or more Ar 13 They are the same or different.
[0653] In formula (H131) above, * indicates the bonding position with the benzo[a]anthracene ring in formula (H13) above.
[0654]
[0655] (In the above formula (H14),
[0656] R 1A and R 1B Each independently
[0657] Substituted or unsubstituted alkyl groups having 1 to 15 carbon atoms
[0658] Substituted or unsubstituted aryl groups with 6 to 17 carbon atoms, or
[0659] Heterocyclic groups with 5 to 17 cyclic atoms, substituted or unsubstituted.
[0660] Among them, R 1A and R 1B At least one of them is a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms.
[0661] By R 141 ~R 144 A group consisting of two or more adjacent elements and R 145 ~R 148 Any group consisting of two or more adjacent elements
[0662] They bond together to form substituted or unsubstituted monocyclic rings, or
[0663] They bond together to form substituted or unsubstituted fused rings.
[0664] In the case where a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring is formed on the ring A side, the group shown in formula (H141) above is bonded to R. 142 The carbon atom of ring A that is bonded, or the carbon atom of the single ring and the fused ring on the side of ring A that are bonded to the carbon atom C2 on the side of ring B, is the carbon atom of ring A that is furthest from the carbon atom C1 on the side of ring B.
[0665] In the case where the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted fused ring is formed on the ring B side instead of on ring A, the group shown in formula (H141) above is bonded to R. 142 Bonded carbon atoms,
[0666] R is not the group represented by the above formula (H141) 142 R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 141 R 143 R 144 and R 145 ~R 148 Each independently
[0667] hydrogen atom,
[0668] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0669] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0670] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0671] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0672] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0673] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0674] -O-(R 904 The groups shown in the figure,
[0675] -S-(R 905 The groups shown in the figure,
[0676] -N(R 906 (R) 907 The groups shown in the figure,
[0677] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0678] -C(=O)R 801 The groups shown
[0679] -COOR 802 The groups shown
[0680] Halogen atoms,
[0681] cyano,
[0682] Nitro,
[0683] Substituted or unsubstituted aryl groups with 6 to 17 carbon atoms, or
[0684] Heterocyclic groups with 5 to 17 cyclic atoms, substituted or unsubstituted.
[0685] In the above formula (H141),
[0686] Ar 14 It is a substituted or unsubstituted aryl group fused with four or more rings, or a substituted or unsubstituted heterocyclic group fused with four or more rings.
[0687] L 14 for
[0688] single bond,
[0689] Substituted or unsubstituted arylene groups with 6 to 17 carbon atoms, or
[0690] Divalent heterocyclic groups with 5–17 cyclic atoms, substituted or unsubstituted.
[0691] mc is 0, 1, or 2.
[0692] * indicates the bonding position of the atom that forms the ring in the above formula (H14).
[0693] Specifically, for the compound represented by formula (H14) above, the molecule of the compound represented by formula (H14) contains no more than three substituted or unsubstituted aryl groups with four or more fused rings and no more than three substituted or unsubstituted heterocyclic groups with four or more fused rings.
[0694]
[0695] (In the above formula (H15),
[0696] R 150 ~R 159 Each independently
[0697] hydrogen atom,
[0698] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0699] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0700] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0701] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0702] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0703] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0704] -O-(R 904 The groups shown in the figure,
[0705] -S-(R 905 The groups shown in the figure,
[0706] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0707] -C(=O)R 801 The groups shown
[0708] -COOR 802The groups shown
[0709] Halogen atoms,
[0710] cyano,
[0711] Nitro,
[0712] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[0713] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[0714] The group represented by the above formula (H150),
[0715] Among them, R 150 ~R 159 At least one of them is a group represented by the above formula (H150).
[0716] When multiple groups represented by the above formula (H150) are present, the multiple groups represented by the above formula (H150) may be the same as or different from each other.
[0717] L 151 for
[0718] single bond,
[0719] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[0720] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0721] Ar 151 for
[0722] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0723] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0724] mg is 0, 1, 2, 3, 4 or 5,
[0725] In L 151 When there are more than two, more than two L 151 They are the same or different.
[0726] In Ar 151 In the case of two or more Ar, two or more Ar 151 They are the same or different.
[0727] In the above formula (H150), the asterisk (*) indicates the bonding position with the pyrene ring in formula (H15).
[0728] In the above formula (H15), R 150 ~R159 Two or more adjacent groups are not bonded to each other.
[0729]
[0730] (In the above formula (H16),
[0731] By R 160 ~R 169 One or more groups consisting of two or more adjacent elements.
[0732] They bond together to form substituted or unsubstituted monocyclic rings.
[0733] They bond together to form substituted or unsubstituted fused rings, or
[0734] They do not bond with each other.
[0735] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 160 ~R 169 Each independently
[0736] hydrogen atom,
[0737] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0738] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0739] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0740] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0741] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0742] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0743] -O-(R 904 The groups shown in the figure,
[0744] -S-(R 905 The groups shown in the figure,
[0745] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0746] -C(=O)R 801 The groups shown
[0747] -COOR 802 The groups shown
[0748] Halogen atoms,
[0749] cyano,
[0750] Nitro,
[0751] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[0752] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[0753] The group represented by the above formula (H161),
[0754] Wherein, the substituent when the aforementioned substituted or unsubstituted monocyclic ring has a substituent, the substituent when the aforementioned substituted or unsubstituted fused ring has a substituent, and R 160 ~R 169 At least one of them is a group represented by the above formula (H161),
[0755] When multiple groups represented by the above formula (H161) are present, the multiple groups represented by the above formula (H161) may be the same as or different from each other.
[0756] L 16 for
[0757] single bond,
[0758] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[0759] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0760] Ar 16 for
[0761] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0762] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0763] mf is 0, 1, 2, 3, 4 or 5.
[0764] In L 16 When there are more than two, more than two L 16 They are the same or different.
[0765] In Ar 16 In the case of two or more Ar, two or more Ar 16 They are the same or different.
[0766] In equation (H161) above, * indicates the bonding position with the ring shown in equation (H16) above.
[0767]
[0768] (In the above formula (H17),
[0769] From Rb1 to Rb 14 One or more groups consisting of two or more adjacent elements.
[0770] They bond together to form substituted or unsubstituted monocyclic rings.
[0771] They bond together to form substituted or unsubstituted fused rings, or
[0772] They do not bond with each other.
[0773] Rb1 to Rb do not form the aforementioned substituted or unsubstituted monocyclic rings and do not form the aforementioned substituted or unsubstituted fused rings. 14 Each independently
[0774] hydrogen atom,
[0775] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0776] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0777] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0778] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0779] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0780] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0781] -O-(R 904 The groups shown in the figure,
[0782] -S-(R 905 The groups shown in the figure,
[0783] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0784] -C(=O)R 801 The groups shown
[0785] -COOR 802 The groups shown
[0786] Halogen atoms,
[0787] cyano,
[0788] Nitro,
[0789] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[0790] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[0791] The group represented by the above formula (H171),
[0792] Wherein, the substituent when the aforementioned substituted or unsubstituted monocyclic ring has a substituent, the substituent when the aforementioned substituted or unsubstituted fused ring has a substituent, and Rb1 to Rb 14 At least one of them is a group represented by the above formula (H171).
[0793] When multiple groups represented by the above formula (H171) are present, the multiple groups represented by the above formula (H171) may be the same as or different from each other.
[0794] L 17 for
[0795] single bond,
[0796] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[0797] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0798] Ar 17 for
[0799] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0800] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0801] mg is 0, 1, 2, 3, 4 or 5,
[0802] In L 17 When there are more than two, more than two L 17 They are the same or different.
[0803] In Ar 17 In the case of two or more Ar, two or more Ar 17 They are the same or different.
[0804] In equation (H171) above, * indicates the bonding position with the ring shown in equation (H17) above.
[0805]
[0806] (In the above formula (H18),
[0807] Re1~Re 14 Each independently
[0808] hydrogen atom,
[0809] Substituted or unsubstituted aryl groups with 6 to 22 carbon atoms
[0810] Substituted or unsubstituted heterocyclic groups with 5 to 22 cyclic atoms, or
[0811] The group represented by the above formula (H18a),
[0812] Re1~Re 14 At least one of them is a group other than a hydrogen atom.
[0813] In the above formula (H18a), Le is
[0814] single bond,
[0815] Substituted or unsubstituted arylene groups with 6 to 22 carbon atoms, or
[0816] Divalent heterocyclic groups with 5–22 cyclic atoms, substituted or unsubstituted.
[0817] Are for
[0818] Substituted or unsubstituted aryl groups with 6 to 22 carbon atoms, or
[0819] Heterocyclic groups with 5 to 22 cyclic atoms, substituted or unsubstituted.
[0820] * indicates the bonding location.
[0821] Preferably, the compound represented by the above formula (H18) does not have substituted or unsubstituted amino groups, substituted or unsubstituted carbazole groups, and substituted or unsubstituted indole groups in the molecule.
[0822] In this embodiment, Re3 and Re are preferred. 12 At least one of them is
[0823] Substituted or unsubstituted aryl groups with 6 to 22 carbon atoms
[0824] Substituted or unsubstituted heterocyclic groups with 5 to 22 cyclic atoms, or
[0825] The group represented by the above formula (H18a).
[0826] In this embodiment, it is preferred that Re1 and Re 14 At least one of them is
[0827] Substituted or unsubstituted aryl groups with 6 to 22 carbon atoms
[0828] Substituted or unsubstituted heterocyclic groups with 5 to 22 cyclic atoms, or
[0829] The group represented by the above formula (H18a).
[0830] In this embodiment, preferably, Re3 is a substituted or unsubstituted aryl group with 6 to 22 cyclic carbon atoms, a substituted or unsubstituted heterocyclic group with 5 to 22 cyclic atoms, or a group represented by the above formula (H18a), and Re1, Re2, and Re4 to Re 14 It is a hydrogen atom.
[0831] Preferably, the heterocyclic group with 5 to 22 cyclic atoms in the compound represented by formula (H18) is a group containing one or more oxygen atoms.
[0832] Preferably, the heterocyclic group with 5 to 22 cyclic atoms in the compound represented by formula (H18) is a group that does not contain an azazine ring.
[0833] Preferably, the compound represented by the above formula (H18) does not contain an azazine ring in its molecule.
[0834]
[0835] (In the above formula (H19),
[0836] Rd1~Rd 14 Each independently
[0837] hydrogen atom,
[0838] Substituted or unsubstituted aryl groups with 6 to 22 carbon atoms
[0839] Substituted or unsubstituted heterocyclic groups with 5 to 22 cyclic atoms, or
[0840] The group represented by the above formula (H19a),
[0841] Rd1~Rd 14 At least one of them is a group other than a hydrogen atom.
[0842] In the above equation (H19a), Ld is
[0843] single bond,
[0844] Substituted or unsubstituted arylene groups with 6 to 22 carbon atoms, or
[0845] Divalent heterocyclic groups with 5–22 cyclic atoms, substituted or unsubstituted.
[0846] Ard is
[0847] Substituted or unsubstituted aryl groups with 6 to 22 carbon atoms, or
[0848] Heterocyclic groups with 5 to 22 cyclic atoms, substituted or unsubstituted.
[0849] * indicates the bonding location.
[0850] Preferably, the compound represented by the above formula (H19) does not have substituted or unsubstituted amino groups, substituted or unsubstituted carbazole groups, and substituted or unsubstituted indole groups in the molecule.
[0851] In this embodiment, Rd4, Rd7, and Rd are preferred. 11 and Rd 14 At least one of them is an aryl group with 6 to 22 carbon atoms that is substituted or unsubstituted, a heterocyclic group with 5 to 22 carbon atoms that is substituted or unsubstituted, or a group represented by the above formula (H19a).
[0852] Through Rd4, Rd7, Rd 11 and Rd 14 If at least one of the groups is an aryl, heterocyclic, or a group represented by the above formula (H19a), the compound represented by formula (H19) can be easily synthesized, and the molecular weight of the compound can also be easily adjusted. In Rd4, Rd7, Rd... 11 and Rd 14 When at least one of the compounds is an aryl, heterocyclic, or group represented by the above formula (H19a), the chromaticity deterioration of the organic EL element containing the compound represented by formula (H19) is easily suppressed, and it is easy to emit light with good chromaticity.
[0853] In this embodiment, it is preferred that Rd1, Rd4, Rd6, Rd7, Rd8, and Rd 11 、Rd 13 and Rd 14 At least one of them is
[0854] Substituted or unsubstituted aryl groups with 6 to 22 carbon atoms
[0855] Substituted or unsubstituted heterocyclic groups with 5 to 22 cyclic atoms, or
[0856] The group represented by the above formula (H19a).
[0857] In this embodiment, Rd2, Rd3, Rd5, Rd9, and Rd are preferably... 10 and Rd 12 At least one of them is
[0858] Substituted or unsubstituted aryl groups with 6 to 22 carbon atoms
[0859] Substituted or unsubstituted heterocyclic groups with 5 to 22 cyclic atoms, or
[0860] The group represented by the above formula (H19a).
[0861] In this embodiment, preferably, Rd4 and Rd7 are each independently an aryl group with 6 to 22 cyclic carbon atoms (substituted or unsubstituted), a heterocyclic group with 5 to 22 cyclic atoms (substituted or unsubstituted), or a group represented by the above formula (H19a), and Rd1 to Rd3, Rd5, Rd6, and Rd8 to Rd7. 14 It is a hydrogen atom.
[0862] Preferably, the heterocyclic group with 5 to 22 cyclic atoms in the compound represented by formula (H19) is a group containing one or more oxygen atoms.
[0863] (In any of the compounds represented by formulas (H11) to (H16), (H17) above (e.g., in the first host material and the third host material above), R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently
[0864] hydrogen atom,
[0865] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0866] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0867] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0868] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0869] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[0870] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[0871] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[0872] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
[0873] In R905 In the case of multiple Rs, multiple Rs 905 They are the same or different.
[0874] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.
[0875] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.
[0876] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[0877] In R 802 In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)
[0878] In one embodiment of this invention, Ar in formula (H121), formula (H131), formula (H141), formula (H150), formula (H161), formula (H171), formula (H181), or formula (H191) 12 Ar 13 Ar 14 Ar 151 Ar 16 Ar 17 Are and Ard are each independently a fused polycyclic aromatic hydrocarbon group. In one embodiment of this invention, the fused polycyclic aromatic hydrocarbon group is a group derived from a substituted or unsubstituted pyrene ring or a substituted or unsubstituted benzanthracene ring.
[0879] In one embodiment of this invention, Ar in formula (H121), formula (H131), formula (H141), formula (H150), formula (H161), formula (H171), formula (H181), or formula (H191) 12 Ar 13 Ar 14 Ar 151 Ar 16 Ar 17 Are and Ard are each independently fused polycyclic heterocyclic groups.
[0880] In one embodiment, the fused polycyclic heterocyclic groups in the first and third main materials are each independently selected from one or more groups chosen from the group represented by formula (HX1), formula (HX10), formula (HX11), formula (HX12), formula (HX13), formula (HX14), formula (HX16), and formula (HX2).
[0881] In this embodiment, it is preferred that R in the above formula (H11) is... 101 R 103 R 106 or R 108 Indicates with L 101 The bonding position, R 112 R 115 R 117 or R 120 Indicates with L 101 The bonding position. For example, R in equation (H11) above. 101 and R 112 Indicates with L 101 When the bonding position is such that the compound represented by the above formula (H11) is the compound represented by the following formula (H111), the compound is also preferred. In this embodiment, it is also preferable that at least one of the first host material and the third host material is the compound represented by the following formula (H111).
[0882]
[0883] (In the above formula (H111), R) 102 ~R 111 R 113 ~R 120 L 101 And mx are respectively related to R in the above equation (H11) 102 ~R 111 R 113 ~R 120 L 101 (Same meaning as mx)
[0884] In this embodiment, it is preferred that Xa in the above formula (H12) is an oxygen atom.
[0885] In this embodiment, it is preferred that R in the above formula (H12) is... 124 or R 129 Indicates with L 12 The bonding positions. In the above formula (H12), Xa represents an oxygen atom, R... 124 Indicates with L 12When the bonding positions are such that the compound represented by the above formula (H12) is, for example, represented by the following formula (H122), Xa in the above formula (H12) is an oxygen atom, R... 129 Indicates with L 12 When the bonding position is such that the compound represented by the above formula (H12) is, for example, represented by the following formula (H123).
[0886] In this embodiment, it is also preferred that the compound represented by the above formula (H12) is the compound represented by the following formula (H122) or the compound represented by formula (H123).
[0887]
[0888] (In the above equations (H122) and (H123),
[0889] R 121 ~R 130 Each independently
[0890] hydrogen atom,
[0891] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0892] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0893] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0894] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0895] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0896] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0897] -O-(R 904 The groups shown in the figure,
[0898] -S-(R 905 The groups shown in the figure,
[0899] -N(R 906 (R) 907 The groups shown in the figure,
[0900] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0901] -C(=O)R 801 The groups shown
[0902] -COOR 802 The groups shown
[0903] Halogen atoms,
[0904] Nitro,
[0905] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0906] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0907] Ar 12 L 12 And ma are respectively related to Ar in the above formula (H121) 12 L 12 (Same meaning as "ma")
[0908] In one embodiment of this invention, Ar in formulas (H122) and (H123) above... 12 It is a fused polycyclic aromatic hydrocarbon group.
[0909] In one embodiment of this invention, Ar in formulas (H122) and (H123) above... 12 It is a fused polycyclic heterocyclic group.
[0910] In this embodiment, it is preferred that Ar in the above formula (H13) is... 131 Or Ar 132 Indicates with L 13 The bonding position of Ar in the above formula (H13). 131 Indicates with L 13 When the bonding position is such that the compound represented by the above formula (H13) is, for example, represented by the following formula (H132), Ar... 132 Indicates with L 13 When the bonding position is such that the compound represented by the above formula (H13) is, for example, represented by the following formula (H133).
[0911] In this embodiment, it is also preferred that the compound represented by the above formula (H13) is the compound represented by the following formula (H132) or the compound represented by formula (H133).
[0912]
[0913] (In the above equations (H132) and (H133),
[0914] R 131 ~R 140 Ar 131 and Ar 132 Each independently
[0915] hydrogen atom,
[0916] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0917] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0918] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0919] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0920] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0921] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0922] -O-(R 904 The groups shown in the figure,
[0923] -S-(R 905 The groups shown in the figure,
[0924] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0925] -C(=O)R 801 The groups shown
[0926] -COOR 802 The groups shown
[0927] Halogen atoms,
[0928] cyano,
[0929] Nitro,
[0930] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0931] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0932] L 13 Ar 13 And mb are respectively related to L in the above formula (H131) 13 Ar 13 (Same meaning as mb.)
[0933] In one embodiment of this invention, Ar in formulas (H132) and (H133) above... 131 and Ar 132 It is a fused polycyclic aromatic hydrocarbon group.
[0934] In one embodiment of this invention, Ar in formulas (H132) and (H133) above... 131and Ar 132 It is a fused polycyclic heterocyclic group.
[0935] In one embodiment of this invention, it is preferred that R in the above formula (H14) is... 145 ~R 148 Any two or more adjacent groups in the above formula (H141) are bonded to each other to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring, wherein the groups are bonded to R. 142 Bonded carbon atoms.
[0936] In one embodiment of this invention, the compound represented by formula (H14) is a compound represented by formula (H142), formula (H143) or formula (H144).
[0937]
[0938]
[0939] (In the above formulas (H142), (H143), or (H144),
[0940] R 1A R 1B R 141 R 143 R 144 R 145 R 146 R 147 and R 148 respectively with R in the above formula (H14) 1A R 1B R 141 R 143 R 144 R 145 R 146 R 147 and R 148 Same meaning
[0941] Ar 14 L 14 And mc respectively with Ar in the above formula (H141) 14 L 14 It has the same meaning as mc.
[0942] By R 1401 ~R 1404 In a given set of two or more adjacent groups, at least one group is not bonded to the others.
