Composition, organic layer prepared from the composition, and organic light-emitting device
A composition of high molecular weight and non-arylamine low molecular weight compounds enhances solvent resistance, enabling low-cost, high-resolution pixel production in organic light-emitting devices through solution coating processes.
Patent Information
- Application Number
- CN201910954166.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2018-12-26
- Filing Date
- 2019-10-09
- Publication Date
- 2024-12-13
- Estimated Expiration
- 2039-10-09
AI Technical Summary
Existing organic light-emitting devices face challenges in manufacturing high-resolution pixels due to the use of vacuum deposition processes, which are costly, and solution coating processes face issues with the solubility of materials used in forming the hole transport layer.
A composition comprising a high molecular weight compound and a non-arylamine low molecular weight compound, along with a solvent, is used to form an organic layer with enhanced dissolution resistance, allowing for low-cost manufacturing through solution coating processes.
The composition enables the formation of an organic layer with improved solvent resistance and stability, facilitating the production of high-resolution pixels in organic light-emitting devices.
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Figure CN111370595B_ABST
Abstract
Description
[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2018-0169902 filed on December 26, 2018, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field
[0002] One or more aspects of example embodiments of the present disclosure relate to a composition, an organic layer prepared from the composition, and a device including the organic layer. Background Art
[0003] Compared to devices in the related art, organic light emitting devices are self-emissive devices that may have wide viewing angles, high contrast, short response times, and / or excellent characteristics in terms of brightness, driving voltage, and response speed.
[0004] An example 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 stacked 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) may recombine in the emission layer to generate excitons. These excitons may transition from an excited state to a ground state, thereby generating light.
[0005] When an organic light emitting device is manufactured by a vacuum deposition process, the manufacturing cost increases due to the use of a vacuum system. When a shadow mask is used to manufacture pixels for a full-color display, it may be difficult to manufacture high-resolution pixels.
[0006] In contrast, when a solution coating process such as inkjet printing, nozzle printing, screen printing, and / or spin coating is used, manufacturing can be easy and low-cost, and relatively excellent resolution can be obtained, compared to when a shadow mask is used.
[0007] In the prior art using a solution coating process, the material used to form the hole transport layer includes a substituent that increases the solubility of the material. After the hole transport layer is coated, the emissive layer is coated on the hole transport layer by a solution coating process. In the solution coating process in which the emissive layer is formed, the underlying hole transport layer must not be dissolved in the emissive layer solution. Summary of the invention
[0008] One or more aspects of example embodiments of the present disclosure are directed to an organic layer having dissolution resistance, a composition for preparing the organic layer, and a device including the organic layer.
[0009] Additional aspects will be set forth in part in the description which follows and will be obvious from the description, or may be learned by practice of the presented embodiments.
[0010] One or more exemplary embodiments of the present disclosure provide a composition comprising: a high molecular weight compound represented by Formula 1; a non-arylamine low molecular weight compound represented by Formula 2; and a solvent:
[0011] Formula 1
[0012]
[0013] Formula 2
[0014] (Y) o .
[0015] In formula 1,
[0016] X can be substituted or unsubstituted C 3 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,
[0017] m can be an integer from 0 to 2,
[0018] R 1 , R 2 and Ar may be independently selected from 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 -C60 heteroaryl, 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 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),
[0019] k and l may each independently be an integer from 0 to 4, and
[0020] n can be an integer of 30 or greater,
[0021] In formula 2,
[0022] Y can be substituted or unsubstituted C 3 -C 60 Carbocyclic group (wherein Y does not include denoted part), and
[0023] o can be an integer of 2 or greater.
[0024] When present, the substituted C 3 -C 60 Carbocyclic, substituted C 1 -C 60 Heterocyclic, 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 At least one (eg, each) substituent of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be independently selected from:
[0025] 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;
[0026] are substituted with 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 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, 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 ) selected from at least one of C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C60 Alkynyl and C 1 -C 60 Alkoxy;
[0027] 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 groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups;
[0028] are substituted with 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, 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 ) selected from 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 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and
[0029] -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 ),
[0030] Q 1 To Q 3 , 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, C3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group,
[0031] The high molecular weight compound represented by Formula 1 may have a molecular weight of about 50,000 or more,
[0032] The non-arylamine-based low molecular weight compound represented by Formula 2 may have a molecular weight of about 10,000 or less, and
[0033] *, *' and *" may all represent a binding site with an adjacent atom.
[0034] One or more exemplary embodiments of the present disclosure provide a method for preparing an organic layer, the method comprising: providing (applying or depositing) a composition to a substrate (providing (applying or depositing) the composition on a substrate); and drying the composition at a temperature of about 150°C to about 300°C.
[0035] One or more example embodiments of the present disclosure provide an organic layer including: a high molecular weight compound represented by Formula 1; and a non-arylamine-based low molecular weight compound represented by Formula 2.
[0036] One or more exemplary embodiments of the present disclosure provide an organic light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; and an organic layer located between the first electrode and the second electrode and including an emission layer, wherein the organic layer comprises a high molecular weight compound represented by Formula 1 and a non-arylamine low molecular weight compound represented by Formula 2.
[0037] One or more exemplary embodiments of the present disclosure provide an electronic device comprising a thin film transistor and an organic light-emitting device, wherein the thin film transistor comprises a source electrode, a drain electrode, an active layer and a gate electrode, and a first electrode of the organic light-emitting device is electrically connected to one selected from the source electrode and the drain electrode of the thin film transistor. BRIEF DESCRIPTION OF THE DRAWINGS
[0038] These and / or other aspects will become apparent and more easily understood through the following description of the embodiments in conjunction with the accompanying drawings, in which:
[0039] Figure 1 is a schematic diagram of an organic light emitting device according to an embodiment of the present disclosure;
[0040] Figure 2 is a schematic diagram of an organic light emitting device according to another embodiment of the present disclosure;
[0041] Figure 3 is a schematic diagram of an organic light emitting device according to another embodiment of the present disclosure; and
[0042] Figure 4 is a schematic diagram of an organic light emitting device according to another embodiment of the present disclosure. DETAILED DESCRIPTION
[0043] Now will be more detailed with reference to the embodiment of its example shown in the accompanying drawings, wherein the same reference numerals refer to the same element all the time, and its repeated description may not be provided.In this regard, the embodiment provided may have different forms, and should not be construed as being limited to the description set forth herein.Therefore, the embodiment is described below only by reference to the accompanying drawings, to explain the aspects of this description.As used herein, the term "and / or" includes any combination and all combinations of one or more related listed items.When such as "at least one (kind / person) in ...", "one (kind / person) in ...", "selected from ...", "at least one (kind / person) selected from ..." and "one (kind / person) selected from ..." are expressed after a row of elements (elements), what is modified is the element (element) of the whole row, rather than modifying the individual element (element) in the row.
[0044] 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. In addition, when describing embodiments of the inventive concept, the use of "may" refers to "one or more embodiments of the inventive concept."
[0045] It will also be understood that the terms “comprises” and / or “comprising” as used herein specify the presence of stated features or components, but do not preclude the presence or addition of one or more other features or components.
[0046] 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. That is, for example, there may be intervening layers, regions or components.
[0047] For the convenience of explanation, the sizes of components in the drawings may be exaggerated. In other words, since the sizes and thicknesses of components in the drawings are arbitrarily shown for the convenience of explanation, the following embodiments of the present disclosure are not limited thereto.
[0048] The composition according to an embodiment of the present disclosure includes: a high molecular weight compound represented by Formula 1; a non-arylamine low molecular weight compound represented by Formula 2; and a solvent:
[0049] Formula 1
[0050]
[0051] Formula 2
[0052] (Y) o .
[0053] In formula 1,
[0054] X can be substituted or unsubstituted C 3 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,
[0055] m can be an integer from 0 to 2,
[0056] R 1 , R 2 and Ar may be independently selected from 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 monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3)、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),
[0057] k and l may each independently be an integer from 0 to 4, and
[0058] n can be an integer of 30 or greater,
[0059] In formula 2,
[0060] Y can be substituted or unsubstituted C 3 -C 60 Carbocyclic group (wherein Y does not include denoted part), and
[0061] o can be an integer of 2 or greater.
