Organic light emitting device and apparatus including the same
By using a combination of compounds with specific structures as the emission layer material in an organic light-emitting device, the performance of the emission layer is optimized, solving the problems of insufficient light efficiency and lifetime in the prior art, and achieving a more efficient and longer-lasting light emission effect.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2020-09-16
- Publication Date
- 2026-03-17
AI Technical Summary
Existing organic light-emitting devices have shortcomings in terms of light efficiency and lifetime, especially in the selection of emission layer materials, which have not been fully optimized, resulting in poor performance.
Combinations of compounds with specific structures are used as emitter layer materials, including a first compound represented by Formula 1, a second compound represented by Formula 2A or Formula 2B, a third compound represented by Formula 3, and a fourth compound represented by Formula 4, and the performance of the emitter layer is optimized by combinations of these compounds.
This improves the light efficiency and lifespan of organic light-emitting devices, enhances their luminescent performance, and meets the requirements for high brightness and long lifespan.
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Figure CN112614949B_ABST
Abstract
Description
[0001] Cross-references to related applications
[0002] This application claims priority and benefit to Korean Patent Application No. 10-2019-0123352, filed with the Korean Intellectual Property Office on October 4, 2019, 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 said organic light-emitting device. Background Technology
[0004] Organic light-emitting devices are self-emitting devices that produce full-color images and also have wide viewing angles, high contrast, short response times, and suitable (e.g., excellent) characteristics in terms of brightness, driving voltage, and / or response speed.
[0005] Examples of organic light-emitting devices may include a first electrode located on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially located on the first electrode. Holes supplied by the first electrode can move toward the emission layer through the hole transport region, and electrons supplied by the second electrode can move toward the emission layer through the electron transport region. Charge carriers such as holes and electrons 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] An aspect of one or more embodiments includes an organic light-emitting device and an apparatus including said organic light-emitting device.
[0007] Other aspects will be set forth in part in the following description and will be partly apparent from the description or may be learned by practicing the embodiments presented in this disclosure.
[0008] According to the implementation plan, the organic light-emitting device includes:
[0009] First electrode;
[0010] The second electrode; and
[0011] In the organic layer between the first electrode and the second electrode,
[0012] The organic layer includes an emission layer.
[0013] The emission layer comprises 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 2A or formula 2B.
[0016] The third compound is represented by formula 3.
[0017] The fourth compound is represented by formula 4, 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]
[0022]
[0023] Formula 4
[0024]
[0025] In Equation 1,
[0026] X 11 It can be selected from O, S, N(R) 19 ) and C(R 19 (R) 20 ),
[0027] R 11 To R 20 Each can be selected independently from: by *-(L 11 ) a11 -A 11 The indicated groups are hydrogen, deuterium, and C1-C. 60 Alkyl groups, cyclic groups without nitrogen that has been depleted of π electrons, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2) and -N(Q1)(Q2);
[0028] Selected from deuterium, C1-C 60 Alkyl groups, cyclic groups without nitrogen that has been depleted of π electrons, -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 At least one substituted cyclic group of nitrogen that does not contain π-electron-depleted nitrogen; and
[0029] Selected from deuterium, C1-C 60 Alkyl groups, cyclic groups without nitrogen that has been depleted of π electrons, -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 At least one cyclic group of nitrogen that is substituted without π-electron depletion in the cyclic group of nitrogen.
[0030] L 11 You can choose from:
[0031] Cyclic groups of nitrogen without π-electron depletion, -C(Q1)(Q2)-, -Si(Q1)(Q2)-, -B(Q1)-, and -N(Q1)-; and
[0032] Selected from deuterium, C1-C 60 Alkyl groups, cyclic groups without nitrogen that has been depleted of π electrons, -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 At least one substituted cyclic group of nitrogen that does not have π electrons depleted in the group,
[0033] a11 can be selected from 1, 2, and 3, and
[0034] A 11 It can be selected from: cyclic groups of nitrogen that do not contain depleted π electrons;
[0035] Selected from deuterium, C1-C 60 Alkyl groups, cyclic groups without nitrogen that has been depleted of π electrons, -C(Q 31 (Q) 32 (Q) 33 ), -Si(Q 31 (Q) 32 (Q) 33 -B(Q) 31 (Q) 32 ) and -N(Q 31 (Q) 32At least one substituted cyclic group of nitrogen that does not contain π-electron-depleted nitrogen; and
[0036] Selected from deuterium, C1-C 60 Alkyl groups, cyclic groups without nitrogen that has been depleted of π electrons, -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 At least one cyclic group of nitrogen that is not π-electron depleted in the cyclic group of the nitrogen is substituted.
[0037] In equations 2A and 2B,
[0038] X 21 It can be selected from O, S, N(R) 24 ) and C(R 24 (R) 25 ),
[0039] k21 and k22 can each be independently selected from 0, 1, 2, 3, and 4, and the sum of k21 and k22 can be 1 or greater than 1.
[0040] k23 can be selected from 1, 2, 3, 4, 5, and 6.
[0041] R 21 To R 25 Each can be selected independently from: by *-(L 21 ) a21 -A 21 The groups represented are hydrogen, deuterium, -F, cyano groups, and C1-C. 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2);
[0042] Each is selected from deuterium, -F, cyano group, C1-C 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q) 31 (Q) 32 (Q) 33 ), -Si(Q31 (Q) 32 (Q) 33 -B(Q) 31 (Q) 32 -N(Q) 31 (Q) 32 -S(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) and -P(=S)(Q 31 (Q) 32 At least one substituted cyclic group containing π-electron-depleted nitrogen and a cyclic group not containing π-electron-depleted nitrogen; and
[0043] Each is selected independently from deuterium, -F, cyano groups, C1-C 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q) 21 (Q) 22 (Q) 23 ), -Si(Q 21 (Q) 22 (Q) 23 -B(Q) 21 (Q) 22 -N(Q) 21 (Q) 22 -S(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) and -P(=S)(Q 21 (Q) 22 At least one substituted cyclic group containing π-electron-depleted nitrogen and at least one substituted cyclic group not containing π-electron-depleted nitrogen in the cyclic group of )
[0044] L 21 It can be selected from: cyclic groups containing nitrogen with depleted π electrons, cyclic groups without depleted π electrons, -C(Q1)(Q2)-, -Si(Q1)(Q2)-, -B(Q1)-, -N(Q1)-, -S(=O)-, -S(=O)2-, -P(=O)(Q1)- and -P(=S)(Q1)-; and
[0045] Each is selected from deuterium, -F, cyano group, C1-C 60Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q) 31 (Q) 32 (Q) 33 ), -Si(Q 31 (Q) 32 (Q) 33 -B(Q) 31 (Q) 32 -N(Q) 31 (Q) 32 -S(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) and -P(=S)(Q 31 (Q) 32 At least one substituted cyclic group containing π-electron-depleted nitrogen and a cyclic group not containing π-electron-depleted nitrogen in the group.
[0046] a21 can be selected from 1, 2, and 3, and
[0047] A 21 You can choose from:
[0048] Cyclic groups containing nitrogen with depleted π electrons and cyclic groups not containing nitrogen with depleted π electrons;
[0049] Each is selected from deuterium, -F, cyano group, C1-C 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q) 31 (Q) 32 (Q) 33 ), -Si(Q 31 (Q) 32 (Q) 33 -B(Q) 31 (Q) 32 -N(Q) 31 (Q) 32 -S(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) and -P(=S)(Q 31 (Q) 32 At least one substituted cyclic group containing π-electron-depleted nitrogen and a cyclic group not containing π-electron-depleted nitrogen; and
[0050] Each is selected independently from deuterium, -F, cyano groups, C1-C60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q) 21 (Q) 22 (Q) 23 ), -Si(Q 21 (Q) 22 (Q) 23 -B(Q) 21 (Q) 22 -N(Q) 21 (Q) 22 -S(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) and -P(=S)(Q 21 (Q) 22 At least one of the following: a cyclic group containing π-electron-depleted nitrogen and a cyclic group not containing π-electron-depleted nitrogen.
[0051] In Equation 3,
[0052] M 31 It can be selected from transition metals of the 4th, 5th, and 6th periods.
[0053] L 31 It can be a ligand represented by one of Equations 3A to 3D.
[0054] L 32 It can be selected from monodentate ligands, bidentate ligands, and tripentate ligands.
[0055] n31 can be selected from 1 and 2.
[0056] n32 can be selected from 0, 1, 2, 3, and 4.
[0057] A 31 To A 34 Each can be independently selected from C5-C. 30 Carbocyclic groups and C1-C 30 Heterocyclic groups,
[0058] T 31 To T 34 Each can be independently selected from single bonds, double bonds, *-O-*', *-S-*', *-C(=O)-*', *-S(=O)-*', *-C(R) 35 (R) 36 )-*'、*-C(R 35 )=C(R36 )-*'、*-C(R 35 )=*'、*-Si(R 35 (R) 36 )-*'、*-B(R 35 )-*'、*-N(R 35 )-*' and *-P(R 35 )-*',
[0059] k31 to k34 can each be independently selected from 1, 2, and 3.
[0060] Y 31 To Y 34 Each can be independently selected from single bonds, *-O-*', *-S-*', *-C(R) 37 (R) 38 )-*'、*-Si(R 37 (R) 38 )-*'、*-B(R 37 )-*'、*-N(R 37 )-*' and *-P(R 37 )-*',
[0061] *1, *2, *3, and *4 can each represent M. 31 binding sites,
[0062] R 31 To R 38 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C groups. 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -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 R 31 To R 38 They can be optionally linked together to form substituted or unsubstituted C5-C 60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups, and
[0063] b31 to b34 can each be an integer from 0 to 10 independently.
[0064] In Equation 4,
[0065] X 41 It can be N, B, P (=)(R) 44 ) or P(=S)(R 44 ),
[0066] Y 41 To Y 43 Each can be independently O, S, N(R) 45 ), B(R) 45 ), C(R 45 (R) 46 ) or Si(R 45 (R) 46 ),
[0067] k41 is either 0 or 1, and when k41 is 0, -(Y 41 ) k41 -It can be absent.
[0068] A 41 To A 43 Each can be independently selected from C5-C. 30 Carbocyclic groups and C1-C 30 Heterocyclic groups,
[0069] R 41 To R 46 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C groups. 60 Alkyl groups, substituted or unsubstituted C2-C60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -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 R 41 To R 46 They can be optionally linked together to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups, and
[0070] b41 to b43 can each be an integer from 0 to 10 independently.
[0071] Among them, Q1 to Q3, Q 21 To Q 23 and Q 31 To Q 33 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C60 aryloxy group, C6-C 60 aryl thiols, C1-C 60 heteroaryl groups, C1-C 60 heteroaryloxy groups, C1-C 60 Heteroaryl thio groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, biphenyl groups, and terphenyl groups.
[0072] According to another embodiment, the device includes: a thin-film transistor including a source electrode, a drain electrode, and an active layer; and the 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. Attached Figure Description
[0073] The above and other aspects, features, and improvements of this disclosure will become more apparent from the following description taken in conjunction with the accompanying drawings, in which:
[0074] Figure 1 This is a schematic view of the organic light-emitting device according to the implementation plan;
[0075] Figure 2 This is a schematic view of an organic light-emitting device according to another embodiment;
[0076] Figure 3 This is a schematic view of an organic light-emitting device according to another embodiment; and
[0077] Figure 4 This is a schematic view of an organic light-emitting device according to another embodiment. Detailed Implementation
[0078] Reference will now be made in more detail to the embodiments, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout. In this respect, the embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, the embodiments are described below with reference to the accompanying drawings only to explain aspects of the present description. As used herein, the term “and / or” includes any and all combinations of one or more of the relevant listed items. Throughout the disclosure, the expression “at least one of a, b, and c” means 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.
[0079] In the following, embodiments of the present disclosure will be described in more detail with reference to the accompanying drawings. The same or corresponding components will be denoteed by the same reference numerals, and therefore redundant descriptions will be omitted (i.e., not provided).
[0080] As used herein, the singular forms “a”, “an”, and “the” are intended to also include the plural forms unless the context clearly indicates otherwise.
[0081] It should be further understood that the terms “comprises” and / or “comprising” used herein specify the presence of the specified features or components, but do not exclude the presence or addition of one or more other features or components.
[0082] It should be understood that when a layer, area, or component is referred to as being "on" or "above" another layer, area, or component, it can be formed directly or indirectly on the other layer, area, or component. That is, for example, there can be intermediate layers, areas, or components.
[0083] For ease of explanation, the dimensions of the elements in the accompanying drawings may be enlarged. In other words, because the dimensions and thicknesses of the components in the drawings are arbitrarily illustrated for ease of explanation, the following embodiments of this disclosure are not limited thereto.
[0084] As used herein, the term "organic layer" refers to one or more layers located between the first and second electrodes of an organic light-emitting device. The materials contained in the "organic layer" are not limited to organic materials.
[0085] An organic light-emitting device according to an embodiment of this disclosure includes: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, wherein the organic layer includes an emission layer comprising a first compound, a second compound, a third compound, and a fourth compound. The first compound may be represented by Formula 1, the second compound may be represented by Formula 2A or Formula 2B, the third compound may be represented by Formula 3, and the fourth compound may be represented by Formula 4. Furthermore, the first compound, the second compound, the third compound, and the fourth compound may be different from each other.
[0086] Formula 1
[0087]
[0088]
[0089] Formula 4
[0090]
[0091] In equations 1 to 4,
[0092] X 11 It can be selected from O, S, N(R) 19 ) and C(R 19 (R) 20 ),
[0093] R 11 To R 20 Each can be selected independently from:
[0094] From *-(L 11 ) a11 -A 11 The indicated groups are hydrogen, deuterium, and C1-C. 60 Alkyl groups, cyclic groups without nitrogen that has been depleted of π electrons, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2) and -N(Q1)(Q2);
[0095] Selected from deuterium, C1-C 60 Alkyl groups, cyclic groups without nitrogen that has been depleted of π electrons, -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 At least one substituted cyclic group of nitrogen that does not contain π-electron-depleted nitrogen; and
[0096] Selected from deuterium, C1-C 60 Alkyl groups, cyclic groups without nitrogen that has been depleted of π electrons, -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 At least one cyclic group of nitrogen that is substituted without π-electron depletion in the cyclic group of nitrogen.
[0097] L 11 You can choose from:
[0098] Cyclic groups of nitrogen without π-electron depletion, -C(Q1)(Q2)-, -Si(Q1)(Q2)-, -B(Q1)-, and -N(Q1)-; and
[0099] Selected from deuterium, C1-C 60 Alkyl groups, cyclic groups without nitrogen that has been depleted of π electrons, -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 At least one substituted cyclic group of nitrogen that does not have π electrons depleted in the group,
[0100] a11 can be selected from 1, 2, and 3.
[0101] A 11 You can choose from:
[0102] Cyclic groups that do not contain nitrogen with depleted π electrons;
[0103] Selected from deuterium, C1-C 60 Alkyl groups, cyclic groups without nitrogen that has been depleted of π electrons, -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 At least one substituted cyclic group of nitrogen that does not contain π-electron-depleted nitrogen; and
[0104] Selected from deuterium, C1-C 60 Alkyl groups, cyclic groups without nitrogen that has been depleted of π electrons, -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 At least one cyclic group of nitrogen that is substituted without π-electron depletion in the cyclic group of nitrogen.
[0105] X 21 It can be selected from O, S, N(R) 24 ) and C(R 24 (R) 25 ),
[0106] k21 and k22 can be independently selected from 0, 1, 2, 3, and 4, where the sum of k21 and k22 can be 1 or greater than 1.
[0107] k23 can be selected from 1, 2, 3, 4, 5, and 6.
[0108] R 21 To R 25 Each can be selected independently from:
[0109] From *-(L 21 ) a21 -A 21 The groups represented are hydrogen, deuterium, -F, cyano groups, and C1-C. 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2);
[0110] Each is selected from deuterium, -F, cyano group, C1-C 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q) 31 (Q) 32 (Q) 33 ), -Si(Q 31 (Q) 32 (Q) 33 -B(Q) 31 (Q) 32 -N(Q) 31 (Q) 32 -S(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) and -P(=S)(Q 31 (Q) 32 At least one substituted cyclic group containing π-electron-depleted nitrogen and a cyclic group not containing π-electron-depleted nitrogen; and
[0111] Each is selected independently from deuterium, -F, cyano groups, C1-C 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q) 21 (Q) 22 (Q) 23 ), -Si(Q 21(Q) 22 (Q) 23 -B(Q) 21 (Q) 22 -N(Q) 21 (Q) 22 -S(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) and -P(=S)(Q 21 (Q) 22 At least one substituted cyclic group containing π-electron-depleted nitrogen and at least one substituted cyclic group not containing π-electron-depleted nitrogen in the cyclic group of )
[0112] L 21 You can choose from:
[0113] Cyclic groups containing nitrogen with depleted π electrons, cyclic groups not containing nitrogen with depleted π electrons, -C(Q1)(Q2)-, -Si(Q1)(Q2)-, -B(Q1)-, -N(Q1)-, -S(=O)-, -S(=O)2-, -P(=O)(Q1)- and -P(=S)(Q1)-; and
[0114] Each is selected from deuterium, -F, cyano group, C1-C 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q) 31 (Q) 32 (Q) 33 ), -Si(Q 31 (Q) 32 (Q) 33 -B(Q) 31 (Q) 32 -N(Q) 31 (Q) 32 -S(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) and -P(=S)(Q 31 (Q) 32 At least one substituted cyclic group containing π-electron-depleted nitrogen and a cyclic group not containing π-electron-depleted nitrogen in the group.
[0115] a21 can be selected from 1, 2, and 3.
