Amine-containing compound, organic light-emitting device, electronic device, and electronic equipment

Abstract

Amine-containing compound represented by Formula 1, organic light-emitting device, electronic device, and electronic equipment: Formula 1 # imgabs0 #

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0092467 filed in the Korean Intellectual Property Office on July 17, 2023, the entire contents of which are incorporated herein by reference. Technical Field

[0003] One or more embodiments of the present disclosure relate to amine-containing compounds, organic light-emitting devices, electronic devices, and electronic equipment. Background Art

[0004] An organic light emitting device (OLED) is a self-emissive device that has a relatively wide viewing angle, a relatively high contrast ratio, a relatively short response time, and excellent or suitable characteristics in terms of brightness, driving voltage, and response speed compared to other comparable devices of the related art, and produces full-color images.

[0005] The organic light emitting device may include a first electrode located on a substrate and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes provided from the first electrode move toward the emission layer through the hole transport region, and electrons provided from the second electrode move toward the emission layer through the electron transport region. Carriers such as holes and electrons recombine in the emission layer to generate excitons. Excitons can transition from an excited state and decay to a ground state, thereby generating light. Summary of the invention

[0006] One or more aspects of the embodiments of the present disclosure relate to an amine-containing compound with improved hole transport properties and a light-emitting device having high efficiency, low driving voltage and long life by using the amine-containing compound. One or more aspects of the embodiments of the present disclosure relate to high-quality electronic devices and electronic equipment including the light-emitting device.

[0007] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be taught by practice of the presented embodiments of the disclosure.

[0008] According to one or more embodiments of the present disclosure, an amine-containing compound represented by Formula 1 is provided:

[0009] Formula 1

[0010]

[0011] Wherein, in Formula 1, Ar 11 ,Ar 12 and Ar 21 Can be independently C 3 -C60 Carbocyclic or C 1 -C 60 Heterocyclic group,

[0012] Ar 31 ,Ar 32 , L 2 and L 3 may be independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0013] m2 can be an integer from 0 to 5,

[0014] When m2 is 0, *-(L 2 ) m2 The group represented by -*' can be a single bond,

[0015] m3 can be 1, 3 or 4,

[0016] X can be C(R 4 )(R 5 )、N(R 6 ), O or S,

[0017] R 1 , R 2 , R 4 , R 5 and R 6 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10a A substituted monovalent non-aromatic fused polycyclic group, unsubstituted or substituted with at least one R 10a Substituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) or -P(=S)(Q 1 )(Q 2 ),

[0018] Selected from R 1 , R 2 , R 4 , R 5 and R 6Two or more adjacent groups thereof may be optionally bonded to each other (ie, may be bonded to each other or may not be bonded to each other) to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0019] n1 and n2 can each independently be an integer from 0 to 15,

[0020] When n1 is an integer of 2 or more, multiple R 1 can be the same or different from each other,

[0021] When n2 is an integer of 2 or greater, multiple R 2 can be the same or different from each other,

[0022] R 10a Can be:

[0023] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro,

[0024] C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, -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 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof,

[0025] C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy or C 6 -C 60 Arylthio, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, -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 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof, or

[0026] -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 ) or -P(=O)(Q 31 )(Q 32 ),

[0027] Q 1 To Q 3 , Q 11 To Q 13, Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; or C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic groups, each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 substituted with alkoxy, phenyl, biphenyl or any combination thereof, and

[0028] * and *' can each independently indicate a binding site with an adjacent atom.

[0029] According to one or more embodiments of the present disclosure, an organic light-emitting device includes a first electrode, a second electrode facing the first electrode, an intermediate layer between the first electrode and the second electrode and including an emission layer, and at least one amine-containing compound described above.

[0030] According to one or more embodiments of the present disclosure, an electronic device includes the organic light emitting device.

[0031] According to one or more embodiments of the present disclosure, an electronic equipment includes the organic light emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0032] The accompanying drawings are included to provide a further understanding of the present disclosure and are incorporated into and constitute a part of the present disclosure. The accompanying drawings illustrate embodiments of the present disclosure and together with the specification are used to illustrate the principles of the present disclosure. The above and other aspects, features and advantages of specific embodiments of the present disclosure will become more apparent through the following description in conjunction with the accompanying drawings, in which:

[0033] Figure 1 is a schematic cross-sectional view of the structure of an organic light-emitting device according to one or more embodiments of the present disclosure;

[0034] Figure 2 is a schematic cross-sectional view showing the structure of a light emitting device according to one or more embodiments of the present disclosure;

[0035] Figure 3 is a schematic cross-sectional view illustrating a structure of a light emitting device according to one or more embodiments of the present disclosure.

[0036] Figure 4 is a schematic perspective view of an electronic device including an organic light emitting device according to one or more embodiments of the present disclosure;

[0037] Figure 5 is a schematic diagram showing the exterior of a vehicle as electronic equipment including an organic light emitting device according to one or more embodiments of the present disclosure; and

[0038] Fig. 6A , Figure 6B and Figure 6C Each is a schematic diagram of a vehicle interior according to one or more embodiments of the present disclosure. DETAILED DESCRIPTION

[0039] Now will be more detailed with reference to embodiment, the example of embodiment is shown in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout the disclosure, and may not provide its repeated description.In this respect, the embodiment of the present disclosure may have different forms, and should not be construed as being limited to the description set forth in this article.Therefore, the embodiment of the present disclosure is described only by reference to the accompanying drawings, to illustrate the various aspects of the present disclosure.As used in this article, the term "and / or" or "or" may include any combination and all combinations of one or more related listed items.Throughout the present disclosure, such as "at least one (person / kind) in ... ", "one (person / kind) in ... " and "selected from ... " before or after a column of elements, what is modified is the whole column of elements, rather than modifying the individual elements in the column. For example, "at least one selected from a, b, and c", "at least one selected from a to c", etc. may indicate only a, only b, only c, both a and b (e.g., both a and b), both a and c (e.g., both a and c), both b and c (e.g., both b and c), all a, b, and c, or variations thereof. As appropriate, the " / " used herein may be interpreted as "and" or "or".

[0040] According to one or more embodiments of the present disclosure, an amine-containing compound is provided.

[0041] The amine-containing compound can be represented by Formula 1:

[0042] Formula 1

[0043]

[0044] In Formula 1, X can be C(R 4 )(R 5)、N(R 6 ), O or S.

[0045] In formula 1, Ar 11 ,Ar 12 and Ar 21 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.

[0046] In one or more embodiments, Ar 11 and Ar 12 can be independently phenyl, naphthyl, phenanthryl, fluoranthenyl, triphenylenyl, pyrene, 1-4-dime, 1-6-dime, 1-8 ...

[0047] In one or more embodiments, the amine-containing compound represented by Formula 1 may be a compound represented by any one selected from Formula 1-1 to Formula 1-4:

[0048] Formula 1-1

[0049]

[0050] Formula 1-2

[0051]

[0052] Formula 1-3

[0053]

[0054] Formula 1-4

[0055]

[0056] Among them, in Formula 1-1 to Formula 1-4, Ar 21 ,Ar 31 ,Ar 32 , L 2 , L 3 , m2, m3, X, R 2 and n2 may each independently be the same as described herein, and

[0057] R 11 To R 18can be independently compared with the R 1 Same as described.

[0058] In one or more embodiments, the amine-containing compound represented by Formula 1 may be a compound represented by Formula 1-2.

[0059] In one or more embodiments, R 14 can be hydrogen, deuterium, unsubstituted or replaced by at least one R 10a Substituted C 1 -C 10 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 10 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 10 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 6 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 6 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 6 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 6 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 30 Aryl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heteroaryl, unsubstituted or substituted with at least one R 10a A substituted monovalent non-aromatic fused polycyclic group, unsubstituted or substituted with at least one R 10a Substituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q1 )、-P(=O)(Q 1 )(Q 2 ) or -P(=S)(Q 1 )(Q 2 ). Q 1 , Q 2 and Q 3 may each independently be the same as described herein.

[0060] In one or more embodiments, Ar 21 It can be phenyl, naphthyl, phenanthryl, fluoranthenyl, triphenylenyl, pyrene, 1-4-dime, 1-6-dime, 1-8 ...

[0061] In one or more embodiments, The group represented may be a group represented by Formula 2A or Formula 2B:

[0062] Formula 2A

[0063]

[0064] Formula 2B

[0065]

[0066] Wherein, in Formula 2A and Formula 2B, R 21 To R 28 can be independently compared with the R 2 Same as described, and

[0067] *Indicates the binding site with the neighboring atoms.

[0068] In one or more embodiments, The group represented may be a group represented by Formula 2A.

[0069] In one or more embodiments, in Formula 2A, R 21 or R 23 It may be unsubstituted or substituted with at least one R 10a Substituted C 6 -C 30 Aryl.

[0070] In one or more embodiments, in Formula 2A, R 21 or R 23It may be unsubstituted or substituted with at least one R 10a Substituted phenyl.

[0071] In one or more embodiments, in Formula 2A, R 21 It may be unsubstituted or substituted with at least one R 10a Substituted C 6 -C 30 Aryl, and

[0072] R 23 To R 28 can be each independently hydrogen, deuterium, unsubstituted or replaced by at least one R 10a Substituted C 1 -C 10 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 10 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 10 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 6 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 6 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 6 Cycloalkenyl, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 6 Heterocycloalkenyl.

