Condensed ring compound, organic light-emitting device and display device comprising the same
By using condensation ring compounds with high bond dissociation energy as organic layer materials in organic light-emitting devices, the decomposition problem caused by the amine or carbazole moiety in the prior art is solved, thereby improving the stability and lifespan of the device.
Patent Information
- Application Number
- CN201911049848.2
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2018-12-17
- Filing Date
- 2019-10-31
- Publication Date
- 2025-01-10
- Estimated Expiration
- 2039-10-31
AI Technical Summary
In existing organic light-emitting devices, compounds containing amine or carbazole moieties are prone to decomposition in the excited state, leading to a shortened device lifespan. Furthermore, existing technologies struggle to effectively improve the stability and lifespan of these devices.
Using condensed ring compounds with high bond dissociation energy as organic layer materials, including in the emitter layer or as a coating material, avoids the use of amine and carbazole moieties, improves the stability of the compound, and enhances device lifespan.
By using condensation ring compounds with high bond dissociation energy, the lifetime and stability of organic light-emitting devices are improved, the risk of decomposition in the excited state is reduced, and the lifespan of the devices is increased.
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Figure CN111320627B_ABST
Abstract
Description
[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2018-0163316 filed in the Korean Intellectual Property Office on December 17, 2018, the entire contents of which are incorporated herein by reference. Technical Field
[0002] One or more embodiments of the present disclosure relate to a condensed ring compound, an organic light-emitting device including the condensed ring compound, and a display device including the organic light-emitting device. Background Art
[0003] The organic light emitting device is a self-emitting device having a wide viewing angle, a high contrast ratio, a short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed, and produces a full-color image.
[0004] An example of such an organic light-emitting device may include a first electrode located on a substrate and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially located on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers such as holes and electrons recombine in the emission layer to generate excitons. These excitons transition (e.g., transition or relax) from an excited state to a ground state, thereby generating light. Summary of the invention
[0005] One or more embodiments include a condensed ring compound, an organic light emitting device including the condensed ring compound, and a display apparatus including the organic light emitting device.
[0006] Additional aspects of the embodiments will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the presented embodiments.
[0007] One aspect of an embodiment of the present disclosure provides a condensed ring compound represented by Formula 1:
[0008] Formula 1
[0009] (A 11 ) n11 -(L 11 ) a11 -(A 12 ) n12 .
[0010] In formula 1,
[0011] L 11 Can be selected from substituted or unsubstituted C 5 -C 60 Carbocyclic group and substituted or unsubstituted C1 -C 60 Heterocyclic group,
[0012] a11 can be an integer from 0 to 5,
[0013] A 11 and A 12 may be independently selected from the group represented by Formula 1A and the group represented by Formula 1B, and
[0014] n11 and n12 may each independently be an integer from 1 to 3:
[0015]
[0016] In Formula 1A and Formula 1B,
[0017] X 11 Can be selected from C(R 14 )(R 15 )、Si(R 14 )(R 15 ), O and S,
[0018] X 12 Can be selected from C(R 16 )(R 17 )、Si(R 16 )(R 17 ), O and S,
[0019] R 11 To R 17 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ),
[0020] b11 can be selected from 1 and 2,
[0021] b12 and b13 may each independently be an integer from 1 to 3,
[0022] Q 1 To Q 3 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group, and
[0023] *Indicates the binding site with the adjacent atom.
[0024] Another aspect of an embodiment of the present disclosure provides an organic light-emitting device, comprising: a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode and including an emission layer, wherein the organic layer comprises the condensed ring compound described above.
[0025] Another aspect of an embodiment of the present disclosure provides a display device, comprising: a thin film transistor, including a source electrode, a drain electrode and an active layer; and an organic light-emitting device described above, wherein a first electrode of the organic light-emitting device is electrically coupled to one selected from the source electrode and the drain electrode of the thin film transistor. BRIEF DESCRIPTION OF THE DRAWINGS
[0026] These and / or other aspects of the embodiments will become apparent and more readily understood through the following description of the embodiments in conjunction with the accompanying drawings, in which:
[0027] Figure 1 is a schematic cross-sectional view of an organic light emitting device according to an embodiment;
[0028] Figure 2 is a schematic cross-sectional view of an organic light emitting device according to an embodiment;
[0029] Figure 3 is a schematic cross-sectional view of an organic light emitting device according to an embodiment; and
[0030] Figure 4 is a schematic cross-sectional view of an organic light emitting device according to an embodiment. DETAILED DESCRIPTION
[0031] The subject matter of the present disclosure will now be more fully described with reference to exemplary embodiments. However, the disclosed subject matter can be implemented in many different forms and should not be construed as being limited to the embodiments set forth herein; on the contrary, these embodiments are provided so that the present disclosure will be thorough and complete and will fully convey the disclosed subject matter to those skilled in the art. The features of the embodiments of the present disclosure and how to implement them will become apparent by reference to the embodiments and drawings that will be described in more detail below. However, the disclosed subject matter can be implemented in many different forms and should not be limited to exemplary embodiments.
[0032] Hereinafter, the embodiments are described in more detail by referring to the accompanying drawings, and in the drawings, like reference numerals denote like elements and redundant explanations thereof will not be repeated here.
[0033] As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise.
[0034] It will also be understood that the term "comprises" and / or variations thereof as used herein specify the presence of the stated features or components, but do not exclude the presence or addition of one or more other features or components. As used herein, the term "and / or" includes any and all combinations of one or more of the relevant listed items. When a statement such as "at least one of..." follows a list of elements, it modifies the entire list of elements, rather than the individual elements in the list.
[0035] It will be understood that when a layer, region, or component is referred to as being "on" or "onto" another layer, region, or component, the layer, region, or component may be formed directly or indirectly on the other layer, region, or component. For example, there may be intervening layers, regions, or components. In addition, it will be understood that when an element or layer is referred to as being "between" two elements or layers, the element or layer may be the only element or layer between the two elements or layers, or one or more intervening elements or layers may also be present.
[0036] For the convenience of explanation, the size of the components in the drawings may be exaggerated. In other words, since the size and thickness of the components in the drawings may be arbitrarily shown for the convenience of explanation, the following embodiments of the present disclosure are not limited thereto.
[0037] The term "organic layer" as used herein refers to a single layer and / or multiple layers between the first electrode and the second electrode of the organic light emitting device. The material included in the "organic layer" is not limited to an organic material. For example, the organic layer may include an inorganic material.
[0038] The condensed ring compound according to the embodiment is represented by Formula 1:
[0039] Formula 1
[0040] (A 11 ) n11 -(L 11 ) a11 -(A 12 ) n12
[0041] In formula 1, L 11 Can be selected from substituted or unsubstituted C 5 -C 60 Carbocyclic group and substituted or unsubstituted C 1 -C 60 Heterocyclic group.
[0042] For example, in Formula 1, L 11 Can be selected from:
[0043] C 5 -C 60 Carbocyclyl; and
[0044] The substitution is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 6 -C 30 C of at least one of an aryl group and a monovalent non-aromatic condensed polycyclic group 5 -C 60 Carbocyclic group.
[0045] In one embodiment, in Formula 1, L 11 Can be selected from:
[0046] Phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl and peryl; and
[0047] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, at least one of phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, The cyclopentyl and peryl groups.
[0048] In one embodiment, in Formula 1, L 11 It may be selected from the groups represented by Formula 4-1 to Formula 4-35, but the embodiments of the present disclosure are not limited thereto:
[0049]
[0050]
[0051] In equations 4-1 to 4-35,
[0052] X 41 It can be C(R 43 )(R 44 ),
[0053] R 41 To R 44 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl and peryl,
[0054] b41 can be selected from 1, 2, 3 and 4,
[0055] b42 can be selected from 1, 2, 3, 4, 5 and 6,
[0056] b43 can be selected from 1, 2, 3, 4, 5, 6, 7 and 8,
[0057] b44 can be selected from 1, 2, 3, 4 and 5,
[0058] b45 can be selected from 1, 2 and 3,
[0059] b46 can be selected from 1 and 2, and
[0060] * and *' both refer to the binding sites with adjacent atoms.
[0061] In one embodiment, in Formula 1, L 11 It may be selected from the groups represented by Formula 4-1 to Formula 4-17, but the embodiments of the present disclosure are not limited thereto.
[0062] In one embodiment, in Formula 1, L 11It may be selected from the groups represented by Formula 4-1 to Formula 4-12, but the embodiments of the present disclosure are not limited thereto.
[0063] In formula 1, a11 refers to L 11 The number of repetitions of L1 and L2 may be an integer from 0 to 5. When a11 is two or more, two or more L 11 May be the same as or different from each other.
[0064] For example, in Formula 1, a11 may be selected from 0, 1, and 2, but the embodiments of the present disclosure are not limited thereto.
[0065] In formula 1, A 11 and A 12 may be independently selected from the group represented by Formula 1A and the group represented by Formula 1B:
[0066]
[0067] In Formula 1A and Formula 1B, X 11 , X 12 , R 11 To R 13 and b11 to b13 may each be independently the same as described below, and * indicates a binding site with an adjacent atom.
[0068] In Formula 1A and Formula 1B, X 11 Can be selected from C(R 14 )(R 15 )、Si(R 14 )(R 15 ), O and S.
[0069] For example, in Formula 1A and Formula 1B, X 11 It can be C(R 14 )(R 15 ), but the embodiments of the present disclosure are not limited thereto.
[0070] In Formula 1A and Formula 1B, X 12 Can be selected from C(R 16 )(R 17 )、Si(R 16 )(R 17 ), O and S.
[0071] In Formula 1A and Formula 1B, X 12 It can be C(R 16 )(R 17 ), but the embodiments of the present disclosure are not limited thereto.
