Composition, layer comprising the composition, light-emitting device comprising the composition, and electronic device comprising the light-emitting device
By using a compound composition with a specific structure as an emission layer in an organic light-emitting device, the problems of insufficient luminous efficiency and lifespan in the prior art are solved, and an organic light-emitting device with high efficiency and long lifespan is achieved.
Patent Information
- Application Number
- CN202210624218.9
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2021-06-03
- Filing Date
- 2022-06-01
- Publication Date
- 2025-10-10
- Estimated Expiration
- 2042-06-01
AI Technical Summary
Existing organic light-emitting devices have deficiencies in luminous efficiency and lifespan characteristics, making it difficult to meet high performance requirements.
A composition consisting of a first compound and a second compound of a specific structure is used in the organic layer, including platinum, palladium or gold as M1, iridium as M2, and through the combination of specific ligands and connecting groups, a heteroleptic or homoleptic complex is formed to constitute the emission layer to improve the luminous efficiency and life.
The luminous efficiency and lifespan characteristics of organic light-emitting devices are significantly improved to meet high performance requirements.
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Figure CN115433566B_ABST
Abstract
Description
[0001] Cross-reference to related applications
[0002] This application is based on and claims the benefit of priority from Korean Patent Application No. 10-2021-0072365 filed in the Korean Intellectual Property Office on June 3, 2021, and all rights arising therefrom, the contents of which are incorporated herein by reference in their entirety. Technical Field
[0003] The present disclosure relates to compositions, layers including the compositions, light-emitting devices including the compositions, and electronic devices including the light-emitting devices. Background Art
[0004] Among light emitting devices, an organic light emitting device (OLED) is a self-emitting device that has improved characteristics in terms of viewing angle, response time, brightness, driving voltage, and response speed and produces a full-color image.
[0005] In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes an emissive layer. A hole transport region may be located between the anode and the emissive layer, and an electron transport region may be located between the emissive layer and the cathode. Holes provided from the anode may move toward the emissive layer through the hole transport region, and electrons provided from the cathode may move toward the emissive layer through the electron transport region. Holes and electrons recombine in the emissive layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light. Summary of the Invention
[0006] Provided are a composition capable of providing excellent luminous efficiency and lifespan characteristics, a layer including the composition, a light-emitting device including the composition, and an electronic device including the light-emitting device.
[0007] Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
[0008] According to one aspect, a composition is provided, comprising
[0009] A first compound represented by Formula 1 and a second compound represented by Formula 2:
[0010] Formula 1
[0011]
[0012] Formula 2
[0013] M2(L 11 ) n11 (L 12 ) n12(L 13 ) n13
[0014]
[0015] Wherein, in Formula 1, M1 is platinum (Pt), palladium (Pd), or gold (Au),
[0016] In formula 2, M2 is iridium (Ir),
[0017] In formula 2, L 11 is a ligand represented by formula 2-1,
[0018] In formula 2, L 12 is a ligand represented by formula 2-2,
[0019] In formula 2, L 13 is a ligand represented by formula 2-1 or 2-2,
[0020] In formula 2, L 11 and L 12 Different from each other,
[0021] In Formula 2, n11, n12, and n13 are each independently 0, 1, 2, or 3, and n11+n12+n13 is 3,
[0022] In formulas 1, 2-1, and 2-2, X1-X4 and Y1-Y4 are each independently C or N,
[0023] In Formula 1, X5-X8 are each independently a chemical bond, O, S, N(R'), C(R')(R"), or C(=O), and at least one of X5-X8 is not a chemical bond,
[0024] In Formula 1, two bonds among the bond between X5 or X1 and M1, the bond between X6 or X2 and M1, the bond between X7 or X3 and M1, and the bond between X8 or X4 and M1 are each a coordinate bond, and the other two bonds are each a covalent bond,
[0025] In Formulas 1, 2-1, and 2-2, Ring CY1-Ring CY4 and Ring A1-Ring A4 are each independently C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic groups,
[0026] In formula 1, T 11 -T 14 Each independently represents a single bond, a double bond, *-N(R 5a )-*'、*-B(R 5a )-*'、*-P(R 5a )-*'、*-C(R5a )(R 5b )-*'、*-Si(R 5a )(R 5b )-*'、*-Ge(R 5a )(R 5b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 5a )=*'、*=C(R 5a )-*'、*-C(R 5a )=C(R 5b )-*', *-C(=S)-*', *-C≡C-*', unsubstituted or substituted with at least one R 10a Substituted C5-C 30 Carbocyclic groups, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 A heterocyclic group, wherein * and *' each represent a binding site to an adjacent atom,
[0027] In Formula 1, n1-n4 are each independently 0 or 1, and three or more of n1-n4 are each 1,
[0028] In formula 1, when n1 is 0, T 11 does not exist, when n2 is 0, T 12 Does not exist, when n3 is 0, T 13 does not exist, and when n4 is 0, T 14 does not exist,
[0029] In Formulas 1, 2-1, and 2-2, L1-L4 and W1-W4 are each independently a single bond, unsubstituted or replaced by at least one R 10a Substituted C1-C 20 Alkylene, unsubstituted or substituted by at least one R 10a Substituted C5-C 30 Carbocyclic groups, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups,
[0030] In Formula 1, b1-b4 are each independently an integer of 1-10,
[0031] In Formulas 1, 2-1, and 2-2, R1-R4, R 5a 、R 5bR', R", and Z1-Z4 are each 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 C2-C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(═O)(Q8)(Q9), or -P(Q8)(Q9),
[0032] In formulas 1, 2-1, and 2-2, c1-c4, a1-a4, e1-e4, and d1-d4 are each independently an integer of 0-20,
[0033] The second compound is not tris[2-phenylpyridine]iridium,
[0034] In Formulae 1, 2-1, and 2-2, at least two substituents from the following groups are each independently optionally linked to each other to form a group that is unsubstituted or substituted with at least one R 10a Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R10a Substituted C1-C 30 Heterocyclic group: i) two or more of multiple R1; ii) two or more of multiple R2; iii) two or more of multiple R3; iv) two or more of multiple R4; v) R 5a and R 5b vi) two or more of a plurality of Z1; vii) two or more of a plurality of Z2; viiii) two or more of a plurality of Z3, ix) two or more of a plurality of Z4; x) R1-R4, R 5a , and R 5b and xi) two or more of Z1-Z4,
[0035] R 10a As defined with respect to R1,
[0036] In formulas 2-1 and 2-2, * and *' each represent a binding site with M2, and
[0037] 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 Alkylaryl, 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 C2-C 60 At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is:
[0038] Deuterium, -F, -Cl, -Br, -I, -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;
[0039] 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, -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 fused polycyclic group, monovalent non-aromatic fused 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;
[0040] 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, -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 fused polycyclic group, monovalent non-aromatic fused 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;
[0041] -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
[0042] Its combination,
[0043] Among them, Q1-Q9, Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 Each independently represents: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, or C1-C2-C3-C4-C6-C1-C2-C3-C1-C2 ... 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 60Heteroarylthio group, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, C1-C 60 Alkyl, C6-C 60 aryl, or a combination thereof.
[0044] According to another aspect, a layer comprising the composition is provided.
[0045] According to yet another aspect, a light emitting device is provided, comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an emission layer, and wherein the organic layer comprises the composition.
[0046] For example, the emission layer of the organic layer in the light emitting device may include the composition.
[0047] According to another aspect, an electronic device including the light emitting device is also provided. BRIEF DESCRIPTION OF THE DRAWINGS
[0048] From the combination Figure 1 The above and other aspects, features, and advantages of one or more exemplary embodiments will become more apparent upon consideration of the following detailed description. Figure 1 Schematic cross-sectional views showing light emitting devices according to one or more embodiments. DETAILED DESCRIPTION
[0049] Embodiments will now be described in detail, examples of which are shown in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout the specification. In this regard, the present embodiment may have different forms and should not be construed as being limited to the description set forth herein. Therefore, the following description of the embodiments is merely to illustrate aspects by reference to the accompanying drawings. As used herein, the term "and / or" includes any and all combinations of one or more of the relevant enumerated items. Expressions such as "at least one (kind)" when preceding or following a list of elements modify the entire list of elements and do not modify the individual elements of the list.
[0050] The terms used herein are only for the purpose of describing one or more exemplary embodiments and are not intended to be restrictive. As used herein, the singular forms "a, an" and "the" are also intended to include plural forms, unless the context clearly indicates otherwise. The term "or" means "and / or". It will be further understood that the terms "comprising" or "including" when used in this specification indicate the presence of stated features, regions, wholes, steps, operations, elements and / or components, but do not exclude the presence or addition of one or more other features, regions, wholes, steps, operations, elements, components, and / or their collections.
[0051] 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 another element, component, region, layer or part. Therefore, without departing from the teachings of this embodiment, the first element, component, region, layer or part discussed below can be referred to as the second element, component, region, layer or part.
[0052] Exemplary embodiments are described herein with reference to cross-sectional views that are schematic representations of idealized embodiments. As such, deviations from the shapes of the figures are to be expected as a result of, for example, manufacturing techniques and / or tolerances. Therefore, the embodiments described herein should not be construed as limited to the specific shapes of the regions as illustrated herein, but rather include deviations in shape resulting from, for example, manufacturing. For example, a region illustrated or described as flat may typically have rough and / or nonlinear features. Furthermore, illustrated sharp corners may be rounded. Therefore, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of the regions and are not intended to limit the scope of the claims.
[0053] It will be understood that when an element is referred to as being “on” another element, it can be directly in contact with the other element or intervening elements may be present. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present.
[0054] 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 defined as such herein.
[0055] As used herein, "about" or "approximately" is inclusive of 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 measurements 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.
[0056] One aspect provides a composition comprising a first compound represented by Formula 1 and a second compound represented by Formula 2:
[0057] Formula 1
[0058]
[0059] Formula 2
[0060] M2(L 11 ) n11 (L 12 ) n12 (L 13 ) n13 .
[0061] In Formula 1, M1 is platinum (Pt), palladium (Pd), or gold (Au).
[0062] For example, in Formula 1, M1 may be Pt.
[0063] In Formula 2, M2 is Ir.
[0064] In formula 2, L 11 is a ligand represented by formula 2-1, L 12 is a ligand represented by formula 2-2, and L 13 is a ligand represented by formula 2-1 or 2-2:
[0065]
[0066] wherein Formulas 2-1 and 2-2 are as described herein.
[0067] In formula 2, L 11 and L 12 Different from each other.
[0068] In formula 2, n11-n13 represent L 11 Quantity to L 13 and are each independently 0, 1, 2, or 3, where n11+n12+n13 is 3. In other words, in Formula 2, the sum of n11, n12, and n13 is equal to 3.
[0069] In one or more embodiments, in Formula 2, n11 may be 1, 2, or 3, and n12 and n13 may each independently be 0, 1, or 2.
[0070] In one or more embodiments, in Formula 2, n12 may be 1, 2, or 3, and n11 and n13 may each independently be 0, 1, or 2.
[0071] In one or more embodiments, n11 may be 1, n12 may be 2, and n13 may be 0.
[0072] In one or more embodiments, n11 may be 2, n12 may be 1, and n13 may be 0.
[0073] In one or more embodiments, n11 may be 3, and n12 and n13 may each be 0.
[0074] In one or more embodiments, n12 may be 3, and n11 and n13 may each be 0.
[0075] The second compound represented by Formula 2 may be a heteroleptic complex or a homoleptic complex.
[0076] In one or more embodiments, the second compound may be a heteroleptic complex.
[0077] In Formulae 1, 2-1, and 2-2, X1-X4 and Y1-Y4 are each independently C or N.
[0078] In one or more embodiments, at least one of X1-X4 in Formula 1 may be C.
[0079] In one or more embodiments, X1 of Formula 1 may be C.
[0080] In one or more embodiments, in Formula 1, i) X1 and X3 may each be C, and X2 and X4 may each be N, or ii) X1 and X4 may each be C, and X2 and X3 may each be N.
[0081] In one or more embodiments, in Formulas 2-1 and 2-2, Y1 and Y3 may each be N, and Y2 and Y4 may each be C.
[0082] In Formula 1, X5-X8 are each independently a chemical bond, O, S, N(R'), C(R')(R"), or C(=O), wherein at least one of X5-X8 may not be a chemical bond. R' and R" may each be as defined herein. As used herein, "chemical bond" refers to a covalent bond (e.g., a single bond) or a coordination bond.
[0083] In one or more embodiments, X5 in Formula 1 may not be a chemical bond.
[0084] In one or more embodiments, X5 in Formula 1 may be O or S.
[0085] In one or more embodiments, in Formula 1, X5 may be O or S, and X6-X8 may each be a chemical bond.
[0086] In Formula 1, two bonds among the bond between X5 or X1 and M1, the bond between X6 or X2 and M1, the bond between X7 or X3 and M1, and the bond between X8 or X4 and M1 are each coordinate bonds, and the other two bonds among the bond between X5 or X1 and M1, the bond between X6 or X2 and M1, the bond between X7 or X3 and M1, and the bond between X8 or X4 and M1 are each covalent bonds.
[0087] For example, in Formula 1, the bond between X2 and M1 may be a coordinate bond.
[0088] In one or more embodiments, in Formula 1, the bond between X5 or X1 and M1 and the bond between X3 and M1 may each be a covalent bond, and the bond between X2 and M1 and the bond between X4 and M1 may each be a coordination bond.