[0116] A 21 You can choose from:
[0117] Cyclic groups containing nitrogen with depleted π electrons and cyclic groups not containing nitrogen with depleted π electrons;
[0118] Each is selected from deuterium, -F, cyano group, C1-C 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q) 31 (Q) 32 (Q) 33 ), -Si(Q 31 (Q) 32 (Q) 33 -B(Q) 31 (Q) 32 -N(Q) 31 (Q) 32 -S(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) and -P(=S)(Q 31 (Q) 32 At least one substituted cyclic group containing π-electron-depleted nitrogen and a cyclic group not containing π-electron-depleted nitrogen; and
[0119] Each is selected independently from deuterium, -F, cyano groups, C1-C 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q) 21 (Q) 22 (Q) 23 ), -Si(Q 21 (Q) 22 (Q) 23 -B(Q) 21 (Q) 22 -N(Q) 21 (Q) 22 -S(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) and -P(=S)(Q 21 (Q) 22 At least one substituted cyclic group containing π-electron-depleted nitrogen and at least one substituted cyclic group not containing π-electron-depleted nitrogen in the cyclic group of )
[0120] M 31Transition metals can be selected from the 4th, 5th, and 6th periods of the periodic table.
[0121] L 31 It can be a ligand selected from one of Formula 3A to Formula 3D.
[0122] L 32 It can be selected from monodentate ligands, bidentate ligands, and tripentate ligands.
[0123] n31 can be 1 or 2.
[0124] n32 can be selected from 0, 1, 2, 3, and 4.
[0125] A 31 To A 34 Each can be independently selected from C5-C. 30 Carbocyclic groups and C1-C 30 Heterocyclic groups,
[0126] T 31 To T 34 Each can be independently selected from single bonds, double bonds, *-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 )-*',
[0127] k31 to k34 can each be independently selected from 1, 2, and 3.
[0128] Y 31 To Y 34 Each can be independently selected from single bonds, *-O-*', *-S-*', *-C(R) 37 (R) 38 )-*'、*-Si(R 37 (R) 38 )-*'、*-B(R 37 )-*'、*-N(R 37 )-*' and *-P(R 37 )-*',
[0129] *1, *2, *3, and *4 can each represent M. 31 binding sites,
[0130] R 31 To R 38 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C groups. 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -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 (For example, adjacent R) 31 To R 38 They can optionally be connected to each other to form substituted or unsubstituted C5-C 60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups,
[0131] b31 to b34 can each be an integer from 0 to 10 independently.
[0132] X 41 It can be N, B, P (=)(R) 44 ) or P(=S)(R 44 ),
[0133] Y 41 To Y 43Each can be independently O, S, N(R) 45 ), B(R) 45 ), C(R 45 (R) 46 ) or Si(R 45 (R) 46 ),
[0134] k41 can be 0 or 1, where when k41 is 0, -(Y 41 ) k41 - Does not exist.
[0135] A 41 To A 43 Each can be independently selected from C5-C. 30 Carbocyclic groups and C1-C 30 Heterocyclic groups,
[0136] R 41 To R 46 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C groups. 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -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 41 To R46 (For example, adjacent R) 41 To R 46 They can optionally be connected to each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups,
[0137] b41 to b43 can each be an integer from 0 to 10 independently, and
[0138] Q1 to Q3, Q 21 To Q 23 and Q 31 To Q 33 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiols, C1-C 60 heteroaryl groups, C1-C 60 heteroaryloxy groups, C1-C 60 Heteroaryl thio groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, biphenyl groups, and terphenyl groups.
[0139] For example, R selected from Equation 1 11 To R 19 At least one of them can be made by *-(L 11 ) a11 -A 11 The group indicated.
[0140] For example, X in Equation 1 11 It can be N(R) 19 ).
[0141] For example, R in Equation 1 11 To R 20 Each can be selected independently from:
[0142] From *-(L 11 )a11 -A 11 The indicated groups are hydrogen, deuterium, and C1-C. 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, phenanthrene groups, benzo[a]phenanthrene groups, Benzyl group, fluoranyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group, dinaphthothiophenyl group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2) and -N(Q1)(Q2);
[0143] Each was selected from deuterium, C1-C 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, phenanthrene groups, benzo[a]phenanthrene groups, Fiberyl group, fluorenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group, dinaphthothiophenyl group, -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 At least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group, Fiberyl group, fluorenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group and dinaphthothiophenyl group; and
[0144] Each was selected independently from deuterium, C1-C 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, phenanthrene groups, benzo[a]phenanthrene groups, Fiberyl group, fluorenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group, dinaphthothiophenyl group, -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 At least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group, At least one substituted phenyl group, biphenyl group, terphenyl group, naphthiophene group, carbazole group, dibenzofuranyl group, dibenzothiophene group, benzofuranyl group, benzocarbazole group, benzonaphthiophene group, benzonaphthiophene group, dibenzofuranyl group, dibenzonaphthiophene group, and dibenzonaphthiophene group selected from the following groups: phenyl group, biphenyl group, triphenyl group, naphthyl group, phenanthrene group, benzophenanthrene group, etc. Benzyl group, fluoranyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group and dinaphthothiophenyl group.
[0145] For example, L in Equation 1 11 You can choose from:
[0146] Phenyl group, naphthyl group, phenatene group, anthracene group, fluoranthene group, benzophenanthrene group, phenanthrene group, pyrene group, Groups, perylene groups, fluorene groups, carbazole groups, dibenzofuran groups, dibenzothiophene groups, -C(Q1)(Q2)- and -Si(Q1)(Q2)-; and
[0147] Each was selected from deuterium, C1-C 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, phenanthrene groups, benzo[a]phenanthrene groups, Fiberyl group, fluorenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group, dinaphthothiophenyl group, -C(Q 31 (Q) 32 (Q) 33 ) and -Si(Q 31 (Q) 32 (Q) 33 At least one substituted phenyl group, naphthyl group, phenatene group, anthracene group, fluoranthene group, benzophenanthrene group, phenanthrene group, pyrene group, Groups, perylene groups, fluorene groups, carbazole groups, dibenzofuran groups, and dibenzothiophene groups.
[0148] In one implementation, L in Equation 1 11 You can choose from:
[0149] Phenyl groups, fluorene groups, carbazole groups, dibenzofuran groups, dibenzothiophene groups, -C(Q1)(Q2)- and -Si(Q1)(Q2)-; and
[0150] Each was selected from deuterium, C1-C 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, fluorenyl groups, carbazole groups, dibenzofuranyl groups, dibenzothiophene groups, -C(Q) 31 (Q) 32 (Q) 33 ) and -Si(Q 31 (Q) 32 (Q) 33 At least one substituted phenyl group, fluorene group, carbazole group, dibenzofuran group and dibenzothiophene group in ().
[0151] For example, a11 in Equation 1 can be 1 or 2.
[0152] For example, A in Equation 1 11 You can choose from:
[0153] Phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group Benzyl group, fluoranyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group and dinaphthothiophenyl group;
[0154] Each was selected from deuterium, C1-C20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, phenanthrene groups, benzo[a]phenanthrene groups, Fiberyl group, fluorenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group, dinaphthothiophenyl group, -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 At least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group, Fiberyl group, fluorenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group and dinaphthothiophenyl group; and
[0155] Each was selected independently from deuterium, C1-C 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, phenanthrene groups, benzo[a]phenanthrene groups, Fiberyl group, fluorenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group, dinaphthothiophenyl group, -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 At least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group, At least one substituted phenyl group, biphenyl group, terphenyl group, naphthiophene group, carbazole group, dibenzofuranyl group, dibenzothiophene group, benzofuranyl group, benzocarbazole group, benzonaphthiophene group, benzonaphthiophene group, dibenzofuranyl group, dibenzonaphthiophene group, and dibenzonaphthiophene group selected from the following groups: phenyl group, biphenyl group, triphenyl group, naphthyl group, phenanthrene group, benzophenanthrene group, etc. Benzyl group, fluoranyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group and dinaphthothiophenyl group.
[0156] In one implementation, A in Equation 1 11 You can choose from:
[0157] Phenyl group, biphenyl group, triphenyl group, fluorenyl group, carbazole group, dibenzofuranyl group and dibenzothiophenyl group;
[0158] Each was selected from deuterium, C1-C 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, fluorenyl groups, carbazole groups, dibenzofuranyl groups, dibenzothiophene groups, -C(Q) 31 (Q) 32 (Q) 33 ) and -Si(Q 31 (Q) 32 (Q) 33 At least one substituted phenyl group, biphenyl group, terphenyl group, fluorenyl group, carbazole group, dibenzofuranyl group and dibenzothiophenyl group in the group; and
[0159] Each was selected independently from deuterium, C1-C 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, fluorenyl groups, carbazole groups, dibenzofuranyl groups, dibenzothiophene groups, -C(Q) 21 (Q) 22 (Q) 23 ) and -Si(Q 21 (Q) 22 (Q) 23 At least one substituted phenyl group, biphenyl group, terphenyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group in the group.
[0160] In one or more embodiments, A in Formula 1 11 It can be represented by one of the following equations 8-1 to 8-5:
[0161]
[0162] In equations 8-1 to 8-5,
[0163] X 81 It can be selected from O, S, N(R) 89 ) and C(R 89 (R) 90 ),
[0164] R 81 To R 90 Each can be independently selected from hydrogen, deuterium, and C1-C. 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, fluorenyl groups, carbazole groups, dibenzofuranyl groups, and dibenzothiophene groups, and
[0165] * indicates a binding site with an adjacent atom.
[0166] In one embodiment, the first compound may be represented by one of the following formulas 1-1 to 1-5:
[0167]
[0168] In equations 1-1 to 1-5,
[0169] L 11 a11, A 11 and R 11 To R 19 Each can be understood by referring to the description provided in Equation 1. That is, L 11 a11, A 11 and R 11 To R 19 Each can be the same as the definition in Equation 1.
[0170] For example, A in equations 1-1 to 1-5 11 It can be represented by one of the following equations 8-1 to 8-5:
[0171]
[0172] In equations 8-1 to 8-5,
[0173] X 81 It can be selected from O, S, N(R) 89 ) and C(R 89 (R) 90),
[0174] R 81 To R 90 Each can be independently selected from hydrogen, deuterium, and C1-C. 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, fluorenyl groups, carbazole groups, dibenzofuranyl groups, and dibenzothiophene groups, and
[0175] * indicates a binding site with an adjacent atom.
[0176] For example, R selected from Equation 2A 21 R 22 R 24 and R 25 At least one of them can be made by *-(L 21 ) a21 -A 21 The group represented, and at least one of the (6-k23) R in formula 2B. 23 It can be made by *-(L) 21 ) a21 -A 21 The group indicated.
[0177] For example, R in Equations 2A and 2B 21 To R 25 Each can be independently made by *-(L) 21 ) a21 -A 21 The groups represented are hydrogen, deuterium, -F, cyano groups, and C1-C. 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, phenanthrene groups, benzo[a]phenanthrene groups, Fiberyl group, fluorenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzo[fluorenyl group], benzo[carbazoleyl group], benzo[naphthofuranyl group, benzo[naphthothiophenyl group], dibenzo[fluorenyl group], dibenzo[carbazoleyl group], dibenzo[furanyl group], dibenzo[naphthothiophenyl group, indole[fluorenyl group], benzo[furan[fluorenyl group], benzo[thiophenyl group] Phenophenone group, indole carbazole group, indole carbazole group, benzofuran carbazole group, benzothiophene carbazole group, indole dibenzofuran group, indole dibenzofuran group, benzofuran dibenzofuran group, benzothiophene dibenzofuran group, indole dibenzothiophene group, indole dibenzothiophene group, benzofuran dibenzothiophene group, benzothiophene The following groups are included: phenazinothiophene group, pyridinyl group, pyrazinyl group, pyridinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, benzoisoquinolinyl group, naphridinyl group, quinoxalinyl group, quinazolinyl group, azafluorenyl group, azacarbazoleyl group, azadibenzofuranyl group, azadibenzothiophene group, diazafluorenyl group, diazacarbazoleyl group, diazadibenzofuranyl group, diazadibenzothiophene group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2);
[0178] Each is selected from deuterium, -F, cyano group, C1-C 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, phenanthrene groups, benzo[a]phenanthrene groups, Fiberyl group, fluorenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group, dinaphthothiophenyl group, indolefluorenyl group, indolefluorenyl group, benzofuran-fluorenyl group, benzothiophenefluorenyl group, indolecarbazole group, indolecarbazole group, benzofuran-carbazole group, benzothiophenecarbazole group, indoledibenzofuranyl ... Pheno-dibenzofuranyl group, indole-dibenzothiophenyl group, indole-dibenzothiophenyl group, benzofuran-dibenzothiophenyl group, benzothiophene-dibenzothiophenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, benzoisoquinolinyl group, naphridyl group, quinoxalinyl group, quinazolinyl group, azafluorenyl group, azacarbazoleyl group, aza-dibenzofuranyl group, aza-dibenzothiophenyl group, diazafluorenyl group, diazacarbazoleyl group, diaza-dibenzofuranyl group, diaza-dibenzothiophenyl group, -C(Q 31 (Q) 32 (Q) 33 ), -Si(Q 31 (Q) 32 (Q) 33 -B(Q) 31 (Q) 32 -N(Q) 31 (Q) 32 -S(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) and -P(=S)(Q 31 (Q) 32 At least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group, Fiberyl group, fluorenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzo[fluorenyl group, benzo[carbazoleyl group, benzo[naphthofuranyl group, benzo[naphthothiophenyl group, dibenzofluorenyl group, dibenzo[carbazoleyl group, dibenzo[naphthofuranyl group, dibenzothiophenyl group, indole[fluorenyl group, indole[fluorenyl group, benzo[furan[fluorenyl group, benzo[thiophene[fluorenyl group, indole[carbazoleyl group, indole[carbazoleyl group, benzo[furan[carbazoleyl group, benzo[thiophene[carbazoleyl group, indole[dibenzofuranyl group, indole[dibenzofuranyl group, benzo[furan[dibenzofuranyl group, benzo[]] Thiophene-dibenzofuranyl group, indole-dibenzothiophenyl group, indolo-dibenzothiophenyl group, benzofuran-dibenzothiophenyl group, benzothiophene-dibenzothiophenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, benzoisoquinolinyl group, naphridyl group, quinoxalinyl group, quinazolinyl group, azafluorenyl group, azacarbazoleyl group, azadibenzofuranyl group, azadibenzothiophenyl group, diazafluorenyl group, diazacarbazoleyl group, diazadibenzofuranyl group and diazadibenzothiophenyl group; and
[0179] Each is selected independently from deuterium, -F, cyano groups, C1-C 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, phenanthrene groups, benzo[a]phenanthrene groups, Fiberyl group, fluorenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group, dinaphthothiophenyl group, indolefluorenyl group, indolefluorenyl group, benzofuran-fluorenyl group, benzothiophenefluorenyl group, indolecarbazole group, indolecarbazole group, benzofuran-carbazole group, benzothiophenecarbazole group, indoledibenzofuranyl ... Pheno-dibenzofuranyl group, indole-dibenzothiophenyl group, indole-dibenzothiophenyl group, benzofuran-dibenzothiophenyl group, benzothiophene-dibenzothiophenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, benzoisoquinolinyl group, naphridyl group, quinoxalinyl group, quinazolinyl group, azafluorenyl group, azacarbazoleyl group, aza-dibenzofuranyl group, aza-dibenzothiophenyl group, diazafluorenyl group, diazacarbazoleyl group, diaza-dibenzofuranyl group, diaza-dibenzothiophenyl group, -C(Q 21 (Q) 22 (Q) 23 ), -Si(Q 21 (Q) 22 (Q) 23 -B(Q) 21 (Q) 22 -N(Q) 21 (Q) 22 -S(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) and -P(=S)(Q 21 (Q) 22 At least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group, Fiberyl group, fluorenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group, dinaphthothiophenyl group, indolefluorenyl group, indolefluorenyl group, benzofuran-fluorenyl group, benzothiophenefluorenyl group, indolecarbazole group, indolecarbazole group, benzofuran-carbazole group, benzothiophenecarbazole group, indoledibenzofuranyl group, indoledibenzofuranyl group, benzofuran-dibenzofuranyl group, benzothiophenedibenzofuranyl group, indoledibenzothiophene group The following groups are included: indolodibenzothiophene group, benzofuranodibenzothiophene group, benzothiophene benzodibenzothiophene group, pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, benzoisoquinolinyl group, naphridyl group, quinoxalinyl group, quinazolinyl group, azafluorenyl group, azacarbazoleyl group, azadibenzofuranyl group, azadibenzothiophene group, diazafluorenyl group, diazacarbazoleyl group, diazadibenzofuranyl group, and diazadibenzothiophene group, with at least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzophenanthrene group, etc. Fiberyl group, fluorenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzo[fluorenyl group, benzo[carbazoleyl group, benzo[naphthofuranyl group, benzo[naphthothiophenyl group, dibenzofluorenyl group, dibenzo[carbazoleyl group, dibenzo[naphthofuranyl group, dibenzothiophenyl group, indole[fluorenyl group, indole[fluorenyl group, benzo[furan[fluorenyl group, benzo[thiophene[fluorenyl group, indole[carbazoleyl group, indole[carbazoleyl group, benzo[furan[carbazoleyl group, benzo[thiophene[carbazoleyl group, indole[dibenzofuranyl group, indole[dibenzofuranyl group, benzo[furan[dibenzofuranyl group, benzo[]] Thiophene-dibenzofuranyl group, indole-dibenzothiophenyl group, indolene-dibenzothiophenyl group, benzofuran-dibenzothiophenyl group, benzothiophenene-dibenzothiophenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, benzoisoquinolinyl group, naphridyl group, quinoxalinyl group, quinazolinyl group, azafluorenyl group, azacarbazoleyl group, azadibenzofuranyl group, azadibenzothiophenyl group, diazafluorenyl group, diazacarbazoleyl group, diazadibenzofuranyl group and diazadibenzothiophenyl group, and
[0180] Q1 to Q3, Q 21 To Q23 and Q 31 To Q 33 Each can be understood by referring to the corresponding descriptions provided in this article.
