Light emitting device and electronic apparatus including same
The introduction of a specific emission auxiliary layer with Formula 1 dopants enhances OLED performance by improving light emitting efficiency and lifespan.
Patent Information
- Application Number
- CN202410805437.6
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-06-26
- Filing Date
- 2024-06-21
- Publication Date
- 2024-12-27
AI Technical Summary
Existing organic light emitting devices (OLEDs) face challenges in achieving high light emitting efficiency and lifespan characteristics.
Incorporating an emission auxiliary layer with specific dopants represented by Formula 1, comprising cobalt, copper, zinc, gallium, germanium, zirconium, ruthenium, rhodium, palladium, silver, rhenium, platinum, or gold, and specific bonding configurations, to enhance the performance of the OLEDs.
The solution significantly improves the light emitting efficiency and lifespan of OLEDs by optimizing the emission layer and auxiliary layer composition.
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Figure CN119212430A_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0081640 filed on June 26, 2023 in the Korean Intellectual Property Office, and all rights arising therefrom, the entire contents of which are incorporated herein by reference. Technical Field
[0003] The present subject matter relates to light emitting devices and electronic devices including the same. Background Art
[0004] Among the light emitting devices, an organic light emitting device (OLED) is a self-emitting device having improved characteristics in terms of viewing angle, response time, brightness, driving voltage, and response speed. In addition, the OLED can produce a full-color image.
[0005] In an example, an organic light emitting device includes an anode, a cathode, and an organic layer arranged between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be arranged between the anode and the emission layer, and an electron transport region may be arranged between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. Holes and electrons may recombine in the emission layer to generate excitons. Excitons may transition from an excited state to a ground state, thereby generating light. Summary of the invention
[0006] Provided are a light emitting device having excellent light emitting efficiency and lifespan characteristics and an electronic device including the same.
[0007] Additional aspects will be set forth in part in the detailed description which follows and, in part, will be apparent from the detailed description, or may be learned by practice of the presented exemplary embodiments described herein.
[0008] According to one aspect, a light emitting device includes a first electrode, a second electrode facing the first electrode, and an intermediate layer arranged between the first electrode and the second electrode, wherein the intermediate layer includes an emission layer and an emission auxiliary layer, the emission auxiliary layer is arranged between the emission layer and the first electrode, the emission layer includes a first host and a first dopant, the emission auxiliary layer includes a second host and a second dopant, and the second dopant is represented by Formula 1:
[0009] Formula 1
[0010]
[0011] Among them, in formula 1,
[0012] M1 is cobalt, copper, zinc, gallium, germanium, zirconium, ruthenium, rhodium, palladium, silver, rhenium, platinum, or gold,
[0013] X 1 is O, S, N(R'), P(R'), B(R'), C(R')(R"), or Si(R')(R"),
[0014] X 2 -X 4 are each independently C or N,
[0015] In X 1 and M 1 The bond between them is a covalent bond, selected from X 2 and M 1 The key between X 3 and M 1 The keys between 4 and M 1 One of the bonds between is a covalent bond, and the remaining two are coordination bonds.
[0016] Y 1 and Y 3 -Y 5 are each independently C or N,
[0017] X 2 and Y 3 , X 2 and Y 4 , Y 4 and Y 5 , X 51 and Y 3 , and X 51 and Y 5 are connected to each other via chemical bonds,
[0018] Cyclo 1 CY 2 CY 3 , and ring CY 4 Each independently is C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups,
[0019] Cyclo 5 CY 2 CY 3 , and M 1 To form a 6-membered cyclometalated ring,
[0020] T 1 For single bonds, double bonds, *-N(R 5 )-*'、*-B(R5 )-*'、*-P(R 5 )-*'、*-C(R 5 )(R 6 )-*'、*-Si(R 5 )(R 6 )-*'、*-Ge(R 5 )(R 6 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*'、*-C(R 5 )=*'、*=C(R 5 )-*'、*-C(R 5 )=C(R 6 )-*', *-C(=S)-*', or *-C≡C-*', wherein * and *' each represent a binding site with an adjacent atom,
[0021] X 51 O, S, N (R 7 )、C(R 7 )(R 8 )、Si(R 7 )(R 8 )、Ge(R 7 )(R 8 )、C(=O)、N、
[0022] C(R 7 )、Si(R 7 ), or Ge(R 7 ),
[0023] R 1 -R 8 R', and R" are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, 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 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10Cycloalkyl, 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 7 -C 60 Alkyl aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-Ge(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(=O)(Q 8 )(Q 9 ), or -P(Q 8 )(Q 9 ),
[0024] a1-a4 are each independently an integer of 0-20,
[0025] R 1 , R 3 , or R 4 At least one of is not hydrogen,
[0026] R 1Two or more of are optionally linked to each other to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,
[0027] R 2 Two or more of are optionally linked to each other to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,
[0028] R 3 Two or more of are optionally linked to each other to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,
[0029] R 4 Two or more of are optionally linked to each other to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,
[0030] R 1 -R 4 Two or more of are optionally linked to each other to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,
[0031] R 10a By referring to the R 1 description and understand,
[0032] Substituted C 1 -C60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 1 -C 60 Alkylthio, 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 7 -C 60 Alkyl aryl, substituted C 7 -C 60 Arylalkyl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 Alkyl heteroaryl, substituted C 2 -C 60 Heteroarylalkyl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 Substituents of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are:
[0033] Deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio,
[0034] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, 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 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-Ge(Q 13)(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(=O)(Q 18 )(Q 19 )、-P(Q 18 )(Q 19 ), or a combination thereof,
[0035] C each unsubstituted or substituted with at least one of the following 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 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 7 -C 60 Arylalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 2 -C 60 Heteroarylalkyl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-Ge(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(=O)(Q 28 )(Q 29 )、-P(Q 28 )(Q 29 ), or a combination thereof,
[0036] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-Ge(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39 ), or -P(Q 38 )(Q 39 ),or
[0037] Its combination, and
[0038] Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, 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 1 -C 60 Alkylthio, 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 7 -C 60 Alkyl aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C60 a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
[0039] According to another aspect, an electronic device includes the light emitting device. BRIEF DESCRIPTION OF THE DRAWINGS
[0040] The above and other aspects, features, and advantages of certain exemplary embodiments will become more apparent from the following detailed description considered in conjunction with the accompanying drawings, in which:
[0041] Figure 1 is a schematic diagram of a light emitting device according to one or more embodiments. DETAILED DESCRIPTION
[0042] Exemplary embodiments will now be described in further detail, examples of which are illustrated in the accompanying drawings. In this regard, the exemplary embodiments may have different forms and should not be construed as being limited to the detailed description set forth herein. Therefore, exemplary embodiments are described below with reference to the accompanying drawings to illustrate some aspects and features. As used herein, the term "and / or" includes any and all combinations of one or more of the related enumerated items. Expressions such as "at least one (kind) of" when before or after a list of elements modify the entire list of elements and do not modify the individual elements of the list.
[0043] The terms used herein are only used for the purpose of describing one or more exemplary embodiments and are not intended to be restrictive. As used herein, the singular forms "a (kind) (indefinite article) (a, an)" and "said (the)" are also intended to include plural forms, unless the context clearly indicates otherwise. Mentioning an element in a claim and then mentioning "said" element includes one element and multiple elements. The term "or" means "and / or". It will be further understood that the term "comprising" or "including" when used in this specification indicates that there are stated features, regions, wholes, steps, operations, elements, and / or components, but does not exclude the presence or addition of one or more other features, regions, wholes, steps, operations, elements, components, and / or their sets.
[0044] It will be understood that although the terms first, second, third, etc. can be used to describe various elements, components, regions, layers and / or parts in this article, these elements, components, regions, layers and / or parts should not be limited by these terms. These terms are only used to distinguish an element, component, region, layer or part from other elements, components, regions, layers or parts. Therefore, without departing from the teaching of the present embodiment, the first element, component, region, layer or part discussed below can be referred to as the second element, component, region, layer or part.
[0045] Exemplary embodiments are described herein with reference to cross-sectional views as schematic diagrams of idealized embodiments. Thus, deviations from the shapes of the figures as a result of, for example, manufacturing techniques and / or tolerances are to be expected. Therefore, the embodiments described herein should not be construed as being limited to the specific shapes of the regions as illustrated herein, but rather include deviations in shape caused by, for example, manufacturing. For example, a region illustrated or described as flat may typically have rough and / or nonlinear features. Moreover, the illustrated sharp corners may be rounded. Therefore, the regions shown in the figures are schematic in nature and their shapes are not intended to illustrate the precise shapes of the regions and are not intended to limit the scope of the claims.
[0046] It will be understood that when an element is referred to as being “on” another element, it can be in direct contact with the other element or intervening elements may exist therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements.
[0047] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of this disclosure and the relevant art, and will not be interpreted in an idealized or overly formal sense unless clearly so defined herein.
[0048] As used herein, "about" or "approximately" includes the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art taking into account the measurement in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations, or within ±10% or 5% relative to the stated value.
[0049] According to one aspect, a light emitting device is provided, comprising: a first electrode; a second electrode facing the first electrode; and an intermediate layer arranged between the first electrode and the second electrode, wherein the intermediate layer comprises an emission layer and an emission auxiliary layer, the emission auxiliary layer is arranged between the emission layer and the first electrode, the emission layer comprises a first host and a first dopant, the emission auxiliary layer comprises a second host and a second dopant, and the second dopant is represented by Formula 1:
[0050] Formula 1
[0051]
[0052] In formula 1, M 1It is cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au).
[0053] X 1 is O, S, N(R'), P(R'), B(R'), C(R')(R"), or Si(R')(R").
[0054] X 2 -X 4 Each is independently C or N.
[0055] In X 1 and M 1 The bond between them is a covalent bond, selected from X 2 and M 1 The key between X 3 and M 1 The keys between 4 and M 1 One of the bonds between them is a covalent bond, and the remaining two bonds are coordination bonds.
[0056] Y 1 and Y 3 -Y 5 Each is independently C or N.
[0057] X 2 and Y 3 , X 2 and Y 4 , Y 4 and Y 5 , X 51 and Y 3 , and X 51 and Y 5 They are connected to each other via chemical bonds.
[0058] Cyclo 1 CY 2 CY 3 , and ring CY 4 Each independently is C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic group.
[0059] Cyclo 5 CY 2 CY 3 , and M 1 To form a 6-membered cyclometalated ring. In other words, in Formula 1, M 1 , X 2, Y 4 , and X 3 The four members of the 6-membered cyclometallated ring are defined.
[0060] T 1 For single bonds, double bonds, *-N(R 5 )-*'、*-B(R 5 )-*'、*-P(R 5 )-*'、*-C(R 5 )(R 6 )-*'、*-Si(R 5 )(R 6 )-*'、*-Ge(R 5 )(R 6 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*'、*-C(R 5 )=*'、*=C(R 5 )-*'、*-C(R 5 )=C(R 6 )-*', *-C(=S)-*', or *-C≡C-*', wherein * and *' are each a binding site to an adjacent atom.
[0061] X 51 O, S, N (R 7 )、C(R 7 )(R 8 )、Si(R 7 )(R 8 )、Ge(R 7 )(R 8 )、C(=O)、N、
[0062] C(R 7 )、Si(R 7 ), or Ge(R 7 ).
[0063] R 1 -R 8 R', and R" are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, 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 7 -C 60 Alkyl aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-Ge(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(=O)(Q 8 )(Q 9 ), or -P(Q 8 )(Q 9 ).
[0064] a1-a4 are each independently an integer of 0-20.
[0065] For example, in one or more embodiments, a1-a4 may each independently be 0, 1, 2, 3, 4, or 5.
[0066] In formula 1, R 1 , R 3 , or R 4 At least one of is not hydrogen.
[0067] R 1 Two or more of are optionally linked to each other to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic group.
[0068] R 2 Two or more of are optionally linked to each other to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic group.
[0069] R 3 Two or more of are optionally linked to each other to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic group.
[0070] R 4 Two or more of are optionally linked to each other to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic group.
[0071] R 1 -R 4 Two or more of are optionally linked to each other to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic group.
[0072] R 10a By reference to R as provided herein 1 description and understand.
[0073] 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 1 -C 60 Alkylthio, 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 7 -C 60 Alkyl aryl, substituted C 7 -C 60 Arylalkyl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 Alkyl heteroaryl, substituted C 2 -C 60 Heteroarylalkyl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 Substituents of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are:
[0074] Deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio;
[0075] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, 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 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-Ge(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(=O)(Q 18 )(Q 19 )、-P(Q 18 )(Q 19 ), or a combination thereof;
[0076] C each unsubstituted or substituted with at least one of the following 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 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, 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 7 -C 60 Alkyl aryl, C 7 -C 60 Arylalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 2 -C 60 Heteroarylalkyl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-Ge(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(=O)(Q 28 )(Q 29 )、-P(Q 28 )(Q 29 ), or a combination thereof;
[0077] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34)(Q 35 )、-Ge(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39 ), or -P(Q 38 )(Q 39 );or
[0078] Its combination.
[0079] Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, 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 1 -C 60 Alkylthio, 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 7 -C 60 Alkyl aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
[0080] In one or more embodiments, M 1 It may be platinum (Pt).
