Organic light-emitting device and device including the same
The use of a specialized organic layer composition with compounds represented by Formulas 1, 2, 3, and 4-3 addresses performance limitations in organic light-emitting devices, improving viewing angle, contrast ratio, brightness, and response speed.
Patent Information
- Application Number
- CN202011038599.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2019-10-04
- Filing Date
- 2020-09-28
- Publication Date
- 2024-12-27
- Estimated Expiration
- 2040-09-28
AI Technical Summary
Existing organic light-emitting devices face challenges in achieving optimal performance in terms of viewing angle, contrast ratio, brightness, driving voltage, and response speed.
The device incorporates a specific organic layer composition comprising compounds represented by Formulas 1, 2, 3, and 4-3, which include distinct compounds with varying structural elements to enhance light emission efficiency and performance.
The proposed organic layer composition improves the viewing angle, contrast ratio, brightness, and response speed of the organic light-emitting device, enhancing overall performance.
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Figure CN112614950B_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to Korean Patent Application No. 10-2019-0123355 filed on October 4, 2019 in the Korean Intellectual Property Office, the disclosure of which is incorporated herein by reference in its entirety. Technical Field
[0003] One or more embodiments relate to an organic light-emitting device and an apparatus including the same. Background Art
[0004] The organic light-emitting device is a self-emissive device that has a wide viewing angle, a high contrast ratio, and / or a short response time, and / or exhibits suitable (eg, excellent) characteristics in terms of brightness, driving voltage, and / or response speed.
[0005] In an organic light-emitting device, a first electrode is arranged on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. Holes provided by the first electrode can move toward the emission layer through the hole transport region, and electrons provided by the second electrode can move toward the emission layer through the electron transport region. Holes and electrons as carriers recombine in the emission layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating (e.g., emitting) light. Summary of the invention
[0006] Aspects according to one or more embodiments are directed to an organic light-emitting device and an apparatus including the same.
[0007] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the embodiments presented in the disclosure.
[0008] According to one or more embodiments, an organic light emitting device includes:
[0009] a first electrode;
[0010] a second electrode facing the first electrode; and
[0011] an organic layer between the first electrode and the second electrode,
[0012] The organic layer includes an emission layer,
[0013] The emission layer includes a first compound, a second compound, a third compound and a fourth compound,
[0014] The first compound is represented by Formula 1;
[0015] The second compound is represented by Formula 2;
[0016] The third compound is represented by Formula 3;
[0017] The fourth compound is represented by any one of Formula 4-1 to Formula 4-3; and
[0018] The first compound, the second compound, the third compound and the fourth compound are different from each other:
[0019] Formula 1
[0020]
[0021] Formula 2
[0022]
[0023] Formula 3
[0024] M 31 (L 31 ) n31 (L 32 ) n32
[0025] Formula 4-1
[0026] (D 41 ) n41 -(L 41 ) a41 -(A 41 ) m41
[0027] Formula 4-2
[0028] (D 41 ) n41 -(L 41 ) a41 -(A 41 ) m41 -(L 42 ) a42 -(D 42 ) n42
[0029] Formula 4-3
[0030] (A 41 ) m41 -(L 41 ) a41 -(D 41 ) n41 -(L 42 ) a42 -(A 42 ) m42 .
[0031] In formula 1,
[0032] X 11 Can be selected from O, S, N (R 19 ) and C(R 19 )(R 20 );
[0033] R 11 To R 20 Can be independently selected from:
[0034] By *-(L 11 ) a11 -A 11 The groups represented by hydrogen, deuterium, C 1 -C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 ) and -N(Q 1 )(Q 2 );
[0035] A ring group containing no π-electron-depleted nitrogen substituted with at least one selected from the group consisting of deuterium, C 1 -C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 ) and -N(Q 31 )(Q 32 );as well as
[0036] A π-electron-depleted nitrogen-free ring group substituted with at least one π-electron-depleted nitrogen-free ring group, wherein the at least one π-electron-depleted nitrogen-free ring group is substituted with at least one selected from the group consisting of deuterium, C 1 -C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 21 )(Q 22 )(Q 23 )、-Si(Q 21 )(Q 22 )(Q 23 )、-B(Q 21 )(Q 22) and -N(Q 21 )(Q 22 ),
[0037] L 11 Can be selected from:
[0038] A ring group that does not contain π-electron-depleted nitrogen, -C(Q 1 )(Q 2 )-、-Si(Q 1 )(Q 2 )-、-B(Q 1 )- and -N(Q 1 )-;as well as
[0039] A ring group containing no π-electron-depleted nitrogen substituted with at least one selected from the group consisting of deuterium, C 1 -C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 ) and -N(Q 31 )(Q 32 ),
[0040] a11 can be selected from 1, 2 and 3, and
[0041] A 11 Can be selected from:
[0042] A ring group that does not contain a π-electron-depleted nitrogen;
[0043] A ring group containing no π-electron-depleted nitrogen substituted with at least one selected from the group consisting of deuterium, C 1 -C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 ) and -N(Q 31 )(Q 32 );as well as
[0044] A π-electron-depleted nitrogen-free ring group substituted with at least one π-electron-depleted nitrogen-free ring group, wherein the at least one π-electron-depleted nitrogen-free ring group is substituted with at least one selected from the group consisting of deuterium, C 1 -C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 21 )(Q 22 )(Q 23 )、-Si(Q 21 )(Q 22 )(Q 23 )、-B(Q 21 )(Q 22 ) and -N(Q 21 )(Q 22 ).
[0045] In formula 2,
[0046] L 21 To L 23 can be independently selected from substituted or unsubstituted C 5 -C 30 Carbocyclic group and substituted or unsubstituted C 1 -C 30 Heterocyclic group,
[0047] a21 to a23 may each be independently selected from 0, 1 and 2,
[0048] R 21 To R 23 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1)(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ).
[0049] In formula 3,
[0050] M 31 It can be selected from the 4th period transition metal, the 5th period transition metal and the 6th period transition metal of the periodic table,
[0051] L 31 may be a ligand represented by one of Formulae 3A to 3D,
[0052]
[0053] L 32 can be selected from monodentate ligands, bidentate ligands and tridentate ligands,
[0054] n31 can be 1 or 2,
[0055] n32 can be selected from 0, 1, 2, 3 and 4,
[0056] A 31 To A 34 Can be independently selected from C 5 -C 30 Carbocyclic and C 1 -C 30 Heterocyclic group,
[0057] T 31 To T 34 can be independently selected from a single bond, a double bond, *-O-*', *-S-*', *-C(=O)-*', *-S(=O)-*', *-C(R 35 )(R 36 )-*'、*-C(R 35 )=C(R 36 )-*'、*-C(R 35 )=*'、*-Si(R 35)(R 36 )-*'、*-B(R 35 )-*'、*-N(R 35 )-*' and *-P(R 35 )-*',
[0058] k31 to k34 may each be independently selected from 1, 2 and 3,
[0059] Y 31 To Y 34 can be independently selected from a single bond, *-O-*', *-S-*', *-C(R 37 )(R 38 )-*'、*-Si(R 37 )(R 38 )-*'、*-B(R 37 )-*'、*-N(R 37 )-*' and *-P(R 37 )-*',
[0060] * 1 ,* 2 ,* 3 and* 4 You can indicate and M 31 The binding site
[0061] R 31 To R 38 can be independently selected from hydrogen, 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, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ), where R 31 To R 38 may be optionally linked to each other to form a substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 a heterocyclic group, and
[0062] b31 to b34 may each independently be an integer selected from 0 to 10.
[0063] In Formula 4-1 to Formula 4-3,
[0064] A 41 and A 42 Can be independently selected from:
[0065] A ring group containing no π-electron-depleted nitrogen, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 ) and -N(Q 1 )(Q 2 );
[0066] A ring group containing no π-electron-depleted nitrogen substituted with at least one selected from the group consisting of deuterium, C 1-C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 ) and -N(Q 31 )(Q 32 );as well as
[0067] A π-electron-depleted nitrogen-free ring group substituted with at least one π-electron-depleted nitrogen-free ring group, wherein the at least one π-electron-depleted nitrogen-free ring group is substituted with at least one selected from the group consisting of deuterium, C 1 -C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 21 )(Q 22 )(Q 23 )、-Si(Q 21 )(Q 22 )(Q 23 )、-B(Q 21 )(Q 22 ) and -N(Q 21 )(Q 22 ),
[0068] m41 and m42 can be independently selected from 1, 2 and 3,
[0069] D 41 and D 42 Can be independently selected from:
[0070] -F, cyano, π-electron-depleted nitrogen-containing ring group, C(=O)-containing group, S(=O)-containing group, S(=O)-containing 2 A group containing P(=O) and a group containing P(=S);
[0071] A π-electron-depleted nitrogen-containing ring group, a C(═O)-containing group, a S(═O)-containing group, a S(═O)-containing group, each substituted with at least one selected from the following 2 Groups containing P(=O) and groups containing P(=S): deuterium, -F, cyano, C 1 -C 60 Alkyl groups, ring groups containing π-electron-depleted nitrogen, and ring groups not containing π-electron-depleted nitrogen;
[0072] A π-electron-depleted nitrogen-containing ring group, a C(═O)-containing group, a S(═O)-containing group, a S(═O)-containing group, each substituted with at least one selected from the following2 The group containing P(=O) and the group containing P(=S): each independently selected from deuterium, -F, cyano, C 1 -C 60 At least one of an alkyl group, a ring group containing a π-electron-depleted nitrogen, and a ring group not containing a π-electron-depleted nitrogen is substituted with C 1 -C 60 Alkyl groups, ring groups containing π-electron-depleted nitrogen, and ring groups not containing π-electron-depleted nitrogen;
[0073] Each of the following C 1 -C 60 Alkyl groups and ring groups without π-electron-depleted nitrogen: -F, cyano groups and ring groups with π-electron-depleted nitrogen;
[0074] Each of the C 1 -C 60 An alkyl group and a ring group containing no π-electron-depleted nitrogen, wherein at least one ring group containing π-electron-depleted nitrogen is substituted by at least one selected from the group consisting of deuterium, -F, cyano, C 1 -C 60 Alkyl groups, π-electron-depleted nitrogen-containing ring groups, and π-electron-free nitrogen-free ring groups; and
[0075] Each of the following C 1 -C 60 Alkyl and ring groups without π-electron-depleted nitrogen: each independently substituted with at least one selected from -F, cyano and ring groups containing π-electron-depleted nitrogen 1 -C 60 Alkyl groups and ring groups that do not contain π-electron-depleted nitrogen,
[0076] n41 and n42 may be each independently selected from 1, 2 and 3,
[0077] L 41 and L 42 Can be independently selected from:
[0078] A ring group that does not contain π-electron-depleted nitrogen, -C(Q 1 )(Q 2 )-、-Si(Q 1 )(Q 2 )-、-B(Q 1 )- and -N(Q 1 )-;as well as
[0079] A ring group containing no π-electron-depleted nitrogen substituted with at least one selected from the group consisting of deuterium, C 1 -C 60Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 ) and -N(Q 31 )(Q 32 ),and
[0080] a41 and a42 may be selected from 0, 1, 2 and 3, respectively.
[0081] In Formula 1, Formula 2, Formula 3 and Formula 4-1 to Formula 4-3,
[0082] Substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 heteroaryl, substituted monovalent non-aromatic fused polycyclic group, substituted monovalent non-aromatic fused heteropolycyclic group, substituted C 5 -C 30 Carbocyclic, substituted C 1 -C 30 Heterocyclic, substituted C 5 -C 60 Carbocyclic and substituted C 1 -C 60 At least one substituent in the heterocyclic group may be selected from:
[0083] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;
[0084] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 );
[0085] C 3 -C 10 Cycloalkyl, C 1 -C 10Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
[0086] Each of the following C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 );as well as
[0087] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),
[0088] Where Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.
[0089] According to one or more embodiments, an apparatus includes a thin film transistor including a source electrode, a drain electrode, and an active layer; and an organic light emitting device, wherein a first electrode of the organic light emitting device is electrically connected to the source electrode or the drain electrode of the thin film transistor. BRIEF DESCRIPTION OF THE DRAWINGS
[0090] The above and other aspects, features and improvements of certain embodiments of the present disclosure will become more apparent from the following description in conjunction with the accompanying drawings, in which:
[0091] Figure 1 A schematic diagram showing an organic light-emitting device according to an embodiment;
[0092] Figure 2 A schematic diagram showing an organic light-emitting device according to another embodiment;
[0093] Figure 3 A schematic diagram showing an organic light-emitting device according to another embodiment; and
[0094] Figure 4 A schematic diagram showing an organic light-emitting device according to another embodiment. DETAILED DESCRIPTION
[0095] Reference will now be made in more detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein similar reference numerals throughout the specification refer to similar elements. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions listed herein. Therefore, the embodiments are described below only by reference to the figures to explain the various aspects of this description. As used herein, the term "and / or" includes any and all combinations of one or more related listed items. Throughout this disclosure, the expression "at least one of a, b, or c" indicates only a, only b, only c, both a and b, both a and c, both b and c, all of a, b, and c, or variations thereof.
[0096] Hereinafter, the inventive concept will be described in more detail by explaining embodiments with reference to the accompanying drawings. When describing with reference to the accompanying drawings, the same or corresponding elements will be given the same reference numerals, and redundant descriptions thereof will be omitted (ie, will not be provided).
[0097] As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise.
[0098] It will be further understood that the terms “comprises” and / or “comprising” as used herein specify the presence of stated features or components, but do not preclude the presence or addition of one or more other features or components.
[0099] It will be understood that when a layer, region or component is referred to as being “formed on” another layer, region or component, it may be directly or indirectly formed on the other layer, region or component. That is, for example, intervening layers, regions or components may be present.
[0100] For convenience of explanation, the sizes of components in the drawings may be exaggerated. In other words, since the sizes and thicknesses of components in the drawings are arbitrarily illustrated for convenience of explanation, the following embodiments are not essentially limited thereto.
[0101] The term "organic layer" used herein refers to a single layer and / or a plurality of layers between a first electrode and a second electrode of an organic light-emitting device. Materials included in the "organic layer" are not limited to organic materials.