[0943] R 1401 ~R 1404 Each independently
[0944] hydrogen atom,
[0945] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0946] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0947] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0948] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0949] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0950] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0951] -O-(R 904 The groups shown in the figure,
[0952] -S-(R 905 The groups shown in the figure,
[0953] -N(R 906 (R) 907 The groups shown in the figure,
[0954] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0955] -C(=O)R 801 The groups shown
[0956] -COOR 802 The groups shown
[0957] Halogen atoms,
[0958] cyano,
[0959] Nitro,
[0960] Substituted or unsubstituted aryl groups with 6 to 17 carbon atoms, or
[0961] (Substituted or unsubstituted heterocyclic groups with 5 to 17 cyclic atoms)
[0962] In this embodiment, it is also preferred that Ar in the above formulas (H141), (H142), (H143) or (H144) is... 14 A group derived from a substituted or unsubstituted pyrene ring, a substituted or unsubstituted fluoranthene ring, a substituted or unsubstituted benzo[a]fluoranthene ring, a substituted or unsubstituted benzo[a]anthene ring, or a substituted or unsubstituted benzo[a]xanthine ring.
[0963] In this embodiment, it is also preferred that at least one of the first main material and the third main material is any one of the compounds selected from the group consisting of the compound shown in formula (H111), the compound shown in formula (H122), the compound shown in formula (H123), the compound shown in formula (H132), the compound shown in formula (H133), the compound shown in formula (H142), the compound shown in formula (H143), and the compound shown in formula (H144).
[0964] In this embodiment, preferably, the numbers selected in the above formula (H17) are Rb1, Rb3, Rb5, Rb7, Rb9, and Rb 11 、Rb 13 and Rb 14 One or more of the groups are groups represented by the above formula (H171).
[0965] In this embodiment, more preferably, the selections in the above formula (H17) are Rb1, Rb5, Rb9, and Rb 13 and Rb 14 One or more of the groups are groups represented by the above formula (H171).
[0966] In this embodiment, more preferably, Rb in the above formula (H17) is... 14 The group is represented by the formula (H171) above.
[0967] In this embodiment, it is preferred that the compound represented by the above formula (H17) is represented by the following formula (H172).
[0968]
[0969] (In the above formula (H172), Rb1~Rb 13 L 17 Ar 17 and mg are respectively related to Rb1~Rb in the above formula (H17) or (H171). 13 L 17 Ar 17 (Same meaning as mg.)
[0970] In one embodiment, at least one of the first and third main materials is a compound having at least one group represented by the following formula (HX1) in the molecule.
[0971]
[0972] (In the above formula (HX1),
[0973] Z1 is an oxygen atom or a sulfur atom.
[0974] R X1 ~R X8 and R X11 ~R X14 Each independently
[0975] hydrogen atom,
[0976] Halogen atoms,
[0977] cyano,
[0978] Nitro,
[0979] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0980] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0981] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0982] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0983] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0984] -O-(R 904 The groups shown in the figure,
[0985] -S-(R 905 The groups shown in the figure,
[0986] -N(R 906 (R) 907 The groups shown in the figure,
[0987] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0988] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0989] R 901 ~R 907 Each independently
[0990] hydrogen atom,
[0991] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0992] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0993] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0994] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0995] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[0996] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[0997] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[0998] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
[0999] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.
[1000] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.
[1001] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.
[1002] nx is 0, 1, or 2.
[1003] in,
[1004] When nx is 0, it is selected from R X1 ~R X8 One of them is a single bond that bonds with *ex.
[1005] When nx is 1, one condition is satisfied, which can be selected from the group consisting of (a1) to (a6) below.
[1006] When nx is 2, two conditions are satisfied from the group consisting of (a1) to (a6) below. (a1) and (a2) are not satisfied simultaneously, (a2) and (a3) are not satisfied simultaneously, (a4) and (a5) are not satisfied simultaneously, and (a5) and (a6) are not satisfied simultaneously.
[1007] Selected from R X11 ~R X14 And R, which is not a single bond bonded to *cx and *dx. X1 ~R X8 One of them is a single bond that bonds with *ex.
[1008] *fx represents the bonding position with an atom in the first or third host material.
[1009] (a1)R X1 With R X2 One of them is a single bond that bonds with *cx, R X1 With R X2 The other side is a single bond that bonds with *dx.
[1010] (a2)R X2 With R X3 One of them is a single bond that bonds with *cx, R X2 With R X3 The other side is a single bond that bonds with *dx.
[1011] (a3)R X3 With R X4 One of them is a single bond that bonds with *cx, R X3 With R X4 The other side is a single bond that bonds with *dx.
[1012] (a4)R X5 With R X6 One of them is a single bond that bonds with *cx, R X5 With R X6 The other side is a single bond that bonds with *dx.
[1013] (a5)R X6 With R X7 One of them is a single bond that bonds with *cx, R X6 With R X7 The other side is a single bond that bonds with *dx.
[1014] (a6)R X7 With R X8 One of them is a single bond that bonds with *cx, R X7 With R X8 The other side is a single bond that bonds with *dx.
[1015] In one embodiment of this invention, when nx in the above formula (HX1) is 0, the group represented by the above formula (HX1) is represented by the following formula (HX10).
[1016] In one embodiment, at least one of the first and third main materials is a compound having at least one group represented by the following formula (HX10) in the molecule.
[1017]
[1018] (In the above formula (HX10), R)X1 ~R X8 Z1 and R in the above formula (HX1) are respectively X1 ~R X8 Same meaning as Z1
[1019] Among them, selected from R X1 ~R X8 One of them is a single bond that bonds with *ex.
[1020] *fx represents the bonding position with an atom in the first or third host material.
[1021] In one embodiment, at least one of the first and third main materials is a compound having at least one group of the above formula (HX1) in the molecule and nx is 1.
[1022] In one embodiment, at least one of the first and third main materials is a compound having at least one group selected from the group represented by formula (HX11), formula (HX12), and formula (HX13) in its molecule.
[1023] The group represented by formula (HX11) is equivalent to the group that satisfies condition (a3) above, the group represented by formula (HX12) is equivalent to the group that satisfies condition (a2) above, and the group represented by formula (HX13) is equivalent to the group that satisfies condition (a1) above.
[1024]
[1025]
[1026]
[1027] (In the above equations (HX11), (HX12), and (HX13), R) X1 ~R X8 R X11 ~R X14 Z1 and R in the above formula (HX1) are respectively X1 ~R X8 R X11 ~R X14 Same meaning as Z1
[1028] In the above equations (HX11), (HX12), and (HX13), R... X1 ~R X8 and R X11 ~R X14 One of them is a single bond that bonds with *ex.
[1029] *fx represents the bonding position with an atom in the first or third host material.
[1030] In one embodiment, at least one of the first and third main materials is a compound having a group in its molecule represented by the following formula (HX14).
[1031] The group represented by the following formula (HX14) is equivalent to a group that satisfies the above conditions (a1) and (a6).
[1032]
[1033] (In the above formula (HX14), R) X3 ~R X6 Z1 and R in the above formula (HX1) are respectively X3 ~R X6 Same meaning as Z1
[1034] R X11 ~R X18 Each independently relates to R in the above equation (HX1). X11 ~R X14 The meaning is the same, R in the above formula (HX14) X3 ~R X6 and R X11 ~R X18 One of them is a single bond bonded to *ex, and *fx represents the bonding position with an atom in the first or third host material.
[1035] In one embodiment of this invention, R in formula (HX14) X4 or R X5 This is a single bond that bonds with *ex.
[1036] In one embodiment, the fused polycyclic heterocyclic groups in the first and third host materials are groups represented by the above formula (HX14).
[1037] In one embodiment of this invention, the compound represented by formula (H13) is selected from Ar. 131 Ar 132 and Ar 13 At least one of the groups is any one of the groups selected from the group consisting of the group shown in formula (HX11), the group shown in formula (HX12), and the group shown in formula (HX13).
[1038] In one embodiment of this invention, the compound represented by formula (H132) is selected from Ar. 132 and Ar 13At least one of the groups is selected from any one of the groups formed by the group shown in formula (HX11), the group shown in formula (HX12), and the group shown in formula (HX13).
[1039] In one embodiment of this invention, the compound represented by formula (H133) is selected from Ar. 131 and Ar 13 At least one of the groups is selected from any one of the groups formed by the group shown in formula (HX11), the group shown in formula (HX12), and the group shown in formula (HX13).
[1040] In this embodiment, it is also preferred that the compound represented by the above formula (H13) is a compound represented by the following formula (H134) or formula (H135).
[1041]
[1042]
[1043] (In the above equations (H134) and (H135),
[1044] R 131 ~R 140 and Ar 132 Respectively with R in the above formula (H13) 131 ~R 140 and Ar 132 Same meaning
[1045] L 13 And mb are respectively related to L in the above formula (H131) 13 It has the same meaning as mb.
[1046] R X1 R X2 R X4 R X5 ~R X7 R X11 ~R X14 Z1 and R in the above formula (HX1) are respectively X1 R X2 R X4 R X5 ~R X7 R X11 ~R X14 (Same meaning as Z1.)
[1047] In one embodiment, the fused polycyclic heterocyclic group in the first and third main materials is a group selected from any one of the groups represented by formula (HX1), formula (HX10), formula (HX11), formula (HX12), formula (HX13), and formula (HX2).
[1048] In one embodiment, by having at least one group selected from the group represented by formula (HX1), formula (HX10), formula (HX11), formula (HX12), and formula (HX13) in the host material molecule, hole injection capability is improved for the host material (more specifically, for the aryl group in the host material molecule). Hole injection capability is more easily improved when the host material has a benzo[a]anthracene structure as shown in the compound represented by formula (H13).
[1049] In one embodiment, at least one of the first and third main materials is a compound having at least one group represented by the following formula (HX2) in the molecule.
[1050]
[1051] (In the above formula (HX2),
[1052] Selected from R 171 ~R 180 One of them is a single bond that bonds with *gx.
[1053] R 171 ~R 180 Each independently
[1054] hydrogen atom,
[1055] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1056] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1057] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1058] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1059] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1060] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1061] -O-(R 904 The groups shown in the figure,
[1062] -S-(R 905 The groups shown in the figure,
[1063] -N(R 906 (R) 907 The groups shown in the figure,
[1064] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1065] -C(=O)R 801 The groups shown
[1066] -COOR 802 The groups shown
[1067] Halogen atoms,
[1068] Nitro,
[1069] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1070] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1071] *hx indicates the bonding position with an atom in the first or third host material.
[1072] R 901 ~R 907 R 801 and R 802 Each independently
[1073] hydrogen atom,
[1074] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1075] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1076] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1077] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1078] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[1079] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[1080] In R 903In the case of multiple Rs, multiple Rs 903 They are the same or different.
[1081] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
[1082] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.
[1083] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.
[1084] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.
[1085] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[1086] In R 802 In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)
[1087] In the above formula (HX2), R 171 ~R 180 Two or more adjacent groups are not bonded to each other.
[1088] In one embodiment of this invention, the fused polycyclic heterocyclic groups in the first and third host materials are groups represented by the above formula (HX12).
[1089] In one embodiment of this invention, the fused polycyclic heterocyclic groups in the first and third host materials are groups represented by the formula (HX2) above.
[1090] In this embodiment, it is preferred that Ar in the above formulas (H12), (H122), and (H123) is... 12 The group is represented by the formula (HX2) above.
[1091] In this embodiment, it is preferred that R in the above formula (HX2) is... 174 or R 179 This is a single bond that bonds with *gx.
[1092] In this embodiment, it is also preferred that the compound represented by the above formula (H12) is the compound represented by the following formula (H124).
[1093]
[1094] (In the above formula (H124), R) 121 ~R 123 R 125 ~R 130 L 12 And ma are respectively related to R in the above formula (H12) or (H121) 121 ~R 123 R 125 ~R 130 L 12 R has the same meaning as ma. 171 ~R 173 and R 175 ~R 180 respectively with R in the above formula (HX2) 171 ~R 173 and R 175 ~R 180 The meaning is the same.
[1095] In one embodiment, at least one of the first and third main materials is a compound having at least one group represented by the following formula (HX16) in the molecule.
[1096]
[1097] (In the above formula (HX16),
[1098] Za represents either an oxygen atom or a sulfur atom.
[1099] Ra1 to Ra8 are each independent of each other.
[1100] hydrogen atom,
[1101] Halogen atoms,
[1102] cyano,
[1103] Nitro,
[1104] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1105] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1106] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1107] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1108] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1109] -O-(R 904 The groups shown in the figure,
[1110] -S-(R 905 The groups shown in the figure,
[1111] -N(R 906 (R) 907 The groups shown in the figure,
[1112] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1113] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1114] One single bond selected from Ra1 to Ra8 is bonded to *kx.
[1115] *mx represents the bonding position with an atom in the first or third host material.
[1116] In one embodiment of this invention, Ra4 or Ra5 in formula (HX16) is a single bond bonded to *kx.
[1117] In one embodiment of this invention, the fused polycyclic heterocyclic groups in the first and third host materials are groups represented by the formula (HX16) above.
[1118] In one embodiment of this invention, the group represented by the above formula (H150) is the group represented by the following formula (H151).
[1119]
[1120] (In the above formula (H151),
[1121] X 15 For C(R) 1511 (R) 1512 ), oxygen atom or sulfur atom,
[1122] L 15 for
[1123] single bond,
[1124] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1125] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1126] md is 0, 1, 2, 3, 4 or 5.
[1127] In L 15 When there are more than two, more than two L15 They are the same or different.
[1128] By R 1500 ~R 1504 One or more groups consisting of two or more adjacent elements.
[1129] They bond together to form substituted or unsubstituted monocyclic rings.
[1130] They bond together to form substituted or unsubstituted fused rings, or
[1131] They do not bond with each other.
[1132] By R 1511 and R 1512 Groups
[1133] They bond together to form substituted or unsubstituted monocyclic rings.
[1134] They bond together to form substituted or unsubstituted fused rings, or
[1135] They do not bond with each other.
[1136] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 1500 ~R 1504 Each independently
[1137] hydrogen atom,
[1138] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1139] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1140] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1141] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1142] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1143] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1144] -O-(R 904 The groups shown in the figure,
[1145] -S-(R 905 The groups shown in the figure,
[1146] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1147] -C(=O)R801 The groups shown
[1148] -COOR 802 The groups shown
[1149] Halogen atoms,
[1150] cyano,
[1151] Nitro,
[1152] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1153] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1154] Multiple R 1500 They are the same or different.
[1155] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 1511 and R 1512 Each of the following groups is independently composed of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.
[1156] In equation (H151) above, * indicates the bonding position with the pyrene ring in equation (H15) above.
[1157] In this embodiment, it is also preferred that the compound represented by the above formula (H15) is a monopyrene compound having only one pyrene ring in the molecule.
[1158] In this embodiment, it is preferred that R in the above formula (H15) is... 151 R 153 R 156 or R 158 The group is represented by the formula (H150) above.
[1159] In this embodiment, it is preferred that R in the above formula (H15) is... 151 R 153 R 156 or R 158 The group is represented by the formula (H151) above.
[1160] In this embodiment, it is preferred that Ar in the above formula (H150) is... 151 It is a group represented by formula (HX2) or a group represented by formula (HX14).
[1161] In the organic EL element according to this embodiment, it is also preferred that one of the first host material and the third host material is a compound represented by formula (H11) above, and the other of the first host material and the third host material is a compound represented by formula (H13). More preferably, the first host material is a compound represented by formula (H11) above, and the third host material is a compound represented by formula (H13) above. Further preferably, the first host material is a compound represented by formula (H111) above, and the third host material is a compound represented by formula (H132) or formula (H133) above. Even more preferably, the first host material is a compound represented by formula (H111) above, and the third host material is a compound represented by formula (H134) or formula (H135) above. By incorporating the first host material and the aforementioned third host material in such a combination of compounds into the first light-emitting unit and the second light-emitting unit, the element performance can be easily improved.
[1162] In the organic EL element according to this embodiment, it is also preferred that one of the first host material and the third host material is a compound represented by formula (H14) or formula (H15) above, and the other of the first host material and the third host material is a compound represented by formula (H13). More preferably, the first host material is a compound represented by formula (H14) or formula (H15) above, and the third host material is a compound represented by formula (H13). Further preferably, the first host material is a compound represented by formula (H142), formula (H143), or formula (H144) above, and the third host material is a compound represented by formula (H132) or formula (H133) above. Further preferably, the first host material is a compound represented by formula (H142), formula (H143), or formula (H144) above, and the third host material is a compound represented by formula (H134) or formula (H135) above. By incorporating the first and second light-emitting units in a compound of the first and third main materials, the performance of the components can be easily improved.
[1163] In the organic EL element according to this embodiment, it is also preferred that one of the first host material and the third host material is a compound represented by formula (H15) above, and the other of the first host material and the third host material is a compound represented by formula (H13). More preferably, the first host material is a compound represented by formula (H13) above, and the third host material is a compound represented by formula (H15) above. Even more preferably, the first host material is a compound represented by formula (H132) or formula (H133) above, the third host material is a compound represented by formula (H15) above, and Ar in formula (H150) above. 151The group is represented by formula (HX2) or formula (HX14). More preferably, the first host material is a compound represented by formula (H134) or formula (H135), the third host material is a compound represented by formula (H15), and Ar in formula (H150) is... 151 The group is represented by formula (HX2) or formula (HX14). By incorporating the first and second light-emitting units in a combination of the first and third host materials, the performance of the element can be easily improved.
[1164] In the organic EL element according to this embodiment, it is also preferred that one of the first host material and the third host material is a compound represented by formula (H12) above, and the other of the first host material and the third host material is a compound represented by formula (H13). More preferably, the first host material is a compound represented by formula (H12) above, and the third host material is a compound represented by formula (H13). Further preferably, the first host material is a compound represented by formula (H122) or formula (H123) above, and the third host material is a compound represented by formula (H132) or formula (H133) above. Further preferably, the first host material is a compound represented by formula (H124) above, and the third host material is a compound represented by formula (H134) or formula (H135) above. By incorporating the first host material and the aforementioned third host material in such a combination of compounds into the first light-emitting unit and the second light-emitting unit, the element performance can be easily improved.
[1165] In the organic EL element according to this embodiment, it is also preferred that the first host material and the third host material are compounds represented by formula (H13) above. More preferably, one of the first host material and the third host material is a compound represented by formula (H132) or formula (H133) above, and the other of the first host material and the third host material is a compound represented by formula (H134) or formula (H135) above. By incorporating the first host material and the aforementioned third host material in such a combination of compounds into the first light-emitting unit and the second light-emitting unit, the element performance can be easily improved.
[1166] In the organic EL element according to this embodiment, it is also preferred that the first host material and the third host material are compounds represented by the above formula (H15). By including the first host material and the above-mentioned third host material in such a combination of compounds in the first light-emitting unit and the second light-emitting unit, the performance of the element can be easily improved.
[1167] In the organic EL element according to this embodiment, it is also preferable that one of the first host material and the third host material is a compound represented by formula (H13) above, and the other of the first host material and the third host material is a compound represented by formula (H17). By including the first host material and the third host material in such a combination of compounds in the first light-emitting unit and the second light-emitting unit, the element performance can be easily improved.
[1168] In the organic EL element involved in this embodiment, it is preferred that one or both of the first host material and the third host material are compounds containing one or more deuterium atoms in their molecules.
[1169] In the organic EL element involved in this embodiment, it is also preferred that one or both of the first host material and the third host material are compounds that do not contain deuterium atoms in their molecules.
[1170] In this embodiment, it is also preferred that one or both of the first and third main materials contain only carbon atoms and hydrogen atoms in their molecules.
[1171] In this embodiment, it is also preferred that one or both of the first and third main materials contain carbon atoms, hydrogen atoms, and heteroatoms in their molecules. When one or both of the first and third main materials contain heteroatoms, it is preferred that the heteroatom is one or more selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, silicon atoms, phosphorus atoms, and boron atoms.
[1172] In this embodiment, it is also preferred that the first main material is a compound containing only carbon atoms and hydrogen atoms in the molecule, and the third main material is a compound containing carbon atoms, hydrogen atoms and heteroatoms in the molecule.
[1173] In this embodiment, it is also preferred that both the first and third main materials contain carbon atoms, hydrogen atoms, and heteroatoms in their molecules.
[1174] In this embodiment, it is preferred that L 101 L 12 L 13 L 14 L 15 L 151 L 16 L 17 Ld and Le are each independently a single bond or a group represented by the following formulas (L1), (L2), (L3), (L4), (L5), (L6), (L7), (L8), (L9), or (L10).
[1175]
[1176] In formulas (L1) to (L10) above, * indicates a bonding position. Each of the groups shown in formulas (L1) to (L10) above may independently have one or more of the above-mentioned "optional substituents", or may not have any (i.e., unsubstituted). Each of the groups shown in formulas (L1) to (L10) above may independently have one or more deuterium atoms.