[0089] In one or more embodiments, the first compound and the second compound may each be electrically neutral.
[0090] In Formulas 1, 2-1, and 2-2, Ring CY1-Ring CY4 and Ring A1-Ring A4 are each independently C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic group.
[0091] For example, in one or more embodiments, each of ring CY1, ring CY3, and ring CY4 may not be a benzimidazole group.
[0092] For example, in one or more embodiments, in Formulas 1, 2-1, and 2-2, Ring CY1-Ring CY4 and Ring A1-A4 may each independently be i) a first ring, ii) a second ring, iii) a fused ring in which two or more first rings are fused to each other, iv) a fused ring in which two or more second rings are fused to each other, or v) a fused ring in which one or more first rings are fused to one or more second rings,
[0093] The first ring can be a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a thiole group, a boroheterocyclopentadiene group, a phosphoheterocyclopentadiene group, a germanoheterocyclopentadiene group, a selenophene group, Azole group, oxadiazole group, a triazole 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
[0094] The second ring may be an adamantane group, a norbornane group, a norbornene group, a piperidine 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.
[0095] In one or more embodiments, in Formulas 1, 2-1, and 2-2, ring CY1-ring CY4 and ring A1-ring A4 can each independently be 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, groups, 1,2,3,4-tetrahydronaphthyl groups, cyclopentadienyl groups, pyrrolyl groups, furanyl groups, thiophenyl groups, silolyl groups, borolyl groups, phospholyl groups, germolyl groups, selenolyl groups, indenyl groups, indolyl groups, benzofuranyl groups, benzothiophenyl groups, benzosilolyl groups, benzo phospholyl groups, benzo germolyl groups, benzo selenolyl groups, fluorenyl groups, carbazolyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, dibenzosilolyl groups, dibenzo phospholyl groups, dibenzo germolyl groups, dibenzo selenolyl groups, benzo fluorenyl groups, benzo carbazolyl groups, naphthobenzofuranyl groups, naphthobenzothiophenyl groups, naphthobenzosilolyl groups, naphthobenzo phospholyl groups, naphthobenzo germolyl groups, naphthobenzo selenolyl groups, diphenyl fluorenyl groups, diphenyl carbazolyl groups, dinaphthofuranyl groups, dinaphthothiophenyl groups, dinaphthosilolyl groups, dinaphtho phospholyl groups, dinaphtho germolyl groups, dinaphtho selenolyl groups, indenophenanthrenyl groups, indolophenanthrenyl groups, phenanthrenobenzofuranyl groups, phenanthrenobenzothiophenyl groups, phenanthrenobenzosilolyl groups, phenanthrenobenzo phospholyl groups, phenanthrenobenzo germolyl groups, phenanthrenobenzo selenolyl groups, dibenzothiophene 5-oxide groups, 9H-fluorene-9-one groups, dibenzothiophene 5,5-oxide group, azaindole group, azaindazole group, azabenzofuran group, azabenzothiophene group, azabenzothiazole group, azabenzophosphole group, azabenzogermyl group, azabenzoselenophene group, azacarbazole group, azadibenzofuran group, azadibenzothiophene group, azadibenzothiazole group, azadibenzophosphole group, azadibenzogermyl group, azadibenzoselenophene group, azabenzofluorene group, azabenzocarbazole group, azanaphthobenzofuran group, azanaphthobenzothiophene group, azanaphthobenzothiazole group, azanaphthobenzophosphole group, azanaphthobenzogermyl group, azanaphthobenzoselenophene group, azadibenzofluorene group, azadibenzocarbazole group, azanaphthodibenzofuran group, azanaphthodibenzothiophene group, azanaphthodibenzothiazole group, azanaphthodibenzophosphole group, azanaphthodibenzogermyl group, azanaphthodibenzoselenophene group, azaindacenophthalene group, azaindolenaphthalene group, azaphenanthrobenzofuran group, azaphenanthrobenzothiophene group, azaphenanthrobenzothiazole group, azaphenanthrobenzophosphole group, azaphenanthrobenzogermyl group, azaphenanthrobenzoselenophene group, azadibenzothiophene 5-oxide group, azaindacen-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, azole group, iso azole group, thiazole group, iso azole group, thiazole group, iso azole group, thiazole group, iso azole group, thiazole group, iso azole group, thiazole group, iso azole group, thiazole group, iso azole group, thiazole group, iso oxadiazole group, pyridothiadiazole group, pyrimidopyrrole group, pyrimidopyrazole group, pyrimidoimidazole group, pyrimidothiadiazole group, Azole group, pyrimidinyl isocyanate Azole group, pyrimidothiazole group, pyrimidisothiazole group, pyrimidothiazole group oxadiazole group, pyrimidothiadiazole group, naphthopyrrole group, naphthopyrazole group, naphthoimidazole group, naphtho Azole group, naphthoiso Azole group, naphthothiazole group, naphthoisothiazole group, naphtho oxadiazole group, naphthiadiazole group, phenanthropyrrole group, phenanthropyrazole group, phenanthroimidazole group, phenanthro Azole group, phenanthroline Azole group, phenanthiothiazole group, phenanthroisothiazole group, phenanthro a oxadiazole group, a phenanthiadiazole 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.
[0096] In one or more embodiments, ring CY1 and ring CY3 in Formula 1 may each independently be:
[0097] a phenyl group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, or a dibenzosilole group; or
[0098] a phenyl group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, or a dibenzosilole group, each fused with at least one of the following: a cyclohexane group, a cyclohexene group, a norbornane group, a piperidine group, or a combination thereof.
[0099] In one or more embodiments, ring CY2 in Formula 1 may be:
[0100] an imidazole group, a benzimidazole group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group; or
[0101] an imidazole group, a benzimidazole group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group, each fused to at least one of a cyclohexane group, a cyclohexene group, a norbornane group, a phenyl group, a pyridine group, a pyrimidine group, or a combination thereof.
[0102] In one or more embodiments, ring CY4 in Formula 1 may be:
[0103] a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzoselenophene group, an azacarbazole group, an azafluorene group, or an azadibenzosilole group; or
[0104] a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzoselenophene group, an azacarbazole group, an azafluorene group, or an azadibenzosilole group, each fused to at least one of the following: a cyclohexane group, a cyclohexene group, a norbornane group, a phenyl group, a pyridine group, a pyrimidine group, or a combination thereof.
[0105] In Formulae 2-1 and 2-2, Ring A1 and Ring A3 may be different from each other.
[0106] In one or more embodiments, the monocyclic group containing Y1 in ring A1, the monocyclic group containing Y2 in ring A2, and the monocyclic group containing Y4 in ring A4 may each be a 6-membered ring.
[0107] In one or more embodiments, the monocyclic group containing Y3 in ring A3 may be a 6-membered ring.
[0108] In one or more embodiments, the monocyclic group containing Y3 in ring A3 may be a 5-membered ring.
[0109] In one or more embodiments, the monocyclic group containing Y1 in ring A1 may be a 6-membered ring, and the monocyclic group containing Y3 in ring A3 may be a 5-membered ring.
[0110] In one or more embodiments, in Formulas 2-1 and 2-2, Ring A1 and Ring A3 may each independently be i) one of Group A, ii) a polycyclic group in which two or more of Group A are fused to each other, or iii) a polycyclic group in which at least one of Group A and at least one of Group B are fused to each other,
[0111] wherein group A may include a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, and
[0112] Group B may include a cyclohexane group, a cyclohexene group, a norbornane group, a phenyl group, a furan group, a thiophene group, a selenophene group, a pyrrole group, a cyclopentadiene group, or a silole group.
[0113] In one or more embodiments, in Formula 2-2, Ring A3 may be i) one of Group C, ii) a polycyclic group in which two or more of Group C are fused to each other, or iii) a polycyclic group in which at least one of Group C and at least one of Group D are fused to each other,
[0114] Wherein group C may include pyrrole group, pyrazole group, imidazole group, triazole group, Azole group, iso an azole group, a thiazole group, or an isothiazole group, and
[0115] Group D may include a cyclohexane group, a cyclohexene group, a norbornane group, a phenyl group, a furan group, a thiophene group, a selenophene group, a cyclopentadiene group, a silole group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group.
[0116] In one or more embodiments, Ring A1 in Formula 2-1 may be:
[0117] a pyridine group, a pyrimidine group, a pyridazine group, or a pyrazine group; or
[0118] A pyridine group, a pyrimidine group, a pyridazine group, or a pyrazine group, each fused to at least one of a cyclohexane group, a norbornane group, a phenyl group, or a combination thereof.
[0119] In one or more embodiments, Ring A3 in Formula 2-2 may be:
[0120] a pyridine group, a pyrimidine group, a pyridazine group, or a pyrazine group;
[0121] a pyridine group, a pyrimidine group, a pyridazine group, or a pyrazine group, each fused to at least one of a cyclohexane group, a norbornane group, a phenyl group, or a combination thereof; or
[0122] Imidazole group, benzimidazole group, naphthimidazole group, phenanthimidazole group, pyridimidazole group, Azole group, benzo Azole group, naphtho Azole group, phenanthroline Azole group, pyrido an oxazole group, a thiazole group, a benzothiazole group, a naphthiazole group, a phenanthiazole group, or a pyridothiazole group.
[0123] In one or more embodiments, in Formulas 2-1 and 2-2, Ring A2 and Ring A4 may be different from each other.
[0124] In one or more embodiments, in Formulas 2-1 and 2-2, Ring A2 and Ring A4 may each independently be i) one of Group E, ii) a polycyclic group in which two or more of Group E are fused to each other, or iii) a polycyclic group in which at least one of Group E and at least one of Group F are fused to each other,
[0125] wherein group E may include a phenyl group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, and
[0126] Group F may include furan group, thiophene group, selenophene group, pyrrole group, cyclopentadiene group, thiol group, pyrazole group, imidazole group, Azole group, thiazole group, iso an azole group, or an isothiazole group.
[0127] In one or more embodiments, in Formula 2-1, Ring A2 may be a polycyclic group in which two or more of Group E and at least one of Group F are fused to each other.
[0128] In one or more embodiments, in Formula 2-2, Ring A4 may be a polycyclic group in which two or more of Group E and at least one of Group F are fused to each other.
[0129] In one or more embodiments, Ring A2 in Formula 2-1 may be:
[0130] a phenyl group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, or a dibenzosilole group; or
[0131] a phenyl group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, or a dibenzosilole group, each fused to a cyclohexane group, a norbornane group, a phenyl group, or a combination thereof.
[0132] In one or more embodiments, Ring A4 in Formula 2-2 may be:
[0133] a phenyl group, a naphthalene group, a phenanthrene group, a phenanthrenylbenzofuran group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, a dibenzosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzoselenophene group, an azacarbazole group, an azafluorene group, or a dibenzosilole group; or
[0134] a phenyl group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, a dibenzosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzoselenophene group, an azacarbazole group, an azafluorene group, or a dibenzosilole group, each fused to at least one of the following: a phenyl group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a cyclohexane group, a norbornane group, a furan group, a thiophene group, a selenophene group, a pyrrole group, a cyclopentadiene group, a silole group, a pyrazole group, an imidazole group, Azole group, thiazole group, iso an azole group, an isothiazole group, or a combination thereof.
[0135] In formula 1, T 11 -T 14 Can be independently a single bond, a double bond, *-N(R 5a )-*'、*-B(R 5a )-*'、*-P(R 5a )-*'、*-C(R 5a )(R 5b )-*'、*-Si(R 5a )(R 5b )-*'、*-Ge(R 5a )(R 5b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 5a )=*'、*=C(R 5a )-*'、*-C(R 5a )=C(R 5b )-*', *-C(=S)-*', *-C≡C-*', unsubstituted or substituted with at least one R 10a Substituted C5-C 30 Carbocyclic groups, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic group, wherein * and *' each represent a bonding site to an adjacent atom.
[0136] For example, in Equation 1, T 11 and T 12 Each may be a single bond, and T 13 Can be a single bond, *-N(R 5a )-*'、*-B(R 5a )-*'、*-P(R 5a )-*'、*-C(R 5a )(R 5b )-*'、*-Si(R5a )(R 5b )-*'、*-Ge(R 5a )(R 5b )-*', *-S-*', or *-O-*'.
[0137] In Formula 1, n1-n4 each represent T 11 Quantity to T 14 and are each independently 0 or 1, wherein three or more of n1-n4 are 1. That is, the first compound represented by Formula 1 may have a tetradentate ligand.
[0138] In formula 1, when n1 is 0, T 11 does not exist (ie, ring CY1 and ring CY2 are not connected to each other), when n2 is 0, T 12 does not exist (ie, ring CY2 and ring CY3 are not connected to each other), when n3 is 0, T 13 does not exist (ie, ring CY3 and ring CY4 are not connected to each other), and when n4 is 0, T 14 Not present (ie, loop CY4 and loop CY1 are not connected to each other).
[0139] In one or more embodiments, in Formula 1, n1-n3 may each be 1, and n4 may be 0.
[0140] In one or more embodiments, in Formulas 1, 2-1, and 2-2, L1-L4 and W1-W4 are each independently a single bond, unsubstituted or replaced by at least one R 10a Substituted C1-C 20 Alkylene, unsubstituted or substituted by at least one R 10a Substituted C5-C 30 Carbocyclic groups, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic group.