[0062] When present, the substituted C 3 -C 60 Carbocyclic, substituted C 1 -C 60 Heterocyclic, 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 60At least one (eg, each) substituent of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be independently selected from:
[0063] 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;
[0064] are substituted with 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 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, 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 ) selected from 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;
[0065] C 3 -C10 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 groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups;
[0066] are substituted with 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, 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 ) selected from at least one of C 3 -C10 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 groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and
[0067] -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 ),
[0068] Q 1 To Q 3 , 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 60Aryl, C 1 -C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group,
[0069] The high molecular weight compound represented by Formula 1 may have a molecular weight of about 50,000 or more,
[0070] The non-arylamine-based low molecular weight compound represented by Formula 2 may have a molecular weight of about 10,000 or less, and
[0071] *, *' and *" may all represent a binding site with an adjacent atom.
[0072] The molecular weight of the high molecular weight compound represented by Formula 1 may be a weight average molecular weight (M w ).
[0073] In Formula 1, when m is 2, two Xs may be the same as or different from each other.
[0074] Since Formula 2 is limited to non-aryl amine compounds, the substituted C 3 -C 60 The description of the substituents in the carbocyclic group, for example, does not include the case where Y in Formula 2 is an arylamine compound (eg, including an arylamine group).
[0075] In Formula 2, when o is two or more, two or more Ys may be the same as or different from each other.
[0076] As used herein, the term "non-arylamine compound" refers to a compound other than an arylamine compound (e.g., a compound that does not include an arylamine moiety or functional group). As used herein, the term "arylamine compound" refers to a compound in which an aryl group is attached to N (e.g., a compound that includes an arylamine moiety or functional group).
[0077] The high molecular weight compound represented by Formula 1 in the composition may have a molecular weight of about 50,000 or more, for example, about 100,000 to about 5,000,000. The high molecular weight compound represented by Formula 1 may not (eg, does not) include a cross-linkable functional group.
[0078] The non-arylamine low molecular weight compound represented by Formula 2 may have a molecular weight of about 10,000 or less, for example, a molecular weight of about 100 to about 8,000. The non-arylamine low molecular weight compound represented by Formula 2 may not (for example, not) include a cross-linkable functional group. The molecular weight of the non-arylamine low molecular weight compound represented by Formula 2 may be a weight average molecular weight (M w ).
[0079] As used herein, the term "low molecular weight" refers to a molecular weight at which high molecular weight polymer behavior does not occur (eg, excluding polymer molecules having a molecular weight outside or higher than the stated range).
[0080] When the molecular weight of the non-arylamine-based low-molecular weight compound represented by Formula 2 is low, the non-arylamine-based low-molecular weight compound cannot form a film and / or fiber, etc.
[0081] In Formula 1 and Formula 2, n and o are each independently the number of repeating units (integer) satisfying the molecular weight range of their respective compounds.
[0082] When n and o are within appropriate ranges, the stacking stability of the formed organic film (layer) can be enhanced, and the solvent resistance of the film can be improved.
[0083] In one embodiment, X of Formula 1 in the composition may be selected from substituted or unsubstituted fluorene derivatives, substituted or unsubstituted carbazole derivatives, and substituted or unsubstituted azepine derivatives.
[0084] In one embodiment, X of Formula 1 in the composition may be represented by one selected from Formula 2a to Formula 2h:
[0085]
[0086] In Formula 2a to Formula 2h,
[0087] R 11 To R 21 can be independently selected from hydrogen, 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 -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 C6 -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, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),
[0088] a1 and a2 may each independently be an integer from 1 to 4,
[0089] When present, the 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 At least one (eg, each) substituent of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be independently selected from:
[0090] 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;
[0091] are substituted with 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 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 11 )、-S(Q 11 )、-Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-P(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) selected from 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;
[0092] C 3 -C 10Cycloalkyl, 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 groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups;
[0093] are substituted with 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 21 )、-S(Q 21 )、-Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-P(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21) and -P(=O)(Q 21 )(Q 22 ) selected from 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 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and
[0094] -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),and
[0095] Q 1 To Q 3 , 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 -C10 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 groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups and terphenyl groups.
[0096] The (e.g., one or more) hydrogen sites in each of Formulae 2a to 2h may be binding sites with adjacent atoms. For example, in Formulae 2a to 2h, two bonds corresponding to divalent linking groups may exist at any hydrogen site.
[0097] When a1 and a2 are two or more, the corresponding substituents may be the same as or different from each other (the same applies to other equivalent formulae).
[0098] In one embodiment, Ar of Formula 1 in the composition may be represented by one selected from Formula 3a and Formula 3b:
[0099]
[0100] In Formula 3a and Formula 3b,
[0101] R 16 To R 18 can be independently selected from hydrogen, 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 -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, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),
[0102] a2 can be an integer from 1 to 4,
[0103] When present, the 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 At least one (eg, each) substituent of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be independently selected from:
[0104] 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;
[0105] are substituted with 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 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 11 )、-S(Q 11 )、-Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-P(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) selected from 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;
[0106] C 3 -C 10Cycloalkyl, 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 groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups;
[0107] are substituted with 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 21 )、-S(Q 21 )、-Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-P(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21) and -P(=O)(Q 21 )(Q 22 ) selected from 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 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and
[0108] -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),
[0109] Q 1 To Q 3 , 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 -C10 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group, and
[0110] * can represent the binding site with adjacent atoms.
[0111] In one embodiment, Y in Formula 2 of the composition can be represented by Formula 4a:
[0112]
[0113] In formula 4a,
[0114] R 19 It can be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, 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 -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, -C(Q 1 )(Q2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),
[0115] a3 may be an integer from 1 to 4, for example, an integer from 2 to 4,
[0116] When present, the 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 At least one (eg, each) substituent of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be independently selected from:
[0117] 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;
[0118] are substituted with 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 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 11 )、-S(Q 11 )、-Si(Q 11 )(Q 12 )(Q 13 )、-B(Q 11 )(Q 12 )、-P(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) selected from 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;
[0119] 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 groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups;
[0120] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 21 )、-S(Q 21 )、-Si(Q 21 )(Q 22 )(Q 23 )、-B(Q 21 )(Q 22 )、-P(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 ) selected from 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 -C60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and
[0121] -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),and
[0122] Q 1 To Q 3 , 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, 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 groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups and terphenyl groups.
[0123] The (e.g., one or more) hydrogen sites in formula 4a can be binding sites with adjacent atoms (groups). Formula 4a can be a monovalent group or a divalent group. For example, formula 4a is a monovalent group when the formula 4a portion is located at both (ends) of formula 2, and formula 4a is a divalent group when the formula 4a portion is located in the middle of the chain (e.g., the middle of formula 2). The individual formula 4a portions can be the same or different from each other, and can be combined together at any hydrogen site of each formula 4a portion.
[0124] In one embodiment, the high molecular weight compound represented by Formula 1 in the composition may be one selected from Compound 1 to Compound 41:
[0125] Compound 1
[0126]
[0127] Compound 2
[0128]
[0129] Compound 3
[0130]
[0131] Compound 4
[0132]
[0133] Compound 5
[0134]
[0135] Compound 6
[0136]
[0137] Compound 7
[0138]
[0139] Compound 8
[0140]
[0141] Compound 9
[0142]
[0143] Compound 10
[0144]
[0145] Compound 11
[0146]
[0147] Compound 12
[0148]
[0149] Compound 13
[0150]
[0151] Compound 14
[0152]
[0153] Compound 15
[0154]
[0155] Compound 16
[0156]
[0157] Compound 17
[0158]
[0159] Compound 18
[0160]
[0161] Compound 19
[0162]
[0163] Compound 20
[0164]
[0165] Compound 21
[0166]
[0167] Compound 22
[0168]
[0169] Compound 23
[0170]
[0171] Compound 24
[0172]
[0173] Compound 25
[0174]
[0175] Compound 26
[0176]
[0177] Compound 27
[0178]
[0179] Compound 28
[0180]
[0181] Compound 29
[0182]
[0183] Compound 30
[0184]
[0185] Compound 31
[0186]
[0187] Compound 32
[0188]
[0189] Compound 33
[0190]
[0191] Compound 34
[0192]
[0193] Compound 35
[0194]
[0195] Compound 36
[0196]
[0197] Compound 37
[0198]
[0199] Compound 38
[0200]
[0201] Compound 39
[0202]
[0203] Compound 40
[0204]
[0205] Compound 41
[0206]
[0207] In the above compound structure, * can represent the binding site with the adjacent atom.
[0208] In Compound 1 to Compound 41, n may be any appropriate number (integer) that satisfies the criterion that the molecular weight of each compound is 50,000 or more.