[0081] In one or more embodiments, X 1 Can be O or S.
[0082] In one or more embodiments, X 2 and X 4 can be N, and X 3 Can be C.
[0083] In one or more embodiments,
[0084] i)X 2 and X 4 Can be N, X respectively 3 Can be C, in X 2 and M 1 The bond between X 4 and M 1 The bond between can be a coordination bond, and in X 3 and M 1 The bond between them can be a covalent bond,
[0085] ii)X 2 and X 3 Can be N, X respectively 4 Can be C, in X 2 and M 1 The bond between X 3 and M 1 The bond between can be a coordination bond, and in X 4 and M 1 The bond between them can be a covalent bond, or
[0086] iii)X 3 and X 4 Can be N, X respectively 2 Can be C, in X3 and M 1 The bond between X 4 and M 1 The bond between can be a coordination bond, and in X 2 and M 1 The bond between them can be a covalent bond.
[0087] In one or more embodiments, Y 1 and Y 3 -Y 5 Can each be C.
[0088] In one or more embodiments, in Formula 1, ring CY 1 CY 2 CY 3 , and ring CY 4 Each may independently be i) a first ring, ii) a second ring, iii) a fused ring group in which at least two first rings are fused to each other, iv) a fused ring group in which at least two second rings are fused to each other, or v) a fused ring group in which at least one first ring is fused to at least one second ring.
[0089] The first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a thiole group, a germanol group, a borolide group, a phosphole group, a selenophene group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azathiole group, an azagermanol group, an azaborol group, an azaphosphole group, or an azaselenophene group.
[0090] The second ring may be an adamantane group, a norbornane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, a cyclohexane group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
[0091] In one or more embodiments, CY 1 CY 2 CY 3 , and ring CY 4 can be independently a cyclopentane group, a cyclohexane group, a cyclohexene group, a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, group, 1,2,3,4-tetrahydronaphthalene group, cyclopentadiene group, pyrrole group, furan group, thiophene group, thiorrole group, boroheterocyclopentadiene group, phosphocyclopentadiene group, germanoheterocyclopentadiene group, selenophene group, indene group, indole group, benzofuran group, benzothiophene group, benzothiorrole group, benzoborole group, benzophosphocyclopentadiene group, benzogermanocyclopentadiene group, benzoselenophene group, fluorene group, carbazole group, dibenzofuran group, dibenzothiophene group, dibenzothiorrole group, dibenzoborole group, dibenzophosphocyclopentadiene group, dibenzogermanocyclopentadiene group, dibenzoselenophene group, benzofluorene group, benzocarbazole group, naphthobenzofuran group, naphthobenzothiophene group, naphthobenzo benzothiorrole group, naphthobenzoborole group, naphthobenzophosphole group, naphthobenzogermanol group, naphthobenzoselenophene group, dibenzofluorene group, dibenzocarbazole group, dinaphthofuran group, dinaphthothiophene group, dinaphthothiorrole group, dinaphthoborole group, dinaphthophosphole group, dinaphthogermanol group, dinaphthoselenophene group, indenophenanthrene group, indolephenanthrene group, phenanthrenyl group, phenanthrenylbenzofuran group, phenanthrenylbenzothiophene group, phenanthrenylbenzothiorrole group, phenanthrenylbenzoborole group, phenanthrenylbenzophosphole group, phenanthrenylbenzogermanol group, phenanthrenylbenzoselenophene group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindene group, azaindole group, azabenzofuran group, azabenzothiophene group, azabenzosilole group, azabenzoborole group, azabenzophosphole group, azabenzogermanole group, azabenzoselenophene group, azafluorene group, azacarbazole group, azadibenzofuran group, azadibenzothiophene group, azadibenzosilole group, azadibenzoborole group, azadibenzophosphole group, azadibenzogermanole group, azadibenzoselenophene group, azafluorene group, azacarbazole group, azadibenzofuran group, azadibenzothiophene group, azadibenzosilole group, azadibenzoborole group, azadibenzophosphole group, azadibenzogermanole group, azadibenzoselenophene group, azabenzofluorene group, azabenzocarbazole group, azanaphthobenzofuran group, azanaphthobenzothiophene group A group, an azanaphthobenzothiole group, an azanaphthobenzoborole group, an azanaphthobenzophosphole group, an azanaphthobenzogermane group, an azanaphthobenzoselenophene group, an azadibenzofluorene group, an azadibenzocarbazole group, an azadinaphthofuran group, an azadinaphthothiophene group, an azadinaphthothiole group, an azadinaphthoborole group, an azadinaphthophosphole group, an azadinaphthogermane group, an azadinaphthoselenophene group, an azaindenophenanthrene group, an azaindolinphenanthrene group, an azaphenanthrenebenzofuran group, an azaphenanthrenebenzothiophene group, an azaphenanthrenebenzothiole group, an azaphenanthrenebenzoborole group, an azaphenanthrenebenzoborole group, an azaphenanthrenebenzophosphole group, an azaphenanthrenebenzogermane group, an azaphenanthrenebenzoselenophene group, an azaphenanthrenebenzoborole ... cyclopentadiene group, azaphenanthrobenzophosphocyclopentadiene group, azaphenanthrobenzogermanocyclopentadiene group, azaphenanthrobenzoselenophene group, azadibenzothiophene 5-oxide group, aza9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, benzoquinoline group, benzoisoquinoline group, benzoquinoxaline group, benzoquinazoline group, phenanthroline group, phenanthridine group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group azole group, thiadiazole group, azathiazole group, azaborole group, azaphosphole group, azagermanol group, azaselenophene group, benzopyrrole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiazole group, benzisothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, adamantane group, norbornane group, norbornene group, a phenyl group fused to an adamantane group, a phenyl group fused to a norbornane group, a pyridine group fused to an adamantane group, or a pyridine group fused to a norbornane group.
[0092] In one or more embodiments, CY 1 CY 2 CY 3, and ring CY 4 The benzophenone group, the benzofuran group, the anthracene group, the phenanthrene group, the fluorene group, the carbazole group, the dibenzofuran group, the dibenzothiophene group, the dibenzosilole group, the dibenzoborole group, the dibenzophosphole group, the dibenzogermanole group, the dibenzoselenophene group, the benzofluorene group, the benzocarbazole group, the naphthobenzofuran group, the naphthobenzothiophene group, the naphthobenzosilole group, the naphthobenzoborole group, the naphthobenzophosphole group, the naphthobenzogermanole group, the naphthobenzoselenophene group, the dibenzofluorene group, the dibenzocarbazole group, the dinaphthofuran group, the dinaphthothiophene group, the dinaphthosilole group, the dinaphthoborole group, the dibenzophosphole group, the dibenzogermanole group, the dibenzoselenophene group, the dibenzofluorene group, the dibenzocarbazole group, the dinaphthofuran group, the dinaphthothiophene group, the dinaphthosilole group, the dinaphthoborole group, the dibenzophosphole group, the dibenzogermanole group, the dibenzoselenophene group, the Naphthophosphoside group, dinaphthogermanoside group, dinaphthoselenophene group, indenophenanthrene group, indolephenanthrene group, phenanthrobenzofuran group, phenanthrobenzothiophene group, phenanthrobenzosilole group, phenanthrobenzoborole group, phenanthrobenzophosphoside group, phenanthrobenzogermanoside group, phenanthrobenzoselenophene group, azafluorene group, azacarbazole group, azadibenzofuran group, azadibenzothiophene group, azadibenzosilole group, azadibenzoborole group, azadibenzophosphoside group, azadibenzogermanoside group, azadibenzoselenophene group, azabenzofluorene group, azabenzocarbazole group, azanaphthobenzofuran group , azanaphthobenzothiophene group, azanaphthobenzothiorrole group, azanaphthobenzoborole group, azanaphthobenzophosphole group, azanaphthobenzogermanole group, azanaphthobenzoselenophene group, azadibenzofluorene group, azadibenzocarbazole group, azadinaphthofuran group, azadinaphthothiophene group, azadinaphthothiorrole group, azadinaphthoborole group, azadinaphthophosphole group, azadinaphthogermanole group, azadinaphthoselenophene group, azaindenophenanthrene group, azaindolophenanthrene group, azaphenanthrenebenzofuran group, azaphenanthrenebenzothiophene group, azaphenanthrenebenzothiorrole group, azaphenanthrenebenzoborole group a diene group, an azaphenanthrobenzophosphole group, an azaphenanthrobenzogermane group, an azaphenanthrobenzoselenophene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, a benzoquinazoline group, a phenanthroline group, a phenanthridine group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, a norbornene group, a phenyl group fused to an adamantane group, a phenyl group fused to a norbornane group, a pyridine group fused to an adamantane group, or a pyridine group fused to a norbornane group.
[0093] In one or more embodiments, T 1 Can be a single bond.
[0094] In one or more embodiments, X 51 Can be N(R 7 ).
[0095] In one or more embodiments, N(R 7 ) may be a group represented by formula N:
[0096] Formula N
[0097]
[0098] Among them, in formula N,
[0099] Cyclo 51 Can be C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups,
[0100] L 51 may be a single bond or may be unsubstituted or substituted with at least one R 10a Substituted phenyl groups,
[0101] a51-a53, b51, c51, and c52 can each independently be 0, 1, 2, 3, 4, or 5, and
[0102] R 51 , R 52 , A 51 , and A 52 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, 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 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-Ge(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(=O)(Q 8 )(Q 9 ), or -P(Q 8 )(Q 9 ), where R 10a , Q 1 -Q 9 , and substituents of the substituted groups are as defined herein.
[0103] In one or more embodiments, R 1 -R 8 R', R' and R" may each independently be:
[0104] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, or C 1 -C 20 Alkylthio;
[0105] Each of the following C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, or C 1 -C 20 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C 1 -C 20 alkyl)cyclopentyl, (C 1 -C 20 alkyl)cyclohexyl, (C 1 -C 20 alkyl)cycloheptyl, (C 1 -C 20 Alkyl)cyclooctyl, (C 1 -C 20 Alkyl) adamantyl, (C 1 -C 20 Alkyl) norbornyl, (C 1 -C 20 Alkyl) norbornene, (C 1 -C 20 alkyl)cyclopentenyl, (C 1 -C 20 alkyl)cyclohexenyl, (C 1 -C 20 alkyl)cycloheptenyl, (C 1 -C 20alkyl)bicyclo[1.1.1]pentyl, (C 1 -C 20 alkyl)bicyclo[2.1.1]hexyl, (C 1 -C 20 alkyl) bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, or a combination thereof;
[0106] cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzo Thiphenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 1 -C 20 alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C 1 -C20 alkyl)cyclopentyl, (C 1 -C 20 alkyl)cyclohexyl, (C 1 -C 20 alkyl)cycloheptyl, (C 1 -C 20 Alkyl)cyclooctyl, (C 1 -C 20 Alkyl) adamantyl, (C 1 -C 20 Alkyl) norbornyl, (C 1 -C 20 Alkyl) norbornene, (C 1 -C 20 alkyl)cyclopentenyl, (C 1 -C 20 alkyl)cyclohexenyl, (C 1 -C 20 alkyl)cycloheptenyl, (C 1 -C 20 alkyl)bicyclo[1.1.1]pentyl, (C 1 -C 20 alkyl)bicyclo[2.1.1]hexyl, (C 1 -C 20 alkyl) bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, or a combination thereof; or
[0107] -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-Ge(Q 3 )(Q 4 )(Q 5 )、-B(Q 6)(Q 7 )、-P(=O)(Q 8 )(Q 9 ), or -P(Q 8 )(Q 9 ),and
[0108] Q 1 -Q 9 Can be independently:
[0109] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H, or -CD 2 CDH 2 ;or
[0110] n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl, each unsubstituted or substituted with at least one of the following: deuterium, C 1 -C 10 Alkyl, phenyl, or a combination thereof.
[0111] In one or more embodiments, R 1 , R 3 , and R 4 Can be independently:
[0112] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , cyano, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkyl, substituted or unsubstituted C6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 a heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
[0113] In one or more embodiments, the light emitting device may satisfy at least one of conditions 1 to 3:
[0114] Condition 1
[0115] R with quantity a1 1 At least one of the
[0116] Condition 2
[0117] Amount of R is a3 3 At least one of the
[0118] Condition 3
[0119] R with quantity a4 4 At least one of is not hydrogen.
[0120] In one or more embodiments, the light-emitting device may satisfy (i) condition 1, (ii) condition 2, (iii) condition 3, (iv) conditions 1 and 2, (v) conditions 2 and 3, (vi) conditions 1 and 3, or (vii) conditions 1, 2, and 3.
[0121] In one or more embodiments, the The group represented may be a group represented by one of the formulae CY1-1 to CY1-48:
[0122]
[0123]
[0124] Among them, in formulas CY1-1 to CY1-48,
[0125] Y 1 Same as described in this article,
[0126] X 19Can be C(R 19a )(R 19b )、N(R 19 ), O, S, or Si (R 19a )(R 19b ), R 19 , R 19a , and R 19b Each of them is related to the R 1 Same as described,
[0127] *' represents the X in formula 1 1 or M 1 The binding site, and
[0128] * indicates the ring CY in formula 1 5 binding site.