[0141] In one or more embodiments, in Formulas 1, 2-1, and 2-2, L1-L4 and W1-W4 may each independently be:
[0142] a single bond; or
[0143] Each is unsubstituted or replaced by at least one R 10a Substituted C1-C 20 Alkylene group, cyclopentene group, cyclohexane group, cyclohexene group, phenyl group, naphthalene group, anthracene group, phenanthrene group, benzo[9,10]phenanthrene group, pyrene group, group, cyclopentadiene group, 1,2,3,4-tetrahydronaphthalene group, thiophene group, furan group, indole group, benzoborole group, benzophosphole group, indene group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, aza benzothiole group, azabenzogermanol group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborol group, azadibenzophosphole group, azafluorene group, azadibenzothiophene group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-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, phenanthroline group, pyrrole group, pyrazole group, imidazole group, triazole group, Azole group, iso azole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo Azole group, benzothiazole group, benzo an oxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, or a norbornene group.
[0144] In one or more embodiments, in Formulas 1, 2-1, and 2-2, L1-L4 and W1-W4 may each independently be:
[0145] a single bond; or
[0146] Each is unsubstituted or replaced by at least one R 10a Substituted C1-C 20 an alkylene group, a benzene group, a naphthalene group, a pyridine group, a fluorene group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group.
[0147] In one or more embodiments, in Formulas 1, 2-1, and 2-2, L1-L4 and W1-W4 may each independently be:
[0148] a single bond; or
[0149] C1-C 20 Alkylene, benzene, naphthyl, dibenzofuran, or dibenzothiophene: deuterium, -F, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, C3-C 10 Cycloalkyl, deuterated C3-C 10 Cycloalkyl, fluorinated C3-C 10 Cycloalkyl, (C1-C 20 Alkyl) C3-C 10 Cycloalkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, naphthyl, pyridyl, furyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, or a combination thereof.
[0150] In Formula 1, b1-b4 represent the number of L1 to the number of L4, and are each independently an integer of 1-10. When b1 is 2 or greater, two or more L1s may be the same or different from each other, when b2 is 2 or greater, two or more L2s may be the same or different from each other, when b3 is 2 or greater, two or more L3s may be the same or different from each other, and when b4 is 2 or greater, two or more L4s may be the same or different from each other. For example, b1-b4 may each independently be 1, 2, or 3.
[0151] In Formulas 1, 2-1, and 2-2, R1-R4, R 5a 、R 5b R', R", and Z1-Z4 are each 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 10Heterocycloalkenyl, 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 fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(═O)(Q8)(Q9), or -P(Q8)(Q9). Q1-Q9 are as defined herein.
[0152] In Formulas 1, 2-1, and 2-2, R1-R4, R 5a 、R 5b , R, R", and Z1-Z4 may each independently be:
[0153] 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, C1-C 20 Alkyl, C1-C 20 Alkenyl, C1-C 20 Alkoxy, or C1-C 20 alkylthio;
[0154] C1-C 20 Alkyl, C1-C 20 Alkenyl, C1-C 20 Alkoxy, or C1-C 20 Alkylthio: deuterium, -F, -Cl, -Br, -I, -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 10alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, (C1-C 20 Alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 Alkyl)cyclooctyl, (C1-C 20 Alkyl) adamantyl, (C1-C 20 Alkyl) norbornyl, (C1-C 20 Alkyl) norbornene, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 Alkyl) cycloheptenyl, (C1-C 20 alkyl) bicyclo[1.1.1]pentyl, (C1-C 20 alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 alkyl) bicyclo[2.2.1]heptyl, (C1-C 20 alkyl) bicyclo[2.2.2]octyl, phenyl, (C1-C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, or a combination thereof;
[0155] cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, phenyl, (C1-C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazole, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, azacarbazolyl, azadibenzofuranyl, or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -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 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 Alkyl)cyclooctyl, (C1-C 20 Alkyl) adamantyl, (C1-C 20 Alkyl) norbornyl, (C1-C 20 Alkyl) norbornene, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 Alkyl) cycloheptenyl, (C1-C 20 alkyl) bicyclo[1.1.1]pentyl, (C1-C 20 alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 alkyl) bicyclo[2.2.1]heptyl, (C1-C 20 alkyl) bicyclo[2.2.2]octyl, phenyl, (C1-C 20 alkyl)phenyl, deuterated phenyl, fluorinated phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazole, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, or a combination thereof; or
[0156] -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9),
[0157] Wherein Q1-Q9 can be independently:
[0158] Deuterium, -F, -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, - OR
[0159] 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: deuterium, -F, C1-C 10 alkyl, phenyl, or a combination thereof.
[0160] In one or more embodiments, in Formulas 1, 2-1, and 2-2, R1-R4, R 5a 、R 5b , R, R", and Z1-Z4 may each independently be:
[0161] hydrogen, deuterium, -F, or cyano;
[0162] C1-C2 is unsubstituted or substituted with at least one of the following 20 Alkyl: deuterium, -F, cyano, C3-C10 Cycloalkyl, deuterated C3-C 10 Cycloalkyl, fluorinated C3-C 10 Cycloalkyl, (C1-C 20 Alkyl) C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, deuterated C1-C 10 Heterocycloalkyl, fluorinated C1-C 10 Heterocycloalkyl, (C1-C 20 Alkyl)C1-C 10 Heterocycloalkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 alkyl) biphenyl, dibenzofuranyl, deuterated dibenzofuranyl, fluorinated dibenzofuranyl, (C1-C 20 alkyl) dibenzofuranyl, dibenzothiophene, deuterated dibenzothiophene, fluorinated dibenzothiophene, (C1-C 20 alkyl)dibenzothiophene, or a combination thereof;
[0163] C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, phenyl, biphenyl, naphthyl, pyridyl, fluorenyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl: deuterium, -F, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, C1-C 20 Alkoxy, deuterated C1-C 20 Alkoxy, fluorinated C1-C 20 Alkoxy, C1-C 20 Alkylthio, deuterated C1-C 20 Alkylthio, fluorinated C1-C 20 Alkylthio, C3-C 10 Cycloalkyl, deuterated C3-C 10 Cycloalkyl, fluorinated C3-C 10 Cycloalkyl, (C1-C 20 Alkyl) C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, deuterated C1-C 10 Heterocycloalkyl, fluorinated C1-C 10 Heterocycloalkyl, (C1-C 20 Alkyl)C1-C 10 Heterocycloalkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20alkyl)phenyl, biphenyl, deutero-biphenyl, fluorinated biphenyl, (C1-C 20 alkyl)biphenyl, dibenzofuranyl, deutero-dibenzofuranyl, fluorinated dibenzofuranyl, (C1-C 20 alkyl)dibenzofuranyl, dibenzothiophenyl, deutero-dibenzothiophenyl, fluorinated dibenzothiophenyl, (C1-C 20 alkyl)dibenzothiophenyl, or combinations thereof; or
[0164] -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5).
[0165] In one or more embodiments, in Formula 2-1, each of e1and d1may be other than 0, and at least one of the plurality of Z1may be deuterated C1-C 20 alkyl, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5). Q3-Q5may each be as defined herein.
[0166] In one or more embodiments, Q3-Q5may each independently be:
[0167] C1-C 60 alkyl: deuterium, C1-C 60 alkyl, C6-C 60 aryl, or combinations thereof; or
[0168] C6-C 60 aryl: deuterium, C1-C 60 alkyl, C6-C 60 aryl, or combinations thereof.
[0169] In one or more embodiments, Q3-Q5may each independently be:
[0170] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or
[0171] n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, t-pentyl, neopentyl, i-pentyl, s-pentyl, 3-pentyl, s-i-pentyl, phenyl, biphenyl, or naphthyl, each unsubstituted or substituted with deuterium, C1-C 10 alkyl, phenyl, or combinations thereof.
[0172] In one or more embodiments, Q3-Q5 may be the same as each other.
[0173] In one or more embodiments, two or more of Q3-Q5 may be different from each other.
[0174] In one or more embodiments, the second compound may satisfy at least one of conditions (1) to (8):
[0175] Condition (1)
[0176] e1 and d1 in Formula 2-1 are each not 0, and at least one Z1 includes deuterium;
[0177] Condition (2)
[0178] e2 and d2 in Formula 2-1 are each not 0, and at least one Z2 includes deuterium;
[0179] Condition (3)
[0180] e3 and d3 in Formula 2-2 are each not 0, and at least one Z3 includes deuterium;
[0181] Condition (4)
[0182] e4 and d4 in Formula 2-2 are each not 0, and at least one Z4 includes deuterium;
[0183] Condition (5)
[0184] e1 and d1 in Formula 2-1 are each not 0, and at least one Z1 includes a fluorine group;
[0185] Condition (6)
[0186] e2 and d2 in Formula 2-1 are each not 0, and at least one Z2 includes a fluorine group;
[0187] Condition (7)
[0188] e3 and d3 in Formula 2-2 are each not 0, and at least one Z3 includes a fluoro group; or
[0189] Condition (8)
[0190] e4 and d4 in Formula 2-2 are each not 0, and at least one Z4 includes a fluorine group.
[0191] In one or more embodiments, in Formulas 1, 2-1, and 2-2, R1-R4, R 5a 、R 5b , R, R", and Z1-Z4 can each independently be hydrogen, deuterium, -F, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C10 Alkenyl, C1-C 10 Alkoxy, C1-C 10 an 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 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 10-129, a group represented by one of formulae 10-1 to 10-129 in which at least one hydrogen is replaced by deuterium a group represented by one of formulae 10-1 to 10-129, a group represented by one of formulae 10-1 to 10-129 in which at least one hydrogen is replaced by -F, a group represented by one of formulae 10-201 to 10-350, a group represented by one of formulae 10-201 to 10-350 in which at least one hydrogen is replaced by deuterium, a group represented by one of formulae 10-201 to 10-350 in which at least one hydrogen is replaced by -F, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5) (wherein Q3-Q5 may each be as defined herein):
[0192]
[0193]
[0194]
[0195]
[0196]
[0197]
[0198]
[0199]
[0200] In formulae 9-1 to 9-39, 9-201 to 9-237, 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.
[0201] 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 each be, for example, a group represented by one of formulae 9-501 to 9-514 and 9-601 to 9-636:
[0202]
[0203] 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 each be, for example, a group represented by one of formulae 9-701 to 9-710:
[0204]
[0205] 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 be, for example, a group represented by one of formulae 10-501 to 10-553:
[0206]
[0207]
[0208] 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 be, for example, a group represented by one of formulae 10-601 to 10-617:
[0209]
[0210] In Formulas 1, 2-1, and 2-2, c1-c4 represent the number of R1 to R4 respectively; a1-a4 represent the number of *-[(L1) b1 -(R1) c1 ], the number of groups represented by *-[(L2) b2 -(R2) c2 ], the number of groups represented by *-[(L3) b3 -(R3) c3 ], and the number of groups represented by *-[(L4) b4 -(R4) c4 ] represents the number of groups; e1-e4 represent the number of Z1 to the number of Z4; and d1-d4 represent the number of groups represented by *-[W1-(Z1) e1], the number of groups represented by *-[W2-(Z2) e2 ], the number of groups represented by *-[W3-(Z3) e3 ], and the number of groups represented by *-[W4-(Z4) e4 ], and c1-c4, a1-a4, e1-e4, and d1-d4 may each independently be an integer of 0-20. When c1 is 2 or greater, two or more R1s may be the same or different from each other, when c2 is 2 or greater, two or more R2s may be the same or different from each other, when c3 is 2 or greater, two or more R3s may be the same or different from each other, when c4 is 2 or greater, two or more R4s may be the same or different from each other, when a1 is 2 or greater, two or more R1s represented by *-[(L1) b1 -(R1) c1 ] may be the same as or different from each other, and when a2 is 2 or greater, two or more groups represented by *-[(L2) b2 -(R2) c2 ] may be the same as or different from each other. When a3 is 2 or greater, two or more groups represented by *-[(L3) b3 -(R3) c3 ] may be the same as or different from each other, and when a4 is 2 or greater, two or more groups represented by *-[(L4) b4 -(R1) c4 ] may be the same or different from each other, when e1 is 2 or greater, two or more Z1 may be the same or different from each other, when e2 is 2 or greater, two or more Z2 may be the same or different from each other, when e3 is 2 or greater, two or more Z3 may be the same or different from each other, when e4 is 2 or greater, two or more Z4 may be the same or different from each other, when d1 is 2 or greater, two or more groups represented by *-[W1-(Z1) e1 ] may be the same as or different from each other. When d2 is 2 or greater, two or more groups represented by *-[W2-(Z2) e2 ] may be the same as or different from each other. When d3 is 2 or greater, two or more groups represented by *-[W3-(Z3) e3 ] may be the same as or different from each other, and when d4 is 2 or greater, two or more groups represented by *-[W4-(Z4) e1 ] may be the same as or different from each other. For example, in Formulas 1, 2-1, and 2-2, c1-c4, a1-a4, e1-e4, and d1-d4 may each independently be 0, 1, 2, or 3.
[0211] In the composition, the second compound is not tris[2-phenylpyridine]iridium.
[0212] In one or more embodiments, in Formula 2-1, the case where Y1 is N, ring A1 is a pyridine group, Y2 is C, ring A2 is a phenyl group, and d1 and d2 are each 0 may be excluded.