[1177] In the first and third main materials, it is preferred that the substituents described as "substituted or unsubstituted" are each independently a halogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 cyclic carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 cyclic atoms.
[1178] In the first and third main materials, it is preferred that the substituents described as "substituted or unsubstituted" are each independently an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted aryl group having 6 to 13 cyclic carbon atoms, or an unsubstituted heterocyclic group having 5 to 13 cyclic atoms.
[1179] In the first and third main materials, it is preferred that the substituents described as "substituted or unsubstituted" are each independently an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted aryl group having 6 to 12 cyclic carbon atoms, or an unsubstituted heterocyclic group having 5 to 10 cyclic atoms.
[1180] In one embodiment of the organic EL display device, the groups described as "substituted or unsubstituted" in the first and third main materials are all "unsubstituted" groups.
[1181] (Manufacturing methods for the first and third main materials)
[1182] The first and third main materials can be manufactured using known methods. Alternatively, the first and third main materials can also be manufactured using known alternative reactions and raw materials corresponding to the target substance, following the same known methods.
[1183] (Specific examples of the first and third main materials)
[1184] Specific examples of the first and third main materials include the following compounds. However, the present invention is not limited to these specific examples of the first and third main materials.
[1185]
[1186]
[1187]
[1188]
[1189]
[1190]
[1191]
[1192]
[1193]
[1194]
[1195]
[1196]
[1197]
[1198]
[1199]
[1200]
[1201]
[1202]
[1203]
[1204]
[1205]
[1206]
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[1208]
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[1233]
[1234]
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[1366]
[1367] (Second and Fourth Main Materials)
[1368] In one embodiment of the organic EL element, the second and fourth main materials are identical. Alternatively, in another embodiment of the organic EL element, the second and fourth main materials are different.
[1369] In this embodiment, the second and fourth main materials are not particularly limited. Preferably, at least one of the second and fourth main materials is an anthracene derivative.
[1370] In this embodiment, more preferably, the second main material and the fourth main material are each independently a compound represented by the following formula (2).
[1371]
[1372] (In the above formula (2),
[1373] R 201 ~R 208 Each independently
[1374] hydrogen atom,
[1375] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1376] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1377] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1378] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1379] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1380] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1381] -O-(R 904 The groups shown in the figure,
[1382] -S-(R 905 The groups shown in the figure,
[1383] -N(R 906 (R) 907 The groups shown in the figure,
[1384] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1385] -C(=O)R 801 The groups shown
[1386] -COOR 802 The groups shown
[1387] Halogen atoms,
[1388] cyano,
[1389] Nitro,
[1390] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1391] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1392] L 201 and L 202 Each independently
[1393] single bond,
[1394] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1395] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1396] Ar 201 and Ar 202 Each independently
[1397] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1398] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1399] (In the compounds shown in formula (2) above (e.g., in the second and fourth main materials mentioned above), R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently
[1400] hydrogen atom,
[1401] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1402] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1403] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1404] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1405] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[1406] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[1407] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[1408] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
[1409] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.
[1410] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.
[1411] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.
[1412] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[1413] In R 802 In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)
[1414] In the above formula (2), R 201 ~R 208 Two or more adjacent groups are not bonded to each other.
[1415] It should be noted that in this embodiment, the second main material and the fourth main material can both be compounds shown in the above formula (2), and they are different compounds from each other.
[1416] In this embodiment, it is preferred that Ar 202 It is a substituted or unsubstituted cyclic aryl group with 6 to 50 carbon atoms and containing at least one deuterium atom.
[1417] In this embodiment, it is preferred that L 202 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted, and contains at least one deuterium atom.
[1418] In this embodiment, it is preferred that -L 202 -Ar 202 The group shown contains at least one deuterium atom.
[1419] In this embodiment, it is preferred that the compound represented by the above formula (2) is a compound represented by the following formulas (H21), (H22), (H23), (H24), (H25), (H26), (H27), (H28) or (H29).
[1420]
[1421]
[1422]
[1423]
[1424]
[1425] (In the above formulas (H21) to (H29), L) 201 and Ar 201 respectively with L in the above formula (H2) 201 and Ar 201 The meaning is the same, R 201 ~R 208 respectively with R in the above formula (H2) 201 ~R 208 The meaning is the same.
[1426] In this embodiment, it is preferred that the second main material and the fourth main material are each independently selected from the group consisting of the compound shown in formula (H21), the compound shown in formula (H22), the compound shown in formula (H23), the compound shown in formula (H24), the compound shown in formula (H25), the compound shown in formula (H26), the compound shown in formula (H27), the compound shown in formula (H28), and the compound shown in formula (H29).
[1427] In one embodiment of the organic EL element, at least one of the second and fourth host materials is a compound having at least one group represented by the following formula (HY1) in its molecule.
[1428]
[1429] (In the above formula (HY1),
[1430] R Y1~R Y8 and R Y11 ~R Y14 Each independently
[1431] hydrogen atom,
[1432] Halogen atoms,
[1433] cyano,
[1434] Nitro,
[1435] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1436] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1437] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1438] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1439] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1440] -O-(R 904 The groups shown in the figure,
[1441] -S-(R 905 The groups shown in the figure,
[1442] -N(R 906 (R) 907 The groups shown in the figure,
[1443] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1444] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1445] ny is 0 or 1,
[1446] in,
[1447] When ny is 0, it is selected from R Y1 ~R Y8 One of them is a single bond that bonds with *ey.
[1448] When ny is 1, one condition from the group consisting of (b1) to (b3) below is satisfied, and the result is selected from R. Y5 ~R Y8 R Y11 ~R Y14 And R that is not a single bond bonded to *cy and *dy Y1 ~R Y4One of them is a single bond that bonds with *ey.
[1449] Z2 is an oxygen atom or a sulfur atom.
[1450] *fy indicates the bonding position with an atom in the second or fourth host material.
[1451] (b1)R Y1 and R Y2 One of them is a single bond that bonds with *cy, R Y1 and R Y2 The other side is a single bond that bonds with *dy.
[1452] (b2)R Y2 and R Y3 One of them is a single bond that bonds with *cy, R Y2 and R Y3 The other side is a single bond that bonds with *dy.
[1453] (b3)R Y3 and R Y4 One of them is a single bond that bonds with *cy, R Y3 and R Y4 The other side is a single bond that bonds with *dy.
[1454] In one embodiment of the organic EL element, when ny in the above formula (HY1) is 0, the group represented by the above formula (HY1) is represented by the following formula (HY10).
[1455] In one embodiment of the organic EL element, at least one of the second and fourth host materials is a compound having at least one group represented by the following formula (HY10) in the molecule.
[1456]
[1457] (In the above formula (HY10), R) Y1 ~R Y8 Z2 and R in the above equation (HY1) Y1 ~R Y8 The same meaning as Z2.
[1458] Among them, selected from R Y1 ~R Y8 One of them is a single bond that bonds with *ey.
[1459] *fy indicates the bonding position with an atom in the second host material.
[1460] In one embodiment of the organic EL element, at least one of the second and fourth host materials is a compound having at least one group of the above formula (HY1) in the molecule and ny is 1.
[1461] In one embodiment of the organic EL element, at least one of the second and fourth host materials is a compound having at least one group selected from the group consisting of groups represented by formulas (HY11), (HY12), and (HY13). The group represented by formula (HY11) corresponds to the group satisfying condition (b3) above, the group represented by formula (HY12) corresponds to the group satisfying condition (b2) above, and the group represented by formula (HY13) corresponds to the group satisfying condition (b1) above.
[1462]
[1463]
[1464]
[1465] (In the above equations (HY11), (HY12) and (HY13), R) Y1 ~R Y8 R Y11 ~R Y14 Z2 and R in the above formula (HY1) are respectively Y1 ~R Y8 R Y11 ~R Y14 The same meaning as Z2.
[1466] Among them, R Y1 ~R Y8 and R Y11 ~R Y14 One of them is a single bond that bonds with *ey.
[1467] *fy indicates the bonding position with an atom in the second or fourth host material.
[1468] In one embodiment of the organic EL element, at least one of the second and fourth host materials is a compound represented by formula (2) above, and the molecule of the compound represented by formula (2) has at least one group represented by formula (HY1) above.
[1469] In one embodiment of the organic EL element, Ar in the above formula (2) 201 and Ar 202 At least one of them is a group represented by the above formula (HY1).
[1470] In one embodiment of the organic EL element, Ar in formulas (H21) to (H29) above... 201 The group is represented by the formula (HY1) above.
[1471] In one embodiment of the organic EL element, Ar in the above formula (2) 201 Or Ar 202 The group is represented by the formula (HY1) above.
[1472] In one embodiment of the organic EL element, at least one of the second and fourth host materials is a compound represented by formula (2) above, and the molecule of the compound represented by formula (2) has at least one group selected from the group represented by formula (HY11), formula (HY12) and formula (HY13) above.
[1473] In one embodiment of the organic EL element, Ar in the above formula (2) 201 and Ar 202 At least one of them is any group selected from the group consisting of the groups shown in the above formulas (HY11), (HY12) and (HY13).
[1474] In one embodiment of the organic EL element, Ar in the above formula (2) 201 Or Ar 202 It is any one of the groups selected from the group consisting of the groups shown in the above formulas (HY11), (HY12) and (HY13).
[1475] In one embodiment of the organic EL element, Ar in formulas (H21) to (H29) above... 201 The group is the one shown in formula (HY11), formula (HY12) or formula (HY13) above.
[1476] In one embodiment of the organic EL element, the excitation resistance of the host material is improved by having at least one group selected from the group group shown in formulas (HY1), (HY10), (HY11), (HY12), and (HY13) in the molecule. By using such a host material in the second light-emitting layer, the organic EL element can be easily extended in lifetime.
[1477] In one embodiment of the organic EL element, Ar in the above formula (2) 201 and Ar 202 Each is an aryl group, either substituted or unsubstituted, with 6 to 18 carbon atoms in a cyclic structure.
[1478] In one embodiment of the organic EL element, Ar in formulas (H21) to (H29) above... 201 It is an aryl group with 6 to 18 carbon atoms, either substituted or unsubstituted.
[1479] In one embodiment of the organic EL element, R in the above formula (2) 201 ~R 208 At least one of them is a deuterium atom.
[1480] In one embodiment of the organic EL element, R in the above formula (2) 201 ~R 208 At least one of them is a deuterium atom.
[1481] In one embodiment of the organic EL element, R in the above formula (2) 201 ~R 208 All are deuterium atoms.
[1482] In one embodiment of the organic EL element, R in the above formula (2) 201 ~R 208 All are protium atoms.
[1483] In one embodiment of the organic EL element, Ar in the above formula (2) 201 Ar 202 L 201 and L 202 It has at least one deuterium atom among its hydrogen atoms.
[1484] In one embodiment of the organic EL element, Ar in the above formula (2) 201 Ar 202 L 201 and L 202 All the hydrogen atoms it contains are deuterium atoms.
[1485] In one embodiment of the organic EL element, Ar in the above formula (2) 201 Ar 202 L 201 and L 202 All of its hydrogen atoms are protium atoms.
[1486] In one embodiment of the organic EL element, R in formulas (HY1), (HY10), (HY11), (HY12), and (HY13) Y1 ~R Y8 R Y11 ~R Y14At least one of them is a deuterium atom.
[1487] In this embodiment, it is also preferred that one or both of the second and fourth main materials are compounds containing one or more deuterium atoms in their molecules.
[1488] In this embodiment, it is also preferred that one or both of the second and fourth main materials are compounds that do not contain deuterium atoms in their molecules.
[1489] In this embodiment, it is also preferred that one or both of the second and fourth main materials contain only carbon atoms and hydrogen atoms in their molecules.
[1490] In this embodiment, it is also preferred that one or both of the second and fourth main materials contain carbon atoms, hydrogen atoms, and heteroatoms in their molecules. When one or both of the second and fourth main materials contain heteroatoms, it is preferred that the heteroatom is one or more selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, silicon atoms, phosphorus atoms, and boron atoms.
[1491] In this embodiment, it is also preferred that one or both of the second light-emitting layer and the fourth light-emitting layer further include a common host material, wherein the common host material contained in the second light-emitting layer is the same as or different from the common host material contained in the fourth light-emitting layer, the second host material is different from the common host material contained in the second light-emitting layer and the common host material contained in the fourth light-emitting layer, and the fourth host material is different from the common host material contained in the second light-emitting layer and the common host material contained in the fourth light-emitting layer.
[1492] In one embodiment of the organic EL element, the co-host material is an anthracene derivative.
[1493] In one embodiment of the organic EL element, the common host material is a compound represented by any one of the formulas (2) and (H21) to (H29) above.
[1494] In this embodiment, the co-host material contained in the second light-emitting layer is sometimes referred to as the first co-host material. In one embodiment, the triplet energy T1(H2) of the second host material and the triplet energy T1(cH1) of the first co-host material satisfy the following mathematical formula (Formula 5A), (Formula 5B), or (Formula 5C).
[1495] T1(H2)>T1(cH1) …(Mathematical expression 5A)
[1496] T1(H2) = T1(cH1) …(Mathematical expression 5B)
[1497] T1(H2)<T1(cH1) …(Mathematical expression 5C)
[1498] In this embodiment, the co-host material contained in the fourth luminescent layer is sometimes referred to as the second co-host material. In one embodiment, the triplet energy T1(H4) of the fourth host material and the triplet energy T1(cH2) of the second co-host material satisfy the following mathematical formula (Formula 6A), (Formula 6B), or (Formula 6C).
[1499] T1(H4)>T1(cH2) …(Mathematical expression 6A)
[1500] T1(H4) = T1(cH2) …(Mathematical expression 6B)
[1501] T1(H4) < T1(cH2) …(Mathematical expression 6C)
[1502] In the second and fourth main materials, it is preferred that the substituents described as "substituted or unsubstituted" are each independently a halogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 cyclic carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 cyclic atoms.
[1503] In the second and fourth main materials, it is preferred that the substituents described as "substituted or unsubstituted" are each independently an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted aryl group having 6 to 13 cyclic carbon atoms, or an unsubstituted heterocyclic group having 5 to 13 cyclic atoms.
[1504] In the second and fourth main materials, it is preferred that the substituents described as "substituted or unsubstituted" are each independently an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted aryl group having 6 to 12 cyclic carbon atoms, or an unsubstituted heterocyclic group having 5 to 10 cyclic atoms.
[1505] In one embodiment of the organic EL element, the groups described as "substituted or unsubstituted" in the second and fourth body materials are all "unsubstituted" groups.
[1506] (Manufacturing methods for the second and fourth main body materials)
[1507] The second and fourth main materials involved in this embodiment can be manufactured by known methods, or can be manufactured by using known alternative reactions and raw materials corresponding to the target substance, similar to these methods.
[1508] (Specific examples of the second and fourth main materials)
[1509] Specific examples of the second and fourth main materials involved in this embodiment include the following compounds. However, the present invention is not limited to these specific examples.
[1510]
[1511]
[1512]
[1513]
[1514]
[1515]
[1516]
[1517]
[1518]
[1519]
[1520]
[1521]
[1522]
[1523]
[1524]
[1525]
[1526]
[1527]
[1528]
[1529]
[1530]
[1531]
[1532]
[1533]
[1534]
[1535]
[1536]
[1537]
[1538]
[1539]
[1540]
[1541]
[1542]
[1543]
[1544]
[1545]
[1546]
[1547]
[1548]
[1549]
[1550]
[1551]
[1552]
[1553]
[1554]
[1555] (Luminescent compounds)
[1556] Preferably, each luminescent layer within the luminescent region independently contains a luminescent compound. The luminescent compound contained in each luminescent layer is independently either fluorescent or phosphorescent. In this embodiment, it is preferred that at least one luminescent layer contains a fluorescent compound. In this embodiment, when the luminescent layer contains a host material and a luminescent compound, the upper limit of the combined content of the host material and the luminescent compound in the luminescent layer is 100% by mass.
[1557] In this embodiment, the first, second, third and fourth light-emitting layers each independently contain a host material and a luminescent compound that exhibits light emission with a maximum peak wavelength of less than 500 nm.
[1558] In the organic EL element of this embodiment, it is preferred that at least one of the above-mentioned luminescent compounds contained in the first luminescent layer, the second luminescent layer, the third luminescent layer and the fourth luminescent layer is a luminescent compound that exhibits a maximum peak wavelength of 430 nm or more and 480 nm or less.
[1559] In the organic EL element of this embodiment, it is preferred that at least one of the above-mentioned luminescent compounds contained in the first luminescent layer, the second luminescent layer, the third luminescent layer and the fourth luminescent layer is a fluorescent luminescent compound.
[1560] In the organic EL element of this embodiment, it is also preferred that the light-emitting compounds contained in the first light-emitting layer, the second light-emitting layer, the third light-emitting layer and the fourth light-emitting layer are all fluorescent light-emitting compounds.
[1561] In the organic EL element involved in this embodiment, it is preferred that at least one of the light-emitting layers selected from the group consisting of the first light-emitting layer, the second light-emitting layer, the third light-emitting layer and the fourth light-emitting layer does not contain phosphorescent materials.
[1562] In the organic EL element involved in this embodiment, it is preferable that the first light-emitting layer, the second light-emitting layer, the third light-emitting layer and the fourth light-emitting layer do not contain phosphorescent materials.
[1563] In this specification, the luminescent compound contained in the first luminescent layer is sometimes referred to as the first luminescent compound, the luminescent compound contained in the second luminescent layer is sometimes referred to as the second luminescent compound, the luminescent compound contained in the third luminescent layer is sometimes referred to as the third luminescent compound, and the luminescent compound contained in the fourth luminescent layer is sometimes referred to as the fourth luminescent compound.
[1564] In this specification, "the first luminescent compound, the second luminescent compound, the third luminescent compound and the fourth luminescent compound" are sometimes referred to as "the first, the second, the third and the fourth luminescent compounds".
[1565] In this embodiment, it is preferred that the first, second, third and fourth luminescent compounds are each independently a luminescent compound exhibiting a maximum peak wavelength of less than 480 nm or exhibiting a maximum peak wavelength of less than 470 nm.
[1566] In this embodiment, it is preferred that the first, second, third and fourth luminescent compounds are each independently a luminescent compound exhibiting a maximum peak wavelength of 430 nm or more, or exhibiting a maximum peak wavelength of 440 nm or more.
[1567] In this embodiment, it is preferred that at least one compound selected from the group consisting of the first, second, third and fourth luminescent compounds is a compound exhibiting fluorescence luminescence; more preferably, the first, second, third and fourth luminescent compounds are all compounds exhibiting fluorescence luminescence.
[1568] In this embodiment, it is preferable that at least one compound selected from the group consisting of the first, second, third and fourth luminescent compounds is a compound that exhibits blue luminescence; more preferably, the first, second, third and fourth luminescent compounds are all compounds that exhibit blue luminescence.
[1569] In this embodiment, it is preferred that at least one compound selected from the group consisting of the first, second, third and fourth luminescent compounds is a compound that does not contain an azazine ring structure in its molecule; more preferably, the first, second, third and fourth luminescent compounds are all compounds that do not contain an azazine ring structure in their molecules.
[1570] Preferably, at least one of the compounds selected from the group consisting of the first, second, third and fourth luminescent compounds is not a boron-containing complex; more preferably, none of the first, second, third and fourth luminescent compounds are boron-containing complexes.
[1571] Preferably, at least one compound selected from the group consisting of the first, second, third and fourth luminescent compounds is not a complex; more preferably, none of the first, second, third and fourth luminescent compounds are complexes.
[1572] In this embodiment, the first, second, third, and fourth luminescent compounds may be the same as or different from each other.
[1573] In this embodiment, it is preferable that the first luminescent compound and the second luminescent compound are the same compound.
[1574] In this embodiment, it is preferable that the third luminescent compound and the fourth luminescent compound are the same compound.
[1575] In this embodiment, it is preferable that the first luminescent compound and the third luminescent compound are the same compound.
[1576] In this embodiment, it is preferable that the second luminescent compound and the fourth luminescent compound are the same compound.
[1577] In this embodiment, it is also preferable that the first, second, third, and fourth luminescent layers contain the same luminescent compound. That is, it is also preferable that the first, second, third, and fourth luminescent compounds are the same compound.
[1578] In one embodiment of the organic EL element, the first, second, third and fourth luminescent compounds are each independently selected from at least one compound chosen from the group consisting of the compound shown in formula (5), the compound shown in formula (6) and the compound shown in formula (3A).
