Organic electroluminescence devices, organic electroluminescence display devices, and electronic devices
By employing specific layer configurations with unique compounds and thickness ratios in anode-side organic layers, the luminous efficiency of organic electroluminescence devices is enhanced, addressing the issue of reduced light extraction efficiency.
Patent Information
- Authority / Receiving Office
- KR · KR
- Patent Type
- Patents
- Current Assignee / Owner
- IDEMITSU KOSAN CO LTD
- Filing Date
- 2022-01-13
- Publication Date
- 2026-07-21
Smart Images

Figure 112023089016979-PCT00336_ABST
Abstract
Description
Technology Field
[0001] The present invention relates to an organic electroluminescence element, an organic electroluminescence display device, and an electronic device. Background Technology
[0002] Organic electroluminescence devices (hereinafter referred to as "organic EL devices") are applied to full-color displays such as mobile phones and televisions. When voltage is applied to an organic EL device, holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. At this time, according to the statistical rule of electron spin, singlet excitons are generated at a rate of 25%, and triplet excitons are generated at a rate of 75%.
[0003] For example, in Patent Documents 1, 2, and 3, considerations have been made to improve the performance of organic EL devices. The performance of organic EL devices includes, for example, brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan. One of the challenges of organic EL devices is the reduction in light extraction efficiency. In particular, attenuation caused by reflection resulting from the difference in refractive index of adjacent layers is a major factor in reducing the light extraction efficiency of organic EL devices. To mitigate this effect, a configuration of an organic EL device having a layer made of a low refractive index material has been proposed. Prior art literature
[0004] [Patent Document 1] International Publication No. 2020 / 189316 [Patent Document 2] Japanese Patent Publication No. 2019-161218 [Patent Document 3] International Publication No. 2011 / 093056 The problem to be solved
[0005] The object of the present invention is to provide an organic electroluminescence element with improved luminous efficiency and an organic electroluminescence display device, an electronic device equipped with said organic electroluminescence element, and an electronic device equipped with said organic electroluminescence display device. means of solving the problem
[0006] According to one embodiment of the present invention, an organic electroluminescence device is provided having a cathode, an anode, a light-emitting region disposed between the cathode and the anode, a first anode-side organic layer, a second anode-side organic layer, and a third anode-side organic layer, wherein the light-emitting region comprises at least one light-emitting layer, and the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer are disposed in the order of the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer from the anode side between the anode and the light-emitting region, and the third anode-side organic layer does not contain the compound contained in the second anode-side organic layer, and the sum of the film thickness of the second anode-side organic layer and the film thickness of the third anode-side organic layer is 30 nm or more and 150 nm or less, and the ratio of the film thickness of the second anode-side organic layer to the film thickness of the third anode-side organic layer satisfies the relationship of the following formula (A1).
[0007] 0.50 < TL3 / TL2 < 4.0 … (Mathematical Formula A1)
[0008] (TL2 is the film thickness of the second anode-side organic layer, TL3 is the film thickness of the third anode-side organic layer, and the unit of film thickness is nm.)
[0009] According to one embodiment of the present invention, the apparatus comprises a cathode, an anode, a light-emitting region disposed between the cathode and the anode, a first anode-side organic layer, a second anode-side organic layer, and a third anode-side organic layer, wherein the light-emitting region comprises at least one light-emitting layer, and the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer are disposed between the anode and the light-emitting region in the order of the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer from the anode side, wherein the third anode-side organic layer does not contain the compound contained in the second anode-side organic layer, and the third anode-side organic layer contains a compound represented by the following general formula (C1) or a compound represented by the following general formula (C2), wherein the sum of the film thickness of the second anode-side organic layer and the film thickness of the third anode-side organic layer is 30 nm or more and 150 nm or less, and the ratio of the film thickness of the second anode-side organic layer to the film thickness of the third anode-side organic layer is An organic electroluminescence device satisfying the relationship of the following formula (mathematical formula A2) is provided.
[0010] 0.30 < TL3 / TL2 < 4.0 … (Mathematical Formula A2)
[0011] (TL2 is the film thickness of the second anode-side organic layer, TL3 is the film thickness of the third anode-side organic layer, and the unit of film thickness is nm.)
[0012] [Chemical Formula 1]
[0013]
[0014] (In the above general formula (C1),
[0015] L A1 , L A2 and L A3 each independently
[0016] single bond,
[0017] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[0018] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0019] Ar 111 , Ar 112 and Ar 113 each independently
[0020] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
[0021] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, or
[0022] -Si(R C1 )(R C2 )(R C3 ) and,
[0023] R C1 , R C2 and R C3 Each is independently a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[0024] R C1 If this plural exists, the plural R C1 They are identical or different from each other,
[0025] R C2 If there are multiple instances of R C2 are identical or different from each other,
[0026] R C3 If this plural exists, the plural R C3 They are identical or different from each other.
[0027] [Chemical Formula 2]
[0028]
[0029] (In the above general formula (C2),
[0030] L B1 , L B2 , L B3 and L B4 are, each independently
[0031] single bond, or
[0032] It is a substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, and
[0033] Ar 121 , Ar 122 , Ar 123 , Ar 124 and Ar 125 are, each independently
[0034] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0035] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[0036] (In the compound represented by the above general formula (C1) and the compound represented by the above general formula (C2), the substituent in the case of “substituted or unsubstituted” is -N(R C6 )(R C7 It is not the one indicated by ), R C6 and R C7 Each is independently a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, a substituted or unsubstituted ring-forming C6–50 aryl group, or a substituted or unsubstituted ring-forming heterocyclic group with 5–50 atoms.
[0037] According to one embodiment of the present invention, the invention comprises a cathode, an anode, a light-emitting region disposed between the cathode and the anode, and a hole transport band disposed between the anode and the light-emitting region, wherein the light-emitting region comprises at least one light-emitting layer, and the hole transport band comprises at least a second anode-side organic layer and a third anode-side organic layer, wherein the second anode-side organic layer and the third anode-side organic layer are disposed in the order of the second anode-side organic layer and the third anode-side organic layer from the anode side between the anode and the light-emitting region, and the second anode-side organic layer contains at least one compound selected from the group consisting of a compound represented by the general formula (C1) and a compound represented by the following general formula (C3), and the third anode-side organic layer contains a compound represented by the general formula (C1), provided that the second anode-side organic layer contains at least one compound different from the compound contained in the third anode-side organic layer, and the refractive index of the constituent material included in the second anode-side organic layer. An organic electroluminescence device is provided in which the difference NM2-NM3 between NM2 and the refractive index NM3 of the constituent material included in the third anode-side organic layer satisfies the relationship of the following formula (Equation N1), and the distance from the anode-side interface of the third anode-side organic layer to the anode-side interface of the light-emitting layer disposed on the anode side of the light-emitting region is 20 nm or more.
[0038] NM2 - NM3 ≥ 0.05 … (Mathematical formula N1)
[0039] [Chemical Formula 3]
[0040]
[0041] In the above general formula C3,
[0042] L C1 , L C2 , L C3 and L C4 are, each independently
[0043] single bond,
[0044] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[0045] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0046] n2 is 1, 2, 3, or 4, and
[0047] If n2 is 1, L C5 Is,
[0048] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[0049] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0050] If n2 is 2, 3, or 4, multiple L C5 are identical or different from each other,
[0051] If n2 is 2, 3, or 4, multiple L C5 Is,
[0052] They combine with each other to form a substituted or unsubstituted single ring,
[0053] They combine with each other to form substituted or unsubstituted condensed rings, or
[0054] They do not combine with each other,
[0055] L that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. C5 Is,
[0056] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[0057] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0058] Ar 131 , Ar 132 , Ar 133 and Ar 134 are, each independently
[0059] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
[0060] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, or
[0061] -Si(R C1 )(R C2 )(R C3 ) and,
[0062] R C1 , R C2 and R C3 Each is independently a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[0063] R C1 If this plural exists, the plural R C1 They are identical or different from each other,
[0064] R C2 If there are multiple instances of R C2 are identical or different from each other,
[0065] R C3 If this plural exists, the plural R C3 They are identical or different from each other,
[0066] The first amino group represented by the following general formula (C3-1) and the second amino group represented by the following general formula (C3-2) are the same group.
[0067] [Chemical Formula 4]
[0068]
[0069] (In the above general formulas (C3-1) and (C3-2), * is L respectively C5 It is the connection location with.)
[0070] (In the compound represented by the above general formula (C1) and the compound represented by the above general formula (C3), the substituent in the case of “substituted or unsubstituted” is -N(R C6 )(R C7 It is not the one indicated by ), RC6 and R C7 Each is independently a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, a substituted or unsubstituted ring-forming C6–50 aryl group, or a substituted or unsubstituted ring-forming heterocyclic group with 5–50 atoms.
[0071] According to one embodiment of the present invention, the invention comprises a cathode, an anode, a light-emitting region disposed between the cathode and the anode, and a hole transport band disposed between the anode and the light-emitting region, wherein the light-emitting region comprises at least one light-emitting layer, and the hole transport band comprises at least a first anode-side organic layer, a second anode-side organic layer, and a third anode-side organic layer, wherein the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer are disposed in the order of the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer from the anode side between the anode and the light-emitting region, and wherein the first anode-side organic layer contains a first organic material and a second organic material, wherein the first organic material and the second organic material are different from each other, and the content of the second organic material in the first anode-side organic layer is less than 50 mass%, and the second anode-side organic layer comprises a compound represented by the general formula (C1) and a compound represented by the general formula (C3). An organic electroluminescence device is provided, comprising at least one compound selected from a group of compounds, wherein a first amino group represented by the general formula (C3-1) and a second amino group represented by the general formula (C3-2) have equal or different contributions, wherein the third anode-side organic layer contains a compound represented by the general formula (C1), provided that the second anode-side organic layer contains at least one compound different from the compound contained in the third anode-side organic layer, wherein the difference NM2-NM3 between the refractive index NM2 of the constituent material included in the second anode-side organic layer and the refractive index NM3 of the constituent material included in the third anode-side organic layer satisfies the relationship of the formula (formula N1), and wherein the film thickness of the third anode-side organic layer is 20 nm or more.
[0072] According to one embodiment of the present invention, an organic electroluminescence display device comprises an anode and a cathode disposed opposite each other, a blue organic EL element as a blue pixel, a green organic EL element as a green pixel, and a red organic EL element as a red pixel, wherein the blue pixel comprises an organic electroluminescence element according to one embodiment of the present invention as the blue organic EL element, the green organic EL element has a green light-emitting region disposed between the anode and the cathode, and the red organic EL element has a red light-emitting region disposed between the anode and the cathode, and wherein the blue organic EL element has a first anode-side organic layer, a second anode-side organic layer, and a third anode-side organic layer, wherein the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer are, in the presence between the light-emitting region, the green light-emitting region, and the red light-emitting region of the blue organic EL element, respectively, and the anode, the blue organic EL element and the green organic EL An organic electroluminescence display device is provided, which is installed in common across the element and the red organic EL element, wherein the blue organic EL element does not have a first anode-side organic layer and has a second anode-side organic layer and a third anode-side organic layer, and wherein the second anode-side organic layer and the third anode-side organic layer are installed in common across the blue organic EL element, the green organic EL element and the red organic EL element between the light-emitting region, the green light-emitting region, and the red light-emitting region of the blue organic EL element and the anode, respectively.
[0073] According to one aspect of the present invention, an electronic device is provided that is equipped with an organic electroluminescence element according to one aspect of the present invention.
[0074] According to one aspect of the present invention, an electronic device is provided that is equipped with an organic electroluminescence display device according to one aspect of the present invention.
[0075] According to one aspect of the present invention, an organic electroluminescence element with improved luminous efficiency and an organic electroluminescence display device, an electronic device equipped with said organic electroluminescence element, and an electronic device equipped with said organic electroluminescence display device may be provided. Brief explanation of the drawing
[0076] FIG. 1 is a diagram showing the schematic configuration of an example of an organic electroluminescence device according to a first embodiment. FIG. 2 is a diagram showing the schematic configuration of another example of an organic electroluminescence device according to the first embodiment. FIG. 3 is a diagram showing the schematic configuration of another example of an organic electroluminescence device according to the first embodiment. FIG. 4 is a diagram showing the schematic configuration of another example of an organic electroluminescence device according to the first embodiment. FIG. 5 is a diagram showing the schematic configuration of an example of an organic electroluminescence display device according to a second embodiment. FIG. 6 is a diagram showing the schematic configuration of another example of an organic electroluminescence display device according to a second embodiment. FIG. 7 is a diagram showing the schematic configuration of another example of an organic electroluminescence display device according to a second embodiment. FIG. 8 is a diagram showing the schematic configuration of another example of an organic electroluminescence display device according to a second embodiment. Specific details for implementing the invention
[0077] [definition]
[0078] In this specification, the term hydrogen atom includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.
[0079] In this specification, in the chemical structural formula, hydrogen atoms, i.e., light hydrogen atoms, deuterium atoms, or tritium atoms are bonded to the bondable positions where symbols such as "R" or "D" representing a deuterium atom are not specified.
[0080] In this specification, the ring-forming carbon number refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., monocyclic compounds, condensed-ring compounds, crosslinked compounds, carbon-coupled compounds, and heterocyclic compounds). When the ring is substituted by a substituent, the carbons included in the substituent are not included in the ring-forming carbon number. Unless otherwise noted, the "ring-forming carbon number" described below shall be the same. For example, the benzene ring has a ring-forming carbon number of 6, the naphthalene ring has a ring-forming carbon number of 10, the pyridine ring has a ring-forming carbon number of 5, and the furan ring has a ring-forming carbon number of 4. In addition, for example, the ring-forming carbon number of a 9,9-diphenylfluorenyl group is 13, and the ring-forming carbon number of a 9,9'-spirobifluorenyl group is 25.
[0081] In addition, when a benzene ring is substituted with, for example, an alkyl group, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms forming the ring of the benzene ring. Therefore, the number of carbon atoms forming the ring of the benzene ring substituted with an alkyl group is 6. In addition, when a naphthalene ring is substituted with, for example, an alkyl group, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms forming the ring of the naphthalene ring. Therefore, the number of carbon atoms forming the ring of the naphthalene ring substituted with an alkyl group is 10.
[0082] In this specification, the number of ring-forming atoms refers to the number of atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., a single ring, a condensed ring, and a ring assembly) (e.g., a single ring compound, a condensed ring compound, a crosslinked compound, a carbon ring compound, and a complex ring compound). Atoms that do not constitute a ring (e.g., a hydrogen atom terminating the bond of the atoms constituting the ring) or atoms included in the substituents when the ring is substituted by a substituent are not included in the number of ring-forming atoms. Unless otherwise noted, the "number of ring-forming atoms" described below shall be the same. For example, the number of ring-forming atoms of a pyridine ring is 6, the number of ring-forming atoms of a quinazolin ring is 10, and the number of ring-forming atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or the number of atoms constituting the substituents are not included in the number of ring-forming atoms of a pyridine ring. For this reason, the number of ring-forming atoms of a pyridine ring to which hydrogen atoms or substituents are bonded is 6. Also, for example, hydrogen atoms or atoms constituting substituents bonded to carbon atoms of a quinazoline ring are not included in the number of ring-forming atoms of the quinazoline ring. For this reason, the number of ring-forming atoms of a quinazoline ring to which hydrogen atoms or substituents are bonded is 10.
[0083] In the present specification, in the expression “substituted or unsubstituted ZZ group having XX to YY carbon atoms,” “XX to YY carbon atoms” indicates the number of carbon atoms when the ZZ group is unsubstituted and does not include the number of carbon atoms of the substituent when it is substituted. Here, “YY” is greater than “XX,” where “XX” means an integer of 1 or more, and “YY” means an integer of 2 or more.
[0084] In the present specification, the "number of atoms XX to YY" in the expression "ZZ group having XX to YY of substituted or unsubstituted atoms" represents the number of atoms when the ZZ group is unsubstituted and does not include the number of atoms of the substituent when it is substituted. Here, "YY" is greater than "XX," where "XX" means an integer greater than or equal to 1, and "YY" means an integer greater than or equal to 2.
[0085] In this specification, the term "unsubstituted ZZ group" indicates the case where the "substituted or unsubstituted ZZ group" is the "unsubstituted ZZ group," and the term "substituted ZZ group" indicates the case where the "substituted or unsubstituted ZZ group" is the "substituted ZZ group."
[0086] In this specification, when referring to a "substituted or unsubstituted ZZ group," "unsubstituted" means that the hydrogen atoms in the ZZ group are not substituted with substituents. The hydrogen atoms in the "unsubstituted ZZ group" are light hydrogen atoms, deuterium atoms, or tritium atoms.
[0087] In addition, in the present specification, "substitution" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are substituted with substituents. Likewise, "substitution" in the case of "BB group substituted with AA group" means that one or more hydrogen atoms in the BB group are substituted with AA groups.
[0088] "Substituents described in this specification"
[0089] The substituents described in this specification will be explained below.
[0090] The number of ring-forming carbons of the “unsubstituted aryl group” described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
[0091] The number of ring-forming atoms of the “unsubstituted complex ring” described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in this specification.
[0092] The number of carbon atoms of the “unsubstituted alkyl group” described in this specification is 1 to 50 unless otherwise specified in this specification, preferably 1 to 20, and more preferably 1 to 6.
[0093] The number of carbon atoms of the “unsubstituted alkenyl group” described in this specification is 2 to 50 unless otherwise specified in this specification, preferably 2 to 20, and more preferably 2 to 6.
[0094] The number of carbon atoms of the “unsubstituted alkynyl group” described in this specification is 2 to 50 unless otherwise specified in this specification, preferably 2 to 20, and more preferably 2 to 6.
[0095] The number of ring-forming carbon atoms of the “unsubstituted cycloalkyl group” described in this specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified in this specification.
[0096] The number of ring-forming carbon atoms of the “unsubstituted arylene group” described in this specification is 6 to 50 unless otherwise specified in this specification, preferably 6 to 30, and more preferably 6 to 18.
[0097] The number of ring-forming atoms of the “unsubstituted divalent complex circulator” described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in this specification.
[0098] The number of carbon atoms of the “unsubstituted alkylene group” described in this specification is 1 to 50 unless otherwise specified in this specification, preferably 1 to 20, and more preferably 1 to 6.
[0099] · "Substitution or non-substitution aryl"
[0100] Examples of specific examples (Group of Specific Examples G1) of the “substituted or unsubstituted aryl group” described in this specification include the following unsubstituted aryl group (Group of Specific Examples G1A) and substituted aryl group (Group of Specific Examples G1B). (Here, the term “unsubstituted aryl group” refers to the case where the “substituted or unsubstituted aryl group” is a “unsubstituted aryl group,” and the term “substituted aryl group” refers to the case where the “substituted or unsubstituted aryl group” is a “substituted aryl group.”). In this specification, when simply referred to as “aryl group,” it includes both the “unsubstituted aryl group” and the “substituted aryl group.”
[0101] "Substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are substituted with substituents. Examples of "substituted aryl groups" include, for instance, a group in which one or more hydrogen atoms of an "unsubstituted aryl group" of the following Specific Example Group G1A are substituted with substituents, and examples of substituted aryl groups of the following Specific Example Group G1B. Furthermore, the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed herein are merely examples, and the "substituted aryl groups" described in this specification include a group in which a hydrogen atom bonded to the carbon atom of the aryl group itself in the "substituted aryl group" of the following Specific Example Group G1B is further substituted with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted aryl group" of the following Specific Example Group G1B is further substituted with a substituent.
[0102] ·Muchwan's Arilgi (Guchaeye Group G1A):
[0103] phenyl group,
[0104] p-biphenyl group,
[0105] m-biphenyl group,
[0106] o-biphenyl group,
[0107] p-terphenyl-4-diary,
[0108] p-terphenyl-3-diary,
[0109] p-terphenyl-2-diary,
[0110] m-terphenyl-4-diary,
[0111] m-terphenyl-3-diary,
[0112] m-terphenyl-2-diary,
[0113] o-terphenyl-4-diary,
[0114] o-terphenyl-3-diary,
[0115] o-terphenyl-2-diyl,
[0116] 1-Naphthyl group,
[0117] 2-Naphthyl group,
[0118] Anthrill,
[0119] Benzoanthryl group,
[0120] phenanthril group,
[0121] Benzophenanthrile group,
[0122] Penalenyl group,
[0123] Pyreneyl group,
[0124] Crysenyl group,
[0125] benzocrysenyl group,
[0126] triphenylenyl group,
[0127] benzotriphenylenyl group,
[0128] tetracenyl group,
[0129] Pentacenyl group,
[0130] Fluorenyl group,
[0131] 9,9'-spirobifluorenyl group,
[0132] benzofluorenyl group,
[0133] dibenzofluorenyl group,
[0134] Fluoranthenyl group,
[0135] benzofluranthenyl group,
[0136] perylenyl group, and
[0137] A monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).
[0138] [Chemical Formula 5]
[0139]
[0140] [Chemical Formula 6]
[0141]
[0142] · Substitutional aryl group (Specific example group G1B):
[0143] o-tollil group,
[0144] m-tolyl group,
[0145] p-tolyl group,
[0146] Para-xyl group,
[0147] meta-xyl group,
[0148] Ortho-xyl group,
[0149] para-isopropylphenyl group,
[0150] meta-isopropylphenyl group,
[0151] Ortho-isopropylphenyl group,
[0152] para-t-butylphenyl group,
[0153] meta-t-butylphenyl group,
[0154] Ortho-t-butylphenyl group,
[0155] 3,4,5-trimethylphenyl group,
[0156] 9,9-dimethylfluorenyl group,
[0157] 9,9-diphenylfluorenyl group,
[0158] 9,9-bis(4-methylphenyl)fluorenyl group,
[0159] 9,9-bis(4-isopropylphenyl)fluorenyl group,
[0160] 9,9-bis(4-t-butylphenyl)fluorenyl group,
[0161] cyanophenyl group,
[0162] triphenylsilylphenyl group,
[0163] trimethylsilylphenyl group,
[0164] phenylnaphthyl group,
[0165] Naphthylphenyl group, and
[0166] A group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by the above general formulas (TEMP-1) to (TEMP-15) are substituted with substituents.
[0167] · "Substitutional or Non-substitutional Complex Recall"
[0168] The “complex circulating group” described in this specification is a cyclic group comprising at least one heteroatom in a ring-forming atom. Specific examples of heteroatoms include nitrogen atoms, oxygen atoms, sulfur atoms, silicon atoms, phosphorus atoms, and boron atoms.
[0169] The “complex ring” described in this specification is a simple ring or a condensed ring.
[0170] The “complex generator” described in this specification is an aromatic complex generator or a non-aromatic complex generator.
[0171] Examples of specific examples (Group of Specific Examples G2) of the “complex circulator with or without permutation” described in this specification include the following complex circulators with or without permutation (Group of Specific Examples G2A) and complex circulators with permutation (Group of Specific Examples G2B). (Here, a complex circulator with or without permutation refers to the case where the “complex circulator with or without permutation” is a “complex circulator with or without permutation,” and a complex circulator with permutation refers to the case where the “complex circulator with or without permutation” is a “complex circulator with permutation.”). In this specification, when simply referred to as a “complex circulator,” it includes both a “complex circulator with or without permutation” and a “complex circulator with permutation.”
[0172] "Substituted complex group" refers to a group in which one or more hydrogen atoms of a "non-substituted complex group" are substituted with substituents. Specific examples of a "substituted complex group" include a group in which a hydrogen atom of a "non-substituted complex group" of the following group of examples G2A is substituted, and an example of a substituted complex group of the following group of examples G2B. Furthermore, the examples of "non-substituted complex groups" and "substituted complex groups" listed herein are merely examples, and the "substituted complex group" described in this specification includes a group in which a hydrogen atom bonded to the ring-forming atom of the complex group itself in the "substituted complex group" of the following group of examples G2B is further substituted with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted complex group" of the following group of examples G2B is further substituted with a substituent.
[0173] Specific example group G2A includes, for example, an unsubstituted complex saturator containing a nitrogen atom (Specific example group G2A1), an unsubstituted complex saturator containing an oxygen atom (Specific example group G2A2), an unsubstituted complex saturator containing a sulfur atom (Specific example group G2A3), and a monovalent complex saturator (Specific example group G2A4) derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33).
[0174] The exemplary group G2B includes, for example, a substituent complex group containing a nitrogen atom (exemplary group G2B1), a substituent complex group containing an oxygen atom (exemplary group G2B2), a substituent complex group containing a sulfur atom (exemplary group G2B3), and a group in which one or more hydrogen atoms are substituted as substituents among monovalent complex groups derived from ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (exemplary group G2B4).
[0175] · Unsubstituted complex saturators containing nitrogen atoms (Specific Example Group G2A1):
[0176] pyrrolyl group,
[0177] Imidajorilgi,
[0178] pyrazolyl group,
[0179] triazolyl group,
[0180] tetrazolyl group,
[0181] Oxazoligi,
[0182] Isooxazolilgi,
[0183] Oxadiazolyl group,
[0184] Thiazolyl group,
[0185] isothiazolyl group,
[0186] Thiadiazolylgi,
[0187] Piridilgi,
[0188] Piridajinilgi,
[0189] pyrimidinyl group,
[0190] Pyrazinyl group,
[0191] triazinyl group,
[0192] Indolil,
[0193] Isoindolilgi,
[0194] Indolezinyl group,
[0195] Quinolidinyl group,
[0196] Quinolyl group,
[0197] isoquinolyl group,
[0198] Sinnolilgi,
[0199] Phthalaginyl group,
[0200] Quinazolinyl group,
[0201] Quinoxalinyl group,
[0202] benzimidazolyl group,
[0203] Indazolill,
[0204] phenanthrolinyl group,
[0205] phenanthridinyl group,
[0206] Acridinyl group,
[0207] phenazinyl group,
[0208] Carbazolyl group,
[0209] benzocarbazolyl group,
[0210] Morpolinogi,
[0211] phenoxazinyl group,
[0212] Phenothiazinyl group,
[0213] Azacarbazolyl group, and
[0214] Diazacarbazolyl group.
[0215] · Unsubstituted complex circulators containing oxygen atoms (Specific Example Group G2A2):
[0216] Purilgi,
[0217] Oxazoligi,
[0218] Isooxazolilgi,
[0219] Oxadiazolyl group,
[0220] xanthenyl group,
[0221] benzofuranyl group,
[0222] isobenzofuranyl group,
[0223] dibenzofuranyl group,
[0224] Naphthobenzofuranyl group,
[0225] Benzooxazolyl group,
[0226] Benzoisooxazolyl group,
[0227] phenoxazinyl group,
[0228] Morpolinogi,
[0229] dinaphthofranyl group,
[0230] Azadibenzofuranyl group,
[0231] Diazadibenzofuranyl group,
[0232] Azanaptobenzofuranyl group, and
[0233] Diazanaptobenzofuranyl group.
[0234] · Unsubstitutable complex circulators containing sulfur atoms (Specific Example Group G2A3):
[0235] thienyl group,
[0236] Thiazolyl group,
[0237] isothiazolyl group,
[0238] Thiadiazolylgi,
[0239] benzothiophenyl group (benzothienyl group),
[0240] isobenzothiophenyl group (isobenzothienyl group),
[0241] dibenzothiophenyl group (dibenzothienyl group),
[0242] Naphthobenzothiophenyl group (naphthobenzothienyl group),
[0243] benzothiazolyl group,
[0244] Benzoisothiazolyl group,
[0245] Phenothiazinyl group,
[0246] dinaphthothiophenyl group (dinaphthienyl group),
[0247] Azadibenzothiophenyl group (azadibenzothienyl group),
[0248] Diazadibenzothiophenyl group (diazadibenzothienyl group),
[0249] Azanapthobenzothiophenyl group (azanaphthobenzothienyl group), and
[0250] Diazanaptobenzothiophenyl group (diazanaptobenzothienyl group).
[0251] · A monovalent complex circulator induced by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (Specific Example Group G2A4):
[0252] [Chemical Formula 7]
[0253]
[0254] [Chemical Formula 8]
[0255]
[0256] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y AEach is independently an oxygen atom, a sulfur atom, NH, or CH2. However, X A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH.
[0257] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A In cases where at least one of them is NH or CH2, the monovalent complex circulating group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.
[0258] · Substitutional complex valence group containing a nitrogen atom (Specific Example Group G2B1):
[0259] (9-phenyl)carbazolyl group,
[0260] (9-biphenylyl)carbazolyl group,
[0261] (9-phenyl)phenylcarbazolyl group,
[0262] (9-naphthyl)carbazolyl group,
[0263] Diphenylcarbazole-9-diary,
[0264] Phenylcarbazole-9-diary,
[0265] methylbenzimidazolyl group,
[0266] Ethylbenzimidazolyl group,
[0267] phenyltriazinyl group,
[0268] biphenyltriazinyl group,
[0269] diphenyltriazinyl group,
[0270] Phenylquinazolinyl group, and
[0271] Biphenylquinazolinyl group.
[0272] · Substitutional complex mutators containing oxygen atoms (Specific Example Group G2B2):
[0273] Phenyldibenzofuranyl group,
[0274] methyldibenzofuranyl group,
[0275] t-butyldibenzofuranyl group, and
[0276] The monovalent residue of spiro[9H-xanthen-9,9'-[9H]fluorene].
[0277] · Complex substitution group containing sulfur atoms (Specific Example Group G2B3):
[0278] Phenyldibenzothiophenyl group,
[0279] methyldibenzothiophenyl group,
[0280] t-butyldibenzothiophenyl group, and
[0281] A monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].
[0282] · A group in which one or more hydrogen atoms of a monovalent complex cyclic group derived from the above general formulas (TEMP-16) to (TEMP-33) are substituted with substituents (Specific Example Group G2B4):
[0283] The above "one or more hydrogen atoms of a monovalent complex group" refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent complex group, X A and Y A A hydrogen atom bonded to a nitrogen atom in the case where at least one of them is NH, and X A and Y A It means one or more hydrogen atoms selected from the hydrogen atoms of the methylene group in the case where one of them is CH2.
[0284] · Substituted or unsubstituted alkyl group
[0285] Examples of specific examples (Group of Specific Examples G3) of the “substituted or unsubstituted alkyl group” described in this specification include the following unsubstituted alkyl group (Group of Specific Examples G3A) and substituted alkyl group (Group of Specific Examples G3B). (Here, the term “unsubstituted alkyl group” refers to the case where the “substituted or unsubstituted alkyl group” is an “unsubstituted alkyl group,” and the term “substituted alkyl group” refers to the case where the “substituted or unsubstituted alkyl group” is a “substituted alkyl group.”). Hereinafter, when simply referred to as “alkyl group,” both the “unsubstituted alkyl group” and the “substituted alkyl group” are included.
[0286] "Substituted alkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are substituted with substituents. Specific examples of "substituted alkyl group" include the group in which one or more hydrogen atoms in the following "unsubstituted alkyl group" (Specific Example Group G3A) are substituted with substituents, and examples of a substituted alkyl group (Specific Example Group G3B). In this specification, the alkyl group in "unsubstituted alkyl group" refers to a chain-type alkyl group. Accordingly, "unsubstituted alkyl group" includes straight-chain "unsubstituted alkyl groups" and branched "unsubstituted alkyl groups." In addition, the examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed herein are merely examples, and the "substituted alkyl groups" described in this specification include groups in which the hydrogen atom of the alkyl group itself in the "substituted alkyl group" of Specific Example Group G3B is further substituted with a substituent, and groups in which the hydrogen atom of the substituent in the "substituted alkyl group" of Specific Example Group G3B is further substituted with a substituent.