[0073] In one or more embodiments, in Formula 2A, R 21 It may be unsubstituted or substituted with at least one R 10a substituted phenyl, and

[0074] R 23 To R 28 can be each independently hydrogen, deuterium, unsubstituted or replaced by at least one R 10a Substituted C 1 -C 10 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 10 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 10 Alkynyl, unsubstituted or substituted with at least one R 10aSubstituted C 3 -C 6 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 6 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 6 Cycloalkenyl, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 6 Heterocycloalkenyl.

[0075] In one or more embodiments, in Formula 2A, R 23 It may be unsubstituted or substituted with at least one R 10a Substituted C 6 -C 30 Aryl, and

[0076] R 21 and R 24 To R 28 can be each independently hydrogen, deuterium, unsubstituted or replaced by at least one R 10a Substituted C 1 -C 10 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 10 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 10 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 6 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 6 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 6 Cycloalkenyl, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 6 Heterocycloalkenyl.

[0077] In one or more embodiments, in Formula 2A, R 23 It may be unsubstituted or substituted with at least one R 10a substituted phenyl, and

[0078] R 21 and R 24 To R28 can be each independently hydrogen, deuterium, unsubstituted or replaced by at least one R 10a Substituted C 1 -C 10 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 10 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 10 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 6 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 6 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 6 Cycloalkenyl, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 6 Heterocycloalkenyl.

[0079] In one or more embodiments, The group represented may be a group represented by Formula 2B.

[0080] In one or more embodiments, in Formula 2B, R 22 It may be unsubstituted or substituted with at least one R 10a Substituted C 6 -C 30 Aryl, and

[0081] R 23 To R 28 can be each independently hydrogen, deuterium, unsubstituted or replaced by at least one R 10a Substituted C 1 -C 10 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 10 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 10 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 6 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 6Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 6 Cycloalkenyl, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 6 Heterocycloalkenyl.

[0082] In one or more embodiments, in Formula 2B, R 22 It may be unsubstituted or substituted with at least one R 10a substituted phenyl, and

[0083] R 23 To R 28 can be each independently hydrogen, deuterium, unsubstituted or replaced by at least one R 10a Substituted C 1 -C 10 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 10 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 10 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 6 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 6 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 6 Cycloalkenyl, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 6 Heterocycloalkenyl.

[0084] In Formula 1, m2 may be an integer from 0 to 5. When m2 is 0, 2 ) m2 The group represented by -*' may be a single bond.

[0085] In one or more embodiments, m2 may be 0, 1, or 2.

[0086] In formula 1, L 2 It may be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1-C 60 Heterocyclic group.

[0087] In one or more embodiments, L 2 It may be unsubstituted or substituted with at least one R 10a Substituted phenyl, unsubstituted or replaced by at least one R 10a substituted naphthyl, unsubstituted or replaced by at least one R 10a substituted anthracenyl, or unsubstituted or replaced by at least one R 10a Replaced by Fiki.

[0088] In formula 1, L 3 It may be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.

[0089] In one or more embodiments, L 3 It may be unsubstituted or substituted with at least one R 10a Substituted phenyl, unsubstituted or replaced by at least one R 10a substituted naphthyl, unsubstituted or replaced by at least one R 10a substituted anthracenyl, or unsubstituted or replaced by at least one R 10a Replaced by Fiki.

[0090] In one or more embodiments, L 3 It may be a group represented by any one selected from Formula 3A to Formula 3J:

[0091]

[0092] In Formula 3A to Formula 3J, Z 31 To Z 38 can be independently compared with the R 10a Same as described, and

[0093] * and *' can each independently indicate a binding site with an adjacent atom.

[0094] In Formula 1, m3 may be 1, 3 or 4.

[0095] In one or more embodiments, m3 may not be 2.

[0096] In one or more embodiments, m3 may not be zero.

[0097] Ar 31 and Ar 32may be independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.

[0098] In one or more embodiments, Ar 31 and Ar 32 may be independently unsubstituted or substituted with at least one R 10a Substituted C 6 -C 30 Aryl, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heteroaryl.

[0099] In one or more embodiments, Ar 31 and Ar 32 can be each independently unsubstituted or substituted with at least one R 10a Substituted phenyl or naphthyl.

[0100] In one or more embodiments, Ar 31 and Ar 32 may be each independently unsubstituted or substituted with:

[0101] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0102] C 1 -C 10 Alkyl, C 2 -C 10 Alkenyl, C 2 -C 10 Alkynyl or C 1 -C 10 alkoxy, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, or any combination thereof;

[0103] C 1 -C 10 Cycloalkyl, C 2 -C 10 Cycloalkenyl, phenyl or naphthyl, each of which is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 10 Alkyl, C 2 -C 10 Alkenyl, C 2 -C 10Alkynyl, C 1 -C 10 Alkoxy or any combination thereof; or

[0104] Any combination of them.

[0105] In formula 1, R 1 , R 2 , R 4 , R 5 and R 6 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C60 Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10a A substituted monovalent non-aromatic fused polycyclic group, unsubstituted or substituted with at least one R 10a Substituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) or -P(=S)(Q 1 )(Q 2 ).

[0106] Selected from R 1 , R 2 , R 4 , R 5 and R 6 Two or more adjacent groups thereof may be optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.

[0107] In Formula 1, n1 and n2 may each independently be an integer from 0 to 15,

[0108] When n1 is an integer of 2 or more, multiple R 1 can be the same or different from each other, and

[0109] When n2 is an integer of 2 or greater, multiple R 2 May be the same as or different from each other.

[0110] In formula 1, R 10a Can be:

[0111] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0112] C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, -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 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof;

[0113] C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy or C 6 -C 60 Arylthio, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C6 -C 60 Arylthio, -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 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or

[0114] -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 ) or -P(=O)(Q 31 )(Q 32 ),

[0115] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; or C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic groups, each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 substituted with alkoxy, phenyl, biphenyl or any combination thereof, and

[0116] * and *' can each independently indicate a binding site with an adjacent atom.

[0117] In one or more embodiments, the amine-containing compound represented by Formula 1 may be one of Compounds 1 to 182 (eg, one selected from Compounds 1 to 182); however, embodiments of the present disclosure are not limited thereto:

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131] The amine-containing compound represented by Formula 1 may satisfy the following conditions: The structure in which a group represented by, a carbazolyl group, a fluorenyl group, a dibenzofuranyl group or a dibenzothiophene group is introduced into the diamine can improve the charge transport characteristics of the amine-containing compound by such a structure. Therefore, the exciton generation efficiency in the emission layer can be improved.

[0132] Although not limited by a particular theory, when the amine-containing compound of the present disclosure (such as the examples of the present disclosure) is used in a hole transport layer, the substituents may be changed differently between the first electrode and the second electrode, which causes one or more suitable changes in the highest occupied molecular orbital (HOMO) energy level. Therefore, when the amine-containing compound of the present disclosure (such as the examples of the present disclosure) is used in a hole transport layer, the exciton generation efficiency in the emission layer may be improved by differently changing the hole injection barrier of the hole transport layer.

[0133] The amine-containing compounds of the present disclosure (such as the examples of the present disclosure) can widen the band gap by adopting a structure in which two amines are connected to each other, and because the amine-containing compounds have tricyclic groups, such as fluorenyl, carbazole, etc., polarons can be stabilized to provide a long life of the light-emitting device. In addition, the increased charge jump rate can improve the charge mobility. In addition, by introducing a substituent into the naphthyl group, the color coordinates can be improved to emit deep blue light, and the structural stability of the compound can be ensured. By applying this to the emission layer of the light-emitting device, the luminous efficiency and device life can be improved.

[0134] Therefore, when the amine-containing compound represented by Formula 1 is applied to an organic light-emitting device, the device efficiency, driving voltage and life characteristics can be significantly improved. For example, by including the amine-containing compound represented by Formula 1 in the hole transport layer, an organic light-emitting device with high efficiency, low driving voltage and long life can be realized.

[0135] One of ordinary skill in the art can recognize a method for synthesizing the amine-containing compound represented by Formula 1 by referring to the examples provided herein.

[0136] According to one or more embodiments of the present disclosure, an organic light-emitting device may include: a first electrode; a second electrode facing the first electrode; an intermediate layer between the first electrode and the second electrode and including an emission layer; and at least one amine-containing compound described above.

[0137] In one or more embodiments, the first electrode may be an anode,

[0138] The second electrode may be a cathode,

[0139] The intermediate layer may further include a hole transport region between the first electrode and the emissive layer and an electron transport region between the emissive layer and the second electrode.

[0140] The hole transport region may include at least one selected from a hole injection layer, a hole transport layer, a buffer layer, an emission auxiliary layer, and an electron blocking layer, and

[0141] The electron transport region may include at least one selected from among a hole blocking layer, an electron transport layer, and an electron injection layer.

[0142] According to one or more embodiments, an amine-containing compound may be included in an intermediate layer.

[0143] According to one or more embodiments, the amine-containing compound may be included in the hole transport region.

[0144] According to one or more embodiments, the amine-containing compound may be included in a hole transport layer. The hole transport layer may be in direct contact with the emission layer.

[0145] According to one or more embodiments, the organic light emitting device may further include a covering layer arranged outside the first electrode (e.g., on the first electrode) or a covering layer arranged outside the second electrode (e.g., on the second electrode). For example, the organic light emitting device may further include at least one of a first covering layer arranged outside the first electrode (e.g., on the first electrode) and a second covering layer arranged outside the second electrode (e.g., on the second electrode), and at least one of the first covering layer and the second covering layer may include an amine-containing compound. For more details of the first covering layer and / or the second covering layer, reference may be made to the relevant description provided herein.