[0209] In one embodiment, the non-arylamine low molecular weight compound represented by Formula 2 in the composition can be selected from Compound A1 to Compound A5:
[0210] Compound A1
[0211]
[0212] Compound A2
[0213]
[0214] Compound A3
[0215]
[0216] Compound A4
[0217]
[0218] Compound A5
[0219]
[0220] In one embodiment, the solvent of the composition can be a volatile organic solvent. In one embodiment, for example, the solvent can be selected from toluene, anisole, ethyl acetate, methylene chloride, methyl benzoate, cyclohexylbenzene, tetralin and a combination thereof, but embodiments of the present disclosure are not limited thereto.
[0221] In one embodiment, the weight ratio of the high molecular weight compound represented by Formula 1 to the non-aryl amine low molecular weight compound represented by Formula 2 in the composition can be about 1:99 to about 99:1, and the concentration of the composition (e.g., the concentration of the total solids in the composition) can be in the range of about 0.5% to about 20%.
[0222] When the weight ratio of the high molecular weight compound represented by Formula 1 to the non-aryl amine low molecular weight compound represented by Formula 2 is within the above range and the concentration is within the above range, the processability and / or solvent resistance of the formed organic film can be optimized or the processability and / or solvent resistance of the formed organic film can be suitable.
[0223] The composition may be printed by an inkjet process and dried to form an organic layer.
[0224] In one embodiment, the organic layer can be prepared using a manufacturing method comprising drying the composition at a temperature of about 150°C to about 300°C for about 1 minute to about 2 hours. In one embodiment, the organic layer can be prepared using a manufacturing method comprising drying the composition at a temperature of about 200°C to about 260°C for about 10 minutes to about 1 hour. When the temperature is lower than 150°C, the resulting organic film will not be dense enough, and when the drying time is shorter than 1 minute, the solvent will remain (e.g., the solvent may not be fully dried). When the temperature is higher than 300°C, the compound will be degraded, and when the drying time is longer than 2 hours, energy will be wasted.
[0225] In one embodiment, the method of preparing the organic layer may include: providing (depositing or applying) the composition to (providing (depositing or applying) the composition on) a substrate; and drying the composition at a temperature of about 150°C to about 300°C.
[0226] In one embodiment, a method for preparing an organic layer may include: preparing a composition by mixing a high molecular weight compound represented by Formula 1, a non-arylamine low molecular weight compound represented by Formula 2, and a solvent; printing the composition on a substrate using an inkjet process; and drying the composition at a temperature of about 200° C. to about 260° C. for about 10 minutes to about 1 hour.
[0227] One or more embodiments of the present disclosure provide an organic layer including a high molecular weight compound represented by Formula 1 and a non-arylamine-based low molecular weight compound represented by Formula 2. Formula 1 and Formula 2 may each independently be the same as described above.
[0228] The organic layer including the high molecular weight compound represented by Formula 1 and the non-arylamine low molecular weight compound represented by Formula 2 can be formed by printing the above composition on a substrate using an inkjet process, and the solvent can be evaporated therefrom, so that the organic layer remains. In some embodiments, for example, the organic layer may include a high molecular weight compound represented by Formula 1 and a non-arylamine low molecular weight compound represented by Formula 2 (composed of a high molecular weight compound represented by Formula 1 and a non-arylamine low molecular weight compound represented by Formula 2).
[0229] As used herein, the expression “(the organic layer) includes at least one compound” may include the case where “(the organic layer) includes the same compound represented by Formula 1 (single compound structure)” and the case where “(the organic layer) includes two or more different compounds represented by Formula 1 (two or more compounds)”.
[0230] For example, the organic layer may include only Compound 1 as the compound described above. In this regard, Compound 1 may be present in (included in) the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include a combination of Compound 1 and Compound 2 as the compounds described above. In this regard, Compound 1 and Compound 2 may be present in the same layer (e.g., Compound 1 and Compound 2 may both be present in the emission layer), or in different layers (e.g., Compound 1 may be present in the emission layer, and Compound 2 may be present in the electron transport region).
[0231] According to another embodiment of the present disclosure, an organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer located between the first electrode and the second electrode, the organic layer including an emission layer (for example, as a sublayer), a high molecular weight compound represented by Formula 1, and a non-aromatic amine low molecular weight compound represented by Formula 2.
[0232] In one embodiment,
[0233] The first electrode of the organic light emitting device may be an anode,
[0234] The second electrode of the organic light emitting device may be a cathode,
[0235] The organic layer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode.
[0236] The hole transport region may include a hole injection layer, a hole transport layer, a buffer layer, an electron blocking layer, or any combination thereof, and
[0237] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0238] In one embodiment, the hole transport region may include an organic layer including a high molecular weight compound of Formula 1 and a non-arylamine low molecular weight compound of Formula 2. For example, the high molecular weight compound of Formula 1 and the non-arylamine low molecular weight compound of Formula 2 may form a hole transport region of the organic layer or be included in the hole transport region of the organic layer (e.g., positioned in the hole transport region of the organic layer).
[0239] In one embodiment, the hole transport layer may include a high molecular weight compound of Formula 1 and a non-arylamine low molecular weight compound of Formula 2. For example, the high molecular weight compound of Formula 1 and the non-arylamine low molecular weight compound of Formula 2 may form a hole transport layer of an organic layer or be included in the hole transport layer of an organic layer (e.g., positioned in the hole transport layer of the organic layer).
[0240] According to another aspect of the present disclosure, an electronic device includes: a thin film transistor and an organic light-emitting device, wherein the thin film transistor includes a source electrode, a drain electrode, an activation layer (or called an active layer) and a gate electrode, and a first electrode of the organic light-emitting device is electrically contacted with one selected from the source electrode and the drain electrode of the thin film transistor.
[0241] The term "organic layer" as used herein may refer to a single layer and / or a plurality of layers located between a first electrode and a second electrode of an organic light emitting device. Materials included in the "organic layer" are not limited to organic materials.
[0242] Figure 1 Description
[0243] Figure 1 1 is a schematic diagram of an organic light emitting device 10 according to an embodiment of the present disclosure. The organic light emitting device 10 includes a first electrode 110, an organic layer 150 and a second electrode 190.
[0244] 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 of the present disclosure are described.
[0245] First electrode 110
[0246] exist Figure 1 In the embodiment, a substrate may be additionally disposed below the first electrode 110 and / or above the second electrode 190. The substrate may be a glass substrate and / or a plastic substrate, each of which has excellent mechanical strength, thermal stability, transparency, surface flatness, ease of handling, and / or waterproofness.
[0247] 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.
[0248] 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, the material used to form 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.
[0249] 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 embodiment of the structure of the first electrode 110 is not limited thereto.
[0250] Organic layer 150
[0251] The organic layer 150 is located on the first electrode 110. The organic layer 150 may include an emission layer.
[0252] The organic layer 150 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 190 .
[0253] Hole transport region in the organic layer 150
[0254] 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.
[0255] The hole transport region may include at least one layer selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer.
[0256] For example, the hole transport region may have a single-layer structure or a multi-layer structure, wherein the single-layer structure includes a single layer comprising a plurality of different materials, and the multi-layer structure has 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 the constituent layers of each structure are sequentially stacked (e.g., layered) from the first electrode 110 in the order stated, but the structure of the hole transport region is not limited thereto.
[0257] The hole transport region may include an organic layer including the high molecular weight compound of Formula 1 and the non-arylamine-based low molecular weight compound of Formula 2.
[0258] In one embodiment, 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:
[0259]
[0260] Formula 201
[0261]
[0262] Formula 202
[0263]
[0264] In equation 201 and equation 202,
[0265] 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 60 Heteroarylene groups, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups, and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic groups;
[0266] 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,
[0267] xa1 to xa4 may each independently be an integer from 0 to 3,
[0268] xa5 can be an integer from 1 to 10, and
[0269] 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 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
[0270] 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 or a diphenyl-methylene.
[0271] In one or more embodiments, in equation 201 and equation 202,
[0272] L 201 To L 205 Can be independently selected from:
[0273] 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
[0274] are substituted with 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 selected from 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
[0275] 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.
[0276] In one or more embodiments, xa1 to xa4 may each independently be 0, 1 or 2.
[0277] In one or more embodiments, xa5 can be 1, 2, 3 or 4.
[0278] In one or more embodiments, R 201 To R 204 and Q 201 Can be independently selected from:
[0279] Phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthenyl, 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
[0280] are substituted with 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 10Alkyl 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 selected from 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
[0281] Q 31 To Q 33 may all independently be the same as described above.