[0287] · Unsubstituted alkyl group (Specific Example Group G3A):
[0288] methyl group,
[0289] ethyl group,
[0290] n-Profilter,
[0291] isopropyl group,
[0292] n-butyl group,
[0293] isobutyl group,
[0294] s-butyl group and
[0295] t-butyl group.
[0296] · Substituted alkyl group (Specific Example Group G3B):
[0297] heptafluoropropyl group (including isomers),
[0298] pentafluoroethyl group,
[0299] 2,2,2-trifluoroethyl group, and
[0300] Trifluoromethyl group.
[0301] · "Substituted or unsubstituted alkenyl group"
[0302] Examples of specific examples (Group of Specific Examples G4) of the “substituted or unsubstituted alkenyl group” described in this specification include the following unsubstituted alkenyl group (Group of Specific Examples G4A) and substituted alkenyl group (Group of Specific Examples G4B). (Here, “unsubstituted alkenyl group” refers to the case where the “substituted or unsubstituted alkenyl group” is the “unsubstituted alkenyl group,” and “substituted alkenyl group” refers to the case where the “substituted or unsubstituted alkenyl group” is the “substituted alkenyl group.”). In this specification, when simply referred to as “alkenyl group,” it includes both the “unsubstituted alkenyl group” and the “substituted alkenyl group.”
[0303] "Substituted alkenyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are substituted with substituents. Specific examples of "substituted alkenyl groups" include the following "unsubstituted alkenyl groups" (Specific Example Group G4A) having substituents and examples of substituted alkenyl groups (Specific Example Group G4B). Furthermore, the examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed herein are merely examples, and the "substituted alkenyl groups" described in this specification include a group in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl group" of Specific Example Group G4B is further substituted with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkenyl group" of Specific Example Group G4B is further substituted with a substituent.
[0304] · Non-substituted alkenyl group (Specific Example Group G4A):
[0305] vinyl,
[0306] Alilgi,
[0307] 1-butenyl group,
[0308] 2-butenyl group, and
[0309] 3-butenyl group.
[0310] · Substitutional alkenyl group (Specific example group G4B):
[0311] 1,3-butanedienyl group,
[0312] 1-methylvinyl group,
[0313] 1-methylallyl group,
[0314] 1,1-dimethylallyl group,
[0315] 2-methylallyl group, and
[0316] 1,2-dimethylallyl group.
[0317] · "Substituted or unsubstituted alkynyl group"
[0318] Examples of specific examples (Group of Examples G5) of the “substituted or unsubstituted alkynyl group” described in this specification include the following unsubstituted alkynyl group (Group of Examples G5A). (Here, the term “unsubstituted alkynyl group” refers to the case where the “substituted or unsubstituted alkynyl group” is the “unsubstituted alkynyl group.”) Hereinafter, when simply referred to as “alkynyl group,” both the “unsubstituted alkynyl group” and the “substituted alkynyl group” are included.
[0319] "Substituted alkynyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" are substituted with substituents. Specific examples of the "substituted alkynyl group" include the group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" (Specific Example Group G5A) below are substituted with substituents.
[0320] · Unsubstituted alkynyl group (Specific example group G5A):
[0321] Ethinyl group.
[0322] · Substituted or unsubstituted cycloalkyl group
[0323] Examples of specific examples (Group of Specific Examples G6) of the “substituted or unsubstituted cycloalkyl group” described in this specification include the following unsubstituted cycloalkyl group (Group of Specific Examples G6A) and substituted cycloalkyl group (Group of Specific Examples G6B). (Here, “unsubstituted cycloalkyl group” refers to the case where the “substituted or unsubstituted cycloalkyl group” is an “unsubstituted cycloalkyl group,” and “substituted cycloalkyl group” refers to the case where the “substituted or unsubstituted cycloalkyl group” is a “substituted cycloalkyl group.”). In this specification, when simply referred to as “cycloalkyl group,” it includes both “unsubstituted cycloalkyl group” and “substituted cycloalkyl group.”
[0324] "Substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are substituted with substituents. Specific examples of "substituted cycloalkyl groups" include the group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" (Specific Example Group G6A) are substituted with substituents, and examples of "substituted cycloalkyl groups" (Specific Example Group G6B). Furthermore, the examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed herein are merely examples, and the "substituted cycloalkyl groups" described in this specification include a group in which one or more hydrogen atoms bonded to the carbon atoms of the cycloalkyl group itself in the "substituted cycloalkyl group" of Specific Example Group G6B are substituted with substituents, and a group in which the hydrogen atoms of the substituent in the "substituted cycloalkyl group" of Specific Example Group G6B are further substituted with substituents.
[0325] · Unsubstituted cycloalkyl group (Specific Example Group G6A):
[0326] cyclopropyl group,
[0327] cyclobutyl group,
[0328] Cyclopentyl group,
[0329] cyclohexyl group,
[0330] 1-adamantyl group,
[0331] 2-adamantyl group,
[0332] 1-norbornyl group, and
[0333] 2-Norbornilgi.
[0334] · Substituted cycloalkyl group (Specific Example Group G6B):
[0335] 4-methylcyclohexyl group.
[0336] ·「-Si(R 901 )(R 902 )(R 903 The device indicated by )
[0337] -Si(R as described in this specification 901 )(R 902 )(R 903As a specific example of the device indicated by ) (specific example group G7),
[0338] -Si(G1)(G1)(G1),
[0339] -Si(G1)(G2)(G2),
[0340] -Si(G1)(G1)(G2),
[0341] -Si(G2)(G2)(G2),
[0342] -Si(G3)(G3)(G3), and
[0343] -Si(G6)(G6)(G6)
[0344] ...can be cited. Here,
[0345] G1 is a “substituted or non-substituted aryl group” described in Specific Example Group G1.
[0346] G2 is a "complex circulator of permutation or non-permutation" described in specific example group G2.
[0347] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.
[0348] G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Example Group G6.
[0349] In -Si(G1)(G1)(G1), the multiple G1s are either identical or different from each other.
[0350] In -Si(G1)(G2)(G2), the multiple G2s are either identical or different from each other.
[0351] In -Si(G1)(G1)(G2), the multiple G1s are either identical or different from each other.
[0352] In -Si(G2)(G2)(G2), the multiple G2s are either identical or different from each other.
[0353] In -Si(G3)(G3)(G3), the multiple G3s are either identical or different from each other.
[0354] In -Si(G6)(G6)(G6), the multiple G6s are either identical or different from each other.
[0355] ·「-O-(R 904 The unit indicated by )
[0356] -O-(R as described in this specification 904 As a specific example of the device indicated by ) (specific example group G8),
[0357] -O(G1),
[0358] -O(G2),
[0359] -O(G3), and
[0360] -O(G6)
[0361] ...can be cited. Here,
[0362] G1 is a “substituted or non-substituted aryl group” described in Specific Example Group G1.
[0363] G2 is a "complex circulator of permutation or non-permutation" described in specific example group G2.
[0364] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.
[0365] G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Example Group G6.
[0366] ·「-S-(R 905 The unit indicated by )
[0367] -S-(R as described in this specification 905 As a specific example of the device indicated by ) (specific example group G9),
[0368] -S(G1),
[0369] -S(G2),
[0370] -S(G3), and
[0371] -S(G6)
[0372] ...can be cited. Here,
[0373] G1 is a “substituted or non-substituted aryl group” described in Specific Example Group G1.
[0374] G2 is a "complex circulator of permutation or non-permutation" described in specific example group G2.
[0375] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.
[0376] G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Example Group G6.
[0377] ·「-N(R 906 )(R 907 The unit indicated by )
[0378] -N(R as described in this specification 906 )(R 907 As a specific example of the device indicated by ) (specific example group G10),
[0379] -N(G1)(G1),
[0380] -N(G2)(G2),
[0381] -N(G1)(G2),
[0382] -N(G3)(G3), and
[0383] -N(G6)(G6)
[0384] ...can be cited. Here,
[0385] G1 is a “substituted or non-substituted aryl group” described in Specific Example Group G1.
[0386] G2 is a "complex circulator of permutation or non-permutation" described in specific example group G2.
[0387] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.
[0388] G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Example Group G6.
[0389] In -N(G1)(G1), multiple G1s are identical or different from each other.
[0390] In -N(G2)(G2), multiple G2s are identical or different from each other.
[0391] In -N(G3)(G3), multiple G3s are identical or different from each other.
[0392] In -N(G6)(G6), multiple G6s are identical or different from each other.
[0393] · Halogen atom
[0394] Examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.
[0395] · "Substituted or unsubstituted fluoroalkyl group"
[0396] The "substituted or unsubstituted fluoroalkyl group" described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is substituted with a fluorine atom, and also includes a group (perfluoro group) in which all hydrogen atoms bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" are substituted with fluorine atoms. Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of the "fluoroalkyl group" are substituted with a substituent. In addition, the “substituted fluoroalkyl group” described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the “substituted fluoroalkyl group” are further substituted with a substituent, and a group in which one or more hydrogen atoms of the substituent in the “substituted fluoroalkyl group” are further substituted with a substituent. Specific examples of the “unsubstituted fluoroalkyl group” include a group in which one or more hydrogen atoms in the “alkyl group” (specific example group G3) are substituted with a fluorine atom.
[0397] · "Substituted or unsubstituted haloalkyl group"
[0398] The "substituted or unsubstituted haloalkyl group" described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is substituted with a halogen atom, and includes a group in which all hydrogen atoms bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" are substituted with halogen atoms. Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of the "haloalkyl group" are substituted with a substituent. In addition, the “substituted haloalkyl group” described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the “substituted haloalkyl group” are further substituted with a substituent, and a group in which one or more hydrogen atoms of the substituent in the “substituted haloalkyl group” are further substituted with a substituent. Specific examples of the “unsubstituted haloalkyl group” include a group in which one or more hydrogen atoms in the “alkyl group” (Specific Example Group G3) are substituted with a halogen atom. A haloalkyl group may be referred to as an alkyl halide group.
[0399] · "Substitutional or non-substitutional alkoxyl group"
[0400] A specific example of the “substituted or unsubstituted alkoxy group” described in this specification is a group represented by -O(G3), where G3 is the “substituted or unsubstituted alkyl group” described in the group of specific examples G3. Unless otherwise specified in this specification, the number of carbon atoms of the “unsubstituted alkoxy group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.
[0401] · "Substituted or unsubstituted alkylthio groups"
[0402] A specific example of the “substituted or unsubstituted alkylthio group” described in this specification is a group represented by -S(G3), where G3 is the “substituted or unsubstituted alkyl group” described in the group of specific examples G3. Unless otherwise specified in this specification, the number of carbon atoms of the “unsubstituted alkylthio group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.
[0403] · "Substituted or unsubstituted aryloxy groups"
[0404] A specific example of the “substituted or unsubstituted aryloxy group” described in this specification is a group represented by -O(G1), where G1 is the “substituted or unsubstituted aryl group” described in the group of specific examples G1. The number of ring-forming carbons of the “unsubstituted aryloxy group” is 6 to 50 unless otherwise specified in this specification, preferably 6 to 30, and more preferably 6 to 18.
[0405] · "Substitution or non-substitution arylthioge"
[0406] A specific example of the “substituted or unsubstituted arylthio group” described in this specification is a group represented by -S(G1), where G1 is the “substituted or unsubstituted aryl group” described in the group of specific examples G1. The number of ring-forming carbons of the “unsubstituted arylthio group” is 6 to 50 unless otherwise specified in this specification, preferably 6 to 30, and more preferably 6 to 18.
[0407] · Substituted or unsubstituted trialkylsilyl group
[0408] A specific example of the “trialkylsilyl group” described in this specification is a group represented by -Si(G3)(G3)(G3), wherein G3 is a “substituted or unsubstituted alkyl group” described in the group of specific examples G3. In -Si(G3)(G3)(G3), the plurality of G3s may be identical or different from one another. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the “trialkylsilyl group” is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.
[0409] · "Substitution or non-substitution Aralkilgi"
[0410] A specific example of the “substituted or unsubstituted aralkyl group” described in this specification is a group represented by -(G3)-(G1), wherein G3 is the “substituted or unsubstituted alkyl group” described in the group of specific examples G3, and G1 is the “substituted or unsubstituted aryl group” described in the group of specific examples G1. Accordingly, the “aralkyl group” is a group in which a hydrogen atom of the “alkyl group” is substituted with an “aryl group” as a substituent, and is one embodiment of the “substituted alkyl group.” The “unsubstituted aralkyl group” is the “unsubstituted alkyl group” substituted with the “unsubstituted aryl group,” and the number of carbon atoms of the “unsubstituted aralkyl group” is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.
[0411] Specific examples of “substituted or unsubstituted aralkyl groups” include benzyl groups, 1-phenylethyl groups, 2-phenylethyl groups, 1-phenylisopropyl groups, 2-phenylisopropyl groups, phenyl-t-butyl groups, α-naphthylmethyl groups, 1-α-naphthylethyl groups, 2-α-naphthylethyl groups, 1-α-naphthylisopropyl groups, 2-α-naphthylisopropyl groups, β-naphthylmethyl groups, 1-β-naphthylethyl groups, 2-β-naphthylethyl groups, 1-β-naphthylisopropyl groups, and 2-β-naphthylisopropyl groups.
[0412] The substituted or unsubstituted aryl groups described in this specification are, unless otherwise specified in this specification, preferably phenyl groups, p-biphenyl groups, m-biphenyl groups, o-biphenyl groups, p-terphenyl-4-yl groups, p-terphenyl-3-yl groups, p-terphenyl-2-yl groups, m-terphenyl-4-yl groups, m-terphenyl-3-yl groups, m-terphenyl-2-yl groups, o-terphenyl-4-yl groups, o-terphenyl-3-yl groups, o-terphenyl-2-yl groups, 1-naphthyl groups, 2-naphthyl groups, anthryl groups, phenanthryl groups, pyrenyl groups, chrysenyl groups, triphenylenyl groups, fluorenyl groups, 9,9'-spirobifluorenyl groups, 9,9-dimethylfluorenyl groups, and 9,9-diphenylfluorenyl groups, etc.
[0413] The substituted or unsubstituted complex groups described herein, unless otherwise specified herein, are preferably pyridyl groups, pyrimidinyl groups, triazinyl groups, quinolyl groups, isoquinolyl groups, quinazolinyl groups, benzimidazolyl groups, phenanthrolinyl groups, carbazolyl groups (1-carbazolyl groups, 2-carbazolyl groups, 3-carbazolyl groups, 4-carbazolyl groups or 9-carbazolyl groups), benzocarbazolyl groups, azacarbazolyl groups, diazacarbazolyl groups, dibenzofuranyl groups, naphthobenzofuranyl groups, azadibenzofuranyl groups, diazadibenzofuranyl groups, dibenzothiophenyl groups, naphthobenzothiophenyl groups, azadibenzothiophenyl groups, diazadibenzothiophenyl groups, (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group or (9-phenyl)carbazol-4-yl group, (9-biphenyllil)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylliltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group, etc.
[0414] In this specification, the carbazolyl group is, specifically, any one of the following, unless otherwise specified in this specification.
[0415] [Chemical Formula 9]
[0416]
[0417] In this specification, the (9-phenyl)carbazolyl group is, specifically, any one of the following groups, unless otherwise specified in this specification.
[0418] [Chemical Formula 10]
[0419]
[0420] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.
[0421] In this specification, the dibenzofuranyl group and the dibenzothiophenyl group are, specifically, any one of the following groups, unless otherwise specified in this specification.
[0422] [Chemical Formula 11]
[0423]
[0424] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.
[0425] The substituted or unsubstituted alkyl groups described in this specification are, unless otherwise specified in this specification, preferably methyl groups, ethyl groups, propyl groups, isopropyl groups, n-butyl groups, isobutyl groups, and t-butyl groups, etc.
[0426] · "Substitutional or non-substitutional arylen groups"
[0427] The “substituted or unsubstituted arylene group” described in this specification is a divalent group derived by removing one hydrogen atom from the aryl ring from the “substituted or unsubstituted aryl group” unless otherwise noted. Specific examples of the “substituted or unsubstituted arylene group” (Specific Example Group G12) include a divalent group derived by removing one hydrogen atom from the aryl ring from the “substituted or unsubstituted aryl group” described in Specific Example Group G1.
[0428] · "Divination of Substitution or Non-Substitution of a Bivalent Complex Call"
[0429] The “substituted or unsubstituted divalent complex ring” described in this specification is, unless otherwise noted, a divalent ring derived by removing one hydrogen atom from the “substituted or unsubstituted complex ring”. Specific examples of the “substituted or unsubstituted divalent complex ring” (Specific Example Group G13) include a divalent ring derived by removing one hydrogen atom from the “substituted or unsubstituted complex ring” described in Specific Example Group G2.
[0430] · "Substituted or unsubstituted alkylene group"
[0431] The “substituted or unsubstituted alkylene group” described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the “substituted or unsubstituted alkyl group” unless otherwise specified. Specific examples of the “substituted or unsubstituted alkylene group” (Specific Example Group G14) include a divalent group derived by removing one hydrogen atom on the alkyl chain from the “substituted or unsubstituted alkyl group” described in Specific Example Group G3.
[0432] The substituted or unsubstituted arylene groups described in this specification are, unless otherwise specified in this specification, preferably any one of the following general formulas (TEMP-42) to (TEMP-68).
[0433] [Chemical Formula 12]
[0434]
[0435] [Chemical Formula 13]
[0436]
[0437] Among the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.
[0438] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.
[0439] [Chemical Formula 14]
[0440]
[0441] Among the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each independently It is a hydrogen atom or a substituent.
[0442] Formula Q9 and Q 10 They may also join together through single bonds to form a ring.
[0443] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.
[0444] [Chemical Formula 15]
[0445]
[0446] Among the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently It is a hydrogen atom or a substituent.
[0447] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.
[0448] The bivalent complex ring with or without substitution described in this specification is preferably one of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise specified in this specification.
[0449] [Chemical Formula 16]
[0450]
[0451] [Chemical Formula 17]
[0452]
[0453] [Chemical Formula 18]
[0454]
[0455] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently hydrogen atoms or substituents.
[0456] [Chemical Formula 19]
[0457]
[0458] [Chemical Formula 20]
[0459]
[0460] [Chemical Formula 21]
[0461]
[0462] [Chemical Formula 22]
[0463]
[0464] Among the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently It is a hydrogen atom or a substituent.
[0465] The above is an explanation of the “substituents described in this specification.”
[0466] · "When combined to form a ring"
[0467] In the present specification, the phrase “one or more of two or more adjacent groups combine to form a substituted or non-substituted ring, combine to form a substituted or non-substituted condensed ring, or do not combine to each other” means the case where “one or more of two or more adjacent groups combine to form a substituted or non-substituted ring,” the case where “one or more of two or more adjacent groups combine to form a substituted or non-substituted condensed ring,” and the case where “one or more of two or more adjacent groups do not combine to each other.”
[0468] The following describes cases in this specification where "one or more groups of two or more adjacent groups combine to form a substituted or unsubstituted single ring" and "one or more groups of two or more adjacent groups combine to form a substituted or unsubstituted condensed ring" (hereinafter, these cases may be collectively referred to as "combining to form a ring"). An example is provided for an anthracene compound represented by the following general formula (TEMP-103), in which the matrix is an anthracene ring.
[0469] [Chemical Formula 23]
[0470]
[0471] For example, R 921 ~R 930In the case where "one or more sets of two or more adjacent groups combine to form a ring," the two adjacent groups that make up one set are R 921 and R 922 of, R 922 and R 923 of, R 923 and R 924 of, R 924 and R 930 of, R 930 and R 925 of, R 925 and R 926 of, R 926 and R 927 of, R 927 and R 928 of, R 928 and R 929 of, and R 929 and R 921 It is the group of.
[0472] The above "one or more sets" means that two or more sets of the above two or more adjacent sets may simultaneously form a ring. For example, R 921 and R 922 They combine with each other to form the ring Q A Forms, and simultaneously R 925 and R 926 These combine with each other to form the ring Q B In the case where it is formed, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).
[0473] [Chemical Formula 24]
[0474]
[0475] The case where "a group consisting of two or more adjacent units" forms a ring includes not only the case where a group consisting of "two" adjacent units combines as in the example above, but also the case where a group consisting of "three or more" adjacent units combines. For example, R 921 and R 922They combine with each other to form the ring Q A It forms, and also R 922 and R 923 These combine with each other to form the ring Q C Forms, and 3 adjacent (R 921 , R 922 and R 923 This refers to the case where groups consisting of ) combine with each other to form a ring and condense onto the anthracene matrix, and in this case, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C is R 922 Share.
[0476] [Chemical Formula 25]
[0477]
[0478] The formed "single ring" or "condensed ring" is a structure consisting solely of the formed ring, and may be a saturated ring or an unsaturated ring. Even if "a set of two adjacent rings" forms a "single ring" or a "condensed ring," the "single ring" or "condensed ring" may 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 are respectively a "single ring" or a "condensed ring." In addition, the ring Q formed in the above general formula (TEMP-105) A and ring Q C is a "condensed ring". The ring Q of the above general formula (TEMP-105) A and ring Q C is ring Q A and ring Q C It becomes a condensed ring through condensation. The ring Q of the above general formula (TMEP-104) A If is a benzene ring, then ring Q A is a single ring. The ring Q of the above general formula (TMEP-104)A If is a naphthalene ring, then ring Q A is a condensed ring.
[0479] "Unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic complex ring. "Saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic complex ring.
[0480] As a specific example of an aromatic hydrocarbon ring, a structure in which the group given as a specific example in specific example group G1 is terminated by a hydrogen atom can be cited.
[0481] As a specific example of an aromatic complex ring, a structure in which an aromatic complex ring group is terminated by a hydrogen atom can be cited as a specific example in the group of specific examples G2.
[0482] As a specific example of an aliphatic hydrocarbon ring, a structure in which the group given as a specific example in the specific example group G6 is terminated by a hydrogen atom can be cited.
[0483] "Forming a ring" means forming a ring with only multiple atoms of the matrix or with multiple atoms of the matrix and one or more additional arbitrary elements. For example, R represented in the above general formula (TEMP-104). 921 and R 922 A ring Q formed by the combination of each other A is, R 921 The carbon atom of the anthracene skeleton that bonds with this, and R 922 It refers to a ring formed by a carbon atom of the anthracene skeleton to which it bonds, and one or more arbitrary elements. As a specific example, R 921 and R 922 Lo ring Q A In the case where it forms, R 921 The carbon atom of the anthracene skeleton that bonds with this, and R 922 In the case where it forms a monocyclic unsaturated ring with four carbon atoms and a carbon atom of the anthracene skeleton to which it bonds, R 921 and R 922 The ring formed by is a benzene ring.
[0484] Here, "any element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur elements, unless otherwise specified in this specification. In any element (e.g., in the case of a carbon or nitrogen element), bonds that do not form a ring may be terminated by a hydrogen atom or the like, or substituted by an "any substituent" described below. When any element other than a carbon element is included, the ring formed is a complex ring.
[0485] Unless otherwise specified in this specification, “one or more of any elements” constituting a single ring or a condensed ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5.
[0486] Unless otherwise specified in this specification, among "single ring" and "condensed ring," it is preferably "single ring".
[0487] Unless otherwise specified in this specification, among "saturated ring" and "unsaturated ring," it is preferably "unsaturated ring."
[0488] Unless otherwise stated in this specification, "single ring" is preferably a benzene ring.
[0489] Unless otherwise specified in this specification, the “unsaturated ring” is preferably a benzene ring.
[0490] In cases where “one or more sets of two or more adjacent elements” “combine with one another to form a substituted or unsubstituted ring” or “combine with one another to form a substituted or unsubstituted condensed ring,” unless otherwise specified in this specification, preferably, one or more sets of two or more adjacent elements combine with one another to form a substituted or unsubstituted “unsaturated ring” composed of a plurality of atoms of the matrix and at least one element selected from the group consisting of 1 to 15 carbon elements, nitrogen elements, oxygen elements, and sulfur elements.
[0491] The substituent in the case where the above-mentioned "single ring" or "condensed ring" has a substituent is, for example, an "optional substituent" described below. Specific examples of the substituent in the case where the above-mentioned "single ring" or "condensed ring" has a substituent are the substituents described in the aforementioned section "Substituents described in this specification."
[0492] The substituent in the case where the above-mentioned "saturated ring" or "unsaturated ring" has a substituent is, for example, an "optional substituent" described below. Specific examples of the substituent in the case where the above-mentioned "mono-ring" or "condensed ring" has a substituent are the substituents described in the aforementioned section "Substituents described in this specification."
[0493] The above is an explanation of the case where “one or more of two or more adjacent groups combine to form a single ring with or without substitution” and the case where “one or more of two or more adjacent groups combine to form a condensed ring with or without substitution” (the case where they combine to form a ring).
[0494] · Substituents in the case of "substituent or non-substituent"
[0495] In one embodiment of this specification, the substituent in the case of "substituted or non-substituted" (which may be referred to as "optional substituent" in this specification) is, for example
[0496] Unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0497] Unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[0498] Unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[0499] Unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[0500] -Si(R 901 )(R 902 )(R 903 ),
[0501] -O-(R 904 ),
[0502] -S-(R 905 ),
[0503] -N(R 906 )(R 907 ),
[0504] Halogen atoms,
[0505] Cyanogi,
[0506] Nitro,
[0507] An unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[0508] Unsubstituted complex circulators with 5 to 50 ring-forming atoms
[0509] It is a group selected from the group consisting of, and
[0510] Here, R 901 ~R 907 each independently
[0511] hydrogen atom,
[0512] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0513] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[0514] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0515] It is a complex circulator with 5 to 50 atoms forming a ring, either substituent or unsubstituent.
[0516] R 901 If there are 2 or more of these, 2 or more R 901 They are identical or different from each other,
[0517] R 902 If there are 2 or more, 2 or more R 902 are identical or different from each other,
[0518] R 903 If there are 2 or more of these, 2 or more R 903 They are identical or different from each other,
[0519] R 904 If there are 2 or more, 2 or more R 904 are identical or different from each other,
[0520] R 905 If there are 2 or more, 2 or more R 905 are identical or different from each other,
[0521] R 906 If there are 2 or more of these, 2 or more R 906 They are identical or different from each other,
[0522] R 907 If there are 2 or more of these, 2 or more R 907 They are identical or different from each other.
[0523] In one embodiment, the substituent in the case of "substituted or non-substituted" is,
[0524] alkyl group having 1 to 50 carbon atoms,
[0525] A ring-forming aryl group having 6 to 50 carbon atoms, and
[0526] Complex circulators with 5 to 50 ring-forming atoms
[0527] It is a group selected from the group consisting of
[0528] In one embodiment, the substituent in the case of "substituted or non-substituted" is,
[0529] alkyl group having 1 to 18 carbon atoms,
[0530] A ring-forming aryl group having 6 to 18 carbon atoms, and
[0531] Complex circulators with 5 to 18 ring-forming atoms
[0532] It is a group selected from the group consisting of
[0533] The specific examples of each of the above arbitrary substituents are specific examples of substituents described in the aforementioned section “Substituents described in this specification”.
[0534] Unless otherwise specified in this specification, any adjacent substituents may form a “saturated ring” or an “unsaturated ring,” 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, and more preferably forming a benzene ring.
[0535] Unless otherwise stated in this specification, any substituent may have additional substituents. The additional substituents of any substituent are identical to the said arbitrary substituent.
[0536] In the present specification, the numerical range indicated using “AA to BB” means a range that includes the numerical value AA listed before “AA to BB” as a lower limit value and the numerical value BB listed after “AA to BB” as an upper limit value.
[0537] [First embodiment]
[0538] (Organic Electroluminescence Device)
[0539] The organic electroluminescence device (organic EL device) of the present embodiment has a cathode, an anode, a light-emitting region disposed between the cathode and the anode, a first anode-side organic layer, a second anode-side organic layer, and a third anode-side organic layer, wherein the light-emitting region includes at least one light-emitting layer, and the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer are disposed in the order of the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer from the anode side between the anode and the light-emitting region, and the third anode-side organic layer does not contain the compound contained in the second anode-side organic layer. The organic EL device of the present embodiment may be an organic EL device of various forms that further include other elements in addition to these elements. For example, the following first, second, third, fourth, and fifth forms may be cited as examples of forms of the organic EL device of the present embodiment. In addition, the organic EL device of the present embodiment is not limited to these embodiments.
[0540] An organic EL device according to the first embodiment of the present invention has a cathode, an anode, a light-emitting region disposed between the cathode and the anode, a first anode-side organic layer, a second anode-side organic layer, and a third anode-side organic layer, wherein the light-emitting region comprises at least one light-emitting layer, and the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer are disposed in the order of the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer from the anode side between the anode and the light-emitting region, and the third anode-side organic layer does not contain the compound contained in the second anode-side organic layer, and the sum of the film thickness of the second anode-side organic layer and the film thickness of the third anode-side organic layer is 30 nm or more and 150 nm or less, and the ratio of the film thickness of the second anode-side organic layer to the film thickness of the third anode-side organic layer satisfies the relationship of the following formula (Equation A1).
[0541] 0.50 < TL3 / TL2 < 4.0 … (Mathematical Formula A1)
[0542] (TL2 is the film thickness of the second anode-side organic layer, TL3 is the film thickness of the third anode-side organic layer, and the unit of film thickness is nm.)
[0543] An organic EL device according to a second aspect of the present embodiment comprises a cathode, an anode, a light-emitting region disposed between the cathode and the anode, a first anode-side organic layer, a second anode-side organic layer, and a third anode-side organic layer, wherein the light-emitting region comprises at least one light-emitting layer, and the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer are disposed between the anode and the light-emitting region in the order of the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer from the anode side, wherein the third anode-side organic layer does not contain the compound contained in the second anode-side organic layer, and the third anode-side organic layer contains a compound represented by the following general formula (C1) or a compound represented by the following general formula (C2), wherein the sum of the film thickness of the second anode-side organic layer and the film thickness of the third anode-side organic layer is 30 nm or more and 150 nm or less, and the film thickness of the second anode-side organic layer and the third anode-side The ratio of the film thicknesses of the organic layer satisfies the relationship of the following formula (Equation A2).
[0544] 0.30 < TL3 / TL2 < 4.0 … (Mathematical Formula A2)
[0545] (TL2 is the film thickness of the second anode-side organic layer, TL3 is the film thickness of the third anode-side organic layer, and the unit of film thickness is nm.)
[0546] [Chemical Formula 26]
[0547]
[0548] (In the above general formula (C1),
[0549] L A1 , L A2 and L A3 each independently
[0550] single bond,
[0551] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[0552] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0553] Ar 111 , Ar 112 and Ar 113 each independently
[0554] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
[0555] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, or
[0556] -Si(R C1 )(R C2 )(R C3 ) and,
[0557] R C1 , R C2 and R C3 Each is independently a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[0558] R C1 If this plural exists, the plural R C1 They are identical or different from each other,
[0559] R C2 If there are multiple instances of R C2 are identical or different from each other,
[0560] R C3 If this plural exists, the plural R C3 They are identical or different from each other.