[1579] (The compound shown in formula (5))
[1580] In one embodiment of the organic EL element, the luminescent compound is the compound shown in formula (5) below.
[1581]
[1582] (In the above formula (5),
[1583] By R 501 ~R 507 and R 511 ~R 517 One or more groups consisting of two or more adjacent elements.
[1584] They bond together to form substituted or unsubstituted monocyclic rings.
[1585] They bond together to form substituted or unsubstituted fused rings, or
[1586] They do not bond with each other.
[1587] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 501 ~R 507 and R 511 ~R 517 Each independently
[1588] hydrogen atom,
[1589] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1590] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1591] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1592] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1593] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1594] -O-(R 904 The groups shown in the figure,
[1595] -S-(R 905 The groups shown in the figure,
[1596] -N(R 906 (R) 907 The groups shown in the figure,
[1597] Halogen atoms,
[1598] cyano,
[1599] Nitro,
[1600] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1601] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1602] R 521 and R 522 Each independently
[1603] hydrogen atom,
[1604] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1605] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1606] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1607] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1608] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1609] -O-(R 904 The groups shown in the figure,
[1610] -S-(R 905 The groups shown in the figure,
[1611] -N(R 906 (R) 907 The groups shown in the figure,
[1612] Halogen atoms,
[1613] cyano,
[1614] Nitro,
[1615] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1616] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1617] In luminescent compounds, R 901 R 902 R 903 R 904 R 905 R 906 and R 907 Each independently
[1618] hydrogen atom,
[1619] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1620] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1621] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1622] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1623] Preferably, it is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or
[1624] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[1625] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[1626] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[1627] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[1628] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
[1629] In R905 In the case of multiple Rs, multiple Rs 905 They are the same or different.
[1630] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.
[1631] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.
[1632] "By R" 501 ~R 507 and R 511 ~R 517 "One of the groups consisting of two or more adjacent elements" is, for example, a group composed of R. 501 With R 502 The group composed of R 502 With R 503 The group composed of R 503 With R 504 The group composed of R 505 With R 506 The group composed of R 506 With R 507 The group composed of R 501 With R 502 With R 503 Groups and combinations.
[1633] In one embodiment, the compound represented by formula (5) above is the compound represented by formula (52) below.
[1634]
[1635] (In the above formula (52),
[1636] By R 531 ~R 534 and R 541 ~R 544 One or more groups consisting of two or more adjacent elements.
[1637] They bond together to form substituted or unsubstituted monocyclic rings.
[1638] They bond together to form substituted or unsubstituted fused rings, or
[1639] They do not bond with each other.
[1640] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 531 ~R 534 R 541 ~R544 and R 551 and R 552 Each independently
[1641] hydrogen atom,
[1642] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1643] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1644] R 561 ~R 564 Each independently
[1645] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1646] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1647] Preferably, R 561 ~R 564 Each of the aryl groups is independently substituted or unsubstituted, consisting of 6 to 18 cyclic carbons, more preferably substituted or unsubstituted, consisting of 6 to 14 cyclic carbons, and even more preferably substituted or unsubstituted phenyl or substituted or unsubstituted naphthyl groups.
[1648] (The compound shown in formula (6))
[1649] In one embodiment of the organic EL element, the luminescent compound is the compound shown in formula (6) below.
[1650]
[1651] (In the above formula (6),
[1652] Rings a, b, and c are each independently...
[1653] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or
[1654] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1655] R 601 With R 602 Each of them independently does not form a substituted or unsubstituted heterocycle, or they bond with the aforementioned a-ring, b-ring, or c-ring to form a substituted or unsubstituted heterocycle.
[1656] R does not form the aforementioned substituted or unsubstituted heterocycles 601 and R 602 Each independently
[1657] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1658] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1659] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1660] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1661] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1662] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1663] In one embodiment of the organic EL element, the a ring, b ring, and c ring are rings fused with the fused 2-ring structure at the center of the above formula (6) consisting of boron atoms and 2 nitrogen atoms (substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 cyclic carbons or substituted or unsubstituted heterocycles with 5 to 50 cyclic atoms).
[1664] The "aromatic hydrocarbon rings" of the a, b, and c rings have the same structure as compounds formed by introducing hydrogen atoms into the "aryl" group.
[1665] The "aromatic hydrocarbon ring" of ring a contains three carbon atoms on the fused 2-ring structure in the center of formula (6) above as cyclic atoms.
[1666] The "aromatic hydrocarbon rings" of rings b and c contain two carbon atoms on the fused 2-ring structure in the center of formula (6) above as cyclic atoms.
[1667] As a specific example of "a cyclic aromatic hydrocarbon ring with 6 to 50 carbon atoms, whether substituted or unsubstituted", compounds formed by introducing hydrogen atoms into the "aryl" group described in Specific Example Group G1 can be cited.
[1668] The "heterocyclic" rings a, b, and c have the same structure as compounds formed by introducing hydrogen atoms into the aforementioned "heterocyclic groups".
[1669] The "heterocycle" of ring a includes three carbon atoms in the fused 2-ring structure at the center of formula (6) as cyclic atoms. The "heterocycles" of rings b and c include two carbon atoms in the fused 2-ring structure at the center of formula (6) as cyclic atoms. As a specific example of "heterocycles with 5 to 50 substituted or unsubstituted cyclic atoms", compounds formed by introducing hydrogen atoms into the "heterocyclic group" described in specific example group G2 can be cited.
[1670] R 601 and R 602Each ring can independently bond with ring a, ring b, or ring c to form substituted or unsubstituted heterocycles. In this case, the heterocycle contains the nitrogen atom from the fused 2-ring structure at the center of equation (6). The heterocycle may also contain heteroatoms other than the nitrogen atom. R 601 and R 602 Specifically, bonding with ring a, ring b, or ring c refers to the bonding between atoms constituting ring a, ring b, or ring c and atoms constituting ring R. 601 and R 602 The atoms are bonded together. For example, it could also be R. 601 fused with α ring to form R 601 A nitrogen-containing heterocycle in which two rings (or three or more rings) are fused with the a ring. Specific examples of such nitrogen-containing heterocycles include compounds corresponding to the heterocyclic groups in Specific Example Group G2 that contain nitrogen and are fused with two or more rings.
[1671] R 601 Cases involving b-ring bonding, R 602 The case of α-ring bonding and R 602 The situation regarding bonding with the c-ring is the same as described above.
[1672] R 601 and R 602 Each ring can also be independent of being bonded to the a-ring, b-ring, or c-ring.
[1673] In one embodiment, ring a, ring b, and ring c in formula (6) above are each independently a substituted or unsubstituted aromatic hydrocarbon ring with 6 to 50 carbon atoms.
[1674] In one embodiment, rings a, b, and c in formula (6) above are each independently a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring.
[1675] In one implementation, R in equation (6) above 601 and R 602 Each is independently a substituted or unsubstituted aryl group having 6 to 50 carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms, preferably a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
[1676] In one embodiment, the compound represented by formula (6) above is the compound represented by formula (62) below.
[1677]
[1678] (In the above formula (62),
[1679] R 601A With selection from R 611 and R 621One or more of them are bonded together to form a substituted or unsubstituted heterocycle, or they do not form a substituted or unsubstituted heterocycle.
[1680] R 602A With selection from R 613 and R 614 One or more of them are bonded together to form a substituted or unsubstituted heterocycle, or they do not form a substituted or unsubstituted heterocycle.
[1681] R does not form the aforementioned substituted or unsubstituted heterocycles 601A and R 602A Each independently
[1682] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1683] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1684] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1685] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1686] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1687] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1688] By R 611 ~R 621 One or more groups consisting of two or more adjacent elements.
[1689] They bond together to form substituted or unsubstituted monocyclic rings.
[1690] They bond together to form substituted or unsubstituted fused rings, or
[1691] They do not bond with each other.
[1692] R that does not form the aforementioned substituted or unsubstituted heterocyclic rings, does not form the aforementioned substituted or unsubstituted monocyclic rings, and does not form the aforementioned substituted or unsubstituted fused rings. 611 ~R 621 Each independently
[1693] hydrogen atom,
[1694] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1695] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1696] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1697] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1698] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1699] -O-(R 904 The groups shown in the figure,
[1700] -S-(R 905 The groups shown in the figure,
[1701] -N(R 906 (R) 907 The groups shown in the figure,
[1702] Halogen atoms,
[1703] cyano,
[1704] Nitro,
[1705] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1706] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1707] (In the above equation (62), R) 901 R 902 R 903 R 904 R 905 R 906 and R 907 Each independently
[1708] hydrogen atom,
[1709] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1710] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1711] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1712] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1713] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[1714] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[1715] In R 903 In the case of multiple Rs, multiple Rs903 They are the same or different.
[1716] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
[1717] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.
[1718] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.
[1719] In R 907 In the case of multiple Rs, multiple Rs 907 (They may be the same or different.)
[1720] R in equation (62) above 601A and R 602A Each is R in relation to the above equation (6). 601 and R 602 The corresponding functional group. For example, it can be R. 601A With R 611 These are nitrogen-containing heterocycles that are bonded together to form a fused two-ring (or three-ring or more) fused ring, comprising the rings containing the rings and a benzene ring corresponding to the α-ring. Specific examples of such nitrogen-containing heterocycles include compounds corresponding to the nitrogen-containing fused heterocyclic groups in Specific Example Group G2. R 601A With R 621 Bonding situation, R 602A With R 613 Bonding conditions and R 602A With R 614 The bonding situation is the same as above.
[1721] By R 611 ~R 621 One or more of the adjacent groups can be bonded together to form a substituted or unsubstituted monocyclic ring, or bonded together to form a substituted or unsubstituted fused ring. For example, R can be 611 With R 612 The bonds can be combined to form structures consisting of six-membered rings such as benzene rings, indole rings, pyrrole rings, benzofuran rings, or benzothiophene rings. The resulting fused rings can be naphthalene rings, carbazole rings, indole rings, dibenzofuran rings, or dibenzothiophene rings.
[1722] In one embodiment, the compound represented by formula (6) above is the compound represented by formula (42-2) below.
[1723]
[1724] (In the above equation (42-2), R) 611 ~R 617 R 601A and R 602A Each independently relates to R in the above equation (62). 611 ~R 617 R 601A and R 602A Same meaning
[1725] X4 is an oxygen atom or a sulfur atom.
[1726] By R 701 ~R 704 One or more groups consisting of two or more adjacent elements.
[1727] They bond together to form substituted or unsubstituted monocyclic rings.
[1728] They bond together to form substituted or unsubstituted fused rings, or
[1729] They do not bond with each other.
[1730] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 701 ~R 704 Each independently
[1731] hydrogen atom,
[1732] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1733] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1734] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1735] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1736] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1737] -O-(R 904 The groups shown in the figure,
[1738] -S-(R 905 The groups shown in the figure,
[1739] -N(R 906 (R) 907 The groups shown in the figure,
[1740] Halogen atoms,
[1741] cyano,
[1742] Nitro,
[1743] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1744] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1745] In the above equation (42-2), R 901 R 902 R 903 R 904 R 905 R 906 and R 907 Each independently relates to R in the above equation (62). 901 R 902 R 903 R 904 R 905 R 906 and R 907 The meaning is the same.
[1746] (The compound shown in formula (3A))
[1747] In one embodiment of the organic EL element, the luminescent compound is a compound represented by the following formula (3A).
[1748]
[1749] (In the above formula (3A),
[1750] By Ra 301 Ra 302 Ra 303 Ra 304 Ra 305 Ra 306 Ra 307 Ra 308 Ra 309 and Ra 310 One or more groups consisting of two or more adjacent elements.
[1751] They bond together to form substituted or unsubstituted monocyclic rings.
[1752] They bond together to form substituted or unsubstituted fused rings, or
[1753] They do not bond with each other.
[1754] Ra 301 ~Ra 310 At least one of them is a monovalent group as shown in formula (31A) below.
[1755] Ra does not form the above-mentioned monocyclic ring, does not form the above-mentioned fused ring, and is not a monovalent group as shown in formula (31A) below. 301 ~Ra 310 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, or a -Si(R) group. 901 (R) 902 (R) 903 The group shown is -O-(R) 904 The group shown is -S-(R) 905 The group shown is -N(R) 906 (R) 907 The groups shown in the diagram include halogen atoms, cyano groups, nitro groups, substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms.
[1756]
[1757] (In the above formula (31A), Ara 301 and Ara 302 Each is independently a substituted or unsubstituted aryl group with 6 to 50 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 cyclic atoms. La 301 La 302 and La 303 Each is an arylene group with 6 to 30 carbon atoms, either individually single-bonded, substituted, or unsubstituted, or a divalent heterocyclic group with 5 to 30 cyclic atoms. * indicates the bonding position in the pyrene ring in formula (3A) above.
[1758] (Specific examples of luminescent compounds)
[1759] The following are specific examples of luminescent compounds. These are merely illustrative examples, and the luminescent compounds are not limited to the specific examples described below.
[1760]
[1761]
[1762] (The correlation between the host material and the luminescent compound)
[1763] In this embodiment, it is preferable that the triplet energy T1(H1) of the first host material and the triplet energy T1(D1) of the first luminescent compound satisfy the following mathematical formula (Mathematical Formula 1B).
[1764] T1(D1)>T1(H1) …(Mathematical Expression 1B)
[1765] Because the first host material and the first luminescent compound satisfy the mathematical formula (Formula 1B), the triplet excitons generated in the first luminescent layer do not move on the first luminescent compound with higher triplet energy but on the first host material, and therefore can easily move to the second luminescent layer.
[1766] In this embodiment, it is preferable that the singlet state energy S1(H1) of the first host material and the singlet state energy S1(D1) of the first luminescent compound satisfy the following mathematical formula (Formula 1C). The singlet state energy S1 refers to the energy difference between the lowest excited singlet state and the ground state.
[1767] S1(H1)>S1(D1) …(Mathematical expression 1C)
[1768] By satisfying the mathematical formula (Formula 1C) between the first host material and the first luminescent compound, the singlet excitons generated on the first host material can easily transfer energy from the first host material to the first luminescent compound, which helps the first luminescent compound to exhibit fluorescence.
[1769] In this embodiment, it is preferable that the singlet energy S1(H2) of the second host material and the singlet energy S1(D2) of the second luminescent compound satisfy the following mathematical formula (Mathematical Formula 1D).
[1770] S1(H2)>S1(D2) …(Mathematical expression 1D)
[1771] In this embodiment, by satisfying the above mathematical formula (Mathematical Formula 1D) relationship between the second luminescent compound and the second host material, since the singlet energy of the second luminescent compound is less than that of the second host material, the singlet exciton generated by the TTF phenomenon undergoes energy transfer from the second host material to the second luminescent compound, which helps the second luminescent compound to exhibit fluorescence.
[1772] In this embodiment, it is preferable that the triplet energy T1(D2) of the second luminescent compound and the triplet energy T1(H2) of the second host material satisfy the following mathematical formula (Formula 1E).
[1773] T1(D2)>T1(H2) …(Mathematical expression 1E)
[1774] In this embodiment, because the second luminescent compound and the second host material satisfy the mathematical formula (Formula 1E), when triplet excitons generated in the first luminescent layer move to the second luminescent layer, they transfer energy to the molecules of the second host material instead of to the second luminescent compound, which has a higher triplet energy. Furthermore, triplet excitons generated by the recombination of holes and electrons on the second host material do not move to the second luminescent compound, which has a higher triplet energy. Triplet excitons generated by recombination on the molecules of the second luminescent compound rapidly transfer energy to the molecules of the second host material. Because the triplet excitons on the second host material do not move to the second luminescent compound but instead collide effectively with each other via the TTF phenomenon, singlet excitons are generated.
[1775] In this embodiment, it is preferable that the triplet energy T1(H3) of the third host material and the triplet energy T1(D3) of the third luminescent compound satisfy the following mathematical formula (Mathematical Formula 2B).
[1776] T1(D3)>T1(H3) …(Mathematical expression 2B)
[1777] Because the third host material and the third luminescent compound satisfy the mathematical formula (Formula 2B), the triplet excitons generated in the third luminescent layer do not move on the third luminescent compound with higher triplet energy but on the third host material, and therefore can easily move to the fourth luminescent layer.
[1778] In this embodiment, it is preferable that the singlet energy S1(H3) of the third host material and the singlet energy S1(D3) of the third luminescent compound satisfy the following mathematical formula (Mathematical Formula 2C).
[1779] S1(H3)>S1(D3) …(Mathematical expression 2C)
[1780] By satisfying the mathematical formula (Formula 2C) between the third host material and the third luminescent compound, the singlet exciton generated on the third host material can easily transfer energy from the third host material to the third luminescent compound, which helps the third luminescent compound to exhibit fluorescence.
[1781] In this embodiment, it is preferable that the triplet energy T1(D4) of the fourth luminescent compound and the triplet energy T1(H4) of the fourth host material satisfy the following mathematical formula (Mathematical Formula 2D).
[1782] T1(D4)>T1(H4) …(Mathematical expression 2D)
[1783] In this embodiment, because the fourth luminescent compound and the fourth host material satisfy a mathematical formula (Formula 2D), when triplet excitons generated in the third luminescent layer move to the fourth luminescent layer, they transfer energy to the molecules of the fourth host material instead of to the fourth luminescent compound, which has a higher triplet energy. Furthermore, triplet excitons generated by the recombination of holes and electrons on the fourth host material do not move to the fourth luminescent compound, which has a higher triplet energy. Triplett excitons generated by recombination on the molecules of the fourth luminescent compound rapidly transfer energy to the molecules of the fourth host material. Because the triplet excitons on the fourth host material do not move to the fourth luminescent compound, but instead collide effectively with each other on the fourth host material via the TTF phenomenon, singlet excitons are generated.
[1784] In this embodiment, it is preferable that the singlet energy S1(H4) of the fourth host material and the singlet energy S1(D4) of the fourth luminescent compound satisfy the following mathematical formula (Mathematical Formula 2E).
[1785] S1(H4)>S1(D4) …(Mathematical expression 2E)
[1786] In this embodiment, by satisfying the above mathematical formula (Mathematical Formula 2E) relationship between the fourth luminescent compound and the fourth host material, since the singlet energy of the fourth luminescent compound is less than that of the fourth host material, the singlet exciton generated by the TTF phenomenon undergoes energy transfer from the fourth host material to the fourth luminescent compound, which contributes to the fluorescence of the fourth luminescent compound.
[1787] In this embodiment, it is also preferred that the first light-emitting layer and the second light-emitting layer are directly connected.
[1788] In this specification, the layer structure in which "the first light-emitting layer and the second light-emitting layer are directly connected" may include, for example, any one of the following schemes (LS1), (LS2) and (LS3).
[1789] (LS1) A scheme in which a region is formed where the first host material and the second host material coexist during the vapor deposition process of the compound involved in the first light-emitting layer and the vapor deposition process of the compound involved in the second light-emitting layer, and the region exists at the interface between the first light-emitting layer and the second light-emitting layer.
[1790] (LS2) In the case where the first light-emitting layer and the second light-emitting layer contain a luminescent compound, a region in which the first host material, the second host material and the luminescent compound coexist is generated during the vapor deposition process of the compound involved in the first light-emitting layer and the vapor deposition process of the compound involved in the second light-emitting layer, and the region exists at the interface between the first light-emitting layer and the second light-emitting layer.
[1791] (LS3) In the case where the first light-emitting layer and the second light-emitting layer contain a luminescent compound, a region formed by the luminescent compound, a region formed by the first host material, or a region formed by the second host material is generated during the vapor deposition process of the compound involved in the first light-emitting layer and the vapor deposition process of the compound involved in the second light-emitting layer, and the region exists at the interface between the first light-emitting layer and the second light-emitting layer.
[1792] In this embodiment, it is also preferred that the third light-emitting layer and the fourth light-emitting layer are directly connected.
[1793] In this specification, the layer structure in which "the third light-emitting layer is directly connected to the fourth light-emitting layer" may include, for example, any of the following schemes (LS4), (LS5) and (LS6).
[1794] (LS4) A scheme in which a region is formed where the third and fourth base materials coexist during the vapor deposition processes of the compound involved in the third luminescent layer and the compound involved in the fourth luminescent layer, and such region exists at the interface between the third and fourth luminescent layers.