[0072] In Formula 1A and Formula 1B, R 11 To R 17can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ),and
[0073] Q 1 To Q3 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, a monovalent nonaromatic condensed polycyclic group, a monovalent nonaromatic condensed heteropolycyclic group, a biphenyl group and a terphenyl group.
[0074] For example, in Formula 1A and Formula 1B, R 11 To R 17 Can be independently selected from:
[0075] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;
[0076] The C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;
[0077] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, and pentacene; and
[0078] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, at least one of cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, The invention also includes phenyl, peryl, and pentacene, but the embodiments of the present disclosure are not limited thereto.
[0079] In one embodiment, in Formula 1A and Formula 1B, R 11 To R 17 Can be independently selected from:
[0080] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 alkyl;
[0081] C substituted with at least one selected from deuterium, -F, -Cl, -Br, -I and cyano 1 -C 20 Alkyl; and
[0082] The groups represented by Formula 5-1 to Formula 5-9, but the embodiments of the present disclosure are not limited thereto:
[0083]
[0084] In Formula 5-1 to Formula 5-9,
[0085] R 51 and R 52 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl and peryl,
[0086] b51 can be selected from 1, 2, 3, 4 and 5,
[0087] b52 can be selected from 1, 2, 3, 4, 5, 6 and 7,
[0088] b53 can be selected from 1, 2, 3, 4, 5, 6, 7, 8 and 9,
[0089] b54 may be selected from 1, 2, 3 and 4, and
[0090] *Indicates the binding site with the adjacent atom.
[0091] In one embodiment, in Formula 1A and Formula 1B, R 11 To R 17 Can be independently selected from:
[0092] hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl;
[0093] methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl, each of which is substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I and cyano; and
[0094] The groups represented by Formula 6-1 to Formula 6-74, but the embodiments of the present disclosure are not limited thereto:
[0095]
[0096]
[0097]
[0098] In equations 6-1 to 6-74,
[0099] i-Pr refers to isopropyl,
[0100] t-Bu refers to tert-butyl,
[0101] Ph refers to phenyl,
[0102] 1-Naph refers to 1-naphthyl,
[0103] 2-Naph means 2-naphthyl, and
[0104] *Indicates the binding site with the adjacent atom.
[0105] In Formula 1A and Formula 1B, b11 may be selected from 1 and 2.
[0106] In Formula 1A and Formula 1B, b12 and b13 may each independently be an integer of 1 to 3.
[0107] In one embodiment, in Formula 1, A 11 and A 12 Each may be independently a group represented by Formula 1A, but the embodiments of the present disclosure are not limited thereto.
[0108] In formula 1, n11 refers to A 11 The number of substitutions, n12 refers to A 12 The substitution number of n11 and n12 may each independently be an integer of 1 to 3.
[0109] For example, in Formula 1, n11 and n12 may be each independently selected from 1 and 2, but the embodiments of the present disclosure are not limited thereto.
[0110] In one embodiment, in Formula 1, the sum of n11 and n12 may be selected from 2 and 3, but the embodiments of the present disclosure are not limited thereto.
[0111] In one embodiment, in Formula 1, n11 and n12 may both independently be 1, but embodiments of the present disclosure are not limited thereto.
[0112] In one embodiment, in Formula 1, L 11 may be selected from the groups represented by Formulae 4-1 to 4-12, and a11 may be selected from 0, 1, and 2, but the embodiments of the present disclosure are not limited thereto.
[0113] In one embodiment, the condensed ring compound may be represented by one selected from Formula 1-1 and Formula 1-2, but the embodiments of the present disclosure are not limited thereto:
[0114] Formula 1-1
[0115]
[0116] Formula 1-2
[0117]
[0118] In formula 1-1 and formula 1-2,
[0119] L 11 and a11 may be independently the same as defined in Formula 1,
[0120] X 11a and X 11b can be independently combined with X in formula 1A 11The same definition,
[0121] X 12a and X 12b can be independently combined with X in formula 1A 12 The same definition,
[0122] R 11a , R 11b , R 12a , R 12b , R 13a and R 13b can be independently combined with R in formula 1A 11 The same definition,
[0123] b11a and b11b may each independently be the same as defined in conjunction with b11 in Formula 1A, and
[0124] b12a, b12b, b13a and b13b may each independently be the same as defined in conjunction with b12 in Formula 1A.
[0125] In one embodiment, the condensed ring compound may be represented by one selected from Formula 1-11 and Formula 1-12, but the embodiments of the present disclosure are not limited thereto:
[0126] Formula 1-11
[0127]
[0128] Formula 1-12
[0129]
[0130] In formula 1-11 and formula 1-12,
[0131] L 11 It can be selected from the groups represented by Formula 4-1 to Formula 4-12;
[0132]
[0133]
[0134] In equations 4-1 to 4-12,
[0135] R 41 It can be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl and peryl,
[0136] b41 can be selected from 1, 2, 3 and 4,
[0137] b42 can be selected from 1, 2, 3, 4, 5 and 6,
[0138] * and *' both refer to the binding sites with adjacent atoms.
[0139] a11 can be selected from 0, 1 and 2,
[0140] R 11a , R 11b , R 12a , R 12b , R 13a , R 13b , R 14a , R 14b , R 15a , R 15b , R 16a , R 16b , R 17a and R 17b can be independently combined with R in formula 1A 11 The same definition,
[0141] b11a and b11b may each independently be the same as defined in conjunction with b11 in Formula 1A, and
[0142] b12a, b12b, b13a and b13b may each independently be the same as defined in conjunction with b12 in Formula 1A.
[0143] In one embodiment, the condensed ring compound can be selected from Compound 1 to Compound 6, but the embodiments of the present disclosure are not limited thereto:
[0144]
[0145] In some embodiments, the condensed ring compound does not include an amine moiety and a carbazole moiety. For example, in some embodiments, the condensed ring compound does not have an amine moiety and / or a carbazole moiety.
[0146] Generally, an amine moiety or a carbazole moiety has high hole transport properties, but includes a carbon-nitrogen single bond with a relatively low bond dissociation energy (BDE). Therefore, in a compound including an amine moiety and / or a carbazole moiety, molecular stability may be low. Because a compound including an amine moiety or a carbazole moiety receives electrons in an excited state and decomposes, the life of an organic light-emitting device including the compound may be shortened or reduced.
[0147] On the other hand, because the condensed ring compound has a relatively high BDE, the lifetime of the organic light-emitting device including the condensed ring compound can be improved. As used herein, the term "bond dissociation energy" or "BDE" refers to the energy required for the homolysis of a chemical bond (e.g., a covalent chemical bond). In the disclosed embodiments, "lowest bond dissociation energy" or "lowest BDE" refers to the energy required for the homolysis of a chemical bond with the lowest bond dissociation energy of a condensed ring compound. For example, in some embodiments, the bond dissociation energy disclosed herein refers to the bond dissociation energy of a carbon-nitrogen bond of a condensed ring compound. In some embodiments, the bond dissociation energy disclosed herein refers to A 11 , A 12 , the bond dissociation energy of the carbon-nitrogen bond of Formula 1A or Formula 1B.
[0148] In some embodiments, the BDE of the condensed ring compound may be equal to or exceed (e.g., greater than) about 1.8 eV (e.g., 3.0 eV or greater), but the embodiments of the present disclosure are not limited thereto. For example, the lowest BDE of the condensed ring compound is in the range of 1.8 eV to 10.0 eV, 3.0 eV to 10.0 eV, or, for example, 3.5 eV to 10.0 eV. When the BDE of the condensed ring compound is within this range, an organic light-emitting device with a usable level of life can be provided.
[0149] The condensed ring compound represented by Formula 1 may be synthesized by using any suitable organic synthesis method commonly used in the art. After reading the following description of example embodiments, a person of ordinary skill may recognize the synthesis method of the condensed ring compound.
[0150] At least one of the condensed ring compounds of Formula 1 may be used between a pair of electrodes of an organic light emitting device. For example, the condensed ring compound may be included in at least one layer selected from a hole transport region, an electron transport region, and an emission layer.
[0151] In one or more embodiments, the condensed ring compound of Formula 1 may be used as a material of a capping layer located outside a pair of electrodes of an organic light emitting device.
[0152] In one embodiment, the emission layer may include the condensed ring compound, but the embodiments of the present disclosure are not limited thereto. In one embodiment, the emission layer may also include a phosphorescent dopant or a delayed fluorescent dopant. In this case, the condensed ring compound may be used as a host.
[0153] In one embodiment, the first electrode may be an anode,
[0154] The second electrode may be a cathode,
[0155] The organic layer may further include a hole transport region between the first electrode and the emission layer and / or an electron transport region between the emission layer and the second electrode.
[0156] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof, and
[0157] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0158] For example, the electron blocking layer may include the condensed ring compound. In one embodiment, the emission layer may include a host and may satisfy condition 1, but embodiments of the present disclosure are not limited thereto:
[0159] Condition 1
[0160] BDE(C - )>T 1 (H).
[0161] In condition 1,
[0162] BDE(C - ) is the bond dissociation energy when the condensed ring compound is in an anionic state and the bond is dissociated by the excitation energy of the adjacent host, and
[0163] T 1 (H) is the lowest excited triplet energy level of the host.
[0164] On the other hand, the electron blocking layer may include the condensed ring compound, and the emission layer may include the host and satisfy Condition 2, but embodiments of the present disclosure are not limited thereto:
[0165] Condition 2
[0166] |HOMO(H)-HOMO(C)|≤0.3eV.
[0167] In condition 2,
[0168] HOMO(H) is the highest occupied molecular orbital energy level of the host,
[0169] HOMO (C) is the highest occupied molecular orbital energy level of a condensed ring compound.