[0102] According to one or more embodiments, an organic light-emitting device includes: 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 emission layer includes a first compound, a second compound, a third compound, and a fourth compound, wherein the first compound is represented by the following Formula 1; the second compound is represented by the following Formula 2; the third compound is represented by the following Formula 3; the fourth compound is represented by one of Formulas 4-1 to 4-3; and the first compound, the second compound, the third compound, and the fourth compound are different from each other:
[0103] Formula 1
[0104]
[0105] Formula 2
[0106]
[0107] Formula 3
[0108] M 31 (L 31 ) n31 (L 32 ) n32
[0109] Formula 4-1
[0110] (D 41 ) n41 -(L 41 ) a41 -(A 41 ) m41
[0111] Formula 4-2
[0112] (D 41 ) n41 -(L 41 ) a41 -(A 41 ) m41 -(L 42 ) a42 -(D 42 ) n42
[0113] Formula 4-3
[0114] (A 41 ) m41 -(L 41 ) a41 -(D 41 ) n41 -(L 42 ) a42 -(A 42 ) m42.
[0115] In Formula 1, Formula 2, Formula 3 and Formula 4-1 to Formula 4-3,
[0116] X 11 Can be selected from O, S, N (R 19 ) and C(R 19 )(R 20 );
[0117] R 11 To R 20 Can be independently selected from:
[0118] By *-(L 11 ) a11 -A 11 The groups represented by hydrogen, deuterium, C 1 -C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 ) and -N(Q 1 )(Q 2 );
[0119] A ring group containing no π-electron-depleted nitrogen substituted with at least one selected from the group consisting of deuterium, C 1 -C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 ) and -N(Q 31 )(Q 32 );as well as
[0120] A π-electron-depleted nitrogen-free ring group substituted with at least one π-electron-depleted nitrogen-free ring group, wherein the at least one π-electron-depleted nitrogen-free ring group is substituted with at least one selected from the group consisting of deuterium, C 1 -C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 21 )(Q 22 )(Q 23 )、-Si(Q 21 )(Q22 )(Q 23 )、-B(Q 21 )(Q 22 ) and -N(Q 21 )(Q 22 ),
[0121] L 11 Can be selected from:
[0122] A ring group that does not contain π-electron-depleted nitrogen, -C(Q 1 )(Q 2 )-、-Si(Q 1 )(Q 2 )-、-B(Q 1 )- and -N(Q 1 )-;as well as
[0123] A ring group containing no π-electron-depleted nitrogen substituted with at least one selected from the group consisting of deuterium, C 1 -C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 ) and -N(Q 31 )(Q 32 ),
[0124] a11 can be selected from 1, 2 and 3,
[0125] A 11 Can be selected from:
[0126] A ring group that does not contain a π-electron-depleted nitrogen;
[0127] A ring group containing no π-electron-depleted nitrogen substituted with at least one selected from the group consisting of deuterium, C 1 -C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 ) and -N(Q 31 )(Q 32 );as well as
[0128] A π-electron-depleted nitrogen-free ring group substituted with at least one π-electron-depleted nitrogen-free ring group, wherein the at least one π-electron-depleted nitrogen-free ring group is substituted with at least one selected from the group consisting of deuterium, C 1 -C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 21 )(Q 22 )(Q 23 )、-Si(Q 21 )(Q 22 )(Q 23 )、-B(Q 21 )(Q 22 ) and -N(Q 21 )(Q 22 ),
[0129] L 21 To L 23 can be independently selected from substituted or unsubstituted C 5 -C 30 Carbocyclic group and substituted or unsubstituted C 1 -C 30 Heterocyclic group,
[0130] a21 to a23 may each be independently selected from 0, 1 and 2,
[0131] R 21 To R 23 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3)、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ),
[0132] M 31 It can be selected from the 4th period transition metal, the 5th period transition metal and the 6th period transition metal of the periodic table,
[0133] L 31 may be a ligand represented by one of Formulae 3A to 3D,
[0134]
[0135]
[0136] L 32 can be selected from monodentate ligands, bidentate ligands and tridentate ligands,
[0137] n31 can be 1 or 2,
[0138] n32 can be selected from 0, 1, 2, 3 and 4,
[0139] A 31 To A 34 Can be independently selected from C 5 -C 30 Carbocyclic and C 1 -C 30 Heterocyclic group,
[0140] T 31 To T 34 can be independently selected from a single bond, a double bond, *-O-*', *-S-*', *-C(=O)-*', *-S(=O)-*', *-C(R 35 )(R 36 )-*'、*-C(R 35 )=C(R 36 )-*'、*-C(R 35 )=*'、*-Si(R 35 )(R 36)-*'、*-B(R 35 )-*'、*-N(R 35 )-*' and *-P(R 35 )-*',
[0141] k31 to k34 may each be independently selected from 1, 2 and 3,
[0142] Y 31 To Y 34 can be independently selected from a single bond, *-O-*', *-S-*', *-C(R 37 )(R 38 )-*'、*-Si(R 37 )(R 38 )-*'、*-B(R 37 )-*'、*-N(R 37 )-*' and *-P(R 37 )-*',
[0143] * 1 ,* 2 ,* 3 and* 4 You can indicate and M 31 The binding site
[0144] R 31 To R 38 can be independently selected from hydrogen, 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, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ), where R 31 To R 38 (For example, the adjacent R 31 To R 38 ) may be optionally linked to each other to form a substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,
[0145] b31 to b34 may each independently be an integer selected from 0 to 10,
[0146] A 41 and A 42 Can be independently selected from:
[0147] A ring group containing no π-electron-depleted nitrogen, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 ) and -N(Q 1 )(Q 2 );as well as
[0148] A ring group containing no π-electron-depleted nitrogen substituted with at least one selected from the group consisting of deuterium, C 1 -C 60Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 ) and -N(Q 31 )(Q 32 );as well as
[0149] A π-electron-depleted nitrogen-free ring group substituted with at least one π-electron-depleted nitrogen-free ring group, wherein the at least one π-electron-depleted nitrogen-free ring group is substituted with at least one selected from the group consisting of deuterium, C 1 -C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 21 )(Q 22 )(Q 23 )、-Si(Q 21 )(Q 22 )(Q 23 )、-B(Q 21 )(Q 22 ) and -N(Q 21 )(Q 22 ),
[0150] m41 and m42 can be independently selected from 1, 2 and 3,
[0151] D 41 and D 42 Can be independently selected from:
[0152] -F, cyano, π-electron-depleted nitrogen-containing ring group, C(=O)-containing group, S(=O)-containing group, S(=O)-containing 2 A group containing P(=O) and a group containing P(=S);
[0153] A π-electron-depleted nitrogen-containing ring group, a C(═O)-containing group, a S(═O)-containing group, a S(═O)-containing group, each substituted with at least one selected from the following 2 Groups containing P(=O) and groups containing P(=S): deuterium, -F, cyano, C 1 -C 60 Alkyl groups, ring groups containing π-electron-depleted nitrogen, and ring groups not containing π-electron-depleted nitrogen;
[0154] Each of the following C 1 -C 60Alkyl groups and ring groups without π-electron-depleted nitrogen: -F, cyano groups and ring groups with π-electron-depleted nitrogen;
[0155] A π-electron-depleted nitrogen-containing ring group, a C(═O)-containing group, a S(═O)-containing group, a S(═O)-containing group, each substituted with at least one selected from the following 2 The group containing P(=O) and the group containing P(=S): each independently selected from deuterium, -F, cyano, C 1 -C 60 At least one of an alkyl group, a ring group containing a π-electron-depleted nitrogen, and a ring group not containing a π-electron-depleted nitrogen is substituted with C 1 -C 60 Alkyl groups, ring groups containing π-electron-depleted nitrogen, and ring groups not containing π-electron-depleted nitrogen;
[0156] Each of the C 1 -C 60 An alkyl group and a ring group containing no π-electron-depleted nitrogen, wherein at least one ring group containing π-electron-depleted nitrogen is substituted by at least one selected from the group consisting of deuterium, -F, cyano, C 1 -C 60 Alkyl groups, π-electron-depleted nitrogen-containing ring groups, and π-electron-free nitrogen-free ring groups; and
[0157] Each of the following C 1 -C 60 Alkyl and ring groups without π-electron-depleted nitrogen: each independently substituted with at least one selected from -F, cyano and ring groups containing π-electron-depleted nitrogen 1 -C 60 Alkyl groups and ring groups that do not contain π-electron-depleted nitrogen,
[0158] n41 and n42 may be each independently selected from 1, 2 and 3,
[0159] L 41 and L 42 Can be independently selected from:
[0160] A ring group that does not contain π-electron-depleted nitrogen, -C(Q 1 )(Q 2 )-、-Si(Q 1 )(Q 2 )-、-B(Q 1 )- and -N(Q 1 )-;as well as
[0161] A ring group containing no π-electron-depleted nitrogen substituted with at least one selected from the group consisting of deuterium, C 1 -C 60Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 ) and -N(Q 31 )(Q 32 ),and
[0162] a41 and a42 can be each independently selected from 0, 1, 2 and 3,
[0163] Where Q 1 To Q 3 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.
[0164] For example, R selected from Formula 1 11 To R 19 At least one of them can be composed of *-(L 11 )a11 -A 11 Represents the group.
[0165] For example, X in Formula 1 11 Can be O, S or N (R 19 ).
[0166] For example, R in Formula 1 11 To R 20 Can be independently selected from:
[0167] By *-(L 11 ) a11 -A 11 The groups represented by hydrogen, deuterium, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 ) and -N(Q 1 )(Q 2 );
[0168] phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl and dinaphthothiophenyl: deuterium, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q31 )(Q 32 ) and -N(Q 31 )(Q 32 );as well as
[0169] phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, 1-Hydroxy, ... 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, -C(Q 21 )(Q 22 )(Q 23 )、-Si(Q 21 )(Q 22 )(Q 23 )、-B(Q 21 )(Q 22 ) and -N(Q 21 )(Q 22 ) is at least one substituted phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl and dinaphthothiophenyl.
[0170] For example, L in Formula 1 11 Can be selected from:
[0171] Phenyl, naphthyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, phenanthrenyl, pyrenyl, yl, peryl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, -C(Q 1 )(Q 2 )- and -Si(Q 1 )(Q 2 )-;as well as
[0172] phenyl, naphthyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, phenanthrenyl, pyrenyl, yl, peryl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl: deuterium, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, -C(Q 31 )(Q 32 )(Q 33 ) and -Si(Q 31 )(Q 32 )(Q 33 ).
[0173] In one embodiment, L in Formula 1 11 Can be selected from:
[0174] Phenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, -C(Q 1 )(Q 2 )- and -Si(Q 1 )(Q 2 )-;as well as
[0175] Phenyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl, each substituted by at least one selected from the group consisting of deuterium, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, -C(Q 31 )(Q 32 )(Q 33 ) and -Si(Q 31 )(Q 32 )(Q 33 ).
[0176] For example, a11 in Formula 1 may be 1 or 2.
[0177] For example, A in Formula 1 11 Can be selected from:
[0178] Phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, 1-Benzene, 2 ...
[0179] phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl and dinaphthothiophenyl: deuterium, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 ) and -N(Q 31 )(Q 32 );as well as
[0180] phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, 1-Hydroxy, ... 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, -C(Q 21 )(Q 22 )(Q 23 )、-Si(Q 21 )(Q 22 )(Q 23 )、-B(Q 21 )(Q 22 ) and -N(Q 21 )(Q 22 ) is at least one substituted phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl and dinaphthothiophenyl.
[0181] In one embodiment, A in Formula 1 11 Can be selected from:
[0182] Phenyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl;
[0183] Phenyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl, each substituted by at least one selected from the group consisting of deuterium, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, -C(Q 31 )(Q 32 )(Q 33 ) and -Si(Q 31 )(Q 32 )(Q 33 );as well as
[0184] Phenyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl, each of which is substituted by at least one selected from the group consisting of deuterium, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, -C(Q 21 )(Q 22 )(Q 23 ) and -Si(Q 21 )(Q 22 )(Q 23 ) is at least one substituted phenyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl.
[0185] In one embodiment, A in Formula 1 11 It can be expressed by one of the following equations 8-1 to 8-5:
[0186]
[0187] Among them, in formula 8-1 to formula 8-5,
[0188] X 81 Can be selected from O, S, N (R 89 ) and C(R 89 )(R 90 ),
[0189] R 81 To R 90 can be independently selected from hydrogen, deuterium, C 1 -C 20 alkyl, phenyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl, and
[0190] *Indicates the binding site with the neighboring atoms.
[0191] In one embodiment, the first compound may be represented by one of Formula 1-1 to Formula 1-9:
[0192]
[0193]
[0194] Among them, in Formula 1-1 to Formula 1-9,
[0195] L 11 、a11、A 11 and R 11 To R 19 Each can be understood by referring to its corresponding description provided in Formula 1. That is, L 11 、a11、A 11 and R 11 To R 19 They may be the same as those defined in Formula 1.
[0196] For example, L in Equation 2 21 To L 23 Can be independently selected from:
[0197] Phenyl, naphthyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, phenanthrenyl, pyrenyl, yl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; and
[0198] phenyl, naphthyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, phenanthrenyl, pyrenyl, yl, peryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl: deuterium, -F, cyano, C 1 -C20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, indenofluorenyl, indolefluorenyl, benzofuranofluorenyl, benzothiophenefluorenyl, indenocarbazolyl, indolecarbazolyl, benzofuranocarbazolyl, benzothiophenecarbazolyl, indenodibenzofuranyl, indoledibenzofuranyl, benzofuranodibenzofuranyl, benzo thienodibenzofuranyl, indenodibenzothienyl, indoledibenzothienyl, benzofuranodibenzothienyl, benzothienodibenzothienyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, naphthyridinyl, quinoxalinyl, quinazolinyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl and diazadibenzothienyl.
[0199] For example, a21 to a23 in Formula 2 may each independently be 0 or 1.
[0200] For example, R in Formula 2 21 To R 23 Can be independently selected from:
[0201] phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, phenanthrenyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, benzoquinoxalinyl, benzoquinazolinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothienyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl, and diazadibenzothienyl;
[0202] phenyl, biphenyl, naphthyl, phenaltenyl, anthracenyl, phenanthryl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, benzoquinoxalinyl, benzoquinazolinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl and diazadibenzothiophenyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C10 Alkyl, C 1 -C 10 alkoxy, phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, phenanthrenyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, benzoquinoxalinyl, benzoquinazolinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothienyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl, diazadibenzothienyl, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 )、-N(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) and -P(=S)(Q 31 )(Q 32 );as well as
[0203] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ),and
[0204] Q 1 To Q 3 and Q 31 To Q 33 The phenyl group may be independently selected from phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, phenanthrenyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, benzoquinoxalinyl, benzoquinazolinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothienyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl and diazadibenzothienyl.