[0282] 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:
[0283] fluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; and
[0284] are substituted with 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 10an alkyl group selected from the group consisting 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,
[0285] However, the embodiments of the present disclosure are not limited thereto.
[0286] 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 Can connect via one-touch.
[0287] 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:
[0288] carbazolyl; and
[0289] Substitutions include 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 of an alkyl 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,
[0290] However, the embodiments of the present disclosure are not limited thereto.
[0291] The compound represented by Formula 201 can also be represented by Formula 201A:
[0292] Formula 201A
[0293]
[0294] In one embodiment, the compound represented by Formula 201 can also be represented by Formula 201A(1), but the embodiments of the present disclosure are not limited thereto:
[0295] Formula 201A(1)
[0296]
[0297] In one embodiment, the compound represented by Formula 201 can also be represented by Formula 201A-1, but the embodiments of the present disclosure are not limited thereto:
[0298] Formula 201A-1
[0299]
[0300] In one embodiment, the compound represented by Formula 202 can also be represented by Formula 202A:
[0301] Formula 202A
[0302]
[0303] In one embodiment, the compound represented by Formula 202 can also be represented by Formula 202A-1:
[0304] Formula 202A-1
[0305]
[0306] In Formula 201A, Formula 201A(1), Formula 201A-1, Formula 202A, and Formula 202A-1,
[0307] L 201 To L 203 , xa1 to xa3, xa5 and R 202 To R 204 may be independently the same as described above,
[0308] R 211 and R 212 can be independently combined with R 203 are defined the same as
[0309] 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 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 and pyridyl.
[0310] 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:
[0311]
[0312]
[0313]
[0314] The thickness of the hole transport region may be approximately To about For example, approximately 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 about To about For example, approximately To about The thickness of the hole transport layer can be about To about For example, approximately To about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are all within these ranges, satisfactory hole transport characteristics may be obtained without significantly increasing the driving voltage.
[0315] The emission-assisting layer can improve the luminous efficiency by compensating the optical resonance distance according to the wavelength of the light emitted by the emission layer (for example, by adjusting the optical resonance distance in the device to match the wavelength of the light emitted from the emission layer), and the electron blocking layer can block or reduce the flow of electrons from the electron transport region. The emission-assisting layer and the electron blocking layer can each independently include the materials described above.
[0316] p-dopant
[0317] In addition to these materials, the hole transport region may also 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.
[0318] The charge generating material may be, for example, a p-dopant.
[0319] In one embodiment, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of approximately -3.5 eV or less.
[0320] The p-dopant may include at least one selected from quinone derivatives, metal oxides, and cyano-containing compounds, but embodiments of the present disclosure are not limited thereto.
[0321] For example, the p-dopant may include at least one selected from the following compounds:
[0322] Quinone derivatives (such as tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ));
[0323] Metal oxides (such as tungsten oxide and / or molybdenum oxide);
[0324] 1,4,5,8,9,12-Hexaazatriphenylene-hexanitrile (HAT-CN); and
[0325] The compound represented by formula 221,
[0326] However, the embodiments of the present disclosure are not limited thereto:
[0327]
[0328] Formula 221
[0329]
[0330] In formula 221,
[0331] 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 10 Heterocycloalkenyl, 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 the group consisting of cyano, -F, -Cl, -Br, -I, C substituted with -F1 -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:
[0332] Emission layer in the organic layer 150
[0333] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned as a red emission layer, a green emission layer, or a blue emission layer according to the sub-pixel (e.g., corresponding to the group of sub-pixels). In one or more embodiments, the emission layer may have a stacked structure including 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 may be in contact with each other or may be 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.
[0334] The emission layer may include a host and a dopant. The dopant may include at least one selected from a phosphorescent dopant and a fluorescent dopant.
[0335] The amount of the dopant in the emission layer may be 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.
[0336] The thickness of the emission layer can be approximately To about For example, approximately To about When the thickness of the emission layer is within this range, excellent light emitting characteristics can be obtained without significantly increasing driving voltage.
[0337] Subject in the emission layer
[0338] In one or more embodiments, the host may include a compound represented by Formula 301:
[0339] Formula 301
[0340] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .
[0341] In formula 301,
[0342] Ar 301 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,
[0343] xb11 can be 1, 2 or 3,
[0344] 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,
[0345] xb1 can be an integer from 0 to 5.
[0346] 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 -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 -C60 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 ),
[0347] xb21 can be an integer from 1 to 5, and
[0348] 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.
[0349] In one embodiment, Ar in Formula 301 301 Can be selected from:
[0350] naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, peryl, perylenyl, pentaphenyl, indenoanthryl, dibenzofuranyl, and dibenzothiophenyl; and
[0351] are substituted with 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 )(Q32 )、-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
[0352] 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.
[0353] When xb11 in Formula 301 is two or more, two or more Ar 301 Can connect via one-touch.
[0354] In one or more embodiments, the compound represented by Formula 301 may be represented by Formula 301-1 or Formula 301-2:
[0355] Formula 301-1
[0356]
[0357] Formula 301-2
[0358]
[0359] In Formula 301-1 and Formula 301-2,
[0360] A 301 To A 304 can be independently selected from benzene, naphthalene, phenanthrene, fluoranthene, benzo[9,10]phenanthrene, pyrene, pyridine, pyrimidine, indene, fluorene, spirobifluorene, benzofluorene, dibenzofluorene, indole, carbazole, benzocarbazole, dibenzocarbazole, furan, benzofuran, dibenzofuran, naphthofuran, benzonaphthofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthiophene, benzonaphthothiophene and dinaphthothiophene,
[0361] X 301 Can be O, S or N-[(L 304 ) xb4 -R 304],
[0362] 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 ),
[0363] xb22 and xb23 can each independently be 0, 1 or 2,
[0364] L 301 、xb1、R 301 and Q 31 To Q 33 may be independently the same as described above,
[0365] L 302 To L 304 can be independently combined with L 301 The same definition,
[0366] xb2 to xb4 may each independently be the same as defined in conjunction with xb1, and
[0367] R 302 To R 304 can be independently combined with R 301 The definition is the same.
[0368] For example, in Formula 301, Formula 301-1, and Formula 301-2, L 301 To L 304 Can be independently selected from:
[0369] 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
[0370] are substituted with 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
[0371] Q 31 To Q 33 may all independently be the same as described above.
[0372] In one embodiment, in Formula 301, Formula 301-1 and Formula 301-2, R 301 To R 304 Can be independently selected from:
[0373] 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
[0374] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C1 -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 selected from the group consisting 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
[0375] Q 31 To Q 33 may all independently be the same as described above.
[0376] In one or more embodiments, the host may include an alkaline earth metal complex. For example, the host may be selected from a beryllium (Be) complex (e.g., compound H55) and a magnesium (Mg) complex. In some embodiments, the host may be a Zn complex.
[0377] 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), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazolyl-9-yl)benzene (TCP), and compounds H1 to H55, but embodiments of the present disclosure are not limited thereto:
[0378]
[0379]
[0380]
[0381] The phosphorescent dopant included in the emission layer in the organic layer 150
[0382] The phosphorescent dopant may include an organometallic complex represented by Formula 401:
[0383] Formula 401
[0384] M(L 401 ) xc1 (L 402 ) xc2
[0385] Formula 402
[0386]
[0387] In equations 401 and 402,
[0388] 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),
[0389] 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,
[0390] L 402It 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,
[0391] X 401 To X 404 may each independently be nitrogen or carbon,
[0392] 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,
[0393] A 401 and A 402 can be independently C 5 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0394] X 405 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*'、*-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,
[0395] X 406 Can be a single bond, O or S,
[0396] 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 10Heterocycloalkyl, 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 (Q 401 ) 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,
[0397] xc11 and xc12 may each independently be an integer from 0 to 10, and
[0398] The * and *' in Formula 402 may both represent a binding site with M in Formula 401.
[0399] In one embodiment, A in equation 402 401 and A 402 They can all be independently selected from benzene, naphthalene, fluorene, spirobifluorene, indene, pyrrole, thiophene, furan, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, quinoline, isoquinoline, benzoquinoline, quinoxaline, quinazoline, carbazole, benzimidazole, benzofuran, benzothiophene, isobenzothiophene, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran and dibenzothiophene.
[0400] 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 They may both be nitrogen.