[0561] [Chemical Formula 27]
[0562]
[0563] (In the above general formula (C2),
[0564] L B1 , L B2 , L B3 and L B4 are, each independently
[0565] single bond, or
[0566] It is a substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, and
[0567] Ar 121 , Ar 122 , Ar 123 , Ar 124 and Ar 125 are, each independently
[0568] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0569] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[0570] (In the compound represented by the above general formula (C1) and the compound represented by the above general formula (C2), the substituent in the case of “substituted or unsubstituted” is -N(R C6 )(R C7 It is not the one indicated by ), R C6 and R C7 Each is independently a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, a substituted or unsubstituted ring-forming C6–50 aryl group, or a substituted or unsubstituted ring-forming heterocyclic group with 5–50 atoms.
[0571] An organic EL device according to a third aspect of the present embodiment comprises a cathode, an anode, a light-emitting region disposed between the cathode and the anode, a first anode-side organic layer, a second anode-side organic layer, and a third anode-side organic layer, wherein the light-emitting region comprises at least one light-emitting layer, and the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer are disposed between the anode and the light-emitting region in the order of the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer, starting from the anode side, wherein the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer each comprise one or more different compounds, and the third anode-side organic layer does not contain the compound contained in the second anode-side organic layer, and the third anode-side organic layer contains a third hole transport band material, and the hole mobility μh(cHT3) of the third hole transport band material is 1.0 × 10⁻⁶ -5 cm 2 It is greater than / Vs, and the energy level HOMO(cHT3) of the highest point orbit of the third hole transport band material is -5.6 eV or less.
[0572] An organic EL device according to the fourth embodiment of the present invention has a cathode, an anode, a light-emitting region disposed between the cathode and the anode, a first anode-side organic layer, a second anode-side organic layer, and a third anode-side organic layer, wherein the light-emitting region comprises at least one light-emitting layer, and the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer are disposed in the order of the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer from the anode side between the anode and the light-emitting region, and the third anode-side organic layer does not contain the compound contained in the second anode-side organic layer, and the sum of the film thickness of the second anode-side organic layer and the film thickness of the third anode-side organic layer is 100 nm or more.
[0573] An organic EL device according to the fifth aspect of the present embodiment comprises a cathode, an anode, a light-emitting region disposed between the cathode and the anode, a first anode-side organic layer, a second anode-side organic layer, and a third anode-side organic layer, wherein the light-emitting region comprises at least one light-emitting layer, and the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer are disposed in the order of the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer from the anode side, between the anode and the light-emitting region, wherein the third anode-side organic layer does not contain the compound contained in the second anode-side organic layer, and the sum of the film thickness of the second anode-side organic layer and the film thickness of the third anode-side organic layer is 30 nm or more, and the ratio of the film thickness of the second anode-side organic layer to the film thickness of the third anode-side organic layer satisfies the relationship of the following formula (Equation A4), and the third anode-side organic layer contains a third hole transport band material, and The singlet energy of the third hole transport band material is greater than 3.12 eV.
[0574] 0.30 < TL3 / TL2 < 5.0 … (Mathematical Formula A4)
[0575] (TL2 is the film thickness of the second anode-side organic layer, TL3 is the film thickness of the third anode-side organic layer, and the unit of film thickness is nm.)
[0576] The elements that an organic EL element of each embodiment of the present embodiment may have are described below. The first, second, third, fourth, and fifth embodiments described above are examples of embodiments that include one or more elements selected from the elements described below.
[0577] According to the present embodiment, the device performance of an organic EL device can be improved. In one aspect of the present embodiment, the luminous efficiency of the organic EL device is improved. In one aspect of the present embodiment, the organic EL device has a long lifespan.
[0578] By utilizing a layer made of a low-refractive-index material as an organic layer (e.g., a hole transport layer) in the hole transport band, light emission loss due to the evanescent mode can be reduced. Additionally, as an organic layer in the hole transport band (e.g., a hole transport layer), by placing an organic layer made of a high-refractive-index material on the anode side and an organic layer made of a low-refractive-index material on the emissive-layer side, light emission loss in the thin-film mode can be reduced. In particular, light extraction in a bottom-emission type organic electroluminescence device can simultaneously prevent light emission loss in the organic thin-film layer as well as light emission loss in the substrate mode, thereby further improving efficiency. In particular, if the film thickness of the organic layer made of a low-refractive-index material is 20 nm or more, the light extraction efficiency can be effectively increased. Furthermore, in the organic layer in the hole transport band, hole supply characteristics can be easily adjusted by combining two different types of materials.
[0579] (Precision Transport Band)
[0580] In this specification, a region consisting of a plurality of organic layers disposed between an anode and a light-emitting region may be referred to as a hole transport band.
[0581] In one embodiment of the organic EL device of the present embodiment, the ratio TL3 / TL2 of the film thickness TL2 of the second anode-side organic layer and the film thickness TL3 of the third anode-side organic layer satisfies a predetermined relationship.
[0582] In one embodiment of the organic EL device of the present embodiment, the ratio of the film thickness of the second anode-side organic layer to the film thickness of the third anode-side organic layer satisfies the relationship of the following formula (Formula A1), formula (Formula A2), formula (Formula A3), or formula (Formula A4).
[0583] 0.50 < TL3 / TL2 < 4.0 … (Mathematical Formula A1)
[0584] 0.30 < TL3 / TL2 < 4.0 … (Mathematical Formula A2)
[0585] 0.75 < TL3 / TL2 < 3.0 … (Mathematical Formula A3)
[0586] 0.30 < TL3 / TL2 < 5.0 … (Mathematical Formula A4)
[0587] (TL2 is the film thickness of the second anode-side organic layer, TL3 is the film thickness of the third anode-side organic layer, and the unit of film thickness is nm.)
[0588] In one embodiment of the organic EL device of the present embodiment, the non-TL3 / TL2 is 1 or more.
[0589] In one embodiment of the organic EL device of the present embodiment, the ratio TL3 / TL2 is 2.5 or less.
[0590] In one embodiment of the organic EL device of the present embodiment, the sum of the film thickness of the second anode-side organic layer and the film thickness of the third anode-side organic layer is 30 nm or more, 70 nm or more, or 100 nm or more.
[0591] In the organic EL device of the present embodiment, it is believed that the excitation energy of the emitting layer can be prevented from moving to the hole transport band by making the film thickness of the organic layer of the hole transport band disposed on the anode side of the emitting region large (e.g., the sum of the film thickness of the second anode-side organic layer and the film thickness of the third anode-side organic layer is 30 nm or more), and by making the ratio of the film thickness of the second anode-side organic layer to the film thickness of the third anode-side organic layer within a predetermined range (e.g., within the range of the above formula (Equation A1), Equation A2), Equation A3, or Equation A4). It is believed that by preventing the movement of the excitation energy of the emitting layer, the luminous efficiency of the organic EL device is improved.
[0592] In one embodiment of the organic EL device of the present embodiment, the sum of the film thickness of the second anode-side organic layer and the film thickness of the third anode-side organic layer is 150 nm or less.
[0593] In one embodiment of the organic EL device of the present embodiment, the sum of the film thickness of the first anode-side organic layer, the film thickness of the second anode-side organic layer, and the film thickness of the third anode-side organic layer is 150 nm or less.
[0594] In one embodiment of the organic EL device of the present embodiment, the film thickness of the third anode-side organic layer is 15 nm or more or 20 nm or more.
[0595] It is thought that by having a film thickness of 15 nm or more of the third anode-side organic layer, the third anode-side organic layer becomes more effective in preventing the transfer of excitation energy of the light-emitting layer.
[0596] In one embodiment of the organic EL device of the present embodiment, the film thickness of the third anode-side organic layer is 80 nm or less, 75 nm or less, or 60 nm or less.
[0597] From the perspective of improving light extraction efficiency, the film thickness of the third anode-side organic layer is preferably 15 nm or more and 75 nm or less, and more preferably 20 nm or more and 60 nm or less.
[0598] In one aspect of the organic EL device of the present embodiment, the difference NM2-NM3 between the refractive index NM2 of the constituent material included in the second anode-side organic layer and the refractive index NM3 of the constituent material included in the third anode-side organic layer satisfies the relationship of the following formula (Equation N1). The refractive index NM2 of the constituent material included in the second anode-side organic layer corresponds to the refractive index of said one compound when the second anode-side organic layer contains said one compound, and corresponds to the refractive index of said mixture containing said multiple compounds when the second anode-side organic layer contains said multiple compounds. The refractive index NM3 of the constituent material included in the third anode-side organic layer is also defined in the same way as the refractive index NM2 of the constituent material included in the second anode-side organic layer. The refractive index can be measured by the measurement method described in the example to be described later. In this specification, the refractive index at 2.7 eV in the substrate parallel direction (ordinary direction) measured by multi-angle incident spectroscopic ellipsometry is defined as the refractive index of the material being measured. The refractive index at 2.7 eV corresponds to the refractive index at 460 nm.
[0599] NM2 - NM3 ≥ 0.05 … (Mathematical formula N1)
[0600] By satisfying the relationship of the above formula (mathematical formula N1), the light extraction efficiency of the organic EL device is improved.
[0601] In one embodiment of the organic EL device of the present embodiment, the difference NM2-NM3 between the refractive index NM2 of the constituent material included in the second anode-side organic layer and the refractive index NM3 of the constituent material included in the third anode-side organic layer satisfies the relationship of the following formula (formula N2) or (formula N3).
[0602] NM2 - NM3 ≥ 0.10 … (Mathematical formula N2)
[0603] NM2 - NM3 ≥ 0.075 … (Mathematical formula N3)
[0604] In this specification, the refractive index at 2.7 eV (460 nm) in the substrate parallel direction (ordinary direction) is n ORD denoted as , and the refractive index at 2.7 eV (460 nm) in the direction perpendicular to the substrate (extra-ordinary direction) is n EXT There are cases where it is written as .
[0605] In one embodiment of the organic EL device of the present embodiment, the refractive index n at 460 nm of the constituent material included in the second anode-side organic layer ORD and refractive index n EXT The difference n ORD -n EXT It is desirable that it be 0.1 or higher.
[0606] In one embodiment of the organic EL device of the present embodiment, the refractive index of the compound contained in the second anode-side organic layer is 1.94 or higher.
[0607] In one embodiment of the organic EL device of the present embodiment, the refractive index of the compound contained in the third anode-side organic layer is 1.89 or less.
[0608] In one embodiment of the organic EL device of the present embodiment, the distance from the anode-side interface of the third anode-side organic layer to the anode-side interface of the light-emitting layer disposed on the anode side of the light-emitting region is 20 nm or more.
[0609] By having a distance of 20 nm or more from the anode-side interface of the third anode-side organic layer to the anode-side interface of the light-emitting layer positioned closest to the anode in the light-emitting region, it becomes easier to improve light extraction efficiency.
[0610] The distance from the anode-side interface of the third anode-side organic layer to the anode-side interface of the light-emitting layer positioned at the most anode side in the light-emitting region is, for example, equivalent to the film thickness of the third anode-side organic layer in the case where the third anode-side organic layer is in direct contact with the second anode-side organic layer on the anode side and in direct contact with the light-emitting layer positioned at the most anode side in the light-emitting region on the cathode side.
[0611] In addition, the distance from the anode-side interface of the third anode-side organic layer to the anode-side interface of the light-emitting layer positioned at the anode side of the light-emitting region is, for example, equivalent to the total film thickness of the third anode-side organic layer and the fourth anode-side organic layer, in the case where the third anode-side organic layer is in direct contact with the second anode-side organic layer on the anode side and in direct contact with the fourth anode-side organic layer described later on the cathode side, and the fourth anode-side organic layer is in direct contact with the light-emitting layer positioned at the anode side of the light-emitting region on the cathode side.
[0612] In one embodiment of the organic EL device of the present embodiment, the distance from the anode-side interface of the third anode-side organic layer to the anode-side interface of the light-emitting layer positioned at the anode side of the light-emitting region is 30 nm or more.
[0613] In one embodiment of the organic EL device of the present embodiment, the third anode-side organic layer contains a compound represented by the general formula (C1) or a compound represented by the general formula (C2).
[0614] In one embodiment of the organic EL device of the present embodiment, the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer each comprise one or more different compounds.
[0615] In one embodiment of the organic EL device of the present embodiment, the first anode-side organic layer and the second anode-side organic layer may both contain a compound represented by the general formula (C1) or a compound represented by the general formula (C2), but the compounds contained in the first anode-side organic layer and the second anode-side organic layer have different molecular structures from the compounds contained in the third anode-side organic layer.
[0616] In one embodiment of the organic EL device of the present embodiment, the compounds contained in the second anode-side organic layer are all different from the compounds contained in the third anode-side organic layer.
[0617] An example of an embodiment satisfying this condition is that the second anode-side organic layer contains one type of compound AA and the third anode-side organic layer contains one type of compound BB.
[0618] In addition, for example, even if the second anode-side organic layer contains two types of compounds AA and AB and the third anode-side organic layer contains one type of compound BB, the above conditions are satisfied because compounds AA and AB are both different from compound BB. Compounds AA, AB, and BB are different compounds from each other.
[0619] On the other hand, for example, if the second anode-side organic layer contains two types of compounds AA and AB, and the third anode-side organic layer contains one type of compound AB, the above conditions are not satisfied because the second anode-side organic layer and the third anode-side organic layer contain the same compound with respect to compound AB.
[0620] In one embodiment of the organic EL device of the present embodiment, the third anode-side organic layer contains a third hole transport band material. The compound contained in the third anode-side organic layer may be referred to as the third hole transport band material.
[0621] In one aspect of the organic EL device of the present embodiment, the hole mobility μh (cHT3) of the third hole transport band material is 1.0 × 10⁻⁶ -5 cm 2 It is greater than / Vs.
[0622] In one embodiment of the organic EL device of the present embodiment, the energy level HOMO (cHT3) of the highest point orbit of the third hole transport band material is -5.6 eV or less.
[0623] In one aspect of the organic EL device of the present embodiment, the hole mobility μh (cHT3) of the third hole transport band material is 1.0×10 -5 cm 2 It is greater than / Vs, and the energy level HOMO(cHT3) of the highest point orbit of the third hole transport band material is -5.6 eV or less. If the hole mobility μh(cHT3) and HOMO(cHT3) of the third hole transport band material are in this range, the hole mobility of the third anode-side organic layer is high, and the hole injection into the emissive layer in the emission region is also high.
[0624] In one embodiment of the organic EL device of the present embodiment, the singlet energy of the third hole transport band material is greater than 3.12 eV.
[0625] In one embodiment of the organic EL device of the present embodiment, the singlet energy of the third hole transport band material is 3.15 eV or higher.
[0626] In one embodiment of the organic EL device of the present embodiment, the singlet energy of the third hole transport band material is 3.40 eV or less or 3.30 eV or less.
[0627] In one embodiment of the organic EL device of the present embodiment, the third hole transport band material is a compound represented by the general formula (C1) or a compound represented by the general formula (C2).
[0628] The compound represented by the above general formula (C1) is preferably a compound represented by the following general formula (C11).
[0629] In one embodiment of the organic EL device of the present embodiment, the third hole transport band material is a compound represented by the following general formula (C11).
[0630] [Chemical Formula 28]
[0631]
[0632] (In the above general formula (C11), Ar 111 , Ar 112 , Ar 113 and L A3 Each is Ar in the above general formula (C1). 111 , Ar 112 , Ar 113 and L A3 It has the same meaning as, and n1 and n2 are 4, and
[0633] Multiple R C11 They are identical or different from each other,
[0634] Multiple R C11 One or more of the groups consisting of two or more adjacent groups,
[0635] They combine with each other to form a substituted or unsubstituted single ring,
[0636] They combine with each other to form substituted or unsubstituted condensed rings, or
[0637] They do not combine with each other,
[0638] Multiple R C12 are identical or different from each other,
[0639] Multiple R C12 One or more of the groups consisting of two or more adjacent groups,
[0640] They combine with each other to form a substituted or unsubstituted single ring,
[0641] They combine with each other to form substituted or unsubstituted condensed rings, or
[0642] They do not combine with each other,
[0643] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. C11 and R C12 are, each independently
[0644] hydrogen atom,
[0645] Cyanogi,
[0646] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0647] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[0648] -Si(R 901 )(R 902 )(R 903 ),
[0649] -O-(R 904 ),
[0650] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0651] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[0652] In the compound represented by the above general formula (C1) and the above general formula (C11), Ar 111 , Ar 112 and Ar 113 It is preferable that at least one of them be selected from the group consisting of the following general formulas (21a), (21b), (21c), (21d) and (21e).
[0653] [Chemical Formula 29]
[0654]
[0655] (In the above general formulas (21a), (21b), (21c), (21d) and (21e),
[0656] X21 NR 21 , CR 22 R 23 , is an oxygen atom or a sulfur atom,
[0657] X 21 In this case, multiple X 21 They are identical or different from each other,
[0658] X 21 This CR 22 R 23 In the case of, R 22 and R 23 A group consisting of,
[0659] They combine with each other to form a substituted or unsubstituted single ring,
[0660] They combine with each other to form substituted or unsubstituted condensed rings, or
[0661] They do not combine with each other,
[0662] R 21 , and R which does not form the above-mentioned substituted or unsubstituted single ring, and also does not form the above-mentioned substituted or unsubstituted condensed ring. 22 and R 23 each independently
[0663] hydrogen atom,
[0664] Cyanogi,
[0665] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0666] Substituted or unsubstituted alkyl halides having 1 to 50 carbon atoms,
[0667] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[0668] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[0669] -O-(R 904 The one indicated by ),
[0670] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0671] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[0672] R 211 ~R 218 One or more of the groups consisting of two or more adjacent groups,
[0673] They combine with each other to form a substituted or unsubstituted single ring,
[0674] They combine with each other to form substituted or unsubstituted condensed rings, or
[0675] Without combining with each other,
[0676] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 211 ~R 218 each independently
[0677] hydrogen atom,
[0678] Cyanogi,
[0679] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0680] Substituted or unsubstituted alkyl halides having 1 to 50 carbon atoms,
[0681] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[0682] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[0683] -O-(R 904 The one indicated by ),
[0684] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0685] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0686] In the above general formulas (21a), (21b), (21c), (21d) and (21e), * is independently L A1 , L A2 and L A3 It is the connection location with.)
[0687] Ar that is not a group selected from the group consisting of the groups represented by the above general formulas (21a), (21b), (21c), (21d) and (21e). 111 , Ar 112 and Ar 113 It is preferable that each is independently a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, and more preferable that it is a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.
[0688] In the compound represented by the above general formula (C1), Ar 111 , Ar 112 and Ar 113 Two of them are selected from the group consisting of the general formulas (21a), (21b), (21c), (21d) and (21e) above, and Ar 111 , Ar 112 and Ar 113 It is also desirable that one of them is a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms.
[0689] In the compound represented by the above general formula (C1), Ar 111 , Ar 112 and Ar 113 One of them is a group selected from the group consisting of the general formulas represented by the above general formulas (21a), (21b), (21c), (21d) and (21e), and Ar 111 , Ar 112 and Ar 113 It is also desirable that the other two are substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms.
[0690] In one embodiment of the organic EL device of the present embodiment, the second anode-side organic layer contains a second hole transport band material. The compound contained in the second anode-side organic layer may be referred to as the second hole transport band material.
[0691] In one embodiment of the organic EL device of the present embodiment, the second hole transport band material and the third hole transport band material are different compounds.
[0692] In one aspect of the organic EL device of the present embodiment, the hole mobility μh (cHT2) of the second hole transport band material is 1.0 × 10⁻⁶ -4 cm 2 It is greater than / Vs.
[0693] In one embodiment of the organic EL device of the present embodiment, the hole mobility μh (cHT2) of the second hole transport band material is greater than the hole mobility μh (cHT3) of the third hole transport band material.
[0694] In one aspect of the organic EL device of the present embodiment, the energy level HOMO (cHT2) of the highest point orbit of the second hole transport band material and the energy level HOMO (cHT3) of the highest point orbit of the third hole transport band material satisfy the relationship of the following formula (Equation B1).
[0695] HOMO(cHT2) < HOMO(cHT3) … (Equation B1)
[0696] In one aspect of the organic EL device of the present embodiment, the hole mobility μh (cHT2) of the second hole transport band material is 1.0 × 10⁻⁶ -4 cm 2 It is greater than / Vs, and the hole mobility μh(cHT3) of the third hole transport band material is 1.0×10 -5 cm 2It is greater than / Vs, and also the energy level HOMO (cHT2) of the highest point orbit of the second hole transport band material and the energy level HOMO (cHT3) of the highest point orbit of the third hole transport band material satisfy the relationship of the above formula (Equation B1).
[0697] In one embodiment of the organic EL device of the present embodiment, the second hole transport band material is a compound represented by the general formula (C1) or the general formula (C2).
[0698] In one embodiment of the organic EL device of the present embodiment, the second anode-side organic layer and the third anode-side organic layer may both contain a compound represented by the general formula (C1), but the compound contained in the second anode-side organic layer and the compound contained in the third anode-side organic layer have different molecular structures.
[0699] In one embodiment of the organic EL device of the present embodiment, the second anode-side organic layer and the third anode-side organic layer may both contain a compound represented by the general formula (C2), but the compound contained in the second anode-side organic layer and the compound contained in the third anode-side organic layer have different molecular structures.
[0700] In one embodiment of the organic EL device of the present embodiment, the third anode-side organic layer contains at least one compound selected from the group consisting of a compound represented by the following general formula (cHT3-1), a compound represented by the general formula (cHT3-2), a compound represented by the general formula (cHT3-3), and a compound represented by the general formula (cHT3-4).
[0701] [Chemical Formula 30]
[0702]
[0703] [Chemical Formula 31]
[0704]
[0705] [Chemical Formula 32]
[0706]
[0707] [Chemical Formula 33]
[0708]
[0709] (In the above general formulas (cHT3-1), (cHT3-2), (cHT3-3) and (cHT3-4),
[0710] Ar 311 is a group represented by any one of the following general formulas (1-a), (1-b), (1-c) and (1-d), and
[0711] Ar 312 and Ar 313 each independently
[0712] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
[0713] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, or
[0714] -Si(R C1 )(R C2 )(R C3 ) and,
[0715] R C1 , R C2 and R C3 Each independently It is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[0716] R C1 If this plural exists, the plural R C1 They are identical or different from each other,
[0717] R C2 If there are multiple instances of R C2 are identical or different from each other,
[0718] R C3 If this plural exists, the plural R C3 They are identical or different from each other,
[0719] L D1 , LD2 and L D3 each independently
[0720] single bond,
[0721] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[0722] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0723] R D20 ~R D24 One or more of the groups consisting of two or more adjacent groups,
[0724] They combine with each other to form a substituted or unsubstituted single ring,
[0725] They combine with each other to form substituted or unsubstituted condensed rings, or
[0726] Without combining with each other,
[0727] R D31 ~R D38 One or more of the groups consisting of two or more adjacent groups,
[0728] They combine with each other to form a substituted or unsubstituted single ring,
[0729] They combine with each other to form substituted or unsubstituted condensed rings, or
[0730] They do not combine with each other,
[0731] R D40 ~R D44 One or more of the groups consisting of two or more adjacent groups,
[0732] They combine with each other to form a substituted or unsubstituted single ring,
[0733] They combine with each other to form substituted or unsubstituted condensed rings, or
[0734] Without combining with each other,
[0735] X3 is an oxygen atom, a sulfur atom, or C(R D45 )(R D46 ) and,
[0736] R D45 and R D46 A group consisting of,
[0737] They combine with each other to form a substituted or unsubstituted single ring,
[0738] They combine with each other to form substituted or unsubstituted condensed rings, or
[0739] Without combining with each other,
[0740] R D25 , R which does not form the above-mentioned or unsubstituted single ring, and also does not form the above-mentioned or unsubstituted condensed ring. D20 ~R D24 , R D31 ~R D38 , R D40 ~R D44 , R D45 and R D46 each independently
[0741] hydrogen atom,
[0742] Cyanogi,
[0743] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0744] Substituted or unsubstituted alkyl halides having 1 to 50 carbon atoms,
[0745] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[0746] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[0747] -O-(R 904 The one indicated by ),
[0748] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0749] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0750] Multiple R D20 They are identical or different from each other,
[0751] Multiple R D40 They are identical or different from each other,
[0752] R among the compounds represented by the above general formulas (cHT3-1), (cHT3-2), (cHT3-3), and (cHT3-4). 901 ~R 904 are, each independently
[0753] hydrogen atom,
[0754] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0755] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[0756] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0757] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[0758] R 901 In this case, multiple Rs 901 They are identical or different from each other,
[0759] R 902 If there are multiple cases, multiple R 902 are identical or different from each other,
[0760] R 903 In this case, multiple Rs 903 They are identical or different from each other,
[0761] R 904 If there are multiple cases, multiple R 904 are identical or different from each other.
[0762] [Chemical Formula 34]
[0763]
[0764] (Among the above general formula (1-a),
[0765] R 51 ~R 55Among them, groups consisting of two or more adjacent groups do not combine with each other,
[0766] R 51 ~R 55 are, each independently
[0767] hydrogen atoms, or
[0768] It is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and
[0769] ** is L D1 Indicates the binding location with.)
[0770] [Chemical Formula 35]
[0771]
[0772] (Among the above general formula (1-b),
[0773] R 61 ~R 68 One of them is a single bond that bonds to *b, and
[0774] R that is not a single bond bonding to *b 61 ~R 68 Among them, groups consisting of two or more adjacent elements do not combine with each other,
[0775] R that is not a single bond bonding to *b 61 ~R 68 Each independently A hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted ring-forming C6-C12 aryl group, and
[0776] ** is L D1 Indicates the binding location with.)
[0777] [Chemical Formula 36]
[0778]
[0779] (Among the above general formula (1-c),
[0780] R 71 ~R 80 One of them is a single bond that binds to *d, and
[0781] R that is not a single bond bonding to *d 71 ~R 80 Among them, groups consisting of two or more adjacent groups do not combine with each other,
[0782] R that is not a single bond bonding to *d 71 ~R 80 each independently
[0783] hydrogen atom,
[0784] A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or
[0785] It is a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, and
[0786] ** is L D1 Indicates the binding location with.)
[0787] [Chemical Formula 37]
[0788]
[0789] (among the above general formula (1-d),
[0790] R 141 ~R 145 One of them is a single bond that binds to *h1, and R 141 ~R 145 The other one is a single bond that bonds to *h2, and
[0791] R that is not a single bond to *h1 and is not a single bond to *h2 141 ~R 145 Among them, groups consisting of two or more adjacent elements do not combine with each other,
[0792] R 151 ~R 155 One or more of the groups consisting of two or more adjacent groups,
[0793] They combine with each other to form a substituted or unsubstituted single ring,
[0794] They combine with each other to form substituted or unsubstituted condensed rings, or
[0795] Without combining with each other,
[0796] R 161 ~R 165 One or more of the groups consisting of two or more adjacent groups,
[0797] They combine with each other to form a substituted or unsubstituted single ring,
[0798] They combine with each other to form substituted or unsubstituted condensed rings, or
[0799] They do not combine with each other,
[0800] R that is not a single bond to *h1 and is not a single bond to *h2 141 ~R 145 , and R which does not form the above-mentioned or unsubstituted single ring, and also does not form the above-mentioned or unsubstituted condensed ring. 151 ~R 155 and R 161 ~R 165 are, each independently
[0801] hydrogen atom,
[0802] A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or
[0803] It is a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, and
[0804] ** is L D1 Indicates the binding location with.)
[0805] The compound represented by the above general formula (cHT3-1) may also be a compound represented by the following general formula (cHT3-11).
[0806] [Chemical Formula 38]
[0807]
[0808] (In the above general formula (cHT3-11), Ar 312 , Ar 313 , L D1 , L D2 , L D3 and R D25are, respectively, Ar in the above general formula (cHT3-1). 312 , Ar 313 , L D1 , L D2 , L D3 and R D25 It has the same meaning as,
[0809] R D26 ~R D29 One of them is L D1 It is a single bond that binds to, where *k indicates the bond position, and
[0810] R D21 ~R D24 and L D1 R that is not a single bond bonding to D26 ~R D29 One or more of the groups consisting of two or more adjacent groups,
[0811] They combine with each other to form a substituted or unsubstituted single ring,
[0812] They combine with each other to form substituted or unsubstituted condensed rings, or
[0813] They do not combine with each other,
[0814] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. D21 ~R D24 and R D26 ~R D29 are, each independently
[0815] hydrogen atom,
[0816] Cyanogi,
[0817] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0818] Substituted or unsubstituted alkyl halides having 1 to 50 carbon atoms,
[0819] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[0820] -Si(R 901 )(R 902 )(R 903The one indicated by ),
[0821] -O-(R 904 The one indicated by ),
[0822] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0823] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[0824] In one embodiment of the organic EL device of the present embodiment, R of the general formula (cHT3-11) D26 , R D28 or R D29 Ga L D1 It is a single bond that binds to.
[0825] R of the above general formula (cHT3-11) D26 This L D1 In the case of a single bond that binds to, the compound represented by the general formula (cHT3-11) above is represented by the following general formula (cHT3-12).
[0826] [Chemical Formula 39]
[0827]
[0828] R of the above general formula (cHT3-11) D28 This L D1 In the case of a single bond that binds to, the compound represented by the general formula (cHT3-11) above is represented by the following general formula (cHT3-13).
[0829] [Chemical Formula 40]
[0830]
[0831] R of the above general formula (cHT3-11) D29 Ga L D2 In the case of a single bond that binds to, the compound represented by the general formula (cHT3-11) above is represented by the following general formula (cHT3-14).
[0832] [Chemical Formula 41]
[0833]
[0834] (In the above general formula (cHT3-12), the above general formula (cHT3-13) and the above general formula (cHT3-14), Ar 312 , Ar 313 , L D1 , L D2 , L D3 and R D21 ~R D29 are, respectively, Ar in the above general formula (cHT3-11). 312 , Ar 313 , L D1 , L D2 , L D3 and R D21 ~R D29 It has the same meaning as.)
[0835] The compound represented by the above general formula (cHT3-3) may also be a compound represented by the following general formula (cHT3-31).
[0836] [Chemical Formula 42]
[0837]
[0838] (In the above general formula (cHT3-31), Ar 312 , Ar 313 , L D1 , L D2 , L D3 and X3 are each Ar in the above general formula (cHT3-3). 312 , Ar 313 , L D1 , L D2 , L D3 and has the same meaning as X3,
[0839] R D47 ~R D50 One of them is L D1 It is a single bond that binds to, and *m indicates the bond position,
[0840] R D41 ~R D44 and L D1 R that is not a single bond bonding to D47 ~R D50One or more of the groups consisting of two or more adjacent groups,
[0841] They combine with each other to form a substituted or unsubstituted single ring,
[0842] They combine with each other to form substituted or unsubstituted condensed rings, or
[0843] They do not combine with each other,
[0844] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. D41 ~R D50 each independently
[0845] hydrogen atom,
[0846] Cyanogi,
[0847] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0848] Substituted or unsubstituted alkyl halides having 1 to 50 carbon atoms,
[0849] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[0850] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[0851] -O-(R 904 The one indicated by ),
[0852] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0853] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[0854] In one aspect of the organic EL device of the present embodiment, L D1 This is a single bond, substituted, or unsubstituted phenylene group.