[0205] In one embodiment, R in Formula 2 21 To R 23 may be independently selected from phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, phenanthrenyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl, each of which is unsubstituted or substituted with at least one of the following: deuterium, C 1 -C 10 Alkyl, phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, phenanthrenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, -C(Q 31 )(Q 32 )(Q 33 ) and -Si(Q 31 )(Q 32 )(Q 33 );as well as
[0206] -C(Q 1 )(Q 2 )(Q 3 ) and -Si(Q 1 )(Q 2 )(Q 3 ),and
[0207] Q 1 To Q 3 and Q 31 To Q 33 The groups may be each independently selected from phenyl, biphenyl, naphthyl, phenalkenyl, anthracenyl, phenanthrenyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl.
[0208] In one embodiment, R selected from Formula 2 21 To R 23 At least one of the groups may be selected from the group represented by Formula 2A, the group represented by Formula 2B, -C(Q 1 )(Q 2 )(Q3 ) and -Si(Q 1 )(Q 2 )(Q 3 ):
[0209]
[0210] Wherein, in Formula 2A and Formula 2B,
[0211] Y 21 It can be selected from phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, phenanthrenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, -C(Q 31 )(Q 32 )(Q 33 ) and -Si(Q 31 )(Q 32 )(Q 33 ),
[0212] R 24 To R 27 can be independently selected from hydrogen, deuterium, C 1 -C 10 Alkyl, phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, phenanthrenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, -C(Q 31 )(Q 32 )(Q 33 ) and -Si(Q 31 )(Q 32 )(Q 33 ),
[0213] Q 1 To Q 3 and Q 31 To Q 33 may be each independently selected from phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, phenanthrenyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl, and
[0214] *Indicates the binding site with the neighboring atoms.
[0215] For example, M in Equation 3 31 It can be selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm).
[0216] For example, M in Equation 3 31 It can be Pt or Ir.
[0217] For example, A in Formula 3A to Formula 3D31 To A 34 may each independently be: i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed to each other, iv) a condensed ring in which two or more second rings are condensed to each other, or v) a condensed ring in which one or more first rings and one or more second rings are condensed to each other;
[0218] The first ring can be selected from cyclopentane, cyclopentene, cyclopentadiene, furan, thiophene, pyrrole, borole, phosphole, silole, germanol, selenophene, oxazole, dihydrooxazole, isoxazole, dihydroisoxazole, oxadiazole, dihydrooxadiazole, isoxadiazole, dihydroisoxadiazole, oxatriazole, dihydrooxatriazole, isoxatriazole, dihydroisoxatriazole, thiazole, dihydrothiazole, isothiazole, dihydroisothiazole, thiadiazole, dihydrothiadiazole, isothiadiazole, dihydroisothiadiazole, thiatriazole, dihydrothiatriazole, isothiatriazole, dihydroisothiatriazole, pyrazole, dihydropyrazole, imidazole, dihydroimidazole, triazole, dihydrotriazole, tetrazole, dihydrotetrazole, azasilole, diazasilole and triazasilole.
[0219] The second ring may be selected from cyclohexane, cyclohexene, cyclohexadiene, adamantane, norbornene, norbornene, benzene, pyridine, dihydropyridine, tetrahydropyridine, pyrimidine, dihydropyrimidine, tetrahydropyrimidine, pyrazine, dihydropyrazine, tetrahydropyrazine, pyridazine, dihydropyridazine, tetrahydropyridazine and triazine.
[0220] In one embodiment, A in Formula 3A to Formula 3D 31 To A 34 can be independently selected from benzene, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, Furan, thiophene, silapentyl, indene, fluorene, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, benzosilapentyl, dibenzosilapentyl, indole, carbazole, indenopyridine, indolepyridine, benzofuranopyridine, benzothienopyridine, benzosilapentylpyridine, indenopyrimidine, indolepyrimidine, benzofuranopyrimidine, benzothienopyrimidine, benzosilapentylpyrimidine, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline , quinazoline, cinnoline, phthalazine, phenanthroline, pyrrole, pyrazole, imidazole, dihydroimidazole, triazole, dihydrotriazole, oxazole, dihydrooxazole, isoxazole, thiazole, dihydrothiazole, isothiazole, oxadiazole, dihydrooxadiazole, thiadiazole, dihydrothiadiazole, benzopyrazole, benzimidazole, dihydrobenzimidazole, imidazopyridine, imidazopyrimidine, imidazopyrazine, benzoxazole, dihydrobenzoxazole, benzothiazole, dihydrobenzothiazole, benzoxadiazole, dihydrobenzoxadiazole, benzothiadiazole and dihydrobenzothiadiazole.
[0221] For example, T in Formula 3A to Formula 3D31 To T 34 can be independently selected from a single bond, a double bond, *-O-*', *-S-*', *-C(R 35 )(R 36 )-*' and *-N(R 35 )-*'.
[0222] For example, Y in Formula 3A to Formula 3D 31 To Y 34 may each be independently selected from a single bond, *-O-*' and *-S-*'.
[0223] For example, R in Formula 3A to Formula 3D 31 To R 38 Can be independently selected from:
[0224] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;
[0225] Phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl, quinazolinyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl and diazadibenzothiophenyl;
[0226] phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl, quinazolinyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl and diazadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl, quinazolinyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl, and diazadibenzothiophenyl; and
[0227] -B(Q 1 )(Q 2 ) and -N(Q 1 )(Q 2 ),and
[0228] Q 1 and Q 2 Can be independently selected from:
[0229] Hydrogen, deuterium and C 1 -C 20 alkyl;
[0230] Phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl, quinazolinyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl, and diazadibenzothiophenyl; and
[0231] phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl, quinazolinyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl and diazadibenzothiophenyl: deuterium, C 1 -C 20Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, The invention also includes but is not limited to benzofuranyl, benzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl, quinazolinyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl and diazadibenzothiophenyl.
[0232] In one embodiment, R in Formula 3A to Formula 3D 31 To R 38 Can be independently selected from:
[0233] hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy, ethoxy, propoxy, and butoxy;
[0234] Phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, 1-Benzene, 2-Benzene, 3-Benzene, 4-Benzene, 5-Benzene, 6-Benzene, 7-Benzene, 8-Benzene;
[0235] Phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, each substituted with at least one of the following yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy, ethoxy, propoxy, butoxy, phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, 1-Benzene, 2-Benzene, 3-Benzene, 4-Benzene, 5-Benzene, 6-Benzene, 7-Benzene, 8-Benzene, 9-Benzene, 10-Benzene, 11-Benzene, 12-Benzene, 13-Benzene, 14-Benzene, 15-Benzene, 16-Benzene, 17-Benzene, 18-Benzene, 19-Benzene, 20
[0236] -B(Q 1 )(Q 2 ) and -N(Q 1 )(Q 2 ),and
[0237] Q 1 and Q 2 Can be independently selected from:
[0238] hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl;
[0239] Phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, 1-Benzene, 2-Benzene, 3-Benzene, 4-Benzene, 5-Benzene, 6-Benzene, 7-Benzene, 8-Benzene, 9-Benzene, 10-Benzene, 11-Benzene, 12-Benzene, 13-Benzene, 14-Benzene, 15-Benzene, 16-Benzene, 17-Benzene, 18-Benzene, 19-Benzene, 21-Benzene, 22-Benzene, 23-Benzene, 24-Benzene, 25-Benzene, 26-Benzene, 27-Benzene, 28-Benzene, 29-Benzene, 30-Benzene, 31-Benzene, 32-Benzene, 33-Benzene, 34-Benzene, 35-Benzene, 36-Benzene, 37-Benzene, 38-Benzene, 39-Benz
[0240] Phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, each substituted with at least one of the following yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl: deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, The following are some of the following: 1) 2) 4) 6) 1) 2) 4 ...
[0241] In one embodiment, the third compound may be represented by one of the following Formula 3-1 and Formula 3-2:
[0242]
[0243] In formula 3-1 and formula 3-2,
[0244] X 31 To X 40 may be each independently selected from N and C, and
[0245] The remaining components can each be understood by referring to their respective descriptions provided above in conjunction with Formula 3.
[0246] In equations 3-1 and 3-2, X 31 and X 32 Can be independently A 31 A ring member of 33 To X 40 Each can be understood by referring to the description provided in conjunction with Formula 3-1 and Formula 3-2. That is, X 33 To X 40 They may each independently be N or C.
[0247] For example, A in Formula 4-1 to Formula 4-3 41 and A 42 Each independently selected from the group represented by formula 12, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 ) and -N(Q 1 )(Q 2 ):
[0248] Formula 12
[0249]
[0250] Among them, in formula 12,
[0251] X 121 Can be selected from O, S, N (R 123 ) and C(R 123 )(R 124 ),
[0252] X 122 can be selected from single bonds, O, S, N(R 125 ) and C(R 125 )(R 126 ),
[0253] A 121 and A 122 can be independently selected from phenyl, naphthyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, phenanthrenyl, pyrenyl, yl, peryl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl,
[0254] R 121 To R 126 Can be independently selected from:
[0255] Binding site, hydrogen, deuterium, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, -Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 ) and -N(Q 31 )(Q 32 );as well as
[0256] phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl and dinaphthothiophenyl: deuterium, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, -Si(Q 21 )(Q 22 )(Q 23 )、-B(Q 21 )(Q 22 ) and -N(Q 21 )(Q 22 ), where R 123 and R 124 may be optionally linked to each other to form a ring group that does not contain a π-electron-depleted nitrogen, R 125 and R 126 may be optionally linked to each other to form a ring group that does not contain π-electron-depleted nitrogen and is selected from R 121 To R 126 At least one of them is a binding site, and
[0257] b121 and b122 can be each independently selected from 1, 2, 3, 4, 5 and 6,
[0258] Where Q 1 To Q 3 , Q 21 To Q 23 and Q 31 To Q 33 Each can be understood by referring to the description thereof provided above.
[0259] In one or more embodiments, A in Formula 4-1 to Formula 4-3 41 and A 42 Each independently selected from the group represented by formula 12 and -N(Q 1 )(Q 2 ):
[0260] Formula 12
[0261]
[0262] Among them, in formula 12,
[0263] X 121 Can be selected from O, S, N (R 123 ) and C(R 123 )(R 124 ),
[0264] X 122 can be selected from single bonds, O, S, N(R 125 ) and C(R 125 )(R 126 ),
[0265] A 121 and A 122 may be independently selected from phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl,
[0266] R 121 To R 126 Can be independently selected from:
[0267] Binding site, hydrogen, deuterium, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl and -N(Q 31 )(Q 32 );as well as
[0268] Phenyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl, each substituted by at least one selected from the group consisting of deuterium, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl and -N(Q 21 )(Q 22 ), where R 123 and R 124 may be optionally linked to each other to form a ring group that does not contain a π-electron-depleted nitrogen, R 125 and R 126 may be optionally linked to each other to form a ring group that does not contain π-electron-depleted nitrogen and is selected from R 121 To R 126 At least one of them is a binding site, and
[0269] b121 and b122 can be each independently selected from 1, 2, 3, 4, 5 and 6,
[0270] Where Q 1 To Q 3 , Q 21 To Q 23 and Q 31 To Q 33 Each can be understood by referring to the description thereof provided above.
[0271] For example, D in Formula 4-1 to Formula 4-3 41 and D 42 Can be independently selected from:
[0272] -F, cyano, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl, quinazolinyl, and a group represented by one of the following formulas 13-1 to 13-3;
[0273] pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl and quinazolinyl, each substituted with at least one selected from the group consisting of deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl and quinazolinyl;
[0274] pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl and quinazolinyl, each independently selected from deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, substituted with at least one of 1,2-diphenyl-2-oxo- ... 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl and quinazolinyl;
[0275] Each of the following C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, 1-F, cyano, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl and quinazolinyl;
[0276] Each of the following C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl and dinaphthothiophenyl: each independently selected from deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridyl, pyrazinyl , pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl and quinazolinyl substituted with at least one of pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl and quinazolinyl; and
[0277] Each of the following C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, 1-F, cyano, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl and quinazolinyl substituted with at least one C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, 1-Benzene, 2 ...
[0278]
[0279] Among them, in Formula 13-1 to Formula 13-3,
[0280] X 131 Can be selected from C(=O), S(=O), S(=O) 2 ,P(=O)(R 134 ) and P(=S)(R 134 ),
[0281] X 132Can be selected from O, S, C(=O), S(=O), S(=O) 2 ,P(=O)(R 135 ) and P(=S)(R 135 ),
[0282] k132 can be 0 or 1. When k132 is 0, -(X 132 ) k132 - does not exist. That is, when k132 is 0, -(X 132 ) k132 - for direct connection.
[0283] Y 131 can be selected from O and S,
[0284] A 131 and A 132 can be independently selected from phenyl, naphthyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, phenanthrenyl, pyrenyl, yl, peryl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl,
[0285] R 131 To R 135 Can be independently selected from:
[0286] Binding site, hydrogen, deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl, and quinazolinyl; and
[0287] Each of the following C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl and quinazolinyl: deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, 1-(4-nitrophenyl)-2-oxo-1-oxo-2-oxo-1-oxo-2-oxo-2-oxo-3-oxo-4-nitro ... 131 To R 135 At least one of them is a binding site, and
[0288] b131 and b132 may each be independently selected from 1, 2, 3, 4, 5 and 6.
[0289] In one or more embodiments, D in Formula 4-1 to Formula 4-3 41 and D 42 Can be independently selected from:
[0290] -F, cyano, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, and a group represented by one of Formula 13-1 to Formula 13-3;
[0291] pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl and triazinyl, each substituted by at least one selected from the group consisting of deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl and triazinyl;
[0292] pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl and triazinyl, each substituted by at least one selected from the group consisting of deuterium, -F, cyano, C 1 -C 20C substituted by at least one of alkyl, phenyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl and triazinyl 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl and triazinyl;
[0293] phenyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl, each of which is substituted by at least one selected from the group consisting of -F, cyano, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl and triazinyl; 1 -C 20 Alkyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl and triazinyl;
[0294] Phenyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl, each substituted by at least one selected from the group consisting of deuterium, -F, cyano, C 1 -C 20 alkyl, phenyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl and triazinyl substituted with at least one of pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl and triazinyl; and
[0295] Each of the following C 1 -C 20 Alkyl, phenyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl: each independently substituted by at least one selected from -F, cyano, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl and triazinyl. 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl:
[0296]
[0297] Among them, in Formula 13-1 to Formula 13-3,
[0298] X 131 Can be selected from C(=O), S(=O), S(=O) 2 ,P(=O)(R 134 ) and P(=S)(R 134 ),
[0299] X 132 Can be selected from O, S, C(=O), S(=O), S(=O) 2 ,P(=O)(R135 ) and P(=S)(R 135 ),
[0300] k132 can be 0 or 1. When k132 is 0, -(X 132 ) k132 - does not exist. That is, when k132 is 0, -(X132) k132 - for direct connection.