[0181] For example, L in Equations 2A and 2B 21 You can choose from:
[0182] Phenyl group, naphthyl group, phenatene group, anthracene group, fluoranthene group, benzophenanthrene group, phenanthrene group, pyrene group, Groups, perylene groups, pyridine groups, pyrimidine groups, pyrazine groups, pyridazine groups, triazine groups, quinoline groups, isoquinoline groups, benzo[a]quinoline groups, benzo[a]isoquinoline groups, phthalazine groups, naphthidine groups, quinoxaline groups, benzo[a]quinoxaline groups, quinazoline groups, benzo[a]quinazoline groups, fluorene groups, carbazole groups, dibenzofuran groups, dibenzothiophene groups, -C(Q1)(Q2)-, -Si(Q1)(Q2)-, -S(=O)- and -P(=O)(Q1)-; and
[0183] Each is selected from deuterium, -F, cyano group, C1-C 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, phenanthrene groups, benzo[a]phenanthrene groups, Fiberyl group, fluorenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group, dinaphthothiophenyl group, indolefluorenyl group, indolefluorenyl group, benzofuran-fluorenyl group, benzothiophenefluorenyl group, indolecarbazole group, indolecarbazole group, benzofuran-carbazole group, benzothiophenecarbazole group, indoledibenzofuranyl ... Pheno-dibenzofuranyl group, indole-dibenzothiophenyl group, indole-dibenzothiophenyl group, benzofuran-dibenzothiophenyl group, benzothiophene-dibenzothiophenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, benzoisoquinolinyl group, naphridyl group, quinoxalinyl group, quinazolinyl group, azafluorenyl group, azacarbazoleyl group, aza-dibenzofuranyl group, aza-dibenzothiophenyl group, diazafluorenyl group, diazacarbazoleyl group, diaza-dibenzofuranyl group, diaza-dibenzothiophenyl group, -C(Q 31 (Q) 32 (Q) 33 ), -Si(Q 31 (Q) 32(Q) 33 -S(=O)(Q) 31 ) and -P(=O)(Q 31 (Q) 32 At least one substituted phenyl group, naphthyl group, phenatene group, anthracene group, fluoranthene group, benzophenanthrene group, phenanthrene group, pyrene group, Groups, perylene groups, pyridine groups, pyrimidine groups, pyrazine groups, pyridazine groups, triazine groups, quinoline groups, isoquinoline groups, benzo[a]quinoline groups, benzo[a]isoquinoline groups, phthalazine groups, naphthidine groups, quinoxaline groups, benzo[a]quinoxaline groups, quinazoline groups, benzo[a]quinazoline groups, fluorene groups, carbazole groups, dibenzofuran groups, and dibenzothiophene groups, and
[0184] Q1, Q2 and Q 31 To Q 33 Same as described above.
[0185] In one implementation, L in Formulas 2A and 2B 21 You can choose from:
[0186] Phenyl groups, pyridine groups, pyrimidine groups, pyrazine groups, pyridazine groups, triazine groups, fluorene groups, carbazole groups, dibenzofuran groups, dibenzothiophene groups, -C(Q1)(Q2)-, -Si(Q1)(Q2)-, -S(=O)- and -P(=O)(Q1)-; and
[0187] Each is selected from deuterium, -F, cyano group, C1-C 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, fluorenyl groups, carbazole groups, dibenzofuranyl groups, dibenzothiophenyl groups, pyridyl groups, pyrazinyl groups, pyrimidinyl groups, triazineyl groups, C(Q) 31 (Q) 32 (Q) 33 ), -Si(Q 31 (Q) 32 (Q) 33 -S(=O)(Q) 31 ) and -P(=O)(Q 31 (Q) 32 At least one substituted phenyl group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, fluorene group, carbazole group, dibenzofuran group and dibenzothiophene group, and
[0188] Q1, Q2 and Q 31 To Q 33 Same as described above.
[0189] For example, a21 in Equations 2A and 2B can be 1 or 2.
[0190] For example, A in Equation 2A and Equation 2B 21 You can choose from:
[0191] Phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group Fiberyl group, fluorenyl group, carbazoyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, naphthidyl group, quinoxalinyl group and quinazolinyl group;
[0192] Each is selected from deuterium, -F, cyano group, C1-C 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, phenanthrene groups, benzo[a]phenanthrene groups, Fiberyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, naphthidyl group, quinoxalinyl group, quinazolinyl group, -C(Q 31 (Q) 32 (Q) 33 ), -Si(Q 31 (Q) 32 (Q) 33 -B(Q) 31 (Q) 32 -N(Q) 31 (Q) 32 -S(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) and -P(=S)(Q 31 (Q) 32 At least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group, Fiberyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, naphthidyl group, quinoxalinyl group, and quinazolinyl group; and
[0193] Each is selected independently from deuterium, -F, cyano groups, C1-C 20Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, phenanthrene groups, benzo[a]phenanthrene groups, Fiberyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, naphthidyl group, quinoxalinyl group, quinazolinyl group, -C(Q 21 (Q) 22 (Q) 23 ), -Si(Q 21 (Q) 22 (Q) 23 -B(Q) 21 (Q) 22 -N(Q) 21 (Q) 22 -S(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) and -P(=S)(Q 21 (Q) 22 At least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group, At least one substituted phenyl group, biphenyl group, terphenyl group, naphthiophene group, benzo[a]phenanthryl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophene group, pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, naphthidyl group, quinoxalinyl group, and quinazolinyl group, or biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group, etc. Fiberyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, naphthidyl group, quinoxalinyl group and quinazolinyl group, and
[0194] Q 21 To Q 23 and Q 31 To Q 33 Each can be understood by referring to the corresponding descriptions provided in this article.
[0195] In one implementation, A in Equation 2A 21 A in sum 2B 21 Each can be selected independently from:
[0196] Phenyl group, biphenyl group, triphenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, pyridyl group, pyrazinyl group, pyridinyl group, pyrimidinyl group, and triazinyl group;
[0197] Each is selected from deuterium, -F, cyano group, C1-C 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, fluorenyl groups, carbazole groups, dibenzofuranyl groups, dibenzothiophenyl groups, pyridyl groups, pyrazinyl groups, pyrimidinyl groups, triazineyl groups, -C(Q) 31 (Q) 32 (Q) 33 ), -Si(Q 31 (Q) 32 (Q) 33 ) and -P(=O)(Q 31 (Q) 32 At least one substituted phenyl group, biphenyl group, terphenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, pyridyl group, pyrazinyl group, pyridinyl group, pyrimidinyl group, and triazinyl group in the group; and
[0198] Each is selected independently from deuterium, -F, cyano groups, C1-C 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, fluorenyl groups, carbazole groups, dibenzofuranyl groups, dibenzothiophenyl groups, pyridyl groups, pyrazinyl groups, pyrimidinyl groups, triazineyl groups, -C(Q) 21 (Q) 22 (Q) 23 ), -Si(Q 21 (Q) 22 (Q) 23 ) and -P(=O)(Q 21 (Q) 22 At least one substituted phenyl group, biphenyl group, terphenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, and triazinyl group selected from the group consisting of, and
[0199] Q 21 To Q 23 and Q 31 To Q 33Each can be understood by referring to the corresponding descriptions provided in this article.
[0200] In one embodiment, the second compound may be represented by one of the following formulas 2-1 and 2-2:
[0201]
[0202] In equations 2-1 and 2-2,
[0203] X 21 It can be selected from O, S, N(R) 24 ) and C(R 24 (R) 25 ),
[0204] R 21a To R 21c R 22a To R 22d R 23a To R 23e R 24 and R 25 Each can be selected independently from:
[0205] From *-(L 21 ) a21 -A 21 The groups represented are hydrogen, deuterium, -F, cyano groups, and C1-C. 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2);
[0206] Each is selected from deuterium, -F, cyano group, C1-C 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q) 31 (Q) 32 (Q) 33 ), -Si(Q 31 (Q) 32 (Q) 33 -B(Q) 31 (Q) 32 -N(Q) 31 (Q) 32 -S(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q)32 ) and -P(=S)(Q 31 (Q) 32 At least one substituted cyclic group containing π-electron-depleted nitrogen and a cyclic group not containing π-electron-depleted nitrogen; and
[0207] Each is selected independently from deuterium, -F, cyano groups, C1-C 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q) 21 (Q) 22 (Q) 23 ), -Si(Q 21 (Q) 22 (Q) 23 -B(Q) 21 (Q) 22 -N(Q) 21 (Q) 22 -S(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) and -P(=S)(Q 21 (Q) 22 At least one substituted cyclic group containing π-electron-depleted nitrogen and at least one substituted cyclic group not containing π-electron-depleted nitrogen in the cyclic group of )
[0208] R selected from Equation 2-1 21a To R 21c R 22a To R 22d R 24 and R 25 At least one of them can be made by *-(L 21 ) a21 -A 21 The group represented,
[0209] R selected from Equation 2-2 23a To R 23e At least one of them can be made by *-(L 21 ) a21 -A 21 The indicated groups, and
[0210] Q1 to Q3, Q 21 To Q 23 and Q 31 To Q 33Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiols, C1-C 60 heteroaryl groups, C1-C 60 heteroaryloxy groups, C1-C 60 Heteroaryl thio groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, biphenyl groups, and terphenyl groups.
[0211] 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).
[0212] In one implementation, M in Equation 3 31 It can be selected from Pt and Ir.
[0213] For example, A in Equations 3A to 3D 31 To A 34 Each of these can be independently i) a first ring, ii) a second ring, iii) a fused ring in which two or more first rings are fused together, iv) a fused ring in which two or more second rings are fused together, or v) a fused ring in which one or more first rings and one or more second rings are fused together.
[0214] The first ring can be selected from cyclopentyl groups, cyclopentenyl groups, cyclopentadienyl groups, furan groups, thiophene groups, pyrrole groups, borocyclopentadienyl groups, phosphacyclopentadienyl groups, thiophene groups, germanium heterocyclopentadienyl groups, selenophene groups, oxazole groups, dihydrooxazole groups, isoxazole groups, dihydroisooxazole groups, oxadiazole groups, dihydrooxadiazole groups, isoxadiazole groups, dihydroisooxadiazole groups, oxtriazole groups, dihydrooxtriazole groups, isoxtriazole groups, dihydroiso ... Zyrazole group, thiazole group, dihydrothiazole group, isothiazole group, dihydroisothiazole group, thiadiazole group, dihydrothiadiazole group, isothiazole group, dihydroisothiadiazole group, thiatriazole group, dihydrothiatriazole group, isothiazole group, dihydroisothiatriazole group, pyrazole group, dihydropyrazole group, imidazole group, dihydroimidazole group, triazole group, dihydrotriazole group, tetraazole group, dihydrotetraazole group, azathiophene group, diazathiophene group and triazathiophene group, and
[0215] The second ring can be selected from cyclohexyl groups, cyclohexene groups, cyclohexadiene groups, adamantyl groups, norbornyl groups, norbornene groups, phenyl groups, pyridine groups, dihydropyridine groups, tetrahydropyridine groups, pyrimidine groups, dihydropyrimidine groups, tetrahydropyrimidine groups, pyrazine groups, dihydropyrazine groups, tetrahydropyrazine groups, pyridazine groups, dihydropyridazine groups, tetrahydropyridazine groups, and triazine groups.
[0216] In one implementation, A in Equations 3A to 3D 31 To A 34 Each group can be independently selected from phenyl groups, naphthyl groups, anthracene groups, phenanthrene groups, benzo[a]phenanthrene groups, pyrene groups, etc. Groups, furan groups, thiophene groups, thiophene groups, indene groups, fluorene groups, benzofuran groups, dibenzofuran groups, benzothiophene groups, dibenzothiophene groups, benzothiophene groups, dibenzothiophene groups, indole groups, carbazole groups, indole-pyridine groups, indole-pyridine groups, benzofuran-pyridine groups, benzothiophene-pyridine groups, benzothiophene-pyridine groups, indole-pyrimidine groups, indole-pyrimidine groups, benzofuran-pyrimidine groups, benzothiophene-pyrimidine groups, benzothiophene-pyrimidine groups, pyridine groups, pyrimidine groups, pyrazine groups, pyridazine groups, triazine groups, quinoline groups, isoquinoline groups, quinoxaline groups, quinazoline groups, cinnamon groups Phthalorazine group, phenanthrene-rhein group, pyrrole group, pyrazole group, imidazole group, dihydroimidazolium group, triazole group, dihydrotriazole group, oxazole group, dihydrooxazole group, isoxazole group, thiazole group, dihydrothiazole group, isothiazole group, oxadiazole group, dihydrooxadiazole group, thiadiazole group, dihydrothiadiazole group, benzopyrazole group, benzimidazole group, dihydrobenzimidazole group, imidazopyridine group, imidazopyrimidine group, imidazopyrazine group, benzoxazole group, dihydrobenzoxazole group, benzothiazole group, dihydrobenzothiazole group, benzoxadiazole group, dihydrobenzoxadiazole group, benzoxadiazole group, dihydrobenzoxadiazole group, and dihydrobenzothiadiazole group.
[0217] For example, T in Equations 3A to 3D 31 To T 34 Each can be independently selected from single bonds, double bonds, *-O-*', *-S-*', *-C(R) 35 (R) 36 )-*' and *-N(R 35 )-*'.
[0218] For example, Y in Equations 3A to 3D 31 To Y 34 Each can be independently selected from single bonds, *-O-*', and *-S-*'.
[0219] For example, R in Equations 3A to 3D 31 To R 38 Each can be selected independently from:
[0220] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 alkyl groups and C1-C 20 alkoxy group;
[0221] Phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group Fiberyl group, fluorenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group, dinaphthothiophenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, naphridinyl group, quinoxalinyl group, quinazolinyl group, azafluorenyl group, azacarbazole group, azadibenzofuranyl group, azadibenzothiophenyl group, diazafluorenyl group, diazacarbazole group, diazadibenzofuranyl group and diazadibenzothiophenyl group;
[0222] Each is selected from deuterium, -F, -Cl, -Br, -I, cyano groups, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group Fiberyl group, fluoranyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group, dinaphthothiophenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, iso At least one substituted phenyl group, biphenyl group, terphenyl group, naphthiol group, quinoxalinyl group, quinazolinyl group, azifluorenyl group, azicarbazolyl group, azidibenzofuranyl group, azidibenzothiophene group, diazafluorenyl group, diazacarbazolyl group, diazadibenzofuranyl group, and diazadibenzothiophene group selected from the following groups: quinolinyl group, naphthiol group, phenanthrene group, benzo[a]phenanthrene group. Fiberyl group, fluorenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group, dinaphthothiophenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, naphridinyl group, quinoxalinyl group, quinazolinyl group, azafluorenyl group, azacarbazole group, azadibenzofuranyl group, azadibenzothiophenyl group, diazafluorenyl group, diazacarbazole group, diazadibenzofuranyl group and diazadibenzothiophenyl group; and
[0223] -B(Q1)(Q2) and -N(Q1)(Q2), and
[0224] Q1 and Q2 can be selected independently from:
[0225] Hydrogen, deuterium and C1-C 20 alkyl groups;
[0226] Phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group Fiberyl group, fluorenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group, dinaphthothiophenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, naphridinyl group, quinoxalinyl group, quinazolinyl group, azafluorenyl group, azacarbazole group, azadibenzofuranyl group, azadibenzothiophenyl group, diazafluorenyl group, diazacarbazole group, diazadibenzofuranyl group and diazadibenzothiophenyl group; and
[0227] Each was selected from deuterium, C1-C 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, phenanthrene groups, benzo[a]phenanthrene groups, Fiberyl group, fluoranyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group, dinaphthothiophenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, iso At least one substituted phenyl group, biphenyl group, terphenyl group, naphthiol group, quinoxalinyl group, quinazolinyl group, azifluorenyl group, azicarbazolyl group, azidibenzofuranyl group, azidibenzothiophene group, diazafluorenyl group, diazacarbazolyl group, diazadibenzofuranyl group, and diazadibenzothiophene group selected from the following groups: quinolinyl group, naphthiol group, phenanthrene group, benzo[a]phenanthrene group. Fiberyl group, fluorenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group, dinaphthothiophenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, naphridinyl group, quinoxalinyl group, quinazolinyl group, azafluorenyl group, azacarbazole group, azadibenzofuranyl group, azadibenzothiophenyl group, diazafluorenyl group, diazacarbazole group, diazadibenzofuranyl group and diazadibenzothiophenyl group.
[0228] In one implementation, R in Equations 3A to 3D 31 To R 38 Each can be selected independently from:
[0229] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, methoxy group, ethoxy group, propoxy group and butoxy group;
[0230] Phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group Fiberyl group, fluorenyl group, carbazole group, dibenzofuranyl group and dibenzothiophenyl group;
[0231] Each is selected from deuterium, -F, -Cl, -Br, -I, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, methoxy group, ethoxy group, propoxy group, butoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group, At least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthryl group, carbazole group, dibenzofuranyl group, and dibenzothiophenyl group selected from the following groups: phenyl group, fluoranyl group, fluorenyl group, carbazoyl group, dibenzofuranyl group, and dibenzothiophenyl group; Fiberyl group, fluorenyl group, carbazole group, dibenzofuranyl group and dibenzothiophenyl group; and
[0232] -B(Q1)(Q2) and -N(Q1)(Q2), and
[0233] Q1 and Q2 can be independently selected from: hydrogen, deuterium, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group and tert-butyl group;
[0234] Phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group Fiberyl group, fluorenyl group, carbazole group, dibenzofuranyl group and dibenzothiophenyl group; and
[0235] Each group is selected from deuterium, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group, etc. At least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthryl group, carbazole group, dibenzofuranyl group, and dibenzothiophenyl group selected from the following groups: phenyl group, fluoranyl group, fluorenyl group, carbazoyl group, dibenzofuranyl group, and dibenzothiophenyl group; Fiberyl group, fluorenyl group, carbazoyl group, dibenzofuranyl group and dibenzothiophenyl group.