[1795] (LS5) In the case where the third and fourth light-emitting layers contain luminescent compounds, a region in which the third host material, the fourth host material and the luminescent compound coexist is generated during the vapor deposition process of the compound involved in the third light-emitting layer and the vapor deposition process of the compound involved in the fourth light-emitting layer, and this region exists at the interface between the third and fourth light-emitting layers.
[1796] (LS6) In the case where the third and fourth light-emitting layers contain a luminescent compound, a region formed by the luminescent compound, a region formed by the third host material, or a region formed by the fourth host material is generated during the vapor deposition process of the compound involved in the third light-emitting layer and the vapor deposition process of the compound involved in the fourth light-emitting layer, and the region exists at the interface between the third and fourth light-emitting layers.
[1797] (Containment rate in the luminescent layer)
[1798] In one embodiment of the organic EL element, the content of the first luminescent compound in the first luminescent layer is 0.5% by mass or more of the total mass of the first luminescent layer.
[1799] In one embodiment of the organic EL element, the content of the first luminescent compound in the first luminescent layer is 10% or less, 7% or less, or 5% or less of the total mass of the first luminescent layer.
[1800] In one embodiment of the organic EL element, the content of the first host material in the first light-emitting layer is 60% or more, 70% or more, 80% or more, 90% or more, or 95% or more of the total mass of the first light-emitting layer.
[1801] In one embodiment of the organic EL element, the content of the first host material in the first light-emitting layer is 99.5% or less or 99% or less of the total mass of the first light-emitting layer.
[1802] When the first luminescent layer contains the first host material and the first luminescent compound, the upper limit of the total content of the first host material and the first luminescent compound is 100% by mass.
[1803] In this embodiment, the first luminescent layer may contain only the first host material and the first luminescent compound.
[1804] In one embodiment of the organic EL element, the content of the third host material and the third luminescent compound in the third luminescent layer can be applied to the range of the content of the first host material and the first luminescent compound in the first luminescent layer described above.
[1805] In this embodiment, the third luminescent layer may contain only the third host material and the third luminescent compound.
[1806] In one embodiment of the organic EL element, the content of the second luminescent compound in the second luminescent layer is 0.5% by mass or more of the total mass of the second luminescent layer.
[1807] In one embodiment of the organic EL element, the content of the second luminescent compound in the second luminescent layer is 10% or less, 7% or less, or 5% or less of the total mass of the second luminescent layer.
[1808] In one embodiment of the organic EL element, the content of the second host material in the second light-emitting layer is 60% or more, 70% or more, 80% or more, 90% or more, or 95% or more of the total mass of the second light-emitting layer.
[1809] In one embodiment of the organic EL element, the content of the second host material in the second light-emitting layer is 99.5% or less or 99% or less of the total mass of the second light-emitting layer.
[1810] When the second luminescent layer contains the second host material and the second luminescent compound, the upper limit of the total content of the second host material and the second luminescent compound is 100% by mass.
[1811] In this embodiment, the second luminescent layer may contain only the second host material and the second luminescent compound.
[1812] In one embodiment of the organic EL element, the content of the fourth host material and the fourth luminescent compound in the fourth luminescent layer can be within the range of the content of the second host material and the second luminescent compound in the second luminescent layer described above.
[1813] In this embodiment, the fourth luminescent layer may contain only the fourth host material and the fourth luminescent compound.
[1814] (Thickness of the light-emitting layer)
[1815] In one embodiment of the organic EL device, the thickness of the first light-emitting layer and the third light-emitting layer is each independently 3 nm or more. If the thickness of the first light-emitting layer and the third light-emitting layer is 3 nm or more, it is sufficient to induce recombination of holes and electrons in the first light-emitting layer and the third light-emitting layer.
[1816] In one embodiment of the organic EL device, the thickness of the first and third light-emitting layers is independently 15 nm or less. If the thickness of the first and third light-emitting layers is 15 nm or less, it is thin enough to cause the movement of triplet excitons from the first to the second light-emitting layer and from the third to the fourth light-emitting layer.
[1817] In one embodiment of the organic EL element, the thickness of the first light-emitting layer and the third light-emitting layer is independently 3 nm or more and 15 nm or less.
[1818] In one embodiment of the organic EL device, the thicknesses of the second and fourth emissive layers are each independently 5 nm or more, or 10 nm or more. If the thicknesses of the second and fourth emissive layers are 5 nm or more, it is easier to suppress the return of triplet excitons that have migrated from the first to the second emissive layer to the first emissive layer, and vice versa. Furthermore, if the thicknesses of the second and fourth emissive layers are 5 nm or more, it is possible to sufficiently separate the triplet excitons from the recombination portions in the first and third emissive layers.
[1819] In the organic EL element of this embodiment, it is preferable that the film thickness of the second light-emitting layer and the fourth light-emitting layer are each independently 25 nm or less. If the film thickness of the second light-emitting layer and the fourth light-emitting layer is 25 nm or less, the density of triplet excitons in the second light-emitting layer and the fourth light-emitting layer can be increased, making it easier to induce the TTF phenomenon.
[1820] In one embodiment of the organic EL element, the thickness of the second and fourth light-emitting layers is independently 5 nm or more and 25 nm or less.
[1821] In the organic EL element involved in this embodiment, it is preferable that the thickness of the first light-emitting layer is smaller than the thickness of the second light-emitting layer, and the thickness of the third light-emitting layer is smaller than the thickness of the fourth light-emitting layer.
[1822] <Charge Generation Region>
[1823] In this embodiment, it is preferable that the charge generation region is disposed between at least one pair of light-emitting units selected from two or more light-emitting units.
[1824] In this embodiment, it is preferable that a first charge generation region is disposed between the first light-emitting unit and the second light-emitting unit.
[1825] In this embodiment, it is preferred that each charge generation region independently comprises at least one charge generation layer. It is also preferred that at least any one of the charge generation regions comprises two or more charge generation layers. Furthermore, it is preferred that each charge generation region independently comprises two or more charge generation layers. The charge generation layer is sometimes also referred to as an intermediate layer, intermediate electrode, intermediate conductive layer, electron extraction layer, connecting layer, or intermediate insulating layer.
[1826] The charge generation region is the region in which at least one of holes and electrons is generated when a voltage is applied to the organic EL element. The charge generation region supplies electrons to the layer located on the anode side of the charge generation region. Additionally, the charge generation region supplies holes to the layer located on the cathode side of the charge generation region.
[1827] In this embodiment, it is preferred that at least any one charge generation region includes a first charge generation layer and a second charge generation layer as two charge generation layers.
[1828] The first charge generation region can consist of one charge generation layer or two charge generation layers, including the first charge generation layer and the second charge generation layer.
[1829] In this embodiment, it is preferable that a first charge generation region is included between the first light-emitting unit and the second light-emitting unit, and the first charge generation region includes a first charge generation layer and a second charge generation layer disposed at a position closer to the second light-emitting unit than the first charge generation layer.
[1830] In this embodiment, when the charge generation region is composed of multiple charge generation layers, it is preferable that the charge generation region has an N-type charge generation layer for injecting electrons into the light-emitting unit and a P-type charge generation layer for injecting holes into the light-emitting unit. Preferably, the N-type charge generation layer is directly connected to the light-emitting unit disposed on the anode side relative to the charge generation region. Preferably, the P-type charge generation layer is directly connected to the light-emitting unit disposed on the cathode side relative to the charge generation region.
[1831] In this embodiment, it is preferred that one of the N-type charge generation layer and the P-type charge generation layer is the first charge generation layer.
[1832] In this embodiment, it is also preferred that the N-type charge generation layer is the first charge generation layer and the P-type charge generation layer is the second charge generation layer.
[1833] In this embodiment, as a material that can be used for the charge generation layer in the charge generation region, examples include known materials that can be used for the charge generation layer of a series-connected organic EL element.
[1834] In this embodiment, it is preferable that the first charge-generating layer contains an electron transport region material. The electron transport region material contained in the first charge-generating layer is the same compound as or a different compound from the electron transport region material contained in the layers within the electron transport region. Preferably, the first charge-generating layer contains at least one derivative selected from the group consisting of phenanthroline derivatives, imidazole derivatives, benzimidazole derivatives, azazine derivatives, and carbazole derivatives.
[1835] In this embodiment, the first charge-generating layer may contain at least one selected from the group consisting of metals and metal compounds.
[1836] In this embodiment, it is also preferred that the first charge generation layer contains an electron transport region material and at least one selected from the group consisting of metals and metal compounds.
[1837] In this embodiment, the first charge-generating layer may contain at least one metal selected from the group consisting of rare earth metals, alkali metals, and alkaline earth metals. The first charge-generating layer may contain at least one metal selected from the group consisting of ytterbium, erbium, lithium, cesium, magnesium, and calcium. The first charge-generating layer may contain at least one metal compound selected from the group consisting of compounds of alkali metals and compounds of alkaline earth metals. The first charge-generating layer may contain a metal compound selected from at least one metal compound chosen from the group consisting of lithium 8-(hydroxyquinoline) (Liq), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium 2-(2-pyridyl)phenol (LiPP), lithium 2-(2-pyridyl)-3-hydroxypyridine (LiPPy), lithium 4-phenyl-2-(2-pyridyl)phenol (LiPPP), lithium oxide (LiOx), and cesium carbonate.
[1838] In this embodiment, it is preferred that the second charge-generating layer contains a hole transport region material and an acceptor material. The hole transport region material contained in the second charge-generating layer is the same compound as the hole transport region material contained in the layer within the hole transport region, or they are different compounds. Preferably, the second charge-generating layer contains at least one derivative selected from the group consisting of aromatic amine derivatives and carbazole derivatives.
[1839] <Hole transport region>
[1840] In this embodiment, preferably, each of the two or more light-emitting units independently includes a hole transport region. Each hole transport region independently includes one or more layers. In this embodiment, preferably, the hole transport region in each light-emitting unit independently includes at least one layer selected from the group consisting of an electron blocking layer, a hole transport layer, and a hole injection layer.
[1841] In this embodiment, preferably, the first light-emitting unit includes a first hole transport region. Preferably, the second light-emitting unit includes a second hole transport region. Preferably, the first hole transport region is disposed between the first light-emitting region and the anode. When the first light-emitting unit is the light-emitting unit disposed closest to the anode, preferably, the first hole transport region is directly connected to the anode.
[1842] In this embodiment, it is preferable that the second hole transport region is disposed between the first light-emitting region and the second light-emitting region. When a first charge-generating region is disposed between the first light-emitting unit and the second light-emitting unit, it is preferable that the second hole transport region is disposed between the first charge-generating region and the second light-emitting region. In this case, the second hole transport region is preferably directly connected to the first charge-generating region, and more preferably directly connected to the second charge-generating layer. Preferably, the second hole transport region is directly connected to the second light-emitting region.
[1843] In this embodiment, preferably, the first light-emitting unit includes a first hole transport region, the second light-emitting unit includes a second hole transport region, the first hole transport region is contained between the anode and the first light-emitting region, the second hole transport region is contained between the first charge generation region and the second light-emitting region, the first hole transport region and the second hole transport region each independently contain one or more layers, and at least one of the one or more layers contained in the first hole transport region and at least one of the one or more layers contained in the second hole transport region each independently contain a monoamine compound.
[1844] In this embodiment, preferably, the first hole transport region and the second hole transport region each independently include at least one selected from the group consisting of an electron blocking layer, a hole transport layer and a hole injection layer.
[1845] In this embodiment, it is preferable that the layers in the hole transport region (e.g., electron blocking layer, hole transport layer, and hole injection layer) each independently contain hole transport region material.
[1846] (Hole transport region material)
[1847] In this embodiment, the material contained in the hole transport region is referred to as the hole transport region material. Preferably, the hole transport region material is a material that can be used in layers that may be contained in the hole transport region (e.g., an electron blocking layer, a hole transport layer, and a hole injection layer). The hole transport region material can also be used in the charge generation region.
[1848] In one embodiment of the organic EL element, the hole transport region material may also be a compound selected from at least one of the compounds shown in formula (C1) and formula (C3).
[1849]
[1850] (In the above formula (C1),
[1851] L A1 LA2 and L A3 Each independently
[1852] single bond,
[1853] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms
[1854] Substituted or unsubstituted divalent heterocyclic groups with 5 to 50 cyclic atoms, or
[1855] A divalent group is formed by bonding two or three groups from the group consisting of a freely substituted or unsubstituted aryl group with 6 to 50 carbon atoms and a substituted or unsubstituted divalent heterocyclic group with 5 to 50 carbon atoms.
[1856] Ar 111 Ar 112 and Ar 113 Each independently
[1857] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1858] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1859] -Si(R C1 (R) C2 (R) C3 ),
[1860] R C1 R C2 and R C3 Each is independently a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic formation.
[1861] In R C1 In the case of multiple Rs, multiple Rs C1 They are the same or different.
[1862] In R C2 In the case of multiple Rs, multiple Rs C2 They are the same or different.
[1863] In R C3 In the case of multiple Rs, multiple Rs C3 (They may be the same or different.)
[1864]
[1865] (In the above formula (C3),
[1866] L C1 L C2 L C3 and L C4 Each independently
[1867] single bond,
[1868] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1869] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1870] n² is 1, 2, 3, or 4.
[1871] When n2 is 1, L C5 for
[1872] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1873] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1874] When n2 is 2, 3, or 4, multiple L C5 They are the same or different.
[1875] When n2 is 2, 3, or 4, multiple L C5
[1876] They bond together to form substituted or unsubstituted monocyclic rings.
[1877] They bond together to form substituted or unsubstituted fused rings, or
[1878] They do not bond with each other.
[1879] L does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. C5 for
[1880] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1881] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1882] Ar 131 Ar 132 Ar 133 and Ar 134 Each independently
[1883] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1884] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1885] -Si(R C1 (R) C2 (R) C3 ),
[1886] R C1 R C2 and R C3 Each is independently a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic formation.
[1887] In R C1 In the case of multiple Rs, multiple Rs C1 They are the same or different.
[1888] In R C2 In the case of multiple Rs, multiple Rs C2 They are the same or different.
[1889] In R C3 In the case of multiple Rs, multiple Rs C3 (They may be the same or different.)
[1890] In one embodiment of the organic EL element, the first amino group represented by formula (C3-1) in the compound represented by formula (C3) above is the same as the second amino group represented by formula (C3-2).
[1891]
[1892] (In the above equations (C3-1) and (C3-2), * represents L respectively.) C5 (The bonding location.)
[1893] In one embodiment of the organic EL element, the first amino group represented by formula (C3-1) and the second amino group represented by formula (C3-2) can be different groups from each other.
[1894] Preferably, in this embodiment, the hole transport region material is an amine compound selected from at least one of the following groups: a monoamine compound having one substituted or unsubstituted amino group in the molecule, a diamine compound having two substituted or unsubstituted amino groups in the molecule, a triamine compound having three substituted or unsubstituted amino groups in the molecule, and a tetraamine compound having four substituted or unsubstituted amino groups in the molecule.
[1895] In this embodiment, the hole transport region material is more preferably a monoamine compound having one substituted or unsubstituted amino group in the molecule, or a diamine compound having two substituted or unsubstituted amino groups in the molecule, and more preferably a monoamine compound having one substituted or unsubstituted amino group in the molecule.
[1896] (Specific examples of materials in the hole transport region)
[1897] Specific examples of hole transport region materials include the following compounds. However, the present invention is not limited to these specific examples of hole transport region materials.
[1898]
[1899]
[1900] (Electron blocking layer)
[1901] Preferably, the electron blocking layer is a layer that transports holes and prevents electrons from reaching layers further anode-side than the electron blocking layer (e.g., hole transport layers).
[1902] In the organic EL element of this embodiment, the electron blocking layer contains a compound such as a known compound for electron blocking layers, preferably a compound selected from at least one of the groups consisting of aromatic amine compounds and carbazole derivatives. Alternatively, the compound contained in the electron blocking layer can be a hole transport region material. Furthermore, the compound contained in the electron blocking layer can be a monoamine compound having only one substituted or unsubstituted amino group in the molecule. Additionally, the compound contained in the electron blocking layer can be a compound having a substituted or unsubstituted carbazole group and one substituted or unsubstituted amino group in the molecule.
[1903] An electron blocking layer can be a layer that prevents excitons generated in the light-emitting layer from moving to a layer closer to the anode side than the electron blocking layer (such as a hole transport layer and a hole injection layer), so that the excitation energy does not leak from the light-emitting layer to the surrounding layers.
[1904] (hole injection layer)
[1905] In one embodiment of the organic EL element, a hole injection layer is disposed between the anode and the light-emitting region.
[1906] In one embodiment of the organic EL element, the anode is directly connected to the hole injection layer.
[1907] In one embodiment of the organic EL element, the hole injection layer and the hole transport layer are directly connected.
[1908] A hole injection layer is a layer containing a material with high hole injection capability. Materials with high hole injection capability can include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.
[1909] In addition, examples of substances with high hole injection potential include 4,4',4''-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), and 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviated as TDATA). Aromatic amine compounds such as DNTPD, 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviated as DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviated as PCzPCN1) are among the examples.
[1910] In addition, high-molecular-weight compounds (oligomers, dendritic polymers, polymers, etc.) can also be used as substances with high hole injection capabilities. Examples include poly(N-vinylcarbazole) (PVK), poly(4-vinyltriphenylamine) (PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (Poly-TPD). Furthermore, acid-containing polymers such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can also be used.
[1911] In one embodiment of the organic EL device, a compound (hole transport region material) that can be used in the hole transport layer may also be used in the hole injection layer. In this case, it is preferable that the hole injection layer contains both a hole transport region material and an acceptor material.
[1912] (Subject Material)
[1913] The acceptor material includes at least one of the first ring structure shown in formula (P11) and the second ring structure shown in formula (P12).
[1914]
[1915] (The first ring structure shown in formula (P11) above is fused with at least one ring structure in the molecule of the above acceptor material, which is either a substituted or unsubstituted aromatic hydrocarbon ring with 6 to 50 carbon atoms or a substituted or unsubstituted heterocycle with 5 to 50 cyclic atoms.)
[1916] =Z 10 The structures shown are represented by the following equations: (P11a), (P11b), (P11c), (P11d), (P11e), (P11f), (P11g), (P11h), (P11i), (P11j), (P11k), or (P11m).
[1917]
[1918]
[1919] (In the above formulas (P11a), (P11b), (P11c), (P11d), (P11e), (P11f), (P11g), (P11h), (P11i), (P11j), (P11k) or (P11m), R 11 ~R 14 and R 111 ~R 120 Each independently
[1920] hydrogen atom,
[1921] Halogen atoms,
[1922] hydroxyl,
[1923] cyano,
[1924] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1925] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1926] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1927] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1928] -O-(R 904 The groups shown in the figure,
[1929] -S-(R 905 The groups shown in the figure,
[1930] -N(R 906 (R) 907 The groups shown in the figure,
[1931] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1932] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1933] (In the above formula (P12), Z1 to Z5 are each independently...)
[1934] nitrogen atoms,
[1935] With R 15 Bonded carbon atoms, or
[1936] Carbon atoms bonded to other atoms in the molecule of the aforementioned acceptor material
[1937] At least one of Z1 to Z5 is a carbon atom bonded to other atoms in the molecule of the aforementioned acceptor material.
[1938] R 15 Choose Freedom
[1939] hydrogen atom,
[1940] Halogen atoms,
[1941] cyano,
[1942] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1943] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1944] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1945] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1946] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms
[1947] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1948] -O-(R 904 The groups shown in the figure,
[1949] -S-(R 905 The groups shown in the figure,
[1950] -N(R 906 (R) 907 The groups shown in the figure,
[1951] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1952] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1953] carboxyl,
[1954] Substituted or unsubstituted ester groups
[1955] Substituted or unsubstituted carbamoyl group,
[1956] Nitro, and
[1957] The group consisting of substituted or unsubstituted siloxanes.
[1958] In R 15 In the case of multiple Rs, multiple Rs 15 (They may be the same or different.)
[1959] (In the above-mentioned recipient material, R) 901 ~R 907 Each independently
[1960] hydrogen atom,
[1961] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1962] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1963] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1964] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1965] In R 901 When multiple R exist, multiple R 901 They are the same or different.
[1966] In R 902 When multiple R exist, multiple R 902 They are the same or different.
[1967] In R 903 When multiple R exist, multiple R 903 They are the same or different.
[1968] In R 904 When multiple R exist, multiple R 904 They are the same or different.
[1969] In R 905 When multiple R exist, multiple R 905 They are the same or different.
[1970] In R 906 When multiple R exist, multiple R 906 They are the same or different.