[0146] According to one or more embodiments, the organic light-emitting device may further include a first covering layer arranged outside the first electrode (e.g., on the first electrode). For example, the first covering layer may include an amine-containing compound represented by Formula 1. According to one or more embodiments, the organic light-emitting device may further include a second covering layer arranged outside the second electrode (e.g., on the second electrode). For example, the second covering layer may include an amine-containing compound represented by Formula 1. According to one or more embodiments, the organic light-emitting device may further include a first covering layer arranged outside the first electrode (e.g., on the first electrode) and a second covering layer arranged outside the second electrode (e.g., on the second electrode). For example, at least one of the first covering layer and the second covering layer may include an amine-containing compound represented by Formula 1.

[0147] According to one or more embodiments of the present disclosure, the electronic device may include an organic light-emitting device. The electronic device may further include a thin film transistor. In one or more embodiments, the electronic device may further include a thin film transistor, the thin film transistor including a source electrode and a drain electrode, and the first electrode of the organic light-emitting device may be electrically connected to the source electrode or the drain electrode. In one or more embodiments, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof. For more details about the electronic device, reference may be made to the relevant description provided herein.

[0148] According to one or more embodiments of the present disclosure, electronic equipment may include an organic light emitting device.

[0149] For example, the electronic equipment can be at least one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television (TV), a billboard, indoor or outdoor lighting and / or signaling, a head-up display, a fully or partially transparent display, a flexible display (such as a rollable display, a foldable display, or a stretchable display), a laser printer, a phone (such as a cellular phone or a tablet phone), a tablet computer, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual or augmented reality display, a vehicle, a video wall comprising multiple displays stitched together, a theater or stadium screen, a light therapy device, and a sign.

[0150] Figure 1 Description

[0151] Figure 1 is a schematic cross-sectional view of a structure of an organic light emitting device 10 according to one or more embodiments of the present disclosure. The organic light emitting device 10 may include a first electrode 110, an intermediate layer 130, and a second electrode 150.

[0152] In the following, reference will be made to Figure 1 A structure of an organic light emitting device 10 and a method of manufacturing the organic light emitting device 10 according to one or more embodiments are described.

[0153] First electrode 110

[0154] exist Figure 1 In one or more embodiments, a substrate may be additionally provided, and the substrate is located below the first electrode 110 and / or on the second electrode 150. As the substrate, a glass substrate or a plastic substrate may be used. In one or more embodiments, the substrate may be a flexible substrate and may include a plastic having excellent or suitable heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.

[0155] The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be a high work function material that facilitates hole injection.

[0156] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In one or more embodiments, when the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO), or any combination thereof. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0157] The first electrode 110 may have a single-layer structure including (eg, consisting of) a single layer or a multi-layer structure including a plurality of layers. For example, in some embodiments, the first electrode 110 may have a triple-layer structure of ITO / Ag / ITO.

[0158] Middle layer 130

[0159] The intermediate layer 130 may be on the first electrode 110. The intermediate layer 130 may include an emission layer.

[0160] In one or more embodiments, the intermediate layer 130 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 150 .

[0161] In one or more embodiments, the intermediate layer 130 may further include metal-containing compounds such as organometallic compounds and / or inorganic materials such as quantum dots, in addition to one or more suitable organic materials.

[0162] In one or more embodiments, the intermediate layer 130 may include: i) two or more emission units sequentially stacked between the first electrode 110 and the second electrode 150; and ii) a charge generation layer between the two or more emission units. When the intermediate layer 130 includes two or more emission units and the charge generation layer, the organic light emitting device 10 may be a tandem organic light emitting device.

[0163] Hole transport region in the intermediate layer 130

[0164] The hole transport region may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material; ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of different materials; or iii) a multilayer structure including a plurality of layers including different materials.

[0165] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof.

[0166] For example, in one or more embodiments, the hole transport region may have a multi-layer structure, which includes a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure or a hole injection layer / hole transport layer / emission assisting layer structure, the constituent layers of each structure being stacked sequentially from the first electrode 110 in the order stated.

[0167] In one or more embodiments, the hole transport region may include an amine-containing compound, for example, an amine-containing compound of one or more embodiments of the present disclosure. For example, the hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:

[0168] Formula 201

[0169]

[0170] Formula 202

[0171]

[0172] Among them, in equation 201 and equation 202, L 201 To L 204 may be independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0173] L 205 Can be *-O-*', *-S-*', *-N(Q 201 )-*', unsubstituted or replaced by at least one R 10a Substituted C 1 -C 20 Alkylene, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 20 Alkenylene, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0174] xa1 to xa4 can each independently be an integer from 0 to 5,

[0175] xa5 can be an integer from 1 to 10,

[0176] R 201 To R 204 and Q 201 may be independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0177] R 201 and R 202 may be optionally substituted via a single bond, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 5 Alkylene, either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 5 The alkenylene groups are connected to each other to form an unsubstituted or substituted R 10a Substituted C 8 -C 60 Polycyclic groups (eg, carbazole groups, etc.) (eg, see compound HT16),

[0178] R 203 and R 204 may be optionally substituted via a single bond, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 5 Alkylene, either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 5 The alkenylene groups are connected to each other to form an unsubstituted or substituted R 10a Substituted C 8 -C 60 Polycyclic groups, and

[0179] na1 can be an integer from 1 to 4.

[0180] For example, in some embodiments, each of Formula 201 and Formula 202 may include at least one selected from the groups represented by Formula CY201 to Formula CY217:

[0181]

[0182] In formulas CY201 to CY217, R 10b and R 10c can be respectively related to R 10aSame as described, CY 201 To Ring CY 204 Can be independently C 3 -C 20 Carbocyclic or C 1 -C 20 heterocyclic group, and at least one hydrogen in Formula CY201 to Formula CY217 may be unsubstituted or replaced by R 10a replace.

[0183] In one or more embodiments, ring CY in Formula CY201 to Formula CY217 201 To Ring CY 204 Each independently may be phenyl, naphthyl, phenanthryl or anthracenyl.

[0184] In one or more embodiments, each of Formula 201 and Formula 202 may include at least one selected from the groups represented by Formula CY201 to Formula CY203.

[0185] In one or more embodiments, Formula 201 may include at least one selected from the groups represented by Formulas CY201 to CY203 and at least one selected from the groups represented by Formulas CY204 to CY217.

[0186] In one or more embodiments, in formula 201, xa1 may be 1, R 201 may be a group represented by one selected from Formula CY201 to Formula CY203, xa2 may be 0, and R 202 It may be a group represented by one selected from the group consisting of Formula CY204 to Formula CY207.

[0187] In one or more embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) a group represented by one selected from Formula CY201 to Formula CY203.

[0188] In one or more embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) a group represented by one selected from Formula CY201 to Formula CY203, and may include at least one selected from a group represented by Formula CY204 to Formula CY217.

[0189] In one or more embodiments, each of Formula 201 and Formula 202 may not include (e.g., may exclude) a group represented by one selected from Formula CY201 to Formula CY217. In the present disclosure, "not including "component" or any "component", "excluding "component" or any "component"" and / or "not containing "component"", etc., means that the "component" is not added, selected or used as a component in the composition / element, but in some embodiments, due to other impurities and / or external factors, less than an appropriate amount of "component" may still be included.

[0190] In one or more embodiments, the hole transport region may include at least one selected from the group consisting of compounds HT1 to HT46, 4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris[N-(2-naphthyl)-N-phenylamino]-triphenylamine (2-TNATA), N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB (NPD)), β-NPB, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine ( TPD), spiro-TPD, spiro-NPB, methylated NPB, 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-methylphenyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), or any combination thereof:

[0191]

[0192]

[0193]

[0194]

[0195]

[0196] The thickness of the hole transport region can be approximately To about within the range of, for example, about To about When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be about To about within the range of, for example, about To about and the thickness of the hole transport layer can be in the range of about To about within the range of, for example, about To about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.

[0197] The emission auxiliary layer can improve the luminous efficiency by compensating the optical resonance distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block or reduce the leakage of electrons from the emission layer to the hole transport region. The material that can be included in the hole transport region can be included in the emission auxiliary layer and the electron blocking layer.

[0198] p-dopant

[0199] In one or more embodiments, in addition to the aforementioned materials, the hole transport region may further include a charge generating material for improving the conductive properties. The charge generating material may be substantially uniformly or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer including (e.g., consisting of) the charge generating material).

[0200] The charge generating material may be, for example, a p-dopant.

[0201] For example, in some embodiments, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant can be -3.5 eV or less.

[0202] In one or more embodiments, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including the element EL1 and the element EL2, or any combination thereof.

[0203] Non-limiting examples of quinone derivatives may be tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), and the like:

[0204]

[0205] Non-limiting examples of the cyano group-containing compound may be dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) and a compound represented by Formula 221:

[0206]

[0207] Formula 221

[0208]

[0209] In formula 221, R 221 To R 223 may be independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 a heterocyclic group, and

[0210] Selected from R 221 To R 223 At least one of them can be independently: C 3 -C 60 Carbocyclic or C 1 -C 60 heterocyclic group, each substituted by cyano; -F; -Cl; -Br; -I; C substituted by cyano, -F, -Cl, -Br, -I or any combination thereof 1 -C 20 or any combination thereof. 3 -C 60 Carbocyclic or C 1 -C 60 heterocyclic group, each substituted by: cyano; -F; -Cl; -Br; -I; C substituted by cyano, -F, -Cl, -Br, -I or any combination thereof 1 -C 20 or any combination thereof.