[0855] In one embodiment of the organic EL device of the present embodiment, in the compounds represented by the general formulas (cHT3-1) to (cHT3-4), (cHT3-11) to (cHT3-14) and (cHT3-31), the substituent in the case of "substituted or unsubstituted" is -N(R C6 )(R C7 It is not a device indicated by ).
[0856] In this embodiment, R C6 and R C7 Each is independently a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, a substituted or unsubstituted ring-forming C6–50 aryl group, or a substituted or unsubstituted ring-forming heterocyclic group with 5–50 atoms, and a plurality of R C6 are identical or different from each other, and multiple R C7 They are identical or different from each other.
[0857] In the case of "substituted or non-substituted," the substituent is -N(R C6 )(R C7 In cases where the group represented by ) is not the one, the compounds represented by the above general formulas (cHT3-1) to (cHT3-4), (cHT3-11) to (cHT3-14) and (cHT3-31) are monoamine compounds.
[0858] In one embodiment of the organic EL device of the present embodiment, the compound contained in the third anode-side organic layer is a diamine compound having two substituted or unsubstituted amino groups in the molecule.
[0859] In one embodiment of the organic EL device of the present embodiment, the compound contained in the third anode-side organic layer is a triamine compound having three substituted or unsubstituted amino groups in the molecule.
[0860] In one embodiment of the organic EL device of the present embodiment, the compound contained in the third anode-side organic layer is a tetraamine compound having four substituted or unsubstituted amino groups in the molecule.
[0861] In the case where the compounds represented by the above general formulas (cHT3-1) to (cHT3-4), (cHT3-11) to (cHT3-14) and (cHT3-31) are diamine compounds, the compounds represented by the above general formulas (cHT3-1) to (cHT3-4), (cHT3-11) to (cHT3-14) and (cHT3-31) have -N(R) as a substituent in the case of "substituted or unsubstituted". C6 )(R C7 It has one energy indicated by ).
[0862] In the case where the compounds represented by the above general formulas (cHT3-1) to (cHT3-4), (cHT3-11) to (cHT3-14) and (cHT3-31) are triamine compounds, the compounds represented by the above general formulas (cHT3-1) to (cHT3-4), (cHT3-11) to (cHT3-14) and (cHT3-31) have -N(R) as a substituent in the case of "substituted or unsubstituted". C6 )(R C7 It has two units indicated by ).
[0863] Where the compounds represented by the above general formulas (cHT3-1) to (cHT3-4), (cHT3-11) to (cHT3-14), and (cHT3-31) are tetraamine compounds, the compounds represented by the above general formulas (cHT3-1) to (cHT3-4), (cHT3-11) to (cHT3-14), and (cHT3-31) have -N(R) as a substituent in the case of "substituted or unsubstituted". C6 )(R C7 It has 3 units indicated by ).
[0864] In one embodiment of the organic EL device of the present embodiment, the third hole transport band material is at least one compound selected from the group consisting of compounds represented by the general formulas (cHT3-1) to (cHT3-4), (cHT3-11) to (cHT3-14) and (cHT3-31).
[0865] In one embodiment of the organic EL device of the present embodiment, the third hole transport band material is a monoamine compound, a diamine compound, a triamine compound, or a tetraamine compound.
[0866] In one embodiment of the organic EL device of the present embodiment, the second anode-side organic layer contains at least one compound selected from the group consisting of a compound represented by the following general formula (cHT2-1), a compound represented by the general formula (cHT2-2), and a compound represented by the general formula (cHT2-3).
[0867] [Chemical Formula 43]
[0868]
[0869] [Chemical Formula 44]
[0870]
[0871] [Chemical Formula 45]
[0872]
[0873] (In the above general formulas (cHT2-1), (cHT2-2) and (cHT2-3),
[0874] Ar 112 , Ar 113 , Ar 121 , Ar 122 , Ar 123 and Ar 124 are, each independently
[0875] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
[0876] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, or
[0877] -Si(R C1 )(R C2 )(R C3 ) and,
[0878] R C1 , R C2 and R C3 Each is independently a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[0879] R C1 If this plural exists, the plural R C1 They are identical or different from each other,
[0880] R C2 If there are multiple instances of R C2 are identical or different from each other,
[0881] R C3 If this plural exists, the plural R C3 They are identical or different from each other,
[0882] L A1 , L A2 , L A3 , L B1 , L B2 , L B3 and L B4 are, each independently
[0883] single bond,
[0884] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[0885] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0886] nb is 1, 2, 3, or 4, and
[0887] If nb is 1, L B5 Is,
[0888] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[0889] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0890] If nb is 2, 3, or 4, multiple L B5 are identical or different from each other,
[0891] If nb is 2, 3, or 4, multiple L B5 Is,
[0892] They combine with each other to form a substituted or unsubstituted single ring,
[0893] They combine with each other to form substituted or unsubstituted condensed rings, or
[0894] Without combining with each other,
[0895] L that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. B5 Is,
[0896] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[0897] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0898] R A35 and R A36 A group consisting of,
[0899] They combine with each other to form a substituted or unsubstituted single ring,
[0900] They combine with each other to form substituted or unsubstituted condensed rings, or
[0901] Without combining with each other,
[0902] R A25 , and R which does not form the above-mentioned substituted or unsubstituted single ring, and also does not form the above-mentioned substituted or unsubstituted condensed ring. A35 and R A36 each independently
[0903] hydrogen atom,
[0904] Cyanogi,
[0905] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0906] Substituted or unsubstituted alkyl halides having 1 to 50 carbon atoms,
[0907] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[0908] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[0909] -O-(R 904 The one indicated by ),
[0910] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0911] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0912] R A20 ~R A24 One or more of the groups consisting of two or more adjacent groups,
[0913] They combine with each other to form a substituted or unsubstituted single ring,
[0914] They combine with each other to form substituted or unsubstituted condensed rings, or
[0915] They do not combine with each other,
[0916] R A30 ~R A34 One or more of the groups consisting of two or more adjacent groups,
[0917] They combine with each other to form a substituted or unsubstituted single ring,
[0918] They combine with each other to form substituted or unsubstituted condensed rings, or
[0919] Without combining with each other,
[0920] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. A20 ~R A24 and R A30 ~R A34are, each independently
[0921] hydrogen atom,
[0922] Cyanogi,
[0923] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0924] Substituted or unsubstituted alkyl halides having 1 to 50 carbon atoms,
[0925] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[0926] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[0927] -O-(R 904 The one indicated by ),
[0928] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0929] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0930] Multiple R A20 They are identical or different from each other,
[0931] Multiple R A30 They are identical or different from each other,
[0932] R in the compounds represented by the above general formulas (cHT2-1), (cHT2-2), and (cHT2-3). 901 ~R 904 are, each independently
[0933] hydrogen atom,
[0934] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0935] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[0936] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0937] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[0938] R 901 In this case, multiple Rs 901 They are identical or different from each other,
[0939] R 902 If there are multiple cases, multiple R 902 are identical or different from each other,
[0940] R 903 In this case, multiple Rs 903 They are identical or different from each other,
[0941] R 904 If there are multiple cases, multiple R 904 are identical or different from each other.
[0942] In one embodiment of the organic EL device of the present embodiment, the first amino group represented by the following general formula (c21) and the second amino group represented by the following general formula (c22) among the compound represented by the general formula (cHT2-3) are the same group or different groups.
[0943] [Chemical Formula 46]
[0944]
[0945] (In the above general formulas (c21) and (c22), * is L respectively B5 It is the connection location with.)
[0946] In one embodiment of the organic EL device of the present embodiment, in the compounds represented by the general formulas (cHT2-1), (cHT2-2), and (cHT2-3), the substituent in the case of "substituted or unsubstituted" is -N(R C6 )(R C7 It is not a device indicated by ).
[0947] In this embodiment, R C6 and R C7Each is independently a hydrogen atom, a substituted or unsubstituted C1-50 alkyl group, a substituted or unsubstituted ring-forming C3-50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-50 aryl group, or a substituted or unsubstituted ring-forming heterocyclic group with 5-50 atoms, and a plurality of R C6 are identical or different from each other, and multiple R C7 They are identical or different from each other.
[0948] In the case of "substituted or non-substituted," the substituent is -N(R C6 )(R C7 If the group represented by ) is not the one, the compounds represented by the above general formulas (cHT2-1) and (cHT2-2) are monoamine compounds.
[0949] In the case of "substituted or non-substituted," the substituent is -N(R C6 )(R C7 If the group represented by ) is not the one represented by ), the compound represented by the above general formula (cHT2-3) is a diamine compound.
[0950] In one embodiment of the organic EL device of the present embodiment, the second anode-side organic layer contains at least one compound selected from the group consisting of the compound represented by the general formula (cHT2-1), the compound represented by the general formula (cHT2-2), and the compound represented by the general formula (cHT2-3), and the third anode-side organic layer contains at least one compound selected from the group consisting of the compound represented by the general formula (cHT3-1), the compound represented by the general formula (cHT3-2), the compound represented by the general formula (cHT3-3), and the compound represented by the general formula (cHT3-4).
[0951] In one embodiment of the organic EL device of the present embodiment, the compound contained in the second anode-side organic layer is a monoamine compound. A monoamine compound is a compound having only one substituted or unsubstituted amino group in its molecule.
[0952] In one embodiment of the organic EL device of the present embodiment, the compound represented by the general formula (cHT2-1) and the compound represented by the general formula (cHT2-2) are monoamine compounds.
[0953] In one embodiment of the organic EL element of the present embodiment, the compound contained in the second anode-side organic layer is a diamine compound having two substituted or unsubstituted amino groups in the molecule.
[0954] In one embodiment of the organic EL device of the present embodiment, the compound represented by the general formula (cHT2-3) is a diamine compound.
[0955] In one embodiment of the organic EL device of the present embodiment, the compound contained in the second anode-side organic layer is a triamine compound having three substituted or unsubstituted amino groups in the molecule.
[0956] In one embodiment of the organic EL device of the present embodiment, the compound contained in the second anode-side organic layer is a tetraamine compound having four substituted or unsubstituted amino groups in the molecule.
[0957] In the case where the compound represented by the above general formulas (cHT2-1) and (cHT2-2) is a triamine compound, the compound represented by the above general formulas (cHT2-1) and (cHT2-2) has -N(R) as a substituent in the case of "substituted or unsubstituted". C6 )(R C7 It has two units indicated by ).
[0958] In the case where the compound represented by the above general formulas (cHT2-1) and (cHT2-2) is a tetraamine compound, the compound represented by the above general formulas (cHT2-1) and (cHT2-2) has -N(R) as a substituent in the case of "substituted or unsubstituted". C6 )(R C7 It has 3 units indicated by ).
[0959] In the case where the compound represented by the above general formula (cHT2-3) is a triamine compound, the compound represented by the above general formula (cHT2-3) has -N(R) as a substituent in the case of "substituted or unsubstituted". C6 )(R C7 It has one energy indicated by ).
[0960] In the case where the compound represented by the above general formula (cHT2-3) is a tetraamine compound, the compound represented by the above general formula (cHT2-3) has -N(R) as a substituent in the case of "substituted or unsubstituted". C6 )(R C7 It has two units indicated by ).
[0961] In one embodiment of the organic EL device of the present embodiment, the compound contained in the second anode-side organic layer has at least one group selected from the group consisting of the group represented by the following general formula (2-a), the group represented by the general formula (2-b), the group represented by the general formula (2-c), the group represented by the general formula (2-d), the group represented by the general formula (2-e), and the group represented by the general formula (2-f).
[0962] In one embodiment of the organic EL device of the present embodiment, the compound contained in the second anode-side organic layer is at least one compound selected from the group consisting of the compound represented by the general formula (cHT2-1), the compound represented by the general formula (cHT2-2), and the compound represented by the general formula (cHT2-3), and also Ar in the general formula (cHT2-1), general formula (cHT2-2), and general formula (cHT2-3). 112 , Ar 113 , Ar 121 , Ar 122 , Ar 123 and Ar 124 At least one of them has at least one type of group selected from the group consisting of the group represented by the following general formula (2-a), the group represented by the general formula (2-b), the group represented by the general formula (2-c), the group represented by the general formula (2-d), the group represented by the general formula (2-e), and the group represented by the general formula (2-f).
[0963] [Chemical Formula 47]
[0964]
[0965] (Among the above general formula (2-a),
[0966] R 251 ~R 255 Among them, groups consisting of two or more adjacent groups do not combine with each other,
[0967] R 251 ~R 255 are, each independently
[0968] hydrogen atoms, or
[0969] It is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and
[0970] ** indicates the connection location.)
[0971] [Chemical Formula 48]
[0972]
[0973] (of the above general formula (2-b),
[0974] R 261 ~R 268 One of them is a single bond that bonds to *b, and
[0975] R that is not a single bond bonding to *b 261 ~R 268 Among them, groups consisting of two or more adjacent elements do not combine with each other,
[0976] R that is not a single bond bonding to *b 261 ~R 268 each independently
[0977] hydrogen atom,
[0978] A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or
[0979] It is a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, and
[0980] ** indicates the connection location.)
[0981] [Chemical Formula 49]
[0982]
[0983] (Among the above general formula (2-c),
[0984] R 271 ~R 282 One of them is a single bond that bonds to *c, and
[0985] R that is not a single bond bonding to *c 271 ~R 282 Among them, groups consisting of two or more adjacent groups do not combine with each other,
[0986] R that is not a single bond bonding to *c 271 ~R 282 are, each independently
[0987] hydrogen atom,
[0988] A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or
[0989] It is a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, and
[0990] ** indicates the connection location.)
[0991] [Chemical Formula 50]
[0992]
[0993] (of the above general formula (2-d),
[0994] R 291 ~R 300 One of them is a single bond that combines with *d, and
[0995] R that is not a single bond bonding to *d 291 ~R 300 Among them, groups consisting of two or more adjacent elements do not combine with each other,
[0996] R that is not a single bond bonding to *d 291 ~R 300 each independently
[0997] hydrogen atom,
[0998] A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or
[0999] It is a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, and
[1000] ** indicates the connection location.)
[1001] [Chemical Formula 51]
[1002]
[1003] (Among the above general formula (2-e),
[1004] Z3 consists of oxygen atoms, sulfur atoms, and NR. 319 or C(R 320 )(R 321 ) and,
[1005] R 311 ~R 321 One of them is a single bond that binds to *e, or R 311 ~R 318One carbon atom of any of the following substituted or unsubstituted benzene rings, formed by the combination of two or more adjacent groups, is bonded to *e by a single bond, and
[1006] R that is not a single bond bonding to *e 311 ~R 318 A group consisting of two or more adjacent members,
[1007] They combine with each other to form substituted or unsubstituted benzene rings, or
[1008] They do not combine with each other,
[1009] R that is not a single bond to *e and also does not form the above-mentioned substituted or unsubstituted benzene ring 311 ~R 318 each independently
[1010] hydrogen atom,
[1011] Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms,
[1012] A substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, or
[1013] It is a complex circulating group with 5 to 10 substituent or unsubstituent ring-forming atoms, and
[1014] R that is not a single bond in *e 319 Is,
[1015] hydrogen atom,
[1016] A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or
[1017] It is a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, and
[1018] R that is not a single bond bonding to *e 320 and R 321 A group consisting of,
[1019] They combine with each other to form a substituted or unsubstituted single ring,
[1020] They combine with each other to form substituted or unsubstituted condensed rings, or
[1021] Without combining with each other,
[1022] R that is not a single bond to *e, does not form the aforementioned substituted or unsubstituted single ring, and does not form the aforementioned substituted or unsubstituted condensed ring. 320 and R 321 each independently
[1023] hydrogen atom,
[1024] A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or
[1025] It is a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, and
[1026] ** indicates the connection location.)
[1027] [Chemical Formula 52]
[1028]
[1029] (Among the above general formula (2-f),
[1030] R 341 ~R 345 One of them is a single bond that binds to *h1, and R 341 ~R 345 The other one is a single bond that bonds to *h2, and
[1031] R that is not a single bond to *h1 and is not a single bond to *h2 341 ~R 345 Among them, groups consisting of two or more adjacent elements do not combine with each other,
[1032] R 351 ~R 355 One or more of the groups consisting of two or more adjacent groups,
[1033] They combine with each other to form a substituted or unsubstituted single ring,
[1034] They combine with each other to form substituted or unsubstituted condensed rings, or
[1035] Without combining with each other,
[1036] R 361 ~R 365 One or more of the groups consisting of two or more adjacent groups,
[1037] They combine with each other to form a substituted or unsubstituted single ring,
[1038] They combine with each other to form substituted or unsubstituted condensed rings, or
[1039] They do not combine with each other,
[1040] R that is not a single bond to *h1 and is not a single bond to *h2 341 ~R 345 , and R which does not form the above-mentioned substituted or unsubstituted single ring, and also does not form the above-mentioned substituted or unsubstituted condensed ring. 351 ~R 355 and R 361 ~R 365 are, each independently
[1041] hydrogen atom,
[1042] A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or
[1043] It is a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, and
[1044] ** indicates the connection location.)
[1045] In one embodiment of the organic EL device of the present embodiment, the group represented by general formula (2-a), the group represented by general formula (2-b), the group represented by general formula (2-c), the group represented by general formula (2-d), the group represented by general formula (2-e), and the group represented by general formula (2-f) each independently bond directly to the nitrogen atom of the amino group of the monoamine compound, bond through a phenylene group, or bond through a biphenylene group.
[1046] In one embodiment of the organic EL device of the present embodiment, the compound contained in the second anode-side organic layer is a compound represented by the general formula (cHT2-1), and also Ar 112 and Ar 113 At least one of them is a group selected from the group consisting of the general formula (2-a), the general formula (2-b), the general formula (2-c), the general formula (2-d), the general formula (2-e), and the general formula (2-f).
[1047] In one embodiment of the organic EL device of the present embodiment, the compound contained in the second anode-side organic layer is a compound represented by the general formula (cHT2-2), and also Ar 112 and Ar 113 At least one of them is a group selected from the group consisting of the general formula (2-a), the general formula (2-b), the general formula (2-c), the general formula (2-d), the general formula (2-e), and the general formula (2-f).
[1048] In one embodiment of the organic EL device of the present embodiment, the compound contained in the second anode-side organic layer is a compound represented by the general formula (cHT2-3), and also Ar 121 , Ar 122 , Ar 123 and Ar 124 At least one of them is a group selected from the group consisting of the general formula (2-a), the general formula (2-b), the general formula (2-c), the general formula (2-d), the general formula (2-e), and the general formula (2-f).
[1049] In the organic EL device of the present embodiment, Z3 is NR 319 In the case of, R 312 or R 317It is preferable that the bond be a single bond that binds to *e.
[1050] In one embodiment of the organic EL device of the present embodiment, the device represented by the general formula (2-e) is the device represented by the following general formula (2-e7).
[1051] [Chemical Formula 53]
[1052]
[1053] (Among the above general formula (2-e7), R 311 ~R 316 , R 318 and R 319 are R in the above general formula (2-e), respectively. 311 ~R 316 , R 318 and R 319 It has the same meaning as, and ** indicates the connection position.)
[1054] In the organic EL device of the present embodiment, Z3 is NR 319 In the case of, R 315 , R 316 or R 318 It is also desirable that the bond be a single bond that binds to *e.
[1055] In one embodiment of the organic EL device of the present embodiment, the group represented by the general formula (2-e) is the group represented by the following general formula (2-e4), general formula (2-e5), or general formula (2-e6).
[1056] [Chemical Formula 54]
[1057]
[1058] (Among the above general formulas (2-e4), (2-e5) and (2-e6), R 311 ~R 319 are R in the above general formula (2-e), respectively. 311 ~R 319 It has the same meaning as, and ** indicates the connection position.)
[1059] In the organic EL device of the present embodiment, the device represented by the general formula (2-e) is a device represented by the following general formula (2-e1), general formula (2-e2), or general formula (2-e3).
[1060] [Chemical Formula 55]
[1061]
[1062] (among the above general formulas (2-e1), (2-e2) and (2-e3),
[1063] Z3 consists of oxygen atoms, sulfur atoms, and NR. 319 or C(R 320 )(R 321 ) and,
[1064] R 311 ~R 325 One of them is a single bond that bonds to *e, and
[1065] R that is not a single bond bonding to *e 311 ~R 318 and R 322 ~R 325 are, each independently
[1066] hydrogen atom,
[1067] Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms,
[1068] A substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, or
[1069] It is a complex circulating group with 5 to 10 substituent or unsubstituent ring-forming atoms, and
[1070] R that is not a single bond bonding to *e 319 Is,
[1071] hydrogen atom,
[1072] A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or
[1073] It is a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, and
[1074] R that is not a single bond bonding to *e 320 and R321 A group consisting of,
[1075] They combine with each other to form a substituted or unsubstituted single ring,
[1076] They combine with each other to form substituted or unsubstituted condensed rings, or
[1077] Without combining with each other,
[1078] R that is not a single bond to *e, does not form the aforementioned substituted or unsubstituted single ring, and does not form the aforementioned substituted or unsubstituted condensed ring. 320 and R 321 each independently
[1079] hydrogen atom,
[1080] A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or
[1081] It is a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, and
[1082] ** indicates the connection location.)
[1083] In one aspect of the organic EL device of the present embodiment, ** among the general formulas (2-a), (2-b), (2-c), (2-d), (2-e), (2-f), (2-e1), (2-e2), (2-e3), (2-e4), (2-e5), (2-e6) and (2-e7) are each independently L A2 , L A3 , L B1 , L B2 , L B3 or L B4 It is a bonding position with or a bonding position with the nitrogen atom of the amino group.
[1084] In one embodiment of the organic EL device of the present embodiment, the compound contained in the second anode-side organic layer is a compound that does not contain a thiophene ring in its molecule.
[1085] In one embodiment of the organic EL device of the present embodiment, the second hole transport band material is at least one compound selected from the group consisting of the compound represented by the general formula (cHT2-1), the compound represented by the general formula (cHT2-2), and the compound represented by the general formula (cHT2-3).
[1086] In one embodiment of the organic EL device of the present embodiment, the second hole transport band material is a monoamine compound, a diamine compound, a triamine compound, or a tetraamine compound.
[1087] In one embodiment of the organic EL device of the present embodiment, the first anode-side organic layer contains a first hole transport band material.
[1088] In one embodiment of the organic EL device of the present embodiment, the first hole transport band material and the third hole transport band material are different compounds.
[1089] In one embodiment of the organic EL device of the present embodiment, the first hole transport band material and the second hole transport band material may be different compounds or identical compounds. When the first hole transport band material and the second hole transport band material are identical compounds, it is preferable that the first anode-side organic layer contains a compound (e.g., a dope compound) having a molecular structure different from that of the first hole transport band material, the second hole transport band material, and the third hole transport band material.
[1090] In one embodiment of the organic EL device of the present embodiment, it is preferable that the first anode-side organic layer contains a first organic material and a second organic material that are different from each other. It is preferable that the content of the second organic material in the first anode-side organic layer is less than 50 mass%, and as the first anode-side organic layer contains the first organic material and the second organic material, the hole injection capability from the anode to the first anode-side organic layer is improved.
[1091] The first organic material contained in the first anode-side organic layer is preferably a first hole transport band material, and the second organic material is preferably a dope compound.
[1092] When the first anode-side organic layer contains a first hole transport band material and a dope compound, the content of the dope compound in the first anode-side organic layer is preferably 0.5 mass% or more and 5 mass% or less, and more preferably 1.0 mass% or more and 3.0 mass% or less. The content of the first hole transport band material in the first anode-side organic layer is preferably 40 mass% or more, more preferably 45 mass% or more, and even more preferably 50 mass% or more. The content of the first hole transport band material in the first anode-side organic layer is preferably 99.5 mass% or less. The total content of the first hole transport band material and the dope compound in the first anode-side organic layer is 100 mass% or less.
[1093] In one embodiment of the organic EL device of the present embodiment, the dope compound is a compound comprising at least one of a first ring structure represented by the following general formula (P11) and a second ring structure represented by the following general formula (P12).
[1094] [Chemical Formula 56]
[1095]
[1096] (The first ring structure represented by the above general formula (P11) condenses with at least one ring structure among a substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 50 carbon atoms and a substituted or unsubstituted ring-forming heterocyclic ring having 5 to 50 atoms in the molecule of the dope compound, and
[1097] =Z 10The structure represented by is denoted by the following general formulas (11a), (11b), (11c), (11d), (11e), (11f), (11g), (11h), (11i), (11j), (11k) or (11m).
[1098] [Chemical Formula 57]
[1099]
[1100] [Chemical Formula 58]
[1101]
[1102] (among the above general formulas (11a), (11b), (11c), (11d), (11e), (11f), (11g), (11h), (11i), (11j), (11k) or (11m), R 11 ~R 14 and R 1101 ~R 1110 each independently
[1103] hydrogen atom,
[1104] Halogen atoms,
[1105] hydroxyl group,
[1106] Cyanogi,
[1107] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1108] Substituted or unsubstituted alkyl halides having 1 to 50 carbon atoms,
[1109] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1110] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[1111] -O-(R 904 The one indicated by ),
[1112] -S-(R 905 The one indicated by ),
[1113] -N(R 906 )(R 907The one indicated by ),
[1114] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1115] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[1116] (In the above general formula (P12), Z1 to Z5 are each independently
[1117] nitrogen atoms,
[1118] R 15 A carbon atom that bonds with, or
[1119] It is a carbon atom that bonds with other atoms in the molecule of the above dope compound, and
[1120] Among Z1 to Z5, at least one is a carbon atom that bonds with another atom in the molecule of the dope compound, and
[1121] R 15 Is,
[1122] hydrogen atom,
[1123] Halogen atoms,
[1124] Cyanogi,
[1125] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1126] Substituted or unsubstituted alkyl halides having 1 to 50 carbon atoms,
[1127] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1128] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
[1129] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms,
[1130] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[1131] -O-(R 904 The one indicated by ),
[1132] -S-(R 905 The one indicated by ),
[1133] -N(R 906 )(R 907 The one indicated by ),
[1134] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[1135] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,
[1136] carboxyl group,
[1137] Substituted or unsubstituted ester group,
[1138] Carvamo Diary of Substitution or Non-substitution,
[1139] Nitro group, and
[1140] Selected from a group consisting of substituted or non-substituted siloksanilgi, and
[1141] R 15 If there are multiple instances of R 15 are identical or different from each other.
[1142] (among the above dope compounds, R 901 ~R 907 each independently
[1143] hydrogen atom,
[1144] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1145] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1146] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1147] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[1148] R 901 In this case, multiple Rs 901 They are identical or different from each other,
[1149] R 902If there are multiple cases, multiple R 902 are identical or different from each other,
[1150] R 903 In this case, multiple Rs 903 They are identical or different from each other,
[1151] R 904 If there are multiple cases, multiple R 904 are identical or different from each other,
[1152] R 905 If there are multiple cases, multiple R 905 are identical or different from each other,
[1153] R 906 In this case, multiple Rs 906 They are identical or different from each other,
[1154] R 907 In this case, multiple Rs 907 They are identical or different from each other.
[1155] The ester group in this specification is at least one group selected from the group consisting of alkyl ester groups and aryl ester groups.
[1156] The alkyl ester group in this specification is, for example, -C(=O)OR E It is indicated as. R E is, for example, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 10 carbon atoms).
[1157] The aryl ester group in this specification is, for example, -C(=O)OR Ar It is indicated as. R Ar It is, for example, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms.
[1158] The siloxanyl group in this specification is a silicon compound group formed through an ether bond, such as a trimethylsiloxanyl group.
[1159] In this specification, the carbamoyl group is represented as -CONH2.
[1160] The carbamoyl group of the substitution in this specification is, for example, -CONH-Ar C , or -CONH-R C It is displayed as. Ar C is, for example, at least one group selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 50 carbon atoms (preferably 6 to 10 carbon atoms) and a heterocyclic group having 5 to 50 atoms (preferably 5 to 14 atoms). Ar C The contribution of a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms combined with a substituted or unsubstituted ring-forming complex circulator having 5 to 50 atoms is also good.
[1161] R C is, for example, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 6 carbon atoms).
[1162] In the above dope compound, it is preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.
[1163] (Specific examples of dope compounds)
[1164] Specific examples of dope compounds include, for instance, the following compounds. However, the present invention is not limited to these specific examples of dope compounds.
[1165] [Chemical Formula 59]
[1166]
[1167] [Chemical Formula 60]
[1168]
[1169] [Chemical Formula 61]
[1170]
[1171] [Chemical Formula 62]
[1172]
[1173] [Chemical Formula 63]
[1174]
[1175] [Chemical Formula 64]
[1176]
[1177] [Chemical Formula 65]
[1178]
[1179] [Chemical Formula 66]
[1180]
[1181] [Chemical Formula 67]
[1182]
[1183] [Chemical Formula 68]
[1184]
[1185] [Chemical Formula 69]
[1186]
[1187] [Chemical Formula 70]
[1188]
[1189] [Chemical Formula 71]
[1190]
[1191] [Chemical Formula 72]
[1192]
[1193] [Chemical Formula 73]
[1194]
[1195] [Chemical Formula 74]
[1196]
[1197] [Chemical Formula 75]
[1198]
[1199] [Chemical Formula 76]
[1200]
[1201] [Chemical Formula 77]
[1202]
[1203] [Chemical Formula 78]
[1204]
[1205] [Chemical Formula 79]
[1206]
[1207] [Chemical Formula 80]
[1208]
[1209] [Chemical Formula 81]
[1210]
[1211] [Chemical Formula 82]
[1212]
[1213] [Chemical Formula 83]
[1214]
[1215] [Chemical Formula 84]
[1216]
[1217] [Chemical Formula 85]
[1218]
[1219] [Chemical Formula 86]
[1220]
[1221] [Chemical Formula 87]
[1222]
[1223] [Chemical Formula 88]
[1224]
[1225] [Chemical Formula 89]
[1226]
[1227] [Chemical Formula 90]
[1228]
[1229] [Chemical Formula 91]
[1230]
[1231] [Chemical Formula 92]
[1232]
[1233] [Chemical Formula 93]
[1234]
[1235] [Chemical Formula 94]
[1236]
[1237] [Chemical Formula 95]
[1238]
[1239] [Chemical Formula 96]
[1240]
[1241] [Chemical Formula 97]
[1242]
[1243] [Chemical Formula 98]
[1244]
[1245] [Chemical Formula 99]
[1246]
[1247] [Chemical Formula 100]
[1248]
[1249] ][Chemical Formula 101]
[1250]
[1251] [Chemical Formula 102]
[1252]
[1253] [Chemical Formula 103]
[1254]
[1255] [Chemical Formula 104]
[1256]
[1257] In one embodiment of the organic EL device of the present embodiment, the third anode-side organic layer and the light-emitting region are in direct contact.
[1258] In one embodiment of the organic EL device of the present embodiment, the second anode-side organic layer and the third anode-side organic layer are in direct contact.
[1259] In one embodiment of the organic EL device of the present embodiment, the anode and the first anode-side organic layer are in direct contact.
[1260] In one embodiment of the organic EL device of the present embodiment, the organic EL device further has a fourth anode-side organic layer, and the fourth anode-side organic layer is disposed between the third anode-side organic layer and the light-emitting region.
[1261] In one embodiment of the organic EL device of the present embodiment, the fourth anode-side organic layer and the light-emitting region are in direct contact.