[0301] Y 131 can be selected from O and S,
[0302] A 131 and A 132 may be independently selected from phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl,
[0303] R 131 To R 135 Can be independently selected from:
[0304] Binding site, hydrogen, deuterium, -F, cyano, C 1 -C 20 alkyl, phenyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl, and quinazolinyl; and
[0305] Each of which is substituted by at least one selected from the following: C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl and triazinyl: deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl and triazinyl, wherein R is selected from 131 To R 135 At least one of them is a binding site, and
[0306] b131 and b132 may each be independently selected from 1, 2, 3, 4, 5 and 6.
[0307] For example, L in Formula 4-1 to Formula 4-3 41 and L 42 Can be independently selected from:
[0308] Phenyl, naphthyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, phenanthrenyl, pyrenyl, yl, peryl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, -C(Q 1 )(Q 2 )- and -Si(Q 1 )(Q 2 )-;as well as
[0309] phenyl, naphthyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, phenanthrenyl, pyrenyl, yl, peryl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl: deuterium, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, -C(Q 31 )(Q 32 )(Q 33 ) and -Si(Q 31 )(Q 32 )(Q 33 ),and
[0310] Q 1 , Q 2 and Q 31 To Q 33 Same as described above.
[0311] In one embodiment, L in Formula 4-1 to Formula 4-3 41 and L 42 Can be independently selected from:
[0312] Phenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, -C(Q 1 )(Q 2 )- and -Si(Q 1 )(Q 2 )-;as well as
[0313] Phenyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl, each substituted by at least one selected from the group consisting of deuterium, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, -C(Q 31 )(Q 32 )(Q 33 ) and -Si(Q 31 )(Q 32 )(Q33 ),and
[0314] Q 1 , Q 2 and Q 31 To Q 33 Same as described above.
[0315] In one embodiment,
[0316] The first compound may be selected from compounds of Group I,
[0317] The second compound may be selected from compounds of Group II,
[0318] The third compound may be selected from the compounds of Group III-I and Group III-II,
[0319] The fourth compound may be selected from compounds of Group IV:
[0320] Group I
[0321]
[0322]
[0323] Group II
[0324]
[0325]
[0326] Group III-I
[0327]
[0328]
[0329] Group III-II
[0330]
[0331]
[0332] Group IV
[0333]
[0334] In Group III-I, Compounds 1 to 5 are represented by the first structure of the group, wherein the substituent R is defined under the corresponding structure, respectively. Compounds 6 to 20, Compounds 29 to 48, and Compounds 57 to 76 are similarly defined.
[0335] The first compound, the second compound, and the third compound may not emit substantially light. For example, the first compound, the second compound, and the third compound may not emit any light, or the light emitted by the first compound, the second compound, and the third compound may have only a negligible amount compared to the light emitted by other compounds (e.g., the fourth compound).
[0336] More specifically, the third compound may not emit light, but reverse intersystem crossing (RISC) and / or intersystem crossing (ISC) may actively occur therein, thereby causing triplet excitons generated by the first and second compounds to be transferred to the fourth compound.
[0337] Therefore, by transferring singlet excitons and triplet excitons generated in the emission layer to the fourth compound, an organic light-emitting device with improved efficiency can be obtained. In addition, since an organic light-emitting device with significantly reduced energy loss is obtained, the lifespan characteristics of the organic light-emitting device can be improved.
[0338] In addition, since the excitons transition in the third compound and then transition in the fourth compound, degradation of the fourth compound due to the energy of the excitons can be suppressed, thereby improving life characteristics.
[0339] The lowest excited triplet energy level of the third compound may be about 2.5 eV to about 3.5 eV. Therefore, the lowest excited triplet energy level of the third compound is higher than the lowest excited singlet energy level of the fourth compound, so that the lowest triplet exciton of the third compound can be easily transferred to the lowest excited singlet energy level of the fourth compound.
[0340] The fourth compound emits light, and the fourth compound may be a delayed fluorescent emitter. That is, the fourth compound is configured to emit light, and the fourth compound may be a delayed fluorescent emission material.
[0341] In one or more embodiments, the fourth compound may be a thermally activated delayed fluorescence (TADF) emitter.
[0342] In one or more embodiments, the ratio of the luminescent component emitted from the fourth compound to the total luminescent component emitted from the emission layer may be 80% or more. That is, the ratio of the light emitted from the fourth compound to the total light emitted from the emission layer may be 80% or more.
[0343] The fourth compound may have a maximum emission wavelength in the range of about 450 nm to about 490 nm, but embodiments of the present disclosure are not limited thereto.
[0344] More specifically, the fourth compound in the emission layer may emit blue delayed fluorescence by receiving energy from excitons (formed in other compounds) without directly participating in the formation of excitons.
[0345] The fourth compound may satisfy condition 1:
[0346] Condition 1
[0347] △E ST (C4)≤0.3eV.
[0348] In condition 1,
[0349] △E ST (C4) is the lowest excited singlet energy level (E S1 (C4)) and the lowest excited triplet energy level (E T1 (C4)).
[0350] Here, E S1 (C4) and E T1 (C4) Each can be evaluated using the density functional theory (DFT) method of the Gaussian program with structure optimization at the B3LYP / 6-31G(d,p) level.
[0351] The T1 level of the fourth compound is much higher than the T1 level in the related art (e.g., typical) fluorescent dopant, so that reverse intersystem crossing (RISC) can be achieved by heating. In the case of the related art (e.g., typical) fluorescent dopant, its T1 level is significantly lower than the T1 level of the phosphorescent dopant, so that the excitons at the T1 level generated by the phosphorescent dopant are actively energy-transferred to the T1 level of the related art (e.g., typical) fluorescent dopant, and may be quenched after energy transfer without participating in light emission. In addition, since the T1 level of the fluorescent dopant is low, the triplet excitons generated in the first compound and the second compound may be quenched without participating in light emission while being transferred to the T1 level of the fluorescent dopant instead of the T1 level of the phosphorescent dopant. Therefore, it is inappropriate to use a fluorescent dopant. However, because the fourth compound has a sufficiently high RISC efficiency even at room temperature, even when the excitons at the T1 level of the phosphorescent dopant move to the T1 level of the delayed fluorescent dopant, the excitons at the T1 level of the delayed fluorescent dopant can reversely intersystem cross to the S1 level of the delayed fluorescent dopant, and then can be emitted as fluorescence. In other words, the excitons are not quenched. Therefore, the possibility of exciton quenching can be reduced (e.g., greatly reduced), thereby significantly (e.g., greatly) increasing the luminous efficiency, and because the excitons are transferred from the phosphorescent dopant to the delayed fluorescent dopant, the degradation of the delayed fluorescent dopant due to the exciton energy is suppressed or reduced, and the life characteristics can also be improved.
[0352] The second compound contains a triazine core, and therefore, the second compound has a high T1 energy, thereby reducing or preventing triplet quenching and triplet-triplet annihilation.
[0353] Generally, when electrons are not smoothly (e.g., efficiently) provided from the electron transport region to the emission layer, charges accumulate at the interface between the emission layer and the electron transport region, and the interface deteriorates. On the other hand, when holes are not smoothly (e.g., efficiently) provided from the hole transport region to the emission layer, charges accumulate at the interface between the emission layer and the hole transport region, and the interface deteriorates, thereby reducing the life of the organic light-emitting device.
[0354] Because the second compound includes an electron transport portion, the electron transport properties of the organic light-emitting device can be adjusted using (e.g., easily used) the second compound, and because the first compound does not include an electron transport portion, the hole transport properties of the organic light-emitting device can be adjusted using (e.g., easily used) the first compound. Therefore, the charge balance in the emission layer of the organic light-emitting device can be improved or optimized.
[0355] The first compound in the emission layer may be about 10 wt % to about 90 wt % based on the total weight of the emission layer.
[0356] The second compound in the emission layer may be about 10 wt % to about 90 wt % by weight based on the total weight of the emission layer.
[0357] The amount of the third compound in the emission layer may be greater than or equal to the amount of the fourth compound.
[0358] The fourth compound in the emission layer may be about 0.25 wt % to about 5 wt % by weight based on the total weight of the emission layer.
[0359] The amount of the fourth compound may be about 0.01 parts by weight to about 20 parts by weight per 100 parts by weight of the total amount of the first compound and the second compound.
[0360] When the first compound, the second compound, the third compound, and the fourth compound satisfy the above ranges, an organic light-emitting device having improved efficiency and lifespan may be obtained.
[0361] The amount of the first compound and the second compound may be greater than the amount of the third compound and the fourth compound.
[0362] In one embodiment, the emission layer may include a first compound, a second compound, a third compound, and a fourth compound, but embodiments of the present disclosure are not limited thereto. For example, the emission layer may be composed of a first compound, a second compound, a third compound, and a fourth compound (for example, it may only include the first compound, the second compound, the third compound, and the fourth compound), but embodiments of the present disclosure are not limited thereto.
[0363] In one embodiment, the first electrode is an anode, the second electrode is a cathode, and the organic layer further includes a hole transport region between the first electrode and the emission layer and / or an electron transport region between the emission layer and the second electrode, wherein the hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer and / or an electron blocking layer, and the electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer and / or an electron injection layer, but the embodiments of the present disclosure are not limited thereto.
[0364] For example, the hole blocking layer may include a hole blocking material represented by Formula 2.
[0365] The hole blocking material may be understood by referring to the description of Formula 2 above.
[0366] The hole blocking material may be selected from Group II above.
[0367] Figure 1 Description
[0368] Figure 1 is a schematic diagram of an organic light-emitting device 10 in one embodiment. The organic light-emitting device 10 includes a first electrode 110 , an organic layer 150 , and a second electrode 190 .
[0369] In the following, we will combine Figure 1 A structure of an organic light emitting device 10 according to an embodiment and a method of manufacturing the same according to an embodiment are described.
[0370] First electrode 110
[0371] refer to Figure 1 , a substrate may be additionally located below the first electrode 110 or above the second electrode 190. The substrate may be a glass substrate or a plastic substrate, each having suitable (eg, excellent) mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and / or waterproofness.
[0372] For example, the first electrode 110 may be formed by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be selected from materials having a high work function to facilitate hole injection.
[0373] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and any combination thereof, but the embodiments of the present disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode 110 may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but the embodiments of the present disclosure are not limited thereto.
[0374] The first electrode 110 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited thereto.
[0375] Organic layer 150
[0376] The organic layer 150 is disposed on the first electrode 110. The organic layer 150 may include an emission layer.
[0377] The organic layer 150 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 190 .
[0378] Hole transport region in the organic layer 150
[0379] The hole transport region may have i) a single-layer structure including a single layer including a single material, ii) a single-layer structure including a single layer including a plurality of different materials, or iii) a multi-layer structure having a plurality of layers including a plurality of different materials.
[0380] The hole transport region may include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an emission assisting layer, and an electron blocking layer.
[0381] For example, the hole transport zone may have a single-layer structure or a multi-layer structure, the single-layer structure including a single layer (including a plurality of different materials), the multi-layer structure having a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure or a hole injection layer / hole transport layer / emission auxiliary layer structure, wherein for each structure, the constituent layers are stacked in sequence from the first electrode 110 in the order stated, but the structure of the hole transport zone is not limited thereto.
[0382] In one embodiment, the hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201 below, and a compound represented by Formula 202 below:
[0383]
[0384] Formula 201
[0385]
[0386] Formula 202
[0387]
[0388] In equation 201 and equation 202,
[0389] L 201 To L 204 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0390] L 205 Can be selected from *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C 1 -C 20 Alkylene, substituted or unsubstituted C 2 -C 20 Alkenylene, substituted or unsubstituted C3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0391] xa1 to xa4 may each independently be an integer selected from 0 to 3,
[0392] xa5 may be an integer selected from 1 to 10, and
[0393] R 201 To R 204 and Q 201 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
[0394] For example, in Equation 202, R 201 and R 202 may be optionally linked to each other via a single bond, a dimethyl-methylene group or a diphenyl-methylene group, and R 203 and R 204 They may optionally be linked to one another via single bonds, dimethyl-methylene or diphenyl-methylene groups.
[0395] In one embodiment, in equation 201 and equation 202,
[0396] L 201 To L 205 Can be independently selected from:
[0397] Phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-difluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, pyrenylene phenylene, tetraphenylene, perylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, rubidinylene, coronene, ovaphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene, and pyridinylene; and
[0398] each substituted with at least one selected from the group consisting of phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, pyrenylene, phenylene, tetraphenylene, perylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, rubidinyl, coronene, ovaphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene and pyridinylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 Alkyl-substituted phenyl, -F-substituted phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, corynyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ),
[0399] Where Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0400] In one or more embodiments, xa1 to xa4 may each independently be 0, 1 or 2.
[0401] In one or more embodiments, xa5 can be 1, 2, 3 or 4.
[0402] In one or more embodiments, R 201 To R 204 and Q 201 Can be independently selected from:
[0403] Phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrene, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, corynyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, and pyridyl; and
[0404] phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, corynyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl and pyridyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 Alkyl-substituted phenyl, -F-substituted phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, corynyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ),and
[0405] Q 31 To Q 33 Same as described above.
[0406] In one or more embodiments, R selected from Formula 201 201 and R 203 At least one of can be independently selected from:
[0407] fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl; and
[0408] Fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C1 -C 10 alkyl-substituted phenyl, -F-substituted phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl,
[0409] However, the embodiments of the present disclosure are not limited thereto.
[0410] In one or more embodiments, in Formula 202, i) R 201 and R 202 may be linked to each other via a single bond, and / or ii) R 203 and R 204 can be connected to each other via a single bond.
[0411] In one or more embodiments, R in Formula 202 201 To R 204 Can be independently selected from:
[0412] carbazolyl; and
[0413] A carbazolyl group substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 alkyl-substituted phenyl, -F-substituted phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl,
[0414] However, the embodiments of the present disclosure are not limited thereto.