[0236] In one embodiment, the third compound may be represented by one of the following formulas: Formula 3-1 and Formula 3-2:
[0237]
[0238]
[0239] In equations 3-1 and 3-2,
[0240] X 31 To X 40 They can be independently selected from N and C, and
[0241] The remaining components can be understood by referring to their respective descriptions provided in this document.
[0242] In equations 3-1 and 3-2, X 31 and X 32 Each can be A independently 31 The ring members, and X 33 To X 40 This can also be understood by referring to the descriptions provided for Equations 3-1 and 3-2. That is, X 33 To X 40 Each can be N or C independently.
[0243] For example, X in Equation 4 41 It can be selected from N and B.
[0244] For example, Y in Equation 4 41 To Y 43 Each can be independently selected from O, S, N(R) 45 ) and B(R 45 ).
[0245] For example, A in Equation 4 41 To A 43 Each group can be independently selected from phenyl groups, naphthyl groups, phenanthrene groups, anthracene groups, benzo[a]phenanthrene groups, pyrene groups, etc. Groups, pyridine groups, pyrazine groups, pyrimidine groups, triazine groups, quinoline groups, isoquinoline groups, benzoquinoline groups, benzoisoquinoline groups, 2,6-naphthidine groups, 1,8-naphthidine groups, 1,5-naphthidine groups, 1,6-naphthidine groups, 1,7-naphthidine groups, 2,7-naphthidine groups, quinoxaline groups, quinazolinoline groups, phenanthridine groups, phenanthroxaloline groups, benzofuran groups, benzothiophene groups, indole groups, indole groups, furanopyridine groups, thiophene groups Pyridine group, cyclopentanopyridine group, pyrrolopyridine group, dibenzofuran group, dibenzothiophene group, fluorene group, carbazole group, benzonaphthofuran group, benzonaphthothiophene group, benzofluorene group, benzocarbazole group, dinaphthofuran group, dinaphthothiophene group, dibenzofluorene group, dibenzocarbazole group, benzooxazole group, benzothiazole group, benzimidazole group, naphthofuran group, naphthothiophene group, spiro-difluorene group and spiro-fluorene-indene group; and
[0246] Groups represented by the following formula 4A:
[0247] Formula 4A
[0248]
[0249] In Equation 4A,
[0250] X 42 You can refer to X in Equation 4 41 To understand using the provided description,
[0251] Y 44 To Y 46 Each can refer to Y in Equation 4. 41 To Y 43 To understand using the provided description,
[0252] k44 can be understood by referring to the description provided regarding k41 in Equation 4.
[0253] A 44 To A 46 Each can refer to A in Equation 4. 41 To A43 To understand using the provided description,
[0254] R 47 To R 49 Each can refer to R in Equation 4. 41 To understand, and
[0255] b47 to b49 can each be understood by referring to the description provided for b41 in Equation 4.
[0256] In one embodiment, the fourth compound can be represented by the following formula 4-1:
[0257] Equation 4-1
[0258]
[0259] In Equation 4-1,
[0260] The components (i.e., the substituents and their respective numbers) can each be understood by referring to their corresponding descriptions provided herein with respect to Equation 4.
[0261] In one or more embodiments, the fourth compound may be represented by one of the following formulas 4-11 and 4-12:
[0262]
[0263] In equations 4-11 and 4-12,
[0264] R 41a To R 41d R 42a To R 42d R 43a To R 43c R 44a To R 44d R 45a R 45b and R 46a To R 46c Each can refer to R in Equation 4. 41 To understand, and
[0265] The remaining components can be understood by referring to their respective descriptions provided in this paper regarding Equation 4.
[0266] In one embodiment, the first compound may be selected from compounds of group I.
[0267] The second compound may be selected from compounds in Group II.
[0268] The third compound can be selected from compounds of Group III-I and Group III-II, and
[0269] The fourth compound may be selected from compounds in group IV:
[0270] Group I
[0271]
[0272]
[0273] Group II
[0274]
[0275]
[0276] Group III-I
[0277]
[0278]
[0279] Group III-II
[0280]
[0281]
[0282] Group IV
[0283]
[0284]
[0285] In Group III-I, compounds 1 to 5 are represented by the first structure of that group, having substituents R as defined in the respective structures. Compounds 6 to 20, 29 to 48, and 57 to 76 are similarly defined.
[0286] The first, second, and third compounds may be substantially non-luminescent. For example, the first, second, and third compounds may not emit any light, or the light emitted by the first, second, and third compounds may be only insignificant compared to the light emitted by other compounds (e.g., the fourth compound).
[0287] More specifically, the third compound may not emit light, and instead, reverse intersystem crossing (RISC) and / or intersystem crossing (ISC) may actively occur therein, resulting in the delivery of triplet excitons generated from the first and second compounds to the fourth compound.
[0288] Therefore, by transferring singlet and triplet excitons generated in the emitter layer to a fourth compound, an organic light-emitting device with improved efficiency can be obtained. Furthermore, because an organic light-emitting device with significantly reduced energy loss is obtained, the lifetime characteristics of the organic light-emitting device can be improved.
[0289] Furthermore, since the excitons transition in the third compound and then in the fourth compound, the degradation of the fourth compound due to the energy of the excitons can be suppressed, thereby improving the lifespan characteristics of the organic light-emitting device.
[0290] The lowest excited triplet energy level of the third compound can be from 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, which allows the lowest triplet exciton of the third compound to easily transfer to the lowest excited singlet energy level of the fourth compound.
[0291] The fourth compound emits light, and the fourth compound can be a delayed fluorescence emitter. That is, the fourth compound is configured to emit light, and the fourth compound can be a delayed fluorescence emitting material.
[0292] In one or more embodiments, the fourth compound may be a thermally activated delayed fluorescence (TADF) emitter.
[0293] In one or more embodiments, the ratio of the emission component emitted from the fourth compound to the total emission component emitted from the emission layer may be 80% or greater. That is, the ratio of light emitted from the fourth compound to the total light emitted from the emission layer may be 80% or greater.
[0294] The fourth compound may have a maximum emission wavelength of about 420 nm to about 490 nm, but embodiments of the present disclosure are not limited thereto.
[0295] More specifically, the fourth compound in the emission layer can emit blue delayed fluorescence by receiving energy from excitons (formed in other compounds) without directly participating in exciton formation.
[0296] The fourth compound can satisfy condition 1:
[0297] Condition 1
[0298] △E ST (C4)≤0.3eV
[0299] In condition 1,
[0300] △E ST (C4) is the lowest excited singlet state energy level (E) of the fourth compound. S1(C4) and the lowest excited triplet energy level (E T1 The difference between (C4)).
[0301] Here, E S1 (C4) and E T1 (C4) can be evaluated using density function theory (DFT) methods of Gaussian procedures with structural optimization at the B3LYP / 6-31G(d,p) level.
[0302] The fourth compound has a relatively higher T1 level than typical fluorescent dopants, which can facilitate reverse system-to-system crossing (RISC).
[0303] In related technologies (e.g., typical) fluorescent dopants (e.g., DCJTB), the T1 level is significantly lower than that of the third compound. Therefore, excitons at the T1 level generated by the third compound may transition to the T1 level of the fluorescent dopant, and even after the transition, the excitons may not participate in light emission and can be quenched. Furthermore, due to the low T1 level of the fluorescent dopant, triplet excitons generated in the first and second compounds may be quenched without participating in light emission, while simultaneously transitioning to the T1 level of the fluorescent dopant, rather than the T1 level of the third compound. Therefore, replacing the fourth compound with another typical fluorescent dopant would be inappropriate. That is, when the fourth compound is replaced with a fluorescent dopant from another related technology, the light emission efficiency will be significantly reduced.
[0304] However, because the fourth compound exhibits sufficiently high RISC efficiency even at room temperature, when excitons at the T1 level of the third compound migrate to the T1 level of the fourth compound, the excitons at the T1 level of the fourth compound also undergo a reverse intersystematic transition to the S1 level of the fourth compound and are then emitted as fluorescence. In other words, the excitons are not quenched. Therefore, the likelihood of exciton-quenching can be significantly reduced, and luminescence efficiency can be improved. Furthermore, because the excitons transition in the third compound and then in the fourth compound, degradation of the fourth compound due to exciton energy can be suppressed, thereby improving lifetime characteristics.
[0305] Typically, when electrons are not effectively injected from the electron transport region into the emitter layer, charge accumulates at the interface between the emitter layer and the electron transport region, causing interface degradation. Conversely, when holes are not effectively injected from the hole transport region into the emitter layer, charge accumulates at the interface between the emitter layer and the hole transport region, also causing interface degradation. This reduces the lifespan of the organic light-emitting device.
[0306] Because the second compound inherently contains an electron transport component, it can be used (e.g., readily) to modulate the electron transport characteristics of the organic light-emitting device. Because the first compound does not contain an electron transport component, it can be used (e.g., readily) to modulate the hole transport characteristics of the organic light-emitting device. In this way, the charge balance in the emitting layer of the organic light-emitting device can be enhanced or optimized.
[0307] Based on the total weight of the emitter layer, the amount of the first compound in the emitter layer is from about 10% to about 90% by weight.
[0308] Based on the total weight of the emitter layer, the amount of the second compound in the emitter layer can be from about 10% by weight to about 90% by weight.
[0309] The amount of the third compound in the emitter layer can be greater than or equal to the amount of the fourth compound.
[0310] Based on the total weight of the emitter layer, the amount of the fourth compound in the emitter layer can be from about 0.25% by weight to about 5% by weight.
[0311] Based on the sum of 100 parts by weight of the first compound and the second compound, the amount of the fourth compound may be from about 0.01 parts by weight to about 20 parts by weight.
[0312] When the first, second, third, and fourth compounds are within these respective ranges, an organic light-emitting device with both improved efficiency and improved lifespan can be provided.
[0313] In one or more embodiments, the emission layer may consist of (i.e., only) the first compound, the second compound, the third compound, and the fourth compound, but the embodiments of this disclosure are not limited thereto.
[0314] In one embodiment, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may further include a hole transport region between the first electrode and the emitter layer and / or an electron transport region between the emitter layer and the second electrode. The hole transport region may include a hole injection layer, a hole transport layer, an emitter auxiliary layer, and / or an electron blocking layer, and the electron transport region may include a hole blocking layer, an electron transport layer, and / or an electron injection layer, but the embodiments of this disclosure are not limited thereto.
[0315] For example, the hole-blocking layer may contain a hole-blocking material represented by the following formula 10:
[0316] Formula 10
[0317]
[0318] In Equation 10,
[0319] L 101 To L 103 Each can be independently selected from substituted or unsubstituted C5-C. 30 Carbocyclic groups and substituted or unsubstituted C1-C 30 Heterocyclic groups;
[0320] a101 to a103 can each be independently selected from 0, 1, and 2, and
[0321] R 101 To R 103 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -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).
[0322] For example, L in Equation 10 101 To L 103 Each can be selected independently from:
[0323] Phenyl group, naphthyl group, phenatene group, anthracene group, fluoranthene group, benzophenanthrene group, phenanthrene group, pyrene group, Groups, perylene groups, pyridine groups, pyrimidine groups, pyrazine groups, pyridazine groups, triazine groups, quinoline groups, isoquinoline groups, benzo[a]quinoline groups, benzo[a]isoquinoline groups, phthalazine groups, naphthidine groups, quinoxaline groups, benzo[a]quinoxaline groups, quinazoline groups, benzo[a]quinazoline groups, fluorene groups, carbazole groups, dibenzofuran groups, and dibenzothiophene groups; and
[0324] Each is selected from deuterium, -F, cyano group, C1-C 20Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, phenanthrene groups, benzo[a]phenanthrene groups, Fiberyl group, fluorenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group, dinaphthothiophenyl group, indolefluorenyl group, indolefluorenyl group, benzofuran-fluorenyl group, benzothiophenefluorenyl group, indolecarbazole group, indolecarbazole group, benzofuran-carbazole group, benzothiophenecarbazole group, indoledibenzofuranyl group, indoledibenzofuranyl group, benzofuran-dibenzofuranyl group, benzothiophenedibenzofuranyl group, indoledibenzothiophene group At least one substituted phenyl group, naphthyl group, phenatene group, anthracene group, benzothiophene group, pyridyl group, pyrazinyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, benzoisoquinolinyl group, naphthidyl group, quinoxalinyl group, quinazolinyl group, azafluorenyl group, azacarbazoleyl group, azadibenzofuranyl group, azadibenzothiophene group, diazafluorenyl group, diazacarbazoleyl group, diazadibenzofuranyl group, and diazadibenzothiophene group, or a substituted phenyl group, naphthyl group, phenatene group, phenanthrene group, fluoranthene group, benzophenanthrene group, phenanthrene group, pyrene group, indole-dibenzothiophene group, benzofuranyl group, benzothiophene ...benzothiophene group, phenanthrene group, pyrene group, indole-dibenzothiophene group, benzofuranyl group, benzothiophene group, benzothiophene group, phenanthrene group, pyrene group, indole-dibenzothiophene group, benzofuranyl group, benzothiophene group, benzothiophene group, benzothiophene group, benzothiophene group, Groups, perylene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzo[a]quinoline group, benzo[a]isoquinoline group, phthalazine group, naphthidine group, quinoxaline group, benzo[a]quinoxaline group, quinazoline group, benzo[a]quinazoline group, fluorene group, carbazole group, dibenzofuran group, and dibenzothiophene group.
[0325] For example, a101 to a103 in Equation 10 can each be 0 or 1 independently.
[0326] For example, R in Equation 10 101 To R 103 Each can be selected independently from:
[0327] Each unsubstituted group or selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 10 Alkyl groups, C1-C 10Alkoxy group, phenyl group, biphenyl group, naphthyl group, phenateninyl group, anthracene group, phenanthrene group, pyridyl group, pyrazinyl group, pyridazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzo[a]quinolinyl group, benzo[a]isoquinolinyl group, phthalazinyl group, naphthidyl group, quinoxalinyl group, quinazolinyl group, benzo[a]quinoxalinyl group, benzo[a]quinazolinyl group, fluorenyl group, carbazoleyl group, dibenzofuranyl group, dibenzothiophenyl group, azafluorenyl group, azacarbazoleyl group, azadibenzofuranyl group, azadibenzothiophenyl group, diazafluorenyl group, diazacarbazoleyl group, diazadibenzofuranyl group, diazadibenzothiophenyl group, -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 At least one substituted phenyl group, biphenyl group, naphthyl group, phenarenyl group, anthracene group, phenanthryl group, pyridyl group, pyrazinyl group, pyridazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzo[a]quinolinyl group, benzo[a]isoquinolinyl group, phthalazinyl group, naphthidyl group, quinoxalinyl group, quinazolinyl group, benzo[a]quinoxalinyl group, benzo[a]quinazolinyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, azafluorenyl group, azacarbazoleyl group, azadibenzofuranyl group, azadibenzothiophenyl group, diazafluorenyl group, diazacarbazoleyl group, diazadibenzofuranyl group and diazadibenzothiophenyl group; and
[0328] -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),
[0329] Q1 to Q3 and Q 31 To Q 33 Each group can be independently selected from phenyl groups, biphenyl groups, naphthyl groups, phenaren groups, anthracene groups, phenanthrene groups, pyridyl groups, pyrazinyl groups, pyridazinyl groups, pyrimidinyl groups, triazinyl groups, quinolinyl groups, isoquinolinyl groups, benzo[a]quinolinyl groups, benzo[a]isoquinolinyl groups, phthalazinyl groups, naphthidyl groups, quinoxalinyl groups, quinazolinyl groups, benzo[a]quinoxalinyl groups, benzo[a]quinazolinyl groups, fluorenyl groups, carbazole groups, dibenzofuranyl groups, dibenzothiophenyl groups, azafluorenyl groups, azacarbazole groups, azadibenzofuranyl groups, azadibenzothiophenyl groups, diazafluorenyl groups, diazacarbazole groups, diazadibenzofuranyl groups, and diazadibenzothiophenyl groups.
[0330] In one implementation, R in Equation 10 101 To R 103 Each can be independently selected from its own unsubstituted or selected from deuterium, C1-C 10 Alkyl groups, phenyl groups, biphenyl groups, naphthyl groups, phenerenoyl groups, anthracene groups, phenanthrene groups, fluorenyl groups, carbazole groups, dibenzofuranyl groups, dibenzothiophene groups, -C(Q 31 (Q) 32 (Q) 33 ) and -Si(Q 31 (Q) 32 (Q) 33 At least one substituted phenyl group, biphenyl group, naphthyl group, phenatenyl group, anthracene group, phenanthryl group, fluorenyl group, carbazole group, dibenzofuranyl group and dibenzothiophenyl group in the group; and
[0331] -C(Q1)(Q2)(Q3) and -Si(Q1)(Q2)(Q3), and
[0332] Q1 to Q3 and Q 31 To Q 33 Each group can be independently selected from phenyl groups, biphenyl groups, naphthyl groups, phenatenyl groups, anthracene groups, phenanthrene groups, fluorenyl groups, carbazole groups, dibenzofuranyl groups, and dibenzothiophene groups.
[0333] In one implementation, R is selected from Formula 10. 101 To R 103 At least one of the groups can be selected from the group represented by formula 11-1, the group represented by formula 11-2, -C(Q1)(Q2)(Q3), and -Si(Q1)(Q2)(Q3):
[0334]
[0335] In Equations 11-1 and 11-2,
[0336] Y 111 It can be selected from phenyl groups, biphenyl groups, naphthyl groups, phenerenoyl groups, anthracene groups, phenanthrene groups, fluorenyl groups, carbazole groups, dibenzofuranyl groups, dibenzothiophene groups, -C(Q 31 (Q) 32 (Q) 33 ) and -Si(Q 31 (Q) 32 (Q) 33 ),
[0337] R 111 To R 114 Each can be independently selected from hydrogen, deuterium, and C1-C. 10 Alkyl groups, phenyl groups, biphenyl groups, naphthyl groups, phenerenoyl groups, anthracene groups, phenanthrene groups, fluorenyl groups, carbazole groups, dibenzofuranyl groups, dibenzothiophene groups, -C(Q 31 (Q) 32 (Q) 33 ) and -Si(Q 31 (Q) 32 (Q) 33 ),
[0338] Q1 to Q3 and Q 31 To Q 33 Each group can be independently selected from phenyl groups, biphenyl groups, naphthyl groups, phenerenoyl groups, anthracene groups, phenanthrene groups, fluorenyl groups, carbazole groups, dibenzofuranyl groups, and dibenzothiophene groups, as well as...