[1262] In one embodiment of the organic EL device of the present embodiment, the fourth anode-side organic layer and the third anode-side organic layer are in direct contact.
[1263] In one embodiment of the organic EL device of the present embodiment, the first anode-side organic layer, the second anode-side organic layer, the third anode-side organic layer, and the fourth anode-side organic layer are arranged in this order from the anode side.
[1264] In one embodiment of the organic EL device of the present embodiment, the fourth anode-side organic layer is a barrier layer. For example, when a barrier layer is disposed on the anode side of the light-emitting layer, the barrier layer transports holes and also prevents electrons from reaching each organic layer of the hole transport band disposed on the anode side of the barrier layer. Additionally, a barrier layer directly in contact with the light-emitting layer may be installed to prevent excitation energy from leaking from the light-emitting layer to its surrounding layer. The barrier layer disposed on the anode side of the light-emitting layer prevents excitons generated in the light-emitting layer from moving to each organic layer of the hole transport band. It is preferable that the light-emitting layer and the barrier layer are in direct contact.
[1265] In one embodiment of the organic EL device of the present embodiment, the film thickness of the fourth anode-side organic layer is thinner than the film thickness of the third anode-side organic layer.
[1266] In one embodiment of the organic EL device of the present embodiment, the film thickness of the fourth anode-side organic layer is 20 nm or less.
[1267] In one embodiment of the organic EL device of the present embodiment, the film thickness of the fourth anode-side organic layer is 5 nm or more.
[1268] The organic EL device of the present embodiment is thought to have a long lifespan by having a fourth anode-side organic layer (preferably an electron barrier layer) with a film thickness smaller than that of the third anode-side organic layer.
[1269] In one embodiment of the organic EL device of the present embodiment, the sum of the film thickness of the first anode-side organic layer, the film thickness of the second anode-side organic layer, the film thickness of the third anode-side organic layer, and the film thickness of the fourth anode-side organic layer is 150 nm or less.
[1270] In one embodiment of the organic EL device of the present embodiment, the fourth anode-side organic layer contains a fourth hole transport band material. The compound contained in the fourth anode-side organic layer may be referred to as the fourth hole transport band material.
[1271] In one embodiment of the organic EL device of the present embodiment, the fourth hole transport band material and the third hole transport band material are different compounds.
[1272] In one embodiment of the organic EL device of the present embodiment, the fourth hole transport band material, the third hole transport band material, and the second hole transport band material are different compounds.
[1273] In one embodiment of the organic EL device of the present embodiment, the fourth anode-side organic layer contains a compound represented by the general formula (C1) or a compound represented by the general formula (C2).
[1274] In one embodiment of the organic EL device of the present embodiment, the third anode-side organic layer and the fourth anode-side organic layer may both contain a compound represented by the general formula (C1), but the compound contained in the third anode-side organic layer and the compound contained in the fourth anode-side organic layer have different molecular structures.
[1275] In one embodiment of the organic EL device of the present embodiment, the fourth hole transport band material is a monoamine compound, a diamine compound, a triamine compound, or a tetraamine compound.
[1276] In one embodiment of the organic EL device of the present embodiment, the fourth hole transport band material is at least one compound selected from the group consisting of the compound represented by the general formula (cHT3-1), the compound represented by the general formula (cHT3-2), the compound represented by the general formula (cHT3-3), and the compound represented by the general formula (cHT3-4).
[1277] In one embodiment of the organic EL device of the present embodiment, the first anode-side organic layer, the second anode-side organic layer, the third anode-side organic layer, and the fourth anode-side organic layer each include one or more different compounds.
[1278] In one embodiment of the organic EL device of the present embodiment, the first anode-side organic layer, the second anode-side organic layer, the third anode-side organic layer, and the fourth anode-side organic layer contain a monoamine compound having only one substituted or unsubstituted amino group in the molecule.
[1279] In one embodiment of the organic EL device of the present embodiment, the first anode-side organic layer, the second anode-side organic layer, the third anode-side organic layer, and the fourth anode-side organic layer do not contain a diamine compound. A diamine compound is a compound having two substituted or unsubstituted amino groups in its molecule.
[1280] The compound represented by the above general formula (C1) is preferably a monoamine compound.
[1281] In one embodiment of the organic EL device of the present embodiment, at least one of the first anode-side organic layer, the second anode-side organic layer, the third anode-side organic layer, and the fourth anode-side organic layer may contain a diamine compound. The compound represented by the general formula (C2) is preferably a diamine compound.
[1282] In the organic EL device according to the present embodiment, R in the compound containing the hole transport band 901 , R 902 , R 903 and R 904 are, each independently
[1283] hydrogen atom,
[1284] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1285] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1286] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1287] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[1288] R 901If this plural exists, the plural R 901 They are identical or different from each other,
[1289] R 902 If there are multiple instances of R 902 are identical or different from each other,
[1290] R 903 If this plural exists, the plural R 903 They are identical or different from each other,
[1291] R 904 If there are multiple instances of R 904 They are identical or different from each other.
[1292] In this embodiment, it is preferable that all groups described as "substituted or non-substituted" are "non-substituted" groups.
[1293] In this embodiment, the first hole transport band material, the second hole transport band material, the third hole transport band material, and the fourth hole transport band material may be referred to as the hole transport band material.
[1294] In the organic EL device according to the present embodiment, the hole transport band material may be a compound containing a substituted or unsubstituted 3-carbazolyl group in its molecule. Additionally, in the organic EL device according to the present embodiment, the hole transport band material may be a compound that does not contain a substituted or unsubstituted 3-carbazolyl group in its molecule.
[1295] (Method for manufacturing hole transport band materials)
[1296] The hole transport band material according to the present embodiment can be manufactured by a known method, or by using a known alternative reaction and raw material suited to the target object according to the above method.
[1297] (Specific example of a hole transport band material)
[1298] Specific examples of the hole transport band material according to the present embodiment include, for instance, the following compounds. However, the present invention is not limited to these specific examples.
[1299] [Chemical Formula 105]
[1300]
[1301] [Chemical Formula 106]
[1302]
[1303] [Chemical Formula 107]
[1304]
[1305] [Chemical Formula 108]
[1306]
[1307] [Chemical Formula 109]
[1308]
[1309] [Chemical Formula 110]
[1310]
[1311] [Chemical Formula 111]
[1312]
[1313] [Chemical Formula 112]
[1314]
[1315] [Chemical Formula 113]
[1316]
[1317] [Chemical Formula 114]
[1318]
[1319] [Chemical Formula 115]
[1320]
[1321] [Chemical Formula 116]
[1322]
[1323] [Chemical Formula 117]
[1324]
[1325] [Chemical Formula 118]
[1326]
[1327] [Chemical Formula 119]
[1328]
[1329] [Chemical Formula 120]
[1330]
[1331] [Chemical Formula 121]
[1332]
[1333] [Chemical Formula 122]
[1334]
[1335] [Chemical Formula 123]
[1336]
[1337] [Chemical Formula 124]
[1338]
[1339] [Chemical Formula 125]
[1340]
[1341] [Chemical Formula 126]
[1342]
[1343] [Chemical Formula 127]
[1344]
[1345] [Chemical Formula 128]
[1346]
[1347] [Chemical Formula 129]
[1348]
[1349] [Chemical Formula 130]
[1350]
[1351] [Chemical Formula 131]
[1352]
[1353] [Chemical Formula 132]
[1354]
[1355] [Chemical Formula 133]
[1356]
[1357] [Chemical Formula 134]
[1358]
[1359] [Chemical Formula 135]
[1360]
[1361] [Chemical Formula 136]
[1362]
[1363] [Chemical Formula 137]
[1364]
[1365] [Chemical Formula 138]
[1366]
[1367] [Chemical Formula 139]
[1368]
[1369] [Chemical Formula 140]
[1370]
[1371] [Chemical Formula 141]
[1372]
[1373] [Chemical Formula 142]
[1374]
[1375] [Chemical Formula 143]
[1376]
[1377] [Chemical Formula 144]
[1378]
[1379] [Chemical Formula 145]
[1380]
[1381] [Chemical Formula 146]
[1382]
[1383] [Chemical Formula 147]
[1384]
[1385] [Chemical Formula 148]
[1386]
[1387] [Chemical Formula 149]
[1388]
[1389] [Chemical Formula 150]
[1390]
[1391] [Chemical Formula 151]
[1392]
[1393] [Chemical Formula 152]
[1394]
[1395] [Chemical Formula 153]
[1396]
[1397] [Chemical Formula 154]
[1398]
[1399] [Chemical Formula 155]
[1400]
[1401] [Chemical Formula 156]
[1402]
[1403] [Chemical Formula 157]
[1404]
[1405] [Chemical Formula 158]
[1406]
[1407] [Chemical Formula 159]
[1408]
[1409] [Chemical Formula 160]
[1410]
[1411] [Chemical Formula 161]
[1412]
[1413] [Chemical Formula 162]
[1414]
[1415] [Chemical Formula 163]
[1416]
[1417] [Chemical Formula 164]
[1418]
[1419] [Chemical Formula 165]
[1420]
[1421] [Chemical Formula 166]
[1422]
[1423] [Chemical Formula 167]
[1424]
[1425] [Chemical Formula 168]
[1426]
[1427] [Chemical Formula 169]
[1428]
[1429] [Chemical Formula 170]
[1430]
[1431] [Chemical Formula 171]
[1432]
[1433] [Chemical Formula 172]
[1434]
[1435] [Chemical Formula 173]
[1436]
[1437] [Chemical Formula 174]
[1438]
[1439] [Chemical Formula 175]
[1440]
[1441] [Chemical Formula 176]
[1442]
[1443] [Chemical Formula 177]
[1444]
[1445] [Chemical Formula 178]
[1446]
[1447] [Chemical Formula 179]
[1448]
[1449] [Chemical Formula 180]
[1450]
[1451] [Chemical Formula 181]
[1452]
[1453] [Chemical Formula 182]
[1454]
[1455] [Chemical Formula 183]
[1456]
[1457] [Chemical Formula 184]
[1458]
[1459] [Chemical Formula 185]
[1460]
[1461] [Chemical Formula 186]
[1462]
[1463] [Chemical Formula 187]
[1464]
[1465] [Chemical Formula 188]
[1466]
[1467] [Chemical Formula 189]
[1468]
[1469] [Chemical Formula 190]
[1470]
[1471] [Chemical Formula 191]
[1472]
[1473] [Chemical Formula 192]
[1474]
[1475] [Chemical Formula 193]
[1476]
[1477] [Chemical Formula 194]
[1478]
[1479] [Chemical Formula 195]
[1480]
[1481] [Chemical Formula 196]
[1482]
[1483] [Chemical Formula 197]
[1484]
[1485] [Chemical Formula 198]
[1486]
[1487] [Chemical Formula 199]
[1488]
[1489] [Chemical Formula 200]
[1490]
[1491] [Chemical Formula 201]
[1492]
[1493] [Chemical Formula 202]
[1494]
[1495] [Chemical Formula 203]
[1496]
[1497] [Chemical Formula 204]
[1498]
[1499] [Chemical Formula 205]
[1500]
[1501] [Chemical Formula 206]
[1502]
[1503] [Chemical Formula 207]
[1504]
[1505] [Chemical Formula 208]
[1506]
[1507] [Chemical Formula 209]
[1508]
[1509] [Chemical Formula 210]
[1510]
[1511] [Chemical Formula 211]
[1512]
[1513] [Chemical Formula 212]
[1514]
[1515] [Chemical Formula 213]
[1516]
[1517] [Chemical Formula 214]
[1518]
[1519] [Chemical Formula 215]
[1520]
[1521] [Chemical Formula 216]
[1522]
[1523] [Chemical Formula 217]
[1524]
[1525] [Chemical Formula 218]
[1526]
[1527] [Chemical Formula 219]
[1528]
[1529] [Chemical Formula 220]
[1530]
[1531] [Chemical Formula 221]
[1532]
[1533] [Chemical Formula 222]
[1534]
[1535] [Chemical Formula 223]
[1536]
[1537] [Chemical Formula 224]
[1538]
[1539] [Chemical Formula 225]
[1540]
[1541] [Chemical Formula 226]
[1542]
[1543] [Chemical Formula 227]
[1544]
[1545] [Chemical Formula 228]
[1546]
[1547] [Chemical Formula 229]
[1548]
[1549] (Examples of compounds contained in the second anode-side organic layer)
[1550] In one embodiment of the organic EL device of the present embodiment, the compound contained in the second anode-side organic layer is preferably at least one compound selected from the group of compounds listed below.
[1551] [Chemical Formula 230]
[1552]
[1553] [Chemical Formula 231]
[1554]
[1555] (Examples of compounds contained in the third anode-side organic layer)
[1556] In one embodiment of the organic EL device of the present embodiment, the compound contained in the third anode-side organic layer is preferably at least one compound selected from the group of compounds listed below.
[1557] [Chemical Formula 232]
[1558]
[1559] (Luminous area)
[1560] The light-emitting region includes at least one light-emitting layer.
[1561] In the organic EL device according to the present embodiment, it is preferable that the light-emitting region contains a fluorescent light-emitting material and an organic compound. It is also preferable that the fluorescent light-emitting material contained in the light-emitting region is a fluorescent light-emitting compound described later. It is also preferable that the organic compound contained in the light-emitting region is a host material described later.
[1562] In one embodiment of the organic EL device of the present embodiment, the light-emitting region includes one light-emitting layer.
[1563] In one embodiment of the organic EL device of the present embodiment, the light-emitting region consists of only one light-emitting layer.
[1564] In one embodiment of the organic EL device of the present embodiment, the light-emitting region includes a first light-emitting layer and a second light-emitting layer as two light-emitting layers.
[1565] In one embodiment of the organic EL device of the present embodiment, the light-emitting region consists of only two light-emitting layers.
[1566] In the organic EL device according to the present embodiment, it is preferable that the light-emitting layer contains a light-emitting compound. The light-emitting compound is not particularly limited, but may contain at least one light-emitting compound selected from the group consisting of the first light-emitting compound and the second light-emitting compound described below, for example. In the organic EL device according to the present embodiment, it is preferable that the light-emitting layer contains the light-emitting compound in an amount of 0.5 mass% or more of the total mass of the light-emitting layer. It is preferable that the light-emitting layer contains the light-emitting compound in an amount of 10 mass% or less of the total mass of the light-emitting layer, more preferable that it contains 7 mass% or less of the total mass of the light-emitting layer, and even more preferable that it contains 5 mass% or less of the total mass of the light-emitting layer.
[1567] In one embodiment of the organic EL device of the present embodiment, at least one light-emitting layer in the light-emitting region contains a light-emitting compound that exhibits light emission with a maximum peak wavelength of 500 nm or less. In one embodiment of the organic EL device of the present embodiment, the maximum peak wavelength of light emission exhibited by the light-emitting compound is 480 nm or less. In one embodiment of the organic EL device of the present embodiment, the maximum peak wavelength of light emission exhibited by the light-emitting compound is 430 nm or more and 480 nm or less.
[1568] In one embodiment of the organic EL device of the present embodiment, at least one light-emitting layer in the light-emitting region contains a light-emitting compound that exhibits fluorescent light emission with a maximum peak wavelength of 500 nm or less. In one embodiment of the organic EL device of the present embodiment, the maximum peak wavelength of the fluorescent light emission exhibited by the light-emitting compound is 480 nm or less. In one embodiment of the organic EL device of the present embodiment, the maximum peak wavelength of the fluorescent light emission exhibited by the light-emitting compound is 430 nm or more and 480 nm or less.
[1569] In the organic EL device according to the present embodiment, it is also preferable that the light-emitting region has at least a first light-emitting layer containing a first host material and a second light-emitting layer containing a second host material. The first host material and the second host material are different from each other.
[1570] In the present specification, the “host material” is a material that is included, for example, in “50 mass% or more of the layer.” Accordingly, for example, the first light-emitting layer contains the first host material in 50 mass% or more of the total mass of the first light-emitting layer. Also, for example, the second light-emitting layer contains the second host material in 50 mass% or more of the total mass of the second light-emitting layer. Additionally, for example, the “host material” may be included in 60 mass% or more of the layer, 70 mass% or more of the layer, 80 mass% or more of the layer, 90 mass% or more of the layer, or 95 mass% or more of the layer.
[1571] It is desirable that the triplet energy T1 (H1) of the first host material and the triplet energy T1 (H2) of the second host material satisfy the relationship of the following formula (Equation 1).
[1572] T1(H1) > T1(H2) … (Equation 1)
[1573] In the organic EL device according to the present embodiment, it is preferable that the triplet energy T1 (H1) of the first host material and the triplet energy T1 (H2) of the second host material satisfy the relationship of the following formula (Equation 5).
[1574] T1(H1) - T1(H2) > 0.03 eV … (Equation 5)
[1575] The organic EL device according to the present embodiment can improve the luminous efficiency of the device when it has a first light-emitting layer and a second light-emitting layer that satisfy the relationship of the above formula (Equation 1).
[1576] Conventionally, Triplet-Triplet-Annhilation (sometimes referred to as TTA) is known as a technique for improving the luminescence efficiency of organic electroluminescence devices. TTA is a mechanism in which triplet excitons collide to generate singlet excitons. Additionally, the TTA mechanism is sometimes referred to as the TTF mechanism, as described in International Publication No. 2010 / 134350.
[1577] The TTF phenomenon is explained. Holes injected from the anode and electrons injected from the cathode recombine within the emissive layer to generate excitons. As is conventionally known, the spin states consist of 25% singlet excitons and 75% triplet excitons. In conventional fluorescent devices, light is emitted when 25% of the singlet excitons relax to the ground state, but the remaining 75% of the triplet excitons do not emit light and return to the ground state through a thermal deactivation process. Therefore, the theoretical limit of the internal quantum efficiency of conventional fluorescent devices is stated to be 25%.
[1578] Meanwhile, the behavior of triplet excitons generated within organic matter is being theoretically investigated. According to the literature [SM Bachilo et al., J. Phys. Chem. A, 104, 7711(2000)], assuming that higher-order excitons such as pentatons immediately revert to triplets, triplet excitons (hereinafter, 3 When the density of (represented as A*) increases, triplet excitons collide with each other, and a reaction as shown in the following equation occurs. Here, 1 A represents the ground state, and 1 A* represents the lowest excitation singlet exciton.
[1579] 3 A*+ 3 A*→(4 / 9) 1 A+(1 / 9) 1 A*+(13 / 9) 3 A*
[1580] That is, 5 3 A*→4 1It is predicted that A+1A*, and that 1 / 5, or 20%, of the 75% of triplet excitons initially generated will be converted into singlet excitons. Therefore, the singlet excitons contributing as light are said to be 40%, which is the sum of 25% of the initially generated singlet excitons plus 75% × (1 / 5) = 15%. At this time, the proportion of TTF-derived light (TTF ratio) in the total light intensity is 15 / 40, or 37.5%. Furthermore, if the 75% of triplet excitons initially generated collide with each other to generate singlet excitons (one singlet exciton is generated from two triplet excitons), a very high internal quantum efficiency of 62.5% can be obtained, which is the sum of 25% of the initially generated singlet excitons plus 75% × (1 / 2) = 37.5%. At this time, the TTF ratio is 37.5 / 62.5=60%.
[1581] In the case where the light-emitting region of the organic EL device according to the present embodiment has at least two light-emitting layers (i.e., a first light-emitting layer and a second light-emitting layer) and the triplet energy T1 (H1) of the first host material in the first light-emitting layer and the triplet energy T1 (H2) of the second host material in the second light-emitting layer satisfy the relationship of the above formula (Equation 1), it is thought that triplet excitons generated by the recombination of holes and electrons in the first light-emitting layer are difficult to quench even if there is an excess of carriers at the interface between the first light-emitting layer and the organic layer that is in direct contact with the first light-emitting layer. For example, if the recombination region exists locally at the interface between the first light-emitting layer and the hole transport layer or the electron barrier layer, quenching by excess electrons can be considered. On the other hand, if the recombination region exists locally at the interface between the first light-emitting layer and the electron transport layer or the hole barrier layer, quenching by excess holes can be considered.
[1582] By providing a first light-emitting layer and a second light-emitting layer to satisfy the relationship of the above formula (Mathematical Formula 1), triplet excitons generated in the first light-emitting layer move to the second light-emitting layer without being quenched by excess carriers, and also suppress reverse movement from the second light-emitting layer to the first light-emitting layer. As a result, in the second light-emitting layer, the TTF mechanism is expressed, singlet excitons are efficiently generated, and the light-emitting efficiency is improved.
[1583] In this way, the organic EL device according to the present embodiment has a first light-emitting layer that mainly generates triplet excitons and a second light-emitting layer that mainly expresses a TTF mechanism by utilizing triplet excitons moved from the first light-emitting layer as different regions, and as a second host material in the second light-emitting layer, a compound having a triplet energy smaller than that of the first host material in the first light-emitting layer is used to set a difference in triplet energy, thereby improving the light-emitting efficiency.
[1584] In the organic EL device according to the present embodiment, it is preferable that the first light-emitting layer is disposed between the anode and the cathode, and the second light-emitting layer is disposed between the first light-emitting layer and the cathode. From the anode side, the first light-emitting layer and the second light-emitting layer may be arranged in this order, or from the anode side, the second light-emitting layer and the first light-emitting layer may be arranged in this order. In either case, by selecting a combination of materials that satisfies the relationship of the above formula (Equation 1), the effect of the light-emitting layer being a stacked configuration can be expected.
[1585] In the organic EL device according to the present embodiment, it is also preferable that the first light-emitting layer is positioned on the positive side rather than the second light-emitting layer.
[1586] In the organic EL device according to the present embodiment, when the first light-emitting layer is positioned on the anode side rather than the second light-emitting layer, it is preferable that the first light-emitting layer is in direct contact with the hole transport band. When the hole transport band does not have a fourth anode-side organic layer, it is preferable that the first light-emitting layer and the third anode-side organic layer are in direct contact. When the hole transport band has a fourth anode-side organic layer, it is preferable that the first light-emitting layer and the fourth anode-side organic layer are in direct contact.
[1587] In the organic EL device according to the present embodiment, it is also preferable that the first light-emitting layer and the second light-emitting layer are in direct contact.
[1588] In the present specification, the layer structure in which “the first light-emitting layer and the second light-emitting layer are in direct contact” may include, for example, any one of the following embodiments (LS1), (LS2) and (LS3).
[1589] (LS1) A region in which both the first host material and the second host material are mixed is formed during the process of depositing a compound according to the first light-emitting layer and depositing a compound according to the second light-emitting layer, and the region exists at the interface between the first light-emitting layer and the second light-emitting layer.
[1590] (LS2) A mode in which, when the first light-emitting layer and the second light-emitting layer include a light-emitting compound, a region in which the first host material, the second host material, and the light-emitting compound are mixed is formed during the process of the deposition process of the compound according to the first light-emitting layer and the deposition process of the compound according to the second light-emitting layer, and the region is present at the interface between the first light-emitting layer and the second light-emitting layer.
[1591] (LS3) A mode in which, when the first light-emitting layer and the second light-emitting layer include a light-emitting compound, a region formed of the light-emitting compound, a region formed of the first host material, or a region formed of the second host material is formed during the process of the deposition process of the compound according to the first light-emitting layer and the deposition process of the compound according to the second light-emitting layer, and the region is present at the interface between the first light-emitting layer and the second light-emitting layer.
[1592] (1st light-emitting layer)
[1593] The first light-emitting layer comprises a first host material. The first host material is a compound different from the second host material contained in the second light-emitting layer.
[1594] The first emitting layer preferably comprises a first emitting compound. The first emitting compound is not particularly limited. The first emitting compound is preferably a compound exhibiting luminescence with a maximum peak wavelength of 500 nm or less, more preferably a compound exhibiting luminescence with a maximum peak wavelength of 480 nm or less, and even more preferably a compound exhibiting luminescence with a maximum peak wavelength of 430 nm or more and 480 nm or less. The first emitting compound is preferably a fluorescent emitting compound exhibiting fluorescent luminescence with a maximum peak wavelength of 500 nm or less, more preferably a fluorescent emitting compound exhibiting fluorescent luminescence with a maximum peak wavelength of 480 nm or less, and even more preferably a fluorescent emitting compound exhibiting fluorescent luminescence with a maximum peak wavelength of 430 nm or more and 480 nm or less.
[1595] In the organic EL device according to the present embodiment, the first luminescent compound is preferably a compound that does not contain a zygos ring structure in its molecule.
[1596] In the organic EL device according to the present embodiment, it is preferable that the first luminescent compound is not a boron-containing complex, and it is more preferable that the first luminescent compound is not a complex.
[1597] As a fluorescently emitting compound that emits blue light and can be used in the first light-emitting layer, a compound selected from the group consisting of, for example, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, and triarylamine derivatives may be used.
[1598] In this specification, blue light emission refers to light emission in which the maximum peak wavelength of the emission spectrum is within the range of 430 nm or more and 500 nm or less.
[1599] In the organic EL device according to the present embodiment, it is preferable that the first light-emitting layer does not contain a metal complex. In addition, in the organic EL device according to the present embodiment, it is also preferable that the first light-emitting layer does not contain a boron-containing complex.
[1600] In the organic EL device according to the present embodiment, it is preferable that the first light-emitting layer does not include a phosphorescent light-emitting material (dopant material).
[1601] In addition, it is preferable that the first light-emitting layer does not include heavy metal complexes and phosphorescent rare earth metal complexes. Here, examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.
[1602] The method for measuring the maximum peak wavelength of a compound is as follows. A 5 μmol / L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the emission spectrum of the sample (vertical axis: emission intensity, horizontal axis: wavelength) is measured at room temperature (300 K). The emission spectrum can be measured using a spectrofluorescence photometer manufactured by Hitachi High-Tech Science Co., Ltd. (device name: F-7000). Furthermore, the emission spectrum measuring device is not limited to the device used herein.
[1603] In the emission spectrum, the peak wavelength of the emission spectrum where the emission intensity is maximum is defined as the maximum peak wavelength. Additionally, in this specification, the maximum peak wavelength of fluorescence emission may be referred to as the fluorescence emission maximum peak wavelength (FL-peak).
[1604] In the emission spectrum of the first luminescent compound, the peak at which the emission intensity is maximum is set as the maximum peak, and when the height of the maximum peak is set to 1, it is preferable that the height of other peaks appearing in the emission spectrum is less than 0.6. In addition, the peaks in the emission spectrum are set to maximum values.
[1605] In addition, it is preferable that the number of peaks in the emission spectrum of the first luminescent compound is less than 3.
[1606] In the organic EL device according to the present embodiment, it is preferable that the singlet energy S1 (H1) of the first host material and the singlet energy S1 (D1) of the first luminescent compound satisfy the relationship of the following formula (Equation 20).
[1607] S1(H1) > S1(D1) … (Equation 20)
[1608] Singlet energy S1 refers to the energy difference between the lowest excited singlet state and the ground state.
[1609] By satisfying the relationship of the first host material and the first luminescent compound in the formula (Equation 20), the singlet excitons generated on the first host material become more likely to transfer energy from the first host material to the first luminescent compound, thereby contributing to the fluorescent emission of the first luminescent compound.
[1610] In the organic EL device according to the present embodiment, it is desirable that the triplet energy T1 (H1) of the first host material and the triplet energy T1 (D1) of the first luminescent compound satisfy the relationship of the following formula (Equation 20A).
[1611] T1(D1) > T1(H1) … (Equation 20A)
[1612] As the first host material and the first luminescent compound satisfy the relationship of Equation (Equation 20A), the triplet excitons generated within the first luminescent layer move on the first host material phase rather than the first luminescent compound having a higher triplet energy, making it easier for them to move to the second luminescent layer.
[1613] The organic EL device according to the present embodiment preferably satisfies the relationship of the following formula (Equation 20B).
[1614] T1(D1) > T1(H1) > T1(H2) … (Equation 20B)
[1615] (Triplet energy T1)
[1616] The following methods can be used to measure the triplet energy T1.
[1617] The compound to be measured in EPA (diethyl ether:isopentane:ethanol = 5:5:2 (volume ratio)), 10 -5 mol / L or more 10 -4 A solution is prepared by dissolving to a concentration of mol / L or less, and this solution is placed in a quartz cell to serve as the measurement sample. For this measurement sample, the phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) is measured at a low temperature (77 K). A tangent line is drawn along the rising short-wavelength side of the phosphorescence spectrum, and the wavelength value λ at the intersection of the tangent line and the horizontal axis is... edge Based on [nm], the amount of energy calculated from the following conversion formula (F1) is called the triplet energy T1.
[1618] Conversion formula (F1): T1[eV]=1239.85 / λ edge
[1619] The tangent line for the rise on the short-wavelength side of the phosphorescence spectrum is drawn as follows. When moving along the spectrum curve from the short-wavelength side of the phosphorescence spectrum to the shortest maximum value among the maximum values of the spectrum, the tangent line at each point on the curve toward the long-wavelength side is considered. As the curve rises (i.e., as the vertical axis increases), the slope of this tangent line increases. The tangent line drawn at the point where this slope takes a maximum value (i.e., the tangent line at the inflection point) is designated as the tangent line for the rise on the short-wavelength side of the phosphorescence spectrum.
[1620] In addition, the maximum point having a peak intensity of 15% or less of the maximum peak intensity of the spectrum is not included in the maximum value on the shortest wavelength side mentioned above, and the tangent line drawn from the point where the slope value closest to the maximum value on the shortest wavelength side takes a maximum value is the tangent line for the rise on the short wavelength side of the phosphorescent spectrum.
[1621] For the measurement of phosphorescence, the main body of the F-7000 spectrofluorescence photometer manufactured by Hitachi High-Tech Science Inc. or the main body of the F-4500 spectrofluorescence photometer manufactured by Hitachi High-Tech Inc. may be used. In addition, the measuring device is not limited thereto, and measurement may be performed by combining a cooling device, a low-temperature container, an excitation light source, and a light receiving device.
[1622] (Singlet energy S1)
[1623] The following methods can be used as methods for measuring the singlet energy S1 using a solution (sometimes called the solution method).
[1624] 10 of the compound to be measured -5 mol / L or more 10 -4 Prepare a toluene solution with a mol / L or lower content, place it in a quartz cell, and measure the absorption spectrum of the sample at room temperature (300 K) (vertical axis: absorption intensity, horizontal axis: wavelength). Draw a tangent line to the descent on the long-wavelength side of this absorption spectrum, and the wavelength value λ at the intersection of the tangent line and the horizontal axis.edge The singlet energy is calculated by substituting [nm] into the conversion formula (F2) shown below.
[1625] Conversion formula (F2): S1[eV]=1239.85 / λ edge
[1626] As an absorption spectrum measuring device, for example, a spectrophotometer manufactured by Hitachi (device name: U3310) can be cited, but is not limited to this.
[1627] The tangent line for the descent on the long-wavelength side of the absorption spectrum is drawn as follows. Consider the tangent line at each point on the spectrum curve when moving along the long-wavelength direction from the maximum value on the longest wavelength side among the maximum values of the absorption spectrum. As the curve descends (i.e., as the value of the vertical axis decreases), the slope of this tangent line repeatedly decreases and then increases. The tangent line drawn at the point where the slope value takes a minimum value on the longest wavelength side (except when the absorbance becomes 0.1 or less) is defined as the tangent line for the descent on the long-wavelength side of the absorption spectrum.