[0129] In one or more embodiments, the The group represented may be a group represented by one of the formulae CY2-1 to CY2-20:
[0130]
[0131] Wherein, in formulas CY2-1 to CY2-20,
[0132] X 2 and X 51 each being the same as described herein,
[0133] * indicates the ring CY in formula 1 1 The binding site
[0134] *' represents the same as M in formula 1 1 The binding site, and
[0135] *" indicates the ring CY in formula 1 3 binding site.
[0136] In one or more embodiments, the The group represented may be a group represented by one of the formulae CY3-1 to CY3-26:
[0137]
[0138]
[0139] Wherein, in formulas CY3-1 to CY3-26,
[0140] X 3 Same as described in this article,
[0141] X 39Can be C(R 39a )(R 39b )、N(R 39 ), O, S, or Si (R 39a )(R 39b ),
[0142] R 39 , R 39a , and R 39b As described in this article about R 3 As described,
[0143] * indicates the same as T in Formula 1 1 The binding site
[0144] *' represents the same as M in formula 1 1 The binding site, and
[0145] *" indicates the ring CY in formula 1 2 binding site.
[0146] In one or more embodiments, the The group represented may be a group represented by one of the formulae CY4-1 to CY4-48:
[0147]
[0148]
[0149] Among them, in formulas CY4-1 to CY4-48,
[0150] X 4 Same as described in this article,
[0151] X 49 Can be C(R 49a )(R 49b )、N(R 49 ), O, S, or Si (R 49a )(R 49b ),
[0152] R 49 , R 49a , and R 49b As described in this article about R 4 As described,
[0153] * indicates the same as T in Formula 1 1 The binding site, and
[0154] *' represents the same as M in formula 1 1 binding site.
[0155] In one or more embodiments, the second dopant may be represented by at least one of the compounds of [Group 1-1] to [Group 1-4]:
[0156] [Group 1-1]
[0157]
[0158] [Group 1-2]
[0159]
[0160]
[0161]
[0162]
[0163]
[0164]
[0165]
[0166]
[0167]
[0168]
[0169]
[0170]
[0171]
[0172] [Group 1-3]
[0173]
[0174]
[0175]
[0176]
[0177]
[0178] [Group 1-4]
[0179]
[0180] The first dopant may be different from the second dopant. In one or more embodiments, the first dopant may be represented by Formula 2:
[0181] Formula 2
[0182] M 2 (L 1 ) n1 (L 2 ) n2
[0183] Among them, in formula 2,
[0184] M 2 It can be iridium (Ir), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au).
[0185] L 1 may be a ligand represented by Formula 2-1, and L 2 It may be a ligand represented by Formula 2-2.
[0186] n1 and n2 may each independently be 1 or 2, and the sum of n1 and n2 may be 3.
[0187] Formula 2-1
[0188]
[0189] Formula 2-2
[0190]
[0191] In formulas 2-1 and 2-2, Y 1 -Y 4 They may each independently be C or N.
[0192] Ring A 1 , Ring A 2 , Ring A 3 , and Ring A 4 Can be independently C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic group.
[0193] W 1 -W 4 may be independently a single bond, unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10aSubstituted C 1 -C 30 Heterocyclic group.
[0194] d1-d4 and e1-e4 may each independently be an integer of 0-20.
[0195] For example, in one or more embodiments, d1-d4 and e1-e4 may each independently be an integer from 0 to 3.
[0196] Z 1 -Z 4 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, 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 1 -C 60 Alkylthio, 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 7 -C 60 Alkyl aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1-C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q 41 )(Q 42 )、-Si(Q 43 )(Q 44 )(Q 45 )、-Ge(Q 43 )(Q 44 )(Q 45 )、-B(Q 46 )(Q 47 )、-P(=O)(Q 48 )(Q 49 ), or -P(Q 48 )(Q 49 ).
[0197] Z 1 Two or more of are optionally linked to each other to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic group.
[0198] Z 2 Two or more of are optionally linked to each other to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic group.
[0199] Z 1 and Z 2 Two or more of are optionally linked to each other to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic group.
[0200] Z 3 Two or more of are optionally linked to each other to form an unsubstituted or substituted with at least one R 10a Substituted C5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic group.
[0201] Z 4 Two or more of are optionally linked to each other to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic group.
[0202] Z 3 and Z 4 Two or more of are optionally linked to each other to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic group.
[0203] Q 41 -Q 49 Each can be as described in this article about Q 1 As described, and R 10a As for R in Formula 1 10a As described.
[0204] The substituted C in Formula 2 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 1 -C 60 Alkylthio, 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 7-C 60 Alkyl aryl, substituted C 7 -C 60 Arylalkyl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 Alkyl heteroaryl, substituted C 2 -C 60 Heteroarylalkyl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 Substituents of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be as described with respect to the substituents in Formula 1.
[0205] In one or more embodiments, M 2 It may be iridium (Ir).
[0206] In one or more embodiments, L 1 and L 2 Can be different from each other.
[0207] In one or more embodiments, Y 1 and Y 3 Can be N, and Y 2 and Y 4 Can each be C.
[0208] In one or more embodiments, Ring A 1 , Ring A 2 , Ring A 3 , and Ring A 4 can be independently a cyclopentane group, a cyclohexane group, a cyclohexene group, a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, group, 1,2,3,4-tetrahydronaphthalene group, cyclopentadiene group, pyrrole group, furan group, thiophene group, thiorrole group, boroheterocyclopentadiene group, phosphocyclopentadiene group, germanoheterocyclopentadiene group, selenophene group, indene group, indole group, benzofuran group, benzothiophene group, benzothiorrole group, benzoborole group, benzophosphocyclopentadiene group, benzogermanocyclopentadiene group, benzoselenophene group, fluorene group, carbazole group, dibenzofuran group, dibenzothiophene group, dibenzothiorrole group, dibenzoborole group, dibenzophosphocyclopentadiene group, dibenzogermanocyclopentadiene group, dibenzoselenophene group, benzofluorene group, benzocarbazole group, naphthobenzofuran group, naphthobenzothiophene group, naphthobenzo benzothiorrole group, naphthobenzoborole group, naphthobenzophosphole group, naphthobenzogermanol group, naphthobenzoselenophene group, dibenzofluorene group, dibenzocarbazole group, dinaphthofuran group, dinaphthothiophene group, dinaphthothiorrole group, dinaphthoborole group, dinaphthophosphole group, dinaphthogermanol group, dinaphthoselenophene group, indenophenanthrene group, indolephenanthrene group, phenanthrenyl group, phenanthrenylbenzofuran group, phenanthrenylbenzothiophene group, phenanthrenylbenzothiorrole group, phenanthrenylbenzoborole group, phenanthrenylbenzophosphole group, phenanthrenylbenzogermanol group, phenanthrenylbenzoselenophene group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindene group, azaindole group, azabenzofuran group, azabenzothiophene group, azabenzosilole group, azabenzoborole group, azabenzophosphole group, azabenzogermanol group, azabenzoselenophene group, azafluorene group, azacarbazole group, azadibenzofuran group, azadibenzothiophene group, azadibenzo Silole group, azadibenzoborole group, azadibenzophosphole group, azadibenzogermanol group, azadibenzoselenophene group, azabenzofluorene group, azabenzocarbazole group, azanaphthobenzofuran group, azanaphthobenzothiophene group, azanaphthobenzosilole group, azanaphthobenzoborole group, azanaphthobenzophosphole group , azanaphthobenzogermanyl heterocyclopentadiene group, azanaphthobenzoselenophene group, azadibenzofluorene group, azadibenzocarbazole group, azadinaphthofuran group, azadinaphthothiophene group, azadinaphthosilole group, azadinaphthoboryl heterocyclopentadiene group, azadinaphthophospholyl group, azadinaphthogermanyl heterocyclopentadiene group, azadinaphthoselenophene group, azaindenophenanthrene group , azaindolylphenanthrene group, azaphenanthrenebenzofuran group, azaphenanthrenebenzothiophene group, azaphenanthrenebenzothiorrole group, azaphenanthrenebenzoborole group, azaphenanthrenebenzophosphole group, azaphenanthrenebenzogermanole group, azaphenanthrenebenzoselenophene group, azadibenzothiophene 5-oxide group, aza9H-fluorene-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, benzoquinoline group, benzoisoquinoline group, benzoquinoxaline group, benzoquinazoline group, phenanthroline group, phenanthridine group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, azathiorrole group, azaborole group, aza a phosphocyclopentadiene group, an azagermanocyclopentadiene group, an azaselenophene group, a benzopyrrole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzisoxazole group, a benzothiazole group, a benzisothiazole group, a benzoxadiazole group, a benzothiadiazole group, a pyridopyrrole group, a pyridopyrazole group, a pyridoimidazole group, a pyridoxazole group, a pyridisoxazole group, a pyridothiazole group, a pyridisothiazole group, a pyridoxadiazole group, a pyridothiadiazole group, a pyrimidopyrrole group, a pyridopyrazole group, a pyridoimidazole group, a pyridoxazole group, a pyridisoxazole group, a pyridothiazole group, a pyridoisothiazole group, a pyridoxadiazole group, a pyridothiadiazole group, a pyrimidopyrrole group, a pyridopyrazole group, a pyridoisox ...o a pyrimidine group, a pyrimidopyrazole group, a pyrimidoimidazole group, a pyrimidoxazole group, a pyrimidisoxazole group, a pyrimidothiazole group, a pyrimidisothiazole group, a pyrimidoxadiazole group, a pyrimidothiadiazole group, a naphthopyrrole group, a naphthopyrazole group, a naphthoimidazole group, a naphthooxazole group, a naphthoisoxazole group, a naphthothiazole group, a naphthoisothiazole group, a naphthooxadiazole group, a naphthothiadiazole group, a phenanthropyrrole group, a phenanthropyrazole group, a phenanthroimidazole group, a phenanthrooxazole group, a phenanthroisoxazole group A phenyl group, a phenyl group condensed with a cyclohexane group, a phenyl group condensed with a phenyl group, a pyridine group condensed with a cyclohexane group, or a pyridine group condensed with a phenyl group. ,
[0209] In one or more embodiments, Ring A 3 It may be i) a polycyclic group in which two or more 5-membered rings are fused to each other, ii) a polycyclic group in which two or more 6-membered rings are fused to each other, or iii) a polycyclic group in which at least one 5-membered ring and at least one 6-membered ring are fused to each other.
[0210] The 5-membered ring can be a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a silole group, a borocyclopentadiene group, a phosphole group, a germanocyclopentadiene group, a selenophene group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, or an azathiorrole group.
[0211] The 6-membered ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
[0212] In one or more embodiments, Ring A 3It may be an indene group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzogermanol group, a benzoselenophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzogermanol group, a dibenzoselenophene group, a benzofluorene group, a benzocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a naphthobenzosilole group, a naphthobenzoborole group, a naphthobenzophosphole group, a naphthobenzogermanol group, a naphthobenzoselenophene group, a dibenzofluorene group, a dibenzocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a naphthobenzosilole group, a naphthobenzoborole group, a naphthobenzophosphole group, a naphthobenzogermanol group, a naphthobenzoselenophene group, a dibenzofluorene group, a dibenzofluorene group, a dibenzo A benzocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, a dinaphthosilole group, a dinaphthoborole group, a dinaphthophosphoside group, a dinaphthogermanol group, a dinaphthoselenophene group, an indenophenanthrene group, an indolephenanthrene group, a phenanthrenyl group, a phenanthrenylbenzofuran group, a phenanthrenylbenzothiophene group, a phenanthrenylbenzosilole group, a phenanthrenylbenzoborole group, a phenanthrenylbenzophosphoside group, a phenanthrenylbenzogermanol group, a phenanthrenylbenzoselenophene group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindene group, an azaindole group, an azabenzofuran group, an azabenzothiophene group, an azabenzosilole group, an aza A benzoborole group, an azabenzophosphoside group, an azabenzogermanoside group, an azabenzoselenophene group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphoside group, an azadibenzogermanoside group, an azadibenzoselenophene group, an azabenzofluorene group, an azabenzocarbazole group, an azanaphthobenzofuran group, an azanaphthobenzothiophene group, an azanaphthobenzosilole group, an azanaphthobenzoborole group, an azanaphthobenzophosphoside group, an azanaphthobenzogermanoside group, an azanaphthobenzoselenophene group group, azadibenzofluorene group, azadibenzocarbazole group, azadinaphthofuran group, azadinaphthothiophene group, azadinaphthothiorrole group, azadinaphthoborole group, azadinaphthophosphole group, azadinaphthogermane group, azadinaphthoselenophene group, azaindenophenanthrene group, azaindolphenanthrene group, azaphenanthrenebenzofuran group, azaphenanthrenebenzothiophene group, azaphenanthrenebenzothiorrole group, azaphenanthrenebenzoborole group, azaphenanthrenebenzophosphole group, azaphenanthrenebenzogermane group, azaphenanthrenebenzoselenophene group, azadibenzothiophene 5-oxide group, aza9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, benzoquinoline group, benzoisoquinoline group, benzoquinoxaline group, benzoquinazoline group, phenanthroline group, phenanthridine group, benzopyrrole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiazole group, benzisothiazole group, benzoxadiazole group, benzothiadiazole group, pyrrolidine ... benzimidazolyl group, benzoxazole group, benzisoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, benzo a pyrimidopyrrole group, a pyridopyrazole group, a pyridoimidazole group, a pyridooxazole group, a pyridoisoxazole group, a pyridothiazole group, a pyridoisothiazole group, a pyridooxadiazole group, a pyridothiadiazole group, a pyrimidopyrrole group, a pyrimidopyrazole group, a pyrimidoimidazole group, a pyrimidooxazole group, a pyrimidoisoxazole group, a pyrimidothiazole group, a pyrimidoisothiazole group, a pyrimidooxadiazole group, pyrimidothiadiazole group, naphthopyrrole group, naphthopyrazole group, naphthoimidazole group, naphthooxazole group, naphthoisoxazole group, naphthothiazole group, naphthoisothiazole group, naphthooxadiazole group, naphthothiadiazole group, phenanthropyrrole group, phenanthropyrazole group, phenanthroimidazole group, phenanthrooxazole group, phenanthroisoxazole group, phenanthrothiazole group, phenanthroisothiazole group, phenanthrooxadiazole group, phenanthrothiadiazole group , a furanopyridine group, a benzofuranopyridine group, a thienopyridine group, a benzothienopyridine group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, a norbornene group, a phenyl group condensed with a cyclohexane group, a phenyl group condensed with a norbornane group, a pyridine group condensed with a cyclohexane group, or a pyridine group condensed with a norbornane group. ,
[0213] In one embodiment, Ring A 1 and Ring A 3 Can be different from each other.