[0211] In a compound including an element EL1 and an element EL2, the element EL1 may be a metal, a metalloid, or any combination thereof, and the element EL2 may be a nonmetal, a metalloid, or any combination thereof.

[0212] Non-limiting examples of metals may be: alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); late transition metals (e.g., zinc (Zn), indium (In), tin (Sn), etc.); and / or lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.).

[0213] Non-limiting examples of metalloids may be silicon (Si), antimony (Sb), and / or tellurium (Te).

[0214] Non-limiting examples of non-metals may be oxygen (O) and / or halogens (eg, F, Cl, Br, I, etc.).

[0215] Non-limiting examples of compounds containing element EL1 and element EL2 may be metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, or metal iodides), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, or metalloid iodides), metal tellurides, or any combination thereof.

[0216] Non-limiting examples of metal oxides may be tungsten oxide (e.g., WO, W 2 O 3 , WO 2 , WO 3 , W 2 O 5 etc.), vanadium oxide (e.g., VO, V 2 O 3 , VO 2 、V 2 O 5 etc.), molybdenum oxides (e.g., MoO, Mo 2 O 3 、MoO 2 、MoO 3 、Mo 2 O 5 etc.) and / or rhenium oxide (e.g., ReO3 wait).

[0217] Non-limiting examples of the metal halide may be alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and / or lanthanide metal halides.

[0218] Non-limiting examples of alkali metal halides may be LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and / or CsI.

[0219] A non-limiting example of the alkaline earth metal halide may be BeF 2 MgF 2 , CaF 2 , SrF 2 , BaF 2 、BeCl 2 MgCl 2 , CaCl 2 、SrCl 2 、BaCl 2 ,BeBr 2 MgBr 2 , CaBr 2 , SrBr 2 ,BaBr 2 ,BeI 2 MgI 2 ,CaI 2 , SrI 2 and / or BaI 2 .

[0220] Non-limiting examples of transition metal halides may be titanium halides (e.g., TiF 4 、TiCl 4 、TiBr 4 、TiI 4 etc.), zirconium halides (e.g., ZrF 4 、ZrCl 4 , ZrBr 4 , ZrI 4 etc.), hafnium halides (e.g., HfF 4 , HfCl 4 , HfBr 4 , HfI 4 etc.), vanadium halides (e.g., VF 3 、VCl 3 , VBr 3 VI 3 etc.), niobium halides (e.g., NbF 3、NbCl 3 , NbBr 3 , NbI 3 etc.), tantalum halides (e.g., TaF 3 、TaCl 3 、TaBr 3 、TaI 3 etc.), chromium halides (e.g., CrF 3 CrCl 3 CrBr 3 CrI 3 etc.), molybdenum halides (e.g., MoF 3 、MoCl 3 、MoBr 3 、MoI 3 etc.), tungsten halides (e.g., WF 3 、WCl 3 , WBr 3 , WI 3 etc.), manganese halides (e.g., MnF 2 、MnCl 2 、MnBr 2 、MnI 2 etc.), technetium halides (e.g., TcF 2 , TcCl 2 , TcBr 2 , TcI 2 etc.), rhenium halides (e.g., ReF 2 、ReCl 2 、ReBr 2 、ReI 2 etc.), iron halides (e.g., FeF 2 、FeCl 2 , FeBr 2 ,FeI 2 etc.), ruthenium halides (e.g., RuF 2 、RuCl 2 ,RuBr 2 , RuI 2 etc.), osmium halides (e.g., OsF 2 , OsCl 2 、OsBr 2 , OsI 2 etc.), cobalt halides (e.g., CoF 2 、CoCl 2 ,CoBr 2 、CoI 2 etc.), rhodium halides (e.g., RhF 2 , RhCl 2 , RhBr 2 , RhI 2etc.), iridium halides (e.g., IrF 2 、IrCl 2 ,IrBr 2 ,IrI 2 etc.), nickel halides (e.g., NiF 2 、NiCl 2 、NiBr 2 , NiI 2 etc.), palladium halides (e.g., PdF 2 , PdCl 2 , PdBr 2 , PdI 2 etc.), platinum halides (e.g., PtF 2 、PtCl 2 , PtBr 2 , PtI 2 etc.), copper halides (e.g., CuF, CuCl, CuBr, CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.) and / or gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.).

[0221] A non-limiting example of a late transition metal halide may be a zinc halide (e.g., ZnF 2 、ZnCl 2 、ZnBr 2 、ZnI 2 etc.), indium halides (e.g., InI 3 etc.) and / or tin halides (e.g., SnI 2 wait).

[0222] Non-limiting examples of lanthanide metal halides may include YbF, YbF 2 , YbF 3 、SmF 3 、YbCl、YbCl 2 YbCl 3 、SmCl 3 , YbBr, YbBr 2 , YbBr 3 、SmBr 3 、YbI、YbI 2 ,YbI 3 and / or SmI 3 wait.

[0223] Non-limiting examples of metalloid halides may be antimony halides (e.g., SbCl 5 etc.

[0224] Non-limiting examples of metal tellurides may be alkali metal tellurides (e.g., Li 2 Te、Na2 Te, K 2 Te、Rb 2 Te, Cs 2 Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g., TiTe 2 、ZrTe 2 、HfTe 2 、V 2 Te 3 , Nb 2 Te 3 、 2 Te 3 Cr 2 Te 3 、Mo 2 Te 3 , W 2 Te 3 , MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu 2 Te, CuTe, Ag 2 Te, AgTe, Au 2 Te, etc.), late transition metal tellurides (e.g., ZnTe, etc.) and / or lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).

[0225] Emission layer in the middle layer 130

[0226] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer can be patterned into a red emission layer, a green emission layer and / or a blue emission layer according to the sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from the red emission layer, the green emission layer and the blue emission layer, wherein the two or more layers are in contact with each other or separated from each other to emit white light (e.g., combined white light). In one or more embodiments, the emission layer may include two or more materials selected from the red light-emitting material, the green light-emitting material and the blue light-emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light (e.g., combined white light).

[0227] In one or more embodiments, the emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.

[0228] The amount of the dopant in the emission layer may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.

[0229] In one or more embodiments, the emission layer may include quantum dots.

[0230] In some embodiments, the emissive layer may include a delayed fluorescent material. The delayed fluorescent material may act as a host or a dopant in the emissive layer.

[0231] In one or more embodiments, in addition to the heterocyclic compound, the emission layer may further include a host, an auxiliary dopant, a sensitizer, a delayed fluorescent material, or any combination thereof. Each of the host, the auxiliary dopant, the sensitizer, the delayed fluorescent material, and any combination thereof may include at least one deuterium.

[0232] For example, in some embodiments, the emission layer may include a heterocyclic compound and a host. The host may be different from the heterocyclic compound, and the host may include an electron transport compound, a hole transport compound, a bipolar compound, or any combination thereof. The host may not include (e.g., may exclude) a metal. The electron transport compound, the hole transport compound, and the bipolar compound are different from each other.

[0233] In one or more embodiments, the emission layer may include a heterocyclic compound and a host, and the host may include an electron transport compound and a hole transport compound.

[0234] In one or more embodiments, the electron transport compound and the hole transport compound may form an exciplex.

[0235] The thickness of the emitter layer can be approximately To about within the range of, for example, about To about When the thickness of the emission layer is within these ranges, excellent or suitable light emitting characteristics may be obtained without significantly increasing the driving voltage.

[0236] main body

[0237] In one or more embodiments, the host may include a compound represented by Formula 301:

[0238] Formula 301

[0239] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .

[0240] In formula 301, Ar301 and L 301 may be independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0241] xb11 can be 1, 2 or 3,

[0242] xb1 can be an integer from 0 to 5.

[0243] R 301 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O) 2 (Q 301 ) or -P(=O)(Q 301 )(Q 302 ),

[0244] xb21 can be an integer from 1 to 5, and

[0245] Q 301 To Q 303 Each of these is related to Q 1Same as described.

[0246] For example, in some embodiments, when xb11 in Formula 301 is 2 or greater, two or more Ar 301 can be connected to each other via a single bond.

[0247] In one or more embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:

[0248] Formula 301-1

[0249]

[0250] Formula 301-2

[0251]

[0252] In Formula 301-1 and Formula 301-2, Ring A 301 To Ring A 304 may be independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0253] X 301 Can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),

[0254] xb22 and xb23 can each independently be 0, 1 or 2,

[0255] L 301 , xb1 and R 301 may each be the same as described herein,

[0256] L 302 To L 304 can be independently compared with the L 301 Same as described,

[0257] xb2 to xb4 may each independently be the same as described herein with respect to xb1, and

[0258] R 302 To R305 and R 311 To R 314 can be compared with the 301 Same as described.

[0259] In one or more embodiments, the host can include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. For example, the host can include a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.

[0260] In one or more embodiments, the host may include at least one selected from Compound H1 to Compound H124, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), 9,10-di(2-naphthyl)-2-tert-butylanthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-di(carbazol-9H-yl)benzene (mCP), 1,3,5-tri(carbazol-9H-yl)benzene (TCP), or any combination thereof:

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267] In one or more embodiments, the host may include a first host compound and a second host compound.