[1971] In R 907 When multiple R exist, multiple R 907 (They may be the same or different.)
[1972] In one embodiment of the organic EL element, the acceptor material has at least one cyano group.
[1973] In one embodiment of the organic EL element, the hole injection layer contains a hole transport region material, the acceptor material is different from the hole transport region material, and the content of the acceptor material in the hole injection layer is less than 50% by mass.
[1974] In one embodiment of the organic EL element, the content of acceptor material in the hole injection layer is 10% by mass or less or 5% by mass or less.
[1975] In one embodiment of the organic EL element, the content of acceptor material in the hole injection layer is 0.5% by mass or more, 1% by mass or more, or 3% by mass or more.
[1976] In one embodiment of the organic EL element, when the hole injection layer contains acceptor material and hole transport region material, the content of the hole transport region material in the hole injection layer is preferably 40% by mass or more, more preferably 45% by mass or more, and even more preferably 50% by mass or more. The content of the hole transport region material in the hole injection layer is preferably 99.5% by mass or less. The combined content of the acceptor material and the hole transport region material in the hole injection layer is 100% by mass or less.
[1977] In this specification, the ester group is selected from at least one group chosen from the group consisting of alkyl ester groups and aryl ester groups.
[1978] The alkyl ester group in this specification is, for example, represented by -C(=O)OR E Indicates. R E For example, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms (preferably 1 to 10 carbon atoms).
[1979] The aryl ester group in this specification is, for example, represented by -C(=O)OR Ar Indicates. R Ar For example, aryl groups with 6 to 30 carbon atoms, whether substituted or unsubstituted.
[1980] In this specification, siloxane refers to a silicon compound group containing an ether bond, such as trimethylsiloxane.
[1981] In this specification, the carbamoyl group is represented by -CONH2. Substituted carbamoyl groups in this specification are, for example, represented by -CONH-Ar. Cor -CONH-R C Ar indicates. C For example, it can be at least one group selected from the group consisting of aryl groups with 6 to 50 (preferably 6 to 10) cyclic carbon atoms (selected free or unsubstituted) and heterocyclic groups with 5 to 50 (preferably 5 to 14) cyclic atoms. C It can be a group formed by bonding a substituted or unsubstituted aryl group with 6 to 50 carbon atoms to a substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms. R C For example, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms (preferably 1 to 6 carbon atoms).
[1982] In the acceptor material, it is also preferred that the groups described as "substituted or unsubstituted" are all "unsubstituted" groups.
[1983] (Specific examples of the subject material)
[1984] Specific examples of acceptor materials include the following compounds. However, the present invention is not limited to these specific examples of acceptor materials.
[1985]
[1986]
[1987] (Hole transport layer)
[1988] The hole transport layer is a layer containing substances with high hole transport capacity.
[1989] In one embodiment of the organic EL element, the hole transport layer contains a hole transport region material.
[1990] In one embodiment of the organic EL element, the hole transport layer may contain a compound different from the hole transport region material described above. For example, the hole transport layer may contain one or more compounds selected from the group consisting of aromatic amine compounds, carbazole derivatives, and anthracene derivatives. Specifically, the hole transport layer may contain 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BAFLP), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N- Aromatic amine compounds such as [phenylamino]biphenyl (abbreviated as DFLDPBi), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviated as TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as MTDATA), or 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB). The substances described herein mainly possess 10 -6 cm 2 Substances with a hole mobility of / (V·s) or higher.
[1991] Hole transport layers can utilize carbazole derivatives such as CBP, CzPA, and PCzPA, as well as anthracene derivatives such as t-BuDNA, DNA, and DPANth. Alternatively, high molecular weight compounds such as poly(N-vinylcarbazole) (PVK) and poly(4-vinyltriphenylamine) (PVTPA) can also be used. Any substance whose hole transport capability is higher than its electron transport capability can be used in the hole transport layer, regardless of the specific materials mentioned above. It should be noted that hole transport layers can be monolayers or multilayers consisting of two or more layers.
[1992] <Electronic transmission area>
[1993] In this embodiment, it is preferable that each of the two or more light-emitting units independently includes an electron transport region. Each electron transport region independently includes one or more layers. In this embodiment, it is preferable that the electron transport region in each light-emitting unit independently includes at least one selected from the group consisting of a hole blocking layer, an electron transport layer, and an electron injection layer.
[1994] In this embodiment, preferably, the first light-emitting unit includes a first electron transport region, and preferably, the second light-emitting unit includes a second electron transport region.
[1995] In this embodiment, it is preferable that the first electron transport region is disposed between the first light-emitting region and the second hole transport region. When a first charge-generating region is disposed between the first light-emitting unit and the second light-emitting unit, it is preferable that the first electron transport region is disposed between the first light-emitting region and the first charge-generating region. In this case, the first electron transport region is preferably directly connected to the first charge-generating region, and more preferably directly connected to the first charge-generating layer.
[1996] In this embodiment, it is preferable that the second electron transport region is disposed between the second light-emitting region and the cathode. When the second light-emitting unit is a light-emitting unit disposed at the position closest to the cathode, it is preferable that the second electron transport region is directly connected to the cathode.
[1997] In this embodiment, preferably, the first electron transport region and the second electron transport region each independently include at least one selected from the group consisting of a hole blocking layer, an electron transport layer and an electron injection layer.
[1998] In this embodiment, each electron transport region may independently contain two or more layers. In this case, it is preferable that the electron transport region includes a hole blocking layer and an electron transport layer. Alternatively, it is also preferable that the electron transport region includes an electron transport layer and an electron injection layer.
[1999] In this embodiment, each electron transport region may independently contain three or more layers. Preferably, the electron transport region contains three layers: a hole blocking layer, an electron transport layer, and an electron injection layer.
[2000] In the organic EL element of this embodiment, preferably, the first light-emitting unit includes a first electron transport region, the second light-emitting unit includes a second electron transport region, the first electron transport region is located between the first light-emitting region and the first charge generation region, the second electron transport region is located between the second light-emitting region and the cathode, the first electron transport region and the second electron transport region each independently include one or more layers, and at least one of the one or more layers included in the first electron transport region and at least one of the one or more layers included in the second electron transport region each independently contain an azazine compound.
[2001] In the organic EL element of this embodiment, it is preferable that the layers in the electron transport region (e.g., hole blocking layer, electron transport layer and electron injection layer) each independently contain electron transport region material.
[2002] (Materials for electron transport regions)
[2003] In the organic EL device according to this embodiment, the material contained in the electron transport region is referred to as the electron transport region material. Preferably, the electron transport region material is a material that can be used in layers (e.g., hole blocking layers, electron transport layers, and electron injection layers) that can be included in the electron transport region. The electron transport region material can also be used in the charge generation region.
[2004] In one embodiment of the organic EL element, it is preferred that the electron transport region material is a nitrogen-containing compound. The nitrogen-containing compound, as the electron transport region material, has at least one of a five-membered ring containing nitrogen atoms and a six-membered ring containing nitrogen atoms.
[2005] In one embodiment of the organic EL element, the electron transport region material is at least one compound selected from the group consisting of imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, and phenanthroline derivatives.
[2006] In one embodiment of the organic EL element, the electron transport region contains at least one compound selected from the group consisting of imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, and phenanthroline derivatives.
[2007] In one embodiment of the organic EL element, the layer contained in the electron transport region may contain at least one selected from the group consisting of metals and metal compounds.
[2008] In one embodiment of the organic EL display device, the layer included in the electron transport region may contain at least any one selected from the group consisting of metals and metal compounds, and the electron transport region material. The metals and metal compounds that the electron transport region may contain have the same meaning as the metals and metal compounds that the first charge generation layer may contain, as described above.
[2009] In this embodiment, when the first charge-generating layer contains a phenanthroline derivative, it is also preferable that the first electron transport region of the first light-emitting unit does not contain a phenanthroline derivative. When the first charge-generating layer contains a phenanthroline derivative, it is also preferable that the first hole-blocking layer and the second light-emitting layer do not contain a phenanthroline derivative.
[2010] (Cavity barrier layer)
[2011] The hole blocking layer is preferably a layer that transports electrons and prevents holes from reaching layers further from the cathode side than the hole blocking layer (e.g., an electron transport layer). The compound contained in the hole blocking layer is, for example, a known compound for hole blocking layers. The compound contained in the hole blocking layer is preferably, for example, an electron transport region material. Furthermore, the compound contained in the hole blocking layer, similar to the compounds for electron transport layers described later, is preferably at least one compound selected from the group consisting of metal complexes, heteroaromatic compounds, and polymeric compounds. Additionally, the compound contained in the hole blocking layer can be, for example, at least one compound selected from the group consisting of imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, and phenanthroline derivatives. In this embodiment, the electron transport region material contained in the hole blocking layer is preferably a diazine derivative or a triazine derivative, more preferably a pyrimidine derivative or a 1,3,5-triazine derivative.
[2012] The hole blocking layer is preferably a layer that prevents excitons generated in the light-emitting layer from moving to layers closer to the cathode side than the hole blocking layer (such as electron transport layers and electron injection layers) so that the excitation energy does not leak from the light-emitting layer to the surrounding layers.
[2013] (Electron transport layer)
[2014] The electron transport layer is a layer containing materials with high electron transport properties. The electron transport region materials mentioned above can be used in the electron transport layer. Additionally, the electron transport layer can use 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) high molecular weight compounds. Specifically, as low molecular weight organic compounds, metal complexes such as Alq, tris(4-methyl-8-hydroxyquinoline)aluminum (abbreviated: Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (abbreviated: BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to metal complexes, heteroaromatic compounds such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviated as p-EtTAZ), phenanthroline (abbreviated as BPhen), copper hydroxide (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)zirconia (abbreviated as BzOs) can also be used. The substances described herein mainly possess 10 -6 cm2 Substances with an electron mobility of / (V·s) or higher.
[2015] Alternatively, polymeric compounds can be used in the electron transport layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy) can be used.
[2016] In the organic EL element involved in this embodiment, it is preferable that the electron transport layer contains an azazine derivative as the electron transport region material.
[2017] In the organic EL element involved in this embodiment, the electron transport region material is preferably a diazine derivative or a triazine derivative, more preferably a pyrimidine derivative or a 1,3,5-triazine derivative.
[2018] It should be noted that any substance with higher electron transport capacity than hole transport capacity can also be used as the electron transport layer, even if it is a different substance than those mentioned above. Furthermore, the electron transport layer can be a single layer or a multilayer structure consisting of two or more layers.
[2019] Besides the electron transport region materials described above, other specific examples of electron transport region materials include the following compounds. However, the present invention is not limited to these specific examples of electron transport region materials.
[2020]
[2021]
[2022]
[2023]
[2024] (Phenanthroline derivatives)
[2025] Preferably, the phenanthrene derivative is a compound having at least one group represented by formula (21) below and represented by formula (20) below.
[2026]
[2027] (In the above formula (20),
[2028] X 21 ~X 28 Each independently consists of a nitrogen atom and CR. 21 Or carbon atoms bonded to the group shown in formula (21) above,
[2029] X 21 ~X 28 At least one of them is a carbon atom bonded to the group shown in formula (21) above.
[2030] When there are multiple groups represented by the above formula (21), the multiple groups represented by the above formula (21) may be the same as or different from each other.
[2031] Composed of multiple R 21 One or more groups consisting of two or more adjacent elements.
[2032] They bond together to form substituted or unsubstituted monocyclic rings.
[2033] They bond together to form substituted or unsubstituted fused rings, or
[2034] They do not bond with each other.
[2035] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 21 Each independently
[2036] hydrogen atom,
[2037] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2038] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[2039] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2040] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2041] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2042] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2043] -O-(R 904 The groups shown in the figure,
[2044] -S-(R 905 The groups shown in the figure,
[2045] -N(R 906 (R) 907 The groups shown in the figure,
[2046] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[2047] -C(=O)R 931 The groups shown
[2048] -COOR 932 The groups shown
[2049] -S(=O)2R 933 The groups shown
[2050] -B(R 934 (R) 935 The groups shown in the figure,
[2051] -P(=O)(R 936 (R) 937 The groups shown in the figure,
[2052] Halogen atoms,
[2053] cyano,
[2054] Nitro,
[2055] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2056] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2057] (In the above formula (21),
[2058] Ar2 is
[2059] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2060] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2061] p is 1, 2, 3, 4 or 5.
[2062] When there are two or more Ar2 atoms, the two or more Ar2 atoms are either the same or different from each other.
[2063] L2 is a single bond or a linking group.
[2064] L2, as a linking group, is
[2065] Substituted or unsubstituted polyvalent aliphatic hydrocarbon groups with 1 to 50 carbon atoms, in straight-chain, branched, or cyclic form.
[2066] Substituted or unsubstituted polyvalent aromatic hydrocarbon groups with 6 to 50 carbon atoms,
[2067] Substituted or unsubstituted polyvalent heterocyclic groups with 5 to 50 cyclic atoms, or
[2068] A multivalent linked group formed by bonding two or three groups selected from the above-mentioned multivalent aromatic hydrocarbon groups and multivalent heterocyclic groups.
[2069] The aromatic hydrocarbon cyclic groups and heterocyclic groups constituting the aforementioned multiple linking groups may be the same or different from each other; adjacent groups may be bonded to each other to form a ring, or they may not be bonded to each other.
[2070] Ar2 may bond with L2, which acts as a linking group, to form a ring, or they may not bond with each other.
[2071] L2, as a linking group, and X, adjacent to the carbon atom bonded to L2. 21 ~X 28 any carbon atom or CR 21 R 21 They may bond together to form a ring, or they may not bond together.
[2072] In equation (21) above, * indicates the bonding position with the ring shown in equation (20) above.
[2073] (Among the above phenanthroline derivatives, R) 901 R 902 R 903 R 904 R 905 R 906 R 907 R 931 R 932 R 933 R 934 R 935 R 936 and R 937 Each independently
[2074] hydrogen atom,
[2075] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2076] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2077] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2078] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2079] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[2080] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[2081] In R 903 In the case of multiple Rs, multiple Rs 903They are the same or different.
[2082] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
[2083] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.
[2084] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.
[2085] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.
[2086] In R 931 In the case of multiple Rs, multiple Rs 931 They are the same or different.
[2087] In R 932 In the case of multiple Rs, multiple Rs 932 They are the same or different.
[2088] In R 933 In the case of multiple Rs, multiple Rs 933 They are the same or different.
[2089] In R 934 In the case of multiple Rs, multiple Rs 934 They are the same or different.
[2090] In R 935 In the case of multiple Rs, multiple Rs 935 They are the same or different.
[2091] In R 936 In the case of multiple Rs, multiple Rs 936 They are the same or different.
[2092] In R 937 In the case of multiple Rs, multiple Rs 937 (They may be the same or different.)
[2093] In this specification, -O-(R 904 The group shown in R 904 In the case of hydrogen atoms, it is a hydroxyl group.
[2094] In this specification, -S-(R 905 The group shown in R 905 In the case of hydrogen atoms, it is a thiol group.
[2095] In this specification, -S(=O)2R 933 The groups shown are in R 933 In the case of a substituent, it is a substituted sulfonyl group.
[2096] In this specification, -B(R) 934 (R) 935 The group shown in R 934 and R 935 In the case of a substituent, it is a substituted methylborane.
[2097] In this specification, -P(=O)(R 936 (R) 937 The group shown in R 936 and R 937 In the case of a substituent, it is a substituted phosphine oxide group, in R 936 and R 937 In the case of an aryl group, it is an aryl phosphoroyl group.
[2098] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted linear, branched, or cyclic polyvalent aliphatic hydrocarbon group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.
[2099] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic group of the "unsubstituted polyvalent aromatic hydrocarbon group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.
[2100] Unless otherwise stated in this specification, the number of cyclic atoms in the "unsubstituted polyvalent heterocyclic group" is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.
[2101] As a heterocyclic group with 5 to 50 cyclic atoms in Ar2 of the above formula (21), it is preferred to include substituted or unsubstituted groups derived from the ring structure shown in the above formula (20).
[2102] Preferably, X in equation (20) above is... 21 and X 28 The carbon atom is bonded to the group shown in formula (21) above.
[2103] Preferably, X in equation (20) above is... 21 and X 28 One of them is a carbon atom bonded to the group shown in formula (21) above, X 21 and X 28 The other side is a carbon atom bonded to a hydrogen atom.
[2104] Preferably, X in the above formula (20) 21 ~X 28 Each independently for CR 21 Or carbon atoms bonded to the group shown in formula (21) above.
[2105] Preferably, X in the above formula (20) 21 ~X 28 Except for the carbon atoms bonded to the groups shown in formula (21) above, all other carbon atoms are CR. 21 That is, preferably, the compound represented by the above formula (20) is a 1,10-phenanthroline derivative.
[2106] Preferably, Ar2 in the above formula (21) is a substituted or unsubstituted fused aromatic hydrocarbon group with 8 to 20 cyclic carbons.
[2107] Preferably, the fused aromatic hydrocarbon group having 8 to 20 carbon atoms is, for example, a group derived from any aromatic hydrocarbon selected from naphthalene, anthracene, benzo[e]acenaphthene, acethracene, benzo[e]anthracene, triphenylene, pyrene, β-triphenylene, fluorene, phenanthrene, fluoranthene and benzo[e]fluoranthene.
[2108] Preferably, Ar2 in the above formula (21) is a substituted or unsubstituted anthracene group.
[2109] Preferably, Ar2 in the above formula (21) is a substituted or unsubstituted heterocyclic group with 5 to 40 cyclic carbons.
[2110] Preferably, Ar2 in formula (21) is a substituted or unsubstituted group derived from the ring structure shown in formula (20).
[2111] (Specific examples of phenanthrene-coral derivatives)
[2112] Specific examples of phenanthrene-rhein derivatives include the following compounds. However, the present invention is not limited to these specific examples of phenanthrene-rhein derivatives.
[2113]
[2114] (Electron injection layer)
[2115] The electron injection layer is a layer containing a material with high electron-injection properties. Alkali metals, alkaline earth metals, rare earth metals, or their compounds, such as lithium (Li), cesium (Cs), calcium (Ca), ytterbium (Yb), erbium (Er), lithium 8-(hydroxyquinoline) (Liq), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx), can be used in the electron injection layer. Alternatively, materials containing alkali metals, alkaline earth metals, rare earth metals, or their compounds can be used; specifically, materials containing magnesium (Mg) in Alq can be used. It should be noted that this allows for more efficient electron injection from the cathode.
[2116] Alternatively, a composite material consisting of an organic compound and an electron donor can be used in the electron injection layer. Such a composite material exhibits excellent electron injection and electron transport properties because it generates electrons in the organic compound through the electron donor. In this case, the organic compound is preferably a material with excellent electron transport properties; specifically, materials mentioned in the description of the electron transport region material or electron transport layer can be used. The electron donor can be any substance that exhibits electron-donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Additionally, alkali metal oxides and alkaline earth metal oxides are preferred, such as lithium oxide, calcium oxide, and barium oxide. Furthermore, Lewis bases such as magnesium oxide can also be used. Additionally, organic compounds such as tetrathiofulvalene (TTF) can also be used.
[2117] <Other components of organic EL display elements>
[2118] The structure of the organic EL element involved in this embodiment will be further explained.
[2119] (Substrate)
[2120] The substrate is used as a support for organic electroluminescent (EL) devices. Examples of substrates that can be used include glass, quartz, and plastic. Flexible substrates can also be used. A flexible substrate is a substrate that can be bent (flexible). Examples of flexible substrates include plastic substrates. Materials used to form plastic substrates include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Inorganic vapor-deposited films can also be used.
[2121] (anode)
[2122] In the organic EL element described in this embodiment, the anode is preferably made of a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically 4.0 eV or higher). Specifically, examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. Furthermore, examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metallic materials (e.g., titanium nitride).
[2123] These materials are typically formed by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1% to 10% zinc oxide relative to indium oxide. Alternatively, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5% to 5% tungsten oxide and 0.1% to 1% zinc oxide relative to indium oxide. Furthermore, these materials can also be fabricated using vacuum evaporation, coating, inkjet printing, spin coating, and other similar methods.
[2124] In the layers formed on the anode, such as the layers formed in contact with the anode, since the composite material that is easy to inject holes with is independent of the work function of the anode is used, materials that can be used as electrode materials (e.g., metals, alloys, conductive compounds and mixtures thereof, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.