[0213] In Formulae 1, 2-1, and 2-2, at least two substituents from the following groups are each independently optionally linked to each other to form a group that is unsubstituted or substituted with at least one R 10a Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic group: i) two or more of multiple R1, ii) two or more of multiple R2, iii) two or more of multiple R3, iv) two or more of multiple R4, v) R 5a and R 5b , vi) two or more of a plurality of Z1, vii) two or more of a plurality of Z2, viii) two or more of a plurality of Z3, ix) two or more of a plurality of Z4, x) R1-R4, R 5a , and R 5b In other words, i) two or more of multiple R1, ii) two or more of multiple R2, iii) two or more of multiple R3, iv) two or more of multiple R4, v) R 5a and R 5b , vi) two or more of a plurality of Z1, vii) two or more of a plurality of Z2, viii) two or more of a plurality of Z3, ix) two or more of a plurality of Z4, x) R1-R4, R 5a , and R 5b and / or xi) two or more of Z1-Z4 are optionally linked to each other to form an unsubstituted or substituted group. 10a Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic group.
[0214] R 10a As defined for R1.
[0215] As used herein, the symbols * and *' each represent a binding site to an adjacent atom, unless otherwise specified. For example, in Formulas 2-1 and 2-2, * and *' each represent a binding site to M2.
[0216] In one or more embodiments, in Formula 1, n1 may not be 0, n4 may be 0, and The group represented may be a group represented by one of formulae CY1(1) to CY1(23):
[0217]
[0218] Wherein, in formulas CY1(1) to CY1(23),
[0219] X1 may be as defined herein,
[0220] X 19 Can be O, S, Se, N(R 19a )、C(R 19a )(R 19b ), or Si(R 19a )(R 19b ),
[0221] R 19a and R 19b may each be as defined for R1,
[0222] * represents the binding site with X5 in Formula 1, and
[0223] *' represents the difference between T and 11 binding site.
[0224] In one or more embodiments, in Formula 1, n1 may be 1, n4 may be 0, and The group represented may be a group represented by one of the formulae CY1-1 to CY1-18:
[0225]
[0226] Among them, in formulas CY1-1 to CY1-18,
[0227] X1 may be as defined herein,
[0228] R 11 -R 14 may each be as defined for R1, and R 11 -R 14 Each may not be hydrogen,
[0229] * represents the binding site with X5 in Formula 1, and
[0230] *' represents the difference between T and 11 binding site.
[0231] In one or more embodiments, in Formula 1, n1 and n2 may each be 1, and ring CY2 may be a group represented by formula CY2A or CY2B:
[0232]
[0233] Among them, in formulas CY2A and CY2B,
[0234] X2 and CY2 may each be as defined herein,
[0235] Y 91 -Y 93 can be independently O, S, N, C, or Si,
[0236] In formulas CY2A and CY2B, X2 and Y 91 The key between X2 and Y 92 The key between X2 and Y 93 The key between, and in Y 22 With Y 93 The bonds between them can each be chemical bonds,
[0237] *' represents the difference between T and 11 The binding site,
[0238] * indicates the binding site with M1 in Formula 1, and
[0239] *" indicates the difference between T and 12 binding site.
[0240] In one or more embodiments, in Formula 1, n1 and n2 may each be different from 0, and are given by The group represented may be a group represented by one of formulae CY2(1) to CY2(21):
[0241]
[0242]
[0243] Wherein, in formulas CY2(1) to CY2(21),
[0244] X2 may be as defined herein,
[0245] X 29 Can be O, S, N-[(L2) b2 -(R2) c2 ]、C(R 29a )(R 29b ), or Si(R 29a )(R 29b ),
[0246] L2, b2, R2, and c2 may each be as defined herein,
[0247] R 29a and R 29bmay each be as defined for R2,
[0248] *' represents the difference between T and 11 The binding site,
[0249] * indicates the binding site with M1 in Formula 1, and
[0250] *" indicates the difference between T and 12 binding site.
[0251] In one or more embodiments, in Formula 1, n1 and n2 may each be 1, and The group represented may be a group represented by one of formulae CY2-1 to CY2-16:
[0252]
[0253] Wherein, in formulas CY2-1 to CY2-16,
[0254] X2 may be as defined herein,
[0255] X 29 Can be O, S, N-[(L2) b2 -(R2) c2 ]、C(R 29a )(R 29b ), or Si(R 29a )(R 29b ),
[0256] L2, b2, R2, and c2 may each be as defined herein,
[0257] R 21 -R 23 、R 29a , and R 29b may each be as defined for R2, wherein R 21 -R 23 Each may not be hydrogen,
[0258] *' represents the difference between T and 11 The binding site,
[0259] * indicates the binding site with M1 in Formula 1, and
[0260] *" indicates the difference between T and 12 binding site.
[0261] In one or more embodiments, in Formula 1,
[0262] n1 and n2 can each be 1,
[0263] Depend on The group represented by the formula CY2-9 to CY2-16 can be a group represented by one of the formulas CY2-9 to CY2-16,
[0264] X in the formulas CY2-9 to CY2-16 29 may be N-[(L2) b2 -(R2) c2 ],
[0265] L2may be unsubstituted or substituted with at least one R 10a substituted phenyl group,
[0266] b2may be 1 or 2,
[0267] c2may be 1 or 2, and
[0268] when c2is 1, R2may be phenyl unsubstituted or substituted with deuterium, C1-C 20 alkyl, or combinations thereof; and when c2is 2, a) one of the two R2may be phenyl unsubstituted or substituted with deuterium, C1-C 20 alkyl, phenyl, deuterated phenyl, (C1-C 20 alkyl)phenyl, or combinations thereof, b) and the other R2may be C4-C 20 alkyl unsubstituted or substituted with C3-C 10 cycloalkyl, or deuterated C1-C 20 alkyl.
[0269] In one or more embodiments, in Formula 1, n2and n3may each be other than 0, and the group represented by may be a group represented by one of the formulas CY3(1) to CY3(15):
[0270]
[0271] wherein, in the formulas CY3(1) to CY3(15),
[0272] X3may be as defined herein,
[0273] X 39 may be O, S, N(Z 39a ), C(R 39a )(R 39b ), or Si(R 39a )(R 39b ),
[0274] R 39a and R 39b may each be as defined for R3,
[0275] *"represents the binding site to T 12 in Formula 1,
[0276] * indicates the binding site with M1 in Formula 1, and
[0277] *' represents the difference between T and 13 binding site.
[0278] In one or more embodiments, in Formula 1, n2 and n3 may each be 1, and The group represented may be a group represented by one of the formulae CY3-1 to CY3-13:
[0279]
[0280] Among them, in formulas CY3-1 to CY3-31,
[0281] X3 may be as defined herein,
[0282] X 39 Can be O, S, N-[(L3) b3 -(R3) c3 ]、C(R 39a )(R 39b ), or Si(R 39a )(R 39b ),
[0283] L3, b3, R3, and c3 may each be as defined herein,
[0284] R 31 -R 33 、R 39a , and R 39b may each be as defined for R3, wherein R 31 -R 33 Each may not be hydrogen,
[0285] *" indicates the difference between T and 12 The binding site,
[0286] * indicates the binding site with M1 in Formula 1, and
[0287] *' represents the difference between T and 13 binding site.
[0288] In one or more embodiments, in Formula 1, n3 may not be 0, n4 may be 0, and The group represented may be a group represented by one of formulae CY4(1) to CY4(20):
[0289]
[0290] Wherein, in formulas CY4(1) to CY4(20),
[0291] X4 may be as defined herein,
[0292] X 49 Can be O, S, N (R 49a )、C(R 49a )(R 49b ), or Si(R 49a )(R 49b ),
[0293] R 49a and R 49b may each be as defined for R4,
[0294] *' represents the difference between T and 13 binding sites, and
[0295] * indicates the binding site with M1 in Formula 1.
[0296] In one or more embodiments, in Formula 1, n3 may be 1, n4 may be 0, and The group represented may be a group represented by one of the formulae CY4-1 to CY4-16:
[0297]
[0298] Among them, in formulas CY4-1 to CY4-16,
[0299] X4 may be as defined herein,
[0300] R 41 -R 44 may each be as defined for R4, and R 41 -R 44 Each may not be hydrogen,
[0301] *' represents the difference between T and 13 binding sites, and
[0302] * indicates the binding site with M1 in Formula 1.
[0303] In one or more embodiments, the first compound may be a compound represented by one of Formulas 1-1 to 1-3:
[0304]
[0305]
[0306] Among them, in formulas 1-1 to 1-3,
[0307] M1, X1-X5, T 12 , and T 13 may each be as defined herein,
[0308] X 11 may be N or C(R 11 ), X 12 may be N or C(R 12 ), X 13 may be N or C(R 13 ), and X 14 may be N or C(R 14 ),
[0309] R 11 -R 14 may each be as defined for R1,
[0310] R 11 -R 14 two or more of which can optionally be linked to each other to form a C5-C 10a carbocyclic group which is unsubstituted or substituted by at least one R 30 C1-C 10a heterocyclic group which is unsubstituted or substituted by at least one R 30 ,
[0311] X 21 may be N or C(R 21 ), X 22 may be N or C(R 22 ), and X 23 may be N or C(R 23 ),
[0312] X 29 may be O, S, N-[(L2) b2 -(R2) c2 ], C(R 29a )(R 29b ), or Si(R 29a )(R 29b ),
[0313] L2, b2, R2, and c2may each be as defined herein,
[0314] R 21 -R 23 , R 29a , and R 29b may each be as defined for R2,
[0315] R 21 -R 23 two or more of which can optionally be linked to each other to form a C5-C 10aSubstituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups,
[0316] X 31 Can be N or C(R 31 ), X 32 Can be N or C(R 32 ), and X 33 Can be N or C(R 33 ),
[0317] R 31 -R 33 may each be as defined for R3,
[0318] R 31 -R 33 Two or more of may be optionally linked to each other to form an unsubstituted or substituted group consisting of at least one R 10a Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups,
[0319] X 41 Can be N or C(R 41 ), X 42 Can be N or C(R 42 ), X 43 Can be N or C(R 43 ), and X 44 Can be N or C(R 44 ),
[0320] R 41 -R 44 may each be as defined for R4, and
[0321] R 41 -R 44 Two or more of may be optionally linked to each other to form an unsubstituted or substituted group consisting of at least one R 10a Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups,
[0322] R 10a May be as defined for R1.
[0323] In one or more embodiments,
[0324] Y1 in formula 2-1 can be N, and
[0325] In formula 2-1, The group represented may be a group represented by one of formulae A1-1 to A1-3:
[0326]
[0327] Wherein, in formulas A1-1 to A1-3,
[0328] Z 11 -Z 14 can each be as defined for Z1,
[0329] R 10a As mentioned above about R 10a As defined,
[0330] a14 can be an integer from 0 to 4.
[0331] a18 can be an integer from 0 to 8.
[0332] *' represents the binding site with M2 in Formula 2, and
[0333] *" indicates the binding site to ring A2.
[0334] For example, in formulas A1-1 to A1-3, Z 14 Can be deuterated C1-C 20 Alkyl, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5).
[0335] In one or more embodiments,
[0336] Y3 in formula 2-2 may be N, and
[0337] In formula 2-2, The group represented may be a group represented by one of the formulae NR1 to NR48:
[0338]
[0339]
[0340] Wherein, in formulas NR1 to NR48,
[0341] Y 39 Can be O, S, Se, N-[W3-(Z3) e3 ]、C(Z 39a )(Z 39b ), or Si(Z 39a )(Z 39b ),
[0342] W3, Z3, and e3 may each be as defined herein, and Z 39a and Z 39b can each be as defined for Z3,
[0343] *' represents the binding site with M2 in Formula 2, and
[0344] *" indicates the binding site to loop A4.
[0345] In one or more embodiments,
[0346] In formulae 2-1 and 2-2, Y2 and Y4 may each be C, and
[0347] In formula 2-1, 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:
[0348]
[0349]
[0350] Among them, in CR1 to CR29,
[0351] Y 49 Can be O, S, Se, N-[W2-(Z2) e2 ]、N-[W4-(Z4) e4 ]、C(Z 29a )(Z 29b )、C(Z 49a )(Z 49b )、Si(Z 29a )(Z 29b ), or Si(Z 49a )(Z 49b ),
[0352] W2, W4, Z2, Z4, e2, and e4 may each be as defined herein, Z 29a and Z 29b can each be as defined for Z2, and Z 49a and Z 49b can each be as defined for Z4,
[0353] Y 21 -Y 24 can be independently N or C,
[0354] Ring A 40 Can be C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic groups (e.g., A40 may be a benzene group, a naphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, or a benzoquinazoline group),
[0355] * indicates the binding site with M2 in Formula 2, and
[0356] *" represents the binding site to Ring A1 in Formula 2-1 or Ring A3 in Formula 2-2.
[0357] In one or more embodiments,
[0358] 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):
[0359]
[0360] Wherein, in formulas CR(1) to CR(13),
[0361] Y 49 may be as defined herein, and
[0362] Y 31 -Y 34 and Y 41 -Y 48 can each independently be C or N.
[0363] In one or more embodiments, the first compound may include at least one deuterium.
[0364] In one or more embodiments, the second compound may include at least one deuterium.
[0365] The first compound may emit a first light having a first spectrum, and λP1 (may also be referred to as λP(Pt)) represents an emission peak wavelength (nm) in the first spectrum.
[0366] The second compound may emit a second light having a second spectrum, and λP2 (may also be referred to as λP(Ir)) represents an emission peak wavelength (nm) in the second spectrum.