[0401] In one or more embodiments, R in equation 402 401 and R 402 Can be independently selected from:
[0402] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;
[0403] 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;
[0404] Cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl;
[0405] 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
[0406] -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
[0407] Q 401 To Q 403 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl and naphthyl, but the embodiments of the present disclosure are not limited thereto.
[0408] 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 Connect and / or two or more L 401 Two A's 402 It can be optionally connected via X as a linker 408 Connection (see Compound PD1 to Compound PD4 and Compound 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.
[0409] L in Formula 401 402 It can be a monovalent organic ligand, a divalent organic ligand or a trivalent organic ligand. 402The moiety may be selected from halogen, diketone (eg, acetylacetone), carboxylic acid (eg, picolinic acid), -C(=O), isonitrile, -CN, and phosphorus (eg, phosphine or phosphite), but the embodiments of the present disclosure are not limited thereto.
[0410] 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:
[0411]
[0412]
[0413] Fluorescent dopants in the emitting layer
[0414] The fluorescent dopant may include an arylamine compound or a styrylamine compound.
[0415] The fluorescent dopant may include a compound represented by Formula 501:
[0416] Formula 501
[0417]
[0418] In formula 501,
[0419] Ar 501 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,
[0420] 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,
[0421] xd1 to xd3 may each independently be an integer from 0 to 3,
[0422] 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 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and
[0423] xd4 can be an integer from 1 to 6.
[0424] In one embodiment, Ar in Formula 501 501 Can be selected from:
[0425] naphthyl, heptathenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, phenanthrenyl, perylenyl, pentaphenanthrenyl, indenoanthryl, and indenophenanthrenyl; and
[0426] 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 alkoxy, phenyl, biphenyl, terphenyl and naphthyl, naphthyl, heptalenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, 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,
[0427] In one or more embodiments, L in Formula 501 501 To L 503 Can be independently selected from:
[0428] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, ...
[0429] are substituted with 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 group, a naphthylene group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracene group, an anthracene group, an fluoranthenyl group, a benzo[9,10]phenanthrenyl group, a pyrenyl group, a fluorenyl group, a phenanthrenyl group, a phenanthrenyl group, a fluoranthrenyl group, a benzo[9,10]phenanthrenyl group, a py ... The compounds include phenylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothiophenylene, and pyridylene.
[0430] In one or more embodiments, R in Formula 501 501 and R 502 Can be independently selected from:
[0431] 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
[0432] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1 -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 selected from the group consisting 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
[0433] 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.
[0434] In one or more embodiments, xd4 in equation 501 may be 2, but the embodiments of the present disclosure are not limited thereto.
[0435] For example, the fluorescent dopant may be selected from Compound FD1 to Compound FD22:
[0436]
[0437]
[0438]
[0439] 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:
[0440]
[0441] Electron transport region in the organic layer 150
[0442] 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.
[0443] 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.
[0444] 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 the constituent layers of each structure are sequentially stacked (e.g., laminated) on the emission layer in the order stated. However, embodiments of the structure of the electron transport region are not limited thereto.
[0445] The electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, and / 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.
[0446] "π-electron-poor nitrogen-containing ring" means a C-containing ring having at least one *-N=*' moiety as a ring-forming part. 1 -C 60 Heterocyclic group.
[0447] For example, the "π-electron-poor nitrogen-containing ring" may be: i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' portion; ii) a heteropolycyclic group in which two or more 5- to 7-membered heteromonocyclic groups each having at least one *-N=*' portion are condensed with each other; or iii) a heteropolycyclic group in which at least one 5- to 7-membered heteromonocyclic group having at least one *-N=*' portion is condensed with at least one C 5 -C 60 A carbocyclic condensed heteropolycyclic group.
[0448] Non-limiting examples of π-electron-poor nitrogen-containing rings include 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, but embodiments of the present disclosure are not limited thereto.
[0449] For example, the electron transport region may include a compound represented by Formula 601:
[0450] Formula 601
[0451] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0452] In formula 601,
[0453] Ar 601 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,
[0454] xe11 can be 1, 2 or 3,
[0455] L 601 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,
[0456] xe1 can be an integer from 0 to 5,
[0457] 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 C6 -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)(Q 601 )、-S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),
[0458] Q 601 To Q 603 can be independently C 1 -C 10 Alkyl, C 1 -C 10 alkoxy, phenyl, biphenyl, terphenyl or naphthyl, and
[0459] xe21 can be an integer from 1 to 5.
[0460] In one embodiment, (among the total number of groups provided by Xe11 and Xe21) at least one Ar 601 group and / or at least one R 601 The group may include a π-electron-poor nitrogen-containing ring.
[0461] In one embodiment, Ar in Formula 601 601 Can be selected from:
[0462] Phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, phenanthrenyl, phenanthrenyl, phenanthrenyl, phenanthryl, phenanthroline, phenazinyl, phenanthryl ...
[0463] are substituted with 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 )(Q 32 ) is at least one selected from 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
[0464] 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.
[0465] When xe11 in Formula 601 is two or greater, two or more Ar 601 Can connect via one-touch.
[0466] In one or more embodiments, Ar in Formula 601 601 It may be anthracene.
[0467] In one or more embodiments, the compound represented by Formula 601 can also be represented by Formula 601-1:
[0468] Formula 601-1
[0469]
[0470] In formula 601-1,
[0471] 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 ), and from X 614 To X 616 At least one of the selected ones may be N,
[0472] L 611 To L 613 can be independently defined as 601 same,
[0473] xe611 to xe613 can each be independently defined to be the same as xe1,
[0474] R 611 To R 613 can be independently defined as 601 The same, and
[0475] 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.
[0476] In one embodiment, L in equation 601 601 and L in formula 601-1 611 To L 613 Can be independently selected from:
[0477] 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
[0478] are substituted with 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, phthalazine at least one selected from the group consisting of phenylene, naphthylene, 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,
[0479] However, the embodiments of the present disclosure are not limited thereto.
[0480] In one or more embodiments, xe1 in Formula 601 and xe611 to xe613 in Formula 601-1 may each independently be 0, 1, or 2.
[0481] In one or more embodiments, R in Formula 601 601 and R in formula 601-1 611 To R 613 Can be independently selected from:
[0482] 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;
[0483] are substituted with 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 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
[0484] -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),and
[0485] Q 601 and Q 602 All are independently the same as described above.
[0486] In one embodiment, 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:
[0487]
[0488]
[0489]
[0490]
[0491] In one or more embodiments, 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 BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ) and NTAZ:
[0492]
[0493] In one embodiment, the electron transport region may include a phosphine oxide compound (e.g., TSPO1 used in the following examples, etc.), but the embodiments of the present disclosure are not limited thereto. In one embodiment, a phosphine oxide compound may be used in a hole blocking layer in the electron transport region, but the embodiments of the present disclosure are not limited thereto.
[0494] The thickness of the buffer layer, the hole blocking layer and the electron control layer can be about To about For example, approximately To about When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are all within these ranges, the electron transport region can have excellent hole blocking characteristics or electron control characteristics without significantly increasing driving voltage.
[0495] The thickness of the electron transport layer can be about To about For example, approximately To about When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without significantly increasing driving voltage.
[0496] In addition to the materials described above, the electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material.
[0497] The metal-containing material may include at least one selected from an alkali metal complex and an alkaline earth metal complex. The alkali metal complex may include a metal ion selected from Li ions, Na ions, K ions, Rb ions, and Cs ions, and the alkaline earth metal complex may include a metal ion 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.
[0498] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium quinolate, LiQ) or ET-D2.
[0499]
[0500] 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 be in direct contact with the second electrode 190.
[0501] 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.
[0502] 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.
[0503] 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.
[0504] The alkaline earth metal may be selected from Mg, Ca, Sr and Ba.
[0505] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb and Gd.
[0506] The alkali metal compound, alkaline earth metal compound and rare earth metal compound may be selected from oxides and halides (eg, fluorides, chlorides, bromides and / or iodides) of alkali metals, alkaline earth metals and rare earth metals.
[0507] 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.
[0508] 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.
[0509] 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 and TbF 3 . In one embodiment, the rare earth metal compound may be selected from YbF 3 、ScF 3 、TbF 3 、YbI 3 、ScI 3 and TbI 3 , but the embodiments of the present disclosure are not limited thereto.
[0510] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may include the ions of the alkali metal, alkaline earth metal and rare earth metal as described above, and the ligands coordinated with the metal ions of the alkali metal complex, alkaline earth metal complex or rare earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.