[0415] The compound represented by Formula 201 can be represented by Formula 201-1:
[0416] Formula 201-1
[0417]
[0418] In one embodiment, the compound represented by Formula 201 may be represented by Formula 201-2, but embodiments of the present disclosure are not limited thereto:
[0419] Formula 201-2
[0420]
[0421] In one or more embodiments, the compound represented by Formula 201 may be represented by the following Formula 201-2(1), but the embodiments of the present disclosure are not limited thereto:
[0422] Formula 201-2(1)
[0423]
[0424] In one or more embodiments, the compound represented by Formula 201 may be represented by the following Formula 201A:
[0425] Formula 201A
[0426]
[0427] In one or more embodiments, the compound represented by Formula 201 may be represented by the following Formula 201A(1), but the embodiments of the present disclosure are not limited thereto:
[0428] Formula 201A(1)
[0429]
[0430] In one or more embodiments, the compound represented by Formula 201 may be represented by the following Formula 201A-1, but the embodiments of the present disclosure are not limited thereto:
[0431] Formula 201A-1
[0432]
[0433] In one embodiment, the compound represented by Formula 202 may be represented by the following Formula 202-1:
[0434] Formula 202-1
[0435]
[0436] In one or more embodiments, the compound represented by Formula 202 may be represented by the following Formula 202-1(1):
[0437] Formula 202-1(1)
[0438]
[0439] In one or more embodiments, the compound represented by Formula 202 may be represented by the following Formula 202A:
[0440] Formula 202A
[0441]
[0442] In one or more embodiments, the compound represented by Formula 202 may be represented by the following Formula 202A-1:
[0443] Formula 202A-1
[0444]
[0445] In equation 201-1, equation 201-2, equation 201-2(1), equation 201A, equation 201A(1), equation 201A-1, equation 202-1, equation 202-1(1), equation 202A, and equation 202A-1,
[0446] L 201 To L 203 , xa1 to xa3, xa5 and R 202 To R 204 can each be understood by reference to the corresponding description thereof provided above,
[0447] L 205 may be selected from phenylene and fluorenylene,
[0448] X 211 Can be selected from O, S and N (R 211 ),
[0449] X 212 Can be selected from O, S and N (R 212 ),
[0450] R 211 and R 212 Each can be combined with R by reference 203 The description presented is understood, and
[0451] R 213 To R 217 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 Alkyl-substituted phenyl, -F-substituted phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, corynyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl and pyridyl.
[0452] The hole transport region may include at least one compound selected from Compound HT1 to Compound HT48, but the embodiments of the present disclosure are not limited thereto:
[0453]
[0454]
[0455]
[0456]
[0457]
[0458] The thickness of the hole transport region can be about to about For example, about to about When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be in the range of about to about For example, about to about and the thickness of the hole transport layer can be in the range of about to about For example, about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics may be obtained without significantly increasing the driving voltage.
[0459] The emission auxiliary layer may increase light emission efficiency by compensating the optical resonance distance according to the wavelength of light emitted by the emission layer, and the electron blocking layer may block the flow of electrons from the electron transport region. The emission auxiliary layer and the electron blocking layer may include the above-mentioned materials.
[0460] p-dopant
[0461] In addition to these materials, the hole transport region may further include a charge generating material for improving the conductive characteristics. The charge generating material may be dispersed uniformly or non-uniformly in the hole transport region.
[0462] The charge generating material may be, for example, a p-dopant.
[0463] In one embodiment, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of -3.5 eV or less.
[0464] The p-type dopant may include at least one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but the embodiments of the present disclosure are not limited thereto.
[0465] For example, the p-dopant may include at least one selected from the following:
[0466] Quinone derivatives (such as tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ));
[0467] Metal oxides (such as tungsten oxide and / or molybdenum oxide);
[0468] 1,4,5,8,9,12-Hexaazabenzo[9,10]phenanthrene-hexacarbonitrile (HAT-CN); and
[0469] A compound represented by the following formula 221,
[0470] However, the embodiments of the present disclosure are not limited thereto:
[0471]
[0472] Formula 221
[0473]
[0474] In formula 221,
[0475] R 221 To R 223 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, wherein R is selected from 221 To R223 At least one of the following may have at least one substituent selected from the group consisting of cyano, -F, -Cl, -Br, -I, C substituted with -F 1 -C 20 Alkyl, C substituted by -Cl 1 -C 20 Alkyl, C substituted by -Br 1 -C 20 Alkyl and C substituted by -I 1 -C 20 alkyl.
[0476] Emission layer in the organic layer 150
[0477] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer can be patterned into a red emission layer, a green emission layer, or a blue emission layer according to the sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, wherein the two or more layers are in contact with each other or separated from each other. In one or more embodiments, the emission layer may include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light.
[0478] The thickness of the emission layer can be about to about For example, about to about When the thickness of the emission layer is within these ranges, suitable (eg, excellent) light emission characteristics may be obtained without significantly increasing the driving voltage.
[0479] Electron transport region in the organic layer 150
[0480] The electron transport region may have i) a single-layer structure including a single layer including a single material, ii) a single-layer structure including a single layer including a plurality of different materials, or iii) a multi-layer structure having a plurality of layers including a plurality of different materials.
[0481] The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but embodiments of the present disclosure are not limited thereto.
[0482] For example, the electron transport region may have a structure of an electron transport layer / electron injection layer, a structure of a hole blocking layer / electron transport layer / electron injection layer, a structure of an electron control layer / electron transport layer / electron injection layer, or a structure of a buffer layer / electron transport layer / electron injection layer, wherein for each structure, the constituent layers are stacked sequentially from the emission layer in the order stated. However, the embodiment of the structure of the electron transport region is not limited thereto.
[0483] The electron transport region (eg, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one ring containing π-electron-depleted nitrogen.
[0484] As used herein, the term "π-electron-depleted nitrogen-containing ring" refers to a C-type ring having at least one *-N=*' moiety as a ring-forming part. 1 -C 60 Heterocyclic group.
[0485] For example, the “π-electron-depleted nitrogen-containing ring” may be i) a five- to seven-membered heteromonocyclic group having at least one *-N=*' moiety, ii) a heteropolycyclic group in which two or more five- to seven-membered heteromonocyclic groups each having at least one *-N=*' moiety are fused to each other, or iii) a heteropolycyclic group in which at least one five- to seven-membered heteromonocyclic group each having at least one *-N=*' moiety is fused to at least one C 5 -C 60 The carbocyclic group is fused.
[0486] Examples of rings containing π-electron-depleted nitrogen include imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl, but are not limited thereto.
[0487] For example, the electron transport region may include a compound represented by the following Formula 601:
[0488] Formula 601
[0489] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0490] In formula 601,
[0491] Ar 601 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,
[0492] xe11 can be 1, 2 or 3,
[0493] L 601 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0494] xe1 may be an integer selected from 0 to 5,
[0495] R 601 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q601 )、-S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),
[0496] Q 601 To Q 603 Can be independently C 1 -C 10 Alkyl, C 1 -C 10 alkoxy, phenyl, biphenyl, terphenyl or naphthyl, and
[0497] xe21 may be an integer selected from 1 to 5.
[0498] In one embodiment, the number of Ar is xe11 601 and the number of R is xe21 601 At least one of the may include a ring containing π-electron-depleted nitrogen.
[0499] In one embodiment, Ar in Formula 601 601 Can be selected from:
[0500] Phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrene, yl, naphthacene, phenanthrenyl, peryl, pentaphenanthrenyl, indenoanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0501] phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, each substituted by at least one selected from the following yl, naphthacene, peryl, peryl, pentaphenyl, indenoanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, Cinoline, phenanthridinyl, acridinyl, phenanthroline, phenazine, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),
[0502] Where Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0503] When xe11 in Formula 601 is 2 or greater, two or more Ar 601 can be connected to each other via a single bond.
[0504] In one or more embodiments, Ar in Formula 601 601 It may be anthracene.
[0505] In one or more embodiments, the compound represented by Formula 601 may be represented by the following Formula 601-1:
[0506] Formula 601-1
[0507]
[0508] In formula 601-1,
[0509] X 614 Can be N or C (R 614 ), X 615 Can be N or C (R615 ), X 616 Can be N or C (R 616 ), and selected from X 614 To X 616 At least one of may be N,
[0510] L 611 To L 613 Each can be combined with L by reference 601 Provide description to understand,
[0511] xe611 to xe613 can each be understood by referring to the description provided in conjunction with xe1,
[0512] R 611 To R 613 Each can be combined with R by reference 601 Provide a description to understand, and
[0513] R 614 To R 616 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0514] In one embodiment, in Formula 601 and Formula 601-1, L 601 and L 611 To L 613 Can be independently selected from:
[0515] Phenylene, naphthylene, fluorenylene, spiro-difluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrene, pyrene yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazole ylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, benzisothiazolylene, benzoxazolylene, benzisoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidinylene, and azacarbazolylene; and
[0516] each substituted with at least one selected from the group consisting of phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, pyrenylene, yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene , triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrene, phenyl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl,
[0517] However, the embodiments of the present disclosure are not limited thereto.
[0518] In one or more embodiments, in Formula 601 and Formula 601-1, xe1 and xe611 to xe613 may each independently be 0, 1 or 2.
[0519] In one or more embodiments, in Formula 601 and Formula 601-1, R 601 and R 611 To R 613 Can be independently selected from:
[0520] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrene, phenyl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl;
[0521] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, each substituted by at least one selected from the following yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazine , quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrene, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazole yl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0522] -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),
[0523] Where Q 601 and Q 602 Same as described above.
[0524] The electron transport region may include at least one compound selected from the following compounds ET1 to ET36, but the embodiments of the present disclosure are not limited thereto:
[0525]
[0526]
[0527]
[0528]
[0529] In one or more embodiments, the electron transport region may include at least one compound selected from the group consisting of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (BPhen), Alq 3 , BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), NTAZ, and diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1):
[0530]
[0531]
[0532] The thickness of the buffer layer, hole blocking layer or electron control layer can be about to about For example, about to about When the thickness of the buffer layer, the hole blocking layer, or the electron control layer is within the above range, suitable (eg, excellent) hole blocking characteristics or electron control characteristics may be obtained without significantly increasing the driving voltage.
[0533] The thickness of the electron transport layer can be about to about For example, about to about When the thickness of the electron transport layer is within the above range, the electron transport layer may have satisfactory electron transport characteristics without significantly increasing the driving voltage.
[0534] In addition to the above materials, the electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material.
[0535] The metal-containing material may include at least one selected from an alkali metal complex and an alkaline earth metal complex. The alkali metal complex may include a metal ion selected from the following: Li ion, Na ion, K ion, Rb ion and Cs ion, and the alkaline earth metal complex may include a metal ion selected from the following: Be ion, Mg ion, Ca ion, Sr ion and Ba ion. The ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.
[0536] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, the following compounds ET-D1 (8-hydroxyquinoline lithium, LiQ) or ET-D2:
[0537]
[0538] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may directly contact the second electrode 190.
[0539] The electron injection layer may have i) a single-layer structure including a single layer including a single material, ii) a single-layer structure including a single layer including a plurality of different materials, or iii) a multi-layer structure having a plurality of layers including a plurality of different materials.
[0540] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0541] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal may be Li, Na, and / or Cs. In one or more embodiments, the alkali metal may be Li and / or Cs, but the embodiments of the present disclosure are not limited thereto.
[0542] The alkaline earth metal may be selected from Mg, Ca, Sr and Ba.
[0543] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb and Gd.
[0544] The alkali metal compound, alkaline earth metal compound and rare earth metal compound may be selected from oxides and halides (eg, fluorides, chlorides, bromides and / or iodides) of alkali metals, alkaline earth metals and rare earth metals.
[0545] The alkali metal compound can be selected from alkali metal oxides (such as Li 2 O, Cs 2 O or K 2 O) and alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI and / or KI). In one embodiment, the alkali metal compound can be selected from LiF, Li 2 O, NaF, LiI, NaI, CsI and KI, but the embodiments of the present disclosure are not limited thereto.
[0546] The alkaline earth metal compound can be selected from alkaline earth metal oxides, such as BaO, SrO, CaO, Ba x Sr 1-x O(0 < x < 1) and / or Ba x Ca 1-x O(0 < x < 1). In one embodiment, the alkaline earth metal compound can be selected from BaO, SrO and CaO, but the embodiments of the present disclosure are not limited thereto.
[0547] The rare earth metal compound can be selected from YbF 3 、ScF 3 、Sc 2 O 3 、Y 2 O 3 、Ce 2 O 3 、GdF 3 和TbF 3 。 In one embodiment, the rare earth metal compound can be selected from YbF 3 、ScF 3 、TbF 3 、YbI 3 、ScI 3 和TbI 3 , but the embodiments of the present disclosure are not limited thereto.
[0548] The alkali metal complex, alkaline earth metal complex and rare earth metal complex can include the alkali metal ions, alkaline earth metal ions and rare earth metal ions as described above, and the ligands coordinated with the metal ions of the alkali metal complex, alkaline earth metal complex or rare earth metal complex can be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.
[0549] The electron injection layer may include (e.g., be composed of): an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described above. In one or more embodiments, the electron injection layer may also include an organic material. When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix including an organic material.
[0550] The thickness of the electron injection layer can be about to about For example, about to about When the thickness of the electron injection layer is within the above range, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0551] The second electrode 190
[0552] The second electrode 190 may be disposed on the organic layer 150 having such a structure. The second electrode 190 may be a cathode as an electron injection electrode, and in this regard, a material for forming the second electrode 190 may be selected from metals, alloys, conductive compounds, and combinations thereof that may have a relatively low work function.
[0553] The second electrode 190 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, and IZO, but the embodiments of the present disclosure are not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0554] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.
[0555] Figures 2 to 4 Description
[0556] Figure 2 The organic light-emitting device 20 includes: a first cover layer 210, a first electrode 110, an organic layer 150, and a second electrode 190, which are sequentially stacked in the order stated; Figure 3 The organic light-emitting device 30 includes: a first electrode 110, an organic layer 150, a second electrode 190, and a second cover layer 220, which are sequentially stacked in the order stated; Figure 4The organic light emitting device 40 includes a first cover layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second cover layer 220, which are sequentially stacked in the stated order.
[0557] for Figures 2 to 4 , can be combined by reference Figure 1 The description is presented to understand the first electrode 110 , the organic layer 150 , and the second electrode 190 .
[0558] In the organic layer 150 of each of the organic light-emitting devices 20 and 40, light generated in the emission layer may pass through the first electrode 110 and the first cover layer 210 toward the outside, wherein the first electrode 110 may be a semi-transmissive electrode or a transmissive electrode. In the organic layer 150 of each of the organic light-emitting devices 30 and 40, light generated in the emission layer may pass through the second electrode 190 and the second cover layer 220 toward the outside, wherein the second electrode 190 may be a semi-transmissive electrode or a transmissive electrode.