[0367] Here, λP1 and λP2 can be evaluated from a photoluminescence spectrum measured for each of the first film and the second film.
[0368] As used herein, the term "first film" refers to a film comprising the first compound, and the term "second film" refers to a film comprising the second compound. The first and second films can be manufactured using various methods, such as vacuum deposition, coating, or heating. The first and second films may further include a compound different from the first and second compounds, such as a host as defined herein.
[0369] In one or more embodiments, λP1 and λP2 may each be within a range of about 480 nanometers (nm) to about 580 nm, or about 510 nm to about 570 nm.
[0370] In one or more embodiments, the absolute value of the difference between λP1 and λP2 may be in a range of about 0 nm to about 30 nm, about 0 nm to about 20 nm, or about 0 nm to about 10 nm.
[0371] In one or more embodiments, the first light and the second light may each be green light.
[0372] In one or more embodiments, the first light may be green light, and the second light may be yellow-green light.
[0373] In one or more embodiments, each of the first light and the second light may be yellow-green light.
[0374] In one or more embodiments, the first light may be yellow-green light, and the second light may be yellow light.
[0375] In one or more embodiments, the first light and the second light may each be yellow light.
[0376] For example, the first compound may be one or more compounds of Group 1-1 to Group 1-4:
[0377] Group 1-1
[0378]
[0379]
[0380]
[0381]
[0382]
[0383]
[0384]
[0385]
[0386]
[0387]
[0388]
[0389]
[0390]
[0391]
[0392]
[0393]
[0394]
[0395]
[0396]
[0397]
[0398]
[0399]
[0400]
[0401]
[0402]
[0403]
[0404]
[0405]
[0406]
[0407]
[0408]
[0409] Group 1-2
[0410]
[0411]
[0412]
[0413]
[0414]
[0415]
[0416]
[0417]
[0418]
[0419]
[0420]
[0421]
[0422]
[0423]
[0424]
[0425]
[0426]
[0427]
[0428]
[0429]
[0430]
[0431]
[0432]
[0433]
[0434]
[0435]
[0436]
[0437]
[0438]
[0439]
[0440]
[0441]
[0442]
[0443]
[0444]
[0445]
[0446]
[0447]
[0448]
[0449]
[0450]
[0451]
[0452]
[0453]
[0454]
[0455]
[0456]
[0457]
[0458]
[0459]
[0460]
[0461]
[0462]
[0463]
[0464]
[0465]
[0466]
[0467]
[0468]
[0469]
[0470]
[0471]
[0472]
[0473]
[0474]
[0475]
[0476]
[0477]
[0478]
[0479]
[0480]
[0481]
[0482]
[0483]
[0484]
[0485]
[0486]
[0487]
[0488]
[0489]
[0490]
[0491]
[0492]
[0493]
[0494]
[0495]
[0496]
[0497]
[0498]
[0499]
[0500]
[0501]
[0502]
[0503]
[0504]
[0505]
[0506]
[0507]
[0508]
[0509]
[0510]
[0511]
[0512]
[0513]
[0514]
[0515]
[0516]
[0517]
[0518]
[0519]
[0520]
[0521]
[0522]
[0523]
[0524]
[0525]
[0526]
[0527]
[0528]
[0529]
[0530]
[0531]
[0532]
[0533]
[0534]
[0535]
[0536]
[0537]
[0538]
[0539]
[0540]
[0541]
[0542]
[0543]
[0544]
[0545]
[0546]
[0547]
[0548]
[0549]
[0550]
[0551]
[0552]
[0553]
[0554]
[0555]
[0556]
[0557]
[0558]
[0559]
[0560]
[0561] Group 1-3
[0562]
[0563]
[0564]
[0565]
[0566]
[0567]
[0568] Group 1-4
[0569]
[0570] For example, the second compound can be one or more compounds of Group 2-1 to Group 2-5:
[0571] Group 2-1
[0572]
[0573]
[0574]
[0575]
[0576]
[0577]
[0578]
[0579]
[0580]
[0581]
[0582]
[0583]
[0584]
[0585]
[0586]
[0587]
[0588]
[0589]
[0590]
[0591]
[0592]
[0593]
[0594]
[0595]
[0596]
[0597]
[0598]
[0599]
[0600]
[0601]
[0602]
[0603]
[0604]
[0605]
[0606]
[0607]
[0608]
[0609]
[0610]
[0611]
[0612]
[0613]
[0614]
[0615]
[0616]
[0617]
[0618]
[0619]
[0620]
[0621]
[0622]
[0623]
[0624]
[0625]
[0626]
[0627]
[0628]
[0629]
[0630]
[0631]
[0632]
[0633]
[0634]
[0635]
[0636]
[0637]
[0638]
[0639]
[0640]
[0641]
[0642]
[0643]
[0644] Group 2-2
[0645]
[0646]
[0647]
[0648]
[0649]
[0650]
[0651]
[0652]
[0653]
[0654]
[0655]
[0656]
[0657]
[0658]
[0659]
[0660]
[0661]
[0662]
[0663]
[0664]
[0665]
[0666]
[0667]
[0668]
[0669]
[0670]
[0671]
[0672]
[0673]
[0674]
[0675]
[0676]
[0677]
[0678]
[0679]
[0680]
[0681]
[0682]
[0683]
[0684]
[0685]
[0686] Group 2-3
[0687]
[0688]
[0689]
[0690]
[0691] Group 2-4
[0692]
[0693]
[0694]
[0695]
[0696]
[0697]
[0698]
[0699] Groups 2-5
[0700]
[0701] As used in the formulas and structures herein, and unless otherwise specified to the contrary, "Ome" is methoxy, "TMS" is trimethylsilyl, and "TMG" is trimethylgermyl.
[0702] The composition comprising the first compound represented by Formula 1 and the second compound represented by Formula 2 as defined above can emit light having excellent luminous efficiency and lifespan (e.g., light having an emission peak wavelength in the range of about 480 nm to about 580 nm or about 510 nm to about 570 nm, such as green light, yellow-green light, or yellow light). Thus, a layer comprising the composition, a light-emitting device comprising the composition, and an electronic device comprising the light-emitting device can be provided.
[0703] Another aspect of the present disclosure provides a layer including the composition comprising the first compound and the second compound.
[0704] In one or more embodiments, the layer may emit light having an emission peak wavelength in a range of about 480 nm to about 580 nm, for example, about 510 nm to about 570 nm.
[0705] In one or more embodiments, the layer may emit green light, yellow-green light, or yellow light.
[0706] In one or more embodiments, the layer may emit light having an emission peak wavelength in a range of about 510 nm to about 540 nm.
[0707] In one or more embodiments, the layer may emit light having an emission peak wavelength in a range of about 540 nm to about 570 nm.
[0708] In one or more embodiments, the weight ratio of the first compound to the second compound included in the layer may be in a range of about 90:10 to about 10:90, about 80:20 to about 20:80, about 70:30 to about 30:70, or about 60:40 to about 40:60.
[0709] In one or more embodiments, the first compound and the second compound may be included in the layer in a weight ratio of about 50:50, ie, about 1:1.
[0710] In one or more embodiments, the layer may be formed by i) co-depositing the first compound and the second compound, or ii) using a first mixture including the first compound and the second compound.
[0711] In one or more embodiments, the layer may include a host and a dopant, wherein the host does not include a transition metal and the dopant may include the composition comprising the first compound and the second compound. In one or more embodiments, the layer may be formed by: i) co-depositing the host and the dopant, or ii) using a second mixture comprising the host and the dopant.
[0712] In the layer, the amount (eg, weight) of the host may be greater than the amount (eg, weight) of the dopant.
[0713] For example, a weight ratio of the host to the dopant in the layer may be in a range of about 99:1 to about 55:45, about 97:3 to about 60:40, or about 95:5 to about 70:30.
[0714] The host in the layer may include a hole transport compound, an electron transport compound, a bipolar compound, or a combination thereof.
[0715] Another aspect of the present disclosure provides a light emitting device including: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes the composition including the first compound and the second compound.
[0716] By including the composition including the first compound and the second compound as defined above, the light emitting device may have excellent driving voltage, excellent external quantum efficiency, and excellent lifespan characteristics.
[0717] In one or more embodiments, the emission layer included in the organic layer of the light emitting device may include the composition including the first compound and the second compound.
[0718] In one or more embodiments, the emission layer may include a host and a dopant, wherein the host may not include a transition metal, and the dopant may include the composition.
[0719] The host included in the emission layer may include a hole transport compound, an electron transport compound, a bipolar compound, or a combination thereof.
[0720] For example, the host may include a hole transport compound and an electron transport compound, wherein the hole transport compound and the electron transport compound may be different from each other.
[0721] The emissive layer may be formed by i) co-depositing the host and the dopant, or ii) using a second mixture including the host and the dopant.
[0722] The emission layer may emit a third light having a third spectrum, and λP(EML) represents an emission peak wavelength (nm) in the third spectrum. For example, λP(EML) may be evaluated from an electroluminescence (EL) spectrum of the light emitting device.
[0723] The light-emitting device (organic light-emitting device) may emit a fourth type of light having a fourth spectrum that is extracted to the outside of the light-emitting device through the first electrode and / or the second electrode of the light-emitting device, and λP(OLED) represents an emission peak wavelength (nm) in the fourth spectrum. For example, λP(OLED) can be evaluated based on the electroluminescence spectrum of the light-emitting device.
[0724] For example, λP(EML) and λP(OLED) may each independently be in a range of about 480 nm to about 580 nm, such as about 510 nm to about 570 nm.
[0725] In one or more embodiments, λP(EML) and λP(OLED) may each independently be in a range of about 510 nm to about 540 nm.
[0726] In one or more embodiments, λP(EML) and λP(OLED) may each independently be in a range of about 540 nm to about 570 nm.
[0727] In one or more embodiments, the third light and the fourth light may each be green light, yellow-green light, or yellow light.
[0728] In one or more embodiments, each of the third light and the fourth light may not be white light.
[0729] In one or more embodiments, with respect to the third spectrum, i) may include a main emission peak having λP(EML); but ii) may not include an additional emission peak having an emission peak wavelength of (λP(EML)+50nm) or greater or (λP(EML)-50nm) or less.
[0730] In one or more embodiments, the third spectrum may i) include a main emission peak having λP(EML); but ii) may not include additional emission peaks having emission peak wavelengths in the red and / or blue regions.
[0731] In one or more embodiments, regarding the fourth spectrum, i) may include a main emission peak having λP(OLED); but ii) may not include an additional emission peak having an emission peak wavelength of (λP(OLED)+50nm) or greater or (λP(OLED)-50nm) or less.
[0732] In one or more embodiments, the fourth spectrum may i) include a main emission peak having λP(EML); but ii) may not include additional emission peaks having emission peak wavelengths in the red and / or blue regions.
[0733] The first electrode may be an anode as a hole injection electrode, and the second electrode may be a cathode as an electron injection electrode; or the first electrode may be a cathode as an electron injection electrode, and the second electrode may be an anode as a hole injection electrode.
[0734] For example, in the light-emitting device, the first electrode may be an anode, and the second electrode may be a cathode, and the organic layer may further include a hole transport region arranged between the first electrode and the emission layer, and an electron transport region arranged between the emission layer and the second electrode, wherein 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.
[0735] As used herein, the term "organic layer" refers to a single layer or a plurality of layers disposed between the first electrode and the second electrode of the light emitting device. The "organic layer" may include an organic metal complex including a metal in addition to an organic compound.
[0736] Figure 1 FIG. 1 is a schematic cross-sectional view of a light emitting device 10 according to one or more embodiments. Figure 1The structure and manufacturing method of the light emitting device according to one or more embodiments of the present disclosure are described.The light emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked in the order of the statements.
[0737] A substrate may be further disposed under the first electrode 11 or over the second electrode 19. As the substrate, any substrate used in light-emitting devices in the related art may be used, and the substrate may be a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and / or water resistance.
[0738] The first electrode 11 may be formed, for example, by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may include a material having a high work function to promote hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In one or more embodiments, the material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 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).
[0739] The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO.
[0740] The organic layer 15 is disposed on the first electrode 11 .
[0741] The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.
[0742] The hole transport region may be disposed between the first electrode 11 and the emission layer.
[0743] 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.
[0744] The hole transport region may include only a hole injection layer or a hole transport layer. The hole transport region may have a hole injection layer / hole transport layer structure or a hole injection layer / hole transport layer / electron blocking layer structure, wherein for each structure, the constituent layers are sequentially stacked in the order stated starting from the first electrode 11.
[0745] When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods such as vacuum deposition, spin coating, casting, and / or Langmuir-Blodgett (LB) deposition.
[0746] 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 in the range of about 100° C. to about 500° C., ... -8 Torr - about 10 -3 The vacuum pressure is within the range of Torr, and the -about The deposition rate is within the range of .
[0747] 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 in the range of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and a heat treatment temperature in the range of about 80° C. to about 200° C. for removing the solvent after coating.
[0748] Conditions for forming the hole transport layer and the electron blocking layer may be the same as conditions for forming the hole injection layer.
[0749] The hole transport region may include 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(naphth-1-yl)-N,N′-diphenyl-benzidine (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″-tris(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:
[0750]
[0751] Formula 201
[0752]
[0753] Formula 202
[0754]
[0755] In formula 201, Ar 101 and Ar 102 Each of them may be independently unsubstituted or substituted by at least one of the following: phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, acenaphthenylene, fluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyren ...benzo[9,10]phenanthrenylene, pyrenylene, acenaphthenylene, fluorenylene, phenanthrenylene, anthracenylene, fluorenylene, benzo[9,10]phenanthrenylene phenylene, tetraphenylene, perylene, perylene, or pentacene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C10 Cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkyl, 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 a heteroarylthio group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or a combination thereof.