[0214] In another embodiment, Ring A 1 and Ring A 3 Can be the same as each other.
[0215] In one embodiment, Ring A 2 and Ring A 4 Can be different from each other.
[0216] In another embodiment, Ring A 2 and Ring A 4 Can be the same as each other.
[0217] In one or more embodiments, Ring A 1 Contains Y 1 Monocyclic group, ring A 2 Contains Y 2 A monocyclic group, and ring A 4 Contains Y4 The monocyclic groups of may each be a 6-membered ring.
[0218] In one or more embodiments, Ring A 3 Contains Y 3 The monocyclic group may be a 6-membered ring.
[0219] In one or more embodiments, Ring A 3 Contains Y 3 The monocyclic group may be a 5-membered ring.
[0220] In one or more embodiments, e1 and d1 may each be different from 0, and at least one Z 1 Deuterated C 1 -C 20 Alkyl, -Si(Q 43 )(Q 44 )(Q 45 ), or -Ge(Q 43 )(Q 44 )(Q 45 ).
[0221] In one or more embodiments, Ring A 4 Can be C 8 -C 30 Polycyclic groups.
[0222] In one or more embodiments, the first dopant may satisfy at least one of conditions (1) to (4):
[0223] Condition (1)
[0224] In formula 2-1, e1 and d1 are not 0, and
[0225] At least one Z 1 Including deuterium
[0226] Condition (2)
[0227] In formula 2-1, e2 and d2 are not 0, and
[0228] At least one Z 2 Including deuterium
[0229] Condition (3)
[0230] In formula 2-2, e3 and d3 are not 0, and
[0231] At least one Z 3 Including deuterium
[0232] Condition (4)
[0233] In formula 2-2, e4 and d4 are not 0, and
[0234] At least one Z 4 Including deuterium.
[0235] In one or more embodiments, the The group represented may be a group represented by one of formulae A1-1 to A1-3:
[0236]
[0237] Among them, in formulas A1-1 to A1-3,
[0238] Z 11 -Z 14 Each of them is related to Z in this article 1 Same as described,
[0239] R 10a Same as described above,
[0240] a14 can be an integer from 0 to 4.
[0241] a18 can be an integer from 0 to 8.
[0242] *' represents the same as M in formula 2 2 The binding site, and
[0243] *" indicates the same as ring A 2 binding site.
[0244] In one or more embodiments, the The group represented may be a group represented by one of the formulae NR1 to NR48:
[0245]
[0246]
[0247]
[0248] Wherein, in formulas NR1 to NR48,
[0249] Y 39 Can be O, S, Se, N-[W 3 -(Z 3 ) e3 ]、C(Z 39a )(Z 39b ), or Si(Z 39a )(Z 39b ),
[0250] W 3 , Z 3, and e3 are each as described herein, and Z 39a and Z 39b As described in this article about Z 3 As described,
[0251] *' represents the same as M in formula 2 2 The binding site, and
[0252] *" indicates the same as ring A 4 binding site.
[0253] In one or more embodiments, the The group represented by and the group represented by in Formula 2-2 The groups represented may each independently be a group represented by one of the formulae CR1 to CR29:
[0254]
[0255]
[0256] Wherein, in formulas CR1 to CR29,
[0257] Y 49 Can be O, S, Se, N-[W 2 -(Z 2 ) e2 ]、N-[W 4 -(Z 4 ) e4 ]、C(Z 29a )(Z 29b )、C(Z 49a )(Z 49b )、Si(Z 29a )(Z 29b ), or Si(Z 49a )(Z 49b ),
[0258] W 2 , W 4 , Z 2 , Z 4 , e2, and e4 are each the same as described herein, and Z 29a and Z 29b Each of them is related to Z in this article 2 The same as described, and Z 49a and Z 49b Each of them is related to Z in this article 4 Same as described,
[0259] Y 21 -Y 24 can be independently N or C,
[0260] Ring A 40 Can be C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups,
[0261] * indicates the same as M in Formula 2 2 The binding site, and
[0262] *" indicates the same as ring A 1 or Ring A 3 binding site.
[0263] Formulas CR24 to CR29 are composed of The group represented may be a group represented by one of the formulae CR(1) to CR(13):
[0264]
[0265] Wherein, in formulas CR(1) to CR(13),
[0266] Y 49 As described herein, and
[0267] Y 31 -Y 34 and Y 41 -Y 48 They may each independently be C or N.
[0268] In one or more embodiments, R in Formula 1, 2-1, and 2-2 1 -R 8 , R', R", and Z 1 -Z 4 can be independently hydrogen, deuterium, -F, -CH 3 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 2 -C 10 Alkenyl, C 1 -C 10 Alkoxy, C 1 -C 10an alkylthio group, a group represented by one of formulae 9-1 to 9-39, a group represented by one of formulae 9-1 to 9-39 in which at least one hydrogen is replaced by deuterium, a group represented by one of formulae 9-1 to 9-39 in which at least one hydrogen is replaced by -F, a group represented by one of formulae 9-201 to 9-227, a group represented by one of formulae 9-201 to 9-227 in which at least one hydrogen is replaced by deuterium, a group represented by one of formulae 9-201 to 9-227 in which at least one hydrogen is replaced by -F, a group represented by one of formulae 10-1 to 10-1 a group represented by one of the formulae 10-1 to 10-129 in which at least one hydrogen is replaced by deuterium, a group represented by one of the formulae 10-1 to 10-129 in which at least one hydrogen is replaced by -F, a group represented by one of the formulae 10-201 to 10-350, a group represented by one of the formulae 10-201 to 10-350 in which at least one hydrogen is replaced by deuterium, a group represented by one of the formulae 10-201 to 10-350 in which at least one hydrogen is replaced by -F, -Si(Q 3 )(Q 4 )(Q 5 ), or -Ge(Q 3 )(Q 4 )(Q 5 )(where Q 3 -Q 5 Each is the same as described in this article):
[0269]
[0270]
[0271]
[0272]
[0273]
[0274]
[0275]
[0276]
[0277]
[0278] In formulae 9-1 to 9-39, 9-201 to 9-227, 10-1 to 10-129, and 10-201 to 10-350, * represents a bonding site with an adjacent atom, "Ph" is a phenyl group, "TMS" is a trimethylsilyl group, and "TMG" is a trimethylgermyl group.
[0279] The “group represented by one of formulae 9-1 to 9-39 in which at least one hydrogen is replaced by deuterium” and the “group represented by one of formulae 9-201 to 9-227 in which at least one hydrogen is replaced by deuterium” may be, for example, a group represented by one of formulae 9-501 to 9-514 or 9-601 to 9-636:
[0280]
[0281]
[0282] The “group represented by one of formulae 9-1 to 9-39 in which at least one hydrogen is replaced by —F” and the “group represented by one of formulae 9-201 to 9-227 in which at least one hydrogen is replaced by —F” may be, for example, a group represented by one of formulae 9-701 to 9-710:
[0283]
[0284] The “group represented by one of formulae 10-1 to 10-129 in which at least one hydrogen is replaced by deuterium” and the “group represented by one of formulae 10-201 to 10-350 in which at least one hydrogen is replaced by deuterium” may each be, for example, a group represented by one of formulae 10-501 to 10-553:
[0285]
[0286]
[0287] The “group represented by one of formulae 10-1 to 10-129 in which at least one hydrogen is replaced by —F” and the “group represented by one of formulae 10-201 to 10-350 in which at least one hydrogen is replaced by —F” may each be, for example, a group represented by one of formulae 10-601 to 10-617:
[0288]
[0289] In one or more embodiments, the first dopant may be at least one compound of [Group 2-1] to [Group 2-7]:
[0290] [Group 2-1]
[0291]
[0292]
[0293]
[0294]
[0295]
[0296]
[0297]
[0298]
[0299]
[0300]
[0301]
[0302]
[0303]
[0304]
[0305] [Group 2-2]
[0306]
[0307]
[0308]
[0309]
[0310]
[0311] [Group 2-3]
[0312]
[0313]
[0314]
[0315]
[0316] [Group 2-4]
[0317]
[0318]
[0319]
[0320] [Group 2-5]
[0321]
[0322]
[0323] [Group 2-6]
[0324]
[0325]
[0326]
[0327]
[0328]
[0329]
[0330]
[0331]
[0332]
[0333] [Group 2-7]
[0334]
[0335] In one or more embodiments, based on the total weight of the emission assisting layer (100 wt%), the amount of the second dopant in the emission assisting layer may be about 20 weight percent (wt%) or less, about 19 wt% or less, about 18 wt% or less, about 17 wt% or less, about 16 wt% or less, about 15 wt% or less, about 14 wt% or less, about 13 wt% or less, about 12 wt% or less, about 11 wt% or less, or about 10 wt% or less.
[0336] In one or more embodiments, based on the total weight of the emission-assisting layer (100 wt%), the amount of the second dopant in the emission-assisting layer may be about 1 wt% to about 20 wt%, about 1 wt% to about 19 wt%, about 1 wt% to about 18 wt%, about 1 wt% to about 17 wt%, about 1 wt% to about 16 wt%, about 1 wt% to about 15 wt%, about 1 wt% to about 14 wt%, about 1 wt% to about 13 wt%, about 1 wt% to about 12 wt%, about 1 wt% to about 11 wt%, or about 1 wt% to about 10 wt%.
[0337] In one or more embodiments, the weight ratio of the second host to the second dopant in the emission-assisting layer may be about 1:19 to about 19:1, about 1:9 to about 9:1, about 2:8 to about 8:2, about 3:7 to about 7:3, or about 4:6 to about 6:4.
[0338] In one or more embodiments, the light emitting device may satisfy Equation 1:
[0339] Equation 1
[0340] E HOMO (D1)>E HOMO (D2)
[0341] Where, in equation 1,
[0342] E HOMO (D1) represents the highest occupied molecular orbital (HOMO) energy level of the first dopant,
[0343] E HOMO (D2) represents the HOMO level of the second dopant, and
[0344] The HOMO energy level (E HOMO (D1) and E HOMO (D2)) may each have a negative value measured in an ambient atmosphere by using a photoelectron spectroscopy device.
[0345] In one or more embodiments, the light emitting device may satisfy Equation 2:
[0346] Equation 2
[0347] E LUMO (D1)>E LUMO (D2)
[0348] Where, in equation 2,
[0349] E LUMO (D1) represents the lowest unoccupied molecular orbital (LUMO) energy level of the first dopant,
[0350] E LUMO (D2) represents the LUMO level of the second dopant, and
[0351] The LUMO energy levels may each have a negative value measured in an ambient atmosphere by using a photoelectron spectroscopy apparatus.
[0352] In one or more embodiments, the first electrode may be an anode, and the second electrode may be a cathode.
[0353] In one or more embodiments, the intermediate layer may further include a hole transport region disposed between the first electrode and the emission layer, and an electron transport region disposed between the emission layer and the second electrode.
[0354] In one or more embodiments, the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof.
[0355] In one or more embodiments, the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer, or a combination thereof.
[0356] In one or more embodiments, the emission layer may be in direct contact with the emission assisting layer.
[0357] In one or more embodiments, the emission-assisting layer may not emit light.
[0358] In one or more embodiments, the light emitting device may emit yellow-green light, green light, or blue-green light.
[0359] In some embodiments, the light emitting device can emit green light.
[0360] In one or more embodiments, the maximum peak wavelength (λ max ) may be from about 510 nm to about 570 nm, from about 520 nm to about 560 nm, from about 530 nm to about 550 nm, or from about 545 nm to about 555 nm.
[0361] The emission auxiliary layer included in the light emitting device may include a second dopant having a structure satisfying Formula 1, and more particularly, in Formula 1, R 1 , R 3 , or R 4 At least one of is not hydrogen.