[0511] The electron injection layer may include alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes or any combination thereof as described above (e.g., composed of alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes or any combination thereof as described above). In one or more embodiments, the electron injection layer may also include organic materials. When the electron injection layer also includes organic materials, alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes or combinations thereof may be uniformly or non-uniformly dispersed in a matrix including an organic material.
[0512] The thickness of the electron injection layer can be about To about For example, approximately To about When the thickness of the electron injection layer is within the range described above, the electron injection layer can have satisfactory electron injection characteristics without significantly increasing driving voltage.
[0513] The second electrode 190
[0514] The second electrode 190 may be located on the organic layer 150 having the above 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, each having a relatively low work function.
[0515] 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.
[0516] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.
[0517] Figures 2 to 4 Description
[0518] Figure 2 The organic light emitting device 20 includes a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190 which are sequentially stacked (eg, laminated) in the stated order. Figure 3The organic light emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second cover layer 220 which are sequentially stacked (eg, laminated) in the stated order. Figure 4 The organic light emitting device 40 includes a first capping layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 which are sequentially stacked (eg, laminated) in the stated order.
[0519] about 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 .
[0520] In the organic layer 150 of each of the organic light-emitting devices 20 and the organic light-emitting devices 40, light generated in the emission layer can pass through the first electrode 110 (which is a semi-transmissive electrode or a transmissive electrode) and the first cover layer 210 toward the outside, and in the organic layer 150 of each of the organic light-emitting devices 30 and the organic light-emitting devices 40, light generated in the emission layer can pass through the second electrode 190 (which is a semi-transmissive electrode or a transmissive electrode) and the second cover layer 220 toward the outside.
[0521] The first capping layer 210 and the second capping layer 220 may improve the external light emitting efficiency of the organic light emitting device according to the principle of constructive interference.
[0522] 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.
[0523] The first cap layer 210 and / or the second cap layer 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. Carbocyclic compounds, heterocyclic compounds and amine compounds may each be selectively substituted with a substituent containing at least one element selected from oxygen (O), nitrogen (N), sulfur (S), selenium (Se), silicon (Si), fluorine (F), chlorine (Cl), bromine (Br) and iodine (I). In one embodiment, the first cap layer 210 and / or the second cap layer 220 may each independently include amine compounds.
[0524] In one embodiment, the first capping layer 210 and / or the second capping layer 220 may each independently include a compound represented by Formula 201 and / or a compound represented by Formula 202.
[0525] In one or more embodiments, the first cap layer 210 and / or the second cap 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:
[0526]
[0527] In the above, it has been combined Figures 1 to 4 The organic light emitting device according to the embodiment of the present disclosure is described. However, the embodiment of the present disclosure is not limited thereto.
[0528] The layer constituting the hole transport region, the emission layer and the layer constituting the electron transport region can be independently formed in a specific (set or predetermined) region 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.
[0529] 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 / or approx. / second to approximately The vacuum deposition was performed at a deposition rate of 2000 Å / s.
[0530] When a layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region are formed by spin coating, the spin coating may be performed at a coating speed of about 2000 rpm to about 5000 rpm and / or at a heat treatment temperature of about 80°C to about 200°C, depending on the material to be included in the layer to be formed and the structure of the layer to be formed.
[0531] equipment
[0532] The organic light emitting device may be included in various devices or apparatuses. For example, a light emitting device, an authentication device, or an electronic device each including an organic light emitting device may be provided.
[0533] In addition to the organic light-emitting device, the light-emitting device may further include a thin film transistor including a source electrode and a drain electrode. One selected from the source electrode and the drain electrode of the thin film transistor may be electrically connected to one selected from the first electrode and the second electrode of the organic light-emitting device. The light-emitting device may be applicable to various displays, light sources, and the like.
[0534] The authentication device may be, for example, a biometric authentication device for authenticating an individual using biometric information of a biometric body (eg, fingertip, pupil, etc.).
[0535] In addition to the organic light emitting device, the authentication device may also include a biometric information collector.
[0536] The electronic device can be applied to (for example, integrated in or included in) a personal computer (for example, a mobile personal computer), a mobile phone, a digital camera, an electronic notepad, an electronic dictionary, an electronic game console, medical equipment (for example, an electronic thermometer, a blood pressure meter, a blood glucose meter, a pulse measuring device, a pulse wave measuring device, an electrocardiogram (ECG) display, an ultrasonic diagnostic device and / or an endoscope display), a fish finder, various measuring instruments, meters (for example, meters for vehicles, aircraft and / or ships) and / or a projector, etc., but the embodiments of the present disclosure are not limited thereto.
[0537] General definitions of some substituents
[0538] As used herein, the term "C 1 -C 60 "Alkyl" may refer to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, non-limiting 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" may refer to 1 -C 60 The alkyl group has a divalent group having substantially the same structure.
[0539] As used herein, the term "C 2 -C 60 "Alkenyl" may refer to 2 -C 60 The term "C" as used herein refers to a hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminal of the alkyl group, non-limiting examples of which include ethenyl, propenyl, and butenyl. 2 -C 60 "Alkenylene" may refer to 2 -C 60 An alkenyl group is a divalent group having substantially the same structure.
[0540] As used herein, the term "C 2 -C 60 "Alkynyl" may refer to 2 -C 60 The term "C" as used herein refers to a hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminal of the alkyl group, non-limiting examples of which include ethynyl and propynyl.2 -C 60 "Alkynylidene" may refer to 2 -C 60 Alkynyl groups are divalent groups having substantially the same structure.
[0541] As used herein, the term "C 1 -C 60 "Alkoxy" may refer to -OA 101 (Among them, A 101 C 1 -C 60 The monovalent group represented by an alkyl group is a methoxy group, an ethoxy group, and an isopropoxy group.
[0542] As used herein, the term "C 3 -C 10 "Cycloalkyl" may refer to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, non-limiting examples of which include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "Cycloalkyl" may refer to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, non-limiting examples of which include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. 3 -C 10 "Cycloalkylene" may refer to 3 -C 10 The cycloalkyl group has a divalent group having substantially the same structure.
[0543] As used herein, the term "C 1 -C 10 The term “heterocycloalkyl” as used herein may refer to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom and 1 to 10 carbon atoms, and non-limiting examples thereof include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and tetrahydrothienyl. 1 -C 10 "Heterocycloalkylene" may refer to 1 -C 10 The heterocycloalkyl group has a divalent group having substantially the same structure.
[0544] As used herein, the term "C 3 -C 10 The term "cycloalkenyl" may refer to a group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and having no aromaticity (e.g., C 3 -C 10 The term "cycloalkenyl" as used herein is a monovalent monocyclic group (not aromatic) of which non-limiting examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. 3 -C 10 "Cycloalkenylene" may refer to 3 -C 10 The cycloalkenyl group is a divalent group having substantially the same structure.
[0545] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl group" may refer to a monovalent monocyclic group having at least one hetero atom selected from N, O, Si, P and S as ring-forming 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" may refer to 1 -C 10 The heterocycloalkenyl group has a divalent group having substantially the same structure.
[0546] As used herein, the term "C 6 -C 60 The term "aryl" may refer to a monovalent group having a carbocyclic aromatic system including 6 to 60 carbon atoms. 6 -C 60 The arylene group may refer to a divalent group having a carbocyclic aromatic system including 6 to 60 carbon atoms. 6 -C 60 Non-limiting examples of aryl groups include 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 (eg, condensed) to each other.
[0547] As used herein, the term "C 1 -C 60 The term “heteroaryl” as used herein may refer to a monovalent group having a heterocyclic 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 The term "heteroarylene group" may refer to a divalent group having a heterocyclic 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 Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. 1 -C 60 Heteroaryl and C 1-C 60 When the heteroarylene group includes two or more rings, the rings may be fused (eg, condensed) to each other.
[0548] As used herein, the term "C 6 -C 60 "Aryloxy" may refer to -OA 102 (Among them, A 102 C 6 -C 60 The term "C 6 -C 60 "Arylthio" may refer to -SA 103 (Among them, A 103 C 6 -C 60 A monovalent group represented by an aryl group.
[0549] As used herein, the term "monovalent non-aromatic condensed polycyclic group" may refer to a monovalent group having two or more rings condensed with each other, 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 molecule has no aromaticity). A non-limiting example of a monovalent non-aromatic condensed polycyclic group is a fluorenyl group. As used herein, the term "divalent non-aromatic condensed polycyclic group" may refer to a divalent group having substantially the same structure as a monovalent non-aromatic condensed polycyclic group.