[0339] * indicates a binding site with an adjacent atom.
[0340] For example, hole-blocking materials can be selected from compounds of group V:
[0341]
[0342]
[0343] The hole-blocking material may be the same as or different from the second compound. In one embodiment, the hole-blocking material may be different from the second compound.
[0344] Figure 1 Description
[0345] Figure 1 This is a schematic view of an organic light-emitting device 10 according to an embodiment. The organic light-emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.
[0346] In the following text, we will discuss... Figure 1 The structure of the organic light-emitting device 10 according to the embodiment and the method of manufacturing the organic light-emitting device 10 are described.
[0347] [First Electrode 110]
[0348] exist Figure 1 In this configuration, the substrate may additionally be 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 (e.g., excellent) mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and / or water resistance.
[0349] The first electrode 110 can 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 can be selected from materials with high work function to facilitate hole injection.
[0350] The first electrode 110 can be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material used to form the first electrode can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof, but the embodiments of this disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transparent electrode or a reflective electrode, the material used to form the first electrode 110 can 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 this disclosure are not limited thereto.
[0351] The first electrode 110 may have a single-layer structure or a multi-layer structure comprising 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 to this.
[0352] Organic layer 150
[0353] The organic layer 150 is located on the first electrode 110. The organic layer 150 may include an emitter layer.
[0354] The organic layer 150 may further include a hole transport region between the first electrode 110 and the emitter layer and an electron transport region between the emitter layer and the second electrode 190.
[0355] Hole transport region in organic layer 150
[0356] The hole transport region may have i) a single-layer structure comprising a single layer of a single material, ii) a single-layer structure comprising a single layer of multiple different materials, or iii) a multi-layer structure comprising multiple layers of multiple different materials.
[0357] The hole transport region may include at least one layer selected from the hole injection layer, hole transport layer, emission assist layer and electron blocking layer.
[0358] For example, the hole transport region may have a single-layer structure including a single layer containing multiple different materials, or a 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 / electron blocking layer structure, wherein for each structure, the constituent layers are stacked sequentially from the first electrode 110 in a predetermined order, but the structure of the hole transport region is not limited to this.
[0359] The hole transport region may contain 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"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), compounds represented by formula 201, and compounds represented by formula 202:
[0360]
[0361] Formula 201
[0362]
[0363] Formula 202
[0364]
[0365] In equations 201 and 202,
[0366] L 201 To L 204 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 arylene groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.
[0367] L 205 It can be selected from *-O-*', *-S-*', *-N(Q) 201 )-*', substituted or unsubstituted C1-C 20 alkylene groups, substituted or unsubstituted C2-C 20 alkenyl groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 arylene groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.
[0368] xa1 to xa4 can each be an integer from 0 to 3 independently.
[0369] xa5 can be an integer from 1 to 10, and
[0370] R 201 To R 204 and Q 201 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.
[0371] In one implementation, in formula 202, R 201 and R 202 They can optionally be linked to each other via single bonds, dimethyl-methylene groups, or diphenyl-methylene groups, and R 203 and R 204 They can be optionally linked together via single bonds, dimethyl-methylene groups, or diphenyl-methylene groups.
[0372] In one implementation, in formulas 201 and 202,
[0373] L 201 To L 205 Each can be selected independently from:
[0374] Phenylidene group, pentylene group, indenyl group, naphthyl group, chamomile cycloyl group, heptylene group, adamantyl group, acenaphthene group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenanthroline group, anthracene group, fluorenyl group, benzo[a]phenanthrene group, pyrene group, etc. Benzyl group, tetraphenyl group, puryl group, peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, rubidyl group, styrenyl group, furanyl group, carbazolyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzothiophenyl group and pyridylyl group; and
[0375] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 10Alkyl-substituted phenyl groups, -F-substituted phenyl groups, pentanenyl groups, indole groups, naphthyl groups, chamomile cycloyl groups, heptenyl groups, indoleyl groups, acenaphthyl groups, fluorenyl groups, spiro-difluorenyl groups, benzo[a]fluorenyl groups, dibenzo[a]fluorenyl groups, phenanthrenyl groups, anthraceneyl groups, fluoranthraceneyl groups, benzo[a]phenanthreneyl groups, pyrene groups, Benzyl group, tetraphenyl group, furanyl group, perylyl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, rutinyl group, kosyl group, ovoidyl group, thiophenyl group, furanyl group, carbazoleyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group, dibenzocarbazoleyl group, dibenzothiophenyl group, pyridyl group, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 At least one substituted phenylene group, pentylene group, indenyl group, naphthyl group, chamomile cycloyl group, heptylene group, adamantyl group, acenaphthene group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenenthene group, anthracene group, fluorenyl group, benzo[a]phenanthrene group, pyrene group, etc. The following groups are listed: alkyl group, tetraphenylene group, purylene group, perylene group, pentaphenylene group, hexaphenylene group, pentaphenylene group, rubidium benzoate group, styrenyl group, furanyl group, carbazolyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzothiophenyl group, and pyridylene group.
[0376] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl groups, C1-C 10 Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups.
[0377] In one or more implementations, xa1 to xa4 can each be 0, 1 or 2 independently.
[0378] In one or more implementations, xa5 can be 1, 2, 3 or 4.
[0379] In one or more implementations, R 201 To R 204 and Q 201 Each can be selected independently from:
[0380] Phenyl group, biphenyl group, terphenyl group, pentanenyl group, indole group, naphthyl group, chamomile cycloyl group, heptenyl group, indoleyl group, acenaphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthreneyl group, anthraceneyl group, fluoranthraceneyl group, benzo[a]phenanthreneyl group, pyrene group, Benzyl group, tetraphenyl group, furanyl group, perylyl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, rutinyl group, kosyl group, ovoidyl group, thiophenyl group, furanyl group, carbazoleyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group, dibenzocarbazoleyl group, dibenzothiophenyl group and pyridyl group; and
[0381] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 10 Alkyl-substituted phenyl groups, -F-substituted phenyl groups, pentanenyl groups, indole groups, naphthyl groups, chamomile cycloyl groups, heptenyl groups, indoleyl groups, acenaphthyl groups, fluorenyl groups, spiro-difluorenyl groups, benzo[a]fluorenyl groups, dibenzo[a]fluorenyl groups, phenanthrenyl groups, anthraceneyl groups, fluoranthraceneyl groups, benzo[a]phenanthreneyl groups, pyrene groups, Benzyl group, tetraphenyl group, furanyl group, perylyl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, rutinyl group, kosyl group, ovoidyl group, thiophenyl group, furanyl group, carbazoleyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group, dibenzocarbazoleyl group, dibenzothiophenyl group, pyridyl group, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32At least one substituted phenyl group, biphenyl group, terphenyl group, pentanenyl group, indole group, naphthyl group, chamomile cycloyl group, heptenyl group, indoleyl group, acenaphthenic group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthreneyl group, anthraceneyl group, fluoranthraceneyl group, benzo[a]phenanthreneyl group, pyreneyl group, The following groups are listed: alkyl group, tetraphenyl group, furanyl group, perylyl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, rutinyl group, kosyl group, ovoidyl group, thiophenyl group, furanyl group, carbazoleyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group, dibenzocarbazoleyl group, dibenzothiophenyl group, and pyridyl group.
[0382] Q 31 To Q 33 Same as described above.
[0383] In one or more embodiments, R selected from Formula 201 201 To R 203 At least one of them can be independently selected from:
[0384] Fluorenyl group, spiro-difluorenyl group, carbazole group, dibenzofuranyl group and dibenzothiophenyl group; and
[0385] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 10 At least one substituted fluorenyl group, spiro-difluorenyl group, carbazole group, dibenzofuranyl group, and dibenzothiophene group selected from the following groups: alkyl-substituted phenyl group, -F-substituted phenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, carbazole group, dibenzofuranyl group, and dibenzothiophene group.
[0386] However, the implementation of this disclosure is not limited to this.
[0387] In one or more implementations, in formula 202, i)R 201 and R 202 They can be connected to each other via a single key, and / or ii)R 203 and R 204They can be connected to each other via a single key.
[0388] In one or more embodiments, R in formula 202 201 To R 204 Each can be selected independently from:
[0389] Carbazolium group; and
[0390] Selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 10 At least one substituted carbazoyl group selected from the following groups: alkyl-substituted phenyl group, -F-substituted phenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, carbazoyl group, dibenzofuranyl group, and dibenzothiophenyl group.
[0391] However, the implementation of this disclosure is not limited to this.
[0392] The compound represented by formula 201 can be represented by the following formula 201A:
[0393] Formula 201A
[0394]
[0395] In one embodiment, the compound represented by formula 201 may be represented by the following formula 201A(1), but the embodiments of this disclosure are not limited thereto:
[0396] Formula 201A(1)
[0397]
[0398] In one or more embodiments, the compound represented by formula 201 may be represented by the following formula 201A-1, but the embodiments of this disclosure are not limited thereto:
[0399] Formula 201A-1
[0400]
[0401] In one embodiment, the compound represented by formula 202 can be represented by the following formula 202A:
[0402] Formula 202A
[0403]
[0404] In one or more embodiments, the compound represented by formula 202 can be represented by the following formula 202A-1:
[0405] Formula 202A-1
[0406]
[0407] In Equations 201A, 201A(1), 201A-1, 202A, and 202A-1,
[0408] L 201 To L 203 xa1 to xa3, xa5 and R 202 To R 204 Each can be understood by referring to the corresponding descriptions of Equations 201 and 202 presented in this article.
[0409] R 211 and R 212 You can refer to the information about R. 203 To understand, and
[0410] R 213 To R 217 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 10 Alkyl-substituted phenyl groups, -F-substituted phenyl groups, pentanenyl groups, indole groups, naphthyl groups, chamomile cycloyl groups, heptenyl groups, indoleyl groups, acenaphthyl groups, fluorenyl groups, spiro-difluorenyl groups, benzo[a]fluorenyl groups, dibenzo[a]fluorenyl groups, phenanthrenyl groups, anthraceneyl groups, fluoranthraceneyl groups, benzo[a]phenanthreneyl groups, pyrene groups, The group includes benzo[a], tetraphenyl[b], furan[b], peryl[b], pentaphenyl[a], hexaphenyl[b], pentaphenyl[a], rutin[b], koj[b], ovoid[b], thiophen[b], furan[b], carbazo[b], indole[b], isoindole[b], benzofuran[b], benzothiophen[b], dibenzofuran[b], dibenzothiophen[b], benzocarbazo[b], dibenzocarbazo[b], dibenzothiophen[b], dibenzothiophen[b], and pyridyl[b]
[0411] The hole transport region may contain at least one compound selected from compounds HT1 to HT39, but embodiments of this disclosure are not limited thereto:
[0412]
[0413]
[0414]
[0415] The thickness of the hole transport region can be approximately to approximately For example, about to approximately When the hole transport region includes at least one selected from the hole injection layer and the hole transport layer, the thickness of the hole injection layer can be approximately to approximately For example, about to approximately Furthermore, the thickness of the hole transport layer can be approximately to approximately For example, about to approximately When the thicknesses of the hole transport region, hole injection layer, and hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage.
[0416] The emission assist layer can increase light emission efficiency by compensating for the optical resonant distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block the flow of electrons from the electron transport region. The emission assist layer and the electron blocking layer can contain materials as described above.
[0417] p-dopants
[0418] In addition to these materials, the hole transport region may further contain charge-generating materials to improve conductivity. The charge-generating materials may be uniformly or non-uniformly dispersed within the hole transport region.
[0419] The charge-generating material can be, for example, a p-doped agent.
[0420] In one embodiment, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of -3.5 eV or below -3.5 eV.
[0421] p-dopers may include at least one selected from quinone derivatives, metal oxides, and compounds containing cyano groups, but embodiments of this disclosure are not limited thereto.
[0422] For example, p-dopers may include at least one selected from the following:
[0423] Quinone derivatives (e.g., tetracyanoquinone dimethyl (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl (F4-TCNQ);
[0424] Metal oxides (e.g., tungsten oxide and / or molybdenum oxide);
[0425] 1,4,5,8,9,12-hexaazatriphenylene-hexacarbamate (HAT-CN); and
[0426] Compounds represented by the following formula 221:
[0427] However, the implementation of this disclosure is not limited to this:
[0428]
[0429]
[0430] Equation 221
[0431]
[0432] In Equation 221,
[0433] R 221 To R 223 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, wherein the group is selected from R 221 To R 223 At least one of them may have a C1-C group selected from cyano group, -F, -Cl, -Br, -I, or a C1-C group substituted with -F. 20 Alkyl groups, C1-C substituted with -Cl 20 Alkyl groups, C1-C substituted with -Br 20 Alkyl groups and C1-C substituted with -I 20 At least one substituent in an alkyl group.
[0434] Emission layer in organic layer 150
[0435] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emitting layer can be patterned as a red emitting layer, a green emitting layer, or a blue emitting layer, depending on the sub-pixel. In one or more embodiments, the emitting layer may have a stacked structure of two or more layers selected from red, green, and blue emitting layers, wherein the two or more layers are in contact with or spaced apart from each other. In one or more embodiments, the emitting layer may contain two or more materials selected from red-emitting, green-emitting, and blue-emitting materials, wherein the two or more materials are mixed with each other in a single layer to emit white light.
[0436] The thickness of the emission layer can be approximately to approximately For example, about to approximately When the thickness of the emitting layer is within these ranges, suitable (e.g., excellent) light emission characteristics can be obtained without a significant increase in the driving voltage.
[0437] Electron transport region in organic layer 150
[0438] The electron transport region may have i) a single-layer structure comprising a single layer of a single material, ii) a single-layer structure comprising a single layer of multiple different materials, or iii) a multi-layer structure comprising multiple layers of multiple different materials.
[0439] 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.
[0440] For example, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein for each structure, the constituent layers are stacked sequentially from the emitter layer in a prescribed order. However, the implementation scheme of the electron transport region structure is not limited to this.
[0441] The electron transport region (e.g., a buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may contain a metal-free compound having at least one ring of nitrogen with depleted π electrons.
[0442] The term "a ring containing nitrogen with depleted π electrons" refers to a C1-C ring having at least one *-N=*' moiety as the cyclic part. 60 Heterocyclic groups.
[0443] For example, "a ring containing nitrogen with depleted π electrons" can be i) a 5- to 7-membered heterocyclic group having at least one *-N=*' moiety, ii) a heteropolycyclic group wherein two or more 5- to 7-membered heterocyclic groups each having at least one *-N=*' moiety are fused together, or iii) at least one of the 5- to 7-membered heterocyclic groups each having at least one *-N=*' moiety is combined with at least one C5-C 60 A heterocyclic group with fused carbocyclic groups.
[0444] Examples of nitrogen rings containing π-electron-depleted nitrogen include imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthidine, quinoxaline, quinazoline, cycloline, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole, isobenzothiazole, benzoxazole, isobenzoxazole, triazole, tetraazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole, but embodiments of this disclosure are not limited thereto.
[0445] For example, the electron transport region may contain a compound represented by the following formula 601:
[0446] Formula 601
[0447] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21
[0448] In Equation 601,
[0449] Ar 601 It can be substituted or unsubstituted C5-C 60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups,
[0450] xe11 can be 1, 2, or 3.
[0451] L 601 It can be selected from substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C60 arylene groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.
[0452] xe1 can be an integer from 0 to 5.
[0453] R 601 It can be selected from substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -Si(Q 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q) 601 ) and -P(=O)(Q 601 (Q) 602 ),
[0454] Q 601 To Q 603 Each can be C1-C independently. 10 Alkyl groups, C1-C 10 Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, or naphthyl groups, and
[0455] xe21 can be an integer from 1 to 5.
[0456] In one implementation, xe11 quantity of Ar 601 and the number of R in xe21 601 At least one of them may contain a ring of nitrogen with depleted π electrons.
[0457] In one implementation, Ar in Formula 601 601 You can choose from:
[0458] Phenyl group, naphthyl group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[a]phenanthrene group, pyrene group, Groups, tetraphenyl group, styrene group, perylene group, pentaphenyl group, indene-anthracene group, dibenzofuran group, dibenzothiophene group, carbazole group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthidine group, quinoxaline group, quinazolinoline group, cyclophosphine group, phenanthridine group, acridine group, phenanthrene-rhein group, phenazine group, benzimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetraazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group and azacarbazole group; and
[0459] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q) 31 (Q) 32 (Q) 33 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 At least one substituted phenyl group, naphthyl group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[a]phenanthrene group, pyrene group, Groups, tetraphenyl, styrene, perylene, pentaphenyl, indene-anthracene, dibenzofuran, dibenzothiophene, carbazole, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthidine, quinoxaline, quinazolin, cinnamic acid, phenanthridine, acridine, phenanthrene-rhein, phenazine, benzimidazole, isobenzothiazole, benzoxazole, isobenzoxazole, triazole, tetraazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole, and
[0460] Q 31 To Q 33Each can be independently selected from C1-C 10 Alkyl groups, C1-C 10 Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups.
[0461] When xe11 in equation 601 is 2 or greater than 2, there are two or more Ar... 601 They can be connected to each other via a single key.
[0462] In one or more embodiments, Ar in Formula 601 601 It can be an anthracene group.