[1628] In addition, maximum points with an absorbance value of 0.2 or less are not included in the maximum values on the longest wavelength side.
[1629] In the organic EL device according to the present embodiment, it is preferable that the first light-emitting layer contains at least 0.5 mass% of the first light-emitting compound of the total mass of the first light-emitting layer.
[1630] The first light-emitting layer preferably contains the first light-emitting compound in an amount of 10 mass% or less of the total mass of the first light-emitting layer, more preferably contains 7 mass% or less of the total mass of the first light-emitting layer, and even more preferably contains 5 mass% or less of the total mass of the first light-emitting layer.
[1631] In an organic EL device according to the present embodiment, the first light-emitting layer preferably contains a first compound as a first host material in an amount of 60 mass% or more of the total mass of the first light-emitting layer, more preferably contains 70 mass% or more of the total mass of the first light-emitting layer, even more preferably contains 80 mass% or more of the total mass of the first light-emitting layer, even more preferably contains 90 mass% or more of the total mass of the first light-emitting layer, and even more preferably contains 95 mass% or more of the total mass of the first light-emitting layer.
[1632] It is preferable that the first light-emitting layer contains the first host material in an amount of 99.5 mass% or less of the total mass of the first light-emitting layer.
[1633] However, if the first light-emitting layer contains a first host material and a first light-emitting compound, the upper limit of the total content of the first host material and the first light-emitting compound is 100 mass%.
[1634] In the organic EL device according to the present embodiment, the film thickness of the first light-emitting layer is preferably 3 nm or more, and more preferably 5 nm or more. If the film thickness of the first light-emitting layer is 3 nm or more, it is a sufficient film thickness to cause recombination of holes and electrons in the first light-emitting layer.
[1635] In the organic EL device according to the present embodiment, the film thickness of the first light-emitting layer is preferably 15 nm or less, and more preferably 10 nm or less. If the film thickness of the first light-emitting layer is 15 nm or less, it is a sufficiently thin film thickness for triplet excitons to move to the second light-emitting layer.
[1636] In the organic EL device according to the present embodiment, it is more preferable that the film thickness of the first light-emitting layer is 3 nm or more and 15 nm or less.
[1637] (2nd light-emitting layer)
[1638] The second light-emitting layer includes a second host material. The second host material is a compound different from the first host material contained in the first light-emitting layer.
[1639] The second emitting layer preferably comprises a second emitting compound. The second emitting compound is not particularly limited. The second emitting compound is preferably a compound exhibiting luminescence with a maximum peak wavelength of 500 nm or less, more preferably a compound exhibiting luminescence with a maximum peak wavelength of 480 nm or less, and even more preferably a compound exhibiting luminescence with a maximum peak wavelength of 430 nm or more and 480 nm or less. The second emitting compound is preferably a fluorescent emitting compound exhibiting fluorescent luminescence with a maximum peak wavelength of 500 nm or less, more preferably a fluorescent emitting compound exhibiting fluorescent luminescence with a maximum peak wavelength of 480 nm or less, and even more preferably a fluorescent emitting compound exhibiting fluorescent luminescence with a maximum peak wavelength of 430 nm or more and 480 nm or less.
[1640] The method for measuring the maximum peak wavelength of a compound is as described above.
[1641] In the organic EL device according to the present embodiment, it is preferable that the second light-emitting layer emits light having a maximum peak wavelength of 500 nm or less when the device is driven.
[1642] In the organic EL device according to the present embodiment, it is preferable that the full width at half maximum of the second luminescent compound is 1 nm or more and 20 nm or less.
[1643] In the organic EL device according to the present embodiment, it is preferable that the Stokes shift of the second luminescent compound exceeds 7 nm.
[1644] If the Stokes shift of the second luminescent compound exceeds 7 nm, it becomes easier to prevent a decrease in luminescence efficiency due to self-absorption.
[1645] Self-absorption is a phenomenon in which an identical compound absorbs emitted light, causing a decrease in luminescence efficiency. Since self-absorption is significantly observed in compounds with a small Stokes shift (i.e., large overlap between the absorption and fluorescence spectra), it is desirable to use compounds with a large Stokes shift (small overlap between the absorption and fluorescence spectra) to suppress self-absorption. The Stokes shift can be measured by the method described below. The compound to be measured is 2.0 × 10⁻⁶ -5 A sample for measurement is prepared by dissolving the sample in toluene at a concentration of mol / L. The sample placed in a quartz cell is irradiated with continuous light in the ultraviolet-visible region at room temperature (300 K), and the absorption spectrum (vertical axis: absorbance, horizontal axis: wavelength) is measured. A spectrophotometer can be used for measuring the absorption spectrum; for example, the Hitachi High-Tech Sciences U-3900 / 3900H spectrophotometer can be used. In addition, the compound to be measured is 4.9 × 10⁻⁶ -6 A sample for measurement is prepared by dissolving it in toluene at a concentration of mol / L. Excitation light is irradiated onto the sample placed in a quartz cell at room temperature (300 K), and the fluorescence spectrum (vertical axis: fluorescence intensity, horizontal axis: wavelength) is measured. A spectrophotometer can be used for measuring the fluorescence spectrum. For example, the F-7000 spectrofluorescence spectrophotometer from Hitachi High-Tech Science can be used. From these absorption and fluorescence spectra, the difference between the wavelength of maximum absorption and the wavelength of maximum fluorescence is calculated to obtain the Stokes shift (SS). The unit of the Stokes shift (SS) is nm.
[1646] In the organic EL device according to the present 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 relationship of the following formula (Equation 30A).
[1647] T1(D2) > T1(H2) … (Equation 30A)
[1648] In the organic EL device according to the present embodiment, the second emitting compound and the second host material satisfy the relationship of the above formula (Equation 30A), so that when a triplet exciton generated in the first emitting layer moves to the second emitting layer, it transfers energy to the molecules of the second host material rather than to the second emitting compound having a higher triplet energy. Furthermore, the triplet exciton generated by the recombination of holes and electrons on the second host material does not move to the second emitting compound having a higher triplet energy. The triplet exciton generated by recombination on the molecules of the second emitting compound rapidly transfers energy to the molecules of the second host material.
[1649] Triplet excitons of the second host material do not move to the second luminescent compound, and triplet excitons efficiently collide with each other on the second host material due to the TTF phenomenon, thereby generating singlet excitons.
[1650] In the organic EL device according to the present embodiment, it is preferable that the singlet energy S1 (H2) of the second host material and the singlet energy S1 (D2) of the second luminescent compound satisfy the relationship of the following formula (Equation 4).
[1651] S1(H2) > S1(D2) … (Equation 4)
[1652] In the organic EL device according to the present embodiment, the second luminescent compound and the second host material satisfy the relationship of the above formula (Equation 4), so that the singlet energy of the second luminescent compound is smaller than the singlet energy of the second host material, and thus the singlet exciton generated by the TTF phenomenon transfers energy from the second host material to the second luminescent compound, contributing to the fluorescent emission of the second luminescent compound.
[1653] In the organic EL device according to the present embodiment, the second luminescent compound is preferably a compound that does not contain a zygos ring structure in its molecule.
[1654] In the organic EL device according to the present embodiment, it is preferable that the second luminescent compound is not a boron-containing complex, and it is more preferable that the second luminescent compound is not a complex.
[1655] As a blue fluorescently emitting compound that can be used in the second light-emitting layer, a compound selected from the group consisting of, for example, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, and triarylamine derivatives may be used.
[1656] In the organic EL device according to the present embodiment, it is preferable that the second light-emitting layer does not contain a metal complex. In addition, in the organic EL device according to the present embodiment, it is also preferable that the second light-emitting layer does not contain a boron-containing complex.
[1657] In the organic EL device according to the present embodiment, it is preferable that the second light-emitting layer does not include a phosphorescent light-emitting material (dopant material).
[1658] In addition, it is preferable that the second light-emitting layer does not include heavy metal complexes and phosphorescent rare earth metal complexes. Here, examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.
[1659] In the organic EL device according to the present embodiment, it is more preferable that the second light-emitting layer contains at least 0.5 mass% of the second light-emitting compound of the total mass of the second light-emitting layer.
[1660] The second light-emitting layer preferably contains the second light-emitting compound in an amount of 10 mass% or less of the total mass of the second light-emitting layer, more preferably contains 7 mass% or less of the total mass of the second light-emitting layer, and even more preferably contains 5 mass% or less of the total mass of the second light-emitting layer.
[1661] The second light-emitting layer preferably contains at least 60 mass% of the total mass of the second light-emitting layer, more preferably at least 70 mass% of the total mass of the second light-emitting layer, even more preferably at least 80 mass% of the total mass of the second light-emitting layer, even more preferably at least 90 mass% of the total mass of the second light-emitting layer, and even more preferably at least 95 mass% of the total mass of the second light-emitting layer.
[1662] It is preferable that the second light-emitting layer contains the second host material in an amount of 99.5 mass% or less of the total mass of the second light-emitting layer.
[1663] When the second emitting layer contains a second host material and a second emitting compound, the upper limit of the total content of the second host material and the second emitting compound is 100 mass%.
[1664] In the organic EL device according to the present embodiment, the film thickness of the second light-emitting layer is preferably 5 nm or more, more preferably 10 nm or more, and even more preferably 15 nm or more. If the film thickness of the second light-emitting layer is 5 nm or more, it is easy to suppress triplet excitons that have moved from the first light-emitting layer to the second light-emitting layer from returning to the first light-emitting layer. In addition, if the film thickness of the second light-emitting layer is 5 nm or more, triplet excitons can be sufficiently separated from the recombination portion in the first light-emitting layer.
[1665] In the organic EL device according to the present embodiment, the film thickness of the second light-emitting layer is preferably 20 nm or less. If the film thickness of the second light-emitting layer is 20 nm or less, the density of triplet excitons in the second light-emitting layer can be increased, making it easier for the TTF phenomenon to occur.
[1666] In the organic EL device according to the present embodiment, the film thickness of the second light-emitting layer is preferably 5 nm or more and 20 nm or less.
[1667] In the organic EL device according to the present embodiment, it is preferable that the triplet energy T1 (DX) of the first luminescent compound or the second luminescent compound, the triplet energy T1 (H1) of the first host material, and the triplet energy T1 (H2) of the second host material satisfy the relationship of the following formula (Equation 9), and it is more preferable that they satisfy the relationship of the following formula (Equation 10).
[1668] 2.7 eV > T1(DX) > T1(H1) > T1(H2) … (Equation 9)
[1669] 2.6 eV > T1(DX) > T1(H1) > T1(H2) … (Equation 10)
[1670] The triplet energy T1 (D1) of the first luminescent compound preferably satisfies the relationship of the following formula (Equation 9A), and more preferably satisfies the relationship of the following formula (Equation 10A).
[1671] 2.7 eV > T1(D1) > T1(H1) > T1(H2) … (Equation 9A)
[1672] 2.6 eV > T1(D1) > T1(H1) > T1(H2) … (Equation 10A)
[1673] The triplet energy T1 (D2) of the second luminescent compound preferably satisfies the relationship of the following formula (Equation 9B), and more preferably satisfies the relationship of the following formula (Equation 10B).
[1674] 2.7 eV > T1(D2) > T1(H1) > T1(H2) … (Equation 9B)
[1675] 2.6 eV > T1(D2) > T1(H1) > T1(H2) … (Equation 10B)
[1676] In the organic EL device according to the present embodiment, it is preferable that the triplet energy T1 (DX) of the first luminescent compound or the second luminescent compound and the triplet energy T1 (H1) of the first host material satisfy the relationship of the following formula (Equation 11).
[1677] 0 eV < T1(DX) - T1(H1) < 0.6 eV … (Equation 11)
[1678] It is desirable that the triplet energy T1 (D1) of the first luminescent compound satisfies the relationship of the following formula (Equation 11A).
[1679] 0 eV < T1(D1) - T1(H1) < 0.6 eV … (Equation 11A)
[1680] It is desirable that the triplet energy T1 (D2) of the second luminescent compound satisfies the relationship of the following formula (Equation 11B).
[1681] 0 eV < T1(D2) - T1(H2) < 0.8 eV … (Equation 11B)
[1682] In the organic EL device according to the present embodiment, it is preferable that the triplet energy T1 (H1) of the first host material satisfies the relationship of the following formula (Equation 12).
[1683] T1(H1) > 2.0 eV … (Equation 12)
[1684] In the organic EL device according to the present embodiment, it is preferable that the triplet energy T1 (H1) of the first host material satisfies the relationship of the following formula (Equation 12A) and also satisfies the relationship of the following formula (Equation 12B).
[1685] T1(H1) > 2.10 eV … (Equation 12A)
[1686] T1(H1) > 2.15 eV … (Equation 12B)
[1687] In the organic EL device according to the present embodiment, the triplet energy T1 (H1) of the first host material satisfies the relationship of the above formula (Equation 12A) or the above formula (Equation 12B), thereby making it easier for triplet excitons generated in the first light-emitting layer to move to the second light-emitting layer, and also making it easier to suppress reverse movement from the second light-emitting layer to the first light-emitting layer. As a result, singlet excitons are efficiently generated in the second light-emitting layer, and the light-emitting efficiency is improved.
[1688] In the organic EL device according to the present embodiment, it is preferable that the triplet energy T1 (H1) of the first host material satisfies the relationship of the following formula (Equation 12C), and it is also preferable that it satisfies the relationship of the following formula (Equation 12D).
[1689] 2.08 eV > T1(H1) > 1.87 eV … (Equation 12C)
[1690] 2.05 eV > T1(H1) > 1.90 eV … (Equation 12D)
[1691] In the organic EL device according to the present embodiment, the triplet energy T1 (H1) of the first host material satisfies the relationship of the above formula (Equation 12C) or the above formula (Equation 12D), thereby reducing the energy of the triplet exciton generated in the first light-emitting layer, and thus, a long lifespan of the blue organic EL device of the organic EL device can be expected.
[1692] In the organic EL device according to the present embodiment, it is preferable that the triplet energy T1 (D1) of the first luminescent compound satisfies the relationship of the following formula (Equation 14A) and also satisfies the relationship of the following formula (Equation 14B).
[1693] 2.60 eV > T1(D1) … (Equation 14A)
[1694] 2.50 eV > T1(D1) … (Equation 14B)
[1695] By the first light-emitting layer containing a first light-emitting compound that satisfies the relationship of the above formula (Equation 14A) or (Equation 14B), the blue organic EL element of the organic EL element has a long lifespan.
[1696] In the organic EL device according to the present embodiment, it is preferable that the triplet energy T1 (D2) of the second luminescent compound satisfies the relationship of the following formula (Equation 14C), and it is also preferable that it satisfies the relationship of the following formula (Equation 14D).
[1697] 2.60 eV > T1(D2) … (Equation 14C)
[1698] 2.50 eV > T1(D2) … (Equation 14D)
[1699] By the second light-emitting layer containing a compound that satisfies the relationship of the above formula (Formula 14C) or (Formula 14D), the blue organic EL element of the organic EL element has a long lifespan.
[1700] In the organic EL device according to the present embodiment, it is preferable that the triplet energy T1 (H2) of the second host material satisfies the relationship of the following formula (Equation 13).
[1701] T1(H2) ≥ 1.9 eV … (Equation 13)
[1702] In the organic EL device according to the present embodiment, when the stacking order of the first light-emitting layer and the second light-emitting layer is the order of the first light-emitting layer and the second light-emitting layer from the anode side, it is also desirable that the electron mobility μe (H1) of the first host material and the electron mobility μe (H2) of the second host material satisfy the relationship of the following formula (Equation 30).
[1703] μe(H2) > μe(H1) … (Equation 30)
[1704] By satisfying the relationship of the above formula (Equation 30) between the first host material and the second host material, the recombination ability of holes and electrons in the first light-emitting layer is improved.
[1705] In the organic EL device according to the present embodiment, when the stacking order of the first light-emitting layer and the second light-emitting layer is the order of the first light-emitting layer and the second light-emitting layer from the anode side, it is also desirable that the hole mobility μh (H1) of the first host material and the hole mobility μh (H2) of the second host material satisfy the relationship of the following formula (Equation 31).
[1706] μh(H1) > μh(H2) … (Equation 31)
[1707] In the organic EL device according to the present embodiment, when the stacking order of the first light-emitting layer and the second light-emitting layer is the order of the first light-emitting layer and the second light-emitting layer from the anode side, it is also desirable that the hole mobility μh (H1) of the first host material, the electron mobility μe (H1) of the first host material, the hole mobility μh (H2) of the second host material, and the electron mobility μe (H2) of the second host material satisfy the relationship of the following formula (Equation 32).
[1708] (μe(H2) / μh(H2)) > (μe(H1) / μh(H1)) … (Equation 32)
[1709] (First host material and second host material)
[1710] In the organic EL device according to the present embodiment, the first host material and the second host material are preferably compounds selected from the group consisting of, for example, a first compound represented by the following general formula (1), a first compound represented by the following general formula (1X), general formula (12X), general formula (13X), general formula (14X), general formula (15X), or general formula (16X), and a second compound represented by the following general formula (2). Additionally, the first compound may be used as the first host material and the second host material, and in this case, the compound represented by the following general formula (1) or the following general formula (1X), general formula (12X), general formula (13X), general formula (14X), general formula (15X), or general formula (16X) used as the second host material may be conveniently referred to as the second compound.
[1711] ·1st compound
[1712] In the organic EL device according to the present embodiment, the first compound is a compound represented by, for example, the following general formula (1), general formula (1X), general formula (12X), general formula (13X), general formula (14X), general formula (15X) or general formula (16X).
[1713] · Compound represented by general formula (1)
[1714] In the organic EL device according to the present embodiment, it is preferable that the first compound is a compound represented by the following general formula (1). The first compound represented by the following general formula (1) has at least one group represented by the following general formula (11).
[1715] [Chemical Formula 233]
[1716]
[1717] In the above general formula (1),
[1718] R 101 ~R 110 each independently
[1719] hydrogen atom,
[1720] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1721] Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
[1722] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[1723] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[1724] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1725] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[1726] -O-(R 904 The one indicated by ),
[1727] -S-(R 905 The one indicated by ),
[1728] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,
[1729] -C(=O)R 801 The one indicated by,
[1730] -COOR 802 The one indicated by,
[1731] Halogen atoms,
[1732] Cyanogi,
[1733] Nitro,
[1734] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
[1735] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, or
[1736] The above general formula (11) is a device represented by the above general formula,
[1737] However, R 101 ~R 110 At least one of them is a device represented by the above general formula (11), and
[1738] In the case where there are multiple devices represented by the above general formula (11), the multiple devices represented by the above general formula (11) are identical or different from each other,
[1739] L 101 silver,
[1740] single bond,
[1741] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[1742] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[1743] Ar 101 silver,
[1744] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1745] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[1746] mx is 0, 1, 2, 3, 4, or 5, and
[1747] L 101 If there are 2 or more of these, 2 or more L 101 They are identical or different from each other,
[1748] Ar 101 If 2 or more exist, 2 or more Ar 101 They are identical or different from each other,
[1749] In the above general formula (11), * indicates the bonding position with the pyrene ring in the above general formula (1).
[1750] Among the first compounds represented by the above general formula (1), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are, each independently
[1751] hydrogen atom,
[1752] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1753] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1754] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1755] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[1756] R 901 If this plural exists, the plural R 901 They are identical or different from each other,
[1757] R 902 If there are multiple instances of R 902 are identical or different from each other,
[1758] R 903 If this plural exists, the plural R 903 They are identical or different from each other,
[1759] R 904 If there are multiple instances of R 904 are identical or different from each other,
[1760] R 905 If there are multiple instances of R 905 are identical or different from each other,
[1761] R 906 If this plural exists, the plural R 906 They are identical or different from each other,
[1762] R 907 If this plural exists, the plural R 907 They are identical or different from each other,
[1763] R 801 If this plural exists, the plural R 801 They are identical or different from each other,
[1764] R 802 If there are multiple instances of R 802 They are identical or different from each other.
[1765] In one embodiment, Ar 101 It is preferable that the silver be a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.
[1766] In one embodiment, Ar 101 It is preferable that the group be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted phenanthyl group, or a substituted or unsubstituted fluorenyl group.
[1767] In one embodiment, the first compound is preferably represented by the following general formula (101).
[1768] [Chemical Formula 234]
[1769]
[1770] (In the above general formula (101),
[1771] R 101 ~R 120 each independently
[1772] hydrogen atom,
[1773] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1774] Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
[1775] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[1776] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[1777] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1778] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[1779] -O-(R 904 The one indicated by ),
[1780] -S-(R 905 The one indicated by ),
[1781] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,
[1782] -C(=O)R 801 The one indicated by,
[1783] -COOR 802 The one indicated by,
[1784] Halogen atoms,
[1785] Cyanogi,
[1786] Nitro,
[1787] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1788] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[1789] However, R 101 ~R 110 One of them is L 101 Indicates the binding position with, and R 111 ~R 120 One of them is L 101 Indicates the binding position with,
[1790] L 101 silver,
[1791] single bond,
[1792] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[1793] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[1794] mx is 0, 1, 2, 3, 4, or 5, and
[1795] L 101 If there are 2 or more of these, 2 or more L 101 They are identical or different from each other.
[1796] In one embodiment, L 101 It is preferable that the ring-forming arylene group has 6 to 50 carbon atoms and is a single bond, or a substituted or unsubstituted ring.
[1797] In one embodiment, R 101 ~R 110 It is preferable that at least two of them are represented by the above general formula (11).
[1798] In one embodiment, R 101 ~R 110 At least two of them are represented by the above general formula (11), and also Ar 101 It is preferable that the silver be a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.
[1799] In one embodiment, Ar 101 is not a substituted or unsubstituted pyrenyl group, and L 101 R is not a substituted or unsubstituted pyrenyllene group and is not a group represented by the above general formula (11). 101 ~R 110 It is preferable that the substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms is not a substituted or unsubstituted pyrenyl group.
[1800] In one embodiment, R that is not a group represented by the general formula (11) 101 ~R 110 It is preferable that each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
[1801] In one embodiment, R that is not a group represented by the general formula (11) 101 ~R 110It is preferable that each be independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms.
[1802] In one embodiment, R that is not a group represented by the general formula (11) 101 ~R 110 It is preferable that it be a hydrogen atom.
[1803] · Compounds represented by the general formula (1X)
[1804] In the organic EL device according to the present embodiment, it is also preferable that the first compound is a compound represented by the following general formula (1X).
[1805] [Chemical Formula 235]
[1806]
[1807] (In the above general formula (1X),
[1808] R 101 ~R 112 are, each independently
[1809] hydrogen atom,
[1810] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1811] Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
[1812] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[1813] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[1814] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1815] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[1816] -O-(R 904 The one indicated by ),
[1817] -S-(R905 The one indicated by ),
[1818] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,
[1819] -C(=O)R 801 The one indicated by,
[1820] -COOR 802 The one indicated by,
[1821] Halogen atoms,
[1822] Cyanogi,
[1823] Nitro,
[1824] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
[1825] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, or
[1826] The above general formula (11X) is a device represented by the above general formula, and
[1827] However, R 101 ~R 112 At least one of them is a device represented by the above general formula (11X), and
[1828] If there are multiple devices represented by the above general formula (11X), the multiple devices represented by the above general formula (11X) may be identical or different from each other,
[1829] L 101 silver,
[1830] single bond,
[1831] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[1832] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[1833] Ar 101 silver,
[1834] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1835] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[1836] mx is 1, 2, 3, 4, or 5, and
[1837] L 101 If there are 2 or more of these, 2 or more L 101 They are identical or different from each other,
[1838] Ar 101 If 2 or more exist, 2 or more Ar 101 They are identical or different from each other,
[1839] In the above general formula (11X), * indicates the bonding position with the benz[a]anthracene ring in the above general formula (1X).
[1840] In the organic EL device according to the present embodiment, the device represented by the general formula (11X) is preferably the device represented by the following general formula (111X).
[1841] [Chemical Formula 236]
[1842]
[1843] (In the above general formula (111X),
[1844] X1 is CR 143 R 144 , oxygen atom, sulfur atom, or NR 145 And,
[1845] L 111 and L 112 are, each independently
[1846] single bond,
[1847] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[1848] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[1849] ma is 1, 2, 3, or 4, and
[1850] mb is 1, 2, 3, or 4, and
[1851] ma + mb is 2, 3, or 4, and
[1852] Ar 101 is Ar in the above general formula (11X). 101 It has the same meaning as,
[1853] R 141 , R 142 , R 143 , R 144 and R 145 are, each independently
[1854] hydrogen atom,
[1855] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1856] Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
[1857] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[1858] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[1859] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1860] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[1861] -O-(R 904 The one indicated by ),
[1862] -S-(R 905 The one indicated by ),
[1863] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,
[1864] -C(=O)R 801 The one indicated by,
[1865] -COOR 802 The one indicated by,
[1866] Halogen atoms,
[1867] Cyanogi,
[1868] Nitro,
[1869] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1870] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[1871] mc is 3, and
[1872] 3 Rs 141 They are identical or different from each other,
[1873] md is 3, and
[1874] 3 Rs 142 are identical or different from each other.
[1875] In the group represented by the above general formula (111X), among the positions of carbon atoms *1 to *8 in the ring structure represented by the following general formula (111aX), L at any one of *1 to *4 111 This combines, and R at the remaining 3 positions among *1~*4 141 This combines, and L at any one of *5~*8 112 combines, and R at the remaining 3 positions among *5~*8 142 combines.
[1876] [Chemical Formula 237]
[1877]
[1878] For example, in the apparatus represented by the above general formula (111X), L 111 This bonds to the position of the carbon atom at *2 in the ring structure represented by the above general formula (111aX), and L 112 When bonding to the position of the carbon atom of *7 in the ring structure represented by the above general formula (111aX), the group represented by the above general formula (111X) is represented by the following general formula (111bX).
[1879] [Chemical Formula 238]
[1880]
[1881] (In the above general formula (111bX),
[1882] X1, L 111 , L 112 , ma, mb, Ar 101 , R 141 , R 142 , R 143 , R 144 and R 145 X1 and L in the above general formula (111X) are each independently 111 , L 112 , ma, mb, Ar 101 , R 141 , R 142 , R 143 , R 144 and R 145 It has the same meaning as,
[1883] Multiple R 141 They are identical or different from each other,
[1884] Multiple R 142 are identical or different from each other.
[1885] In the organic EL device according to the present embodiment, it is preferable that the group represented by the general formula (111X) is the group represented by the general formula (111bX).
[1886] In the compound represented by the above general formula (1X), it is preferable that ma is 1 or 2 and mb is 1 or 2.
[1887] In the compound represented by the above general formula (1X), it is preferable that ma is 1 and mb is 1.
[1888] In the compound represented by the above chemical formula (1X), Ar 101 It is preferable that the silver be a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.
[1889] In the compound represented by the above general formula (1X), Ar 101It is preferable that the silver be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted benz[a]anthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted fluorenyl group.
[1890] The compound represented by the above general formula (1X) is also preferably represented by the following general formula (101X).
[1891] [Chemical Formula 239]
[1892]
[1893] (In the above general formula (101X),
[1894] R 111 and R 112 One of them is L 101 Indicates the binding position with, and R 133 and R 134 One of them is L 101 Indicates the binding position with,
[1895] R 101 ~R 110 , R 121 ~R 130 , L 101 R, not the binding site with 111 or R 112 , and L 101 R, not the binding site with 133 or R 134 are, each independently
[1896] hydrogen atom,
[1897] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1898] Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
[1899] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[1900] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[1901] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1902] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[1903] -O-(R 904 The one indicated by ),
[1904] -S-(R 905 The one indicated by ),
[1905] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,
[1906] -C(=O)R 801 The one indicated by,
[1907] -COOR 802 The one indicated by,
[1908] Halogen atoms,
[1909] Cyanogi,
[1910] Nitro,
[1911] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1912] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[1913] L 101 silver,
[1914] single bond,
[1915] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[1916] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[1917] mx is 1, 2, 3, 4, or 5, and
[1918] L 101 If there are 2 or more of these, 2 or more L 101 They are identical or different from each other.
[1919] In the compound represented by the above chemical formula (1X), L 101 It is preferable that the ring-forming arylene group has 6 to 50 carbon atoms and is a single bond, or a substituted or unsubstituted ring.
[1920] The compound represented by the above general formula (1X) is also preferably represented by the following general formula (102X).
[1921] [Chemical Formula 240]
[1922]
[1923] (In the above general formula (102X),
[1924] R 111 and R 112 One of them is L 111 Indicates the binding position with, and R 133 and R 134 One of them is L 112 Indicates the bonding position with,
[1925] R 101 ~R 110 , R 121 ~R 130 , L 111 R, not the binding site with 111 or R 112 and L 112 R, not the bonding position with 133 or R 134 are, each independently
[1926] hydrogen atom,
[1927] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1928] Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
[1929] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[1930] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[1931] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1932] -Si(R901 )(R 902 )(R 903 The one indicated by ),
[1933] -O-(R 904 The one indicated by ),
[1934] -S-(R 905 The one indicated by ),
[1935] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,
[1936] -C(=O)R 801 The one indicated by,
[1937] -COOR 802 The one indicated by,
[1938] Halogen atoms,
[1939] Cyanogi,
[1940] Nitro,
[1941] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1942] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[1943] X1 is CR 143 R 144 , oxygen atom, sulfur atom, or NR 145 is,
[1944] L 111 and L 112 are, each independently
[1945] single bond,
[1946] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[1947] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[1948] ma is 1, 2, 3, or 4, and
[1949] mb is 1, 2, 3, or 4, and
[1950] ma+mb is 2, 3, 4, or 5, and
[1951] R 141 , R 142 , R 143 , R 144 and R 145 are, each independently
[1952] hydrogen atom,
[1953] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1954] Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
[1955] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[1956] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[1957] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1958] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[1959] -O-(R 904 The one indicated by ),
[1960] -S-(R 905 The one indicated by ),
[1961] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,
[1962] -C(=O)R 801 The one indicated by,
[1963] -COOR 802 The one indicated by,
[1964] Halogen atoms,
[1965] Cyanogi,
[1966] Nitro,
[1967] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1968] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[1969] mc is 3, and
[1970] 3 Rs 141 They are identical or different from each other,
[1971] md is 3, and
[1972] 3 Rs 142 are identical or different from each other.
[1973] In the compound represented by the above general formula (1X), it is preferable that ma in the above general formula (102X) is 1 or 2 and mb is 1 or 2.
[1974] In the compound represented by the above general formula (1X), it is preferable that ma in the above general formula (102X) is 1 and mb is 1.
[1975] In the compound represented by the above general formula (1X), it is also preferable that the group represented by the above general formula (11X) is the group represented by the following general formula (11AX) or the group represented by the following general formula (11BX).