[0268] In one or more embodiments, the first host compound may be a hole transporting host.

[0269] In one or more embodiments, the second host compound may be an electron transporting host.

[0270] In the present disclosure, the term "hole transport host" as used herein refers to a compound including a hole transport moiety.

[0271] In the present disclosure, the term "electron transport host" as used herein refers not only to a compound including an electron transport moiety but also to a compound having a bipolar property.

[0272] The terms "hole transport host" and "electron transport host" can be understood according to the relative difference between the hole mobility and the electron mobility in the hole transport host and the electron transport host, respectively. For example, even when the electron transport host does not include an electron transport moiety, a bipolar compound that exhibits a relatively higher electron mobility than the hole transport host can also be understood as an electron transport host.

[0273] In one or more embodiments, the hole transport host may be represented by one selected from Formula 311-1 to Formula 311-6, and the electron transport host may be represented by one selected from Formula 312-1 to Formula 312-4 and Formula 313:

[0274] Formula 311-1

[0275]

[0276] Formula 311-2

[0277]

[0278] Formula 311-3

[0279]

[0280] Formula 311-4

[0281]

[0282] Formula 311-5

[0283]

[0284] Formula 311-6

[0285]

[0286] Formula 312-1

[0287]

[0288] Formula 312-2

[0289]

[0290] Formula 312-3

[0291]

[0292] Formula 312-4

[0293]

[0294] Formula 313

[0295]

[0296] Formula 313A

[0297]

[0298] Among them, in Formulas 311-1 to 311-6, Formulas 312-1 to 312-4, Formula 313 and Formula 313A,

[0299] Ar 301 It may be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0300] A 301 To A 304 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,

[0301] X 301 Can be O, S, N[(L 304 ) xb4 -R 304 ]、C[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ] or Si[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ],

[0302] X 302 , Y 301 and Y 302 can be independently a single bond, O, S, N[(L 305 ) xb5 -R 305 ]、C[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ]、Si[(L 304 ) xb4 -R304 ][(L 305 ) xb5 -R 305 ] or S(=O) 2 ,

[0303] xb1 to xb5 can be 0, 1, 2, 3, 4 or 5 respectively,

[0304] xb6 can be 1, 2, 3, 4 or 5,

[0305] X 321 To X 328 can be independently N or C[(L 324 ) xb24 -R 324 ],

[0306] Y 321 Can be *-O-*', *-S-*', *-N[(L 325 ) xb25 -R 325 ]-*'、*-C[(L 325 ) xb25 -R 325 ][(L 326 ) xb26 -R 326 ]-*'、*-C[(L 325 ) xb25 -R 325 ]=C[(L 326 ) xb26 -R 326 ]-*'、*-C[(L 325 ) xb25 -R 325 ]=N-*'or*-N=C[(L 326 ) xb26 -R 326 ]-*',

[0307] k21 can be 0, 1 or 2. When k21 is 0, Y 321 does not exist,

[0308] xb21 to xb26 can each independently be 0, 1, 2, 3, 4 or 5,

[0309] A 31 , A 32 and A 34 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 30 Heterocyclic group,

[0310] A33 may be a group represented by formula 313A,

[0311] X 31 It can be N[(L 335 ) xb35 -(R 335 )]、O、S、Se、C[(L 335 ) xb35 -(R 335 )][(L 336 ) xb36 -(R 336 )] or Si[(L 335 ) xb35 -(R 335 )][(L 336 ) xb36 -(R 336 )], xb31 to xb36 may each independently be 0, 1, 2, 3, 4 or 5,

[0312] xb42 to xb44 may each independently be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10,

[0313] L 301 To L 306 , L 321 To L 326 and L 331 To L 336 may be independently a single bond, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 20 Alkylene, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 20 Alkenylene, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 20 Alkyne, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkylene, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkylene, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkenylene, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkenylene, unsubstituted or substituted with at least one R 10a Substituted C6 -C 60 Arylene, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroarylene, unsubstituted or substituted with at least one R 10a A substituted divalent non-aromatic fused polycyclic group, or an unsubstituted or substituted group with at least one R 10a a substituted divalent non-aromatic fused heteropolycyclic group,

[0314] R 301 To R 305 , R 311 To R 314 , R 321 To R 326 and R 331 To R 336 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10a A substituted monovalent non-aromatic fused polycyclic group, unsubstituted or substituted with at least one R 10a Substituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) or -P(=S)(Q 1 )(Q 2 ),

[0315] Selected from R 321 To R 326 Two or more substituents in are optionally bonded together to form an unsubstituted or substituted R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0316] R 10a Can be:

[0317] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0318] C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C60 Alkynyl or C 1 -C 60 Alkoxy, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, -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 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof;

[0319] C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryloxy or C 1 -C 60 heteroarylthio, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C6 -C 60 Arylthio, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, -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 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or

[0320] -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 ) or -P(=O)(Q 31 )(Q 32 ),and

[0321] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; or C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic groups, each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60Alkyl, C 1 -C 60 The present invention is substituted with alkoxy, phenyl, biphenyl or any combination thereof.

[0322] In one or more embodiments, the first host compound and the second host compound may form an exciplex.

[0323] Phosphorescent dopants

[0324] In one or more embodiments, the emission layer may further include a phosphorescent dopant.

[0325] For example, in some embodiments, the emission layer may further include a phosphorescent dopant, and the phosphorescent dopant may function as a sensitizer.

[0326] In one or more embodiments, the phosphorescent dopant may include at least one transition metal as a central metal.

[0327] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.

[0328] The phosphorescent dopant may be electrically neutral.

[0329] In one or more embodiments, the phosphorescent dopant may be an organometallic compound.

[0330] In some embodiments, the phosphorescent dopant may include an organometallic compound represented by Formula 401:

[0331] Formula 401

[0332] M(L 401 ) xc1 (L 402 ) xc2

[0333] Formula 402

[0334]

[0335] Wherein, in Formula 401 and Formula 402, M may be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),

[0336] L 401 may be a ligand represented by formula 402, and xc1 may be 1, 2 or 3, wherein when xc1 is 2 or greater, two or more L 401 can be the same or different from each other,

[0337] L402 may be an organic ligand, and xc2 may be 0, 1, 2, 3 or 4, and when xc2 is 2 or greater, two or more L 402 can be the same or different from each other,

[0338] X 401 and X 402 may each independently be nitrogen or carbon,

[0339] Ring A 401 and Ring A 402 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,

[0340] T 401 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*'、*-C(Q 411 )(Q 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*'or*=C=*',

[0341] X 403 and X 404 can be each independently a chemical bond (e.g., a covalent bond or a coordination bond), O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ),

[0342] Q 411 To Q 414 can be respectively compared with the Q 1 Same as described,

[0343] R 401 and R 402 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 20 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 20 Alkoxy, unsubstituted or substituted with at least one R10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) or -P(=O)(Q 401 )(Q 402 ),

[0344] Q 401 To Q 403 can be respectively compared with the Q 1 Same as described,

[0345] xc11 and xc12 may each independently be an integer from 0 to 10, and

[0346] * and *' in Formula 402 each indicate a binding site with M in Formula 401.

[0347] For example, in some embodiments, in equation 402, i)X 401 may be nitrogen, and X 402 may be carbon; or ii) X 401 and X 402 Each of can be nitrogen.

[0348] In one or more embodiments, when xc1 in equation 401 is 2 or greater, two or more L 401 The two rings A 401 It can be optionally connected via T as a linker 402 bonded to each other, and / or two or more L 401 The two rings A 402 It can be optionally connected via T as a linker 403 Bonded to each other (see Compound PD1 to Compound PD4 and Compound PD7). 402 and T 403 can be respectively compared with the T 401 Same as described.

[0349] L in Formula 401 402 It can be an organic ligand. For example, L402 It may include halogen, diketone group (e.g., acetylacetonate group), carboxylic acid group (e.g., picolinate group), -C(=O), isonitrile group, -CN, phosphorus-containing group (e.g., phosphine group, phosphite group, etc.), or any combination thereof.

[0350] In one or more embodiments, the phosphorescent dopant may be, for example, one selected from Compound PD1 to Compound PD41 or any combination thereof:

[0351]

[0352]

[0353]

[0354] Fluorescent dopants

[0355] In one or more embodiments, the emission layer may further include a fluorescent dopant.

[0356] The fluorescent dopant may include an amine-containing compound (eg, the amine-containing compound of one or more embodiments of the present disclosure), a styryl-containing compound, or any combination thereof.

[0357] For example, in some embodiments, the fluorescent dopant may include a compound represented by Formula 501:

[0358] Formula 501

[0359]

[0360] Wherein, in Formula 501, Ar 501 , L 501 To L 503 , R 501 and R 502 may be independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0361] xd1 to xd3 may each independently be 0, 1, 2 or 3, and

[0362] xd4 can be 1, 2, 3, 4, 5 or 6.

[0363] For example, in some embodiments, Ar in Formula 501 501It may be a fused cyclic group in which three or more monocyclic groups are fused together (e.g., anthracenyl, yl or pyrene).

[0364] In one or more embodiments, xd4 in equation 501 may be 2.