[0463] In one or more embodiments, the compound represented by formula 601 can be represented by the following formula 601-1:
[0464] Formula 601-1
[0465]
[0466] In Equation 601-1,
[0467] X 614 It can be N or C(R) 614 ), X 615 It can be N or C(R) 615 ), X 616 It can be N or C(R) 616 ), and selected from X 614 To X 616 At least one of them can be N,
[0468] L 611 To L 613 Each can refer to the information about L. 601 To understand using the provided description,
[0469] xe611 to xe613 can each be understood by referring to the description of xe1 presentation.
[0470] R 611 To R 613 You can refer to the information about R. 601 To understand, and
[0471] R 614 To R 616 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups.
[0472] In one implementation, L in Formula 601 and Formula 601-1 601 and L 611 To L 613 Each can be selected independently from:
[0473] Phenylidene group, naphthyl group, fluorenelidene group, spiro-difluorenelidene group, benzo[a]fluorenelidene group, dibenzo[a]fluorenelidene group, phenanthrenelidene group, anthracenelidene group, fluorenethracene group, benzo[a]phenanthrenelidene group, pyrene group, etc. Perylene group, pentaphenylene group, hexaphenylene group, pentaphenylene group, thiophene group, furanyl group, carbazolyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzothiophene group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiazolyl diazolyl group, oxadiazolyl group , pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolineyl group, isoquinolineyl group, benzoquinolineyl group, phthalazinyl group, naphridinyl group, quinoxalinyl group, quinoxalinyl group, phenanthrene-pyridinyl group, acridineyl group, phenanthrene-pyridinyl group, benzimidazoleyl group, isobenzothiazolyl group, benzimidazoleyl group, isobenzoxazoleyl group, isobenzoxazoleyl group, triazoleyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and zazacarbazolyl group; and
[0474] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group, triphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthrene group, anthracene group, fluoranthracene group, benzo[a]phenanthrene group, pyrene group, Peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, thiophene group, furanyl group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, pyridyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinoline At least one substituted phenylene group, naphthidyl group, quinoxalinyl group, quinazolinyl group, phenanthrynyl group, acridineyl group, phenanthrolineyl group, phenazinyl group, benzimidazole group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazole group, tetrazolyl group, imidazopyridyl group, imidazopyrimidyl group, and azacarbazolyl group, naphthylene group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenanthrene group, anthracene group, fluorenyl anthracene group, benzo[a]phenanthrene group, pyrene group, etc., selected from the following groups: phenylene group, naphthylene group, naphthylene group, benzo[a]phenanthrene group, pyrene group, etc. Perylene group, pentaphenylene group, hexaphenylene group, pentaphenylene group, thiophene group, furanyl group, carbazolyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzothiophene group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiazolyl diazolyl group, oxadiazolyl group The following groups are listed: pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolineyl group, isoquinolineyl group, benzo[a]quinolineyl group, phthalazinyl group, naphthidyl group, quinoxalinyl group, quinoxalinyl group, phenanthrene-pyridinyl group, acridineyl group, phenanthrene-pyridinyl group, benzimidazoleyl group, isobenzothiazolyl group, benzimidazoleyl group, isobenzoxazoleyl group, isobenzoxazoleyl group, triazoleyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and zazacarbazolyl group.
[0475] However, the implementation of this disclosure is not limited to this.
[0476] In one or more embodiments, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 can each be 0, 1 or 2 independently.
[0477] In one or more embodiments, R in Formula 601 and Formula 601-1 601 and R 611 To R 613 Each can be selected independently from:
[0478] Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthryl group, anthraceneyl group, fluoranthraceneyl group, benzo[a]phenanthryl group, pyrene group, Peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, thiophene group, furanyl group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, pyridinyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group Groups, including pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphridinyl group, quinoxalinyl group, quinazolinyl group, cyclophosphinyl group, phenanthridineyl group, acridineyl group, phenanthroxolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and azacarbazolyl group;
[0479] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group, triphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthrene group, anthracene group, fluoranthracene group, benzo[a]phenanthrene group, pyrene group, Peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, thiophene group, furanyl group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, pyridyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinoline The following groups are substituted with at least one of the following groups: phthalazinyl group, naphthidyl group, quinoxalinyl group, quinazolinyl group, phenanthrynyl group, acridineyl group, phenanthrolineyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridyl group, imidazopyrimidyl group, and azacarbazolyl group; a substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[fluorenyl]fluorenyl group, dibenzo[fluorenyl]fluorenyl group, phenanthrene group, anthraceneyl group, fluoranthraceneyl group, benzo[phenanthreneyl]pyrene group. Peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, thiophene group, furanyl group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, pyridyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group Pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphridinyl group, quinoxalinyl group, quinazolinyl group, cyclophosphinyl group, phenanthridineyl group, acridineyl group, phenanthroxolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and azacarbazolyl group; and
[0480] -S(=O)2(Q 601 ) and -P(=O)(Q 601 (Q) 602 ),
[0481] Q 601 and Q 602 Same as described above.
[0482] The electron transport region may contain at least one compound selected from compounds ET1 to ET36, but embodiments of this disclosure are not limited thereto:
[0483]
[0484]
[0485]
[0486]
[0487] In one or more embodiments, the electron transport region may comprise at least one compound selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, 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):
[0488]
[0489]
[0490] The thickness of the buffer layer, hole blocking layer, or electronic control layer can be approximately to approximately For example, about to approximately When the thicknesses of the buffer layer, hole blocking layer, and electronic control layer are within these ranges, the hole blocking layer or electronic control layer can have suitable (e.g., excellent) hole blocking characteristics or electronic control characteristics without a significant increase in driving voltage.
[0491] The thickness of the electron transport layer can be approximately to approximately For example, about to approximately When the thickness of the electron transport layer is within the range described above, the electron transport layer can have satisfactory electron transport characteristics without a significant increase in driving voltage.
[0492] In addition to the materials described above, the electron transport region (e.g., the electron transport layer in the electron transport region) may further contain a metallic material.
[0493] The metal-containing material may include at least one selected from alkali metal complexes and alkaline earth metal complexes. Alkali metal complexes may contain metal ions selected from Li, Na, K, Rb, and Cs ions, and alkaline earth metal complexes may contain metal ions selected from Be, Mg, Ca, Sr, and Ba ions. The ligand coordinating with the metal ion of the alkali metal or alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, and cyclopentadiene, but embodiments of this disclosure are not limited thereto.
[0494] For example, metal-containing materials may include Li complexes. Li complexes may include, for example, the following compounds: ET-D1 (lithium hydroxyquinoline, LiQ) or ET-D2:
[0495]
[0496] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.
[0497] The electron injection layer can have i) a single-layer structure comprising a single layer containing a single material, ii) a single-layer structure comprising a single layer containing multiple different materials, or iii) a multi-layer structure comprising multiple layers containing multiple different materials.
[0498] The electron injection layer may contain alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof.
[0499] The alkali metal can be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal can be Li, Na, and / or Cs. In one or more embodiments, the alkali metal can be Li and / or Cs, but the embodiments of this disclosure are not limited thereto.
[0500] Alkaline earth metals can be selected from Mg, Ca, Sr and Ba.
[0501] Rare earth metals can be selected from Sc, Y, Ce, Tb, Yb and Gd.
[0502] Alkali metal compounds, alkaline earth metal compounds, and rare earth metal compounds may be selected from oxides and halides of alkali metals, alkaline earth metals, and rare earth metals (e.g., fluorides, chlorides, bromides, or iodides).
[0503] The alkali metal compound can be selected from alkali metal oxides (such as Li2O, Cs2O, and / or K2O) 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, Li2O, NaF, LiI, NaI, CsI, and KI, but the embodiments of the present disclosure are not limited thereto.
[0504] 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.
[0505] The rare earth metal compound can be selected from YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, and TbF3. In one embodiment, the rare earth metal compound can be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but the embodiments of the present disclosure are not limited thereto.
[0506] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex can contain ions of alkali metals, alkaline earth metals, and rare earth metals 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.
[0507] The electron injection layer can contain (for example, be composed of) the following: alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof as described above. In one or more embodiments, the electron injection layer can further contain an organic material. When the electron injection layer further contains an organic material, the alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof can be uniformly or non-uniformly dispersed in the matrix containing the organic material.
[0508] The thickness of the electron injection layer can be about to approximately For example, about to approximately When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics can be obtained without a significant increase in the driving voltage.
[0509] Second electrode 190
[0510] The second electrode 190 is located on the organic layer 150 having such a structure. The second electrode 190 can be a cathode serving as an electron injection electrode, and in this respect, the material used to form the second electrode 190 can be selected from metals, alloys, conductive compounds, and combinations thereof that can have relatively low work function.
[0511] The second electrode 190 may contain 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 embodiments of this disclosure are not limited thereto. The second electrode 190 may be a transmission electrode, a semi-transmission electrode, or a reflection electrode.
[0512] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.
[0513] Figures 2 to 4 Description
[0514] Figure 2 The organic light-emitting device 20 has a structure in which a first cover layer 210, a first electrode 110, an organic layer 150 and a second electrode 190 are stacked in a predetermined order; Figure 3 The organic light-emitting device 30 has a structure in which a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 are stacked sequentially in a predetermined order; and Figure 4 The organic light-emitting device 40 has a structure in which a first cover layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second cover layer 220 are stacked in a predetermined order.
[0515] about Figures 2 to 4 You can refer to the information about Figure 1 The corresponding descriptions are provided to understand the first electrode 110, the organic layer 150, and the second electrode 190.
[0516] In the organic layer 150 of each of the organic light-emitting devices 20 and 40, light generated in the emitting layer can pass outward through the first electrode 110 and the first capping layer 210, wherein the first electrode 110 can be a semi-transparent 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 emitting layer can pass outward through the second electrode 190 and the second capping layer 220, wherein the second electrode 190 can be a semi-transparent electrode or a transmissive electrode.
[0517] The first capping layer 210 and the second capping layer 220 can increase the external luminous efficiency according to the principle of constructive interference.
[0518] The first covering layer 210 and the second covering layer 220 can each independently be an organic covering layer containing organic materials, an inorganic covering layer containing inorganic materials, or a composite covering layer containing both organic and inorganic materials.
[0519] At least one of the first capping layer 210 and the second capping layer 220 may each independently comprise at least one material selected from carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphyrin derivatives, phthalocyanine derivatives, naphthylphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds, and amine-based compounds may optionally be substituted with substituents containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one of the first capping layer 210 and the second capping layer 220 may each independently comprise an amine-based compound.
[0520] In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently contain a compound represented by formula 201 or a compound represented by formula 202.
[0521] In one or more embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently contain a compound selected from compounds HT28 to HT33 and the following compounds CP1 to CP5, but the embodiments of this disclosure are not limited thereto.
[0522]
[0523] In the above text, we have already discussed... Figures 1 to 4 An organic light-emitting device according to an embodiment is described, but the embodiments of this disclosure are not limited thereto.
[0524] Layers constituting hole transport regions, emission regions, and electron transport regions can be formed in a specific region using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.
[0525] When forming layers constituting hole transport regions, emitter regions, and electron transport regions via vacuum deposition, by considering the materials to be included in the layers to be formed and the structure of the layers to be formed, deposition temperatures of approximately 100°C to approximately 500°C and approximately 10 -8 To about 10 -3 The vacuum degree and about to approximately Deposition occurs at a certain deposition rate.
[0526] When spin coating is used to form layers constituting hole transport regions, emission regions, and electron transport regions, spin coating can be performed at a coating rate of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80°C to about 200°C, taking into account the materials to be included in the layers to be formed and the structure of the layers to be formed.
[0527] equipment
[0528] Organic light-emitting devices can be included in a variety of suitable equipment.
[0529] More specifically, an example of such a device may include: a thin-film transistor comprising a source electrode, a drain electrode, and an active layer; and an organic light-emitting device. Here, the first electrode of the organic light-emitting device may be in electrical contact with the source electrode or the drain electrode of the thin-film transistor.
[0530] Thin-film transistors may further include gate electrodes, gate insulating layers, etc.
[0531] The active layer may include crystalline silicon, amorphous silicon, organic semiconductors, oxide semiconductors, etc., but the embodiments disclosed herein are not limited to these.
[0532] The device may further include a sealing component for sealing the organic light-emitting device. The sealing component allows the display of images from the organic light-emitting device and prevents external air and moisture from penetrating into the device. The sealing component may be a sealing substrate comprising a transparent glass or plastic substrate. The sealing component may be a thin-film encapsulation layer comprising multiple organic layers and / or multiple inorganic layers. When the sealing component is a thin-film encapsulation layer, the entire device can be flexible.
[0533] For example, the device can be a light-emitting device, a verification device, or an electronic device.
[0534] Light-emitting devices can be used as various suitable displays, light sources, etc.
[0535] The verification device can be, for example, a biometric verification device for verifying an individual using biometric information from a biometric body (e.g., fingertip, pupil, etc.). In addition to an organic light-emitting device, the verification device may further include a biometric information collector.
[0536] Electronic devices can be applied to personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, video game consoles, medical instruments (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram (ECG) displays, ultrasound diagnostic devices, or endoscopic displays), fish finders, various suitable measuring instruments, meters (e.g., instruments for vehicles, aircraft, and ships), projectors, etc., but embodiments of this disclosure are not limited thereto.
[0537] [General definition of substituents]
[0538] As used herein, the term "cyclic group containing π-electron-depleted nitrogen" refers to a cyclic group having at least one *-N=*' moiety, and non-limiting examples include imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyridazine, pyrimidine, indazole, purine, quinoline, isoquinoline, benzo[a]quinoline, phthalazine, naphthidine, quinoxaline, quinazoline, cinnamic acid, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole, isobenzothiazole, benzo[a]oxazole, isobenzo[a]oxazole, triazole, tetraazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole.
[0539] Cyclic groups that do not contain nitrogen with depleted π electrons can be selected from phenyl groups, heptalene groups, indene groups, naphthyl groups, chamomile ring groups, indole groups, acenaphthene groups, fluorene groups, spiro-difluorene groups, benzo[a]fluorene groups, dibenzo[a]fluorene groups, phenanthracene groups, anthracene groups, fluoranthracene groups, benzo[a]phenanthrene groups, pyrene groups, etc. Groups, including tetraphenyl, styrene, perylene, pentaphenyl, hexaphenyl, rubidium, argentinium, oleophyllium, pyrrole, isoindole, indole, furan, thiophene, benzofuran, benzothiophene, benzocarbazole, dibenzocarbazole, dibenzofuran, dibenzothiophene, dibenzothiophene sulfone, carbazole, dibenzothiophene, indole, indo-carbazole, benzofuran-carbazole, benzothiophene-carbazole, and triindo-phenyl, but embodiments of this disclosure are not limited thereto.
[0540] As used herein, the term "transition metal of period 4" refers to an element in period 4 of the periodic table and in the d-block, and non-limiting examples include scandium (Sc), titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), and zinc (Zn).
[0541] As used herein, the term "transition metal of period 5" refers to an element in period 5 of the periodic table and in the d-block, and non-limiting examples include yttrium (Y), zirconium (Zr), niobium (Nb), molybdenum (Mo), technetium (Tc), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), and cadmium (Cd).
[0542] As used herein, the term "transition metal of period 6" refers to elements in period 6 of the periodic table, in both the d and f blocks, and non-limiting examples 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).
[0543] As used in this article, the term "C1-C" 60 "alkyl group" refers to a straight-chain or branched monovalent aliphatic saturated hydrocarbon group having 1 to 60 carbon atoms, and non-limiting examples include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl groups. In some embodiments, C1-C 60 Alkyl groups can be C1-C 30 Alkyl groups, C1-C 20 alkyl groups or C1-C 10 Alkyl groups. As used in this document, "C1-C..." 60 "alkylene group" refers to a group that has a C1-C2 bond structure. 60 Alkyl groups are divalent groups with the same structure.
[0544] As used in this article, the term "C2-C" 60 "Alkenyl group" refers to the group located at C2-C. 60 The alkyl group has at least one carbon-carbon double bond at its middle or end, and non-limiting examples include vinyl groups, propenyl groups, and butenyl groups. In some embodiments, C2-C 60 The alkenyl group can be C2-C 30 alkenyl groups, C2-C 20 alkenyl groups or C2-C 10 Alkenyl group. As used in this article, "C2-C" 60 "Ideinyl group" refers to a group that has a C2-C... 60 Divalent groups with the same structure as alkenyl groups.
[0545] As used in this article, the term "C2-C" 60 "Alkyne group" refers to the group located at C2-C. 60 The alkyl group is a hydrocarbon group having at least one carbon-carbon triple bond at its middle or end, and non-limiting examples include ethynyl and propynyl groups. In some embodiments, C2-C 60 The alkynyl group can be C2-C 30 alkynyl group, C2-C 20 alkynyl group or C2-C 10 Alkynyl group. As used in this article, "C2-C" 60 "Imyynyl group" refers to a group that has a C2-C... 60 Divalent groups with the same structure as alkynyl groups.
[0546] As used in this article, the term "C1-C" 60 "Alkoxy group" refers to the group consisting of -OA 101 (where A) 101 For C1-C 60 The alkyl group is a monovalent group, and non-limiting examples of it include methoxy groups, ethoxy groups and isopropoxy groups.
[0547] As used in this article, the term "C3-C" 10 "Cycloalkyl group" refers to a monocyclic saturated hydrocarbon group having 3 to 10 carbon atoms, and non-limiting examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl groups. As used herein, the term "C3-C" is also relevant. 10 "Cycloalkylene group" refers to a group that has a C3-C6 bond structure. 10 A divalent group with the same structure as a cycloalkyl group.