[0170] Since the organic light emitting device satisfying Condition 2 has improved hole injection characteristics from the electron blocking layer to the host, the life span of the organic light emitting device may be improved.
[0171] The expression “(organic layer) includes at least one condensed ring compound” as used herein may include the case where “(organic layer) includes the same condensed ring compound represented by Formula 1” and the case where “(organic layer) includes two or more different condensed ring compounds represented by Formula 1”.
[0172] For example, the organic layer may include only compound 1 as a condensed ring compound. In this regard, compound 1 may be present in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include compound 1 and compound 2 as condensed ring compounds. In this regard, compound 1 and compound 2 may be present in the same layer (for example, compound 1 and compound 2 may all be present in the emission layer), or in different layers (for example, compound 1 may be present in the emission layer, and compound 2 may be present in the electron transport layer).
[0173] The organic layer includes: i) a hole transport region located between the first electrode (anode) and the emission layer and including at least one of a hole injection layer, a hole transport layer, a buffer layer, and an electron blocking layer; and ii) an electron transport region located between the emission layer and the second electrode (cathode) and including at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer. The emission layer may include at least one of the condensed ring compounds represented by Formula 1.
[0174] As used herein, the term "organic layer" refers to a single layer and / or multiple layers between the first electrode and the second electrode of the organic light-emitting device. The material included in the "organic layer" is not limited to an organic material. For example, the organic layer may include an inorganic material.
[0175] Figure 1 Description
[0176] Figure 1 1 is a schematic diagram of an organic light emitting device 10 according to an embodiment. The organic light emitting device 10 includes a first electrode 110 , an organic layer 150 , and a second electrode 190 .
[0177] In the following, we will combine Figure 1 A structure of an organic light emitting device 10 and a method of manufacturing the organic light emitting device 10 according to an embodiment are described.
[0178] First electrode 110
[0179] exist Figure 1 In the embodiment, the substrate may be additionally located under the first electrode 110 or on the second electrode 190. The substrate may be a glass substrate or a plastic substrate, both of which have excellent mechanical strength, thermal stability, transparency, surface flatness, easy handling, and waterproofness.
[0180] The first electrode 110 may be formed by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for the first electrode 110 may be selected from materials having a high work function to facilitate hole injection.
[0181] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and any combination thereof, but the embodiments of the present disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode 110 may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but the embodiments of the present disclosure are not limited thereto.
[0182] The first electrode 110 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited thereto.
[0183] Organic layer 150
[0184] The organic layer 150 is located on the first electrode 110. The organic layer 150 may include an emission layer.
[0185] The organic layer 150 may further include a hole transport region between the first electrode 110 and the emission layer and / or an electron transport region between the emission layer and the second electrode 190 .
[0186] Hole transport region in the organic layer 150
[0187] The hole transport region may have: i) a single layer structure including a single layer including a single material; ii) a single layer structure including a single layer including a plurality of different materials; or iii) a multilayer structure having a plurality of layers including a plurality of different materials.
[0188] The hole transport region may include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an emission assisting layer, and an electron blocking layer.
[0189] For example, the hole transport region may have: a single-layer structure including a single layer comprising a plurality of different materials; or a multi-layer structure having a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure or a hole injection layer / hole transport layer / emission assisting layer structure, wherein, for each structure, the constituent layers are stacked sequentially from the first electrode 110 in the order stated, but the structure of the hole transport region is not limited thereto.
[0190] The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201, and a compound represented by Formula 202:
[0191]
[0192] Formula 201
[0193]
[0194] Formula 202
[0195]
[0196] In equation 201 and equation 202,
[0197] L 201 To L 204 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0198] L 205 Can be selected from *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C 1 -C 20 Alkylene, substituted or unsubstituted C 2 -C 20 Alkenylene, substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0199] xa1 to xa4 may each independently be an integer from 0 to 3,
[0200] xa5 can be an integer from 1 to 10, and
[0201] R 201 To R 204 and Q 201 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
[0202] In one embodiment, in Formula 202, R 201 and R 202 can be optionally linked via a single bond, a dimethyl-methylene or a diphenyl-methylene, R 203 and R 204 Attachment may alternatively be via a single bond, a dimethyl-methylene group or a diphenyl-methylene group.
[0203] In one embodiment, in equation 201 and equation 202,
[0204] L 201 To L 205 Can be independently selected from:
[0205] Phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, tetraphenylene, perylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, rubidinylene, camphenylene, ovaphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene, and pyridinylene; and
[0206] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 Alkyl phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ) is at least one of phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalene, indacenylene, acenaphthenylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, tetraphenylene, perylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, rubidinylene, camphenylene, ovaphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene and pyridylene, and
[0207] Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0208] In one or more embodiments, xa1 to xa4 may each independently be 0, 1 or 2.
[0209] In one or more embodiments, xa5 can be 1, 2, 3 or 4.
[0210] In one or more embodiments, R 201 To R 204 and Q 201 Can be independently selected from:
[0211] Phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, and pyridyl; and
[0212] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 Alkyl phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ) is phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl and pyridyl, and
[0213] Q 31 To Q 33 Same as described above.
[0214] In one or more embodiments, in Formula 201, from R 201 To R 203 At least one of the selected ones can be independently selected from:
[0215] fluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; and
[0216] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 an alkyl group of phenyl, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group,
[0217] However, the embodiments of the present disclosure are not limited thereto.
[0218] In one or more embodiments, in Formula 202, i) R 201 and R 202 can be connected via a single bond, and / or ii) R 203 and R 204 Connection can be made via a single button.
[0219] In one or more embodiments, in Formula 202, from R 201 To R 204 At least one of the selected ones may be selected from:
[0220] carbazolyl; and
[0221] The substitution is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 a carbazolyl group selected from at least one of a phenyl group, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,
[0222] However, the embodiments of the present disclosure are not limited thereto.
[0223] The compound represented by Formula 201 can be represented by Formula 201A:
[0224] Formula 201A
[0225]
[0226] In one embodiment, the compound represented by Formula 201 may be represented by Formula 201A(1), but embodiments of the present disclosure are not limited thereto:
[0227] Formula 201A(1)
[0228]
[0229] In one embodiment, the compound represented by Formula 201 may be represented by Formula 201A-1, but embodiments of the present disclosure are not limited thereto:
[0230] Formula 201A-1
[0231]
[0232] In one embodiment, the compound represented by Formula 202 can be represented by Formula 202A:
[0233] Formula 202A
[0234]
[0235] In one or more embodiments, the compound represented by Formula 202 can be represented by Formula 202A-1:
[0236] Formula 202A-1
[0237]
[0238] In Formula 201A, Formula 201A(1), Formula 201A-1, Formula 202A, and Formula 202A-1,
[0239] L 201 To L 203 , xa1 to xa3, xa5 and R 202 To R 204 Same as described above,
[0240] R 211 and R 212 can be independently combined with R 203 The same definition,
[0241] R 213 To R 217 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 Alkyl phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl and pyridyl.
[0242] The hole transport region may include at least one compound selected from Compound HT1 to Compound HT39, but the embodiments of the present disclosure are not limited thereto:
[0243]
[0244]
[0245]
[0246] The thickness of the hole transport region can be approximately To about In the range of, for example, about To about When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be in the range of about To about In the range of, for example, about To about In the range of To about In the range of, for example, about To about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, suitable or satisfactory hole transport characteristics may be obtained without significantly increasing the driving voltage.
[0247] The emission auxiliary layer can improve light emitting efficiency by compensating the optical resonance distance according to the wavelength of light emitted by the emission layer, and the electron blocking layer can block the flow of electrons from the electron transport region. The emission auxiliary layer and the electron blocking layer may include materials as described above.
[0248] p-dopant
[0249] In addition to the above materials, the hole transport region may further include a charge generating material for improving the conductive property. The charge generating material may be dispersed uniformly or non-uniformly in the hole transport region.
[0250] The charge generating material may be, for example, a p-dopant.
[0251] In one embodiment, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of approximately -3.5 eV or less.
[0252] The p-dopant may include at least one selected from quinone derivatives, metal oxides, and cyano-containing compounds, but the embodiments of the present disclosure are not limited thereto.
[0253] For example, the p-dopant may include at least one selected from the following compounds:
[0254] Quinone derivatives, such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);
[0255] Metal oxides, such as tungsten oxide or molybdenum oxide;
[0256] 1,4,5,8,9,12-Hexaazatriphenylene-hexanitrile (HAT-CN); and
[0257] The compound represented by formula 221,
[0258] However, the embodiments of the present disclosure are not limited thereto:
[0259]
[0260]
[0261] Formula 221
[0262]
[0263] In formula 221,
[0264] R 221 To R 223 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein R 221 To R 223 At least one selected from cyano, -F, -Cl, -Br, -I, C substituted with -F 1 -C 20 Alkyl, C substituted with -Cl 1 -C 20 Alkyl, C substituted with -Br 1 -C 20 Alkyl and C substituted with -I 1 -C 20 At least one substituent selected from the group consisting of:
[0265] Emission layer in the organic layer 150
[0266] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer can be patterned into a red emission layer, a green emission layer, or a blue emission layer according to the sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, wherein the two or more layers are in contact with each other or separated from each other. In one or more embodiments, the emission layer may include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light.
[0267] The emission layer may include a host and a dopant. The emission layer may include at least one selected from a phosphorescent dopant and a fluorescent dopant.
[0268] In the emission layer, the amount of the dopant may be in the range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.
[0269] The thickness of the emitter layer can be approximately To about In the range of, for example, about To about When the thickness of the emission layer is within this range, excellent light emitting characteristics can be obtained without significantly increasing the driving voltage.