[0550] The term "monovalent non-aromatic condensed heteropolycyclic group" as used herein may refer to a monovalent group having two or more rings condensed with each other, at least one heteroatom selected from N, O, Si, P and S as ring-forming atoms other than carbon atoms (e.g., having 1 to 60 carbon atoms), and having no aromaticity in its entire molecular structure (e.g., the entire molecule has no aromaticity). A non-limiting example of a monovalent non-aromatic condensed heteropolycyclic group may be a carbazolyl group. The term "divalent non-aromatic condensed heteropolycyclic group" as used herein may refer to a divalent group having substantially the same structure as a monovalent non-aromatic condensed heteropolycyclic group.
[0551] As used herein, the term "C 4 -C 60 "Carbocyclic group" may refer to a monocyclic or polycyclic group having 4 to 60 carbon atoms, wherein the ring atoms are only carbon atoms. 4 -C 60 The carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. 4 -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. 4 -C 60The number of substituents of the carbocyclic group, C 4 -C 60 The carbocyclic group may be a trivalent group or a tetravalent group.
[0552] As used herein, the term "C 1 -C 60 The term "heterocyclic group" may refer to a group consisting of at least one heteroatom selected from N, O, Si, P and S other than carbon (the number of carbon atoms may be 1 to 60) as a ring-forming atom. 4 -C 60 The carbocyclic group has a group having substantially the same structure.
[0553] In this specification, when present, substituted C 4 -C 60 Carbocyclic, substituted C 1 -C 60 Heterocyclic, substituted C 1 -C 20 Alkylene, substituted C 2 -C 20 Alkenylene, 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 60 Arylene, 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 At least one (eg, each) substituent of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be independently selected from:
[0554] 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;
[0555] are substituted with 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 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, 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 ) selected from at least one of C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C60 Alkynyl and C 1 -C 60 Alkoxy;
[0556] 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 groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups;
[0557] are substituted with 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, 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 ) selected from 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 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and
[0558] -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
[0559] 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 10Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, C substituted with at least one selected from deuterium, -F and cyano 1 -C 60 alkyl, C substituted with at least one selected from deuterium, -F and cyano 6 -C 60 Aryl, biphenyl and terphenyl.
[0560] The term "Ph" as used herein refers to phenyl, the term "Me" as used herein refers to methyl, the term "Et" as used herein refers to ethyl, the term "ter-Bu" or "Bu" as used herein refers to ethyl. t ” refers to tert-butyl, and the term “OMe” as used herein refers to methoxy.
[0561] As used herein, the term "biphenyl" refers to a "phenyl group substituted with a phenyl group". In other words, a "biphenyl group" is a group having C 6 -C 60 Aryl (specifically, phenyl) is a substituted phenyl group as a substituent.
[0562] 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 An aryl group (specifically, a phenyl group substituted with a phenyl group) is a phenyl group as a substituent.
[0563] Unless otherwise defined, *, *' and *" as used herein all refer to the binding position to the adjacent atom in the corresponding formula.
[0564] Hereinafter, the compounds according to the embodiments of the present disclosure and the organic light-emitting devices according to the embodiments of the present disclosure will be described in more detail with reference to the synthesis examples and examples. The expression "using B instead of A" used in describing the synthesis examples means using the same molar equivalent of B instead of the same molar equivalent of A.
[0565] Example
[0566] Ink preparation
[0567] 1. Preparation of Ink 1
[0568] High molecular weight compound 1 having a molecular weight of 150,000 and low molecular weight compound A1 were mixed at a weight ratio of 8:2, and anisole was used as a solvent, thereby preparing ink 1 having a concentration of 1.5%.
[0569] 2. Preparation of Ink 2
[0570] Ink 2 was prepared in substantially the same manner as Ink 1, except that Compound 2 having a molecular weight of 150,000 was used instead of Compound 1 having a molecular weight of 150,000.
[0571] 3. Preparation of Ink 3
[0572] Ink 3 was prepared in substantially the same manner as Ink 1, except that Compound 1 having a molecular weight of 70,000 was used instead of Compound 1 having a molecular weight of 150,000.
[0573] 4. Preparation of Ink 4
[0574] Ink 4 was prepared in substantially the same manner as Ink 1, except that Compound 2 having a molecular weight of 45,000 was used instead of Compound 1 having a molecular weight of 150,000.
[0575] 5. Preparation of Ink 5
[0576] Ink 5 was prepared in substantially the same manner as Ink 1, except that Compound 26 having a molecular weight of 100,000 was used instead of Compound 1 having a molecular weight of 150,000, and Compound A2 was used instead of low molecular weight Compound A1.
[0577] 6. Preparation of Ink 6
[0578] Ink 6 was prepared in substantially the same manner as Ink 1, except that Compound 32 having a molecular weight of 100,000 was used instead of Compound 1 having a molecular weight of 150,000, and Compound A2 was used instead of low molecular weight Compound A1.
[0579] 7. Preparation of Ink 7
[0580] Ink 7 was prepared in substantially the same manner as Ink 2, except that the arylamine compound EM-1 was used instead of the low molecular weight compound A1.
[0581] Compound 1
[0582]
[0583] Compound 2
[0584]
[0585] Compound 26
[0586]
[0587] Compound 32
[0588]
[0589] Compound A1
[0590]
[0591] Compound A2
[0592]
[0593] Compound EM-1
[0594]
[0595] Measurement of Solvent Resistance of Organic Films
[0596] Ink 1 to Ink 7 were used to prepare Each film was dried at 230° C. for 30 minutes. Then, the ultraviolet (UV) absorbance of each film was measured (measurement 1).
[0597] 50 μL of methyl benzoate was dropped on each film and left to stand for 30 minutes, after which the solvent was absorbed with a wiper. Each film was left to stand at a temperature of 100° C. for 1 minute, and the UV absorbance of each film was measured (measurement 2).
[0598] The "residual rate" for each film was calculated using the following equation:
[0599] Remaining rate = (UV measurement after leaving the solvent to stand for 30 minutes) / (UV measurement before solvent treatment) = Measurement 2 / Measurement 1.
[0600] When the solvent resistance is high, the difference between Measurement 2 and Measurement 1 should be small or very small, and when the solvent resistance is low, because one or more compounds of the organic layer are dissolved and removed by the solvent (in this case, the solvent is methyl benzoate), Measurement 2 should be lower than Measurement 1. Therefore, when the remaining rate is high (close to 100%), the solvent resistance is high.
[0601] The calculated residual ratios are shown in Table 1.
[0602] Table 1
[0603]
[0604] Referring to Table 1, it was confirmed that the organic layer prepared using the composition including the high molecular weight compound represented by Formula 1 having a molecular weight of 50,000 or more and the non-arylamine-based low molecular weight compound having a molecular weight of 10,000 or less had high solvent resistance.
[0605] Fabrication of organic light-emitting devices
[0606] Example 1
[0607] As the anode, Corning 15Ω / cm 2 The ITO glass substrate was cut into a size of 50 mm × 50 mm × 0.7 mm, and was ultrasonicated with isopropyl alcohol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes. PEDOT-PSS was coated on the ITO glass substrate and then heat-treated at 150°C for 30 minutes to form a film with a thickness of The hole injection layer is formed by spraying ink 1 on the hole injection layer using an inkjet process to form a hole injection layer with a thickness of The hole transport layer was dried at 230° C. for 30 minutes. Compound A as a fluorescent host and compound B as a fluorescent dopant were co-deposited on the hole transport layer at a weight ratio of 95:5 to form a layer with a thickness of Compound ET1 is deposited on the emission layer to form an emission layer with a thickness of The electron transport layer is formed by depositing LiF on the electron transport layer to form a layer with a thickness of An electron injection layer is formed, and Al is deposited on the electron injection layer to form a layer with a thickness of The second electrode (cathode) is formed on the organic light-emitting device, thereby completing the manufacture of the organic light-emitting device.
[0608]
[0609] Examples 2 to 5 and Comparative Examples 1 and 2
[0610] Another organic light-emitting device was manufactured in substantially the same manner as in Example 1, except that Ink 2 to Ink 7 shown in Table 1 were each used in forming the hole transport layer.
[0611] The luminous efficiencies of Examples 1 to 5 and Comparative Examples 1 and 2 were measured at 700 nit using a luminance meter PR650, and the results are shown in Table 2.