[0559] According to the principle of constructive interference, the first cover layer 210 and the second cover layer 220 can increase external light emitting efficiency.
[0560] The first capping layer 210 and the second capping layer 220 may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material.
[0561] At least one selected from the first cover layer 210 and the second cover layer 220 may each independently include at least one material selected from the following: carbocyclic compounds, heterocyclic compounds, amine compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. Carbocyclic compounds, heterocyclic compounds, and amine compounds may be optionally substituted with a substituent containing at least one element selected from the following: O, N, S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one selected from the first cover layer 210 and the second cover layer 220 may each independently include an amine compound.
[0562] In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include a compound represented by Formula 201 or a compound represented by Formula 202.
[0563] In one or more embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include a compound selected from Compounds HT28 to HT33 and Compounds CP1 to CP5, but embodiments of the present disclosure are not limited thereto.
[0564]
[0565] In the above, it has been combined Figures 1 to 4 The organic light emitting device according to the embodiment is described, but the embodiments of the present disclosure are not limited thereto.
[0566] The layer constituting the hole transport region, the emission layer and the layer constituting the electron transport region can be formed in a certain region by utilizing one or more appropriate methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing and laser induced thermal imaging.
[0567] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition may be performed at a deposition temperature of about 100° C. to about 500° C., at a ... -8 To about 10 -3 Torr vacuum and approx. to about The deposition rate is carried out at .
[0568] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by spin coating, the spin coating may be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80°C to 200°C, taking into account the materials included in the layer to be formed and the structure of the layer to be formed.
[0569] equipment
[0570] The organic light emitting device may be included in various suitable devices.
[0571] More specifically, the apparatus may include: a thin film transistor including a source electrode, a drain electrode and an active layer; and an organic light emitting device. The first electrode of the organic light emitting device may be electrically connected to the source electrode or the drain electrode of the thin film transistor.
[0572] The thin film transistor may further include a gate electrode, a gate insulating layer, and / or the like.
[0573] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, or the like, but the embodiments of the present disclosure are not limited thereto.
[0574] The device may further include a sealing portion for sealing the organic light-emitting device. The sealing portion may allow an image from the organic light-emitting device to be displayed, and may block external air and moisture from penetrating into the organic light-emitting device. The sealing portion may be a sealing substrate including a transparent glass or plastic substrate. The sealing portion may be a thin film encapsulation layer including a plurality of organic layers and / or a plurality of inorganic layers. When the sealing unit is a thin film encapsulation layer, the entire device may be flexible.
[0575] For example, the device may be a lighting device, an authentication device, or an electronic device.
[0576] The light emitting device may be used as any suitable display, light source, and / or the like.
[0577] The authentication device may be, for example, a biometric authentication device for authenticating an individual by using biometric information of a living being (eg, fingertips, pupils, and / or the like). In addition to the organic light emitting device, the authentication device may further include a biometric information collector.
[0578] The electronic device can be applied to personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notepads, electronic dictionaries, electronic game consoles, medical instruments (e.g., electronic thermometers, blood pressure meters, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram (ECG) displays, ultrasonic diagnostic devices and / or endoscope displays), fish finders, various suitable measuring instruments, meters (e.g., meters for vehicles, aircraft and / or ships), projectors and / or the like, but the embodiments of the present disclosure are not limited thereto.
[0579] General Definition of Substituents
[0580] As used herein, the term "π-electron-depleted nitrogen-containing ring group" refers to a ring group having at least one *-N=*' moiety, for example, a C-1 ... 1 -C 60 Heterocyclic group. For example, the "π-electron-depleted nitrogen-containing ring" may be i) a five- to seven-membered heteromonocyclic group having at least one *-N=*' portion, ii) a heteropolycyclic group in which two or more five- to seven-membered heteromonocyclic groups each having at least one *-N=*' portion are fused to each other, or iii) a heteropolycyclic group in which at least one five- to seven-membered heteromonocyclic group each having at least one *-N=*' portion is fused to at least one C 5 -C 60The carbocyclic radical is fused, and non-limiting examples thereof include imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl.
[0581] As used herein, the term "ring group not containing a π-electron-depleted nitrogen" refers to a ring group not containing a *-N=*' moiety, and may be, for example, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, etc. The ring group not containing π-electron-depleted nitrogen can be selected from phenyl, biphenyl, terphenyl, heptalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, The invention also includes phenyl, tetraphenyl, peryl, peryl, pentacene, hexaphenyl, rubinyl, corynyl, ovalenyl, pyrrolyl, isoindolyl, indolyl, furyl, thienyl, benzofuranyl, benzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzofuranyl, dibenzothienyl, dibenzothiophene sulfone group, carbazolyl, dibenzosilyl, indenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl and triindolophenyl, but the embodiments of the present disclosure are not limited thereto.
[0582] The term "Period 4 transition metal" as used herein refers to an element of the 4th period and d-block of the periodic table, and non-limiting examples thereof include scandium (Sc), titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), and zinc (Zn).
[0583] The term "5th period transition metal" as used herein refers to an element of the 5th period and d-block of the periodic table, and non-limiting examples thereof include yttrium (Y), zirconium (Zr), niobium (Nb), molybdenum (Mo), technetium (Tc), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag) and cadmium (Cd).
[0584] The term "period 6 transition metal" as used herein refers to elements of period 6 and d-block and f-block of the periodic table, and non-limiting examples thereof include lanthanum (La), samarium (Sm), europium (Eu), terbium (Tb), thulium (Tm), ytterbium (Yb), lutetium (Lu), hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pr), gold (Au), and mercury (Hg).
[0585] As used herein, the term "C 1 -C 60 The term “alkyl” as used herein refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 (preferably 1 to 20, more preferably 1 to 10) carbon atoms, and non-limiting examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl. 1 -C 60 "Alkylene" refers to C 1 -C 60 An alkyl group is a divalent group having the same structure.
[0586] As used herein, the term "C 2 -C 60 "Alkenyl" refers to, for example, 2 -C 60 The term "C" as used herein refers to a hydrocarbon group having at least one carbon-carbon double bond in the middle and / or at the terminal of the alkyl group, and non-limiting examples thereof include vinyl, propenyl, and butenyl. 2 -C 60 "Alkenylene" refers to C 2 -C 60 Alkenyl groups have divalent groups of the same structure.
[0587] As used herein, the term "C 2 -C 60 "Alkynyl" refers to, for example, 2 -C 60 The term "C" as used herein refers to a hydrocarbon group having at least one carbon-carbon triple bond in the middle and / or at the terminal of the alkyl group, and non-limiting examples thereof include ethynyl and propynyl. 2 -C 60 "Alkynylidene" refers to a C 2 -C 60 Alkynyl groups are divalent groups with the same structure.
[0588] As used herein, the term "C 1 -C 60 "Alkoxy" refers to -OA 101 (A 101 C 1 -C 60 Alkyl, preferably C1 -C 20 Alkyl, more preferably C 1 -C 10 The term "alkyl" refers to a monovalent group represented by an alkyl group, and non-limiting examples thereof include a methoxy group, an ethoxy group, and an isopropoxy group.
[0589] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. 3 -C 10 "Cycloalkylene" refers to 3 -C 10 The cycloalkyl group has a divalent group of the same structure.
[0590] As used herein, the term "C 1 -C 10 The term "heterocycloalkyl" as used herein refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom and 1 to 10 carbon atoms as the remaining ring-forming atoms, and non-limiting examples thereof include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and tetrahydrothienyl. 1 -C 10 "Heterocycloalkylene" refers to a C 1 -C 10 The heterocycloalkyl group has a divalent group of the same structure.
[0591] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and not having aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl and cycloheptenyl. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to 3 -C 10 The cycloalkenyl group has a divalent group of the same structure.
[0592] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl group" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom, 1 to 10 carbon atoms as the remaining ring-forming atoms and at least one double bond in its ring. 1 -C 10Non-limiting examples of heterocycloalkenyl include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. As used herein, the term “C 1 -C 10 "Heterocycloalkenylene" refers to a C 1 -C 10 The heterocycloalkenyl group has a divalent group of the same structure.
[0593] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and The term "C 6 -C 60 "Arylene" refers to C 6 -C 60 Aryl has a divalent group with the same structure. 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each independently include two or more rings, the respective rings may be fused to each other.
[0594] As used herein, the term "C 1 -C 60 The term "heteroaryl group" refers to a monovalent group having a heterocyclic aromatic system (having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom in addition to 1 to 60 carbon atoms as the remaining ring-forming atoms). 1 -C 60 Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. As used herein, the term “C 1 -C 60 "Heteroarylene" refers to a C 1 -C 60 Heteroaryl has a divalent group with the same structure. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each independently include two or more rings, the respective rings may be fused (bonded) to each other.
[0595] As used herein, the term "C 6 -C 60 "Aryloxy" refers to a 102 (A 102 C 6 -C60 aryl) represented by a monovalent group, and as used herein, the term "C 6 -C 60 "Arylthio" refers to -SA 103 (A 103 C 6 -C 60 A monovalent group represented by an aryl group.
[0596] As used herein, the term "C 1 -C 60 "Heteroaryloxy" refers to a 104 (A 104 C 1 -C 60 Heteroaryl) and the term "C 1 -C 60 "Heteroarylthio" refers to -SA 105 (A 105 C 1 -C 60 heteroaryl).
[0597] As used herein, the term "monovalent non-aromatic fused polycyclic group" refers to a monovalent group having two or more rings fused to each other, having only carbon atoms as ring atoms (e.g., having 8 to 60 carbon atoms), and having no aromaticity in its entire molecular structure (e.g., the molecular structure as a whole does not have aromaticity). A non-limiting 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.
[0598] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group having two or more rings fused to each other, having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom in addition to carbon atoms (e.g., 1 to 60 carbon atoms), and its entire molecular structure has no aromaticity (e.g., the molecular structure as a whole does not have aromaticity). A non-limiting example of a monovalent non-aromatic fused heteropolycyclic group is a carbazolyl group. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as a monovalent non-aromatic fused heteropolycyclic group.
[0599] As used herein, the term "C 5 -C 60 "Carbocyclic group" refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms, wherein the ring atoms are carbon atoms only. 5 -C 30 Carbocyclic groups are preferred. As used herein, the term "C5 -C 60 "Carbocyclic group" refers to an aromatic carbocyclic group or a non-aromatic carbocyclic group. 5 -C 60 The carbocyclic group can be a ring (such as benzene), a monovalent group (such as phenyl) or a divalent group (such as phenylene). 5 -C 60 The number of substituents of the carbocyclic group, C 5 -C 60 The carbocyclic group may be a trivalent group or a tetravalent group.
[0600] As used herein, the term "C 1 -C 60 "Heterocyclic group" refers to a C 5 -C 60 A carbocyclic group has a group having the same structure except that, in addition to carbon atoms (the number of carbon atoms may be in the range of 1 to 60), at least one heteroatom selected from N, O, Si, P and S is used as a ring-forming atom, wherein C 1 -C 30 A heterocyclic group is preferred.
[0601] In this specification, substituted C 5 -C 60 Carbocyclic, substituted C 1 -C 60 Heterocyclic, substituted C 5 -C 30 Carbocyclic, substituted C 1 -C 30 Heterocyclic, substituted C 3 -C 10 Cycloalkylene, substituted C 1 -C 10 Heterocycloalkylene, substituted C 3 -C 10 Cycloalkenylene, substituted C 1 -C 10 Heterocycloalkenylene, substituted C 6 -C 60 Arylene, substituted C 1 -C 60 heteroarylene, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
[0602] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;
[0603] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 );
[0604] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
[0605] Each of the following C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 );as well as
[0606] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),and
[0607] Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidino; hydrazine; hydrazone; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; C 3 -C 10 Cycloalkyl; C 1 -C 10 Heterocycloalkyl; C 3 -C 10 Cycloalkenyl; C 1 -C 10 Heterocycloalkenyl; C 6 -C 60 Aryl; C 1 -C 60 Heteroaryl; C 1 -C 60 Heteroaryloxy; C 1 -C 60 heteroarylthio; monovalent non-aromatic fused polycyclic group; monovalent non-aromatic fused heteropolycyclic group; C substituted by at least one selected from deuterium, -F and cyano 1 -C 60 Alkyl; C substituted by at least one selected from deuterium, -F and cyano 6 -C 60 Aryl; biphenyl and terphenyl.
[0608] The term "Ph" as used herein refers to a phenyl group, the term "Me" as used herein refers to a methyl group, the term "Et" as used herein refers to an ethyl group, the term "iso-Pr" as used herein refers to an isopropyl group, the term "tert-Bu" or "Bu" as used herein refers to an ethyl group. t” refers to tert-butyl, the term “OMe” as used herein refers to methoxy, and “D” refers to deuterium.
[0609] As used herein, the term "biphenyl" refers to a "phenyl group substituted by a phenyl group". For example, a "biphenyl group" may be a group having C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.
[0610] As used herein, the term "terphenyl" refers to a "phenyl group substituted with a biphenyl group". For example, a "terphenyl group" may be a group having a C 6 -C 6 Aryl substituted C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.
[0611] Unless otherwise defined, * and *' as used herein each refer to a binding site to an adjacent atom in the corresponding formula.
[0612] Hereinafter, a compound according to an embodiment and an organic light-emitting device according to an embodiment will be described in more detail with reference to Examples. The expression "replacing A with B" used in describing a synthesis example means replacing A with the same molar equivalent of B.
[0613] Example
[0614] Example 1-1
[0615] As an anode, a substrate deposited with indium tin oxide (ITO) was cut into a size of 50 mm×50 mm×0.5 mm, and cleaned by ultrasonication with isopropyl alcohol and pure water for 10 minutes, then irradiated with ultraviolet light for 10 minutes and exposed to ozone. The obtained ITO substrate was mounted on a vacuum deposition device.
[0616] m-MTDATA was deposited on the ITO substrate to form a layer with a thickness of Then, NPB is vacuum deposited on the hole injection layer to form a hole injection layer with a thickness of The hole transport layer is co-deposited with compounds HT-01, ET01, PD1 and DA-02 at a weight ratio of 70:30:15:1 on the hole transport layer to form a layer with a thickness of Compound ET1 is deposited on the emission layer to form a layer with a thickness of Al is deposited on the electron transport layer to form a layer with a thickness of The cathode of the organic light-emitting device is thus completed.