[0270] Subject in the emission layer
[0271] In one or more embodiments, the host may include a compound represented by Formula 301:
[0272] Formula 301
[0273] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21
[0274] In formula 301,
[0275] Ar 301 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,
[0276] xb11 can be 1, 2 or 3,
[0277] L 301 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0278] xb1 can be an integer from 0 to 5.
[0279] R 301 It can be selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O) 2 (Q 301 ) and -P(=O)(Q 301 )(Q 302 ),
[0280] xb21 can be an integer from 1 to 5, and
[0281] Q 301 To Q 303 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 An alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the embodiments of the present disclosure are not limited thereto.
[0282] In one embodiment, in Formula 301, Ar 301 Can be selected from:
[0283] naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, peryl, phenanthrenyl, indenoanthryl, dibenzofuranyl, and dibenzothiophenyl; and
[0284] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one of naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, peryl, peryl, pentaphenyl, indenoanthryl, dibenzofuranyl and dibenzothiophenyl, and
[0285] Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 An alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the embodiments of the present disclosure are not limited thereto.
[0286] When xb11 in Formula 301 is two or more, two or more Ar 301 Connection can be made via a single button.
[0287] In one or more embodiments, the compound represented by Formula 301 may be represented by Formula 301-1 or Formula 301-2:
[0288] Formula 301-1
[0289]
[0290] Formula 301-2
[0291]
[0292] In Formula 301-1 and Formula 301-2,
[0293] A 301 To A 304can be independently selected from phenyl, naphthyl, phenanthrenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyridyl, pyrimidyl, indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, indolyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, furanyl, benzofuranyl, dibenzofuranyl, naphthofuranyl, benzonaphthofuranyl, dinaphthofuranyl, thienyl, benzothienyl, dibenzothienyl, naphthothienyl, benzonaphthothienyl and dinaphthothienyl,
[0294] X 301 Can be O, S or N-[(L 304 ) xb4 -R 304 ],
[0295] R 311 To R 314 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),
[0296] xb22 and xb23 can each independently be 0, 1 or 2,
[0297] L 301 、xb1、R 301 and Q 31 To Q 33 Same as described above,
[0298] L 302 To L 304 can be independently combined with L 301 The same definition,
[0299] xb2 to xb4 may each independently be the same as defined in conjunction with xb1, and
[0300] R 302 To R304 can be independently combined with R 301 The definition is the same.
[0301] For example, in Formula 301, Formula 301-1, and Formula 301-2, L 301 To L 304 Can be independently selected from:
[0302] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene, and azacarbazolylene; and
[0303] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridyl azine, pyrimidinyl, pyridazinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q 31)(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one of phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene, yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene and azacarbazolylene, and
[0304] Q 31 To Q 33 Same as described above.
[0305] In one embodiment, in Formula 301, Formula 301-1 and Formula 301-2, R 301 To R 304 Can be independently selected from:
[0306] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0307] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridyl azine, pyrimidinyl, pyridazinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl, and
[0308] Q 31 To Q 33 Same as described above.
[0309] In one embodiment, the host may include an alkaline earth metal complex. For example, the host may be selected from a Be complex (eg, compound H55), a Mg complex, and a Zn complex.
[0310] The host may include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), mCP (1,3-di-9-carbazolylbenzene), 1,3,5-tri(carbazol-9-yl)benzene (TCP), bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenylphosphine oxide (POPCPA), and compounds H1 to H55, but embodiments of the present disclosure are not limited thereto:
[0311]
[0312]
[0313]
[0314] In one embodiment, the host may include at least one selected from a silicon-containing compound (eg, BCPDS, etc.) and a phosphine oxide-containing compound (eg, POPCPA, etc.).
[0315] However, embodiments of the present disclosure are not limited thereto. In one embodiment, the host may include only one compound, or two or more different compounds (eg, BCPDS and POPCPA).
[0316] [Phosphorescent Dopant Included in Emission Layer in Organic Layer 150]
[0317] The phosphorescent dopant may include an organometallic complex represented by Formula 401:
[0318] Formula 401
[0319] M(L 401 ) xc1 (L 402 ) xc2
[0320] Formula 402
[0321]
[0322] In equations 401 and 402,
[0323] M may be selected from iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh) and thulium (Tm),
[0324] L 401 can be selected from the ligand represented by formula 402, xc1 can be 1, 2 or 3, wherein when xc1 is two or more, two or more L 401 can be the same or different from each other,
[0325] L 402 It can be an organic ligand, and xc2 can be an integer from 0 to 4, wherein when xc2 is two or more, two or more L 402 can be the same or different from each other,
[0326] X 401 To X 404 may each independently be nitrogen or carbon,
[0327] X 401 and X 403 Can be connected via single or double bonds, X 402 and X 404 Can be connected via single or double bonds,
[0328] A 401 and A 402 can be independently C 5 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0329] X 405 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q411 )-*'、*-C(Q 411 )(Q 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*'or*=C=*', where Q 411 and Q 412 It can be hydrogen, deuterium, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl or naphthyl,
[0330] X 406 Can be a single bond, O or S,
[0331] R 401 and R 402 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 20 Alkyl, substituted or unsubstituted C 1 -C 20 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q401 ) and -P(=O)(Q 401 )(Q 402 ), where Q 401 To Q 403 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, C 6 -C 20 Aryl and C 1 -C 20 Heteroaryl,
[0332] xc11 and xc12 may each independently be an integer from 0 to 10, and
[0333] The * and *' in formula 402 both refer to the binding site with M in formula 401.
[0334] In one embodiment, in equation 402, A 401 and A 402 They can all be independently selected from phenyl, naphthyl, fluorenyl, spirobifluorenyl, indenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiophenyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl and dibenzothiophenyl.
[0335] In one or more embodiments, in Formula 402, i) X 401 Can be nitrogen, X 402 It can be carbon, or ii) X 401 and X 402 Both may be nitrogen.
[0336] In one or more embodiments, in Formula 402, R 401 and R 402 Can be independently selected from:
[0337] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;
[0338] The C groups are substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, phenyl, naphthyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl and norbornenyl. 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;
[0339] Cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl;
[0340] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 at least one selected from the group consisting of an alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and
[0341] -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) and -P(=O)(Q 401 )(Q 402 ),and
[0342] Q 401 To Q 403 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10An alkoxy group, a phenyl group, a biphenyl group, and a naphthyl group, but the embodiments of the present disclosure are not limited thereto.
[0343] In one or more embodiments, when xc1 in equation 401 is two or greater, two or more L 401 Two A's 401 It can be optionally connected via X as a linker 407 To connect, or two or more L 401 Two A's 402 It can be optionally connected via X as a linker 408 to connect (see compounds PD1 to PD4 and PD7). 407 and X 408 can be independently a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 413 )-*'、*-C(Q 413 )(Q 414 )-*' or *-C(Q 413 )=C(Q 414 )-*'(where Q 413 and Q 414 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl or naphthyl), but the embodiments of the present disclosure are not limited thereto.
[0344] L in Formula 401 402 It can be a monovalent organic ligand, a divalent organic ligand or a trivalent organic ligand. 402 It may be selected from halogen, diketone (e.g., acetylacetone), carboxylic acid (e.g., picolinic acid), -C(=O)-, isonitrile, -CN, and phosphorus (e.g., phosphine or phosphite), but the embodiments of the present disclosure are not limited thereto.
[0345] In one or more embodiments, the phosphorescent dopant may be selected from, for example, compound PD1 to compound PD25, but the embodiments of the present disclosure are not limited thereto:
[0346]
[0347] Fluorescent dopant in the emission layer of the organic layer 150
[0348] The fluorescent dopant may include an arylamine compound or a styrylamine compound.
[0349] The fluorescent dopant may include a compound represented by Formula 501:
[0350] Formula 501
[0351]
[0352] In formula 501,
[0353] Ar 501 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,
[0354] L 501 To L 503 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0355] xd1 to xd3 may each independently be an integer from 0 to 3,
[0356] R 501 and R 502 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and
[0357] xd4 can be an integer from 1 to 6.
[0358] In one embodiment, Ar in Formula 501 501 Can be selected from:
[0359] naphthyl, heptathenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, phenanthrenyl, perylenyl, pentaphenanthrenyl, indenoanthryl, and indenophenanthrenyl; and
[0360] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 at least one of an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group, a naphthyl group, a heptathenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a benzo[9,10]phenanthrenyl group, a pyrenyl group, The following examples include 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33,
[0361] In one or more embodiments, L in Formula 501 501 To L 503 Can be independently selected from:
[0362] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, ...
[0363] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, a phenylene radical, a naphthylene radical, a fluorenyl radical, a spirobifluorenyl radical, a benzofluorenyl radical, a dibenzofluorenyl radical, a phenanthrenyl radical, an anthracene radical, a fluoranthenyl radical, a benzo[9,10]phenanthrenyl radical, a pyrenyl radical, a fluorenyl radical, a phenanthren ... The compounds include phenylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothiophenylene, and pyridylene.
[0364] In one or more embodiments, R in Formula 501 501 and R 502 Can be independently selected from:
[0365] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, and pyridyl; and
[0366] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl and -Si(Q 31 )(Q 32 )(Q 33 ) is at least one of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophene, and pyridyl, and
[0367] Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0368] In one or more embodiments, xd4 in equation 501 may be 2, but embodiments of the present disclosure are not limited thereto.
[0369] For example, the fluorescent dopant may be selected from Compound FD1 to Compound FD22:
[0370]
[0371]
[0372]
[0373] In one or more embodiments, the fluorescent dopant may be selected from the following compounds, but the embodiments of the present disclosure are not limited thereto.