[0362] Therefore, without wishing to be bound by theory, the light-emitting device as described herein may have a reduced driving voltage and improved efficiency due to increased hole injection from the emission-assisting layer to the emission layer, and the lifetime of the device may be increased due to suppression of deterioration of the interface between the emission-assisting layer and the emission layer by energy transfer from the emission-assisting layer to the emission layer.
[0363] As used herein, and unless otherwise defined, the term "OMe" is methoxy, "TMS" is trimethylsilyl, and "TMG" is trimethylgermyl.
[0364] The first host and the second host may each include a hole transport compound, an electron transport compound, a bipolar compound, or a combination thereof. The first host and the second host may each include no transition metal. The first host and the second host may be the same as or different from each other.
[0365] In one or more embodiments, the first host and the second host may each include a hole transport compound and an electron transport compound, and the hole transport compound and the electron transport compound may be different from each other.
[0366] In one or more embodiments, the hole transport compound may include at least one π-electron-rich C 3 -C 60 The cyclic group may not include an electron transporting group. Non-limiting examples of the electron transporting group may include a cyano group, a fluorine group (—F), a cyclic group containing π-electron-deficient nitrogen, a phosphine oxide group, a sulfoxide group, and the like.
[0367] As used herein, the "ring group containing π-electron-deficient nitrogen" may be a C-N-containing ring group having at least one *-N=*' moiety as a ring-forming part. 1 -C 60 Heterocyclic group. Non-limiting examples of the ring group containing π-electron-deficient nitrogen may include a triazine group, an imidazole group, and the like.
[0368] As used herein, “π-electron-rich C 3 -C 60 The "cyclic group" may be a C- 3 -C 60 Ring group. π-electron-rich C 3 -C 60 Non-limiting examples of the cyclic group may include a benzene group, a naphthyl group, a benzo[9,10]phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an indoledibenzofuran group, an indoledibenzothiophene group, an indolecarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a phenanthrobenzofuran group, a phenanthrobenzothiophene group, a naphthocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, a dibenzocarbazole group, and the like.
[0369] For example, the hole transport compound may include two or more carbazole groups.
[0370] In one or more embodiments, the electron transport compound may be a compound including at least one electron transport group. The electron transport group may be a cyano group, a fluorine group (-F), a C 1 -C 60A cyclic group, a phosphine oxide group, a sulfoxide group, or a combination thereof. In one or more embodiments, the electron transport compound may include a triazine group.
[0371] For example, the electron transport compound may include at least one electron transport group (eg, a triazine group, etc.) and at least one π-electron-rich C 3 -C 60 Cyclic groups (for example, a benzene group, a naphthyl group, a benzo[9,10]phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an indoledibenzofuran group, an indoledibenzothiophene group, an indolecarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a phenanthrobenzofuran group, a phenanthrobenzothiophene group, a naphthocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, a dibenzocarbazole group, the like, or a combination thereof).
[0372] In one or more embodiments, the hole transport compound may be a compound represented by Formula 6:
[0373] Formula 6
[0374]
[0375] Among them, in formula 6,
[0376] L 61 and L 62 Each independently may be unsubstituted or substituted with at least one of the following π-electron-rich C 3 -C 60 Ring groups: deuterium, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, (C 1 -C 20 Alkyl)biphenyl, -Si(Q 33 )(Q 34 )(Q 35 ), or a combination thereof,
[0377] e61 and e62 can each independently be an integer of 1-6,
[0378] R 61 -R 64 Can be independently:
[0379] Hydrogen, deuterium, C 1 -C 20 Alkyl, or deuterated C 1 -C20 alkyl;
[0380] unsubstituted or substituted with at least one of the following π-electron-rich C 3 -C 60 Ring groups: deuterium, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, (C 1 -C 20 Alkyl)biphenyl, -Si(Q 33 )(Q 34 )(Q 35 ), or a combination thereof; or
[0381] -Si(Q 3 )(Q 4 )(Q 5 ),and
[0382] a63 and a64 may each independently be an integer of 0-7.
[0383] Q 3 -Q 5 and Q 33 -Q 35 Each may be as described herein.
[0384] In one or more embodiments, the hole transport compound may be a compound represented by at least one of Formula 6-1, 6-2, or 6-3:
[0385] Formula 6-1
[0386]
[0387] Formula 6-2
[0388]
[0389] Formula 6-3
[0390]
[0391] Among them, in formulas 6-1 to 6-3, L 61 , L 62 , R 61 -R 64 , e61, e62, a63, and a64 are respectively as described herein.
[0392] In one or more embodiments, the hole transport compound may be at least one of compounds H-HT1 to H-HT5 and HT(1):
[0393]
[0394] In one or more embodiments, the electron transport compound may be a compound represented by Formula 7:
[0395] Formula 7
[0396]
[0397] Among them, in formula 7,
[0398] X 74 Can be C(R 74 ) or N, X 75 Can be C(R 75 ) or N, X 76 Can be C(R 76 ) or N, and X 74 -X 76 At least one of may be N,
[0399] L 71 -L 73 may be each independently unsubstituted or substituted by at least one of the following C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups: deuterium, -F, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorophenyl, (C 1 -C 20 Alkyl)biphenyl, -Si(Q 33 )(Q 34 )(Q 35 ), or a combination thereof, e71-e73 may each independently be an integer of 1-10, and
[0400] R 71 -R 76 Can be independently:
[0401] hydrogen, deuterium, -F, or cyano;
[0402] C is unsubstituted or substituted with at least one of the following 1 -C 20 Alkyl: deuterium, -F, cyano, or a combination thereof;
[0403] C each unsubstituted or substituted with at least one of the following 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups: deuterium, -F, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorophenyl, (C 1 -C 20 Alkyl)biphenyl, -Si(Q 33 )(Q 34 )(Q 35 ), or a combination thereof; or
[0404] -Si(Q 3 )(Q 4 )(Q 5 ).
[0405] Q 3 -Q 5 and Q 33 -Q 35 Each may be as described herein.
[0406] In one or more embodiments, X in Formula 7 74 -X 76 Each can be N.
[0407] In one or more embodiments, L in Formula 7 71 -L 73 and phenyl groups, naphthalene groups, benzo[9,10]phenanthrene groups, dibenzofuran groups, dibenzothiophene groups, carbazole groups, indoledibenzofuran groups, indoledibenzothiophene groups, indolecarbazole groups, naphthobenzofuran groups, naphthobenzothiophene groups, benzocarbazole groups, phenanthrobenzofuran groups, phenanthrobenzothiophene groups, naphthocarbazole groups, dinaphthofuran groups, dinaphthothiophene groups, or dibenzocarbazole groups, each of which is unsubstituted or substituted by at least one of the following: deuterium, -F, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C20 Alkyl, fluorinated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorophenyl, (C 1 -C 20 Alkyl)biphenyl, -Si(Q 33 )(Q 34 )(Q 35 ), or a combination thereof.
[0408] In one or more embodiments, in Formula 7, the number of L is e71 71 At least one L with a quantity of e72 72 At least one L with a quantity of e73 73 At least one of the above, or a combination thereof, may be each independently a dibenzofuran group, a dibenzothiophene group, a carbazole group, an indole dibenzofuran group, an indole dibenzothiophene group, an indole carbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a phenanthrobenzofuran group, a phenanthrobenzothiophene group, a naphthocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, or a dibenzocarbazole group, each of which is unsubstituted or substituted with at least one of the following: deuterium, -F, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorophenyl, (C 1 -C 20 Alkyl)biphenyl, -Si(Q 33 )(Q 34 )(Q 35 ), or a combination thereof.
[0409] In one or more embodiments, in Formula 7, the number of L is e71 71 At least one L with a quantity of e72 72 At least one L with a quantity of e73 73 At least one of or a combination thereof may include a carbazole group, an indolecarbazole group, a benzocarbazole group, a naphthoxycarbazole group, or a dibenzocarbazole group, and the nitrogen atom of the pyrrole group of the carbazole group, the indolecarbazole group, the benzocarbazole group, the naphthoxycarbazole group, or the dibenzocarbazole group may be connected to the group including X in Formula 7. 74 -X76 The carbon atom of the 6-membered ring, and the single bond or adjacent L 71 , L 72 , and / or L 73 In between.
[0410] In one or more embodiments, e71-e73 in Formula 7 represent L 71 -L 73 , and may each independently be 1, 2, 3, 4, or 5.
[0411] In one or more embodiments, R in Formula 7 71 -R 76 Can be independently:
[0412] hydrogen, deuterium, -F, or cyano;
[0413] C is unsubstituted or substituted with at least one of the following 1 -C 20 Alkyl: deuterium, -F, cyano, or a combination thereof;
[0414] a phenyl group, a naphthyl group, a benzo[9,10]phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an indoledibenzofuran group, an indoledibenzothiophene group, an indolecarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a phenanthrobenzofuran group, a phenanthrobenzothiophene group, a naphthocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, or a dibenzocarbazole group, each of which is unsubstituted or substituted with at least one of the following: deuterium, -F, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorophenyl, (C 1 -C 20 Alkyl)biphenyl, -Si(Q 33 )(Q 34 )(Q 35 ), or a combination thereof; or
[0415] -Si(Q 3 )(Q 4 )(Q 5 ).
[0416] In one or more embodiments, the electron transport compound may be at least one of compounds H-ET1 to H-ET6:
[0417]
[0418] In one or more embodiments, each of the first emission layer and the second emission layer may not include the compound of [Group A]:
[0419] [Group A]
[0420]
[0421]
[0422]
[0423] In one or more embodiments, the intermediate layer of the light emitting device may further include a hole transport region disposed between the first electrode and the emission layer, and an electron transport region disposed between the emission layer and the second electrode.
[0424] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
[0425] The term "intermediate layer" as used herein refers to a single layer or a plurality of layers disposed between a first electrode and a second electrode of a light emitting device. The "intermediate layer" may include not only an organic compound but also an organic metal complex including a metal.
[0426] According to another aspect, the light emitting device may be included in an electronic device. Therefore, an electronic device including the light emitting device is provided. The electronic device may include, for example, a display, a lighting device, a sensor, etc., but the embodiment is not limited thereto.
[0427] Description of the drawings
[0428] Figure 1 A cross-sectional view of an organic light emitting device 100 as a light emitting device according to one or more embodiments is schematically illustrated. Figure 1 The structure and the manufacturing method of the organic light emitting device 100 according to one or more embodiments are described, but the embodiments are not limited thereto.
[0429] Figure 1 The organic light-emitting device 100 may include a first electrode 110, a second electrode 190, and an intermediate layer (not shown) arranged between the first electrode 110 and the second electrode 190, wherein the intermediate layer may include a hole transport region 120, an emission auxiliary layer 130, an emission layer 150, and an electron transport region 170, which are stacked in the order stated.
[0430] A substrate may be additionally disposed under the first electrode 110 or over the second electrode 190. The substrate may be a conventional substrate used in an organic light-emitting device, for example, a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, easy handling (processing), and / or waterproofness.
[0431] The first electrode 110 may be formed by providing a material for forming the first electrode 110 on the substrate by using a deposition or sputtering method. The first electrode 110 may be an anode. The material for forming the first electrode 110 may include a material having a high work function to facilitate hole injection. The first electrode 110 may be a reflective electrode. The material for forming the first electrode 110 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), or zinc oxide (ZnO). In one or more embodiments, the material used to form the first electrode 110 may be a metal such as magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).
[0432] 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 triple-layer structure of ITO / Ag / ITO.
[0433] The hole transport region 120 may be disposed between the first electrode 110 and the emission layer 150 , and more specifically, between the first electrode 110 and the emission auxiliary layer 130 .
[0434] The hole transport region 120 may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof.
[0435] The hole transport region 120 may include only a hole injection layer or only a hole transport layer. In one or more embodiments, the hole transport region 120 may have a hole injection layer / hole transport layer structure or a hole injection layer / hole transport layer / electron blocking layer structure, which are sequentially stacked in the stated order starting from the first electrode 110.
[0436] When the hole transport region 120 includes a hole injection layer, the hole injection layer may be formed on the first electrode 110 by using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, etc., or a combination thereof.
[0437] When the hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on the material used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a ... -8 To about 10 -3 Torr vacuum pressure, and approx. to about of deposition rate.
[0438] When the hole injection layer is formed by spin coating, the coating conditions may vary depending on the material used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the coating conditions may include a coating speed of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and a heat treatment temperature of about 80° C. to about 200° C. for removing the solvent after coating.
[0439] Conditions for forming the hole transport layer and the electron blocking layer may be the same as or similar to conditions for forming the hole injection layer.
[0440] The hole transport region 120 may include at least one of 4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4′,4″-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB), β-NPB, N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD), spiro-TPD, spiro-NPB, methylated NPB, 4,4′- Cyclohexylidenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4′-bis[N,N′-(3-methylphenyl)amino]-3,3′-dimethylbiphenyl (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, a compound represented by Formula 202, or a combination thereof, but the embodiment is not limited thereto:
[0441]
[0442] Formula 201
[0443]
[0444] Formula 202
[0445]
[0446] In formula 201, Ar 101 and Ar 102 Each of the following may be independently unsubstituted or substituted by at least one of the following: phenylene, pentalene, indenylene, naphthylene, azulenylene, heptalene, acenaphthene, fluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenyl ...enylene, benzo[ phenylene, tetraphenylene, perylene, or pentphenylene: deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 7 -C 60 Arylalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroarylalkyl, C 1 -C 60 Heteroaryloxy, C 1 -C 60a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or a combination thereof.