[0756] In Formula 201, xa and xb may each independently be an integer of 0 to 5, or may be 0, 1, or 2. For example, in Formula 201, xa may be 1, and xb may be 0.
[0757] In Equations 201 and 202, R 101 -R 108 、R 111 -R 119 , and R 121 -R 124 Can be independently:
[0758] hydrogen, deuterium, -F, -Cl, -Br, -I, 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 10 Alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), C1-C 10 Alkoxy (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.), or C1-C 10 alkylthio;
[0759] C1-C 10 Alkyl, C1-C 10 Alkoxy, or C1-C 10 Alkylthio: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, or a combination thereof; or
[0760] phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl, each of which is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 10 Alkyl, C1-C 10 Alkoxy, C1-C 10 alkylthio, or a combination thereof.
[0761] In formula 201, R 109 The phenyl, naphthyl, anthracenyl, or pyridyl groups may be unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 alkylthio, phenyl, naphthyl, anthracenyl, pyridyl, or a combination thereof.
[0762] In one or more embodiments, the compound represented by Formula 201 can be represented by Formula 201A:
[0763] Formula 201A
[0764]
[0765] Wherein, in Formula 201A, R 101 、R 111 、R 112 , and R 109 may each be as defined herein.
[0766] For example, the hole transport region may include one or more of compounds HT1 to HT20:
[0767]
[0768]
[0769] The thickness of the hole transport region may be about -about For example, about -about When the hole transport region 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 -about For example, about -about and the thickness of the hole transport layer may be in the range of about -about For example, about -about When the thicknesses of the hole transport region, 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.
[0770] In addition to these materials, the hole transport region may further include a charge generating material to improve the conductive properties. The charge generating material may be dispersed uniformly or non-uniformly in the hole transport region.
[0771] 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 be: a quinone derivative such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ), F6-TCNNQ, etc.; a metal oxide such as tungsten oxide, molybdenum oxide, etc.; a compound containing a cyano group such as compound HT-D1, etc.; or a combination thereof:
[0772]
[0773] The hole transport region may further include a buffer layer.
[0774] 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 a formed light emitting device may be improved.
[0775] Meanwhile, when the hole transport region includes an electron blocking layer, the material used to form the electron blocking layer may include the material used in the hole transport region as defined above, the host material defined below, or a combination thereof. For example, when the hole transport region includes an electron blocking layer, the material used to form the electron blocking layer may include mCP defined below, compounds H-H1 defined below, or a combination thereof.
[0776] Then, the emission layer 15 may be formed on the hole transport region by using a method such as vacuum deposition, spin coating, casting, LB deposition, etc. When the emission layer 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 layer.
[0777] In one or more embodiments, the emission layer may include the composition including the first compound represented by Formula 1 as defined herein and the second compound represented by Formula 2. In one or more embodiments, the emission layer may include a layer including the composition including the first compound represented by Formula 1 as defined herein and the second compound represented by Formula 2.
[0778] In one or more embodiments, the emission layer may include a host and a dopant, wherein the host does not include a transition metal and the dopant includes the composition including the first compound represented by Formula 1 and the second compound represented by Formula 2 as defined herein.
[0779] The host may include 1,3,5-tris(1-phenyl-1H-benzo[d]imidazolyl-2-yl)benzene (TPBi), 3-tert-butyl-9,10-di(naphthalen-2-yl)anthracene (TBADN), 9,10-di(naphthalen-2-yl)anthracene (AND, also known as "DNA"), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), TCP, mCP, Compound H50, Compound H51, Compound H52, Compound H-H1, Compound H-H2, or a combination thereof:
[0780]
[0781]
[0782] When the light emitting device is a full-color light emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and / or a blue emission layer.
[0783] The thickness of the emission layer may be about -about For example, about -about When the thickness of the emission layer is within these ranges, excellent light emitting characteristics can be obtained without a significant increase in driving voltage.
[0784] Next, the electron transport region may be disposed on the emission layer.
[0785] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
[0786] For example, the electron transport region may have a hole blocking layer / electron transport layer / electron injection 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.
[0787] Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer constituting the electron transport region can be understood by referring to the conditions for forming the hole injection layer.
[0788] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), bis(2-methyl-8-hydroxyquinolinolato-N1,O8)-(1,1′-biphenyl-4-hydroxy)aluminum (Balq), or a combination thereof:
[0789]
[0790] The thickness of the hole blocking layer may be about -about For example, about -about When the thickness of the hole blocking layer is within these ranges, excellent hole blocking properties may be obtained without a significant increase in driving voltage.
[0791] In one or more embodiments, the electron transport layer may include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), Bphen, TPBi, tris(8-hydroxyquinoline)aluminum (Alq3), 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:
[0792]
[0793] In one or more embodiments, the electron transport layer may include one or more of compounds ET1 to ET25:
[0794]
[0795]
[0796] The thickness of the electron transport layer can be about -about For example, about -about When the thickness of the electron transport layer is within these ranges, satisfactory electron transport characteristics may be obtained without a significant increase in driving voltage.
[0797] In addition to the materials defined above, the electron transport layer may further include a metal-containing material.
[0798] The metal-containing material can include a Li complex. The Li complex can include, for example, compound ET-D1 or ET-D2:
[0799]
[0800] The electron transport region can further include an electron injection layer that facilitates the flow of electrons from the second electrode 19 thereinto.
[0801] The electron injection layer can include LiF, NaCl, CsF, Li2O, BaO, compound ET-D1, compound ET-D2, or a combination thereof.
[0802] The thickness of the electron injection layer can be in a range from about 0.1 nm to about 10 nm, for example. - about 1 nm and, for example, about 5 nm. - about 1 nm - about 1 nm When the thickness of the electron injection layer is in these ranges, satisfactory electron injection properties can be obtained without a significant increase in driving voltage.
[0803] The second electrode 19 can be disposed on the organic layer 15. The second electrode 19 can be a cathode. The material used to form the second electrode 19 can be a metal, an alloy, a conductive compound, or a combination thereof, having a relatively low work function. For example, the material used to form the second electrode 19 can be Li, Mg, Al, Ag, Al-Li, Ca, Mg-In, Mg-Ag, or the like. In order to manufacture a top emission type light emitting device, various modifications are possible, and, for example, a transmissive electrode formed using ITO or IZO can be used as the second electrode 19.
[0804] In the foregoing, the light emitting device 10 according to one or more embodiments has been described in conjunction with Figure 1 However, the one or more embodiments of the present disclosure are not limited thereto.
[0805] For example, the light emitting device can be included in an electronic device. Accordingly, another aspect of the present disclosure provides an electronic device including the light emitting device. The electronic device can include, for example, a display, a lighting device, a sensor, or the like.
[0806] As used herein, the term "C1-C 60 alkyl" refers to a straight-chain or branched saturated aliphatic hydrocarbon monovalent radical of from 1 to 60 carbon atoms, and as used herein, the term "C1-C 60 alkylene" refers to a divalent radical having the same structure as a C1-C 60 alkyl.
[0807] C1-C 60 alkyl, C1-C20 alkyl, and / or C1-C 10 Examples of alkyl groups are methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, t-pentyl, neopentyl, i-pentyl, sec-pentyl, 3-pentyl, sec-i-pentyl, n-hexyl, i-hexyl, sec-hexyl, t-hexyl, n-heptyl, i-heptyl, sec-heptyl, t-heptyl, n-octyl, i-octyl, sec-octyl, t-octyl, n-nonyl, i-nonyl, sec-nonyl, t-nonyl, n-decyl, i-decyl, sec-decyl, or t-decyl, each unsubstituted or substituted with methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, t-pentyl, neopentyl, i-pentyl, sec-pentyl, 3-pentyl, sec-i-pentyl, n-hexyl, i-hexyl, sec-hexyl, t-hexyl, n-heptyl, i-heptyl, sec-heptyl, t-heptyl, n-octyl, i-octyl, sec-octyl, t-octyl, n-nonyl, i-nonyl, sec-nonyl, t-nonyl, n-decyl, i-decyl, sec-decyl, t-decyl, or combinations thereof. For example, formula 9-33 is a branched C6alkyl group, and examples thereof are t-butyl substituted with two methyl groups.
[0808] The term "C1-C 60 alkoxy" as used herein refers to a monovalent radical represented by -OA 101 (wherein A 101 is C1-C 60 alkyl), and examples thereof are methoxy, ethoxy, propoxy, butoxy, and pentoxy.
[0809] The term "C1-C 60 alkylthio" as used herein refers to a monovalent radical represented by -OA 101 (wherein A 101 is C1-C 60 alkyl).
[0810] The term "C2-C 60 alkenyl" as used herein refers to a hydrocarbon radical formed by the insertion of at least one carbon-carbon double bond into a C2-C 60 alkyl group, and examples thereof are ethenyl, propenyl, and butenyl. The term "C2-C 60 alkenylene" as used herein refers to a divalent radical having the same structure as a C2-C 60 alkenyl group.
[0811] The term "C2-C 60 alkynyl" as used herein refers to a hydrocarbon radical formed by the insertion of at least one carbon-carbon triple bond into a C2-C 60 alkyl group, and examples thereof are ethynyl and propynyl. The term "C2-C 60"Alkynylidene" refers to a C2-C 60 Alkynyl is a divalent group of the same structure.
[0812] As used herein, the term "C3-C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and the term "C3-C 10 "Cycloalkylene" refers to a group having a C3-C 10 Cycloalkyl is a divalent group of the same structure.
[0813] C3-C 10 Examples of cycloalkyl groups are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, and bicyclo[2.2.2]octyl.
[0814] As used herein, the term "C1-C 10 "Heterocycloalkyl" refers to a saturated monovalent cyclic group comprising at least one heteroatom selected from N, O, P, Si, S, Se, Ge and B as a ring atom and comprising 1 to 10 carbon atoms as ring atoms, and the term "C1-C 10 "Heterocycloalkylene" refers to a 10 Heterocycloalkyl is a divalent group of the same structure.
[0815] C1-C 10 Examples of heterocycloalkyl groups are silacyclopentyl, silacyclohexyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, and tetrahydrothienyl.
[0816] As used herein, the term "C3-C 10 "Cycloalkenyl" refers to a monovalent monocyclic group including 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and having no aromaticity, and examples thereof are cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C 10 "Cycloalkenylene" refers to a group having a C3-C 10 Cycloalkenyl is a divalent group of the same structure.
[0817] As used herein, the term "C1-C 10 "Heterocycloalkenyl" refers to a monovalent monocyclic group comprising 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 carbon-carbon double bond in its ring. 10 Examples of heterocycloalkenyl groups are 2,3-dihydrofuranyl and 2,3-dihydrothienyl.10 "Heterocycloalkenylene" refers to a group having a C1-C 10 Heterocycloalkenyl is a divalent group of the same structure.
[0818] As used herein, the term "C6-C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term "C6-C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. 60 Examples of aryl groups are phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and When C6-C 60 Aryl and C6-C 60 When the arylene groups each include two or more rings, the rings may be fused to each other.
[0819] As used herein, the term "C7-C 60 "Alkylaryl" refers to a group consisting of at least one C1-C 54 Alkyl-substituted C6-C 59 Aryl, and as used herein the term "C7-C 60 "Arylalkyl" refers to a group consisting of at least one C6-C 59 Aryl-substituted C1-C 54 alkyl.
[0820] As used herein, the term "C1-C 60 "Heteroaryl" refers to a monovalent group comprising at least one heteroatom selected from N, O, P, Si, S, Se, Ge and B as a ring-forming atom in a cyclic aromatic system having 1 to 60 carbon atoms, and the term "C1-C 60 "Heteroarylene" refers to a divalent group comprising at least one heteroatom selected from N, O, P, Si, S, Se, Ge and B as a ring atom in a cyclic aromatic system having 1 to 60 carbon atoms. 60 Examples of heteroaryl groups are pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. 60 Heteroaryl and C1-C 60 When the heteroarylene groups each include two or more rings, the rings may be fused to each other.
[0821] As used herein, the term "C2-C 60 "Alkylheteroaryl" refers to a group consisting of at least one C1-C 59 Alkyl-substituted C1-C 59 Heteroaryl. As used herein, the term "C2-C 59 "Heteroarylalkyl" refers to a group consisting of at least one C1-C59 Heteroaryl-substituted C1-C 59 alkyl.
[0822] As used herein, the term "C6-C 60 "Aryloxy" means -OA 102 (where A 102 C6-C 60 Aryl), such as the term "C6-C 60 "Arylthio" means -SA 103 (where A 103 C6-C 60 aryl), and as used herein the term "C1-C 60 "Alkylthio" means -SA 104 (where A 104 C1-C 60 alkyl).
[0823] As used herein, the term "C1-C 60 "Heteroaryloxy" means -OA 102’ (where A 102’ C1-C 60 heteroaryl), and as used herein, the term "C1-C 60 "Heteroarylthio" means -SA 103’ (where A 103’ C1-C 60 heteroaryl).