[0374]
[0375]
[0376] Electron transport region in organic layer 150
[0377] The electron transport region may have: i) a single layer structure including a single layer including a single material; ii) a single layer structure including a single layer including a plurality of different materials; or iii) a multilayer structure having a plurality of layers including a plurality of different materials.
[0378] The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but the embodiments of the present disclosure are not limited thereto.
[0379] For example, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein for each structure, the constituent layers are sequentially stacked from the emission layer. However, the embodiment of the structure of the electron transport region is not limited thereto.
[0380] The electron transport region (eg, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one π electron-depleted nitrogen-containing ring.
[0381] As used herein, the term "π-electron-poor nitrogen-containing ring" refers to a C 1 -C 60 Heterocyclic group.
[0382] For example, the "π-electron-poor nitrogen-containing ring" may be i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' moiety, ii) a heteropolycyclic group in which two or more 5- to 7-membered heteromonocyclic groups each having at least one *-N=*' moiety are condensed with each other, or iii) a heteropolycyclic group in which at least one of the 5- to 7-membered heteromonocyclic groups each having at least one *-N=*' moiety is condensed with at least one C 5 -C 60 A carbocyclic condensed heteropolycyclic group.
[0383] Examples of π-electron-poor nitrogen-containing rings include, but are not limited to, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole, isobenzothiazole, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine and azacarbazole.
[0384] For example, the electron transport region may include a compound represented by Formula 601:
[0385] Formula 601
[0386] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0387] In formula 601,
[0388] Ar 601 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,
[0389] xe11 can be 1, 2 or 3,
[0390] L 601 Selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0391] xe1 can be an integer from 0 to 5,
[0392] R 601 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q601 )、-S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),
[0393] Q 601 To Q 603 can be independently C 1 -C 10 Alkyl, C 1 -C 10 alkoxy, phenyl, biphenyl, terphenyl or naphthyl, and
[0394] xe21 can be an integer from 1 to 5.
[0395] In one embodiment, xe11 number of Ar 601 and xe21 number of R 601 At least one of the may include a π-electron-poor nitrogen-containing ring.
[0396] In one embodiment, Ar in Formula 601 601 Can be selected from:
[0397] Phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, phenanthrenyl, phenanthrenyl, phenanthrenyl, phenanthryl, phenanthroline, phenazinyl, phenanthryl ...
[0398] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q32 ) is phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, naphthyl, phenanthrenyl, peryl, pentaphenanthrenyl, indenoanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl, and
[0399] Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0400] When xe11 in Formula 601 is two or greater, two or more Ar 601 Connection can be made via a single button.
[0401] In one or more embodiments, Ar in Formula 601 601 It may be anthracene.
[0402] In one or more embodiments, the compound represented by Formula 601 can be represented by Formula 601-1:
[0403] Formula 601-1
[0404]
[0405] In formula 601-1,
[0406] X 614 Can be N or C (R 614 ), X 615 Can be N or C (R 615 ), X 616 Can be N or C (R 616 ), from X 614 To X 616 At least one of the selected ones may be N,
[0407] L 611 To L 613 can be independently combined with L601 The same definition,
[0408] xe611 to xe613 can all independently be the same as defined in conjunction with xe1,
[0409] R 611 To R 613 can be independently combined with R 601 are defined identically, and
[0410] R 614 To R 616 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0411] In one embodiment, in equation 601 and equation 601-1, L 601 and L 611 To L 613 Can be independently selected from:
[0412] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene, and azacarbazolylene; and
[0413] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalide the phenylene radical of at least one of oxazinyl, naphthidinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthrylenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene , pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene and azacarbazolylene,
[0414] However, the embodiments of the present disclosure are not limited thereto.
[0415] In one or more embodiments, in Formula 601 and Formula 601-1, xe1 and xe611 to xe613 may each independently be 0, 1, or 2.
[0416] In one or more embodiments, in Formula 601 and Formula 601-1, R 601 and R 611 To R 613 Can be independently selected from:
[0417] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl , pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl;
[0418] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a benzo[9,10]phenanthrenyl group, a pyrenyl group, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0419] -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),and
[0420] Q 601 and Q 602 Same as described above.
[0421] The electron transport region may include at least one compound selected from compound ET1 to compound ET36, but the embodiments of the present disclosure are not limited thereto:
[0422]
[0423]
[0424]
[0425]
[0426] In one embodiment, the electron transport region may include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq 3 At least one compound selected from the group consisting of 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), NTAZ, diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1) and 3P-T2T:
[0427]
[0428] The thickness of the buffer layer, hole blocking layer or electron control layer can be about To about In the range of, for example, about To about When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within these ranges, the hole blocking layer or the electron control layer may have excellent hole blocking characteristics or electron control characteristics without significantly increasing the driving voltage.
[0429] The thickness of the electron transport layer can be about To about In the range of, for example, about To about When the thickness of the electron transport layer is within the range described above, the electron transport layer may have appropriate or satisfactory electron transport characteristics without significantly increasing the driving voltage.
[0430] The electron transport region (eg, an electron transport layer in the electron transport region) may further include a material including a metal in addition to the materials described above.
[0431] The material containing metal may include at least one selected from alkali metal complexes and alkaline earth metal complexes. The alkali metal complex may include metal ions selected from Li ions, Na ions, K ions, Rb ions and Cs ions, and the alkaline earth metal complex may include metal ions selected from Be ions, Mg ions, Ca ions, Sr ions and Ba ions. The ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.
[0432] For example, the material including the metal may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium quinolate, LiQ) or compound ET-D2.
[0433]
[0434] The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 190. The electron injection layer may directly contact the second electrode 190.
[0435] The electron injection layer may have: i) a single layer structure including a single layer including a single material; ii) a single layer structure including a single layer including a plurality of different materials; or iii) a multilayer structure having a plurality of layers including a plurality of different materials.
[0436] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0437] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but the embodiments of the present disclosure are not limited thereto.
[0438] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.
[0439] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.
[0440] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may be selected from oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of alkali metals, alkaline earth metals, and rare earth metals.
[0441] The alkali metal compound may be selected from alkali metal oxides (such as Li 2 O, Cs 2 O, or K 2 O) and alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI). In one embodiment, the alkali metal compound may be selected from LiF, Li 2 O, NaF, LiI, NaI, CsI, and KI, but the embodiments of the present disclosure are not limited thereto.
[0442] The alkaline earth metal compound may be selected from alkaline earth metal oxides such as BaO, SrO, CaO, Ba x Sr 1-x O (0 < x < 1), Ba x Ca 1-x O (0 < x < 1). In one embodiment, the alkaline earth metal compound may be selected from BaO, SrO, and CaO, but the embodiments of the present disclosure are not limited thereto.
[0443] The rare earth metal compound may be selected from YbF 3 、ScF 3 、Sc 2 O 3 、Y 2 O 3 、Ce 2 O 3 、GdF 3 和TbF 3 。在一个实施例中,稀土金属化合物可以选自于YbF3 ScF 3 , TbF 3 ,YbI 3 ScI 3 and TbI 3 , but the embodiments of the present disclosure are not limited thereto.
[0444] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may include ions of the alkali metal, alkaline earth metal and rare earth metal as described above, and the ligand coordinated to the metal ion of the alkali metal complex, alkaline earth metal complex or rare earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.
[0445] The electron injection layer can be composed of alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or any combination thereof as described above. In one or more embodiments, the electron injection layer can also include organic material. When the electron injection layer also includes organic material, alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or any combination thereof can be uniformly or non-uniformly dispersed in the matrix including the organic material.
[0446] The thickness of the electron injection layer can be about To about In the range of, for example, about To about When the thickness of the electron injection layer is within the range described above, the electron injection layer may have appropriate or satisfactory electron injection characteristics without significantly increasing the driving voltage.
[0447] The second electrode 190
[0448] The second electrode 190 may be located on the organic layer 150 having such a structure. The second electrode 190 may be a cathode as an electron injection electrode, and in this regard, a material for forming the second electrode 190 may be selected from metals, alloys, conductive compounds, and combinations thereof having a relatively low work function.
[0449] The second electrode 190 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, and IZO, but the embodiments of the present disclosure are not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0450] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.
[0451] Figures 2 to 4 Description
[0452] Figure 2 The organic light emitting device 20 includes a first cladding layer 210, a first electrode 110, an organic layer 150, and a second electrode 190 which are sequentially stacked in the order stated, Figure 3 The organic light emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 sequentially stacked in the order of this statement, Figure 4 The organic light emitting device 40 includes a first cladding layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second cladding layer 220 which are sequentially stacked in the stated order.
[0453] for Figures 2 to 4 , can be combined by reference Figure 1 The description is given to understand the first electrode 110 , the organic layer 150 , and the second electrode 190 .
[0454] In the organic layer 150 of each of the organic light-emitting devices 20 and 40, light generated in the emission layer can pass through the first electrode 110 as a semi-transmissive electrode or a transmissive electrode and the first covering layer 210 toward the outside, and in the organic layer 150 of each of the organic light-emitting devices 30 and 40, light generated in the emission layer can pass through the second electrode 190 as a semi-transmissive electrode or a transmissive electrode and the second covering layer 220 toward the outside.
[0455] According to the principle of constructive interference, the first cladding layer 210 and the second cladding layer 220 can improve external light emitting efficiency.
[0456] The first capping layer 210 and the second capping layer 220 may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material.
[0457] At least one selected from the first coating 210 and the second coating 220 may each independently include at least one material selected from carbocyclic compounds, heterocyclic compounds, amine compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds, and amine compounds may be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one selected from the first coating 210 and the second coating 220 may each independently include an amine compound.
[0458] In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include the compound represented by Formula 201 or the compound represented by Formula 202.
[0459] In one or more embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include a compound selected from Compounds HT28 to HT33 and Compounds CP1 to CP5, but the embodiments of the present disclosure are not limited thereto.