[0447] In Formula 201, xa and xb may each independently be an integer of 0-5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0.
[0448] R in formula 201 and 202 101 -R 108 , R 111 -R 119 and R 121 -R 124 Can be independently:
[0449] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 10 Alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), C 1 -C 10 Alkoxy (e.g., methoxy, ethoxy, propoxy, butoxy, pentyloxy, etc.), or C 1 -C 10 Alkylthio;
[0450] C each unsubstituted or substituted with at least one of the following 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, or C 1 -C 10 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, or a combination thereof; or
[0451] Phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl, each unsubstituted or substituted with at least one of the following: deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, C 1 -C 10 alkylthio, or a combination thereof.
[0452] In formula 201, R109 It can be phenyl, naphthyl, anthracenyl, or pyridyl, each of which is unsubstituted or substituted by at least one of the following: deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 1 -C 20 alkylthio, phenyl, naphthyl, anthracenyl, pyridyl, or a combination thereof.
[0453] In one embodiment, the compound represented by Formula 201 can be represented by Formula 201A:
[0454] Formula 201A
[0455]
[0456] R in Formula 201A 101 , R 111 , R 112 , and R 109 Each is as described herein.
[0457] For example, the hole transport region 120 may include at least one of compounds HT1 to HT20, or a combination thereof, but the embodiment is not limited thereto:
[0458]
[0459]
[0460] The thickness of the hole transport region 120 may be about to about For example, about to about When the hole transport region 120 includes a hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof, the thickness of the hole injection layer may be about to about For example, about to about And the thickness of the hole transport layer may be about to about For example, about to about Without wishing to be bound by theory, when the thicknesses of the hole transport region 120, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics may be obtained without a significant increase in driving voltage.
[0461] In addition to the materials described above, the hole transport region 120 may further include a charge generation material to improve conductivity. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region.
[0462] The charge generating material may be, for example, a p-dopant. The p-dopant may be a quinone derivative, a metal oxide, a compound containing a cyano group, or a combination thereof. For example, the p-dopant may include a quinone derivative such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ), or 1,3,4,5,7,8-hexafluorotetracyanonaphthoquinodimethane (F6-TCNNQ); a metal oxide such as tungsten oxide, molybdenum oxide, etc.; a compound containing a cyano group such as compound HT-D1; or a combination thereof, but the embodiment is not limited thereto.
[0463]
[0464] The hole transport region 120 may further include a buffer layer.
[0465] Furthermore, the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of the formed organic light emitting device may be improved.
[0466] Meanwhile, when the hole transport region 120 includes an electron blocking layer, the material for the electron blocking layer may include the material that can be used in the hole transport region 120 as described above, a host material, or a combination thereof. For example, when the hole transport region includes an electron blocking layer, mCP, compound HT (1), etc. may be used as the material for the electron blocking layer:
[0467]
[0468] The emission auxiliary layer 130 and the emission layer 150 may be sequentially formed on the hole transport region 120 by using, for example, a vacuum deposition method, a spin coating method, a casting method, an LB method, an inkjet printing method, etc., but the embodiment is not limited thereto. When the emission auxiliary layer 130 or the emission layer 150 is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied when forming the hole injection layer, although the deposition or coating conditions may vary depending on the material used to form the emission auxiliary layer 130 or the emission layer 150.
[0469] The thickness of the emission auxiliary layer 130 may be about to about For example to about
[0470] The thickness of the emission layer 150 may be about to about For example to about Without wishing to be bound by theory, when the thickness of the emission layer 150 is within these ranges, excellent light emitting characteristics may be obtained without a significant increase in driving voltage.
[0471] A ratio of the thickness of the emission-assisting layer to the thickness of the emission layer may be about 8:2 to about 2:8, about 7:3 to about 3:7, or about 6:4 to about 4:6.
[0472] When the light emitting device is a full-color light emitting device, the emission layer 150 may be patterned into a red emission layer, a green emission layer, and / or a blue emission layer.
[0473] Next, the electron transport region 170 may be disposed on the emission layer 150 .
[0474] The electron transport region 170 may include a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer, or a combination thereof.
[0475] For example, the electron transport region 170 may have a hole blocking layer / electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer structure, or an electron transport layer / electron injection layer structure. The electron transport layer may have a multilayer structure or a single layer structure including two or more different materials.
[0476] The conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer in the electron transport region 170 are the same as the conditions for forming the hole injection layer.
[0477] When the electron transport region 170 includes a hole blocking layer, the hole blocking layer may include, for example, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), bis(2-methyl-8-hydroxyquinoline-N1,08)-(1,1′-biphenyl-4-hydroxy)aluminum (BAlq), or a combination thereof, but the embodiment is not limited thereto:
[0478]
[0479] In one or more embodiments, the hole blocking layer may include any suitable host material or a material for an electron transport layer, a material for an electron injection layer, or a combination thereof, which will be described later.
[0480] The thickness of the hole blocking layer may be about to about For example to about Without wishing to be bound by theory, when the thickness of the hole blocking layer is within these ranges, excellent hole blocking characteristics may be obtained without a significant increase in driving voltage.
[0481] The electron transport layer may include at least one of the following: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), tris(8-hydroxy-quinoline)aluminum (Alq 3 ), bis(2-methyl-8-hydroxyquinoline-N1,08)-(1,1′-biphenyl-4-hydroxy)aluminum (BAlq), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), or a combination thereof, but the embodiments are not limited thereto:
[0482]
[0483] In one or more embodiments, the electron transport layer may include at least one of compounds ET1 to ET25, or a combination thereof, but the embodiments are not limited thereto:
[0484]
[0485]
[0486] The thickness of the electron transport layer may be about to about For example to about Without wishing to be bound by theory, 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 a significant increase in driving voltage.
[0487] The electron transport layer may include a material containing a metal in addition to the materials described above.
[0488] The metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 or ET-D2, but embodiments are not limited thereto:
[0489]
[0490] In one or more embodiments, the electron transport region 170 may include an electron injection layer that facilitates injection of electrons from the second electrode 190 .
[0491] The electron injection layer may include LiF, NaCl, CsF, Li 2 O, BaO, Yb, compound ET-D1, compound ET-D2, or a combination thereof.
[0492] The thickness of the electron injection layer may be about to about or for example to about Without wishing to be bound by theory, when the thickness of the electron injection layer is within the above-described range, satisfactory electron injection characteristics may be obtained without a significant increase in driving voltage.
[0493] The second electrode 190 may be arranged on the electron transport region 170. The second electrode 190 may be a cathode. The material used to form the second electrode 190 may be a metal, an alloy, a conductive compound, or a combination thereof having a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. may be used as materials for forming the second electrode 190. In one or more embodiments, in order to manufacture a top-emitting light-emitting device, a transparent or translucent electrode formed using ITO or IZO may be used as the second electrode 190.
[0494] As used herein, the term "C 1 -C 60 "Alkyl" refers to a straight chain or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and as used herein, the term "C 1 -C 60 "Alkylene" refers to a group having a C 1 -C 60 Alkyl is a divalent group of the same structure.
[0495] C 1 -C 60 Alkyl, C 1 -C 20 Alkyl, and / or C 1 -C 10Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-dec ... Decyl, secondary decyl, tert-decyl, etc.: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, tert-decyl, etc., or a combination thereof. For example, Formula 9-33 is a branched C 6 Alkyl, for example, tert-butyl substituted with two methyl groups.
[0496] As used herein, the term "C 1 -C 60 "Alkoxy" refers to a 101 (A 101 C 1 -C 60 The term "alkyl" refers to a monovalent group represented by an alkyl group, and non-limiting examples thereof include methoxy, ethoxy, propoxy, butoxy, pentyloxy, and the like.
[0497] As used herein, the term "C 2 -C 60 "Alkenyl" refers to a group consisting of 2 -C 60 The term "C" as used herein refers to a hydrocarbon group formed by inserting at least one carbon-carbon double bond in the middle or at the terminal of an alkyl group, and non-limiting examples thereof include vinyl, propenyl, butenyl, etc. 2 -C 60 "Alkenylene" refers to a 2 -C 60 Alkenyl is a divalent group of the same structure.
[0498] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a 2 -C 60 The term "C" as used herein refers to a hydrocarbon group formed by inserting at least one carbon-carbon triple bond in the middle or at the terminal of an alkyl group, and non-limiting examples thereof include ethynyl, propynyl, and the like. 2 -C 60 "Alkyne" refers to a group having a C 2 -C60 Alkynyl is a divalent group of the same structure.
[0499] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and C 3 -C 10 Cycloalkylene is a cycloalkylene having 3 -C 10 Cycloalkyl is a divalent group of the same structure.
[0500] C 3 -C 10 Non-limiting examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, and the like.
[0501] As used herein, the term "C 1 -C 10 "Heterocycloalkyl" refers to a monovalent saturated ring group including at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring atom and 1 to 10 carbon atoms as ring atoms, and the term "C 1 -C 10 "Heterocycloalkylene" refers to a 1 -C 10 Heterocycloalkyl is a divalent group of the same structure.
[0502] C 1 -C 10 Non-limiting examples of heterocycloalkyl include silacyclopentyl, silacyclohexyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, tetrahydrothienyl, and the like.
[0503] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent hydrocarbon ring group having 3 to 10 carbon atoms as ring atoms and at least one carbon-carbon double bond in its ring and not having aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, cycloheptenyl, etc. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to a 3 -C 10 Cycloalkenyl is a divalent group of the same structure.
[0504] As used herein, the term "C 1 -C 10The term "heterocycloalkenyl" refers to a monovalent cyclic group having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring atom, 1 to 10 carbon atoms as ring atoms, and at least one double bond in its ring. 1 -C 10 Non-limiting examples of heterocycloalkenyl include 2,3-dihydrofuranyl, 2,3-dihydrothienyl, and the like. As used herein, the term “C 1 -C 10 "Heterocycloalkenylene" refers to a 1 -C 10 Heterocycloalkenyl is a divalent group of the same structure.
[0505] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic ring system having 6 to 60 carbon atoms, and as used herein, the term "C 6 -C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic ring system having 6 to 60 carbon atoms. 6 -C 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, Ji et al. 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the rings may be fused to each other.
[0506] As used herein, the term "C 7 -C 60 "Alkylaryl" refers to a 1 -C 54 Alkyl substituted C 6 -C 59 Aryl. As used herein, the term "C 7 -C 60 "Arylalkyl" refers to a 6 -C 59 Aryl substituted C 1 -C 54 alkyl.
[0507] As used herein, the term "C 1 -C 60 The term “heteroaryl” refers to a monovalent aromatic ring group including a cyclic aromatic ring system having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring atom and 1 to 60 carbon atoms as ring atoms, and the term “C 1 -C60 The term "heteroarylene" refers to a divalent group including a cyclic aromatic ring system having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring atom and 1 to 60 carbon atoms as ring atoms. 1 -C 60 Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, and the like. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include two or more rings, the rings may be fused to each other.
[0508] As used herein, the term "C 2 -C 60 "Alkylheteroaryl" refers to a 1 -C 59 Alkyl substituted C 1 -C 59 As used herein, the term "C 2 -C 60 "Heteroarylalkyl" refers to a 1 -C 59 Heteroaryl-substituted C 1 -C 59 alkyl.
[0509] As used herein, the term "C 6 -C 60 "Aryloxy" means -OA 102 (A 102 Represents C 6 -C 60 Aryl), as used herein, 6 -C 60 "Arylthio" means -SA 103 (A 103 Represents C 6 -C 60 aryl), and as used herein, the term "C 1 -C 60 "Alkylthio" means -SA 104 (A 104 Represents C 1 -C 60 alkyl).
[0510] As used herein, the term "C 1 -C 60 "Heteroaryloxy" means -OA 102 (A 102 Represents C 1-C 60 Heteroaryl), and as used herein, the term "C 1 -C 60 "Heteroarylthio" means -SA 103 (A 103 Represents C 1 -C 60 heteroaryl).
[0511] The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group (e.g., having 8-60 carbon atoms) that has two or more rings fused to each other, has only carbon atoms as ring-forming atoms, and does not have aromaticity in its entire molecular structure. Non-limiting examples of monovalent non-aromatic fused polycyclic groups include fluorenyl and the like. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group described above.
[0512] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (e.g., having 1 to 60 carbon atoms) having two or more rings fused to each other, having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom in addition to carbon atoms, and having no aromaticity in its entire molecular structure. Non-limiting examples of monovalent non-aromatic fused heteropolycyclic groups include carbazolyl and the like. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic group described above.