[0617]
[0618] Examples 1-2 to 1-5 and Comparative Examples 1-1 to 1-25
[0619] An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the emission layers were each formed using the compounds shown in Table 1, respectively.
[0620] Evaluation Example 1
[0621] Using Keithley SMU236 and luminance meter PR650 at 10mA / cm 2 The efficiency, emission wavelength and lifetime of the organic light-emitting devices manufactured according to Examples 1-1 to 1-5 and Comparative Examples 1-1 to 1-25 were measured at a current density of . The results are shown in Table 1. The lifetime is a measurement of the time it takes for the luminance to decrease from the initial luminance to 90% of the initial luminance.
[0622]
Table 1
[0623]
[0624]
[0625]
[0626] DCJTB: (4-(Dicyanomethylene)-2-tert-butyl-6-(1,1,7,7,-tetramethyljulolidine-9-enyl)-H-pyran)
[0627] Table 1 shows that the organic light-emitting devices of Examples 1-1 to 1-5 have greater current efficiency and longer lifespan than the organic light-emitting devices of Comparative Examples 1-1 to 1-25.
[0628] Example 2-1
[0629] As an anode, a substrate deposited with indium tin oxide (ITO) was cut into a size of 50 mm×50 mm×0.5 mm, and cleaned by ultrasonication with isopropyl alcohol and pure water for 10 minutes, then irradiated with ultraviolet light for 10 minutes and exposed to ozone. The obtained ITO substrate was mounted on a vacuum deposition device.
[0630] m-MTDATA was deposited on the ITO substrate to form a layer with a thickness of Then, NPB is vacuum deposited on the hole injection layer to form a hole injection layer with a thickness of The hole transport layer is co-deposited with compounds HT-02, ET02, PD3 and DA-03 at a weight ratio of 70:30:15:1 on the hole transport layer to form a layer with a thickness of Compound ET01 is deposited on the emission layer to form a layer with a thickness of Compound ET1 is deposited on the hole blocking layer to form a layer with a thickness of Al is deposited on the electron transport layer to form a layer with a thickness of The cathode of the organic light-emitting device is thus completed.
[0631] Examples 2-2 to 2-5 and Comparative Examples 2-1 to 2-25
[0632] An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that the emission layer and the hole blocking layer were formed using the compounds shown in Table 2, respectively.
[0633] Evaluation Example 2
[0634] Using Keithley SMU236 and luminance meter PR650 at 10mA / cm 2 The efficiency, emission wavelength and lifetime of the organic light-emitting devices manufactured according to Examples 2-1 to 2-5 and Comparative Examples 2-1 to 2-25 were measured at a current density of . The results are shown in Table 2. The lifetime is a measurement of the time it takes for the luminance to decrease from the initial luminance to 90% of the initial luminance.
[0635]
Table 2
[0636]
[0637]
[0638]
[0639] Table 2 shows that the organic light-emitting devices of Examples 2-1 to 2-5 have greater current efficiency and longer lifespan than the organic light-emitting devices of Comparative Examples 2-1 to 2-25.
[0640] Example 3-1
[0641] As an anode, a substrate deposited with indium tin oxide (ITO) was cut into a size of 50 mm×50 mm×0.5 mm, and cleaned by ultrasonication with isopropyl alcohol and pure water for 10 minutes, then irradiated with ultraviolet light for 10 minutes and exposed to ozone. The obtained ITO substrate was mounted on a vacuum deposition device.
[0642] m-MTDATA was deposited on the ITO substrate to form a layer with a thickness of Then, NPB is vacuum deposited on the hole injection layer to form a hole injection layer with a thickness of The hole transport layer is co-deposited with compounds HT-01, ET02, 1 and DA-02 at a weight ratio of 70:30:15:1 on the hole transport layer to form a film with a thickness of Compound ET1 is deposited on the emission layer to form a layer with a thickness of Al is deposited on the electron transport layer to form a layer with a thickness of The cathode of the organic light-emitting device is thus completed.
[0643] Examples 3-2 to 3-5 and Comparative Examples 3-1 to 3-25
[0644] An organic light-emitting device was manufactured in the same manner as in Example 3-1, except that the emission layers were formed using the compounds shown in Table 3, respectively.
[0645] Evaluation Example 3
[0646] Using Keithley SMU236 and luminance meter PR650 at 10mA / cm 2 The efficiency, emission wavelength and lifetime of the organic light-emitting devices manufactured according to Examples 3-1 to 3-5 and Comparative Examples 3-1 to 3-25 were measured at a current density of . The results are shown in Table 3. The lifetime is a measurement of the time it takes for the luminance to decrease from the initial luminance to 90% of the initial luminance.
[0647] Table 3
[0648]
[0649]
[0650] Table 3 shows that the organic light-emitting devices of Examples 3-1 to 3-5 have greater current efficiency and longer lifespan than the organic light-emitting devices of Comparative Examples 3-1 to 3-25.
[0651] As described above, the organic light-emitting device according to the embodiment of the present disclosure may have high efficiency and a long lifespan.
[0652] The terminology used herein is for the purpose of describing particular example embodiments only and is not intended to be limiting of the invention.
[0653] As used herein, the terms "substantially", "about" and similar terms are used as approximate terms rather than as degree terms, and are intended to take into account the inherent deviations of measured values or calculated values that will be recognized by those of ordinary skill in the art. In addition, any numerical ranges listed herein are intended to include all subranges of the same numerical precision included in the listed range. For example, the range of "1.0 to 10.0" is intended to include all subranges between the listed minimum value 1.0 and the listed maximum value 10.0 (and including the end value), that is, a subrange with a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limit listed herein is intended to include all lower numerical limits included therein, and any minimum numerical limit listed in this specification is intended to include all higher numerical limits included therein. Therefore, the applicant reserves the right to amend this specification (including claims) to explicitly list any subranges included in the range explicitly listed herein. It is intended to inherently describe all such ranges in this specification so that the modification for explicitly listing any such subranges will meet the requirements of Article 33 of the Chinese Patent Law.
[0654] The use of “may” when describing embodiments of the present inventive concept means “one or more embodiments of the present inventive concept”.
[0655] It should be understood that the embodiments described herein should be considered to be merely descriptive and not for limiting purposes. The description of features or aspects in each embodiment should generally be considered to be applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the drawings, it will be understood by those of ordinary skill in the art that various changes may be made in form and detail therein without departing from the spirit and scope defined by the appended claims and their equivalents.
Claims
1. An organic light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; as well as an organic layer between the first electrode and the second electrode, wherein the organic layer comprises an emission layer, The emission layer includes a first compound, a second compound, a third compound and a fourth compound, The first compound is represented by Formula 1; The second compound is represented by Formula 2; The third compound is represented by Formula 3; The fourth compound is represented by any one of Formula 4-1 to Formula 4-3; and The first compound, the second compound, the third compound and the fourth compound are different from each other: <Formula 1> <Formula 2> <Formula 3> M 31 (L 31 ) n31 (L 32 ) n32 <Formula 4-1> (D 41 ) n41 -(L 41 ) a41 -(A 41 ) m41 <Formula 4-2> (D 41 ) n41 -(L 41 ) a41 -(A 41 ) m41 -(L 42 ) a42 -(D 42 ) n42 <Formula 4-3> (A 41 ) m41 -(L 41 ) a41 -(D 41 ) n41 -(L 42 ) a42 -(A 42 ) m42 Among them, in formula 1, X 11 Selected from O, S, N (R 19 ) and C(R 19 )(R 20 ); R 11 To R 20 Each independently selected from: By *-(L 11 ) a11 -A 11 The groups represented by hydrogen, deuterium, C1-C 60 Alkyl, ring groups without π-electron-depleted nitrogen, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), and -N(Q1)(Q2); A ring group containing no π-electron-depleted nitrogen substituted with at least one selected from the group consisting of deuterium, C1-C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 ) and -N(Q 31 )(Q 32 );as well as A π-electron-depleted nitrogen-free ring group substituted with at least one π-electron-depleted nitrogen-free ring group, wherein the at least one π-electron-depleted nitrogen-free ring group is substituted with at least one selected from the group consisting of deuterium, C1-C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 21 )(Q 22 )(Q 23 )、-Si(Q 21 )(Q 22 )(Q 23 )、-B(Q 21 )(Q 22 ) and -N(Q 21 )(Q 22 ), L 11 Selected from: Ring groups that do not contain π-electron-depleted nitrogen, -C(Q1)(Q2)-, -Si(Q1)(Q2)-, -B(Q1)-, and -N(Q1)-; and A ring group containing no π-electron-depleted nitrogen substituted with at least one selected from the group consisting of deuterium, C1-C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 ) and -N(Q 31 )(Q 32 ), a11 is selected from 1, 2 and 3, and A 11 Selected from: A ring group that does not contain a π-electron-depleted nitrogen; A ring group containing no π-electron-depleted nitrogen substituted with at least one selected from the group consisting of deuterium, C1-C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 ) and -N(Q 31 )(Q 32 );as well as A π-electron-depleted nitrogen-free ring group substituted with at least one π-electron-depleted nitrogen-free ring group, wherein the at least one π-electron-depleted nitrogen-free ring group is substituted with at least one selected from the group consisting of deuterium, C1-C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 21 )(Q 22 )(Q 23 )、-Si(Q 21 )(Q 22 )(Q 23 )、-B(Q 21 )(Q 22 ) and -N(Q 21 )(Q 22 ), In Formula 2, L 21 To L 23 are each independently selected from substituted or unsubstituted C5-C 30 Carbocyclic group and substituted or unsubstituted C1-C 30 Heterocyclic group, a21 to a23 are each independently selected from 0, 1 and 2, and R 21 To R 23 are each independently selected from 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 C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2), In Formula 3, M 31 is selected from the group consisting of period 4 transition metals, period 5 transition metals and period 6 transition metals, L 31 is a ligand represented by one of Formulae 3A to 3D, L 32 is selected from the group consisting of a monodentate ligand, a bidentate ligand and a tridentate ligand, n31 is 1 or 2, and n32 is selected from 0, 1, 2, 3 and 4, Wherein in Formula 3A to Formula 3D, A 31 To A 34 Each independently selected from C5-C 30 Carbocyclic and C1-C 30 Heterocyclic group, T 31 To T 34 Each is independently selected from a single bond, a double bond, *-O-*', *-S-*', *-C(=O)-*', *-S(=O)-*', *-C(R 35 )(R 36 )-*'、*-C(R 35 )=C(R 36 )-*'、*-C(R 35 )=*'、*-Si(R 35 )(R 36 )-*'、*-B(R 35 )-*'、*-N(R 35 )-*' and *-P(R 35 )-*', k31 to k34 are each independently selected from 1, 2 and 3, Y 31 To Y 34 Each independently selected from a single bond, *-O-*', *-S-*', *-C(R 37 )(R 38 )-*'、*-Si(R 37 )(R 38 )-*'、*-B(R 37 )-*'、*-N(R 37 )-*' and *-P(R 37 )-*', *1, *2, *3 and *4 indicate the difference between 31 The binding site R 31 To R 38 each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphate 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 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 C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2), wherein R 31 To R 38 are optionally linked to each other to form a substituted or unsubstituted C5-C 60 Carbocyclic or substituted or unsubstituted C1-C 60 a heterocyclic group, and b31 to b34 are each independently an integer selected from 0 to 10, In Formula 4-1 to Formula 4-3, A 41 and A 42 Each independently selected from: Ring groups that do not contain π-electron-depleted nitrogen, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), and -N(Q1)(Q2); A ring group containing no π-electron-depleted nitrogen substituted with at least one selected from the group consisting of deuterium, C1-C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 ) and -N(Q 31 )(Q 32 );as well as A π-electron-depleted nitrogen-free ring group substituted with at least one π-electron-depleted nitrogen-free ring group, wherein the at least one π-electron-depleted nitrogen-free ring group is substituted with at least one selected from the group consisting of deuterium, C1-C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 21 )(Q 22 )(Q 23 )、-Si(Q 21 )(Q 22 )(Q 23 )、-B(Q 21 )(Q 22 ) and -N(Q 21 )(Q 22 ), m41 and m42 are each independently selected from 1, 2 and 3, D 41 and D 42 Each independently selected from: -F, cyano, π-electron-depleted nitrogen-containing ring groups, C(═O)-containing groups, S(═O)-containing groups, S(═O)2-containing groups, P(═O)-containing groups, and P(═S)-containing groups; a π-electron-depleted nitrogen-containing ring group, a C(═O)-containing group, a S(═O)-containing group, a S(═O)2-containing group, a P(═O)-containing group, and a P(═S)-containing group, each of which is substituted with at least one selected from the group consisting of deuterium, -F, cyano, C1-C 60 Alkyl groups, ring groups containing π-electron-depleted nitrogen, and ring groups not containing π-electron-depleted nitrogen; a π-electron-depleted nitrogen-containing ring group, a C(═O)-containing group, a S(═O)-containing group, a S(═O)2-containing group, a P(═O)-containing group, and a P(═S)-containing group, each of which is independently selected from deuterium, -F, cyano, C1-C 60 The C1-C2 substituted alkyl group is a C1-C2 substituted alkyl group, ... 60 Alkyl groups, ring groups containing π-electron-depleted nitrogen, and ring groups not containing π-electron-depleted nitrogen; Each of the following C1-C 60 Alkyl groups and ring groups without π-electron-depleted nitrogen: -F, cyano groups and ring groups with π-electron-depleted nitrogen; Each of the C1-C 60 An alkyl group and a ring group containing no π-electron-depleted nitrogen, wherein at least one ring group containing π-electron-depleted nitrogen is substituted by at least one selected from the group consisting of deuterium, -F, cyano, C1-C 60 Alkyl groups, π-electron-depleted nitrogen-containing ring groups, and π-electron-free nitrogen-free ring groups; and Each of the following C1-C 60 Alkyl and ring groups without π-electron-depleted nitrogen: C1-C2-substituted with at least one selected from -F, cyano and ring groups containing π-electron-depleted nitrogen 60 Alkyl groups and ring groups not containing π-electron-depleted nitrogen, n41 and n42 are each independently selected from 1, 2 and 3, L 41 and L 42 Each independently selected from: Ring groups that do not contain π-electron-depleted nitrogen, -C(Q1)(Q2)-, -Si(Q1)(Q2)-, -B(Q1)-, and -N(Q1)-; and A ring group containing no π-electron-depleted nitrogen substituted with at least one selected from the group consisting of deuterium, C1-C 60 Alkyl, ring group without π-electron-depleted nitrogen, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 ) and -N(Q 31 )(Q 32 ),and a41 and a42 are each independently selected from 0, 1, 2 and 3, Wherein in Formula 1, Formula 2, Formula 3 and Formula 4-1 to Formula 4-3, The substituted C1-C 60 Alkyl, the substituted C2-C 60 Alkenyl, the substituted C2-C 60 Alkynyl, the substituted C1-C 60 Alkoxy, the substituted C3-C 10 Cycloalkyl, the substituted C1-C 10 Heterocycloalkyl, the substituted C3-C 10 Cycloalkenyl, the substituted C1-C 10 Heterocycloalkenyl, the substituted C6-C 60 Aryl, the substituted C6-C 60 Aryloxy, the substituted C6-C 60 Arylthio, the substituted C1-C 60 heteroaryl, the substituted monovalent non-aromatic fused polycyclic group, the substituted monovalent non-aromatic fused heteropolycyclic group, the substituted C5-C 30 Carbocyclic group, the substituted C1-C 30 Heterocyclic group, the substituted C5-C 60 The carbocyclic group and the substituted C1-C 60 At least one substituent in the heterocyclic group is selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy; Each of the following C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, 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, C1-C 60 Heteroaryloxy, C1-C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 ) and -P(=O)(Q 11 )(Q 12 ); 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, C1-C 60 Heteroaryloxy, C1-C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group; Each of the following 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, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, 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, C1-C 60 Heteroaryloxy, C1-C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 ) and -P(=O)(Q 21 )(Q 22 ); as well as -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ), Among them, Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, 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, C1-C 60 Heteroaryloxy, C1-C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group. 2 . The organic light-emitting device of claim 1 , wherein the first compound, the second compound, and the third compound do not emit light. The organic light-emitting device as claimed in claim 1 , wherein the fourth compound emits light. 4 . The organic light emitting device of claim 1 , wherein a ratio of light emitted from the fourth compound to total light emitted from the emission layer is 80% or more.