[0460]
[0461] In the above, it has been combined Figures 1 to 4 The organic light emitting device according to the embodiment is described. However, the embodiments of the present disclosure are not limited thereto.
[0462] A layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region can be formed in a specific region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser induced thermal imaging.
[0463] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition temperature may be about 100° C. to about 500° C., about 10 -8 Up to about 10 -3 Torr vacuum and approx. To about The vacuum deposition was performed at a deposition rate of .
[0464] When a layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region are formed by spin coating, spin coating can be performed at a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature of about 80°C to about 200°C by taking into account the materials to be included in the layer to be formed and the structure of the layer to be formed.
[0465] Display device
[0466] The organic light emitting device may be included in a display device including a thin film transistor. The thin film transistor may include a source electrode, a drain electrode, and an active layer, and one of the source electrode and the drain electrode may electrically contact a first electrode of the organic light emitting device.
[0467] The thin film transistor may further include a gate electrode, a gate insulating layer, and the like.
[0468] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, etc., but the embodiments of the present disclosure are not limited thereto.
[0469] The display device may further include a sealing member that seals the organic light-emitting device. The sealing member may enable an image from the organic light-emitting device to be realized, and may prevent or reduce external air and moisture from penetrating into the organic light-emitting device. The sealing member may be a sealing substrate made of glass or plastic. The sealing member may be a thin film encapsulation layer including a plurality of organic layers and / or a plurality of inorganic layers. When the sealing member is a thin film encapsulation layer, the entire flat display device may be made flexible.
[0470] General definitions of at least some of the substituents
[0471] As used herein, the term “C 1 -C 60 "Alkyl" refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, examples of which include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl. As used herein, the term "C 1 -C 60 "Alkylene" refers to a group having a C 1 -C 60 The structure of the alkyl group is basically the same as the divalent group of the structure.
[0472] As used herein, the term “C 2 -C 60 "Alkenyl" refers to 2 -C 60 An alkyl group is a hydrocarbon group having at least one carbon-carbon double bond at the main chain (e.g., in the middle) or at the terminal (e.g., at the end), examples of which include ethenyl, propenyl, and butenyl. As used herein, the term “C 2 -C60 "Alkenylene" refers to a 2 -C 60 The structure of the alkenyl group is a divalent group of substantially the same structure.
[0473] As used herein, the term “C 2 -C 60 "Alkynyl" refers to a C 2 -C 60 An alkyl group is a hydrocarbon group having at least one carbon-carbon triple bond at the main chain (e.g., in the middle) or at the terminal (e.g., at the end), examples of which include ethynyl and propynyl. As used herein, the term “C 2 -C 60 "Alkyne" refers to a 2 -C 60 The structure of the alkynyl group is a divalent group of substantially the same structure.
[0474] As used herein, the term “C 1 -C 60 "Alkoxy" refers to -OA 101 (Among them, A 101 C 1 -C 60 An alkyl group is a monovalent group represented by an alkyl group, examples of which include a methoxy group, an ethoxy group and an isopropoxy group.
[0475] As used herein, the term “C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, examples of which include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. As used herein, the term "C 3 -C 10 "Cycloalkylene" refers to a cycloalkylene group having a 3 -C 10 The structure of the cycloalkyl group is substantially the same as that of a divalent group.
[0476] As used herein, the term “C 1 -C 10 "Heterocycloalkyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as ring atoms and 1 to 10 carbon atoms, examples of which include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and tetrahydrothienyl. As used herein, the term "C 1 -C 10 "Heterocycloalkylene" refers to a group having a C 1 -C 10 The structure of the heterocycloalkyl group is substantially the same as that of a divalent group.
[0477] As used herein, the term “C 3 -C10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and not having aromaticity (e.g., the entire ring and / or the entire group is not aromatic), examples of which include cyclopentenyl, cyclohexenyl and cycloheptenyl. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to a 3 -C 10 The structure of the cycloalkenyl group is a divalent group of substantially the same structure.
[0478] As used herein, the term “C 1 -C 10 The term "heterocycloalkenyl group" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as ring atoms, 1 to 10 carbon atoms and at least one double bond in its ring. 1 -C 10 Non-limiting examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. As used herein, the term “C 1 -C 10 "Heterocycloalkenylene" refers to a 1 -C 10 The structure of the heterocycloalkenyl group is a divalent group of substantially the same structure.
[0479] As used herein, the term “C 6 -C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms. 6 -C 60 The arylene group refers to a divalent group having a carbocyclic aromatic system including 6 to 60 carbon atoms. 6 -C 60 Examples of aryl groups are phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl and When C 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the rings may be fused to each other (eg, combined together).
[0480] As used herein, the term “C 1 -C 60 "Heteroaryl" refers to a monovalent group having a carbocyclic aromatic system having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom in addition to 1 to 60 carbon atoms. As used herein, the term "C 1 -C 60The term "heteroarylene" refers to a divalent group having a carbocyclic aromatic system having at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom in addition to 1 to 60 carbon atoms. 1 -C 60 Examples of heteroaryl groups are pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl and isoquinolyl. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene group includes two or more rings, the rings may be fused to each other (eg, combined together).
[0481] As used herein, the term “C 6 -C 60 "Aryloxy" means -OA 102 (Among them, A 102 C 6 -C 60 Aryl), C 6 -C 60 Arylthio represents -SA 103 (Among them, A 103 C 6 -C 60 aryl).
[0482] As used herein, the term “C 1 -C 60 "Heteroaryloxy" means -OA 104 (Among them, A 104 C 1 -C 60 Heteroaryl), as used herein, the term "C 1 -C 60 "Heteroarylthio" means -SA 105 (Among them, A 105 C 1 -C 60 heteroaryl).
[0483] As used herein, the term "monovalent non-aromatic condensed polycyclic group" refers to a monovalent group having two or more rings condensed to each other (e.g., combined together), only carbon atoms (e.g., having 8 to 60 carbon atoms) as ring atoms, and not having aromaticity in its entire molecular structure (e.g., the entire group and / or the entire molecule does not have aromaticity). An example of a monovalent non-aromatic condensed polycyclic group is a fluorenyl group. As used herein, the term "divalent non-aromatic condensed polycyclic group" refers to a divalent group having a structure substantially the same as that of a monovalent non-aromatic condensed polycyclic group.
[0484] As used herein, the term "monovalent non-aromatic condensed heteropolycyclic group" refers to a monovalent group having two or more rings condensed with each other (e.g., combined together), having at least one heteroatom selected from N, O, Si, P and S other than carbon atoms (e.g., having 1 to 60 carbon atoms) as ring-forming atoms, and not having aromaticity in its entire molecular structure (e.g., the entire group and / or the entire molecule does not have aromaticity). An example of a monovalent non-aromatic condensed heteropolycyclic group is a carbazolyl group. As used herein, the term "divalent non-aromatic condensed heteropolycyclic group" refers to a divalent group having a structure substantially the same as that of a monovalent non-aromatic condensed heteropolycyclic group.
[0485] As used herein, the term “C 5 -C 60 "Carbocyclic group" refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms, wherein the ring atoms are only carbon atoms. 5 -C 60 The carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. 5 -C 60 The carbocyclic group can be a ring (such as benzene), a monovalent group (such as phenyl) or a divalent group (such as phenylene). In one or more embodiments, the carbonyl group is connected to the carbonyl group. 5 -C 60 The number of substituents of the carbocyclic group, C 5 -C 60 The carbocyclic group may be a trivalent group or a tetravalent group.
[0486] As used herein, the term “C 1 -C 60 "Heterocyclic group" refers to a 5 -C 60 The structure of the carbocyclic group is substantially the same as that of the group except that as a ring-constituting atom, in addition to carbon (the number of carbon atoms may be in the range of 1 to 60), at least one hetero atom selected from N, O, Si, P and S is used.
[0487] In the specification, the substituted C 5 -C 60 Carbocyclic, substituted C 1 -C 60 Heterocyclic, substituted C 3 -C 10 Cycloalkylene, substituted C 1 -C 10 Heterocycloalkylene, substituted C 3 -C 10 Cycloalkenylene, substituted C 1 -C 10 Heterocycloalkenylene, substituted C 6 -C 60Arylene, substituted C 1 -C 60 Heteroarylene, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
[0488] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;
[0489] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) of at least one of C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;
[0490] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups;
[0491] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 ) of at least one of C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and
[0492] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),and
[0493] Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, C substituted with at least one selected from deuterium, -F and cyano group 1 -C 60alkyl, C substituted with at least one selected from deuterium, -F and cyano 6 -C 60 Aryl, biphenyl and terphenyl.
[0494] As used herein, the term "Ph" means phenyl, as used herein, the term "Me" means methyl, as used herein, the term "Et" means ethyl, as used herein, the term "ter-Bu" or "Bu" means phenyl. t " represents a tert-butyl group, and as used herein, the term "OMe" represents a methoxy group.
[0495] As used herein, the term "biphenyl" refers to "phenyl substituted with phenyl". In other words, "biphenyl" is a phenyl having C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.
[0496] As used herein, the term "terphenyl" refers to a "phenyl group substituted with a biphenyl group." In other words, a "terphenyl group" is a phenyl group substituted with a C 6 -C 60 Aryl C 6 -C 60 Phenyl with aryl as substituent.
[0497] Unless otherwise defined, * and *' as used herein refer to the binding sites to adjacent atoms in the corresponding formula.
[0498] Hereinafter, the compound according to the embodiment and the organic light emitting device according to the embodiment will be described in more detail with reference to Synthesis Examples and Examples. The expression "using B instead of A" used in describing Synthesis Examples means using B instead of A in the same molar equivalent.