[0513] As used herein, the term "C 5 -C 30 The term "carbocyclic group" refers to a saturated or unsaturated ring group having only 5 to 30 carbon atoms as ring atoms. 5 -C 30 The carbocyclic group may be a monocyclic group or a polycyclic group. As used herein, "(unsubstituted or replaced by at least one R 10a Replaced by)C 5 -C 30 Non-limiting examples of "carbocyclic group" may include (each unsubstituted or substituted with at least one R 10a substituted) adamantane group, norbornene group, bicyclo[1.1.1]pentane group, bicyclo[2.1.1]hexane group, bicyclo[2.2.1]heptane (norbornane) group, bicyclo[2.2.2]octane group, cyclopentane group, cyclohexane group, cyclohexene group, phenyl group, naphthalene group, anthracene group, phenanthrene group, benzo[9,10]phenanthrene group, pyrene group, group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, or a fluorene group.
[0514] As used herein, the term "C 1 -C 30 The term "heterocyclic group" refers to a saturated or unsaturated ring group having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring atom in addition to 1 to 30 carbon atoms as ring atoms. 1 -C 30 The heterocyclic group may be a monocyclic group or a polycyclic group. As used herein, "(unsubstituted or replaced by at least one R 10a Replaced by)C 1 -C 30 Non-limiting examples of "heterocyclic group" may include (each unsubstituted or substituted by at least one R 10a substituted) thiophene group, furan group, pyrrole group, thiol group, borolide group, phospholide group, selenophene group, germanol group, benzothiophene group, benzofuran group, indole group, benzothiol group, benzoborol group, benzophospholide group, benzoselenophene group, benzogermanol group, dibenzothiophene group, dibenzofuran group, carbazole group, dibenzothiol group, dibenzoborol group, group, dibenzophosphoside group, dibenzoselenophene group, dibenzogermanoside group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzothiorrole group, azabenzoborole group, azabenzophosphoside group, azabenzoselenophene group, azabenzogermanoside group , azadibenzothiophene group, azadibenzofuran group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzoborole group, azadibenzophosphole group, azadibenzoselenophene group, azadibenzogermanol group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group A group comprising: a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzooxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
[0515] As used in this article, “C 5 -C 30Carbocyclic group" and "C 1 -C 30 Examples of the "heterocyclic group" may include i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed to each other, iv) a condensed ring in which two or more second rings are condensed to each other, or v) a condensed ring in which at least one first ring is condensed to at least one second ring,
[0516] wherein the first ring can be a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a thiorrole group, a borocyclopentadiene group, a phosphole group, a germanocyclopentadiene group, a selenophene group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, or an azathiorrole group, and
[0517] The second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
[0518] As used herein, "fluorinated C 1 -C 60 Alkyl (or fluorinated C 1 -C 20 Alkyl, etc.)", "Fluorinated C 3 -C 10 Cycloalkyl", "fluoro-C 1 -C 10 "Heterocycloalkyl" and "fluorophenyl" may be C 1 -C 60 Alkyl (or C 1 -C 20 Alkyl, etc.), C 3 -C 10 Cycloalkyl, C 1 -C 10 For example, as used herein, the term "fluoro-C 1 Alkyl (i.e., fluoromethyl)" includes -CF 3 , -CF 2 H, and -CFH 2 As used herein, the term "fluoro-C 1 -C 60 Alkyl (or fluorinated C 1 -C 20 Alkyl, etc.)", "Fluorinated C 3 -C 10 Cycloalkyl", "fluoro-C 1 -C 10"Heterocycloalkyl" and "fluorophenyl" respectively refer to i) a fully fluorinated C 1 -C 60 Alkyl (or fully fluorinated C 1 -C 20 alkyl, etc.), fully fluorinated C 3 -C 10 Cycloalkyl, fully fluorinated C 1 -C 10 1) a fluorinated phenyl radical, wherein all hydrogen atoms in each radical are replaced by fluorinated radicals, or 2) a partially fluorinated C 1 -C 60 Alkyl (or partially fluorinated C 1 -C 20 alkyl, etc.), partially fluorinated C 3 -C 10 Cycloalkyl, partially fluorinated C 1 -C 10 Heterocycloalkyl, or partially fluorinated phenyl, wherein not all hydrogen atoms included in each group are replaced by fluorine groups.
[0519] As used herein, "deuterated C 1 -C 60 Alkyl (or deuterated C 1 -C 20 Alkyl, etc.)", "deuterated C 3 -C 10 Cycloalkyl", "deuterated C 1 -C 10 "Heterocycloalkyl" and "deuterated phenyl" may be C 1 -C 60 Alkyl (or C 1 -C 20 Alkyl, etc.), C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, and phenyl. 1 Non-limiting examples of "alkyl (i.e., deuterated methyl)" may include -CD 3 、-CD 2 H, and -CDH 2 . "Deuterated C 3 -C 10 Examples of "cycloalkyl" may include Formula 10-501. As used herein, the term "deuterated C 1 -C 60 Alkyl (or deuterated C 1 -C 20 Alkyl, etc.)", "deuterated C 3 -C 10Cycloalkyl", "deuterated C 1 -C 10 "heterocycloalkyl" and "deuterated phenyl" refer to i) a fully deuterated C 1 -C 60 Alkyl (or fully deuterated C 1 -C 20 alkyl, etc.), fully deuterated C 3 -C 10 Cycloalkyl, fully deuterated C 1 -C 10 1) a partially deuterated phenyl radical; 2) a partially deuterated phenyl radical; 3) a fully deuterated phenyl radical; 4) a fully deuterated phenyl radical; 5) a fully deuterated phenyl radical; 6) a fully deuterated phenyl radical; 7) a fully deuterated phenyl radical; 8) a fully deuterated phenyl radical; 1 -C 60 Alkyl (or partially deuterated C 1 -C 20 alkyl, etc.), partially deuterated C 3 -C 10 Cycloalkyl, partially deuterated C 1 -C 10 Heterocycloalkyl, or partially deuterated phenyl, wherein not all hydrogen atoms included in each group are replaced by deuterium.
[0520] As used herein, the term "(C 1 -C 20 Alkyl)'X' group" refers to a 1 -C 20 Alkyl substituted 'X' group. For example, as used herein, the term "(C 1 -C 20 Alkyl)C 3 -C 10 "Cycloalkyl" refers to a cycloalkyl group consisting of at least one C 1 -C 20 Alkyl substituted C 3 -C 10 For example, as used herein, the term "(C 1 -C 20 "Alkyl)phenyl" refers to a 1 -C 20 Alkyl substituted phenyl. (C 1 An example of an alkyl)phenyl group is tolyl.
[0521] The term “azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, azabenzosilole group, azabenzogermanol group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborole group, azadibenzophosphole group, azafluorene group, azadibenzosilole group, azadibenzogermanol group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, and azadibenzothiophene group, and 5,5-dioxide group” They respectively refer to the following heterocyclic groups: they have the same skeleton as “indole group, benzoborole group, benzophosphole group, indene group, benzosilole group, benzogermanol group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, dibenzosilole group, dibenzogermanol group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene group, and 5,5-dioxide group”, wherein, in each group, at least one carbon selected from the ring-forming carbons is replaced by nitrogen.
[0522] Substituted C 5 -C 30 Carbocyclic groups, substituted C 1 -C 30 Heterocyclic groups, 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 1 -C 60 Alkylthio, 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 7 -C 60 Alkyl aryl, substituted C 7 -C60 Arylalkyl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 Alkyl heteroaryl, substituted C 2 -C 60 Heteroarylalkyl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 The substituent of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:
[0523] Deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio;
[0524] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, 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 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-Ge(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(=O)(Q 18 )(Q 19 )、-P(Q 18 )(Q 19 ), or a combination thereof;
[0525] C each unsubstituted or substituted with at least one of the following 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 7 -C 60 Alkyl aryl, C6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, 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 7 -C 60 Alkyl aryl, C 7 -C 60 Arylalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 2 -C 60 Heteroarylalkyl, C 1 -C 60Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-Ge(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(=O)(Q 28 )(Q 29 )、-P(Q 28 )(Q 29 ), or a combination thereof;
[0526] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-Ge(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39 ), or -P(Q 38 )(Q 39 );or
[0527] Its combination.
[0528] As used in this article, Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 Can be independently:
[0529] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C60 Alkynyl, 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 7 -C 60 Alkyl aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group. 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 may be each independently unsubstituted or substituted by at least one of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 1 -C 10Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 7 -C 60 Arylalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 2 -C 60 Heteroarylalkyl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio group, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, C 1 -C 60 Alkyl, C 6 -C 60 aryl, or a combination thereof.
[0530] For example, as described in this article, Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 and Q 31 -Q 39 Can be independently:
[0531] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD3 、-CD 2 CD 2 H, or -CD 2 CDH 2 ;or
[0532] n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl, each unsubstituted or substituted with at least one of the following: deuterium, C 1 -C 10 Alkyl, phenyl, or a combination thereof.
[0533] Hereinafter, the light emitting device according to the exemplary embodiment is described in further detail with reference to examples. However, the embodiment is not limited to the following examples.
[0534] Example
[0535] Evaluation Example 1
[0536] The HOMO levels of Compound Pt-1 and Compound Ir-1 had negative values measured in an ambient atmosphere by using a photoelectron spectroscopy apparatus (AC-3 manufactured by RIKENKEIKI Co., Ltd.), and the results are shown in Table 1.
[0537] Pt-1
[0538]
[0539] Ir-1
[0540]
[0541] Table 1
[0542]
[0543] Fabrication of OLED of Example 1
[0544] ITO / Ag / ITO (as anode) is deposited on it. A glass substrate with a thickness of 50 mm × 50 mm × 0.5 mm was cut into a size of 50 mm × 50 mm × 0.5 mm, ultrasonically treated with isopropyl alcohol and deionized (DI) water for 5 minutes each, and then cleaned by irradiating ultraviolet rays and exposing it to ozone for 30 minutes. Then, the resulting glass substrate was loaded onto a vacuum deposition device.
[0545] HT3 and F6-TCNNQ were vacuum co-deposited on the anode in a weight ratio of 98:2 to form a hole injection layer (HIL) having a thickness of 10 nanometers (nm), HT3 was vacuum deposited on the hole injection layer to form a hole transport layer (HTL) having a thickness of 140 nm, and HT(1) was vacuum deposited on the hole transport layer to form an electron blocking layer (EBL) having a thickness of 30 nm.
[0546] Then, a dopant (Pt-1) and H-H1 and H-H2 (weight ratio: 50:50, H-H1 is H-HT2 mentioned above, and H-H2 is H-ET6 mentioned above) as a host are vacuum co-deposited on the electron blocking layer to form an emission auxiliary layer having a thickness of 10 nm. Based on 100 parts by weight of the emission auxiliary layer, the amount of the dopant in the emission auxiliary layer is 5 parts by weight.
[0547] The dopant (Ir-1) and H-H1 and H-H2 as the main body (weight ratio: 50:50) were vacuum co-deposited on the emission auxiliary layer to form an emission layer with a thickness of 30 nm. The amount of the dopant in the emission layer was 7 parts by weight based on 100 parts by weight of the emission layer.
[0548] Afterwards, ET3 was vacuum deposited on the emission layer to form a hole blocking layer (HBL) having a thickness of 5 nm, ET3 and ET-D1 were vacuum co-deposited on the HBL at a weight ratio of 50:50 to form an electron transport layer (ETL) having a thickness of 31 nm, Mg and Ag were co-deposited on the ETL at a weight ratio of 10:90 to form a cathode having a thickness of 12 nm, and HT3 was vacuum deposited on the cathode to form a capping layer (CPL) having a thickness of 8 nm, thereby completing the manufacture of the light-emitting device of Example 1.
[0549]
[0550] Fabrication of OLED of Example 2
[0551] The OLED of Example 2 was manufactured in a similar manner to that of Example 1, except that when forming the emission auxiliary layer, HT(1) was used as a host instead of H-H1 and H-H2 (weight ratio: 50:50).
[0552] Preparation of OLED of Comparative Example 1
[0553] The OLED of Comparative Example 1 was manufactured in a similar manner to that of Example 1, except that no dopant was used when forming the emission auxiliary layer.
[0554] Preparation of OLED of Comparative Example 2
[0555] The OLED of Comparative Example 2 was manufactured in a similar manner to that of Example 2, except that no dopant was used when forming the emission auxiliary layer.
[0556] Preparation of OLED of Comparative Example 3
[0557] The OLED of Comparative Example 3 was manufactured in a similar manner as in Example 1, except as follows:
[0558] When forming the emission auxiliary layer, use As a dopant, and when forming an emission layer, using As a dopant.
[0559] Evaluation Example 2
[0560] The driving voltage (V, volt), luminous efficiency (%), lifespan (relative %), CIE color coordinates (CIEx / CIEy), and roll-off ratio (%) of the OLEDs of Example 1, Example 2, and Comparative Examples 1 to 3 were evaluated, and the results are shown in Table 1. A Keithley 2400 current-voltage meter and a brightness meter (Tocon SR3) were used in the evaluation. The lifespan (at 8,000 nits) was evaluated by measuring the time taken for the brightness to decrease from the initial brightness (100%) to 97% thereof, and calculating the roll-off ratio according to Equation 20:
[0561] Equation 20
[0562] Roll-off ratio = {1-(luminous efficiency (at 15,000 nits) / maximum luminous efficiency)}×100%
[0563] As for the luminous efficiency and the lifespan, they are shown as relative values.