[0365] For example, in one or more embodiments, the fluorescent dopant may include: at least one selected from the group consisting of Compound FD1 to Compound FD36; 4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl (DPVBi); 4,4'-bis[4-(N,N-diphenylamino)phenylvinyl]biphenyl (DPAVBi); or any combination thereof:

[0366]

[0367]

[0368]

[0369] Delayed fluorescence material

[0370] In one or more embodiments, the emission layer may further include a delayed fluorescent material.

[0371] In the present disclosure, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.

[0372] The delayed fluorescent material included in the emission layer may serve as a host or a dopant according to the types or kinds of other materials included in the emission layer.

[0373] In one or more embodiments, the difference between the triplet energy level of the delayed fluorescent material and the singlet energy level of the delayed fluorescent material may be about 0 eV to about 0.5 eV. When the difference between the triplet energy level of the delayed fluorescent material and the singlet energy level of the delayed fluorescent material satisfies the above range, up-conversion from the triplet state of the delayed fluorescent material to the singlet state may effectively occur, and thus, the organic light-emitting device 10 may have improved luminous efficiency.

[0374] For example, in one or more embodiments, the delayed fluorescent material may include: i) at least one electron donor (eg, a π-electron-rich C 3 -C 60 A cyclic group such as a carbazolyl group) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group, or a π-electron-deficient nitrogen-containing C 1 -C 60 and / or ii) a material comprising two or more cyclic groups fused together while sharing boron (B) 8 -C 60Polycyclic materials.

[0375] Non-limiting examples of the delayed fluorescent material may include at least one selected from Compound DF1 to Compound DF9:

[0376]

[0377] quantum dots

[0378] In one or more embodiments, the emission layer may include quantum dots.

[0379] The term "quantum dot" as used herein refers to a crystal of a semiconductor compound, and may include any material capable of emitting light at one or more suitable emission wavelengths depending on the size of the crystal.

[0380] The diameter of the quantum dot can be, for example, in the range of about 1 nm to about 10 nm. In the present disclosure, when a point, a plurality of points or a point particle is spherical, "diameter" indicates the particle diameter or the average particle diameter, and when the particle is non-spherical, "diameter" indicates the major axis length or the average major axis length. The diameter of the particle can be measured using a scanning electron microscope or a particle size analyzer. As a particle size analyzer, for example, HORIBA's LA-950 laser particle size analyzer can be used. When the size of the particle is measured using a particle size analyzer, the average particle diameter is referred to as D50. D50 refers to the average diameter of the particles whose cumulative volume corresponds to 50 vol% in the particle size distribution (e.g., cumulative distribution), and refers to the value of the particle size corresponding to 50% from the smallest particle when the total number of particles is 100% in the distribution curve accumulated in the order of the smallest particle size to the largest particle size.

[0381] Quantum dots can be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.

[0382] The wet chemical process is a method that includes mixing the precursor material of the quantum dot with an organic solvent and then growing the quantum dot particle crystal. When the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal, so that the growth of the quantum dot particles can be controlled or selected by a process that is less expensive and easier than vapor deposition methods such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).

[0383] Quantum dots may include Group II-VI semiconductor compounds, Group III-V semiconductor compounds, Group III-VI semiconductor compounds, Group I-III-VI semiconductor compounds, Group IV-VI semiconductor compounds, Group IV elements or compounds, or any combination thereof.

[0384] Non-limiting examples of II-VI semiconductor compounds may be binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe and / or MgS; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, Cd ZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe and / or MgZnS; quaternary compounds such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and / or HgZnSTe; or any combination thereof.

[0385] Non-limiting examples of III-V semiconductor compounds may include binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, and / or InSb; ternary compounds such as GaNPs, GaNAs, GaNSb, GaPAs, GaPSb, AlNPs, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, and / or InPSb; quaternary compounds such as GaAlNPs, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNPs, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNPs, InAlNAs, InAlNSb, InAlPAs, and / or InAlPSb; or any combination thereof. In some embodiments, the III-V semiconductor compounds may also include Group II elements. Non-limiting examples of the Group III-V semiconductor compound further including a Group II element may be InZnP, InGaZnP, InAlZnP, and the like.

[0386] Non-limiting examples of III-VI semiconductor compounds may be: binary compounds such as GaS, GaSe, Ga 2 Se 3 、GaTe、InS、InSe、In 2 S 3 、In 2 Se 3 and / or InTe; ternary compounds such as InGaS 3 or InGaSe 3; or any combination thereof.

[0387] Non-limiting examples of Group I-III-VI semiconductor compounds may be: ternary compounds such as AgInS, AgInS 2 、CuInS、CuInS 2 、CuGaO 2 、AgGaO 2 and / or AgAlO 2 ; or any combination thereof.

[0388] Non-limiting examples of Group IV-VI semiconductor compounds may be: binary compounds such as SnS, SnSe, SnTe, PbS, PbSe and / or PbTe; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe and / or SnPbTe; quaternary compounds such as SnPbSSe, SnPbSeTe and / or SnPbSTe; or any combination thereof.

[0389] The Group IV elements or compounds may include: single elements, such as Si or Ge; binary compounds, such as SiC or SiGe; or any combination thereof.

[0390] Each element included in the multi-element compound such as the binary compound, the ternary compound, and the quaternary compound may be present in the particle at a substantially uniform concentration or a non-substantially uniform concentration.

[0391] In some embodiments, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is substantially uniform or a core-shell dual structure. For example, the material included in the core and the material included in the shell may be different from each other.

[0392] The shell of a quantum dot can act as a protective layer to prevent chemical degradation of the core to maintain semiconductor properties, and / or act as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient, where the concentration of the element present in the shell decreases toward the center of the core.

[0393] Examples of the shell of a quantum dot may be an oxide of a metal, a metalloid or a non-metal, a semiconductor compound, or any combination thereof. Non-limiting examples of an oxide of a metal, a metalloid or a non-metal may be: a binary compound such as SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3 , Mn 3 O4 , CuO, FeO, Fe 2 O 3 , Fe 3 O 4 , CoO, Co 3 O 4 and / or NiO; ternary compounds such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 and / or CoMn 2 O 4 ; and any combination thereof. As described herein, examples of semiconductor compounds may be: II-VI semiconductor compounds; III-V semiconductor compounds; III-VI semiconductor compounds; I-III-VI semiconductor compounds; IV-VI semiconductor compounds; and any combination thereof. For example, semiconductor compounds suitable as shells may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.

[0394] The full width at half maximum (FWHM) of the emission spectrum of the quantum dot can be about 45nm or less, such as about 40nm or less, such as about 30nm or less, and within these ranges, the color purity or color reproducibility of the quantum dot can be improved. In some embodiments, because the light emitted by the quantum dot is emitted in all directions, the wide viewing angle can be improved.

[0395] In one or more embodiments, the quantum dots may be in the form of spherical nanoparticles, pyramidal nanoparticles, multi-armed nanoparticles, cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplates.

[0396] Because the energy band gap of quantum dots can be adjusted by controlling the size of quantum dots, light having one or more suitable wavelength bands can be obtained from the quantum dot emission layer. Therefore, by utilizing quantum dots of different sizes, an organic light-emitting device that emits light of one or more suitable wavelengths can be realized. In one or more embodiments, the size of the quantum dots can be selected so that the quantum dots can emit red light, green light, and / or blue light. In some embodiments, quantum dots having a suitable size can be configured to emit white light through a combination of one or more suitable colors of light.

[0397] Electron transport region in the intermediate layer 130

[0398] The electron transport region may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material; ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of different materials; or iii) a multilayer structure including a plurality of layers including different materials.

[0399] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0400] For example, in one or more embodiments, 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, the constituent layers of each structure being stacked sequentially from the emission layer in the order stated.

[0401] In one or more embodiments, the electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π-electron-deficient nitrogen-containing C 1 -C 60 Cyclic base.

[0402] For example, in some embodiments, the electron transport region may include a compound represented by Formula 601:

[0403] Formula 601

[0404] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 ,

[0405] Wherein, in Formula 601, Ar 601 and L 601 may be independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0406] xe11 can be 1, 2 or 3,

[0407] xe1 can be 0, 1, 2, 3, 4, or 5,

[0408] R 601 It may be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O) 2 (Q 601 ) or -P(=O)(Q 601 )(Q 602 ),

[0409] Q 601 To Q 603 can be respectively compared with the Q 1 Same as described,

[0410] xe21 can be 1, 2, 3, 4 or 5,

[0411] Selected from Ar 601 , L 601 and R 601 At least one of them may be independently unsubstituted or substituted by at least one R 10a Substituted π-electron-deficient nitrogen-containing C 1 -C 60 Cyclic base.

[0412] For example, when xe11 in Formula 601 is 2 or greater, two or more Ar 601 can be connected to each other via a single bond.

[0413] In some embodiments, Ar in Formula 601 601 may be unsubstituted or substituted with at least one R 10a Substituted anthracenyl.

[0414] In some embodiments, the electron transport region may include a compound represented by Formula 601-1:

[0415] Formula 601-1

[0416]

[0417] Among them, in formula 601-1, X 614 Can be N or C (R 614 ), X 615Can be N or C (R 615 ), X 616 Can be N or C (R 616 ), and selected from X 614 To X 616 At least one of them can be N,

[0418] L 611 To L 613 can be respectively compared with the L 601 Same as described,

[0419] xe611 to xe613 may each be the same as described herein with respect to xe1,

[0420] R 611 To R 613 can be compared with the 601 Same as described, and

[0421] R 614 To R 616 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.