[2125] Elements belonging to Group 1 or Group 2 of the periodic table that have low work functions can also be used, namely alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them. It should be noted that when using alkali metals, alkaline earth metals, and their alloys to form the anode, vacuum evaporation or sputtering methods can be used. Furthermore, when using silver paste, coating or inkjet printing methods can be used.
[2126] When the organic EL element is a bottom-emitting type, the anode is a light-transmitting electrode. The light-transmitting electrode is preferably formed of a light-transmitting or semi-light-transmitting metallic material that transmits light emitted from the light-emitting layer. In this specification, light transmittance or semi-light transmittance refers to 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-light-transmitting metallic material can be appropriately selected from the materials listed in the section on anodes. The light-transmitting or semi-light-transmitting metallic material can also be one of the materials listed later as materials for a conductive layer (or transparent conductive layer).
[2127] In the case of a top-emitting organic EL element, the anode is a light-reflective electrode with a light-reflective layer. The light-reflective layer is preferably formed of a light-reflective metallic material. In this specification, light reflectivity refers to the property of reflecting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The light-reflective metallic material can be appropriately selected from the materials listed in the section on the anode.
[2128] Examples of metallic materials used for light-reflecting layers include: elemental materials selected from any one of the metals Al, Ag, Ta, Zn, Mo, W, Ni, and Cr, or alloy materials with any one of these metals as the main component (preferably 50% by mass or more of the total); amorphous alloys selected from NiP, NiB, CrP, and CrB; microcrystalline alloys selected from NiAl and silver alloys; and so on.
[2129] In addition, as the metal material used for the light reflective layer, an alloy selected from at least one 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) can be used.
[2130] The light-reflecting layer can be a single layer or multiple layers.
[2131] The anode, serving as a light-reflective electrode, can consist of only a light-reflective layer, or it can be a multilayer structure having a light-reflective layer and a conductive layer (preferably a transparent conductive layer). When the anode is a multilayer structure with a light-reflective layer and a conductive layer, it is preferable to place the conductive layer between the reflective layer and the layer included in the hole transport region (e.g., a hole injection layer or a first hole transport layer). Alternatively, the anode can be a multilayer structure with a light-reflective layer disposed between two conductive layers (a first conductive layer and a second conductive layer). In such a multilayer structure, the first and second conductive layers can be formed of the same material or of different materials. In this specification, these multilayer structures are sometimes referred to as conductive material layers.
[2132] The material used for the conductive layer can be appropriately selected from the materials listed in the section on anodes. Alternatively, the conductive layer (transparent conductive layer) as the transparent electrode can also be made of metals, alloys, conductive compounds, and mixtures thereof with a high work function (specifically 4.0 eV or higher).
[2133] Alternatively, the conductive layer may also use 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 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 of rare earth metals.
[2134] (cathode)
[2135] In the organic EL element of this embodiment, the cathode preferably uses metals, alloys, conductive compounds, and mixtures thereof with a low work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them.
[2136] It should be noted that when using alkali metals, alkaline earth metals, or alloys containing them to form the cathode, vacuum evaporation or sputtering methods can be used. Additionally, when using silver paste, coating or inkjet printing methods can be used.
[2137] It should be noted that by setting an electron injection layer, a wide variety of conductive materials, such as Al, Ag, ITO, graphene, and indium tin oxide containing silicon or silicon oxide, can be used to form cathodes regardless of the work function. These conductive materials can be deposited using methods such as sputtering, inkjet printing, and spin coating.
[2138] When the organic EL element is a bottom-emitting type, the cathode is a light-reflective electrode. The light-reflective electrode is preferably formed of a light-reflective metallic material. The light-reflective metallic material can also be appropriately selected from the materials listed in the section on cathodes. Alternatively, the light-reflective metallic material can also be one of the materials listed above as a metallic material for a light-reflective layer.
[2139] When the organic EL element is a top-emitting type, the cathode is a light-transmitting electrode. The light-transmitting electrode is preferably formed of a light-transmitting or semi-light-transmitting metallic material that transmits light emitted from the light-emitting layer. Light transmittance or semi-light transmittance refers to 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-light-transmitting metallic material can also be appropriately selected from the materials listed in the section on cathodes described above. The light-transmitting or semi-light-transmitting metallic material can also be one of the materials listed above as materials for a conductive layer (or transparent conductive layer).
[2140] (Capping Layer)
[2141] When the organic EL element is a top-emitting type, the organic EL element typically has a capping layer on top of the cathode. The capping layer may contain a compound selected from at least one of polymeric compounds, metal oxides, metal fluorides, metal borides, silicon nitrides, and silicon compounds (such as silicon oxides). Alternatively, the capping layer may contain a compound selected from at least one of aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, or dibenzofuran derivatives. Furthermore, a laminate containing layers of these substances can also be used as the capping layer.
[2142] The organic EL element involved in this embodiment can be a bottom-emitting organic EL element. Alternatively, the organic EL element involved in this embodiment can be a top-emitting organic EL element.
[2143] When the organic EL element is a bottom-emitting type, it is preferable that the anode is a light-transmitting electrode and the cathode is a light-reflecting electrode.
[2144] When the organic EL element is a top-emitting type, it is preferable that the anode is a light-reflective electrode with light reflectivity and the cathode is a light-transmitting electrode with light transmittance.
[2145] (film thickness)
[2146] In this embodiment, the film thickness of each layer in the organic EL element is not limited except as specifically mentioned above. Generally speaking, if the film thickness is too thin, defects such as pinholes are easily generated; if the film thickness is too thick, a high applied voltage is required, resulting in decreased efficiency. Therefore, the film thickness of each organic compound layer in the organic EL element is preferably in the range of several nm to 1 μm.
[2147] (Layer Formation Method)
[2148] In this embodiment, the method for forming each layer of the organic EL element is not limited except as specifically mentioned above. Each layer of the organic EL element can be formed independently using known methods such as dry deposition and wet deposition. Examples of dry deposition methods include vacuum evaporation, sputtering, plasma deposition, and ion plating. Examples of wet deposition methods include spin coating, dip coating, flow coating, and inkjet coating.
[2149] (The general structure of an organic EL device)
[2150] Figure 1 The diagram shows the general structure of the organic EL element involved in this embodiment.
[2151] Figure 1 The organic EL element 1 shown has a substrate 2, an anode 3, a cathode 4, a first light-emitting unit 10, a second light-emitting unit 20, and a first charge-generating region 8.
[2152] The first light-emitting unit 10 is disposed between the anode 3 and the cathode 4. The first light-emitting unit 10 includes a first hole transport region 61, a first light-emitting region 51, and a first electron transport region 71. In the first light-emitting unit 10, the first hole transport region 61, the first light-emitting region 51, and the first electron transport region 71 are stacked sequentially from the anode 3 side toward the cathode 4 side.
[2153] The first hole transport region 61 includes a first hole injection layer 611, a first hole transport layer 612, and a first electron blocking layer 613. In the first hole transport region 61, the first hole injection layer 611, the first hole transport layer 612, and the first electron blocking layer 613 are stacked sequentially from the anode 3 side toward the cathode 4 side.
[2154] The first light-emitting region 51 includes a first light-emitting layer 511 and a second light-emitting layer 512. In the first light-emitting region 51, the first light-emitting layer 511 and the second light-emitting layer 512 are stacked sequentially from the anode 3 side toward the cathode 4 side.
[2155] The first electron transport region 71 includes a first hole blocking layer 711.
[2156] The second light-emitting unit 20 is disposed between the first light-emitting unit 10 and the cathode 4. The second light-emitting unit 20 includes a second hole transport region 62, a second light-emitting region 52, and a second electron transport region 72. In the second light-emitting unit 20, the second hole transport region 62, the second light-emitting region 52, and the second electron transport region 72 are stacked sequentially from the anode 3 side toward the cathode 4 side.
[2157] The second hole transport region 62 includes a second hole transport layer 621 and a second electron blocking layer 622. In the second hole transport region 62, the second hole transport layer 621 and the second electron blocking layer 622 are stacked sequentially from the anode 3 side toward the cathode 4 side.
[2158] The second light-emitting region 52 includes a third light-emitting layer 521 and a fourth light-emitting layer 522. In the second light-emitting region 52, the third light-emitting layer 521 and the fourth light-emitting layer 522 are stacked sequentially from the anode 3 side toward the cathode 4 side.
[2159] The second electron transport region 72 includes a second hole blocking layer 721, a second electron transport layer 722, and a second electron injection layer 723. In the second electron transport region 72, the second hole blocking layer 721, the second electron transport layer 722, and the second electron injection layer 723 are stacked sequentially from the anode 3 side toward the cathode 4 side.
[2160] The first charge generation region 8 is disposed between the first light-emitting unit 10 and the second light-emitting unit 20. The first charge generation region 8 includes a first charge generation layer 81 and a second charge generation layer 82. In the first charge generation region 8, the first charge generation layer 81 and the second charge generation layer 82 are sequentially stacked from the anode side 3 toward the cathode side.
[2161] This invention is not limited to Figure 1 The diagram shows the structure of an organic EL element. As another configuration of the organic EL element, the number of light-emitting units disposed between the anode and cathode can be three or more. Furthermore, in the case of a top-emitting type organic EL element, a capping layer can be stacked on top of the cathode. Additionally, the anode can be a multilayer structure as described above, for example, a reflective layer and a conductive layer can be sequentially stacked from the substrate side.
[2162] (The color of light emitted by organic EL devices)
[2163] The organic EL element involved in this embodiment preferably emits blue light. In this specification, emitting blue light refers to light emission within the range of a maximum peak wavelength in the emission spectrum that is 430 nm or higher and 480 nm or lower. The maximum peak wavelength is the peak wavelength in the emission spectrum where the luminescence intensity reaches its maximum.
[2164] In this embodiment, it is preferred that the maximum peak wavelength of the light emitted from the organic EL element is above 430 nm and below 480 nm.
[2165] The maximum peak wavelength of the light emitted from the organic EL element was determined during driving as follows. A voltage was applied to the organic EL element such that the current density was 10 mA / cm². 2The spectrophotometer CS-2000 (manufactured by Konica Minolta Co., Ltd.) was used to measure the spectrophotometer emission intensity spectrum at this time. The peak wavelength of the emission spectrum where the luminous intensity reaches its maximum was determined and taken as the maximum peak wavelength (unit: nm).
[2166] <Determination Method>
[2167] (Triplet energy T1)
[2168] The following methods can be cited as methods for determining the triplet energy T1.
[2169] The compound to be measured will be 10 -5 mol / L or higher and 10 -4 The sample was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) at a concentration of less than mol / L to obtain a solution, which was then added to a quartz cuvette as the test sample. For this test sample, the phosphorescence spectrum was measured at a low temperature (77 K) (the vertical axis was set as phosphorescence intensity, and the horizontal axis as wavelength). The wavelength value λ at the intersection of the short-wavelength side of the phosphorescence spectrum and the rising tangent line was used as the determination of the sample. edge [nm], the energy calculated according to the following conversion formula (F1) is taken as the triplet energy T1.
[2170] Conversion formula (F1): T1[eV]=1239.85 / λ edge
[2171] The tangent for the rise on the short-wavelength side of the phosphorescence spectrum is derived as follows. Consider the tangent at each point on the spectral curve, moving from the short-wavelength side of the phosphorescence spectrum up to the shortest wavelength maximum among the spectral maxima, towards 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 reaches its maximum (i.e., the tangent at the inflection point) is taken as the tangent for the rise on the short-wavelength side of the phosphorescence spectrum.
[2172] It should be noted that the maximum point of peak intensity with less than 15% of the maximum peak intensity of the spectrum is not included in the maximum value on the shortest wavelength side mentioned above. The tangent line drawn at the point where the slope value is the maximum value closest to the maximum value on the shortest wavelength side is taken as the tangent line for the rise on the short wavelength side of the phosphorescence spectrum.
[2173] Phosphorescence can be measured using the main body of the F-4500 spectrophotometer manufactured by Hitachi High Tech Co., Ltd. It should be noted that the measuring apparatus is not limited to this; measurements can be performed by combining a cooling device, a cryogenic container, an excitation source, and a light-receiving device.
[2174] (Singlet energy S1)
[2175] The following methods can be cited as methods for determining the singlet energy S1 using solutions (sometimes called the solution method).
[2176] 10 compounds were prepared as the test targets. -5 mol / L or higher and 10 -4 A toluene solution with a concentration below mol / L was added to a quartz cuvette as the test sample. The absorption spectrum of the sample was measured at room temperature (300K) (the vertical axis is set as absorption intensity, and the horizontal axis is set as wavelength). For the downward tangent on the longer wavelength side of the absorption spectrum, the wavelength value λedge [nm] at the intersection of the tangent and the horizontal axis was substituted into the conversion formula (F2) shown later to calculate the singlet energy.
[2177] Conversion formula (F2): S1[eV]=1239.85 / λedge
[2178] As an absorption spectroscopy measuring device, examples include, but are not limited to, the Hitachi spectrophotometer (device name: U3310).
[2179] The tangent for the downward sag on the longer wavelength side of the absorption spectrum is derived as follows. Consider the tangent at various points on the spectral curve as the longest wavelength maximum is moved along the longer wavelength direction. This tangent exhibits a repeated pattern of decreasing and then increasing slope as the curve declines (i.e., as the value on the vertical axis decreases). The tangent drawn at the point where the slope is minimized on the longest wavelength side (excluding cases where absorbance is below 0.1) is taken as the tangent for the downward sag on the longer wavelength side of the absorption spectrum.
[2180] It should be noted that the maximum absorbance values below 0.2 are not included in the maximum values on the longest wavelength side mentioned above.
[2181] (The maximum peak wavelength of the compound)
[2182] The method for determining the maximum peak wavelength of a compound is described below. Prepare 10 [units of something] of the compound to be measured. - 6 mol / L or higher and 10 -5A toluene solution with a concentration of less than mol / L was added to a quartz cuvette, and the emission spectrum of the sample was measured at room temperature (300K) (the vertical axis is set as emission intensity, and the horizontal axis is set as wavelength). The emission spectrum can be measured using a spectrophotometer (device name: F-7000) manufactured by Hitachi Advanced Scientific Corporation. It should be noted that the apparatus used for measuring the emission spectrum is not limited to the one used here. In the emission spectrum, the peak wavelength at which the emission intensity reaches its maximum is defined as the maximum emission peak wavelength. It should be noted that in this specification, the maximum peak wavelength of fluorescence emission is sometimes referred to as the maximum fluorescence emission peak wavelength (FL-peak).
[2183] [Second Implementation]
[2184] (Electronic devices)
[2185] The electronic device according to this embodiment incorporates the organic EL element described in any of the above embodiments. Examples of electronic devices include display devices and light-emitting devices. Examples of display devices include display components (e.g., organic EL panel modules), televisions, mobile phones, smartphones, tablet computers, and personal computers. Examples of light-emitting devices include lighting and vehicle lamps. The light-emitting device can also be used in display devices, for example, as a backlight for a display device.
[2186] In one embodiment of the electronic device, the display device and the light-emitting device are equipped with the organic EL element of the above embodiment. In another embodiment of the electronic device, the display device and the light-emitting device preferably have the organic EL element and the color conversion layer of the above embodiment. The display device and the light-emitting device preferably have a color filter. The color conversion layer is preferably located between the organic EL element and the color filter. The color conversion layer preferably contains a material that absorbs light and emits light, and the material that absorbs light and emits light is preferably a quantum dot. In the light-emitting device, the color conversion layer is preferably arranged such that light emitted from the organic EL element irradiates the color conversion layer.
[2187] [Variations on the implementation method]
[2188] It should be noted that the present invention is not limited to the embodiments described above. Modifications and improvements made within the scope of achieving the objectives of the present invention are included in the present invention.
[2189] The first and second light-emitting regions of an organic EL element contain not only two light-emitting layers, but can each contain three or more layers independently.
[2190] When an organic EL device includes additional light-emitting regions in addition to the first and second light-emitting regions, the light-emitting layers contained in these additional light-emitting regions are not limited to one or two layers, but may also consist of three or more layers. The multiple light-emitting layers contained in each light-emitting region can be of the same or different light-emitting types. Each light-emitting layer can be a fluorescent light-emitting layer or a phosphorescent light-emitting layer utilizing light emission based on electron transitions from a triplet excited state to the ground state.
[2191] Furthermore, the specific structure and shape in the implementation of the present invention may be configured as other structures within the scope of achieving the purpose of the present invention.
[2192] Example
[2193] The present invention will be further described in detail below with reference to specific embodiments. The present invention is not limited to these embodiments in any way.
[2194] <Compound>
[2195] The following shows the structures of the compounds used as the first or third host materials in the manufacture of the organic EL elements involved in Examples 1-11 and Comparative Examples 1-4.
[2196]
[2197]
[2198]
[2199]
[2200] The following shows the structures of the compounds used as the second or fourth host materials in the manufacture of the organic EL elements involved in Examples 1-11 and Comparative Examples 1-4.
[2201]
[2202]
[2203]
[2204]
[2205] The following shows the structures of other compounds used in the manufacture of the organic EL elements involved in Examples 1-11 and Comparative Examples 1-4.
[2206]
[2207]
[2208]
[2209]
[2210]
[2211] [Fabrication of Organic EL Components (1)]
[2212] <Example 1>
[2213] A glass substrate (manufactured by Geomatec Corporation) with an ITO (Indium Tin Oxide) transparent electrode (anode) and a thickness of 25mm × 75mm × 1.1mm was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO transparent electrode film thickness was 130nm.
[2214] (First light-emitting unit)
[2215] • First hole transport region
[2216] Next, compound HT1, serving as the hole transport region material, and compound HA, serving as the acceptor material, were co-deposited on the anode using vacuum evaporation to form a first hole injection layer with a thickness of 10 nm. The content of compound HT1 in the first hole injection layer was set to 97% by mass, and the content of compound HA was set to 3% by mass.
[2217] Next, compound HT1 was deposited on the first hole injection layer to form a first hole transport layer with a thickness of 80 nm.
[2218] Next, compound HT2 was deposited on the first hole transport layer to form a first electron blocking layer with a thickness of 10 nm.
[2219] As described above, in the first-stage light-emitting unit (first light-emitting unit), a first hole transport region comprising a first hole injection layer, a first hole transport layer and a first electron blocking layer is formed.
[2220] • First luminous area
[2221] Next, compound BH1-1, serving as the first host material, and compound BD1, serving as the first luminescent compound, were co-deposited on the first electron blocking layer to form a first luminescent layer with a thickness of 5 nm. The content of compound BH1-1 in the first luminescent layer was set to 98% by mass, and the content of compound BD1 was set to 2% by mass.
[2222] Next, compound BH2-1, serving as the second host material, and compound BD1, serving as the second luminescent compound, were co-deposited on the first luminescent layer to form a second luminescent layer with a thickness of 20 nm. The content of compound BH2-1 in the second luminescent layer was set to 98% by mass, and the content of compound BD1 was set to 2% by mass.
[2223] As described above, a first light-emitting region comprising a first light-emitting layer and a second light-emitting layer is formed in the first light-emitting unit.
[2224] • First electron transport region
[2225] Next, compound ET1 is deposited on the second light-emitting layer to form a first hole-blocking layer with a thickness of 10 nm. As described above, a first electron transport region containing the first hole-blocking layer is formed in the first light-emitting unit.
[2226] (Region where the first charge is generated)
[2227] Next, compound ET2, serving as the electron transport region material, and lithium were co-deposited on the first hole-blocking layer to form a first charge-generating layer with a thickness of 20 nm. The content of compound ET2 in the first charge-generating layer was set to 97% by mass, and the content of lithium was set to 3% by mass.
[2228] Next, compound HT3, serving as the hole transport region material, and compound HA, serving as the acceptor material, were co-deposited on the first charge generation layer to form a second charge generation layer with a thickness of 10 nm. The content of compound HT3 in the second charge generation layer was set to 90% by mass, and the content of compound HA was set to 10% by mass.
[2229] As described above, a first charge generation region comprising a first charge generation layer and a second charge generation layer is formed between the first light-emitting unit and the second light-emitting unit.
[2230] (Second light-emitting unit)
[2231] • Second hole transport region
[2232] Next, compound HT3, which serves as the hole transport region material, was deposited on the second charge generation layer to form a second hole transport layer with a thickness of 80 nm.
[2233] Next, compound HT2, which serves as the hole transport region material, was deposited on the second hole transport layer to form a second electron blocking layer with a thickness of 10 nm.
[2234] As described above, in the second-level light-emitting unit (second light-emitting unit), a second hole transport region comprising a second hole transport layer and a second electron blocking layer is formed.