[0499] Example
[0500] Synthesis Example 1: Synthesis of Compound 1
[0501]
[0502] 3 g (0.0067 mol) of 7,7,11,11-tetramethyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7,11-dihydrobenzo[8,1]indolizino[2,3,4,5,6-defg]acridine and 0.96 g (0.0034 mol) of 1,5-dibromonaphthalene were added to a three-necked flask (100 ml), oxygen was removed therefrom, and 3 ml of 2N K 2 CO 3 and a mixed solution of toluene / EtOH, and the resultant was purged with nitrogen. Then, 0.1 g of catalyst Pd (pph) was added thereto. 3 )4 The obtained product was stirred at 100°C for 24 hours under reflux. Water was added thereto to terminate the reaction, and three extractions were performed thereon using dichloromethane, and the solvent was removed therefrom. The obtained product was subjected to column chromatography using a solvent of ethyl acetate: normal hexane (1:10) to obtain 2.2 g (84%) of compound 1.
[0503] H-NMR (CDCl 3 ):8.90(2H,d),8.45(2H,d),8.37(2H,d),8.12(2H,d),7.88(4H,s),7.70( 2H,t),7.45(2H,d),7.20(2H,t),7.08(2H,t),6.99(2H,d),1.70(24H,t).
[0504] Synthesis Example 2: Synthesis of Compound 2
[0505]
[0506] 3 g (0.0067 mol) of 7,7,11,11-tetramethyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7,11-dihydrobenzo[8,1]indolizino[2,3,4,5,6-defg]acridine and 0.96 g (0.0034 mol) of 2,6-dibromonaphthalene were added to a three-necked flask (100 ml), oxygen was removed therefrom, and 3 ml of 2N K 2 CO 3 and a mixed solution of toluene / EtOH, and the resultant was purged with nitrogen. Then, 0.1 g of catalyst Pd (pph) was added thereto. 3 ) 4 The obtained product was stirred at 100°C for 24 hours under reflux. Water was added thereto to terminate the reaction, and three extractions were performed thereon using dichloromethane, and the solvent was removed therefrom. The obtained product was subjected to column chromatography using a solvent of ethyl acetate: normal hexane (1:10) to obtain 2.2 g (84%) of compound 2.
[0507] H-NMR (CDCl 3 ):8.90(2H,d),8.45(2H,d),8.37(2H,d),8.12(2H,d),7.88(4H,s),7.70( 2H,t),7.45(2H,d),7.20(2H,t),7.08(2H,t),6.99(2H,d),1.70(24H,t).
[0508] Synthesis Example 3: Synthesis of Compound 3
[0509]
[0510] 3 g (0.0067 mol) of 7,7,11,11-tetramethyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7,11-dihydrobenzo[8,1]indolizino[2,3,4,5,6-defg]acridine and 2.67 g (0.0067 mol) of 9-bromo-7,7,11,11-tetramethyl-7,11-dihydrobenzo[8,1]indolizino[2,3,4,5,6-defg]acridine were added to a three-necked flask (100 ml), oxygen was removed therefrom, and 3 ml of 2N K 2 CO 3 and a mixed solution of toluene / EtOH, and the resultant was purged with nitrogen. Then, 0.1 g of catalyst Pd (pph) was added thereto. 3 ) 4 The obtained product was stirred at 100°C for 24 hours under reflux. Water was added thereto to terminate the reaction, and three extractions were performed thereon using dichloromethane, and the solvent was removed therefrom. The obtained product was subjected to column chromatography using a solvent of ethyl acetate: normal hexane (1:10) to obtain 3.89 g (90%) of compound 3.
[0511] H-NMR (CDCl 3 ):8.45(2H,d),8.09(2H,d),7.88(4H,s),7.45(2H,d),7.20(2H,t),7.08(2H,t),6.99(2H,d),1.70(24H,t).
[0512] Synthesis Example 4: Synthesis of Compound 4
[0513]
[0514] 3 g (0.0067 mol) of 7,7,11,11-tetramethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7,11-dihydrobenzo[8,1]indolizino[2,3,4,5,6-defg]acridine and 2.67 g (0.0067 mol) of 8-bromo-7,7,11,11-tetramethyl-7,11-dihydrobenzo[8,1]indolizino[2,3,4,5,6-defg]acridine were added to a three-necked flask (100 ml), oxygen was removed therefrom, and 3 ml of 2N K 2 CO 3 and a mixed solution of toluene / EtOH, and the resultant was purged with nitrogen. Then, 0.1 g of catalyst Pd (pph) was added thereto. 3 )4 The obtained product was stirred at 100°C for 24 hours under reflux. Water was added thereto to terminate the reaction, and three extractions were performed thereon using dichloromethane, and the solvent was removed therefrom. The obtained product was subjected to column chromatography using a solvent of ethyl acetate: normal hexane (1:10) to obtain 3.80 g (88%) of compound 4.
[0515] H-NMR (CDCl 3 ):8.45(2H,d),8.09(2H,d),7.71(2H,d),7.45-7.41(4H,m),7.24(2H,t),7.07(2H,t),6.98(2H,d),1.69(24H,t).
[0516] Synthesis Example 5: Synthesis of Compound 5
[0517]
[0518] 3 g (0.0067 mol) of 7,7,11,11-tetramethyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7,11-dihydrobenzo[8,1]indolizino[2,3,4,5,6-defg]acridine and 0.80 g (0.0034 mol) of 1,4-dibromobenzene were added to a three-necked flask (100 ml), oxygen was removed therefrom, and 3 ml of 2N K 2 CO 3 and a mixed solution of toluene / EtOH, and the resultant was purged with nitrogen. Then, 0.1 g of catalyst Pd (pph) was added thereto. 3 ) 4 The mixture was stirred at 100°C for 24 hours under reflux. Water was added thereto to terminate the reaction, and three extractions were performed thereon using dichloromethane, and the solvent was removed therefrom. The obtained mixture was subjected to column chromatography using a solvent of ethyl acetate: normal hexane (1:10) to obtain 1.96 g (80%) of compound 5.
[0519] H-NMR (CDCl 3 ):8.45(2H,d),8.09(2H,d),7.84(4H,s),7.45(2H,d),7.25(6H,m),7.08(2H,t),6.99(2H,d),1.70(24H,t).
[0520] Synthesis Example 6: Synthesis of Compound 6
[0521]
[0522] 3 g (0.0067 mol) of 7,7,11,11-tetramethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7,11-dihydrobenzo[8,1]indolizino[2,3,4,5,6-defg]acridine and 0.80 g (0.0034 mol) of 1,4-dibromobenzene were added to a three-necked flask (100 ml), oxygen was removed therefrom, and 3 ml of 2N K 2 CO 3 and a mixed solution of toluene / EtOH, and the resultant was purged with nitrogen. Then, 0.1 g of catalyst Pd (pph) was added thereto. 3 ) 4 The obtained product was stirred at 100°C for 24 hours under reflux. Water was added thereto to terminate the reaction, and three extractions were performed thereon using dichloromethane, and the solvent was removed therefrom. The obtained product was subjected to column chromatography using a solvent of ethyl acetate: normal hexane (1:10) to obtain 1.89 g (77%) of compound 6.
[0523] H-NMR (CDCl 3 ):8.45(2H,d),8.09(2H,d),7.71(2H,d),7.45-7.41(4H,m),7.25-7.23(6H,m),7.07(2H,t),6.98(2H,d),1.69(24H,t).
[0524] Evaluation Example 1
[0525] The HOMO energy level, LUMO energy level, singlet state (S) of TCTA, Compound 1, Compound 2, Compound 3, Compound 4, Compound 5, Compound 6, Compound A and Compound B were evaluated according to the method shown in Table 1. 1 ) energy level and triplet state (T 1 ) energy levels, and the results are shown in Table 2.
[0526] Table 1
[0527]
[0528] Table 2
[0529]
[0530]
[0531]
[0532]
[0533] Evaluation Example 2
[0534] In order to calculate the BDE caused by excitons in the anionic state, the structure of each compound was optimized using density functional theory using B3LYP hybrid functional and 6-311G** basis set. After optimizing the structure of each compound, the most stable structure in the anionic state was selected, and the energy required to decompose the structure of the compound was calculated. The BDE of TCTA, compound 1 to compound 6, compound A and compound B in the anionic state was evaluated, and the results are shown in Table 3.
[0535] Table 3
[0536] BDE(eV) 1 3.9 2 4.07 3 4.10 4 3.88 5 4.22 6 4.13 A 4.0 B 3.89 TCTA 1.4
[0537] From Table 3, it can be seen that compounds 1 to 6 have relatively very high BDEs. For example, it can be seen that compounds 1 to 6 have BDEs that are much higher than the BDE of TCTA.
[0538] Evaluation Example 3
[0539] As the anode, HAT-CN was layered on ITO up to The compound of Table 4 is deposited to a thickness of The thickness of HAT-CN is stacked to Ag is deposited to a thickness of The thickness of AgMg is deposited to The thickness of the single hole device (HOD) was obtained. The position of the slope of 2 was found by plotting the y-axis logarithmically, the SCLC region was confirmed, and the mobility was extracted by equation 1 (Mott-Gurney theory equation). The results are shown in Table 4.
[0540] Equation 1
[0541]
[0542] In equation 1,
[0543] V is the applied voltage, and
[0544] L is the thickness.