[0422] For example, in some embodiments, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 may each independently be 0, 1, or 2.

[0423] In one or more embodiments, the electron transport region may include at least one selected from the group consisting of Compound ET1 to Compound ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), tris(8-hydroxyquinoline)aluminum (Alq 3 ), bis(2-methyl-8-hydroxyquinoline-N1,08)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), or any combination thereof:

[0424]

[0425]

[0426]

[0427] The thickness of the electron transport region can be approximately To about within the range of, for example, about To about When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may be about To about within the range of, for example, about To about and the thickness of the electron transport layer can be in the range of about To about within the range of, for example, about To about When the thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer and / or the electron transport region is within these ranges, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.

[0428] In one or more embodiments, the electron transport region (eg, the electron transport layer in the electron transport region) may further include a metal-containing material in addition to the above-mentioned materials.

[0429] The metal-containing material can include alkali metal complex, alkaline earth metal complex or any combination thereof. The metal ion of the alkali metal complex can be Li ion, Na ion, K ion, Rb ion or Cs ion, and the metal ion of the alkaline earth metal complex can be Be ion, Mg ion, Ca ion, Sr ion or Ba ion. The ligand coordinated with the metal ion of the alkali metal complex or the metal ion of the alkaline earth metal complex can include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.

[0430] For example, in some embodiments, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (Liq) or compound ET-D2:

[0431]

[0432] In one or more embodiments, the electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 150. The electron injection layer may be in direct contact with the second electrode 150.

[0433] The electron injection layer may have: i) a single-layer structure including a single layer (e.g., consisting of a single layer) that includes a single material (e.g., consisting of a single material); ii) a single-layer structure including a single layer (e.g., consisting of a single layer) that includes a plurality of different materials (e.g., consisting of a plurality of different materials); or iii) a multi-layer structure including a plurality of layers that include different materials.

[0434] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, a compound containing an alkali metal, a compound containing an alkaline earth metal, a compound containing a rare earth metal, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0435] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.

[0436] The compound containing an alkali metal, the compound containing an alkaline earth metal, and the compound containing a rare earth metal may be oxides, halides (e.g., fluorides, chlorides, bromides, or iodides), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, respectively, or any combination thereof.

[0437] The compound containing an alkali metal may include: alkali metal oxides such as Li 2 O, Cs 2 O, and / or K 2 O; alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and / or KI, etc.; or any combination thereof. The compound containing an alkaline earth metal may include alkaline earth metal compounds such as BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying the condition 0 < x < 1) and / or Ba x Ca 1-x O (where x is a real number satisfying the condition 0 < x < 1), etc. The compound containing a rare earth metal may include YbF 3 、ScF 3 、Sc 2 O 3 、Y 2 O 3 、Ce 2 O 3 、GdF3 , TbF 3 ,YbI 3 ScI 3 , TbI 3 Or any combination thereof. In one or more embodiments, the rare earth metal-containing compound may include a lanthanide metal telluride. Non-limiting examples of lanthanide metal tellurides may be LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, LaTe, 2 Te 3 、Ce 2 Te 3 , Pr 2 Te 3 、Nd 2 Te 3 、Pm 2 Te 3 、Sm 2 Te 3 、Eu 2 Te 3 、Gd2Te 3 , Tb 2 Te 3 、Dy 2 Te 3 、Ho 2 Te 3 , Er 2 Te 3 、Tm 2 Te 3 , Yb 2 Te 3 and / or Lu 2 Te 3 .

[0438] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may include: i) one of the metal ions of the alkali metal, one of the metal ions of the alkaline earth metal and one of the metal ions of the rare earth metal; and ii) a ligand bonded to the metal ion (i.e., the corresponding metal ion), such as hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.

[0439] In one or more embodiments, the electron injection layer may include (e.g., be composed of) an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described above. In one or more embodiments, the electron injection layer may also include an organic material (e.g., a compound represented by Formula 601).

[0440] In one or more embodiments, the electron injection layer may include (e.g., consist of): i) a compound containing an alkali metal (e.g., an alkali metal halide); or ii) a) a compound containing an alkali metal (e.g., an alkali metal halide) and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, in some embodiments, the electron injection layer may be a KI:Yb co-deposition layer, a RbI:Yb co-deposition layer, and / or a LiF:Yb co-deposition layer, etc.

[0441] When the electron injection layer also includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof can be substantially uniformly or non-uniformly dispersed in a matrix including the organic material.

[0442] The thickness of the electron injection layer can be about To about within the range of, for example, about To about When the thickness of the electron injection layer is within the above range, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.

[0443] The second electrode 150

[0444] The second electrode 150 may be on the intermediate layer 130 having the structure described above. The second electrode 150 may be a cathode as an electron injection electrode, and as a material for the second electrode 150, metals, alloys, conductive compounds, or any combination thereof each having a low work function may be used.

[0445] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0446] The second electrode 150 may have a single-layer structure or a multi-layer structure including a plurality of layers.

[0447] Covering

[0448] The first covering layer may be located outside the first electrode 110 (e.g., on the first electrode 110), and / or the second covering layer may be located outside the second electrode 150 (e.g., on the second electrode 150). In one or more embodiments, the organic light emitting device 10 may have a structure in which the first covering layer, the first electrode 110, the intermediate layer 130, the second electrode 150 are sequentially stacked in the stated order, a structure in which the first electrode 110, the intermediate layer 130, the second electrode 150, and the second covering layer are sequentially stacked in the stated order, or a structure in which the first covering layer, the first electrode 110, the intermediate layer 130, the second electrode 150, and the second covering layer are sequentially stacked in the stated order.

[0449] Light generated in the emission layer of the intermediate layer 130 of the organic light-emitting device 10 can be emitted toward the outside through the first electrode 110 as a semi-transmissive electrode or a transmissive electrode and the first covering layer, and light generated in the emission layer of the intermediate layer 130 of the organic light-emitting device 10 can be emitted toward the outside through the second electrode 150 as a semi-transmissive electrode or a transmissive electrode and the second covering layer.

[0450] According to the principle of constructive interference, the first cover layer and the second cover layer can improve the external emission efficiency, thereby improving the light emission efficiency of the organic light emitting device 10 and thus improving the light emission efficiency of the organic light emitting device 10.

[0451] Each of the first cover layer and the second cover layer may include a material having a refractive index of 1.6 or greater (eg, at 589 nm).

[0452] The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.

[0453] At least one of the first covering layer and the second covering layer may (for example, the first covering layer and the second covering layer may each independently) include a carbocyclic compound, a heterocyclic compound, an amine-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. Optionally, the carbocyclic compound, the heterocyclic compound, and the amine-containing compound may each be substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In one or more embodiments, at least one of the first covering layer and the second covering layer may (for example, the first covering layer and the second covering layer may each independently) include an amine-containing compound, for example, the amine-containing compound of one or more embodiments of the present disclosure.

[0454] For example, in one or more embodiments, at least one of the first covering layer and the second covering layer may (eg, the first covering layer and the second covering layer may each independently) include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.

[0455] In one or more embodiments, at least one of the first cover layer and the second cover layer may (for example, the first cover layer and the second cover layer may each independently) include at least one selected from compounds HT28 to HT33, at least one selected from compounds CP1 to CP6, β-NPB, or any combination thereof:

[0456]

[0457] membrane

[0458] The amine-containing compound represented by Formula 1 may be included in one or more suitable films. Therefore, one or more aspects of the embodiments of the present disclosure relate to a film comprising an amine-containing compound represented by Formula 1. The film may be, for example, an optical member (or light control element) (e.g., a color filter, a color conversion member, a cover layer, a light extraction efficiency enhancement layer, a selective light absorption layer, a polarization layer, and / or a layer containing quantum dots, etc.), a light blocking member (e.g., a light reflecting layer and / or a light absorbing layer, etc.), and / or a protective member (e.g., an insulating layer and / or a dielectric layer, etc.).

[0459] Electronic devices

[0460] Organic light emitting devices (e.g. Figure 1 The organic light emitting device 10 in the embodiment may be included in one or more suitable electronic devices. In one or more embodiments, the electronic device including the organic light emitting device may be a light emitting device and / or an authentication device, etc.

[0461] In one or more embodiments, in addition to the organic light-emitting device, the electronic device (e.g., a light-emitting device) may further include i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and / or the color conversion layer may be arranged in at least one direction of travel of the light emitted from the organic light-emitting device. For example, in some embodiments, the light emitted from the organic light-emitting device may be blue light or white light (e.g., combined white light). The organic light-emitting device may be the same as described above. In one or more embodiments, the color conversion layer may include quantum dots. The quantum dots may be, for example, the quantum dots described herein.

[0462] The electronic device may include a first substrate. The first substrate may include a plurality of sub-pixel areas, the color filter may include a plurality of color filter areas respectively corresponding to the sub-pixel areas, and the color conversion layer may include a plurality of color conversion areas respectively corresponding to the sub-pixel areas.

[0463] A pixel defining film may be located between the sub-pixel regions to define each sub-pixel region.

[0464] The color filter may further include a plurality of color filter areas and a light shielding pattern between the color filter areas, and the color conversion layer may further include a plurality of color conversion areas and a light shielding pattern between the color conversion areas.