[0824] As used herein, the term "monovalent non-aromatic fused polycyclic group" refers to a monovalent group (e.g., 8-60 carbon atoms) having two or more rings fused to each other, having only carbon atoms as ring atoms, and not having aromaticity in its entire molecular structure. An example of a monovalent non-aromatic fused polycyclic group is a fluorenyl group. As used herein, the term "divalent non-aromatic fused polycyclic group" refers to a divalent group having the same structure as a monovalent non-aromatic fused polycyclic group.
[0825] As used herein, the term "monovalent non-aromatic fused heteropolycyclic group" 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 not having aromaticity in its entire molecular structure. An example of a monovalent non-aromatic fused heteropolycyclic group is a carbazolyl group. As used herein, the term "divalent non-aromatic fused heteropolycyclic group" refers to a divalent group having the same structure as a monovalent non-aromatic fused heteropolycyclic group.
[0826] As used herein, the term "C5-C 30A "carbocyclic group" refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring atoms. 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) C5-C 30 Examples of "carbocyclic groups" are (each unsubstituted or substituted by 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, 1,2,3,4-tetrahydronaphthalene group, cyclopentadiene group, and fluorene group.
[0827] As used herein, the term "C1-C 30 The term "heterocyclic group" refers to a saturated or unsaturated cyclic group having at least one heteroatom selected from N, O, P, Si, S, Se, Ge and B as a ring atom in a ring system having 1 to 30 carbon atoms. 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 Substituted) C1-C 30 Examples of "heterocyclic groups" are (each unsubstituted or substituted by at least one R 10aa substituted) thiophene group, a furan group, a pyrrole group, a silole group, a borol group, a phospholene group, a selenophene group, a germole group, a benzothiophene group, a benzofuran group, an indole group, a benzosilole group, a benzo phospholene group, a benzo selenophene group, a benzo germole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzosilole group, a dibenzophospholene group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azacarbazole group, an azabenzofuran group, an azaindole group, an azainden group, an azabenzosilole group, an azabenzophospholene group, an azabenzoselenophene group, an azabenzogermole group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azaf luorene group, an azadibenzosilole group, an azadibenzophospholene group, an azadibenzoselenophene group, an azadibenzogermole group, an azadibenzothiophene 5-oxide group, an azo-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide 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 phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an is oxazole group, a thiazole group, an isothiazole group, diazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benz oxazole group, a benzothiazole group, a benz diazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
[0828] “C5-C 30 carbon ring group” and “C1-C 30 hetero ring group” as used herein are i) a first ring, ii) a second ring, iii) a fused ring in which two or more first rings are fused to each other, iv) a fused ring in which two or more second rings are fused to each other, or v) a fused ring in which at least one first ring and at least one second ring are fused to each other,
[0829] wherein the first ring is a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a silole group, a borol group, a phospholene group, a germole group, a selenophene group, oxazole group, oxadiazole group, a triazole 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
[0830] The second 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.
[0831] The term "fluorinated C1-C 60 Alkyl (or fluorinated C1-C 20 Alkyl, etc.)", "Fluorinated C3-C 10 Cycloalkyl", "fluorinated C1-C 10 "Heterocycloalkyl" and "fluorinated phenyl" refer to C1-C 60 Alkyl (or C1-C 20 Alkyl, etc.), C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, and phenyl. For example, the term "fluorinated C1 alkyl (i.e., fluorinated methyl)" includes -CF3, -CF2H, and -CFH2. "Fluorinated C1-C 60 Alkyl (or fluorinated C1-C 20 Alkyl, etc.)", "Fluorinated C3-C 10 Cycloalkyl", "fluorinated C1-C 10 "Heterocycloalkyl" or "fluorinated phenyl" may be i) a fully fluorinated C1-C 60 Alkyl (or fully fluorinated C1-C 20 alkyl, etc.), fully fluorinated C3-C 10 Cycloalkyl, fully fluorinated C1-C 10 heterocycloalkyl, or fully fluorinated phenyl, wherein, in each group, all hydrogens included therein are replaced by fluorine groups, or ii) partially fluorinated C1-C 60 Alkyl (or partially fluorinated C1-C 20 alkyl, etc.), partially fluorinated C3-C 10 Cycloalkyl, partially fluorinated C1-C 10 Heterocycloalkyl, or partially fluorinated phenyl, wherein not all hydrogens included in each group are replaced by fluorine groups.
[0832] The term "deuterated C1-C 60 Alkyl (or deuterated C1-C 20 Alkyl, etc.)", "deuterated C3-C 10 Cycloalkyl", "deuterated C1-C 10"Heterocycloalkyl" and "deuterated phenyl" refer to C1-C 60 Alkyl (or C1-C 20 Alkyl, etc.), C3-C 10 Cycloalkyl, C1-C 10 For example, "deuterated C1 alkyl (i.e., deuterated methyl)" may include -CD3, -CD2H, and -CDH2, and "deuterated C3-C 10 Examples of "cycloalkyl" are formula 10-501, etc. ". Deuterated C1-C 60 Alkyl (or deuterated C1-C 20 Alkyl, etc.)", "deuterated C3-C 10 Cycloalkyl", "deuterated C1-C 10 Heterocycloalkyl" and "deuterated phenyl" may be i) a fully deuterated C1-C 60 Alkyl (or fully deuterated C1-C 20 alkyl, etc.), fully deuterated C3-C 10 Cycloalkyl, fully deuterated C1-C 10 heterocycloalkyl, or fully deuterated phenyl, wherein, in each group, all hydrogens included therein are replaced by deuterium, or ii) partially deuterated C1-C 60 Alkyl (or partially deuterated C1-C 20 alkyl, etc.), partially deuterated C3-C 10 Cycloalkyl, partially deuterated C1-C 10 heterocycloalkyl, or partially deuterated phenyl, wherein not all hydrogen atoms contained therein are replaced by deuterium in each group.
[0833] As used herein, the term "(C1-C 20 Alkyl) 'X' group" refers to a group consisting of at least one C1-C 20 Alkyl substituted 'X' group. For example, as used herein, the term "(C1-C 20 Alkyl) C3-C 10 "Cycloalkyl" refers to a group consisting of at least one C1-C 20 Alkyl-substituted C3-C 10 Cycloalkyl, and as used herein the term "(C1-C 20 "Alkyl)phenyl" refers to a 20 Alkyl-substituted phenyl. An example of the term (C1 alkyl)phenyl is tolyl.
[0834] 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 5,5-dioxide group” They respectively refer to the following heterocyclic groups: which 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, and dibenzothiophene 5,5-dioxide group", wherein in each group, at least one ring-forming carbon atom is replaced by nitrogen.
[0835] Substituted C5-C 30 Carbocyclic groups, substituted C2-C 30 Heterocyclic groups, 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 Alkylaryl, 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 60At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be:
[0836] Deuterium, -F, -Cl, -Br, -I, -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;
[0837] 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, -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, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused 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;
[0838] 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, -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 fused polycyclic group, monovalent non-aromatic fused 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;
[0839] -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
[0840] Its combination.
[0841] In this manual, Q1-Q9, Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 Each of them may be independently: hydrogen, deuterium, -F, -Cl, -Br, -I, 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, or C1-C2-C3-C4-C6-C1-C2-C3-C1-C2 ... 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-C60 Heteroarylthio group, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, C1-C 60 Alkyl, C6-C 60 aryl, or a combination thereof.
[0842] For example, Q1-Q9, Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 Can be independently:
[0843] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or
[0844] 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: deuterium, C1-C 10 alkyl, phenyl, or a combination thereof.
[0845] Hereinafter, the composition and light-emitting device according to one or more embodiments are further described in detail with reference to Synthesis Examples and Examples. However, the present disclosure is not limited thereto. The phrase "using B instead of A" used in describing Synthesis Examples means that, on a molar equivalent basis, the amount of A used is the same as the amount of B used.
[0846] Example
[0847] Synthesis Example 1 (Compound Pt-1 or Compound 3-302 of Group 1-1)
[0848]
[0849] Synthesis of compound Pt-1(3)
[0850] 2.6 grams (g) (0.006 moles (mmol), 1.2 equivalents (equiv.)) of compound Pt-1 (2), 3.0 g (0.005 mol, 1 equivalent) of compound Pt-1 (1), 0.43 g (0.00037 mol, 0.07 equivalent) of tetrakis(triphenylphosphine)palladium (0), and 2.3 g (0.016 mol, 3 equivalents) of potassium carbonate were mixed with 20 mL of a mixture including tetrahydrofuran (THF) and deionized (DI) water in a volume ratio of 3:1, and the mixed solution was heated under reflux for 12 hours. The reaction mixture was then allowed to cool to room temperature, and a precipitate was removed therefrom by filtration. The filtrate was then washed with ethyl acetate (EA) / H2O, the solvent was removed under reduced pressure, and the residue was subjected to column chromatography (EA / hexane (Hex), with an elution gradient of 8% to 12% (by volume, the same below) of EA) to obtain 3.7 g (90% yield) of compound Pt-1 (3). The obtained compound was confirmed by high resolution mass spectrometry (HRMS) using matrix-assisted laser desorption ionization (MALDI) and high performance liquid chromatography (HPLC) analysis.
[0851] HRMS (MALDI): For C 54 H 53 Calculated value of N3O: m / z 759.4189, found: 759.4187.
[0852] Synthesis of compound Pt-1
[0853] 3.7g (4.9mmol, 1 equivalent) of compound Pt-1 (3) and 2.4g (5.8mmol, 1.2 equivalents) of K2PtCl4 were mixed with a 70mL mixture comprising 60mL of AcOH and 10mL of DI water, and the mixed solution was heated under reflux for 16 hours. The reaction mixture was then allowed to cool to room temperature, and the precipitate was removed therefrom by filtration. The filtrate was then dissolved in dichloromethane (MC) and washed with DI water. Subsequently, the solvent was removed under reduced pressure, and the residue was subjected to column chromatography (MC 30% to 35% / Hex 65% to 70%) to obtain 1.72g (37% yield, 99.9% or greater purity) of compound Pt-1. The obtained compound was confirmed by HRMS and HPLC analysis.
[0854] HRMS (MALDI): For C 54 H 51 Calculated value for N3OPt: m / z 952.3680, found: 952.3682.
[0855] Synthesis Example 2 (Compound Pt-2 or Compound 30 of Group 1-3)
[0856]
[0857] Synthesis of compound Pt-2(3)
[0858] 2.7 g (0.006 mol, 1.2 equivalents) of compound Pt-2 (2), 3.0 g (0.005 mol, 1 equivalent) of compound Pt-2 (1), 0.44 g (0.00038 mol, 0.07 equivalent) of tetrakis (triphenylphosphine) palladium (0), and 2.2 g (0.016 mol, 3 equivalents) of potassium carbonate were mixed with 20 mL of a mixture comprising tetrahydrofuran (THF) and deionized (DI) water in a volume ratio of 3:1, and the mixed solution was heated under reflux for 12 hours. The reaction mixture was then allowed to cool to room temperature, and the precipitate was removed therefrom by filtration. The filtrate was then washed with EA / H2O, the solvent was removed under reduced pressure, and the residue was subjected to column chromatography (EA / Hex, with an elution gradient of 8% to 12% of EA) to obtain 3.6 g (85% yield) of compound Pt-2 (3). The obtained compound was confirmed by HRMS and HPLC analysis.
[0859] HRMS (MALDI): For C 55 H 52 Calcd for D3N3O: m / z 776.4533, found: 776.4535.
[0860] Synthesis of compound Pt-2
[0861] 3.6g (4.6mmol, 1 equivalent) compound Pt-2 (3) and 2.3g (5.6mmol, 1.2 equivalent) K2PtCl4 are mixed with 70mL mixture including 60mL AcOH and 10mL DI water, and the mixed solution is heated under reflux for 16 hours. The reaction mixture is then allowed to cool to room temperature, and the precipitate is removed therefrom by filtration. The filtrate is then dissolved in MC and then washed with DI water. Subsequently, the solvent is removed under reduced pressure, and column chromatography (MC 30% to 35% / Hex65% to 70%) is carried out on the residue to obtain 1.75g (39% yield, 99.9% or greater purity) of compound Pt-2. The obtained compound is confirmed by HRMS and HPLC analysis.
[0862] HRMS (MALDI): For C 55 H 50 Calculated for D3N3OPt: m / z 969.4025, found: 969.4027.
[0863] Synthesis Example 3 (Compound Ir-1 or Compound 16 of Group 2-1)
[0864]
[0865] Synthesis of compound Ir-1(1)
[0866] 2-Phenyl-5-(trimethylsilyl)pyridine (7.5 g, 33.1 mmol) and iridium chloride hydrate (IrCl3·(H2O) n , n=3) (5.2 g, 14.7 mmol) was mixed with 120 mL of ethoxyethanol and 40 mL of DI water, and the mixed solution was stirred for 24 hours while heating under reflux. Then, the reaction mixture was allowed to cool to room temperature. The resulting solid was separated therefrom by filtration, washed thoroughly with water, methanol, and hexane in the order stated, and then dried in a vacuum oven to obtain 8.2 g (82% yield) of compound Ir-1(1).
[0867] Synthesis of compound Ir-1(2)
[0868] Compound Ir-1(1) (1.6 g, 1.2 mmol) was mixed with 45 mL of dichloromethane, and a mixture of silver trifluoromethanesulfonate (AgOTf, 0.6 g, 2.3 mmol) and 15 mL of methanol (MeOH) was added thereto. The resulting mixture was then stirred at room temperature for 18 hours while blocking light with aluminum foil, then filtered through diatomaceous earth to remove the resulting solid, and the filtrate was subjected to reduced pressure to obtain a solid (Compound Ir-1-(2)). Compound Ir-1-(2) was used in the subsequent reaction without additional purification.