[1976] [Chemical Formula 241]
[1977]
[1978] (In the above general formula (11AX) and the above general formula (11BX),
[1979] R 121 ~R 131 each independently
[1980] hydrogen atom,
[1981] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1982] Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
[1983] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[1984] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[1985] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1986] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[1987] -O-(R 904 The one indicated by ),
[1988] -S-(R 905 The one indicated by ),
[1989] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,
[1990] -C(=O)R 801 The one indicated by,
[1991] -COOR 802 The one indicated by,
[1992] Halogen atoms,
[1993] Cyanogi,
[1994] Nitro,
[1995] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1996] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[1997] If there are multiple devices represented by the above general formula (11AX), the multiple devices represented by the above general formula (11AX) are identical or different from each other, and
[1998] If there are multiple devices represented by the above general formula (11BX), the multiple devices represented by the above general formula (11BX) are identical or different from each other,
[1999] L 131 and L 132 are, each independently
[2000] single bond,
[2001] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[2002] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[2003] In the above general formulas (11AX) and (11BX), * represents the bonding position with the benz[a]anthracene ring in the above general formula (1X), respectively.
[2004] The compound represented by the above general formula (1X) is also preferably represented by the following general formula (103X).
[2005] [Chemical Formula 242]
[2006]
[2007] (In the above general formula (103X),
[2008] R 101 ~R 110 and R 112 are R in the above general formula (1X), respectively. 101 ~R 110 and R 112 It has the same meaning as,
[2009] R 121 ~R 131 , L 131 and L 132 are R in the above general formula (11BX), respectively. 121 ~R 131 , L 131 and L 132 It has the same meaning as.)
[2010] In the compound represented by the above chemical formula (1X), L 131 It is also preferable that the silver be a substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms.
[2011] In the compound represented by the above chemical formula (1X), L 132 It is also preferable that it be a substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms.
[2012] In the compound represented by the above general formula (1X), R 101 ~R 112It is also desirable that at least two of them are represented by the above general formula (11X).
[2013] In the compound represented by the chemical formula (1X), R 101 ~R 112 At least two of them are groups represented by the chemical formula (11X), and Ar in the chemical formula (11X) 101 It is preferable that the silver be a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.
[2014] In the compound represented by the above general formula (1X), Ar 101 is not a substituted or unsubstituted benz[a]anthryl group, and L 101 R is not a substituted or unsubstituted benz[a]anthrylene group, and is not a group represented by the general formula (11X) above. 101 ~R 110 It is also preferable that the substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms is not a substituted or unsubstituted benz[a]anthryl group.
[2015] In the compound represented by the above general formula (1X), R, which is not a group represented by the above general formula (11X). 101 ~R 112 It is preferable that each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
[2016] In the compound represented by the above chemical formula (1X), R, which is not a group represented by the above chemical formula (11X). 101 ~R 112 It is preferable that the atom be a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms.
[2017] In the compound represented by the above general formula (1X), R, which is not a group represented by the above general formula (11X). 101 ~R 112 It is preferable that it be a hydrogen atom.
[2018] · Compounds represented by the general formula (12X)
[2019] In the organic EL device according to the present embodiment, it is also preferable that the first compound is a compound represented by the following general formula (12X).
[2020] [Chemical Formula 243]
[2021]
[2022] (In the above general formula (12X),
[2023] R 1201 ~R 1210 One or more of the groups consisting of two or more adjacent groups,
[2024] They combine with each other to form a substituted or unsubstituted single ring, or
[2025] They combine with each other to form substituted or non-substituted condensation rings,
[2026] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 1201 ~R 1210 each independently
[2027] hydrogen atom,
[2028] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2029] Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
[2030] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2031] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2032] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2033] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[2034] -O-(R 904 The one indicated by ),
[2035] -S-(R 905 The one indicated by ),
[2036] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,
[2037] -C(=O)R 801 The one indicated by,
[2038] -COOR 802 The one indicated by,
[2039] Halogen atoms,
[2040] Cyanogi,
[2041] Nitro,
[2042] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
[2043] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, or
[2044] The above general formula (121) is a device represented by the above general formula,
[2045] However, the corresponding substituent in the case where the above-mentioned substituted or unsubstituted single ring has a substituent, the corresponding substituent in the case where the above-mentioned substituted or unsubstituted condensed ring has a substituent, and R 1201 ~R 1210 At least one of them is a device represented by the above general formula (121), and
[2046] If there are multiple devices represented by the above general formula (121), the multiple devices represented by the above general formula (121) may be identical or different from each other,
[2047] L 1201 silver,
[2048] single bond,
[2049] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[2050] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[2051] Ar 1201 silver,
[2052] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2053] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[2054] mx2 is 0, 1, 2, 3, 4, or 5, and
[2055] L 1201 If there are 2 or more of these, 2 or more L 1201 They are identical or different from each other,
[2056] Ar 1201 If 2 or more exist, 2 or more Ar 1201 They are identical or different from each other,
[2057] In the above general formula (121), * indicates the position of connection with the ring represented by the above general formula (12X).
[2058] In the above general formula (12X), R 1201 ~R 1210 A mole consisting of 2 adjacent ones, R 1201 and R 1202 of, R 1202 and R 1203 of, R 1203 and R 1204 of, R 1204 and R 1205 of, R 1205 and R 1206 of, R 1207 and R 1208 of, R 1208 and R 1209 of, and R 1209 and R 1210 It is the group of.
[2059] · Compounds represented by the general formula (13X)
[2060] In the organic EL device according to the present embodiment, it is also preferable that the first compound is a compound represented by the following general formula (13X).
[2061] [Chemical Formula 244]
[2062]
[2063] (In the above general formula (13X),
[2064] R 1301 ~R 1310 each independently
[2065] hydrogen atom,
[2066] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2067] Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
[2068] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2069] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2070] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2071] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[2072] -O-(R 904 The one indicated by ),
[2073] -S-(R 905 The one indicated by ),
[2074] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,
[2075] -C(=O)R 801 The device indicated as,
[2076] -COOR 802 The one indicated by,
[2077] Halogen atoms,
[2078] Cyanogi,
[2079] Nitro,
[2080] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
[2081] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, or
[2082] The above general formula (131) is a device represented by the above general formula,
[2083] However, R 1301 ~R 1310 At least one of them is a device represented by the above general formula (131), and
[2084] If there are multiple devices represented by the above general formula (131), the multiple devices represented by the above general formula (131) may be identical or different from each other,
[2085] L 1301 silver,
[2086] single bond,
[2087] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[2088] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[2089] Ar 1301 silver,
[2090] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2091] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[2092] mx3 is 0, 1, 2, 3, 4, or 5, and
[2093] L 1301 If there are 2 or more of these, 2 or more L 1301 They are identical or different from each other,
[2094] Ar 1301 If 2 or more exist, 2 or more Ar 1301They are identical or different from each other,
[2095] In the above general formula (131), * indicates the bonding position with the fluoranthene ring in the above general formula (13X).
[2096] In the organic EL device according to the present embodiment, R, which is not a group represented by the general formula (131), 1301 ~R 1310 Among them, groups consisting of two or more adjacent elements do not combine with each other. In the above general formula (13X), a group consisting of two adjacent elements is R 1301 and R 1302 of, R 1302 and R 1303 of, R 1303 and R 1304 of, R 1304 and R 1305 of, R 1305 and R 1306 of, R 1307 and R 1308 of, R 1308 and R 1309 of, and R 1309 and R 1310 It is the group of.
[2097] · Compounds represented by the general formula (14X)
[2098] In the organic EL device according to the present embodiment, it is also preferable that the first compound is a compound represented by the following general formula (14X).
[2099] [Chemical Formula 245]
[2100]
[2101] (In the above general formula (14X),
[2102] R 1401 ~R 1410 each independently
[2103] hydrogen atom,
[2104] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2105] Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
[2106] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2107] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2108] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2109] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[2110] -O-(R 904 The one indicated by ),
[2111] -S-(R 905 The one indicated by ),
[2112] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,
[2113] -C(=O)R 801 The one indicated by,
[2114] -COOR 802 The one indicated by,
[2115] Halogen atoms,
[2116] Cyanogi,
[2117] Nitro,
[2118] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
[2119] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, or
[2120] The above general formula (141) is a device represented by the above general formula,
[2121] However, R 1401 ~R 1410 At least one of them is a device represented by the above general formula (141), and
[2122] If there are multiple devices represented by the above general formula (141), the multiple devices represented by the above general formula (141) may be identical or different from each other,
[2123] L 1401 silver,
[2124] single bond,
[2125] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[2126] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[2127] Ar 1401 silver,
[2128] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2129] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[2130] mx4 is 0, 1, 2, 3, 4, or 5, and
[2131] L 1401 If there are 2 or more of these, 2 or more L 1401 They are identical or different from each other,
[2132] Ar 1401 If 2 or more exist, 2 or more Ar 1401 They are identical or different from each other,
[2133] In the above general formula (141), * indicates the position of connection with the ring represented by the above general formula (14X).
[2134] · Compounds represented by the general formula (15X)
[2135] In the organic EL device according to the present embodiment, it is also preferable that the first compound is a compound represented by the following general formula (15X).
[2136] [Chemical Formula 246]
[2137]
[2138] (In the above general formula (15X),
[2139] R 1501 ~R 1514 are, each independently
[2140] hydrogen atom,
[2141] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2142] Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
[2143] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2144] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2145] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2146] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[2147] -O-(R 904 The one indicated by ),
[2148] -S-(R 905 The one indicated by ),
[2149] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,
[2150] -C(=O)R 801 The one indicated by,
[2151] -COOR 802 The one indicated by,
[2152] Halogen atoms,
[2153] Cyanogi,
[2154] Nitro,
[2155] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
[2156] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, or
[2157] The above general formula (151) is a device represented by the above general formula,
[2158] However, R 1501 ~R 1514 At least one of them is a device represented by the above general formula (151), and
[2159] If there are multiple devices represented by the above general formula (151), the multiple devices represented by the above general formula (151) may be identical or different from each other,
[2160] L 1501 silver,
[2161] single bond,
[2162] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[2163] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[2164] Ar 1501 silver,
[2165] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2166] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[2167] mx5 is 0, 1, 2, 3, 4, or 5, and
[2168] L 1501 If there are 2 or more of these, 2 or more L 1501 They are identical or different from each other,
[2169] Ar 1501 If 2 or more exist, 2 or more Ar 1501 They are identical or different from each other,
[2170] In the above general formula (151), * indicates the position of connection with the ring represented by the above general formula (15X).
[2171] · Compounds represented by the general formula (16X)
[2172] In the organic EL device according to the present embodiment, it is also preferable that the first compound is a compound represented by the following general formula (16X).
[2173] [Chemical Formula 247]
[2174]
[2175] (In the above general formula (16X),
[2176] R 1601 ~R 1614 are, each independently
[2177] hydrogen atom,
[2178] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2179] Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
[2180] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2181] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2182] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2183] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[2184] -O-(R 904 The one indicated by ),
[2185] -S-(R 905 The one indicated by ),
[2186] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,
[2187] -C(=O)R 801 The one indicated by,
[2188] -COOR 802 The one indicated by,
[2189] Halogen atoms,
[2190] Cyanogi,
[2191] Nitro,
[2192] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
[2193] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, or
[2194] The above general formula (161) is a device represented by the above general formula,
[2195] However, R 1601 ~R 1614 At least one of them is a device represented by the above general formula (161), and
[2196] If there are multiple devices represented by the above general formula (161), the multiple devices represented by the above general formula (161) may be identical or different from each other,
[2197] L 1601 silver,
[2198] single bond,
[2199] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[2200] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[2201] Ar 1601 silver,
[2202] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2203] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[2204] mx6 is 0, 1, 2, 3, 4, or 5, and
[2205] L 1601 If there are 2 or more of these, 2 or more L 1601 They are identical or different from each other,
[2206] Ar 1601 If 2 or more exist, 2 or more Ar 1601 They are identical or different from each other,
[2207] In the above general formula (161), * indicates the position of connection with the ring represented by the above general formula (16X).
[2208] In the organic EL device according to the present embodiment, the first host material has a linkage structure including a benzene ring and a naphthalene ring connected by a single bond in the molecule, and in the benzene ring and the naphthalene ring in the linkage structure, a single ring or a condensed ring is independently further condensed or not condensed, and in the case of the benzene ring and the naphthalene ring in the linkage structure, it is also preferable that the benzene ring and the naphthalene ring in the linkage structure are further connected by a crosslink in at least one part other than the single bond.
[2209] Since the first host material has a connection structure including such crosslinking, it is possible to expect suppression of color degradation of the organic EL device.
[2210] In this case, the first host material may have, as a minimum unit, a linkage structure (sometimes referred to as a benzene-naphthalene linkage structure) comprising a benzene ring and a naphthalene ring connected by a single bond, as indicated by the following formula (X1) or formula (X2), and may further have a single ring or a condensed ring condensed to the benzene ring, or may further have a single ring or a condensed ring condensed to the naphthalene ring. For example, even in the first host material, in the linkage structure (sometimes referred to as a naphthalene-naphthalene linkage structure) comprising a naphthalene ring and a naphthalene ring connected by a single bond, as indicated by the following formulas (X3), (X4), or (X5), one naphthalene ring contains a benzene ring, so it contains a benzene-naphthalene linkage structure.
[2211] [Chemical Formula 248]
[2212]
[2213] In the organic EL device according to the present embodiment, it is also preferable that the crosslinking includes a double bond. That is, it is also preferable that the benzene ring and the naphthalene ring have a structure in which they are further connected by a crosslinking structure that includes a double bond in a portion other than a single bond.
[2214] If the benzene ring and the naphthalene ring in the benzene-naphthalene linkage structure are further connected by a crosslink in at least one portion other than a single bond, for example, in the case of the above formula (X1), a linkage structure (condensed ring) represented by the following formula (X11) is formed, and in the case of the above formula (X3), a linkage structure (condensed ring) represented by the following formula (X31) is formed.
[2215] If the benzene ring and the naphthalene ring in the benzene-naphthalene linkage structure are further connected by a crosslinking that includes a double bond in a portion other than a single bond, for example, in the case of the above formula (X1), the linkage structure (condensed ring) represented by the following formula (X12); in the case of the above formula (X2), the linkage structure (condensed ring) represented by the following formula (X21) or formula (X22); in the case of the above formula (X4), the linkage structure (condensed ring) represented by the following formula (X41); and in the case of the above formula (X5), the linkage structure (condensed ring) represented by the following formula (X51).
[2216] If the benzene ring and the naphthalene ring in the benzene-naphthalene linkage structure are further connected by a crosslink comprising a heteroatom (e.g., an oxygen atom) in at least one portion other than the single bond, for example in the case of the above formula (X1), a linkage structure (condensation ring) is formed as represented by the following formula (X13).
[2217] [Chemical Formula 249]
[2218]
[2219] In the organic EL device according to the present embodiment, the first host material has a biphenyl structure in which a first benzene ring and a second benzene ring are connected by a single bond in the molecule, and it is also preferable that the first benzene ring and the second benzene ring in the biphenyl structure are further connected by crosslinking in at least one part other than the single bond.
[2220] In the organic EL device according to the present embodiment, it is also preferable that the first benzene ring and the second benzene ring in the biphenyl structure are further connected by the crosslinking in one portion other than the single bond. By having the first host material have a biphenyl structure including such crosslinking, it is possible to expect suppression of color deterioration of the organic EL device.
[2221] In the organic EL device according to the present embodiment, it is also preferable that the crosslinking includes a double bond.
[2222] In the organic EL device according to the present embodiment, it is also preferable that the crosslinking does not include a double bond.
[2223] It is also preferable that the first benzene ring and the second benzene ring in the above biphenyl structure are further connected by the crosslinking in two parts other than the single bond.
[2224] In the organic EL device according to the present embodiment, it is also preferable that the first benzene ring and the second benzene ring in the biphenyl structure are further connected by the crosslinking in two parts other than the single bond, and that the crosslinking does not include a double bond. By having the first host material have a biphenyl structure including such crosslinking, it is possible to expect suppression of color deterioration of the organic EL device.
[2225] For example, if the first benzene ring and the second benzene ring of the biphenyl structure represented by the following formula (BP1) are further connected by a crosslink in at least one portion other than a single bond, the biphenyl structure becomes a connected structure (condensed ring) such as the following formulas (BP11) to (BP15).
[2226] [Chemical Formula 250]
[2227]
[2228] The above formula (BP11) is a structure connected by a crosslink that does not include a double bond in one part other than the single bond.
[2229] The above formula (BP12) is a structure connected by a crosslink including a double bond in one part other than the single bond.
[2230] The above formula (BP13) is a structure connected by a crosslink that does not include double bonds in two parts other than the single bond.
[2231] The above formula (BP14) is a structure in which one of the two parts other than the single bond is connected by a crosslink that does not contain a double bond, and the other of the two parts other than the single bond is connected by a crosslink that contains a double bond.
[2232] The above formula (BP15) is a structure connected by a crosslink containing double bonds in two parts other than the single bond.
[2233] In the first compound and the second compound, it is preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.
[2234] (Method for preparing the first compound)
[2235] The first compound that can be used in the organic EL device according to the present embodiment can be manufactured by a known method. In addition, the first compound can also be manufactured by using a known alternative reaction and raw materials suited to the target object according to a known method.
[2236] (Specific example of the first compound)
[2237] Specific examples of the first compound that can be used in an organic EL device according to the present embodiment include, for instance, the following compounds. However, the present invention is not limited to these specific examples of the first compound.
[2238] In the present specification, among the embodiments of the compound, D represents a deuterium atom, Me represents a methyl group, and tBu represents a tert-butyl group.
[2239] [Chemical Formula 251]
[2240]
[2241] [Chemical Formula 252]
[2242]
[2243] [Chemical Formula 253]
[2244]
[2245] [Chemical Formula 254]
[2246]
[2247] [Chemical Formula 255]
[2248]
[2249] [Chemical Formula 256]
[2250]
[2251] [Chemical Formula 257]
[2252]
[2253] [Chemical Formula 258]
[2254]
[2255] [Chemical Formula 259]
[2256]
[2257] [Chemical Formula 260]
[2258]
[2259] [Chemical Formula 261]
[2260]
[2261] [Chemical Formula 262]
[2262]
[2263] [Chemical Formula 263]
[2264]
[2265] [Chemical Formula 264]
[2266]
[2267] [Chemical Formula 265]
[2268]
[2269] [Chemical Formula 266]
[2270]
[2271] [Chemical Formula 267]
[2272]
[2273] ·2nd compound
[2274] A second compound represented by the general formula (2) according to the present embodiment will be described.
[2275] [Chemical Formula 268]
[2276]
[2277] (In the above general formula (2),
[2278] R 201 ~R 208 each independently
[2279] hydrogen atom,
[2280] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2281] Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
[2282] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2283] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2284] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2285] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[2286] -O-(R 904 The one indicated by ),
[2287] -S-(R 905 The one indicated by ),
[2288] -N(R 906 )(R 907 The one indicated by ),
[2289] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,
[2290] -C(=O)R 801 The one indicated by,
[2291] -COOR 802 The one indicated by,
[2292] Halogen atoms,
[2293] Cyanogi,
[2294] Nitro,
[2295] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2296] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[2297] L 201 and L 202 are, each independently
[2298] single bond,
[2299] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[2300] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[2301] Ar 201 and Ar 202 are, each independently
[2302] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2303] It is a complex ring-forming ring with 5 to 50 atoms, either substitutive or unsubstitutive.
[2304] (among the second compound according to the present embodiment, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are, each independently
[2305] hydrogen atom,
[2306] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2307] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2308] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2309] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[2310] R 901 If this plural exists, the plural R 901 They are identical or different from each other,
[2311] R 902 If there are multiple instances of R 902 are identical or different from each other,
[2312] R 903If this plural exists, the plural R 903 They are identical or different from each other,
[2313] R 904 If there are multiple instances of R 904 are identical or different from each other,
[2314] R 905 If there are multiple instances of R 905 are identical or different from each other,
[2315] R 906 If this plural exists, the plural R 906 They are identical or different from each other,
[2316] R 907 If this plural exists, the plural R 907 They are identical or different from each other,
[2317] R 801 If this plural exists, the plural R 801 They are identical or different from each other,
[2318] R 802 If there are multiple instances of R 802 are identical or different from each other.
[2319] In one embodiment, L 201 and L 202 Each is independently a single-bonded, or substituted or unsubstituted, ring-forming arylene group having 6 to 50 carbon atoms, and Ar 201 and Ar 202 It is preferable that each is independently a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.
[2320] In one embodiment, Ar 201 and Ar 202It is preferable that each is independently a phenyl group, a naphthyl group, a phenanthyl group, a biphenyl group, a terphenyl group, a diphenylfluorenyl group, a dimethylfluorenyl group, a benzodiphenylfluorenyl group, a benzodimethylfluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, a naphthobenzofuranyl group, or a naphthobenzothienyl group.
[2321] In one embodiment, among the second compound represented by the general formula (2), R 201 ~R 208 Each is independently a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, or -Si(R 901 )(R 902 )(R 903 It is desirable that the cause be indicated by ).
[2322] In one embodiment, L 201 is a single bond, or an unsubstituted ring-forming arylene group having 6 to 22 carbon atoms, and Ar 201 It is preferable that the silver be a substituted or unsubstituted ring-forming aryl group having 6 to 22 carbon atoms.
[2323] In one embodiment, among the second compound represented by the general formula (2), R 201 ~R 208 Each is independently a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, or -Si(R 901 )(R 902 )(R 903 It is desirable that the cause be indicated by ).
[2324] In one embodiment, among the second compound represented by the general formula (2), R 201 ~R 208 It is preferable that it be a hydrogen atom.
[2325] In one embodiment, the second compound is L in the general formula (2). 202 is a single bond, and Ar202 It is also desirable that the compound be an unsubstituted phenyl group.
[2326] In one embodiment, the second compound is L in the general formula (2). 202 is a single bond, and Ar 202 It is also desirable that the compound be an unsubstituted 2-naphthyl group.
[2327] In one embodiment, the second compound is L in the general formula (2). 202 is a single bond, and Ar 202 It is also desirable that the compound be an unsubstituted 1-naphthyl group.
[2328] In one embodiment, the second compound is L in the general formula (2). 202 is an unsubstituted p-phenylene group, and Ar 202 It is also desirable that the compound be an unsubstituted phenyl group.
[2329] In one embodiment, the second compound is L in the general formula (2). 202 is an unsubstituted m-phenylene group, and Ar 202 It is also desirable that the compound be an unsubstituted phenyl group.
[2330] In one embodiment, the second compound is L in the general formula (2). 202 is an unsubstituted o-phenylene group, and Ar 202 It is also desirable that the compound be an unsubstituted phenyl group.
[2331] In one embodiment, the second compound is L in the general formula (2). 202 is an unsubstituted p-phenylene group, and Ar 202 It is also desirable that the compound be an unsubstituted 1-naphthyl group.
[2332] In one embodiment, the second compound is L in the general formula (2). 202 is an unsubstituted p-phenylene group, and Ar 202 It is also desirable that the compound be an unsubstituted 2-naphthyl group.
[2333] In one embodiment, the second compound is L in the general formula (2). 202 ga is a non-substitutional 1,4-naphthalene diary, and Ar 202 It is also desirable that the compound be an unsubstituted phenyl group.
[2334] In one embodiment, the second compound is L in the general formula (2). 202 is an unsubstituted m-phenylene group, and Ar 202 It is also desirable that the compound be an unsubstituted 2-naphthyl group.
[2335] In one embodiment, it is also preferable that the second compound is a compound represented by the following general formula (2X).
[2336] [Chemical Formula 269]
[2337]
[2338] (In the above general formula (2X),
[2339] R 201 and R 203 ~R 208 Each is independently R in the above general formula (2). 201 and R 203 ~R 208 It has the same meaning as,
[2340] L 201 , L 202 , Ar 201 and Ar 202 are each L in the above general formula (2). 201 , L 202 , Ar 201 and Ar 202 It has the same meaning as,
[2341] L 203 is L in the above general formula (2). 201 It has the same meaning as,
[2342] L 201 , L 202 and L 203 They are identical or different from each other,
[2343] Ar203 Ar in the above general formula (2) 201 It has the same meaning as,
[2344] Ar 201 , Ar 202 and Ar 203 They are identical or different from each other.
[2345] In one embodiment, the second compound is L in the general formula (2X). 202 is a single bond, and Ar 202 It is also desirable that the compound be an unsubstituted phenyl group.
[2346] In one embodiment, the second compound is L in the general formula (2X). 202 is a single bond, and Ar 202 It is also desirable that the compound be an unsubstituted 2-naphthyl group.
[2347] In one embodiment, the second compound is L in the general formula (2X). 202 is a single bond, and Ar 202 It is also desirable that the compound be an unsubstituted 1-naphthyl group.
[2348] In one embodiment, the second compound is L in the general formula (2X). 202 is an unsubstituted p-phenylene group, and Ar 202 It is also desirable that the compound be an unsubstituted phenyl group.
[2349] In one embodiment, the second compound is L in the general formula (2X). 202 is an unsubstituted m-phenylene group, and Ar 202 It is also desirable that the compound be an unsubstituted phenyl group.
[2350] In one embodiment, the second compound is L in the general formula (2X). 202 is an unsubstituted o-phenylene group, and Ar 202 It is also desirable that the compound be an unsubstituted phenyl group.
[2351] In one embodiment, the second compound is L in the general formula (2X). 202 is an unsubstituted p-phenylene group, and Ar 202 It is also desirable that the compound be an unsubstituted 1-naphthyl group.
[2352] In one embodiment, the second compound is L in the general formula (2X). 202 is an unsubstituted p-phenylene group, and Ar 202 It is also desirable that the compound be an unsubstituted 2-naphthyl group.
[2353] In one embodiment, the second compound is L in the general formula (2X). 202 ga is a non-substitutional 1,4-naphthalene diary, and Ar 202 It is also desirable that the compound be an unsubstituted phenyl group.
[2354] In one embodiment, the second compound is L in the general formula (2X). 202 is an unsubstituted m-phenylene group, and Ar 202 It is also desirable that the compound be an unsubstituted 2-naphthyl group.
[2355] In one embodiment, the second compound is L in the general formula (2X). 201 This is a single bond, and Ar 201 It is also desirable that this be an unsubstituted phenyl group compound.
[2356] In one embodiment, the second compound is L in the general formula (2X). 201 This is a single bond, and Ar 201 It is also desirable that this be a compound with an unsubstituted 2-naphthyl group.
[2357] In one embodiment, the second compound is L in the general formula (2X). 201 This is a single bond, and Ar 201 It is also desirable that this be a compound with an unsubstituted 1-naphthyl group.
[2358] In one embodiment, the second compound is L in the general formula (2X). 201This is an unsubstituted p-phenylene group, and Ar 201 It is also desirable that this be an unsubstituted phenyl group compound.
[2359] In one embodiment, the second compound is L in the general formula (2X). 201 This is an unsubstituted m-phenylene group, and Ar 201 It is also desirable that this be an unsubstituted phenyl group compound.
[2360] In one embodiment, the second compound is L in the general formula (2X). 201 This is an unsubstituted o-phenylene group, and Ar 201 It is also desirable that this be an unsubstituted phenyl group compound.
[2361] In one embodiment, the second compound is L in the general formula (2X). 201 This is an unsubstituted p-phenylene group, and Ar 201 It is also desirable that this be a compound with an unsubstituted 1-naphthyl group.
[2362] In one embodiment, the second compound is L in the general formula (2X). 201 This is an unsubstituted p-phenylene group, and Ar 201 It is also desirable that this be a compound with an unsubstituted 2-naphthyl group.
[2363] In one embodiment, the second compound is L in the general formula (2X). 201 This is a non-substitutional 1,4-naphthalene diary, and Ar 201 It is also desirable that this be an unsubstituted phenyl group compound.
[2364] In one embodiment, the second compound is L in the general formula (2X). 201 This is an unsubstituted m-phenylene group, and Ar 201 It is also desirable that this be a compound with an unsubstituted 2-naphthyl group.
[2365] In the second compound, it is preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.
[2366] In one embodiment, the second light-emitting layer preferably contains a second compound represented by the general formula (2) as a second host material. Accordingly, for example, the second light-emitting layer contains at least 50 mass% of the total mass of the second light-emitting layer the second compound represented by the general formula (2).
[2367] In the organic EL device according to the present embodiment, among the second compound represented by the general formula (2), R is a substituent of the anthracene skeleton. 201 ~R 208 It is preferable for it to be a hydrogen atom in that it prevents the inhibition of intermolecular interactions and inhibits the decrease in electron mobility, but R 201 ~R 208 It may be a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming complex cyclic group having 5 to 50 atoms.
[2368] R 201 ~R 208 If bulky substituents such as alkyl groups and cycloalkyl groups are formed, intermolecular interactions are suppressed, and electron mobility with respect to the first host material is reduced, raising concerns that the relationship μe(H2) > μe(H1) described in the above formula (Equation 30) may not be satisfied. When the second compound is used in the second emissive layer, satisfying the relationship μe(H2) > μe(H1) can be expected to suppress the reduction in the recombination ability of holes and electrons in the first emissive layer and the reduction in luminescence efficiency. Furthermore, as substituents, haloalkyl groups, alkenyl groups, alkynyl groups, -Si(R 901 )(R 902 )(R 903 The unit indicated by ), -O-(R 904 The unit indicated by ), -S-(R 905 The unit represented by ), -N(R 906 )(R 907 The one indicated by ), Aralkill, -C(=O)R 801 The one indicated by -COOR 802There is a concern that the volume of the groups represented by , halogen atoms, cyano groups, and nitro groups may increase, and there is a concern that the volume of the alkyl groups and cycloalkyl groups may increase even more.
[2369] Among the second compound represented by the above general formula (2), R is a substituent of the anthracene skeleton 201 ~R 208 It is preferable that the substituent is not a bulky substituent, and it is preferable that it is not an alkyl group or a cycloalkyl group, and alkyl group, cycloalkyl group, haloalkyl group, alkenyl group, alkynyl group, -Si(R 901 )(R 902 )(R 903 The unit indicated by ), -O-(R 904 The unit indicated by ), -S-(R 905 The unit represented by ), -N(R 906 )(R 907 The one indicated by ), Aralkill, -C(=O)R 801 The one indicated by -COOR 802 It is more preferable that it is not a group represented by, a halogen atom, a cyano group, or a nitro group.
[2370] Among the above second compounds, R 201 ~R 208 In the case of "substituted or unsubstituted," it is preferable that the substituent does not include the aforementioned substituents that are likely to increase in volume, in particular substituted or unsubstituted alkyl groups and substituted or unsubstituted cycloalkyl groups. R 201 ~R 208 In the case of "substituted or unsubstituted," the substituent does not include a substituted or unsubstituted alkyl group and a substituted or unsubstituted cycloalkyl group, thereby preventing the suppression of intermolecular interactions caused by the presence of bulky substituents such as alkyl groups and cycloalkyl groups, and thus preventing a decrease in electron mobility. Furthermore, when such a second compound is used in the second light-emitting layer, a decrease in the recombination ability of holes and electrons in the first light-emitting layer and a decrease in luminescence efficiency can be suppressed.
[2371] R, a substituent of the anthracene skeleton 201 ~R 208 This is not a bulky substituent, but R as a substituent 201 ~R 208 It is more desirable for it to be unsubstituted. In addition, R, a substituent of the anthracene skeleton 201 ~R 208 In the case where this is not a bulky substituent, R as a non-bulky substituent 201 ~R 208 When a substituent is attached to, it is preferable that the said substituent is not a bulky substituent, and R as a substituent 201 ~R 208 The substituent bonded to is preferably not an alkyl group or a cycloalkyl group, and includes alkyl groups, cycloalkyl groups, haloalkyl groups, alkenyl groups, alkynyl groups, -Si(R 901 )(R 902 )(R 903 The unit indicated by ), -O-(R 904 The unit indicated by ), -S-(R 905 The unit represented by ), -N(R 906 )(R 907 The one indicated by ), Aralkill, -C(=O)R 801 The one indicated by -COOR 802 It is more preferable that it is not a group represented by, a halogen atom, a cyano group, or a nitro group.