[2235] ·Second luminous area
[2236] Next, compound BH1-2, serving as the third host material, and compound BD1, serving as the third luminescent compound, were co-deposited on the second electron blocking layer to form a third luminescent layer with a thickness of 5 nm. The content of compound BH1-2 in the third luminescent layer was set to 98% by mass, and the content of compound BD1 was set to 2% by mass.
[2237] Next, compound BH2-1, serving as the fourth host material, and compound BD1, serving as the fourth luminescent compound, were co-deposited on the third luminescent layer to form a fourth luminescent layer with a film thickness of 20 nm. The content of compound BH2-1 in the fourth luminescent layer was set to 98% by mass, and the content of compound BD1 was set to 2% by mass.
[2238] As described above, a second light-emitting region comprising a third light-emitting layer and a fourth light-emitting layer is formed in the second light-emitting unit.
[2239] • Second electron transport region
[2240] Next, compound ET1 was deposited on the fourth luminescent layer to form a second hole-blocking layer with a thickness of 10 nm.
[2241] Next, compound ET3 was deposited on top of the second hole blocking layer to form a second electron transport layer with a thickness of 20 nm.
[2242] Next, LiF was deposited on the second electron transport layer to form a second electron injection layer with a thickness of 1 nm.
[2243] As described above, a second electron transport region comprising a second hole blocking layer, a second electron transport layer and a second electron injection layer is formed in the second light-emitting unit.
[2244] Then, metallic Al was deposited on the second electron injection layer to form a cathode with a film thickness of 80 nm.
[2245] Following the above method, the bottom-emitting organic EL element described in Example 1 was fabricated.
[2246] The component configuration of the organic EL element involved in Example 1 is represented in abbreviation as follows.
[2247] ITO (130) / HT1: HA (10, 97%: 3%) / HT1 (80) / HT2 (10) / BH1-1: BD1 (5, 98%: 2%) / BH2-1: BD1 (20, 98%: 2%) / ET1 (10) / ET2: Li (20, 97%: 3 %) / HT3: HA (10, 90%: 10%) / HT3 (80) / HT2 (10) / BH1-2: BD1 (5, 98%: 2%) / BH2-1: BD1 (20, 98%: 2%) / ET1 (10) / ET3 (20) / LiF (1) / Al (80)
[2248] It should be noted that in the abbreviated component configurations described above, the numbers within parentheses represent film thickness (unit: nm). Similarly, the percentage numbers within parentheses represent the content of the corresponding components in the corresponding layers (unit: mass %). For example, the percentage number (97%: 3%) represents the content of HT1 and HA in the first hole injection layer (unit: mass %), the percentage number (98%: 2%) represents the content of the host material and luminescent compound in the first, second, third, or fourth luminescent layers (unit: mass %), the percentage number (97%: 3%) represents the content of ET2 and Li in the first charge generation layer (unit: mass %), and the percentage number (90%: 10%) represents the content of HT3 and HA in the second charge generation layer (unit: mass %). The same applies to the following embodiments and comparative examples.
[2249] <Example 2>
[2250] The organic EL element of Example 2 was manufactured in the same manner as the organic EL element of Example 1, except that the second and fourth main materials in the organic EL element of Example 1 were changed from compound BH2-1 to compound BH2-2 as described in Table 1.
[2251] <Example 3>
[2252] The organic EL element of Example 3 was manufactured in the same manner as the organic EL element of Example 1, except that the first host material in the organic EL element of Example 1 was changed from compound BH1-1 to compound BH1-3 as shown in Table 1, and the third host material was changed from compound BH1-2 to compound BH1-4 as shown in Table 1.
[2253] <Example 4>
[2254] The organic EL element of Example 4 was manufactured in the same manner as the organic EL element of Example 1, except that the first host material in the organic EL element of Example 1 was changed from compound BH1-1 to compound BH1-B as shown in Table 1, and the third host material was changed from compound BH1-2 to compound BH1-4 as shown in Table 1.
[2255] <Example 5>
[2256] The organic EL element of Example 5 was manufactured in the same manner as the organic EL element of Example 1, except that the first host material was changed from compound BH1-1 to compound BH1-2 as shown in Table 1, the second host material was changed from compound BH2-1 to compound BH2-2 as shown in Table 1, the third host material was changed from compound BH1-2 to compound BH1-1 as shown in Table 1, and the fourth host material was changed from compound BH2-1 to compound BH2-2 as shown in Table 1.
[2257] <Comparative Example 1>
[2258] The organic EL element of Comparative Example 1 was manufactured in the same manner as the organic EL element of Example 1, except that the first host material was changed from compound BH1-1 to compound BH1-A as shown in Table 1, and the third host material was changed from compound BH1-2 to compound BH1-A as shown in Tab...
Claims
1. An organic electroluminescent element, wherein, The organic electroluminescent element has an anode, a cathode, and two or more light-emitting units disposed between the anode and the cathode. The two or more light-emitting units include at least a first light-emitting unit having a first light-emitting region and a second light-emitting unit having a second light-emitting region. The anode, the first light-emitting unit, the second light-emitting unit, and the cathode are arranged sequentially from the anode side toward the cathode side. The first luminescent region includes a first luminescent layer containing a first host material and a second luminescent layer containing a second host material. The first light-emitting layer is positioned closer to the anode side than the second light-emitting layer. The second luminescent region includes a third luminescent layer containing a third host material and a fourth luminescent layer containing a fourth host material. The third light-emitting layer is positioned closer to the anode side than the fourth light-emitting layer. The first, second, third, and fourth luminescent layers each independently contain a luminescent compound exhibiting a maximum peak wavelength of less than 500 nm. The first main material and the third main material are different from each other. The first main material is different from the second and fourth main materials. The third main material is different from the second and fourth main materials. The second main material may be the same as or different from the fourth main material. The triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material satisfy the following mathematical expression (Mathematical Expression 1). The triplet energy T1(H3) of the third host material and the triplet energy T1(H4) of the fourth host material satisfy the following mathematical expression (Mathematical Expression 2). T1(H1)>T1(H2) …(Mathematical Expression 1) T1(H3)>T1(H4) …(Mathematical expression 2).
2. The organic electroluminescent element according to claim 1, wherein, The second main material is the same as the fourth main material.
3. The organic electroluminescent element according to claim 1, wherein, The second main material is different from the fourth main material.
4. The organic electroluminescent element according to any one of claims 1 to 3, wherein, The second and fourth host materials are each independently compounds represented by the following formula (2). In the above formula (2), R 201 ~R 208 each independently is hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. L 201 and L 202 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 201 and Ar 202 Each independently Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the second and fourth main materials, R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different. In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different. In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different. In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different. In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different. In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different. In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different. In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different. In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
5. The organic electroluminescent element according to any one of claims 1 to 4, wherein, One or both of the second and fourth host materials are compounds containing one or more deuterium atoms in their molecules.
6. The organic electroluminescent element according to any one of claims 1 to 5, wherein, One or both of the second and fourth host materials are compounds that do not contain deuterium atoms in their molecules.
7. The organic electroluminescent element according to any one of claims 1 to 6, wherein, One or both of the second and fourth host materials contain only carbon and hydrogen atoms in their molecules.
8. The organic electroluminescent element according to any one of claims 1 to 7, wherein, One or both of the second and fourth host materials contain carbon atoms, hydrogen atoms, and heteroatoms in their molecules.
9. The organic electroluminescent element according to any one of claims 1 to 8, wherein, One or both of the second and fourth light-emitting layers also contain a common host material. The common host material contained in the second light-emitting layer may be the same as or different from the common host material contained in the fourth light-emitting layer. The second host material is different from the co-host material contained in the second light-emitting layer and the co-host material contained in the fourth light-emitting layer. The fourth host material is different from the host material contained in the second light-emitting layer and the host material contained in the fourth light-emitting layer.
10. The organic electroluminescent element according to any one of claims 1 to 9, wherein, At least one of the first and third main materials is a compound selected from the group consisting of the compound shown in formula (H11), the compound shown in formula (H12), the compound shown in formula (H13), the compound shown in formula (H14), the compound shown in formula (H15), the compound shown in formula (H16), the compound shown in formula (H17), the compound shown in formula (H18), and the compound shown in formula (H19). In the above formula (H11), R 101 ~R 110 and R 111 ~R 120 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Among them, R 101 ~R 110 One of them represents L 101 The bonding position, R 111 ~R 120 One of them represents L 101 The bonding position, L 101 for single bond, Substituted or unsubstituted arylene groups with 6 to 24 carbon atoms, or Divalent heterocyclic groups with 5–24 cyclic atoms, substituted or unsubstituted. mx is 0, 1, 2, 3, 4, or 5. In L 101 When there are more than two, more than two L 101 They are the same or different. In the above formula (H12), Xa represents oxygen atoms, sulfur atoms, and C(R) atoms. 1201 (R) 1202 ) or Si(R 1203 (R) 1204 ), R 1201 ~R 1204 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. By R 121 ~R 130 One or more groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with 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 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or The group represented by formula (H121), Among them, R 121 ~R 130 At least one of them is a group represented by the formula (H121). When multiple groups represented by formula (H121) are present, the multiple groups represented by formula (H121) may be the same as or different from each other. L 12 for single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. ma is 0, 1, 2, or 3. In L 12 When there are more than two, more than two L 12 They are the same or different. Ar 12 It is an aryl group with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted, or a heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted. In Ar 12 In the case of two or more Ar, two or more Ar 12 They are the same or different. In the formula (H121), * represents the bonding position. In the above formula (H13), By R 131 ~R 134 and R 139 ~R 140 One or more groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings, or They do not bond with each other. By R 135 ~R 138 One or more groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings, or They do not bond with each other. Ar 131 Ar 132 and R that does not form the substituted or unsubstituted monocyclic ring 131 ~R 140 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or The group represented by formula (H131), Among them, R 131 ~R 140 Ar 131 and Ar 132 At least one of them is a group represented by the formula (H131). When multiple groups represented by formula (H131) are present, the multiple groups represented by formula (H131) may be the same as or different from each other. L 13 for single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 13 for Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. mb can be 0, 1, 2, 3, 4, or 5. In L 13 When there are more than two, more than two L 13 They are the same or different. In Ar 13 In the case of two or more Ar, two or more Ar 13 They are the same or different. In formula (H131), * indicates the bonding position with the benzo[a]anthracene ring in formula (H13). In the above formula (H14), R 1A and R 1B Each independently Substituted or unsubstituted alkyl groups having 1 to 15 carbon atoms Substituted or unsubstituted aryl groups with 6 to 17 carbon atoms, or Heterocyclic groups with 5 to 17 cyclic atoms, substituted or unsubstituted. Among them, R 1A and R 1B At least one of them is a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms. By R 141 ~R 144 Groups consisting of two or more adjacent elements and those composed of R 145 ~R 148 Any group consisting of two or more adjacent elements They bond together to form substituted or unsubstituted monocyclic rings, or They bond together to form substituted or unsubstituted fused rings. In the case where a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring is formed on the ring A side, the group represented by formula (H141) is bonded to R. 142 The carbon atom in ring A that is bonded, or the carbon atom in the monocyclic ring on the A side of ring A and the carbon atom in the fused ring on the A side of ring A that is furthest from the carbon atom C1 of ring A that is bonded to the carbon atom C2 on the B side of ring A by a single bond. In the case where the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted fused ring is formed on the ring B side instead of ring A, the group represented by formula (H141) is bonded to R. 142 Bonded carbon atoms, R is not the group represented by 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 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 17 carbon atoms, or Heterocyclic groups with 5 to 17 cyclic atoms, substituted or unsubstituted. In the above formula (H141), Ar 14 It is a substituted or unsubstituted aryl group fused with four or more rings, or a substituted or unsubstituted heterocyclic group fused with four or more rings. L 14 for single bond, Substituted or unsubstituted arylene groups with 6 to 17 carbon atoms, or Divalent heterocyclic groups with 5 to 17 cyclic atoms, substituted or unsubstituted. mc is 0, 1, or 2. * indicates the bonding position of the atom forming the ring in formula (H14). Wherein, for the compound represented by formula (H14), the molecule of the compound represented by formula (H14) contains no more than three substituted or unsubstituted aryl groups with fused four or more rings and no more than three substituted or unsubstituted heterocyclic groups with fused four or more rings. In the above formula (H15), R 150 ~R 159 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or The group represented by formula (H150), Among them, R 150 ~R 159 At least one of them is a group represented by the formula (H150). When multiple groups represented by formula (H150) are present, the multiple groups represented by formula (H150) may be the same as or different from each other. L 151 for single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 151 for Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. mg is 0, 1, 2, 3, 4 or 5, In L 151 When there are more than two, more than two L 151 They are the same or different. In Ar 151 In the case of two or more Ar, two or more Ar 151 They are the same or different. In formula (H150), * indicates the bonding position with the pyrene ring in formula (H15). In the above formula (H16), By R 160 ~R 169 One or more groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with 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 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or The group represented by formula (H161), Wherein, the substituent 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 them is a group represented by the formula (H161). When multiple groups represented by formula (H161) are present, the multiple groups represented by formula (H161) may be the same as or different from each other. L 16 for single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 16 for Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. mf is 0, 1, 2, 3, 4 or 5. In L 16 When there are more than two, more than two L 16 They are the same or different. In Ar 16 In the case of two or more Ar, two or more Ar 16 They are the same or different. In formula (H161), * indicates the bonding position with the ring shown in formula (H16). In the above formula (H17), From Rb1 to Rb 14 One or more groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. Rb1 to Rb do not form the substituted or unsubstituted monocyclic rings and do not form the substituted or unsubstituted fused rings. 14 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or The group represented by formula (H171), Wherein, the substituent when the substituted or unsubstituted monocyclic ring has a substituent, the substituent when the substituted or unsubstituted fused ring has a substituent, and Rb1 to Rb 14 At least one of them is a group represented by the formula (H171). When multiple groups represented by formula (H171) are present, the multiple groups represented by formula (H171) may be the same as or different from each other. L 17 for single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 17 for Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. mg is 0, 1, 2, 3, 4 or 5, In L 17 When there are more than two, more than two L 17 They are the same or different. In Ar 17 In the case of two or more Ar, two or more Ar 17 They are the same or different. In formula (H171), * indicates the bonding position with the ring shown in formula (H17). In the above formula (H18), Re1~Re 14 Each independently hydrogen atom, Substituted or unsubstituted aryl groups with 6 to 22 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 22 cyclic atoms, or The group represented by formula (H18a), Re1~Re 14 At least one of them is a group other than a hydrogen atom. In the above formula (H18a), Le is single bond, Substituted or unsubstituted arylene groups with 6 to 22 carbon atoms, or Divalent heterocyclic groups with 5–22 cyclic atoms, substituted or unsubstituted. Are for Substituted or unsubstituted aryl groups with 6 to 22 carbon atoms, or Heterocyclic groups with 5 to 22 cyclic atoms, substituted or unsubstituted. * indicates the bonding location. In the above formula (H19), Rd1~Rd 14 Each independently hydrogen atom, Substituted or unsubstituted aryl groups with 6 to 22 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 22 cyclic atoms, or The group represented by formula (H19a), Rd1~Rd 14 At least one of them is a group other than a hydrogen atom. In the above formula (H19a), Ld is single bond, Substituted or unsubstituted arylene groups with 6 to 22 carbon atoms, or Divalent heterocyclic groups with 5–22 cyclic atoms, substituted or unsubstituted. Ard is Substituted or unsubstituted aryl groups with 6 to 22 carbon atoms, or Heterocyclic groups with 5 to 22 cyclic atoms, substituted or unsubstituted. * indicates the bonding location. In the first body material and the third body material, R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different. In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different. In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different. In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different. In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different. In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different. In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different. In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different. In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
11. The organic electroluminescent element according to claim 10, wherein, At least one of the first and third main materials is a compound selected from the group consisting of the compound represented by formula (H11), the compound represented by formula (H12), the compound represented by formula (H13), the compound represented by formula (H14), the compound represented by formula (H15), and the compound represented by formula (H16).
12. The organic electroluminescent element according to claim 10 or 11, wherein, The first and third main materials are each independently selected from the group consisting of the compound represented by formula (H11), the compound represented by formula (H12), the compound represented by formula (H13), the compound represented by formula (H14), the compound represented by formula (H15), and the compound represented by formula (H16).
13. The organic electroluminescent element according to any one of claims 10 to 12, wherein, One of the first host material and the third host material is a compound represented by formula (H11), and the other of the first host material and the third host material is a compound represented by formula (H13).
14. The organic electroluminescent element according to any one of claims 10 to 12, wherein, One of the first host material and the third host material is a compound represented by formula (H14) or formula (H15), and the other of the first host material and the third host material is a compound represented by formula (H13).
15. The organic electroluminescent element according to any one of claims 10 to 12, wherein, One of the first host material and the third host material is a compound represented by formula (H12), and the other of the first host material and the third host material is a compound represented by formula (H13).
16. The organic electroluminescent element according to any one of claims 10 to 12, wherein, The first host material and the third host material are compounds represented by formula (H13).
17. The organic electroluminescent element according to any one of claims 10 to 12, wherein, The first host material and the third host material are compounds represented by formula (H15).
18. The organic electroluminescent element according to claim 10, wherein, One of the first host material and the third host material is a compound represented by formula (H13), and the other of the first host material and the third host material is a compound represented by formula (H17).
19. The organic electroluminescent element according to any one of claims 1 to 18, wherein, One or both of the first host material and the third host material are compounds containing one or more deuterium atoms in their molecules.
20. The organic electroluminescent element according to any one of claims 1 to 19, wherein, One or both of the first host material and the third host material are compounds that do not contain deuterium atoms in their molecules.
21. The organic electroluminescent element according to any one of claims 1 to 20, wherein, At least one of the luminescent compounds contained in the first, second, third, and fourth luminescent layers is a luminescent compound exhibiting a maximum peak wavelength of 430 nm or more and 480 nm or less.
22. The organic electroluminescent element according to any one of claims 1 to 21, wherein, The first, second, third, and fourth luminescent layers contain the same luminescent compound.
23. The organic electroluminescent element according to any one of claims 1 to 22, wherein, At least one of the luminescent compounds contained in the first, second, third, and fourth luminescent layers is a fluorescent compound.
24. The organic electroluminescent element according to any one of claims 1 to 23, wherein, The luminescent compounds contained in the first, second, third, and fourth luminescent layers are all fluorescent compounds.
25. The organic electroluminescent element according to any one of claims 1 to 24, wherein, The first, second, third, and fourth light-emitting layers do not contain phosphorescent materials.
26. The organic electroluminescent element according to any one of claims 1 to 25, wherein, A first charge generation region is included between the first light-emitting unit and the second light-emitting unit. The first charge generation region includes a first charge generation layer and a second charge generation layer disposed at a position closer to the second light-emitting unit than the first charge generation layer.
27. The organic electroluminescent element according to claim 26, wherein, The first light-emitting unit includes a first hole transport region. The second light-emitting unit includes a second hole transport region. The first hole transport region is located between the anode and the first light-emitting region. The second hole transport region is located between the first charge generation region and the second light-emitting region. The first hole transport region and the second hole transport region each independently contain one or more layers. At least one of the more than one layers contained in the first hole transport region and at least one of the more than one layers contained in the second hole transport region each independently contain a monoamine compound.
28. The organic electroluminescent element according to claim 26 or 27, wherein, The first light-emitting unit includes a first electron transport region. The second light-emitting unit includes a second electron transport region. The first electron transport region is located between the first light-emitting region and the first charge-generating region. The second electron transport region is located between the second light-emitting region and the cathode. The first electron transport region and the second electron transport region each independently contain one or more layers. At least one of the more than one layers contained in the first electron transport region and at least one of the more than one layers contained in the second electron transport region each independently contain an azazine compound.
29. The organic electroluminescent element according to any one of claims 1 to 28, wherein, The thickness of the first light-emitting layer is smaller than the thickness of the second light-emitting layer. The thickness of the third light-emitting layer is less than the thickness of the fourth light-emitting layer.
30. The organic electroluminescent element according to any one of claims 1 to 29, wherein, The first light-emitting unit is the first-stage light-emitting unit that is closest to the anode. The second light-emitting unit is the second-level light-emitting unit.
31. An electronic device comprising an organic electroluminescent element according to any one of claims 1 to 30.
Citation Information
Patent Citations
Organic electroluminescent element and electronic device
WO2021162057A1