[0564] Table 2
[0565]
[0566] As confirmed by Table 1, the organic light-emitting devices of Examples 1 and 2 simultaneously have low driving voltage, low roll-off ratio, improved luminous efficiency, and increased lifespan, which indicates that the organic light-emitting devices of Examples 1 and 2 have improved overall performance, especially significantly improved lifespan characteristics.
[0567] Since the light emitting device has excellent driving voltage, roll-off ratio, luminous efficiency, and lifespan characteristics, high-quality electronic devices can be manufactured by using the light emitting device.
[0568] It should be understood that the exemplary embodiments described herein should be considered in a descriptive sense only and not for limiting purposes. The description of features or aspects in each exemplary embodiment should typically be considered to be applicable to other similar features or aspects in other exemplary embodiments. Although one or more exemplary embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that various changes in form and detail may be made therein without departing from the spirit and scope as defined by the appended claims.
Claims
1. A light emitting device, comprising: a first electrode; a second electrode facing the first electrode; as well as an intermediate layer disposed between the first electrode and the second electrode, The intermediate layer includes an emission layer and an emission auxiliary layer, The emission auxiliary layer is arranged between the emission layer and the first electrode, The emission layer includes a first host and a first dopant, The emission auxiliary layer includes a second host and a second dopant, and The second dopant is represented by Formula 1: Formula 1 Among them, in formula 1, M1 is cobalt, copper, zinc, gallium, germanium, zirconium, ruthenium, rhodium, palladium, silver, rhenium, platinum, or gold, X1 is O, S, N(R'), P(R'), B(R'), C(R')(R"), or Si(R')(R"), X2-X4 are each independently C or N, The bond between X1 and M1 is a covalent bond, one bond selected from the bond between X2 and M1, the bond between X3 and M1, and the bond between X4 and M1 is a covalent bond, and the remaining two bonds are coordination bonds, Y1 and Y3-Y5 are each independently C or N, X2 and Y3, X2 and Y4, Y4 and Y5, X 51 and Y3, and X 51 and Y5 are connected to each other via chemical bonds, Ring CY1, ring CY2, ring CY3, and ring CY4 are each independently C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic groups, Ring CY5, ring CY2, ring CY3, and M1 form a 6-membered cyclometalated ring, T1 is a single bond, a double bond, *-N(R5)-*', *-B(R5)-*', *-P(R5)-*', *-C(R5)(R6)-*', *-Si(R5)(R6)-*', *-Ge(R5)(R6)-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R5)=*', *=C(R5)-*', *-C(R5)=C(R6)-*', *-C(=S)-*', or *-C≡C-*', wherein * and *' each represent a binding site to an adjacent atom, X 51 For O, S, N(R7), C(R7)(R8), Si(R7)(R8), Ge(R7)(R8), C(=O), N, C(R7), Si(R7), or Ge(R7), R1-R8, R', and R" are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 Arylalkyl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 heteroarylthio, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(═O)(Q8)(Q9), or -P(Q8)(Q9), a1-a4 are each independently an integer of 0-20, At least one of R1, R3, or R4 is not hydrogen, Two or more of R1 are optionally linked to each other to form an unsubstituted or substituted group. 10a Substituted C5-C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups, Two or more of R2 are optionally linked to each other to form an unsubstituted or substituted group. 10a Substituted C5-C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups, Two or more of R3 are optionally linked to each other to form an unsubstituted or substituted group. 10a Substituted C5-C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups, Two or more of R4 are optionally linked to each other to form an unsubstituted or substituted group. 10a Substituted C5-C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups, Two or more of R1-R4 are optionally linked to each other to form an unsubstituted or substituted group. 10a Substituted C5-C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups, R 10a As described for R1, Substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C1-C 60 Alkoxy, substituted C1-C 60 Alkylthio, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkyl aryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C1-C 60 Heteroaryl, substituted C2-C 60 Alkyl heteroaryl, substituted C2-C 60 Heteroarylalkyl, substituted C1-C 60 Heteroaryloxy, substituted C1-C 60 Substituents of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio; C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-Ge(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(=O)(Q 18 )(Q 19 )、-P(Q 18 )(Q 19 ), or a combination thereof; C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-Ge(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(=O)(Q 28 )(Q 29 )、-P(Q 28 )(Q 29 ), or a combination thereof; -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-Ge(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39 )、 or -P(Q 38 )(Q 39 ); or Its combination, and Q1-Q9, Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 Arylalkyl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group. The light emitting device according to claim 1 , wherein M1 is platinum. The light emitting device according to claim 1 , wherein X 1 is O or S.
4. The light emitting device according to claim 1, wherein X2 and X4 are each N, and X3 is C.
5. The light emitting device according to claim 1, wherein i) X2 and X4 are each N, X3 is C, the bond between X2 and M1 is a coordinate bond, the bond between X4 and M1 is a coordinate bond, and the bond between X3 and M1 is a covalent bond, ii) X2 and X3 are each N, X4 is C, the bond between X2 and M1 is a coordinate bond, the bond between X3 and M1 is a coordinate bond, and the bond between X4 and M1 is a covalent bond, or iii) X3 and X4 are each N, X2 is C, the bond between X3 and M1 is a coordinate bond, the bond between X4 and M1 is a coordinate bond, and the bond between X2 and M1 is a covalent bond.
6. The light-emitting device of claim 1 , wherein ring CY1, ring CY2, ring CY3, and ring CY4 are each independently a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzogermanol group, a dibenzoselenophene group, a benzofluorene group, a benzocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a naphthobenzosilole group, a naphthobenzoborole group, a naphthobenzophosphole group, a naphthobenzogermanol group, a naphthobenzoselenophene group, a dibenzofluorene group, a benzocarbazole group, a dinaphthofuran group, a naphthobenzothiophene group, a naphthobenzosilole group, a naphthobenzoborole group, a naphthobenzophosphole group, a naphthobenzogermanol group, a naphthobenzoselenophene group, a dibenzofluorene group, a benzocarbazole group, a dinaphthofuran group, a dibenzo a naphthothiophene group, a dinaphthothiole group, a dinaphthoborole group, a dinaphthophosphoside group, a dinaphthogermanol group, a dinaphthoselenophene group, an indenophenanthrene group, an indolephenanthrene group, a phenanthrenebenzofuran group, a phenanthrenebenzothiophene group, a phenanthrenebenzothiole group, a phenanthrenebenzoborole group, a phenanthrenebenzophosphoside group, a phenanthrenebenzogermanol group, a phenanthrenebenzoselenophene group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzothiole group, an azadibenzoborole group, an azadibenzophosphoside group, an azadibenzogermanol group, an azadibenzoselenophene group, an azabenzofluorene group, Azabenzocarbazole group, azanaphthobenzofuran group, azanaphthobenzothiophene group, azanaphthobenzothiorrole group, azanaphthobenzoborole group, azanaphthobenzophosphole group, azanaphthobenzogermerole group, azanaphthobenzoselenophene group, azadibenzofluorene group, azadibenzocarbazole group, azadinaphthofuran group, azadinaphthothiophene group, azadinaphthothiorrole group, azadinaphthoborole group, azadinaphthophosphole group, azadinaphthogermerole group, azadinaphthoselenophene group, azaindenophenanthrene group, azaindolinphenanthrene group, azaphenanthrenebenzofuran group, azaphenanthrenebenzothiophene group, azaphenanthrenebenzothiorrole group, aza a phenylene group, an azaphenanthrobenzoborole group, an azaphenanthrobenzophosphole group, an azaphenanthrobenzogermanole group, an azaphenanthrobenzoselenophene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, a benzoquinazoline group, a phenanthroline group, a phenanthridine group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, a norbornene group, a phenyl group condensed with an adamantane group, a phenyl group condensed with a norbornane group, a pyridine group condensed with an adamantane group, or a pyridine group condensed with a norbornane group.
7. The light emitting device of claim 1, wherein R1, R3, and R4 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, cyano, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Heterocycloalkyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 Arylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 a heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
8. The light emitting device according to claim 1, wherein the light emitting device satisfies at least one of conditions 1 to 3: Condition 1 At least one of R1 is not hydrogen Condition 2 At least one of R3 is not hydrogen Condition 3 At least one of R4 is not hydrogen.
9. The light emitting device according to claim 1, wherein the first dopant is represented by Formula 2: Formula 2 <h2 style=";text-align:left;direction:ltr">M2(L1)<h2 style=";text-align:left;direction:ltr"> n1 <h2 style=";text-align:left;direction:ltr"> (L2)<h2 style=";text-align:left;direction:ltr"> n2 in, In formula 2, M2 is iridium, cobalt, copper, zinc, gallium, germanium, zirconium, ruthenium, rhodium, palladium, silver, rhenium, platinum, or gold, L1 is a ligand represented by formula 2-1, and L2 is a ligand represented by formula 2-2, n1 and n2 are each independently 1 or 2, and the sum of n1 and n2 is 3: Formula 2-1 Formula 2-2 Among them, in formulas 2-1 and 2-2, Y1-Y4 are each independently C or N, Ring A1, Ring A2, Ring A3, and Ring A4 are each independently C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic groups, W1-W4 are each independently a single bond, unsubstituted or substituted with at least one R 10a Substituted C5-C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups, d1-d4 and e1-e4 are each independently an integer of 0-20, Z1-Z4 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 Arylalkyl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q 41 )(Q 42 )、-Si(Q 43 )(Q 44 )(Q 45 )、-Ge(Q 43 )(Q 44 )(Q 45 )、-B(Q 46 )(Q 47 )、-P(=O)(Q 48 )(Q 49 ), or -P(Q 48 )(Q 49 ), Two or more of Z1 are optionally linked to each other to form a 10a Substituted C5-C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups, Two or more of Z2 are optionally linked to each other to form an unsubstituted or substituted group. 10a Substituted C5-C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups, Two or more of Z1 and Z2 are optionally linked to each other to form a 10a Substituted C5-C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups, Two or more of Z3 are optionally linked to each other to form an unsubstituted or substituted group. 10a Substituted C5-C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups, Two or more of Z4 are optionally linked to each other to form a 10a Substituted C5-C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups, Two or more of Z3 and Z4 are optionally linked to each other to form a 10a Substituted C5-C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups, R 10a As described in claim 1, Q 41 -Q 49 Each as described in claim 1 with respect to Q1, and Substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C1-C 60 Alkoxy, substituted C1-C 60 Alkylthio, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkyl aryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C1-C 60 Heteroaryl, substituted C2-C 60 Alkyl heteroaryl, substituted C2-C 60 Heteroarylalkyl, substituted C1-C 60 Heteroaryloxy, substituted C1-C 60 Substituents of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are as described in claim 1 .
10. The light emitting device of claim 9, wherein M2 is iridium.
11. The light emitting device according to claim 9, wherein Y1 and Y3 are each N, and Y2 and Y4 are each C.
12. The light emitting device according to claim 9, wherein Ring A3 is i) a polycyclic ring group in which two or more 5-membered rings are fused to each other, ii) a polycyclic ring group in which two or more 6-membered rings are fused to each other, or iii) a polycyclic ring group in which at least one 5-membered ring and at least one 6-membered ring are fused to each other, The 5-membered ring is a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a thiole group, a borocyclopentadiene group, a phosphole group, a germanocyclopentadiene group, a selenophene group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, or an azathiole group, and The 6-membered ring is an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
13. The light emitting device of claim 9, wherein the ring A1 and the ring A3 are different from each other.
14. The light emitting device according to claim 9, wherein e1 and d1 are each not 0, and At least one Z1 is deuterated C1-C 20 Alkyl, -Si(Q 43 )(Q 44 )(Q 45 ), or -Ge(Q 43 )(Q 44 )(Q 45 ).
15. The light emitting device according to claim 9, wherein the first dopant satisfies at least one of conditions (1) to (4): Condition (1) In formula 2-1, e1 and d1 are not 0, and At least one Z1 comprises deuterium Condition (2) In formula 2-1, e2 and d2 are not 0, and At least one Z2 comprises deuterium Condition (3) In formula 2-2, e3 and d3 are not 0, and At least one Z3 includes deuterium Condition (4) In formula 2-2, e4 and d4 are not 0, and At least one Z4 comprises deuterium. 16 . The light emitting device of claim 1 , wherein an amount of the second dopant in the emission assisting layer is 20 wt % or less based on a total weight of the emission assisting layer.
17. The light emitting device of claim 1, wherein the light emitting device satisfies Equation 1: Equation 1 E HOMO (D1)>E HOMO (D2) Among them, In equation 1, E HOMO (D1) represents the highest occupied molecular orbital energy level of the first dopant, E HOMO (D2) represents the highest occupied molecular orbital energy level of the second dopant, and E HOMO (D1) and E HOMO (D2) are each a negative value measured in an ambient atmosphere by using a photoelectron spectroscopy apparatus.
18. The light emitting device according to claim 1, wherein The first electrode is an anode, The second electrode is a cathode, The intermediate layer further includes a hole transport region disposed between the first electrode and the emission layer, and an electron transport region disposed between the emission layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer, or a combination thereof.
19. The light emitting device according to claim 1, wherein The emission layer is in direct contact with the emission auxiliary layer, and The emission-assisting layer does not emit light.
20. An electronic device comprising the light emitting device according to any one of claims 1 to 19.
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