[2372] (Method for preparing the second compound)
[2373] The second compound can be prepared by a known method. Additionally, the second compound can also be prepared by using a known alternative reaction and raw materials suited to the target product, according to a known method.
[2374] (Specific example of the second compound)
[2375] Specific examples of the second compound include, for instance, the following compounds. However, the present invention is not limited to these specific examples of the second compound.
[2376] [Chemical Formula 270]
[2377]
[2378] [Chemical Formula 271]
[2379]
[2380] [Chemical Formula 272]
[2381]
[2382] (Other layers of the organic EL device)
[2383] The organic EL device according to the present embodiment may have one or more organic layers in addition to the first anode-side organic layer, the second anode-side organic layer, the third anode-side organic layer, and the light-emitting layer in the light-emitting region. As for the organic layers, at least one layer selected from the group consisting of an electron injection layer, an electron transport layer, a hole barrier layer, and an electron barrier layer may be cited.
[2384] In the organic EL device according to the present embodiment, it may be ...
Claims
Claim 1 The apparatus comprises a cathode, an anode, a light-emitting region disposed between the cathode and the anode, and a hole transport band disposed between the anode and the light-emitting region, wherein the light-emitting region comprises at least one light-emitting layer, and at least one light-emitting layer in the light-emitting region comprises a light-emitting compound exhibiting light emission with a maximum peak wavelength of 500 nm or less, and at least one light-emitting layer in the light-emitting region does not comprise an iridium complex, and the hole transport band comprises at least a first anode-side organic layer, a second anode-side organic layer, and a third anode-side organic layer, wherein the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer are disposed in the order of the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer from the anode side between the anode and the light-emitting region, and the first anode-side organic layer contains a first organic material and a second organic material, wherein the first organic material and the second organic material are different from each other, and the first anode-side organic layer The content of the second organic material in the above is less than 50 mass%, the constituent material of the second anode-side organic layer is at least one compound selected from the group consisting of a compound represented by the following general formula (C1) and a compound represented by the following general formula (C3), and the constituent material of the third anode-side organic layer is a compound represented by the following general formula (C1), provided that the second anode-side organic layer contains at least one compound different from the compound contained in the third anode-side organic layer, and the difference NM2-NM3 between the refractive index NM2 at 460 nm of the constituent material included in the second anode-side organic layer and the refractive index NM3 at 460 nm of the constituent material included in the third anode-side organic layer satisfies the relationship of the following formula (Mathematical Formula N1), and the ratio of the film thickness of the second anode-side organic layer to the film thickness of the third anode-side organic layer satisfies the relationship of the following formula (Mathematical Formula A3), and the film thickness of the first anode-side organic layer,An organic electroluminescence device wherein the sum of the film thickness of the second anode-side organic layer and the film thickness of the third anode-side organic layer is 150 nm or less, and the film thickness of the third anode-side organic layer is 20 nm or more. NM2 - NM3 ≥ 0.05 … (Equation N1) 0.75 < TL3 / TL2 < 3.0 … (Equation A3) (TL2 is the film thickness of the second anode-side organic layer, TL3 is the film thickness of the third anode-side organic layer, and the unit of film thickness is nm.), (In the above general formula (C1), L A1 , L A2 and L A3 Each is independently a single bond, a substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a divalent complex cyclic group having 5 to 50 atoms forming a ring having 5 or 50 atoms, and Ar 111 , Ar 112 and Ar 113 Silver, respectively, independently forming a substituted or unsubstituted ring, an aryl group having 6–50 carbon atoms, forming a substituted or unsubstituted ring, a complex circulating group having 5–50 atoms, or -Si(R C1 )(R C2 )(R C3 ) and,R C1 , R C2 and R C3 Each is independently a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and R C1 If this plural exists, the plural R C1 are identical or different from each other, R C2 If there are multiple instances of , multiple R C2 are identical or different from each other, R C3 If this plural exists, the plural R C3 The compounds are identical or different from each other, and the compound included in the third anode-side organic layer and represented by the general formula (C1) is a monoamine compound.) (In the above general formula (C3), L C1 , L C2 , L C3 and L C4 are, respectively, a single-bonded, substituted, or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a divalent complex ring-forming group having 5 to 50 atoms, where n2 is 1, 2, 3, or 4, and when n2 is 1, L C5 is a substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming divalent complex cyclic group having 5 to 50 atoms, and when n2 is 2, 3, or 4, multiple L C5 are identical or different from each other, and if n2 is 2, 3 or 4, multiple L C5 L, which combines with each other to form a substituted or unsubstituted single ring, combines with each other to form a substituted or unsubstituted condensed ring, or does not combine with each other, does not form the substituted or unsubstituted single ring, and also does not form the substituted or unsubstituted condensed ring. C5 is a substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming divalent complex cyclic group having 5 to 50 atoms, and Ar 131 , Ar 132 , Ar 133 and Ar 134 are, respectively, independently a ring-forming aryl group having 6 to 50 carbon atoms, a ring-forming complex circulating group having 5 to 50 atoms, or -Si(R C1 )(R C2 )(R C3 ) and,R C1 , R C2 and R C3 Each is independently a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and R C1 If this plural exists, the plural R C1 are identical or different from each other, R C2 If there are multiple instances of , multiple R C2 are identical or different from each other, R C3 If this plural exists, the plural R C3 (They are identical or different from each other.) (In the compound represented by the above general formula (C1) and the compound represented by the above general formula (C3), the substituent in the case of "substituted or unsubstituted" is -N(R C6 )(R C7 It is not the one indicated by ), R C6 and R C7 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.) L of the compound represented by the general formula (C1) included in the second anode-side organic layer above. A1 , L A2 , L A3 , Ar 111 , Ar 112 , and Ar 113 All are not 1-carbazolyl groups, 2-carbazolyl groups, 3-carbazolyl groups, or 4-carbazolyl groups, and are included in the second anode-side organic layer, and L of the compound represented by the general formula (C3). C1 , L C2 , L C3 , L C4 , L C5 , Ar 131 , Ar 132 , Ar 133 and Ar 134 are not all 1-carbazolyl groups, 2-carbazolyl groups, 3-carbazolyl groups, or 4-carbazolyl groups, and are substituted or unsubstituted groups L in the compound included in the second anode-side organic layer. A1 , L A2 , L A3 , Ar 111 , Ar 112 , Ar 113 , L C1 , L C2 , L C3 , L C4 , L C5 , Ar 131 , Ar 132 , Ar 133 and Ar 134 The substituent of is not a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, or a 4-carbazolyl group. Claim 2 An organic electroluminescence element according to claim 1, wherein the first amino group represented by the following general formula (C3-1) and the second amino group represented by the following general formula (C3-2) in the compound represented by the above general formula (C3-1) are the same group. (In the above general formulas (C3-1) and (C3-2), * is L respectively C5 It is the connection location with.) Claim 3 An organic electroluminescence device according to claim 1, wherein the film thickness of the third anode-side organic layer is 20 nm or more and 60 nm or less. Claim 4 An organic electroluminescence device according to claim 1, wherein the difference NM2-NM3 between the refractive index NM2 of the constituent material included in the second anode-side organic layer and the refractive index NM3 of the constituent material included in the third anode-side organic layer satisfies the relationship of the following formula (Equation N3). NM2-NM3 ≥ 0.075 … (Equation N3) Claim 5 An organic electroluminescence device according to any one of claims 1 to 4, wherein the difference NM2-NM3 between the refractive index NM2 of the constituent material included in the second anode-side organic layer and the refractive index NM3 of the constituent material included in the third anode-side organic layer satisfies the relationship of the following formula (Equation N2). NM2-NM3 ≥ 0.10 … (Equation N2) Claim 6 An organic electroluminescence device according to any one of claims 1 to 4, wherein the compound contained in the second anode-side organic layer is different from the compound contained in the third anode-side organic layer. Claim 7 An organic electroluminescence device, wherein, in any one of claims 1 to 4, at least one compound selected from the group consisting of a compound represented by the general formula (C1) and a compound represented by the general formula (C3) has a refractive index of 1.94 or higher. Claim 8 An organic electroluminescence device according to any one of claims 1 to 4, wherein the refractive index of the compound contained in the third anode-side organic layer is 1.89 or less. Claim 9 An organic electroluminescence device according to any one of claims 1 to 4, wherein the light-emitting region contains a fluorescent light-emitting material and an organic compound. Claim 10 An organic electroluminescence device according to any one of claims 1 to 4, wherein the light-emitting region comprises one light-emitting layer. Claim 11 An organic electroluminescence device according to claim 1, wherein the light-emitting region consists of only one light-emitting layer. Claim 12 An organic electroluminescence device according to any one of claims 1 to 4, wherein the light-emitting region is composed of only two light-emitting layers. Claim 13 An organic electroluminescence device according to any one of claims 1 to 4, further comprising a fourth anode-side organic layer, wherein the fourth anode-side organic layer is disposed between the third anode-side organic layer and the light-emitting region. Claim 14 An organic electroluminescence device according to claim 13, wherein the sum of the film thickness of the first anode-side organic layer, the film thickness of the second anode-side organic layer, the film thickness of the third anode-side organic layer, and the film thickness of the fourth anode-side organic layer is 150 nm or less. Claim 15 An organic electroluminescence device according to any one of claims 1 to 4, wherein the third anode-side organic layer and the light-emitting region are in direct contact. Claim 16 delete Claim 17 An organic electroluminescence device according to any one of claims 1 to 4, wherein the sum of the film thickness of the second anode-side organic layer and the film thickness of the third anode-side organic layer is 100 nm or more. Claim 18 delete Claim 19 In any one of claims 1 to 4, the third anode-side organic layer contains a third hole transport band material which is a compound represented by the general formula (C1), and the hole mobility μh (cHT3) of the third hole transport band material is 1.0 × 10⁻⁶ -5 cm 2 An organic electroluminescence device in which / Vs is greater and the energy level HOMO(cHT3) of the highest point orbit of the third hole transport band material is -5.6 eV or less. Claim 20 In any one of claims 1 to 4, the second anode-side organic layer contains a second hole transport band material which is at least one compound selected from the group consisting of a compound represented by the general formula (C1) and a compound represented by the general formula (C3), the third anode-side organic layer contains a third hole transport band material which is a compound represented by the general formula (C1), the second hole transport band material and the third hole transport band material are different compounds, and the hole mobility μh(cHT2) of the second hole transport band material is 1.0×10 -4 cm 2 It is greater than / Vs, and the hole mobility μh(cHT3) of the above third hole transport band material is 1.0×10 -5 cm 2 An organic electroluminescence device in which / Vs is greater than, and the energy level HOMO(cHT2) of the peak point orbit of the second hole transport band material and the energy level HOMO(cHT3) of the peak point orbit of the third hole transport band material satisfy the relationship of the following formula (Equation B1). HOMO(cHT2) < HOMO(cHT3) … (Equation B1) Claim 21 An organic electroluminescence device according to any one of claims 1 to 4, wherein the third anode-side organic layer contains a third hole transport band material which is a compound represented by the general formula (C1), and the singlet energy of the third hole transport band material is greater than 3.12 eV. Claim 22 An organic electroluminescence device according to any one of claims 1 to 4, wherein the third anode-side organic layer comprises at least one compound selected from the group consisting of a compound represented by the following general formula (cHT3-11), a compound represented by the general formula (cHT3-2), a compound represented by the general formula (cHT3-31), and a compound represented by the general formula (cHT3-4). (In the above general formulas (cHT3-11), (cHT3-2), (cHT3-31) and (cHT3-4), Ar 311 is a group represented by any one of the following general formulas (1-a), (1-b), (1-c) and (1-d), and Ar 312 and Ar 313 Silver, respectively, independently forming a substituted or unsubstituted ring, an aryl group having 6–50 carbon atoms, forming a substituted or unsubstituted ring, a complex circulating group having 5–50 atoms, or -Si(R C1 )(R C2 )(R C3 ) and,R C1 , R C2 and R C3 Each is independently a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and R C1 If this plural exists, the plural R C1 are identical or different from each other, R C2 If there are multiple instances of , multiple R C2 are identical or different from each other, R C3 If this plural exists, the plural R C3 are identical or different from each other, L D1 , L D2 and L D3 Each is independently a single-bonded, substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a divalent complex cyclic group having 5 to 50 atoms forming a ring having 5 or 50 atoms, and R D26 ~R D29 One of them is L D1 It is a single bond that binds to, where *k indicates the bond position, and R D21 ~R D24 and L D1 R that is not a single bond bonding to D26 ~R D29 One or more of the groups consisting of two or more adjacent groups combine with each other to form a substituted or non-substituted single ring, combine with each other to form a substituted or non-substituted condensed ring, or do not combine with each other, R D31 ~R D38 One or more of the groups consisting of two or more adjacent groups combine with each other to form a substituted or non-substituted single ring, combine with each other to form a substituted or non-substituted condensed ring, or do not combine with each other, R D47 ~R D50 One of them is L D1 It is a single bond that binds to, and *m indicates the bond position, R D41 ~R D44 and L D1 R that is not a single bond bonding to D47 ~R D50 One or more of the groups consisting of two or more adjacent elements combine to form a substituted or unsubstituted single ring, combine to form a substituted or unsubstituted condensed ring, or do not combine with each other, where X3 is an oxygen atom, a sulfur atom, or C(R D45 )(R D46 ) and,R D45 and R D46 A group consisting of, which combines with each other to form a substituted or unsubstituted single ring, combines with each other to form a substituted or unsubstituted condensed ring, or does not combine with each other, R D25 , R which does not form the above-mentioned or unsubstituted single ring, and also does not form the above-mentioned or unsubstituted condensed ring. D21 ~R D24 , R D26 ~R D29 , R D31 ~R D38 , and R D41 ~R D50 Silver, each independently a hydrogen atom, a cyano group, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted C1–50 alkyl halide group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, -Si(R 901 )(R 902 )(R 903 The one indicated by ),-O-(R 904 A group represented by ), a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms, and R in compounds represented by the above general formulas (cHT3-11), (cHT3-2), (cHT3-31), and (cHT3-4). 901 ~R 904 Each is independently a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, a substituted or unsubstituted ring-forming C6–50 aryl group, or a substituted or unsubstituted ring-forming heterocyclic group with 5–50 atoms, and R 901 In this case, multiple Rs 901 are identical or different from each other, R 902 If there are multiple cases, multiple R 902 are identical or different from each other, R 903 In this case, multiple Rs 903 are identical or different from each other, R 904 If there are multiple cases, multiple R 904 are identical or different from each other. (Among the above general formula (1-a), R 51 ~R 55 Among them, groups consisting of two or more adjacent elements do not combine with each other, R 51 ~R 55 are each independently a hydrogen atom, or a substituted or unsubstituted C1-C6 alkyl group, and ** is L D1 Indicates the bonding position with.) (In the above general formula (1-b), R 61 ~R 68 One of them is a single bond that binds to *b, and R that is not a single bond that binds to *b. 61 ~R 68 Among them, groups consisting of two or more adjacent elements do not combine with each other, and R that is not a single combination combining to *b 61 ~R 68 Each is independently a hydrogen atom, a substituted or unsubstituted C1–C6 alkyl group, or a substituted or unsubstituted cyclic C6–C12 aryl group, and ** is L D1 Indicates the bonding position with.) (Among the above general formula (1-c), R 71 ~R 80 One of them is a single bond that binds to *d, and R that is not a single bond that binds to *d. 71 ~R 80 Among them, groups consisting of two or more adjacent elements do not all combine with each other, and are not single combinations that combine with *d R 71 ~R 80 Each is independently a hydrogen atom, a substituted or unsubstituted C1–C6 alkyl group, or a substituted or unsubstituted ring-forming C6–C12 aryl group, and ** is L D1 Indicates the bonding position with.) (of the above general formula (1-d), R 141 ~R 145 One of them is a single bond that binds to *h1, and R 141 ~R 145 The other one is a single bond that binds to *h2, not a single bond that binds to *h1, and also R that is not a single bond that binds to *h2. 141 ~R 145 Among them, groups consisting of two or more adjacent elements do not combine with each other, and R 151 ~R 155 One or more of the groups consisting of two or more adjacent groups combine with each other to form a substituted or non-substituted single ring, combine with each other to form a substituted or non-substituted condensed ring, or do not combine with each other, R 161 ~R 165 One or more of the groups consisting of two or more adjacent groups combine to form a single ring with or without substitution, or combine to form a condensed ring with or without substitution, or do not combine with each other, and are not single bonds to *h1 and are not single bonds to *h2. 141 ~R 145 , and R which does not form the above-mentioned substituted or unsubstituted single ring, and also does not form the above-mentioned substituted or unsubstituted condensed ring. 151 ~R 155 and R 161 ~R 165 are each independently a hydrogen atom, a substituted or unsubstituted C1–C6 alkyl group, or a substituted or unsubstituted cyclic C6–C12 aryl group, and ** is L D1 Indicates the bonding position with.) Claim 23 An organic electroluminescence device according to claim 22, wherein the second anode-side organic layer comprises at least one compound selected from the group consisting of a compound represented by the following general formula (cHT2-2) and a compound represented by the general formula (cHT2-3). (In the above general formulas (cHT2-2) and (cHT2-3), Ar 112 , Ar 113 , Ar 121 , Ar 122 , Ar 123 and Ar 124 are, respectively, independently a ring-forming aryl group having 6 to 50 carbon atoms, a ring-forming complex circulating group having 5 to 50 atoms, or -Si(R C1 )(R C2 )(R C3 ) and,R C1 , R C2 and R C3 Each is independently a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and R C1 If this plural exists, the plural R C1 are identical or different from each other, R C2 If there are multiple instances of , multiple R C2 are identical or different from each other, R C3 If this plural exists, the plural R C3 are identical or different from each other, L A1 , L A2 , L A3 , L B1 , L B2 , L B3 and L B4 are, respectively, a single-bonded, substituted, or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a divalent complex ring-forming group having 5 to 50 atoms, where nb is 1, 2, 3, or 4, and when nb is 1, L B5 is a substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming divalent complex cyclic group having 5 to 50 atoms, and when nb is 2, 3, or 4, multiple L B5 are identical or different from each other, and if nb is 2, 3, or 4, multiple L B5 L, which combines with each other to form a substituted or unsubstituted single ring, combines with each other to form a substituted or unsubstituted condensed ring, or does not combine with each other, does not form the substituted or unsubstituted single ring, and also does not form the substituted or unsubstituted condensed ring. B5 is a substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming divalent complex cyclic group having 5 to 50 atoms, and R A35 and R A36 A group comprising, wherein they combine with one another to form a substituted or non-substituted single ring, combine with one another to form a substituted or non-substituted condensed ring, or do not combine with one another, do not form the substituted or non-substituted single ring, and also do not form the substituted or non-substituted condensed ring R A35 and R A36 Silver, each independently a hydrogen atom, a cyano group, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted C1–50 alkyl halide group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, -Si(R 901 )(R 902 )(R 903 The one indicated by ),-O-(R 904 A group represented by ), a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming complex circulating group having 5 to 50 atoms, and R A30 ~R A34 One or more of the groups, each consisting of two or more adjacent groups, combine with one another to form a substituted or non-substituted single ring, combine with one another to form a substituted or non-substituted condensed ring, or do not combine with one another to form the said substituted or non-substituted single ring, and also do not form the said substituted or non-substituted condensed ring. A30 ~R A34 are, respectively, a hydrogen atom, a cyano group, a substituted or unsubstituted C1-50 alkyl group, a substituted or unsubstituted C1-50 alkyl halide group, a substituted or unsubstituted ring-forming C3-50 cycloalkyl group, -Si(R 901 )(R 902 )(R 903 The one indicated by ),-O-(R 904 A group represented by ), a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms, and R in the compound represented by the general formulas (cHT2-2) and (cHT2-3) above. 901 ~R 904 Each is independently a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, a substituted or unsubstituted ring-forming C6–50 aryl group, or a substituted or unsubstituted ring-forming heterocyclic group with 5–50 atoms, and R 901 In this case, multiple Rs 901 are identical or different from each other, R 902 If there are multiple cases, multiple R 902 are identical or different from each other, R 903 In this case, multiple Rs 903 are identical or different from each other, R 904 If there are multiple cases, multiple R 904 are identical or different from each other. Claim 24 An organic electroluminescence device according to any one of claims 1 to 4, wherein the second anode-side organic layer contains at least one compound selected from the group consisting of a compound represented by the general formula (cHT2-2) and a compound represented by the general formula (cHT2-3). (In the above general formulas (cHT2-2) and (cHT2-3), Ar 112 , Ar 113 , Ar 121 , Ar 122 , Ar 123 and Ar 124 are, respectively, independently a ring-forming aryl group having 6 to 50 carbon atoms, a ring-forming complex circulating group having 5 to 50 atoms, or -Si(R C1 )(R C2 )(R C3 ) and,R C1 , R C2 and R C3 Each is independently a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and R C1 If this plural exists, the plural R C1 are identical or different from each other, R C2 If there are multiple instances of , multiple R C2 are identical or different from each other, R C3 If this plural exists, the plural R C3 are identical or different from each other, L A1 , L A2 , L A3 , L B1 , L B2 , L B3 and L B4 are, respectively, a single-bonded, substituted, or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a divalent complex ring-forming group having 5 to 50 atoms, where nb is 1, 2, 3, or 4, and when nb is 1, L B5 is a substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming divalent complex cyclic group having 5 to 50 atoms, and when nb is 2, 3, or 4, multiple L B5 are identical or different from each other, and if nb is 2, 3, or 4, multiple L B5 L, which combines with each other to form a substituted or unsubstituted single ring, combines with each other to form a substituted or unsubstituted condensed ring, or does not combine with each other, does not form the substituted or unsubstituted single ring, and also does not form the substituted or unsubstituted condensed ring. B5 is a substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming divalent complex cyclic group having 5 to 50 atoms, and R A35 and R A36 A group comprising, wherein they combine with one another to form a substituted or non-substituted single ring, combine with one another to form a substituted or non-substituted condensed ring, or do not combine with one another, do not form the substituted or non-substituted single ring, and also do not form the substituted or non-substituted condensed ring R A35 and R A36 Silver, each independently a hydrogen atom, a cyano group, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted C1–50 alkyl halide group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, -Si(R 901 )(R 902 )(R 903 The one indicated by ),-O-(R 904 A group represented by ), a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming complex circulating group having 5 to 50 atoms, and R A30 ~R A34 One or more of the groups, each consisting of two or more adjacent groups, combine with one another to form a substituted or non-substituted single ring, combine with one another to form a substituted or non-substituted condensed ring, or do not combine with one another to form the said substituted or non-substituted single ring, and also do not form the said substituted or non-substituted condensed ring. A30 ~R A34 are, respectively, a hydrogen atom, a cyano group, a substituted or unsubstituted C1-50 alkyl group, a substituted or unsubstituted C1-50 alkyl halide group, a substituted or unsubstituted ring-forming C3-50 cycloalkyl group, -Si(R 901 )(R 902 )(R 903 The one indicated by ),-O-(R 904 A group represented by ), a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms, and R in the compound represented by the general formulas (cHT2-2) and (cHT2-3) above. 901 ~R 904 Each is independently a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, a substituted or unsubstituted ring-forming C6–50 aryl group, or a substituted or unsubstituted ring-forming heterocyclic group with 5–50 atoms, and R 901 In this case, multiple Rs 901 are identical or different from each other, R 902 If there are multiple cases, multiple R 902 are identical or different from each other, R 903 In this case, multiple Rs 903 are identical or different from each other, R 904 If there are multiple cases, multiple R 904 are identical or different from each other. Claim 25 An organic electroluminescence element, wherein, in any one of claims 1 to 4, the compound represented by the general formula (C1) is a monoamine compound. Claim 26 An organic electroluminescence device according to any one of claims 1 to 4, comprising two or more light-emitting units and one or more charge-generating layers disposed between the two or more light-emitting units, wherein at least one of the two or more light-emitting units is a first light-emitting unit comprising a hole transport band as a first hole transport band and a light-emitting region as a first light-emitting region. Claim 27 An organic electroluminescence display device having an anode and a cathode arranged facing each other, a blue organic EL element as a blue pixel, a green organic EL element as a green pixel, and a red organic EL element as a red pixel, wherein the blue pixel includes an organic electroluminescence element described in any one of claims 1 to 4 as the blue organic EL element, wherein the green organic EL element has a green light-emitting region arranged between the anode and the cathode, and the red organic EL element has a red light-emitting region arranged between the anode and the cathode, and wherein the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer are installed in common across the blue organic EL element, the green organic EL element, and the red organic EL element between the light-emitting region, the green light-emitting region, and the red light-emitting region of the blue organic EL element, respectively, and the anode. Claim 28 An organic electroluminescence display device having an anode and a cathode arranged facing each other, a blue organic EL element as a blue pixel, a green organic EL element as a green pixel, and a red organic EL element as a red pixel, wherein the blue pixel, the green pixel, and the red pixel each include an organic electroluminescence element described in any one of claims 1 to 4 as the blue organic EL element, the green organic EL element, and the red organic EL element, respectively; wherein the light-emitting region in the blue organic EL element is a blue light-emitting region arranged between the anode and the cathode, the light-emitting region in the green organic EL element is a green light-emitting region arranged between the anode and the cathode, and the light-emitting region in the red organic EL element is a red light-emitting region arranged between the anode and the cathode, and wherein the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer are the blue light-emitting region, the green light-emitting region, and the red light-emitting region An organic electroluminescence display device installed in common across the blue organic EL element, the green organic EL element, and the red organic EL element between each and the anode. Claim 29 An electronic device equipped with an organic electroluminescence element described in any one of claims 1 to 4. Claim 30 An organic electroluminescence element according to any one of claims 1 to 4, wherein the compound represented by the general formula (C1) included in the third anode-side organic layer comprises a group represented by the following general formula (2-e), and the group represented by the general formula (2-e) is directly bonded to, bonded through a phenylene group, or bonded through a biphenylene group to the nitrogen atom of the amino group of the monoamine compound. (In the above general formula (2-e), Z3 is an oxygen atom, a sulfur atom, NR 319 or C(R 320 )(R 321 ) and,R 311 ~R 321 One of them is a single bond that bonds to *e, and R 311 ~R 321 One of them is a single bond that binds to *e, or R 311 ~R 318 Among the following substituted or unsubstituted benzene rings formed by the bonding of two or more adjacent groups, one carbon atom is bonded to *e by a single bond, and R, which is not bonded to *e by a single bond. 311 ~R 318 A group consisting of two or more adjacent groups, which combine to form a substituted or unsubstituted benzene ring, or do not combine to each other, and are not single bonds that combine with *e, and also do not form the said substituted or unsubstituted benzene ring, R 311 ~R 318 Each is independently a hydrogen atom, a substituted or unsubstituted C1–C6 alkyl group, a substituted or unsubstituted ring-forming C6–C12 aryl group, or a substituted or unsubstituted ring-forming heterocyclic group with 5–C10 atoms, and R that is not a single bond bonded to *e 319 is a hydrogen atom, a substituted or unsubstituted C1–C6 alkyl group, or a substituted or unsubstituted ring-forming C6–C12 aryl group, and R that is not a single bond bonded to *e 320 and R 321 A group comprising, which combines with each other to form a substituted or unsubstituted single ring, or combines with each other to form a substituted or unsubstituted condensed ring, or does not combine with each other, and is not a single bond that combines with *e, and also does not form the said substituted or unsubstituted single ring, and also does not form the said substituted or unsubstituted condensed ring R 320 and R 321 Each is independently a hydrogen atom, a substituted or unsubstituted C1–C6 alkyl group, or a substituted or unsubstituted ring-forming C6–C12 aryl group, and ** indicates the bonding position.) Claim 31 An organic electroluminescence device according to any one of claims 1 to 4, wherein the light-emitting region does not include a heavy metal complex. Claim 32 An organic electroluminescence device according to any one of claims 1, 2 and 4, wherein the at least one light-emitting layer of the light-emitting region further comprises a second compound, and the second compound is represented by the following general formula (2). (In the above general formula (2), R 201 ~R 208 Silver, each independently a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted C1–50 haloalkyl group, a substituted or unsubstituted C2–50 alkenyl group, a substituted or unsubstituted C2–50 alkynyl group, a substituted or unsubstituted C2–50 cycloalkyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, -Si(R 901 )(R 902 )(R 903 The one indicated by ),-O-(R 904 The element indicated by ),-S-(R 905 The unit represented by ), -N(R 906 )(R 907 A group represented by ), a substituted or unsubstituted aralkyl group with 7–50 carbon atoms, -C(=O)R 801 The one indicated by, -COOR 802 A group represented by, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming complex circulating group having 5 to 50 atoms, and L 201 and L 202 are, respectively, independently a single-bonded, substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a divalent complex cyclic group having 5 to 50 atoms forming a single-bonded or unsubstituted ring, and Ar 201 and Ar 202 is, respectively, an independently substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms. R in the second compound 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each is independently a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, a substituted or unsubstituted ring-forming C6–50 aryl group, or a substituted or unsubstituted ring-forming heterocyclic group with 5–50 atoms, and R 901 In this case, multiple Rs 901 are identical or different from each other, R 902 If there are multiple cases, multiple R 902 are identical or different from each other, R 903 In this case, multiple Rs 903 are identical or different from each other, R 904 If there are multiple cases, multiple R 904 are identical or different from each other, R 905 If there are multiple cases, multiple R 905 are identical or different from each other, R 906 In this case, multiple Rs 906 are identical or different from each other, R 907 In this case, multiple Rs 907 are identical or different from each other, R 801 In this case, multiple Rs 801 are identical or different from each other, R 802 If there are multiple cases, multiple R 802 are identical or different from each other. Claim 33 An organic electroluminescence device according to claim 32, wherein the film thickness of the third anode-side organic layer is 20 nm or more and 75 nm or less. Claim 34 In any one of claims 1 to 4, the first anode-side organic layer comprises a compound represented by the general formula (C1) as the first organic material, and L of the compound represented by the general formula (C1) is included in the first anode-side organic layer. A1 , L A2 , L A3 , Ar 111 , Ar 112 , and Ar 113 ...are not all 1-carbazolyl groups, 2-carbazolyl groups, 3-carbazolyl groups, or 4-carbazolyl groups, and are substituted or unsubstituted groups L in the compound included in the first anode-side organic layer. A1 , L A2 , L A3 , Ar 111 , Ar 112 and Ar 113 The substituent is not a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, or a 4-carbazolyl group, and is included in the third anode-side organic layer, and L of the compound represented by the general formula (C1). A1 , L A2 , L A3 , Ar 111 , Ar 112 , and Ar 113 ...are not all 1-carbazolyl groups, 2-carbazolyl groups, 3-carbazolyl groups, or 4-carbazolyl groups, and are substituted or unsubstituted groups L in the compound included in the third anode-side organic layer. A1 , L A2 , L A3 , Ar 111 , Ar 112 and Ar 113 The substituent is an organic electroluminescent element that is not a 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, or 4-carbazolyl group.