[0548] As used in this article, the term "C1-C" 10"Heterocyclic alkyl group" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S (e.g., 1 to 5 or 1 to 3 heteroatoms, such as 1, 2, 3, 4, or 5 heteroatoms) as a cyclic atom in addition to 1 to 10 carbon atoms, and non-limiting examples include 1,2,3,4-oxatriazole alkyl groups, tetrahydrofuranyl groups, and tetrahydrothiophenyl groups. The term "C1-C" as used herein is also relevant. 10 "Heterocyclic alkyl groups" refers to groups with C1-C2 groups. 10 Divalent groups with the same structure as heterocyclic alkyl groups.
[0549] As used in this article, the term "C3-C" 10 "Cycloalkenyl group" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and lacking aromaticity, and non-limiting examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl groups. As used herein, the term "C3-C" is also relevant. 10 "Iridyl group" refers to a group that has a C3-C6 bond structure. 10 A divalent group with the same structure as the cycloalkenyl group.
[0550] As used in this article, the term "C1-C" 10 A "heterocyclic alkenyl group" refers to a monovalent monocyclic group having at least one heteroatom (e.g., 1 to 5 or 1 to 3 heteroatoms, such as 1, 2, 3, 4 or 5 heteroatoms) selected from N, O, Si, P and S as cyclic atoms, 1 to 10 carbon atoms, and at least one double bond in its ring. C1-C 10 Non-limiting examples of heterocyclic alkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl groups. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl group" refers to a group that has a C1-C2 bond structure. 10 Divalent groups with the same structure as heterocyclic alkenyl groups.
[0551] As used in this article, the term "C6-C" 60 "Aryl group" refers to a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms, and as used herein, "C6-C..." 60 "Aromatic group" refers to a divalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms. In some embodiments, C6-C 60 The aryl group can be C6-C. 30 aryl group, C6-C 24 aryl group or C6-C 18 Aryl group. C6-C 60Non-limiting examples of aryl groups include phenyl groups, naphthyl groups, anthracene groups, phenanthrene groups, pyrene groups, and... Basic group. When C6-C 60 aryl groups and C6-C 60 When each of the aryl groups comprises two or more rings, the rings may be fused together.
[0552] As used in this article, the term "C1-C" 60 A "heteroaryl group" refers to a monovalent group in a carbocyclic aromatic system having at least one heteroatom selected from N, O, Si, P, and S (e.g., 1 to 5 or 1 to 3 heteroatoms, such as 1, 2, 3, 4, or 5 heteroatoms) as a cyclic atom in addition to 1 to 60 carbon atoms. The term "C1-C" is used herein. 60 A "hybrid aryl group" refers to a divalent group in a carbocyclic aromatic system having at least one heteroatom (e.g., 1 to 5 or 1 to 3 heteroatoms, such as 1, 2, 3, 4, or 5 heteroatoms) selected from N, O, Si, P, and S as cyclic atoms in addition to 1 to 60 carbon atoms. C1-C 60 Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl groups. In some embodiments, C1-C 60 The heteroaryl group can be C1-C 30 heteroaryl groups, C1-C 24 heteroaryl groups or C1-C 18 heteroaryl groups. When C1-C 60 heteroaryl groups and C1-C 60 When each of the heteroaryl groups comprises two or more rings, the rings can be fused together.
[0553] As used in this article, the term "C6-C" 60 "Aryloxy group" refers to -OA 102 (where A) 102 For C6-C 60 (aryl group), and as used herein by the term "C6-C" 60 "Aryl thio group" refers to -SA 103 (where A) 103 For C6-C 60 (aryl group).
[0554] As used in this article, the term "C1-C" 60 "Heteroaryloxy group" refers to the group composed of -OA 104 (where A) 104 For C1-C 60 Monovalent groups (represented by heteroaryl groups), and as used herein by the term "C1-C"60 "Heteroary sulfide group" refers to -SA 105 (where A) 105 For C1-C 60 (Heteroaryl groups).
[0555] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group (e.g., having 8 to 60 carbon atoms, such as 8 to 30 or 8 to 24 carbon atoms) having two or more rings fused together, having only carbon atoms as cyclic atoms, and lacking aromaticity throughout its molecular structure. A non-limiting example of a monovalent nonaromatic fused polycyclic group is the fluorene group. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused polycyclic group.
[0556] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group (e.g., having 1 to 60 carbon atoms, such as 1 to 30 or 1 to 24 carbon atoms) having two or more rings fused together, at least one heteroatom selected from N, O, Si, P, and S (e.g., 1 to 5 or 1 to 3 heteroatoms, such as 1, 2, 3, 4, or 5 heteroatoms) as a cyclic atom in addition to carbon atoms, and lacking aromaticity throughout its molecular structure. A non-limiting example of a monovalent nonaromatic fused heterocyclic group is the carbazoyl group. As used herein, the term "divalent nonaromatic fused heterocyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused heterocyclic group.
[0557] As used in this article, the term "C5-C" 60 A "carbocyclic group" refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms, where the cyclic atom is only a carbon atom. For example, the term "C5-C" as used herein... 60 "Carbocyclic group" refers to either an aromatic carbocyclic group or a non-aromatic carbocyclic group. C5-C 60 The carbocyclic group can be a ring (e.g., benzene), a monovalent group (e.g., a phenyl group), or a divalent group (e.g., a phenylene group). In one or more embodiments, according to the linkage to C5-C... 60 The number of substituents in the carbocyclic group, C5-C 60 The carbocyclic group can be trivalent or tetravalent. In some embodiments, C5-C 60 The carbocyclic group can be C5-C. 30 Carbocyclic groups, C5-C 24 Carbocyclic groups or C5-C 18 Carbocyclic group. In some other embodiments, C5-C 30 The carbocyclic group can be C5-C.24 Carbocyclic groups, C5-C 18 Carbocyclic groups or C5-C 12 Carbon ring group.
[0558] As used in this article, the term "C1-C" 60 "Heterocyclic group" refers to a group that has a cyclic structure similar to C5-C6. 60 A group with the same structure as the carbocyclic group, but using at least one heteroatom selected from N, O, Si, P, and S (e.g., 1 to 5 or 1 to 3 heteroatoms, e.g., 1, 2, 3, 4, or 5 heteroatoms) as the cyclic atom in addition to carbon (the number of carbon atoms can be 1 to 60, for example 1 to 30 or 1, 2, 3, 4, or 5 heteroatoms). In some embodiments, C1-C 30 Heterocyclic groups can be C1-C 24 Heterocyclic groups, C1-C 18 Heterocyclic groups or C1-C 12 Heterocyclic groups.
[0559] In this specification, C5-C is replaced. 30 Carbocyclic groups, substituted C5-C 60 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Heterocyclic groups, substituted C3-C 10 Cycloalkyl groups, substituted C1-C 10 Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkylene groups, substituted C1-C 10 Heterocyclic alkenyl groups, substituted C6-C 60 arylene groups, substituted C1-C 60 Heteroaryl groups, substituted divalent nonaromatic fused polycyclic groups, substituted divalent nonaromatic fused heterocyclic groups, substituted C1-C 60 Alkyl groups, substituted C2-C 60 alkenyl groups, substituted C2-C 60 alkynyl group, substituted C1-C 60 alkoxy groups, substituted C3-C 10 Cycloalkyl groups, substituted C1-C 10 Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkenyl groups, substituted C1-C 10 Heterocyclic alkenyl groups, substituted C6-C 60 aryl group, substituted C6-C 60 aryloxy groups, substituted C6-C 60 aryl thiols, substituted C1-C 60 heteroaryl groups, substituted C1-C60 Heteroaryl groups, substituted C1-C 60 At least one substituent of the heteroaryl thio group, the substituted monovalent nonaromatic fused polycyclic group, and the substituted monovalent nonaromatic fused heterocyclic group may be selected from:
[0560] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl groups and C1-C 60 alkoxy group;
[0561] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiols, C1-C 60 heteroaryl groups, C1-C 60 heteroaryloxy groups, C1-C 60 Heteroaryl thioyl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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 At least one substituted C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl groups and C1-C 60 alkoxy group;
[0562] C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiols, C1-C 60 heteroaryl groups, C1-C 60 heteroaryloxy groups, C1-C 60 Heteroaryl thio groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups;
[0563] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiols, C1-C 60 heteroaryl groups, C1-C 60 heteroaryloxy groups, C1-C 60 Heteroaryl thioyl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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 At least one substituted C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiols, C1-C60 heteroaryl groups, C1-C 60 heteroaryloxy groups, C1-C 60 Heteroaryl thio groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups; and
[0564] -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 ),
[0565] Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 Aryl group, C1-C 60 heteroaryl groups, C1-C 60 Heteroaryloxy group, C1-C 60 A heteroaryl thioyl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heterocyclic group, a C1-C group substituted with at least one of deuterium, -F and cyano groups. 60 The alkyl group is a C6-C group substituted with at least one of a deuterium, -F, or cyano group. 60 Aryl groups, biphenyl groups, and terphenyl groups.
[0566] As used herein, the term "Ph" refers to a phenyl group, "Me" refers to a methyl group, "Et" refers to an ethyl group, and "tert-Bu" or "Bu" refers to a tert-Bu group. t "" refers to the tert-butyl group, and as used herein, the term "OMe" refers to the methyl methacrylate group.
[0567] As used in this article, the term "biphenyl group" refers to a "phenyl group substituted with a phenyl group." In other words, a "biphenyl group" is a group with a C6-C6 bond. 60 The aryl group is a substituted phenyl group.
[0568] As used in this article, the term "terphenyl group" refers to a "phenyl group substituted with a biphenyl group." In other words, a "terphenyl group" is a phenyl group with a C6-C substituted group. 60 C6-C substituted with aryl group 60 The aryl group is a substituted phenyl group.
[0569] As used herein, unless otherwise defined, * and *' each refer to the binding site with the adjacent atom in the corresponding formula.
[0570] The compounds and organic light-emitting devices according to the embodiments will be described in more detail below with reference to the examples.
[0571] Example
[0572] Example 1-1
[0573] As the anode, the indium tin oxide (ITO) deposited substrate was cut to a size of 50 mm × 50 mm × 0.5 mm and ultrasonically treated with isopropanol and pure water for 5 minutes each, followed by cleaning with ultraviolet irradiation for 30 minutes and exposure to ozone. The resulting ITO substrate was then mounted on a vacuum deposition apparatus.
[0574] Depositing m-MTDATA on an ITO substrate to form a structure with A hole injection layer of a certain thickness is formed, followed by vacuum deposition of NPB on the hole injection layer to form a layer with [missing information]. A hole transport layer of a certain thickness was formed, and compounds HT-01, ET-1, 1, and D-07 were co-deposited on the hole transport layer in a weight ratio of 30:70:15:1 to form a hole transport layer with a thickness of [missing information]. A thick emission layer. Compound BFO3 is deposited on the emission layer to form a layer with... A hole-blocking layer of thickness. Compound ET1 is deposited on the hole-blocking layer to form a layer with... An electron transport layer of a certain thickness is formed. Al is deposited on the electron transport layer to form an electron transport layer with... A cathode of a certain thickness is used to complete the fabrication of an organic light-emitting device.
[0575] Examples 1-2 to 1-5 and Comparative Examples 1-1 to 1-15
[0576] The organic light-emitting device was manufactured in the same manner as in Examples 1-1, but the emission layer and hole blocking layer were formed using the compounds shown in Table 1, respectively.
[0577] Evaluation Example 1
[0578] Using a Keithley SMU 236 and a PR650 luminance meter at 10 mA / cm 2 The current density was measured for 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 1-15. The results are shown in Table 1. Lifetime is a measure of the time it takes for the brightness to decrease from its initial brightness to 90% of its initial brightness.
[0579] [Table 1]
[0580]
[0581]
[0582] Table 1 shows that the organic light-emitting devices of Examples 1-1 to 1-5 have higher current efficiency and longer service life compared with the organic light-emitting devices of Comparative Examples 1-1 to 1-15.
[0583] Example 2-1
[0584] As the anode, the indium tin oxide (ITO) deposited substrate was cut to a size of 50 mm × 50 mm × 0.5 mm and ultrasonically treated with isopropanol and pure water for 5 minutes each, followed by cleaning with ultraviolet irradiation for 30 minutes and exposure to ozone. The resulting ITO substrate was then mounted on a vacuum deposition apparatus.
[0585] Depositing m-MTDATA on an ITO substrate to form a structure with A hole injection layer of a certain thickness is formed, followed by vacuum deposition of NPB on the hole injection layer to form a layer with [missing information]. A hole transport layer of a certain thickness was formed, and compounds HT-01, ET-4, PT1, and D-01 were co-deposited on the hole transport layer in a weight ratio of 30:70:15:1 to form a hole transport layer with a thickness of 1000 mm. An emission layer of a certain thickness. Compound BF01 is deposited on the emission layer to form a layer with... A hole-blocking layer of thickness. Compound ET1 is deposited on the hole-blocking layer to form a layer with... An electron transport layer of a certain thickness is formed. Al is deposited on the electron transport layer to form an electron transport layer with... A cathode of a certain thickness is used to complete the fabrication of an organic light-emitting device.
[0586] Examples 2-2 to 2-5 and Comparative Examples 2-1 to 2-15
[0587] The organic light-emitting device was manufactured in the same manner as in Example 2-1, but the emission layer and hole blocking layer were formed using the compounds shown in Table 2, respectively.
[0588] Evaluation Example 2
[0589] Using Keithley SMU 236 and PR650 luminance meter at 10mA / cm 2 The current density was measured for 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 2-15. The results are shown in Table 2. Lifetime is a measure of the time it takes for the brightness to decrease from its initial brightness to 90% of its initial brightness.
[0590] [Table 2]
[0591]
[0592]
[0593] Table 2 shows that the organic light-emitting devices of Examples 2-1 to 2-5 have higher current efficiency and longer service life compared with the organic light-emitting devices of Comparative Examples 2-1 to 2-15.
[0594] As described above, the organic light-emitting device according to the embodiments of this disclosure can have high efficiency and long service life.
[0595] The terminology used herein is for the purpose of describing specific exemplary embodiments only and is not intended to limit the invention.
[0596] As used herein, the terms “substantially,” “about,” and similar terms are used as terms of approximation rather than terms of degree, and are intended to account for inherent biases in measured or calculated values that would be recognized by one of ordinary skill in the art. Furthermore, any numerical ranges listed herein are intended to include all subranges of the same numerical precision falling within the listed range. For example, the range “1.0 to 10.0” is intended to include all subranges between the listed minimum value of 1.0 and the listed maximum value of 10.0 (and inclusive), i.e., a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit listed herein is intended to include all lower numerical limits falling within it, and any minimum numerical limit listed in this specification is intended to include all higher numerical limits falling within it. Therefore, the applicant reserves the right to amend this specification (including the claims) to expressly list any subranges falling within the scope expressly listed herein.
[0597] When describing embodiments of the inventive concept, the word "may" means "one or more embodiments of the inventive concept".
[0598] It should be understood that the embodiments described herein are for descriptive purposes only and not for limiting purposes. The description of features or aspects in each embodiment should generally be considered applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, those skilled in the art will understand that various changes in form and detail may be made herein without departing from the spirit and scope defined by the claims and their equivalents.