5. The organic light-emitting device according to claim 1, wherein R 11 To R 19 At least one of them is *-(L 11 ) a11 -A 11 express.
6. The organic light-emitting device according to claim 1, wherein X 11 O, S or N (R 19 ).
7. The organic light-emitting device according to claim 1, wherein A 11 Selected from: Phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, 1-Benzene, 2 ... phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, benzo[theta]-1, benzo[theta]-2, benzo[theta]-3, benzo[theta]-4, benzo[theta]-5, benzo[theta]-6, benzo[theta]-7, benzo[theta]-8, benzo[theta]-9, benzo[theta]-10, benzo[theta]-11, benzo[theta]-12, benzo[theta]-13, benzo[theta]-14, benzo[theta]-15, benzo[theta]-16, benzo[theta]-17, benzo[theta]-18, benzo[theta]-19, benzo[theta]-21, benzo[theta]-22, benzo[theta]-23, benzo[theta]-24, benzo[theta]-25 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 ) and -N(Q 31 )(Q 32 );as well as phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, 1-C 1-D 1-H 2 ... 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, -C(Q 21 )(Q 22 )(Q 23 )、-Si(Q 21 )(Q 22 )(Q 23 )、-B(Q 21 )(Q 22 ) and -N(Q 21 )(Q 22 ) is at least one substituted phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl and dinaphthothiophenyl.
8. The organic light-emitting device as claimed in claim 1, wherein A 11 It is expressed by one of the equations 8-1 to 8-5: in, In formula 8-1 to formula 8-5, X 81 Selected from O, S, N (R 89 ) and C(R 89 )(R 90 ), R 81 To R 90 are each independently selected from hydrogen, deuterium, C1-C 20 alkyl, phenyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl, and *Indicates the binding site with the neighboring atoms.
9. The organic light-emitting device of claim 1, wherein the first compound is represented by one of Formula 1-1 to Formula 1-9: in, In Formula 1-1 to Formula 1-9, L 11 、a11、A 11 and R 11 To R 19 Each is the same as defined in Formula 1.
10. The organic light-emitting device as claimed in claim 1, wherein L in Formula 2 21 To L 23 Each is independently selected from phenyl, naphthyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, phenanthrenyl, pyrenyl, yl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; and Fluoranthene, triphenylene, phenanthrenyl, pyrenyl, each substituted by at least one selected from the following yl, peryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl: deuterium, -F, cyano, C1-C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, indenofluorenyl, indolefluorenyl, benzofuranofluorenyl, benzothiophenefluorenyl, indenocarbazolyl, indolecarbazolyl, benzofuranocarbazolyl, benzothiophenecarbazolyl, indenodibenzofuranyl, indoledibenzofuranyl, benzofuranodibenzofuranyl, benzo thienodibenzofuranyl, indenodibenzothienyl, indoledibenzothienyl, benzofuranodibenzothienyl, benzothienodibenzothienyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, naphthyridinyl, quinoxalinyl, quinazolinyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl and diazadibenzothienyl.
11. The organic light-emitting device according to claim 1, wherein R in Formula 2 21 To R 23 Each independently selected from: phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, phenanthrenyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, benzoquinoxalinyl, benzoquinazolinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothienyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl, and diazadibenzothienyl; phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, phenanthrenyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, benzoquinoxalinyl, benzoquinazolinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl and diazadibenzothiophenyl substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 10 Alkyl, C1-C 10 alkoxy, phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, phenanthrenyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, benzoquinoxalinyl, benzoquinazolinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothienyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl, diazadibenzothienyl, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 )、-N(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)(Q 31 )、-S(=O)2(Q 31 )、-P(=O)(Q 31 )(Q 32 ) and -P(=S)(Q 31 )(Q 32 );as well as -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), - C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), and -P(=S)(Q1)(Q2), and Among them, Q1 to Q3 and Q 31 To Q 33 Each is independently selected from phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, phenanthrenyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, benzoquinoxalinyl, benzoquinazolinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl and diazadibenzothiophenyl.
12. The organic light-emitting device according to claim 1, wherein the 21 To R 23 At least one of the groups is selected from the group represented by Formula 2A, the group represented by Formula 2B, -C(Q1)(Q2)(Q3) and -Si(Q1)(Q2)(Q3): in, In Formula 2A and Formula 2B, Y 21 is selected from phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, phenanthrenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothienyl, -C(Q 31 )(Q 32 )(Q 33 ) and -Si(Q 31 )(Q 32 )(Q 33 ), R 24 To R 27 are each independently selected from hydrogen, deuterium, C1-C 10 Alkyl, phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, phenanthrenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, -C(Q 31 )(Q 32 )(Q 33 ) and -Si(Q 31 )(Q 32 )(Q 33 ), Q1 to Q3 and Q 31 To Q 33 are each independently selected from phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, phenanthrenyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl, and *Indicates the binding site with the neighboring atoms.
13. The organic light-emitting device according to claim 1, wherein the third compound is represented by Formula 3-1 or Formula 3-2: in, In formula 3-1 and formula 3-2, X 31 To X 40 are each independently selected from N and C, and M 31 , A 31 To A 34 , R 31 To R 34 , b31 to b34, Y 31 To Y 34 、T 31 To T 33 、k31 to k33、L 32 , n31 and n32 are each the same as those defined in Formula 3.
14. The organic light-emitting device as claimed in claim 1, wherein A 41 and A 42 Each independently selected from a group represented by formula 12, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2) and -N(Q1)(Q2): <Formula 12> in, In formula 12, X 121 Selected from O, S, N (R 123 ) and C(R 123 )(R 124 ), X 122 Selected from single bond, O, S, N(R 125 ) and C(R 125 )(R 126 ), A 121 and A 122 Each is independently selected from phenyl, naphthyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, phenanthrenyl, pyrenyl, yl, peryl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl, R 121 To R 126 Each independently selected from: Binding site, hydrogen, deuterium, C1-C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, -Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 ) and -N(Q 31 )(Q 32 );as well as phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, benzo[theta]-1, benzo[theta]-2, benzo[theta]-3, benzo[theta]-4, benzo[theta]-5, benzo[theta]-6, benzo[theta]-7, benzo[theta]-8, benzo[theta]-9, benzo[theta]-10, benzo[theta]-11, benzo[theta]-12, benzo[theta]-13, benzo[theta]-14, benzo[theta]-15, benzo[theta]-16, benzo[theta]-17, benzo[theta]-18, benzo[theta]-19, benzo[theta]-21, benzo[theta]-22, benzo[theta]-23, benzo[theta]-24, benzo[theta]-25 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, -Si(Q 21 )(Q 22 )(Q 23 )、-B(Q 21 )(Q 22 ) and -N(Q 21 )(Q 22 ), where R 123 and R 124 are optionally linked to each other to form a ring group that does not contain a π-electron-depleted nitrogen, R 125 and R 126 are optionally linked to each other to form a ring group that does not contain π-electron-depleted nitrogen, and are selected from R 121 To R 126 is the binding site, and b121 and b122 are each independently selected from 1, 2, 3, 4, 5 and 6.
15. The organic light emitting device as claimed in claim 1, wherein D 41 and D 42 Each independently selected from: -F, cyano, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl, quinazolinyl, and a group represented by one of Formula 13-1 to Formula 13-3; pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl and quinazolinyl, each substituted with at least one selected from the group consisting of deuterium, -F, cyano, C1-C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl and quinazolinyl; pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl and quinazolinyl, each independently selected from deuterium, -F, cyano, C1-C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, substituted with at least one of 1-2-dihydro-2-pyridyl, 1-6 ... 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl and quinazolinyl; Each of the following C1-C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, 1-F, cyano, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl and quinazolinyl; Each of the following C1-C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, 1-C 1-D ... 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridyl, pyrazinyl , pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl and quinazolinyl substituted with at least one of pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl and quinazolinyl; and Each of the following C1-C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, 1-C 2-hydroxy-1-pyridyl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 1-hydroxy-1-oxo-1-yl, 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, 1-Benzene, 2 ... in, In Formula 13-1 to Formula 13-3, X 131 Selected from C(=O), S(=O), S(=O)2, P(=O)(R 134 ) and P(=S)(R 134 ), X 132 Selected from O, S, C(=O), S(=O), S(=O)2, P(=O)(R 135 ) and P(=S)(R 135 ), k132 is 0 or 1. When k132 is 0, -(X 132 ) k132 - for direct connection, Y 131 Selected from O and S, A 131 and A 132 Each is independently selected from phenyl, naphthyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, phenanthrenyl, pyrenyl, yl, peryl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl, R 131 To R 135 Each independently selected from: Binding site, hydrogen, deuterium, -F, cyano, C1-C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl, and quinazolinyl; and Each of the following C1-C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl and quinazolinyl: deuterium, -F, cyano, C1-C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, 1-(4-nitrophenyl)-2-oxo-1-oxo-2-oxo-1-oxo-2-oxo-2-oxo-3-oxo-4-nitro ... 131 To R 135 is the binding site, and b131 and b132 are each independently selected from 1, 2, 3, 4, 5 and 6.
16. The organic light emitting device as claimed in claim 1, wherein L 41 and L 42 Each independently selected from: Phenyl, naphthyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, phenanthrenyl, pyrenyl, yl, peryl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, -C(Q1)(Q2)- and -Si(Q1)(Q2)-; and phenyl, naphthyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, phenanthrenyl, pyrenyl, yl, peryl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl: deuterium, C1-C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, yl, fluoranthene, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, -C(Q 31 )(Q 32 )(Q 33 ) and -Si(Q 31 )(Q 32 )(Q 33 ).
17. The organic light emitting device according to claim 1, wherein: The first compound is selected from the compounds of Group I; The second compound is selected from the compounds of Group II; The third compound is selected from the group consisting of compounds of Group III-I and Group III-II, and The fourth compound is selected from the group IV compounds: <Group I> <Group II> <Group III-I> <Group III-II> <Group IV> 18. The organic light emitting device according to claim 1, wherein: The first electrode is an anode, The second electrode is a cathode, The organic layer further includes a hole transport region between the first electrode and the emission layer and / or an electron transport region between the emission layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, an emission auxiliary layer and / or an electron blocking layer, and The electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer and / or an electron injection layer.
19. The organic light-emitting device of claim 18, wherein the hole blocking layer comprises a hole blocking material represented by Formula 2: <Formula 2> in, In formula 2, L 21 To L 23 are each independently selected from substituted or unsubstituted C5-C 30 Carbocyclic group and substituted or unsubstituted C1-C 30 Heterocyclic group, a21 to a23 are each independently selected from 0, 1 and 2, R 21 To R 23 are each independently selected from 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 C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), and -P(=S)(Q1)(Q2), and The substituted C3-C 10 Cycloalkyl, the substituted C1-C 10 Heterocycloalkyl, the substituted C3-C 10 Cycloalkenyl, the substituted C1-C 10 Heterocycloalkenyl, the substituted C6-C 60 Aryl, the substituted C6-C 60 Aryloxy, the substituted C6-C 60 Arylthio, the substituted C1-C 60 Heteroaryl, the substituted C5-C 30 Carbocyclic group, the substituted C1-C 30 At least one substituent of the heterocyclic group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy; Each of the following C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, 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, C1-C 60 Heteroaryloxy, C1-C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 ) and -P(=O)(Q 11 )(Q 12 ); 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, C1-C 60 Heteroaryloxy, C1-C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group; Each of the following 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, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, 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, C1-C 60 Heteroaryloxy, C1-C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 ) and -P(=O)(Q 21 )(Q 22 ); as well as -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 )和-P(=O)(Q 31 )(Q 32 ), Among them, Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each is independently selected from hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidino; hydrazine; hydrazone; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 Alkoxy; C3-C 10 Cycloalkyl; C1-C 10 Heterocycloalkyl; C3-C 10 Cycloalkenyl; C1-C 10 Heterocycloalkenyl; C6-C 60 Aryl; C1-C 60 Heteroaryl; C1-C 60 Heteroaryloxy; C1-C 60 Heteroarylthio; monovalent non-aromatic fused polycyclic group; monovalent non-aromatic fused heteropolycyclic group; C1-C1 substituted by at least one selected from deuterium, -F and cyano 60 Alkyl; C6-C substituted by at least one selected from deuterium, -F and cyano 60 Aryl; biphenyl and terphenyl.
20. A device, comprising: A thin film transistor, comprising a source electrode, a drain electrode, an active layer and a sealing portion; as well as The organic light-emitting device according to any one of claims 1 to 19, The first electrode of the organic light-emitting device is electrically connected to the source electrode or the drain electrode of the thin film transistor.
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