[0869] Synthesis of compound Ir-1
[0870] Compound Ir-1(2) (1.8 g, 2.15 mmol) and compound Ir-1(3) (2-(dibenzo[b,d]furan-4-yl)-1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-1H-benzo[d]imidazole, 1.0 g, 2.04 mmol) were mixed with 10 mL of 2-ethoxyethanol and 10 mL of N,N-dimethylformamide, and the mixed solution was stirred for 48 hours while heating under reflux. Then, the reaction mixture was allowed to cool to room temperature. The product thus obtained was decompressed, and the resulting solid was subjected to column chromatography (eluent: MC and Hex) to obtain 1.10 g of compound Ir-1 (44% yield). The obtained compound was confirmed by HRMS and HPLC analysis.
[0871] HRMS (MALDI): For C 65 H 63Calculated value for IrN4OSi2: m / z 1164.4170, found: 1164.4171.
[0872] Synthesis Example 4 (Compound Ir-2 or Compound 115 of Group 2-4)
[0873]
[0874] Synthesis of compound Ir-2
[0875] Compound Ir-1(2) (1.9 g, 2.2 mmol) and compound Ir-2(1) (1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-2-(phenanthro[3,2-b]benzofuran-11-yl)-1H-benzo[d]imidazole, 1.3 g, 2.1 mmol) were mixed with 10 mL of 2-ethoxyethanol and 10 mL of N,N-dimethylformamide, and the mixed solution was stirred for 48 hours while heating under reflux. Then, the temperature was allowed to decrease to room temperature. The product thus obtained was decompressed, and the resulting solid was subjected to column chromatography (eluent: MC and Hex) to obtain 1.10 g of compound Ir-2 (39% yield). The obtained compound was confirmed by HRMS and HPLC analysis.
[0876] HRMS (MALDI): For C 73 H 67 Calculated value of IrN4OSi2: m / z 1264.4483, found: 1264.4486.
[0877] Synthesis Example 5 (Compound Ir-3 or Compound 116 of Group 2-4)
[0878]
[0879] Synthesis of compound Ir-3
[0880] Compound Ir-1(2) (2.0 g, 2.3 mmol) and compound Ir-3(1) (2-(dibenzo[b,d]furan-4-yl)-1-(2,6-diisopropylphenyl)-1H-benzo[d]imidazole, 1.0 g, 2.2 mmol) were mixed with 10 mL of 2-ethoxyethanol and 10 mL of N,N-dimethylformamide, and the mixed solution was stirred for 48 hours while heating under reflux. Then, the reaction mixture was allowed to cool to room temperature. The product thus obtained was decompressed, and the resulting solid was subjected to column chromatography (eluent: MC and Hex) to obtain 1.20 g of compound Ir-3 (48% yield). The obtained compound was confirmed by HRMS and HPLC analysis.
[0881] HRMS (MALDI): For C 59 H 59 Calculated for IrN4OSi2: m / z 1088.3857, found: 1088.3858.
[0882] Manufacturing of OLED 1
[0883] An ITO (anode) patterned glass substrate was cut into a size of 50 millimeters (mm) × 50 mm × 0.5 mm, ultrasonically treated with isopropyl alcohol and DI water for 5 minutes each, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes. The resulting glass substrate was loaded onto a vacuum deposition device.
[0884] HT3 and F6-TCNNQ were vacuum deposited on the anode at a weight ratio of 98:2 to form a A hole injection layer having a thickness of 1000 nm was formed, and HT3 was vacuum-deposited on the hole injection layer to form a hole injection layer having a thickness of 1000 nm. H-H1 is vacuum deposited on the hole transport layer to form a hole transport layer having a thickness of The thickness of the electron blocking layer is .
[0885] Subsequently, the host and the dopant were co-deposited on the electron blocking layer in a weight ratio of 88:12 to form a As the host, H-H1 and H-H2 were used at a weight ratio of 5:5, and as the dopant, the first compound and the second compound shown in Table 1 were used at a weight ratio of 1:1.
[0886] Then, ET3 and ET-D1 were co-deposited on the emissive layer in a volume ratio of 50:50 to form a An electron transport layer having a thickness of An electron injection layer having a thickness of , and Al is vacuum deposited on the electron injection layer to form A cathode with a thickness of is formed, thereby completing the manufacture of the organic light-emitting device.
[0887]
[0888] Manufacturing of OLED 2-4 and AE
[0889] An organic light-emitting device was manufactured in the same manner as that of OLED 1, except that, in forming the emission layer, for use as a dopant, the corresponding compounds shown in Table 1 were used.
[0890] Evaluation Example 1
[0891] For OLEDs 1-4 and AE, the driving voltage (V), the maximum emission peak wavelength (λ 最大 , nm), maximum external quantum efficiency (maximum EQE, %), and lifetime (LT 97 , relative value, % based on OLED-A), and the results are shown in Table 1. A current-voltage meter (Keithley 2400) and a luminance meter (Topcon SR3) were used as equipment for evaluation, and the lifespan (T 97 )(at 18,000 candela / m² (cd / m 2 ) is obtained by measuring the amount of time that elapses until the luminance decreases to 97% of the initial luminance of 100%, and the results are expressed as relative values based on OLED-A.
[0892] Table 1
[0893]
[0894]
[0895]
[0896] Referring to Table 1, it was confirmed that OLEDs 1 to 4 each emitted green light and had improved properties in terms of driving voltage, EQE, and lifespan compared to OLEDs AE.
[0897] According to one or more embodiments, an electronic device such as a light emitting device using the composition may have improved driving voltage, improved external quantum efficiency, and improved lifespan characteristics.
[0898] It should be understood that the one or more exemplary embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. The description of some 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 skilled 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 composition comprising: a first compound represented by Formula 1-1; and The second compound represented by Formula 2: Formula 2 M2(L 11 ) n11 (L 12 ) n12 (L 13 ) n13 Wherein, in formula 1-1, M1 is platinum (Pt) or palladium (Pd), In formula 2, M2 is iridium (Ir), In formula 2, L 11 is a ligand represented by formula 2-1, In formula 2, L 12 is a ligand represented by formula 2-2, In formula 2, L 13 is a ligand represented by formula 2-1 or 2-2, In formula 2, L 11 and L 12 Different from each other, In Formula 2, n11 and n12 are each independently 1 or 2, n13 is 0, and the sum of n11+n12+n13 is equal to 3, In formulae 1-1, 2-1, and 2-2, X1 is C, X2-X4 are each independently C or N, Y1 and Y3 are each N, Y2 and Y4 are each C, In formula 1-1, X5 is O or S, In Formula 1-1, the bond between X5 and M1 is a covalent bond, two of the bonds between X2 and M1, the bond between X3 and M1, and the bond between X4 and M1 are each coordination bonds, and the other of the bonds between X2 and M1, the bond between X3 and M1, and the bond between X4 and M1 is a covalent bond, In formula 1-1, X 11 N or C(R 11 ), X 12 N or C(R 12 ), X 13 N or C(R 13 ), and X 14 N or C(R 14 ), X 21 N or C(R 21 ), X 22 N or C(R 22 ), and X 23 N or C(R 23 ), X 29 O, S, N-[(L2) b2 -(R2) c2 ]、C(R 29a )(R 29b ), or Si(R 29a )(R 29b ), X 31 N or C(R 31 ), X 32 N or C(R 32 ), and X 33 N or C(R 33 ), X 41 N or C(R 41 ), X 42 N or C(R 42 ), X 43 N or C(R 43 ), and X 44 N or C(R 44 ), In formula 2-1, ring A1 is a pyridine group, In formula 2-2, ring A3 is a pyridine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a benzimidazole group, a naphthimidazole group, a phenanthimidazole group, or a pyridimidazole group, In formula 2-1, The group represented by is represented by one of the formulas CR1, CR2, CR5 and CR8: In formula 2-2, The group represented by is represented by one of the formulae CR2, CR5, CR8, and CR24 to CR29: Wherein, in the formulas CR1, CR2, CR5, CR8, and CR24 to CR29, Y 49 is O, S, Se, N-[W4-(Z4) e4 , C(Z 49a )(Z 49b ), or Si(Z 49a )(Z 49b ), W4, e4 and Z4 are each defined as follows, Z 49a and Z 49b Each as defined for Z4, Y 21 To Y 24 are each independently N or C, Ring A 40 C6-C 14 Carbocyclic group or C4-C 14 Heterocyclic groups, * indicates the binding site with M2 in Formula 2, and *" represents the binding site with Ring A1 in Formula 2-1 or Ring A3 in Formula 2-2, In formulas 1-1, 2-1, and 2-2, L2 and W1-W4 are each independently a single bond, unsubstituted or replaced by at least one R 10a Substituted C5-C 30 Carbocyclic groups, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups, In formula 1-1, b2 is an integer from 1 to 10, In formulas 1-1, 2-1, and 2-2, R 11 -R 14 、R 21 -R 23 , R2, R 29a 、R 29b 、R 31 -R 33 、R 41 -R 44 , and Z1-Z4 are each independently hydrogen, deuterium, -F, cyano, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, 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 an alkylheteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5), In formulas 1-1, 2-1, and 2-2, c2 and e1-e4 are each independently an integer of 0-20, In formula 2-1, d1 is an integer from 0 to 4, In formula 2-1, d2 is an integer from 0 to 6, In formula 2-2, d3 is an integer from 0 to 9, In formula 2-2, d4 is an integer from 0 to 16, In Formulae 1-1, 2-1, and 2-2, at least two substituents from the following groups are each independently optionally linked to each other to form an unsubstituted or substituted group. 10a Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic group: i) R 11 -R 14 ii) two or more of R 21 -R 23 iii) two or more of R 31 -R 33 iv) two or more of R 41 -R 44 v) two or more of a plurality of Z1; vi) two or more of a plurality of Z2; vii) two or more of a plurality of Z3; viii) two or more of a plurality of Z4, ix) R 11 -R 14 、R 21 -R 23 、R 31 -R 33 , and R 41 -R 44 and x) two or more of Z1-Z4, R 10a As for R 11 As defined, * and *' each represent a binding site to an adjacent atom, and Substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C1-C 60 Alkoxy, substituted C1-C 60 Alkylthio, substituted C3-C 10 Cycloalkyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkyl aryl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C1-C 60 Heteroaryl, substituted C2-C 60 At least one substituent of the alkylheteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is: Deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 60 Alkyl, C2-C 60 Alkenyl, or C1-C 60 alkoxy; C1-C 60 Alkyl, C2-C 60 Alkenyl, or C1-C 60 Alkoxy: deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, or a combination thereof; C3-C 10 Cycloalkyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 60 Alkyl, C2-C 60 Alkenyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or a combination thereof; -Si(Q 33 )(Q 34 )(Q 35 )、 or -Ge(Q 33 )(Q 34 )(Q 35 ); or Its combination, Among them, Q3-Q5, and Q 33 -Q 35 are each independently: hydrogen, deuterium, -F, or C1-C 60 Alkyl, C3-C 10 Cycloalkyl, C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, C1-C 60 Alkyl, C6-C 60 aryl, or a combination thereof.
2. The composition according to claim 1, wherein In formula 1-1, X3 is C, and X2 and X4 are each N, or X4 is C, and X2 and X3 are each N.
3. The composition according to claim 1, wherein In Formulae 2-1 and 2-2, Ring A1 and Ring A3 are different from each other.
4. The composition according to claim 1, wherein In Formulae 2-1 and 2-2, Ring A2 and Ring A4 are different from each other.
5. The composition according to claim 1, wherein In formula 2-1, e1 and d1 are each non-zero, and At least one Z1 is deuterated C1-C 20 Alkyl, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5).
6. The composition according to claim 1, wherein In formula 2-2, Y3 is N, and Depend on The group represented by is represented by one of the formulae NR1, NR11, NR14, NR17, NR20, NR22, NR23, NR25, NR26, NR28, NR30 to NR34, NR37, NR38, NR40 to NR42, NR44, NR45, NR46 and NR48: wherein, in the formulas NR1, NR11, NR14, NR17, NR20, NR22, NR23, NR25, NR26, NR28, NR30 to NR34, NR37, NR38, NR40 to NR42, NR44, NR45, NR46, and NR48, Y 39 is N-[W3-(Z3) e3 , W3, Z3, and e3 are as defined in claim 1, *' represents the binding site with M2 in Formula 2, and *" indicates the binding site to loop A4.
7. The composition according to claim 1, wherein In formulas CR24 to CR29, Ring A 40 is a benzene group, a naphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, or a benzoquinazoline group.
8. The composition of claim 1, wherein The first compound emits a first light having a first spectrum, and λP1 represents an emission peak wavelength in nanometers (nm) in the first spectrum, The second compound emits a second light having a second spectrum, and λP2 represents an emission peak wavelength in nm in the second spectrum, and λP1 and λP2 are each within the range of 480 nm to 580 nm.
9. A layer comprising the composition according to any one of claims 1 to 8.
10. A light emitting device comprising: a first electrode; a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and The organic layer comprises at least one composition according to any one of claims 1 to 8. The light emitting device of claim 10 , wherein the emissive layer comprises the at least one composition.
12. An electronic device comprising the light emitting device according to claim 10 or 11.
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