Claims
1. An organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, wherein: the organic layer comprises an emission layer, the emission layer comprises 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 2A or Formula 2B; the third compound is represented by Formula 3; the fourth compound is represented by Formula 4; and the first compound, the second compound, the third compound, and the fourth compound are different from each other: <Formula 1> <Formula 3> <Formula 4> M 31 (L 31 ) n31 (L 32 ) n32 wherein, in Formula 1, a cyclic group not containing a nitrogen of a p-electron depletion, -C(Q1)(Q2)-, -Si(Q1)(Q2)-, -B(Q1)-, and -N(Q1)-; and X 11 selected from O, S, N(R 19 ) and C(R 19 )(R 20 ), R 11 to R 20 are each independently selected from the group consisting of: Depend on -(L 11 ) a11 -A 11 The indicated groups are hydrogen, deuterium, and C1-C. 60 Alkyl groups, cyclic groups without nitrogen that has been depleted of π electrons, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2) and -N(Q1)(Q2); substituted with at least one member selected from the group consisting of deuterium, C1-C 60 alkyl group, a cyclic group not containing a 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 substituted with at least one substituent selected from the group consisting of deuterium, C1-C 60 alkyl groups, cyclic groups free of 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 ) groups free of π-electron depleted nitrogen, L 11 selected from the group consisting of: a11 is selected from 1, 2, and 3, and substituted with at least one member selected from the group consisting of deuterium, C1-C 60 alkyl group, a cyclic group not containing a 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 ) not containing a π-electron depleted nitrogen, a cyclic group not containing a nitrogen of a p-electron depletion; A 11 selected from the group consisting of wherein, in Formula 2A and Formula 2B, substituted with at least one member selected from the group consisting of deuterium, C1-C 60 alkyl group, a cyclic group not containing a 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 substituted with at least one substituent selected from the group consisting of deuterium, C1-C 60 alkyl groups, cyclic groups free of π-electron-withdrawing 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 ) groups, k21 and k22 are each independently selected from 0, 1, 2, 3, and 4, wherein the sum of k21 and k22 is 1 or more than 1, X 21 selected from O, S, N(R 24 ) and C(R 24 )(R 25 ), k23 is selected from 1, 2, 3, 4, 5, and 6, a cyclic group containing a nitrogen of a p-electron depletion, a cyclic group not containing a nitrogen of a p-electron depletion, -C(Q1)(Q2)-, -Si(Q1)(Q2)-, -B(Q1)-, -N(Q1)-, -S(=O)-, -S(=O)2-, -P(=O)(Q1)-, and -P(=S)(Q1)-; and R 21 to R 25 are each independently selected from the group consisting of: Depend on -(L 21 ) a21 -A 21 The groups represented are hydrogen, deuterium, -F, cyano groups, and C1-C. 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2); Each is selected from deuterium, -F, cyano group, C1-C 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q) 31 (Q) 32 (Q) 33 ), -Si(Q 31 (Q) 32 (Q) 33 -B(Q) 31 (Q) 32 -N(Q) 31 (Q) 32 -S(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) and -P(=S)(Q 31 (Q) 32 At least one substituted cyclic group containing π-electron-depleted nitrogen and a cyclic group not containing π-electron-depleted nitrogen; and each independently selected from the group consisting of deuterium, -F, a cyano group, a C1-C4alkyl group, a C1-C4haloalkyl group, a C1-C4hydroxyalkyl group, a C1-C4alkoxyl group, a C1-C4alkylamino group, a C1-C4dialkylamino group, a C3-C6cycloalkyl group, a C2-C4alkenyl group, a C2-C4alkynyl group, a C1-C4alkylsilyl group, a C1-C4alkylgermyl group, a C1-C4alkylstibyl group, a C1-C4alkylarsyl group, a C1-C4alkylphosphinyl group, a C1-C4alkylphosphoryl group, a C1-C4alkylsulfenyl group, a C1-C4alkylsulfinyl group, a C1-C4alkylsulfanyl group, a C1-C4alkylsulfonamide group, a C1-C4alkylsulfone group, a C1-C4alkylcarbonyl group, a C1-C4alkoxycarbonyl group, a C1-C4alkylcarbonyloxy group, a C1-C4alkylcarbonylamino group, a C1-C4alkylaminocarbonyl group, a C1-C4alkylcarbonyloxyimino group, a C1-C4alkylcarbonylazo group, a C1-C4alkylcarbonylhydrazine group, a C1-C4alkylcarbonylhydrazine 60 group, a cyclic group containing a π-electron depleted nitrogen, a cyclic group not containing a π-electron depleted nitrogen, -C(Q 21 )(Q 22 )(Q 23 ), -Si(Q 21 )(Q 22 )(Q 23 ), -B(Q 21 )(Q 22 ), -N(Q 21 )(Q 22 ), -S(=O)(Q 21 ), -S(=O)2(Q 21 ), -P(=O)(Q 21 )(Q 22 ), and -P(=S)(Q 21 )(Q 22 ), L 21 selected from the group consisting of: a21 is selected from 1, 2, and 3, and Each is selected from deuterium, -F, cyano group, C1-C 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q) 31 (Q) 32 (Q) 33 ), -Si(Q 31 (Q) 32 (Q) 33 -B(Q) 31 (Q) 32 -N(Q) 31 (Q) 32 -S(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) and -P(=S)(Q 31 (Q) 32 At least one substituted cyclic group containing π-electron-depleted nitrogen and a cyclic group not containing π-electron-depleted nitrogen in the group. a cyclic group containing a nitrogen of a p-electron depletion and a cyclic group not containing a nitrogen of a p-electron depletion; A 21 selected from the group consisting of wherein, in Formula 3, Each is selected from deuterium, -F, cyano group, C1-C 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q) 31 (Q) 32 (Q) 33 ), -Si(Q 31 (Q) 32 (Q) 33 -B(Q) 31 (Q) 32 -N(Q) 31 (Q) 32 -S(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) and -P(=S)(Q 31 (Q) 32 At least one substituted cyclic group containing π-electron-depleted nitrogen and a cyclic group not containing π-electron-depleted nitrogen; and Each is selected independently from deuterium, -F, cyano groups, C1-C 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q) 21 (Q) 22 (Q) 23 ), -Si(Q 21 (Q) 22 (Q) 23 -B(Q) 21 (Q) 22 -N(Q) 21 (Q) 22 -S(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) and -P(=S)(Q 21 (Q) 22 At least one substituted cyclic group containing π-electron-depleted nitrogen and at least one substituted cyclic group not containing π-electron-depleted nitrogen in the cyclic group of ) n31 is 1 or 2, and M 31 transition metals selected from the 4th period, the 5th period and the 6th period of the periodic table of elements, L 31 is a ligand represented by one selected from Formula 3A to Formula 3D, L 32 selected from monodentate ligands, bidentate ligands and tridentate ligands, n32 is selected from 0, 1, 2, 3, and 4, wherein, in Formula 3A to Formula 3D, k31 to k34 are each independently selected from 1, 2, and 3, A 31 to A 34 each independently selected from C5-C 30 carbocyclic groups and C1-C 30 heterocyclic groups, T 31 to T 34 each independently is selected from the group consisting of 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 )- ', b31 to b34 are each independently an integer of 0 to 10, Y 31 to Y 34 each independently is 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 each represent a binding site for M 31 , R 31 to R 38 each independently is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidine group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arysthio group, a substituted or unsubstituted C1-C 60 heteroaryl group, 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(=0)(Q1), -S(=0)(Q1), -S(=0)2(Q1), -P(=0)(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 group or a substituted or unsubstituted C1-C 60 heterocyclic group, and wherein, in Formula 4, b41 to b43 are each independently an integer of 0 to 10, X 41 is N, B, P(=)(R 44 ) or P(=S)(R 44 ), Y 41 to Y 43 each independently O, S, N(R 45 ), B(R 45 ), C(R 45 )(R 46 ) or Si(R 45 )(R 46 ), k41 is 0 or 1, and when k41 is 0, the -(Y 41 ) k41 - is absent, A 41 to A 43 each independently selected from C5-C 30 carbocyclic groups and C1-C 30 heterocyclic groups, R 41 to R 46 each independently is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidine group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C1-C 60 heteroaryl group, 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(=0)(Q1), -S(=0)(Q1), -S(=0)2(Q1), -P(=0)(Q1)(Q2), and -P(=S)(Q1)(Q2), wherein R 41 to R 46 are optionally linked to each other to form a substituted or unsubstituted C5-C 30 carbocyclic group or a substituted or unsubstituted C1-C 30 heterocyclic group, and wherein, in Formula 1, Formula 2A, Formula 2B, Formula 3, and Formula 4, 2. The organic light-emitting device according to claim 1, wherein the first compound, the second compound, and the third compound are not intended to emit light. Q1to Q3, Q 21 to Q 23 and Q 31 to Q 33 each independently is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidine group, a hydrazine group, a hydrazone group, a C1-C 60 alkyl group, a C2-C 60 alkenyl group, a C2-C 60 alkynyl group, a C1-C 60 alkoxy group, a C3-C 10 cycloalkyl group, a C1-C 10 heterocycloalkyl group, a C3-C 10 cycloalkenyl group, a C1-C 10 heterocycloalkenyl group, a C6-C 60 aryl group, a C6-C 60 aryloxy group, a C6-C 60 arylthio group, a C1-C 60 heteroaryl group, a C1-C 60 heteroaryloxy group, a C1-C 60 heteroarylthio group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, a biphenyl group, and a terphenyl group.
3. The organic light-emitting device according to claim 1, wherein the fourth compound is intended to emit light.
4. The organic light-emitting device according to claim 1, wherein the ratio of light emitted from the fourth compound to the total light emitted from the emission layer is 80% or more than 80%. a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a benzophenanthryl group, a chrysenyl group, a fluoranthenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzofluorenyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a dibenzofluorenyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, and a dinaphthothiophenyl group; 5. The organic light emitting device as claimed in claim 1, wherein R 11 to at least one of R 19 is represented by - (L 11 ) a11 - A 11 .
6. The organic light emitting device of claim 1, wherein X 11 is N(R 19 ).
7. The organic light emitting device of claim 1, wherein A 11 is selected from the group consisting of: in Formulae 8-1 to 8-5, Each was selected from deuterium, C1-C 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, phenanthrene groups, benzo[a]phenanthrene groups, benzo[b]yl groups, fluorenyl groups, carbazole groups, dibenzofuranyl groups, dibenzothiopheneyl groups, benzo[a]fluorenyl groups, benzo[a]carbazoleyl groups, benzo[a]naphthofuranyl groups, benzo[a]naphthothiopheneyl groups, dibenzo[a]fluorenyl groups, dibenzo[a]carbazoleyl groups, dibenzo[a]furanyl groups, dibenzo[a]naphthothiopheneyl groups, -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 At least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group, phenyl group, fluoranyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzo[a]fluorenyl group, benzo[a]carbazole group, benzo[a]naphthofuranyl group, benzo[a]naphthothiophenyl group, dibenzo[a]fluorenyl group, dibenzo[a]carbazole group, dinaphthofuranyl group and dinaphthothiophenyl group; and Each was selected independently from deuterium, C1-C 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, phenanthrene groups, benzo[a]phenanthrene groups, benzo[b]yl groups, fluorenyl groups, carbazole groups, dibenzofuranyl groups, dibenzothiopheneyl groups, benzo[a]fluorenyl groups, benzo[a]carbazoleyl groups, benzo[a]naphthofuranyl groups, benzo[a]naphthothiopheneyl groups, dibenzo[a]fluorenyl groups, dibenzo[a]carbazoleyl groups, dibenzo[a]furanyl groups, dibenzo[a]naphthothiopheneyl groups, -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 At least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group, phenyl group, fluoranyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzo[a]fluorenyl group, benzo[a]carbazole group, benzo[a]naphthofuranyl group, benzo[a]naphthothiophenyl group, dibenzo[a]fluorenyl group, dibenzo[a]carbazole group, dibenzofuranyl group and dibenzothiophenyl group At least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group, benzo[a]yl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiophenyl group, benzo[a]fluorenyl group, benzo[a]carbazole group, benzo[a]naphthofuranyl group, benzo[a]naphthothiophenyl group, dibenzo[a]fluorenyl group, dibenzo[a]carbazole group, dinaphthofuranyl group and dinaphthothiophenyl group.
8. The organic light emitting device as claimed in claim 1, wherein A 11 is represented by one of formula 8-1 to formula 8-5: wherein, 9. The organic light-emitting device according to claim 1, wherein the first compound is represented by one of Formulae 1-1 to 1-5: X 81 selected from O, S, N(R 89 ) and C(R 89 )(R 90 ), R 81 to R 90 each independently is selected from the group consisting of hydrogen, deuterium, C1-C 20 alkyl group, phenyl group, biphenyl group, terphenyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, and dibenzothiophenyl group, and represents a binding site to an adjacent atom. wherein In Formulae 1-1 to 1-5, L 11 , a11, A 11 and R 11 to R 19 each are the same as defined for Formula 1, respectively.
10. The organic light emitting device of claim 1, wherein: at least one of R 21 , R 22 , R 24 , and R 25 in formula 2A is said to be derived from -(L 21 ) a21 -A 21 represents a group, and at least one R in the number of (6-k23) in Formula 2B 23 is the by -(L 21 ) a21 -A 21 group represented by 11. The organic light emitting device of claim 1, wherein A 21 is selected from: a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a benzophenanthryl group, a chrysenyl group, a fluoranthenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridyl group, a pyrazinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a naphthidinyl group, a quinoxalyl group, and a quinazolyl group; Each is selected from deuterium, -F, cyano group, C1-C 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, phenanthrene groups, benzo[a]phenanthrene groups, phenyl groups, fluorenyl groups, carbazole groups, dibenzofuranyl groups, dibenzothiopheneyl groups, pyridyl groups, pyrazinyl groups, pyrimidinyl groups, triazineyl groups, quinolinyl groups, isoquinolinyl groups, naphthidyl groups, quinoxalinyl groups, quinazolinyl groups, -C(Q) 31 (Q) 32 (Q) 33 ), -Si(Q 31 (Q) 32 (Q) 33 -B(Q) 31 (Q) 32 -N(Q) 31 (Q) 32 -S(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) and -P(=S)(Q 31 (Q) 32 At least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group, phenyl group, fluorenyl group, carbazole group, dibenzofuranyl group, dibenzothiopheneyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, naphthidyl group, quinoxalinyl group, and quinazolinyl group; and Each is selected independently from deuterium, -F, cyano groups, C1-C 20 Alkyl groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, phenanthrene groups, benzo[a]phenanthrene groups, phenyl groups, fluorenyl groups, carbazole groups, dibenzofuranyl groups, dibenzothiopheneyl groups, pyridyl groups, pyrazinyl groups, pyrimidinyl groups, triazineyl groups, quinolinyl groups, isoquinolinyl groups, naphthidyl groups, quinoxalinyl groups, quinazolinyl groups, -C(Q) 21 (Q) 22 (Q) 23 ), -Si(Q 21 (Q) 22 (Q) 23 -B(Q) 21 (Q) 22 -N(Q) 21 (Q) 22 -S(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) and -P(=S)(Q 21 (Q) 22 The substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, benzo[a]phenanthrene group, hydroxyl group, fluoranyl group, carbazole group, dibenzofuranyl group, dibenzothiophene group, pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, naphthidyl group, quinoxalinyl group and quinazolinyl group are at least one of the following:
12. The organic light emitting device of claim 1, wherein the second compound is represented by Formula 2-1 or Formula 2-2: wherein In Formulae 2-1 and 2-2, X 21 selected from O, S, N(R 24 ) and C(R 24 )(R 25 ), R 21a to R 21c , R 22a to R 22d , R 23a to R 23e , R 24 and R 25 are each independently selected from: Depend on -(L 21 ) a21 -A 21 The groups represented are hydrogen, deuterium, -F, cyano groups, and C1-C. 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2); Each is selected from deuterium, -F, cyano group, C1-C 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q) 31 (Q) 32 (Q) 33 ), -Si(Q 31 (Q) 32 (Q) 33 -B(Q) 31 (Q) 32 -N(Q) 31 (Q) 32 -S(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) and -P(=S)(Q 31 (Q) 32 At least one substituted cyclic group containing π-electron-depleted nitrogen and a cyclic group not containing π-electron-depleted nitrogen; and Each is selected independently from deuterium, -F, cyano groups, C1-C 60 Alkyl groups, cyclic groups containing nitrogen with depleted π electrons, cyclic groups without nitrogen with depleted π electrons, -C(Q) 21 (Q) 22 (Q) 23 ), -Si(Q 21 (Q) 22 (Q) 23 -B(Q) 21 (Q) 22 -N(Q) 21 (Q) 22 -S(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) and -P(=S)(Q 21 (Q) 22 At least one substituted cyclic group containing π-electron-depleted nitrogen and at least one substituted cyclic group not containing π-electron-depleted nitrogen in the cyclic group of ) at least one of R 21a to R 21c , R 22a to R 22d , R 24 and R 25 is said group represented by -(L 21 ) a21 -A 21 , at least one of R 23a to R 23e in the group of -(L 21 ) a21 -A 21 represented by the group Q1to Q3, Q 21 to Q 23 and Q 31 to Q 33 each independently is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidine group, a hydrazine group, a hydrazone group, a C1-C20alkyl group, a C2-C20alkenyl group, a C2-C20alkynyl group, a C1-C20alkoxy group, a C3-C20cycloalkyl group, a C1-C20heterocycloalkyl group, a C3-C20cycloalkenyl group, a C1-C20heterocycloalkenyl group, a C6-C20aryl group, a C6-C20aryloxy group, a C6-C20arylthio group, a C1-C20heteroaryl group, a C1-C20heteroaryloxy group, a C1-C20heteroarylthio group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, a biphenyl group, and a terphenyl group. 60 60 60 60 10 10 10 10 60 60 60 60 60 60 each independently is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidine group, a hydrazine group, a hydrazone group, a C1-C20alkyl group, a C2-C20alkenyl group, a C2-C20alkynyl group, a C1-C20alkoxy group, a C3-C20cycloalkyl group, a C1-C20heterocycloalkyl group, a C3-C20cycloalkenyl group, a C1-C20heterocycloalkenyl group, a C6-C20aryl group, a C6-C20aryloxy group, a C6-C20arylthio group, a C1-C20heteroaryl group, a C1-C20heteroaryloxy group, a C1-C20heteroarylthio group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, a biphenyl group, and a terphenyl group. 13. The organic light emitting device of claim 1, wherein the third compound is represented by Formula 3-1 or Formula 3-2: wherein, In Formulae 3-1 and 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 identical to the respective definitions with respect to formula 3.
14. The organic light emitting device as claimed in claim 1, wherein X 41 is N or B.
15. The organic light emitting device of claim 1, wherein the fourth compound is represented by Formula 4-1: <Formula 4-1> , wherein X 41 , Y 42 , Y 43 , A 41 to A 43 , R 41 to R 43 and b41 to b43 are the same as defined in relation to formula 4.
16. The organic light emitting device of claim 1, wherein the fourth compound is represented by Formula 4-11 or Formula 4-12: wherein In Formulae 4-11 and 4-12, R 41a to R 41d , R 42a to R 42d , R 43a to R 43c , R 44a to R 44d , R 45a , R 45b and R 46a to R 46c each are the same as defined for R 41 in Formula 4, respectively.
17. The organic light emitting device of 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 compounds of Group III-I and Group III-II, and the fourth compound is selected from the compounds of Group IV: <Group I> <Group II> <Group III-I> <Group III-II> <Group IV> , wherein Me represents a methyl group, iso-Pr represents an iso-propyl group, and tert-Bu represents a tert-butyl group.
18. The organic light emitting device of claim 1, wherein the first electrode is an anode, the second electrode is a cathode, the organic layer further comprises a hole transport zone between the first electrode and the emission layer and / or an electron transport zone between the emission layer and the second electrode, the hole transport zone comprises a hole injection layer, a hole transport layer, an emission auxiliary layer, and / or an electron blocking layer, and the electron transport zone comprises 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 10: <Formula 10> wherein In Formula 10, L 101 to L 103 each independently selected from substituted or unsubstituted C5-C 30 carbocyclic groups and substituted or unsubstituted C1-C 30 heterocyclic groups, a101 to a103 are each independently selected from 0, 1, and 2, and R 101 to R 103 each independently is selected from the group consisting of a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C1-C 60 heteroaryl group, 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(=0)(Q1), -S(=0)(Q1), -S(=0)2(Q1), -P(=0)(Q1)(Q2), and -P(=S)(Q1)(Q2), wherein Q1to Q3are the same as defined in claim 1.
20. An apparatus comprising: a thin film transistor comprising a source electrode, a drain electrode, and an active layer; and the organic light emitting device of claim 1, wherein 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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