[0612] Table 2
[0613]
[0614] Referring to Table 2, it was confirmed that the organic light emitting devices of Examples 1 to 5 exhibited excellent results compared with Comparative Examples 1 and 2 (the organic light emitting device of Comparative Example 2 was not operable).
[0615] The organic layer according to the embodiment of the present disclosure has strong dissolution resistance in the solution coating process. Therefore, when the composition is used, the solution coating process can be easily applied, and the manufacture of an organic light-emitting device including high-resolution pixels can be facilitated.
[0616] 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.
[0617] 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 of the present disclosure as defined by the claims and their equivalents.
Claims
1. A composition, the composition include: A high molecular weight compound represented by Formula 1; A non-arylamine low molecular weight compound represented by Formula 2; as well as Solvent: Formula 1 Formula 2 (Y) o , Among them, in formula 1, X is represented by one selected from Formula 2a, Formula 2c to Formula 2h: Wherein, in Formula 2a, Formula 2c to Formula 2h, R 11 , R 12 , R 14 To R 21 are independently selected from hydrogen, 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 -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, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ), a1 and a2 are independently integers from 1 to 4, When present, the substituted C 1 -C 60 Alkyl, the substituted C 2 -C 60 Alkenyl, the substituted C 2 -C 60 Alkynyl, the substituted C 1 -C 60 Alkoxy, the substituted C 3 -C 10 Cycloalkyl, the substituted C 1 -C 10 Heterocycloalkyl, the substituted C 3 -C 10 Cycloalkenyl, the substituted C 1 -C 10 Heterocycloalkenyl, the substituted C 6 -C 60 Aryl, the substituted C 6 -C 60 Aryloxy, the substituted C 6 -C 60 Arylthio, the substituted C 1 -C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group is independently 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 and C 1 -C 60 Alkoxy; are substituted with 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 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 11 )、-S(Q 11 )、-Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-P(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) selected from 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; 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 groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups; are substituted with 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 21 )、-S(Q 21 )、-Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 ), -P(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 ) selected from 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 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、 -C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ), Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group, and One or more hydrogen sites in each of Formula 2a, Formula 2c to Formula 2h are binding sites with adjacent atoms, m is an integer from 0 to 2, R 1 , R 2 and Ar are independently selected from 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 monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ), k and l are each independently an integer from 0 to 4, and n is an integer of 30 or greater, In formula 2, Y is substituted or unsubstituted C 3 -C 60 Carbocyclic group, wherein Y does not include represents the part, and o is an integer of 2 or greater, When present, the substituted C 3 -C 60 Carbocyclic group, the substituted C 1 -C 60 Alkyl, the substituted C 2 -C 60 Alkenyl, the substituted C 2 -C 60 Alkynyl, the substituted C 1 -C 60 Alkoxy, the substituted C 3 -C 10 Cycloalkyl, the substituted C 1 -C 10 Heterocycloalkyl, the substituted C 3 -C 10 Cycloalkenyl, the substituted C 1 -C 10 Heterocycloalkenyl, the substituted C 6 -C 60 Aryl, the substituted C 6 -C 60 Aryloxy, the substituted C 6 -C 60 Arylthio, the substituted C 1 -C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group is independently 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 and C 1 -C 60 Alkoxy; are substituted with 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 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, 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 ) selected from 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; 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 groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups; are substituted with 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, 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 ) selected from 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 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and -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 )和-P(=O)(Q 31 )(Q 32 ), Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group, The high molecular weight compound represented by Formula 1 has a molecular weight of 50,000 or more, The non-arylamine low molecular weight compound represented by Formula 2 has a molecular weight of 10,000 or less, and *, *' and *" all indicate the binding sites with adjacent atoms.
2. The composition according to claim 1, in, Ar is represented by one selected from Formula 3a and Formula 3b: Wherein, in Formula 3a and Formula 3b, R 16 To R 18 are independently selected from hydrogen, 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 -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, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ), a2 is an integer from 1 to 4, When present, the substituted C 1 -C 60 Alkyl, the substituted C 2 -C 60 Alkenyl, the substituted C 2 -C 60 Alkynyl, the substituted C 1 -C 60 Alkoxy, the substituted C 3 -C 10 Cycloalkyl, the substituted C 1 -C 10 Heterocycloalkyl, the substituted C 3 -C 10 Cycloalkenyl, the substituted C 1 -C 10 Heterocycloalkenyl, the substituted C 6 -C 60 Aryl, the substituted C 6 -C 60 Aryloxy, the substituted C 6 -C 60 Arylthio, the substituted C 1 -C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group is independently 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 and C 1 -C 60 Alkoxy; are substituted with 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 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 11 )、-S(Q 11 )、-Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-P(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) selected from 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; 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 groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups; are substituted with 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 21 )、-S(Q 21 )、-Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-P(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 ) selected from 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 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ), Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group, and *Indicates the binding site with the adjacent atom.
3. The composition according to claim 1, in, Y is represented by Formula 4a: Wherein, in Formula 4a, R 19 is selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, 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 -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, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ), a3 is an integer from 1 to 4, When present, the substituted C 1 -C 60 Alkyl, the substituted C 2 -C 60 Alkenyl, the substituted C 2 -C 60 Alkynyl, the substituted C 1 -C 60 Alkoxy, the substituted C 3 -C 10 Cycloalkyl, the substituted C 1 -C 10 Heterocycloalkyl, the substituted C 3 -C 10 Cycloalkenyl, the substituted C 1 -C 10 Heterocycloalkenyl, the substituted C 6 -C 60 Aryl, the substituted C 6 -C 60 Aryloxy, the substituted C 6 -C 60 Arylthio, the substituted C 1 -C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group is independently selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy; are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, hydrazine, hydrazone, 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 11 )、-S(Q 11 )、-Si(Q 11 )(Q 12 )(Q 13 )、-B(Q 11 )(Q 12 )、-P(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) selected from 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; 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 groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups; are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 21 )、-S(Q 21 )、-Si(Q 21 )(Q 22 )(Q 23 )、-B(Q 21 )(Q 22 )、-P(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 ) selected from 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 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )和-P(=O)(Q 31 )(Q 32 ), Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group, and One or more hydrogen sites in Formula 4a are bonding sites to adjacent atoms.
4. The composition according to claim 1, in, The non-arylamine low molecular weight compound represented by Formula 2 is one selected from Compound A1 to Compound A5: Compound A1 Compound A2 Compound A3 Compound A4 Compound A5 5. A composition, the composition include: A high molecular weight compound represented by one of the compounds in compound group 1; A non-arylamine low molecular weight compound represented by Formula 2; as well as Solvent: Compound Group 1 Compound 1 Compound 2 Compound 3 Compound 6 Compound 7 Compound 8 Compound 9 Compound 10 Compound 11 Compound 12 Compound 13 Compound 14 Compound 15 Compound 16 Compound 17 Compound 18 Compound 19 Compound 20 Compound 21 Compound 22 Compound 23 Compound 24 Compound 25 Compound 26 Compound 27 Compound 28 Compound 29 Compound 30 Compound 31 Compound 32 Compound 33 Compound 34 Compound 35 Compound 36 Compound 37 Compound 38 Compound 39 Compound 40 Compound 41 In compound group 1, * indicates the binding site with the adjacent atom. Formula 2 (Y) o , Y is substituted or unsubstituted C 3 -C 60 Carbocyclic group, wherein Y does not include represents the part, and o is an integer of 2 or greater, When present, the substituted C 3 -C 60 At least one substituent in the carbocyclic group is independently 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 and C 1 -C 60 Alkoxy; are substituted with 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 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, 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 ) selected from 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; 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 groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups; are substituted with 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, 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 ) selected from 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 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and -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 ), Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group, *' and *" both indicate the binding sites with adjacent atoms. 6 . An organic layer comprising the composition according to claim 1 or 5 .
7. An organic light-emitting device, the organic light-emitting device include: a first electrode; a second electrode, facing the first electrode; as well as The organic layer according to claim 6 is located between the first electrode and the second electrode, and comprises an emission layer.
8. The organic light emitting device according to claim 7, in: The first electrode is an anode, The second electrode is a cathode, and The organic layer also includes: i) a hole transport region located between the first electrode and the emission layer, the hole transport region including a hole injection layer, a hole transport layer, a buffer layer, an electron blocking layer or any combination thereof; and ii) an electron transport region located between the emission layer and the second electrode, the electron transport region including 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, in: The high molecular weight compound represented by Formula 1 and the non-arylamine-based low molecular weight compound represented by Formula 2 are included in the hole transport region.