[0545] Table 4
[0546] <![CDATA[Hole mobility (cm 2 / Vs)]]> 1 <![CDATA[1.5e -4 ]]> 2 <![CDATA[9.1e -5 ]]> 3 <![CDATA[4.3e -4 ]]> 4 <![CDATA[1.2e -4 ]]> 5 <![CDATA[8.5e -4 ]]> 6 <![CDATA[7.3e -4 ]]> A <![CDATA[1.2e -5 <!-- 61 -->]]> B <![CDATA[2.3e -5 ]]> TCTA <![CDATA[3.5e -4 ]]>
[0547] From Table 4, it was confirmed that Compounds 1 to 6 had significantly improved hole mobility compared to Compound A and Compound B.
[0548] Example 1
[0549] As an anode, an ITO substrate on which ITO / Ag / ITO was deposited was cut into a size of 50 mm×50 mm×0.7 mm, ultrasonicated for 5 minutes each using isopropyl alcohol and pure water, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the ITO substrate was provided to a vacuum deposition device.
[0550] The compound HAT-CN was vacuum deposited on the ITO substrate to form a hole injection layer with a thickness of 5 nm, the compound NPB was vacuum deposited on the hole injection layer to form a hole transport layer with a thickness of 60 nm, the compound 1 was vacuum deposited on the hole transport layer to form an electron blocking layer with a thickness of 5 nm, and the compound ADN and the compound BCzVBi were co-deposited on the electron blocking layer at a weight ratio of 97:3 to form an emission layer with a thickness of 20 nm. The compound 3P-T2T was deposited on the emission layer to form an electron transport layer with a thickness of 30 nm. LiQ was deposited on the electron transport layer to form an electron injection layer with a thickness of 1 nm, and AgMg (weight ratio of 10:1) was co-deposited on the electron injection layer to form a cathode with a thickness of 10 nm, thereby completing the manufacture of the organic light-emitting device.
[0551] Examples 2 to 6 and Comparative Examples 1 to 3
[0552] An organic light emitting device was manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 5 were respectively used in forming the electron blocking layer.
[0553] Evaluation example
[0554] By using Keithley SMU 236 and luminance meter PR650 at 50mA / cm 2 The driving voltage, current efficiency, brightness, and lifetime of the organic light emitting devices manufactured according to Examples 1 to 6 and Comparative Examples 1 to 3 were measured at a current density of , and the results are shown in Table 5. The lifetime represents the amount of time when the brightness is 97% of the initial brightness (100%).
[0555] Table 5
[0556]
[0557]
[0558] Referring to Table 1, it is confirmed that the brightness life of the organic light-emitting devices of Examples 1 to 6 is very excellent compared to the brightness life of the organic light-emitting devices of Comparative Examples 1 to 3. Although not limited to a specific mechanism or theory, Compound A and Compound B have BDEs similar to those of Compounds 1 to 6, but because the hole mobility is very low, hole injection from the electron blocking layer to the emission layer is not smoothly performed. Therefore, although Compound A and Compound B have high BDE, the host compound in the organic light-emitting devices of Comparative Examples 1 and 2 is degraded due to the high electron density in the emission layer, thereby reducing its life. In addition, because TCTA has a significantly low BDE compared to Compounds 1 to 6, it is confirmed that the brightness life of the organic light-emitting device is very short.
[0559] The organic light emitting device according to an embodiment of the present disclosure may have low driving voltage, high brightness, high efficiency, and a long lifespan.
[0560] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments.
[0561] It will be understood that, although the terms "first", "second", "third", etc. may be used herein to describe various elements, components, regions, layers and / or parts, these elements, components, regions, layers and / or parts should not be limited by these terms. These terms are used to distinguish one element, component, region, layer or part from another element, component, region, layer or part. Therefore, without departing from the spirit and scope of the present disclosure, the first element, component, region, layer or part described above may be named as the second element, component, region, layer or part.
[0562] For ease of explanation, spatially relative terms such as "under", "below", "below", "under", "above", "on", etc. may be used herein to describe the relationship of one element or feature to another element or feature as shown in the figure. It will be understood that, in addition to the orientations depicted in the drawings, the spatially relative terms are intended to include different orientations of the device in use or operation. For example, if the device in the drawings is turned over, the elements described as "below" or "below" or "below" other elements or features will then be positioned as "above" the other elements or features. Therefore, the example terms "below" and "under" can include both above and below orientations. The device can be positioned otherwise (e.g., rotated 90 degrees or in other orientations), and the spatially relative descriptors used herein should be interpreted accordingly.
[0563] As used herein, the terms "substantially", "approximately" and similar terms are used as approximate terms, rather than as terms of degree, and are intended to explain the inherent deviations in measurements or calculations that will be recognized by those of ordinary skill in the art. In addition, when describing embodiments of the present disclosure, the use of "may" refers to "one or more embodiments of the present disclosure." As used herein, the term "using" and variations thereof may be considered to be synonymous with the term "utilizing" and variations thereof, respectively. In addition, the term "exemplary" is intended to represent an example or illustration.
[0564] In addition, any numerical range stated herein is intended to include all sub-ranges of the same numerical precision included in the stated range. For example, the range of "1.0 to 10.0" is intended to include all sub-ranges between the stated minimum value 1.0 and the stated maximum value 10.0 (and including the minimum value 1.0 and the maximum value 10.0), that is, with a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical value limit stated herein is intended to include all lower numerical limits included therein, and any minimum numerical value limit stated in this specification is intended to include all higher numerical limits included therein. Therefore, the applicant reserves the right to modify this specification (including claims) to explicitly state any sub-range included in the scope explicitly stated herein.
[0565] Although one or more embodiments have been described with reference to the drawings, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the claims and their equivalents.
Claims
1. A condensed ring compound, wherein the condensed ring compound is represented by formula 1-2: Formula 1-2 in, In formula 1-2, L 11 Selected from the groups represented by Formula 4-1 to Formula 4-12: Among them, in Formula 4-1 to Formula 4-12, R 41 Selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl and peryl, b41 is selected from 1, 2, 3 and 4, b42 is selected from 1, 2, 3, 4, 5 and 6, * and *' refer to the binding sites with adjacent atoms. a11 is selected from 0, 1 and 2, X 11a and X 11b are independently selected from C(R 14 )(R 15 ) and Si(R 14 )(R 15 ), X 12a and X 12b are independently selected from C(R 16 )(R 17 ) and Si(R 16 )(R 17 ), R 11a , R 11b , R 12a , R 12b , R 13a , R 13b , R 14 To R 17 are independently selected from: Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl and C1-C 20 Alkoxy; C1-C1-C2-substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl and terphenyl 20 Alkyl and C1-C 20 Alkoxy; Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, and pentacene; and are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, at least one of cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl and pentacene, b11a and b11b are independently selected from 1 and 2, b12a, b12b, b13a and b13b are each independently an integer of 1 to 3.
2. The condensed ring compound according to claim 1, wherein: R 11a , R 11b , R 12a , R 12b , R 13a , R 13b , R 14 To R 17 are independently selected from: Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, and C1-C 20 alkyl; C1-C ... 20 Alkyl; and The groups represented by Formula 5-1 to Formula 5-9: Among them, in Formula 5-1 to Formula 5-9, R 51 and R 52 are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl and peryl, b51 is selected from 1, 2, 3, 4 and 5, b52 is selected from 1, 2, 3, 4, 5, 6 and 7, b53 is selected from 1, 2, 3, 4, 5, 6, 7, 8 and 9, b54 is selected from 1, 2, 3 and 4, and *Indicates the binding site with the adjacent atom.
3. The condensed ring compound according to claim 1, wherein: The condensed ring compound is represented by Formula 1-12: Formula 1-12 Among them, in formula 1-12, L 11 Combined with L in formula 1-2 11 The same definition, a11 is the same as that defined in formula 1-2. R 11a , R 11b , R 12a , R 12b , R 13a , R 13b , R 14a , R 14b , R 15a , R 15b , R 16a , R 16b , R 17a and R 17b are independently combined with R in formula 1-2 11a The same definition, b11a and b11b are independently the same as defined in b11a in formula 1-2, and b12a, b12b, b13a and b13b are independently defined in the same manner as b12a in Formula 1-2.
4. The condensed ring compound according to claim 1, wherein: The condensed ring compound is selected from compound 4 and compound 6:
5. The condensed ring compound according to claim 1, wherein: The bond dissociation energy of the condensed ring compound is equal to or greater than 1.8 eV.
6. An organic light-emitting device, comprising: a first electrode; a second electrode; as well as an organic layer, located between the first electrode and the second electrode, and including an emission layer, Wherein, the organic layer comprises the condensed ring compound according to claim 1.
7. The organic light emitting device according to claim 6, wherein: The emission layer includes the condensed-ring compound.
8. The organic light emitting device according to claim 6, wherein: The first electrode is an anode, The second electrode is a cathode, The organic layer further comprises a hole transport region between the first electrode and the emission layer and / or an electron transport region between the emission layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer or any combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer or any combination thereof.
9. The organic light emitting device according to claim 8, wherein: The electron blocking layer includes the condensed ring compound.
10. The organic light emitting device according to claim 9, wherein: The emission layer includes a main body and satisfies condition 1: Condition 1 BDE(C - )>T1(H), Among them, in condition 1, BDE(C - ) is the bond dissociation energy of the condensed ring compound in the anionic state, and T1(H) is the lowest excited triplet energy level of the host.
11. The organic light emitting device according to claim 9, wherein: The emission layer includes a main body and satisfies condition 2: Condition 2 |HOMO(H)-HOMO(C)|≤0.3eV, Among them, in condition 2, HOMO(H) is the highest occupied molecular orbital energy level of the host, and HOMO (C) is the highest occupied molecular orbital energy level of the condensed ring compound.
12. A display device, comprising: A thin film transistor, comprising a source electrode, a drain electrode and an active layer; as well as The organic light-emitting device according to claim 6, The first electrode of the organic light emitting device is electrically coupled to one selected from the source electrode and the drain electrode of the thin film transistor.
Citation Information
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