[0465] A plurality of color filter regions (or a plurality of color conversion regions) may include a first region configured to emit a first color light, a second region configured to emit a second color light, and / or a third region configured to emit a third color light, wherein the first color light, the second color light, and / or the third color light may have different maximum emission wavelengths from each other. For example, in one or more embodiments, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, in one or more embodiments, a plurality of color filter regions (or a plurality of color conversion regions) may include quantum dots. In some embodiments, the first region may include red quantum dots to emit red light, the second region may include green quantum dots to emit green light, and the third region may not include (e.g., may exclude) quantum dots. For details of quantum dots, reference may be made to the relevant description provided herein. The first region, the second region, and / or the third region may each include a scatterer.

[0466] For example, in one or more embodiments, the organic light emitting device may emit a first light, the first region may absorb the first light to emit a first-first color light, the second region may absorb the first light to emit a second-first color light, and the third region may absorb the first light to emit a third-first color light. In this regard, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. In some embodiments, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.

[0467] In one or more embodiments, in addition to the organic light-emitting device described above, the electronic device may further include a thin film transistor. The thin film transistor may include a source electrode, a drain electrode, and an active layer, wherein one selected from the source electrode and the drain electrode may be electrically connected to the first electrode or the second electrode of the organic light-emitting device.

[0468] The thin film transistor may further include a gate electrode and / or a gate insulating film, etc.

[0469] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, and / or an oxide semiconductor, etc.

[0470] In one or more embodiments, the electronic device may further include a sealing portion for sealing the organic light-emitting device. The sealing portion may be arranged between the color filter and / or the color conversion layer and the organic light-emitting device. The sealing portion allows light from the organic light-emitting device to be emitted to the outside while concurrently (e.g., simultaneously) preventing or reducing ambient air and moisture from penetrating into the organic light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer including at least one of an organic layer and an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.

[0471] Depending on the purpose of the electronic device, in addition to the color filter and / or color conversion layer, various functional layers may be additionally located on the sealing portion. The functional layer may include a touch screen layer and / or a polarization layer, etc. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer.

[0472] In addition to the organic light emitting device, the authentication device may further include a biometric information collector. The authentication device may be, for example, a biometric authentication device that authenticates an individual by utilizing biometric information of a living body (eg, fingertips, pupils, etc.).

[0473] The electronic device can be applied to one or more of a display, a light source, a lighting equipment, a personal computer (e.g., a mobile personal computer), a mobile phone, a digital camera, an electronic organizer, an electronic dictionary, an electronic game console, a medical instrument (e.g., an electronic thermometer, a blood pressure meter, a blood glucose meter, a pulse measuring device, a pulse wave measuring device, an electrocardiogram display, an ultrasonic diagnostic device, or an endoscope display), a fish finder, one or more suitable measuring instruments, meters (e.g., meters for vehicles, aircraft, and ships), and a projector, etc.

[0474] Electronic equipment

[0475] The organic light emitting device may be included in one or more suitable electronic equipment.

[0476] For example, electronic equipment including an organic light-emitting device can be at least one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, a light for indoor or outdoor lighting and / or signaling, a head-up display, a fully or partially transparent display, a flexible display (such as a rollable display, a foldable display, or a stretchable display), a laser printer, a phone (such as a mobile phone or a tablet phone), a tablet computer, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a 3D display, a virtual or augmented reality display, a vehicle, a video wall including multiple displays stitched together, a theater or stadium screen, a light therapy device, and a billboard.

[0477] The organic light emitting device may have excellent or suitable effects in terms of light emitting efficiency and long lifespan, and thus, electronic equipment including the organic light emitting device may have desired characteristics such as high brightness, high resolution, and low power consumption.

[0478] Figure 2 and Figure 3 Description

[0479] Figure 2 is a schematic cross-sectional view illustrating a structure of a light emitting device according to one or more embodiments of the present disclosure.

[0480] Figure 2 The light emitting device may include a substrate 100, a thin film transistor (TFT), an organic light emitting device (eg, Figure 1 An organic light emitting device 10) and a packaging portion 300 that seals the organic light emitting device.

[0481] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. The buffer layer 210 may be on the substrate 100. The buffer layer 210 may prevent or reduce impurities from penetrating the substrate 100, and may provide a flat surface on the substrate 100.

[0482] The TFT may be on the buffer layer 210 . The TFT may include an active layer 220 , a gate electrode 240 , a source electrode 260 , and a drain electrode 270 .

[0483] The active layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.

[0484] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be on the active layer 220 , and the gate electrode 240 may be on the gate insulating film 230 .

[0485] An interlayer insulating film 250 may be on the gate electrode 240. The interlayer insulating film 250 may be located between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to be insulated from each other.

[0486] The source electrode 260 and the drain electrode 270 may be on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may be positioned to contact the exposed portions of the source region and the drain region of the active layer 220, respectively.

[0487] The TFT may be electrically connected to the organic light emitting device to drive the organic light emitting device, and may be covered and protected by the passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The organic light emitting device may include a first electrode 110, an intermediate layer 130, and a second electrode 150.

[0488] The first electrode 110 may be on the passivation layer 280. The passivation layer 280 may be positioned to expose a portion of the drain electrode 270 without completely covering the drain electrode 270, and the first electrode 110 may be positioned to be connected to the exposed portion of the drain electrode 270.

[0489] A pixel defining layer 290 including an insulating material may be on the first electrode 110. The pixel defining layer 290 may expose a specific region of the first electrode 110, and the intermediate layer 130 may be formed in the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide or polyacrylic organic film. In some embodiments, at least some layers of the intermediate layer 130 may extend beyond the upper portion of the pixel defining layer 290, thereby being positioned in the form of a common layer.

[0490] The second electrode 150 may be on the intermediate layer 130, and the capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.

[0491] The encapsulation part 300 may be on the cover layer 170. The encapsulation part 300 may be arranged on the organic light emitting device to protect the organic light emitting device from moisture and / or oxygen. The encapsulation part 300 may include: an inorganic film including silicon nitride (SiN x ), silicon oxide (SiO x ), indium tin oxide, indium zinc oxide or any combination thereof; organic films including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resins (e.g., polymethyl methacrylate and / or polyacrylic acid, etc.), epoxy resins (e.g., aliphatic glycidyl ether (AGE), etc.) or any combination thereof; or any combination of inorganic films and organic films.

[0492] Figure 3 is a schematic cross-sectional view illustrating a structure of a light emitting device according to one or more embodiments of the present disclosure.

[0493] In addition to the light shielding pattern 500 and the functional region 400 being additionally located on the encapsulation portion 300, Figure 3 Light emitting devices and Figure 2 The functional area 400 may be i) a color filter area, ii) a color conversion area, or iii) a combination of a color filter area and a color conversion area. In one or more embodiments, the functional area 400 may be i) a color filter area, ii) a color conversion area, or iii) a combination of a color filter area and a color conversion area. Figure 3 The organic light-emitting device in the light-emitting apparatus may be a tandem organic light-emitting device.

[0494] Figure 4 Description

[0495] Figure 4 The organic light emitting device 10 (see Figure 1) is a schematic perspective view of an electronic equipment 1 of the present invention. As a device for displaying moving images or still images, the electronic equipment 1 can be a portable electronic equipment such as a mobile phone, a smart phone, a tablet personal computer (PC), a mobile communication terminal, an electronic notebook, an e-book, a portable multimedia player (PMP), a navigation or ultra-mobile PC (UMPC), and one or more suitable electronic products such as a television, a laptop computer, a monitor, a billboard or an Internet of Things (IoT) device. The electronic equipment 1 can be such a product or a part thereof. In some embodiments, the electronic equipment 1 can be a wearable device such as a smart watch, a watch phone, a display of a glasses type or kind, or a head-mounted display (HMD), or a part of a wearable device. However, the embodiments of the present disclosure are not limited thereto. For example, in one or more embodiments, the electronic equipment 1 may include a dashboard of a vehicle, a central control panel of a vehicle, a central information display arranged on the dashboard of a vehicle, an interior mirror display replacing a side mirror of a vehicle, an entertainment display for a rear seat of a vehicle or a display arranged behind its front seat, or a head-up display (HUD) and / or a computer-generated hologram augmented reality head-up display (CGH AR HUD) installed at the front of the vehicle or projected on the front windshield. For ease of explanation, Figure 4 An embodiment is shown in which the electronic equipment 1 is a smartphone.

[0496] The electronic equipment 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device of the electronic equipment 1 may realize an image through an array of a plurality of pixels two-dimensionally arranged in the display area DA.

[0497] The non-display area NDA is an area where no image is displayed, and may completely surround the display area DA. In the non-display area NDA, a driver for providing an electrical signal or power to a display device arranged in the display area DA may be arranged. In the non-display area NDA, a pad, which is an area to which an electronic component or a printed circuit board may be electrically connected, may be arranged.

[0498] In the electronic equipment 1, the length in the x-axis direction and the length in the y-axis direction may be different from each other. Figure 4 As shown in , the length in the x-axis direction may be shorter than the length in the y-axis direction (the length in the x-axis direction may be the width and shorter than the length in the y-axis direction). In one or more embodiments, the length in the x-axis direction may be substantially the same as the length in the y-axis direction. In one or more embodiments, the length in the x-axis direction may be longer than the length (width) in the y-axis direction.

[0499] Figure 5 and FIG. 6A to FIG. 6C Description

[0500] Figure 5 FIG. 1 is a diagram showing an organic light emitting device 10 (see FIG. 1 ) according to one or more embodiments of the present disclosure. Figure 1 ) is a schematic diagram of the exterior of vehicle 1000 equipped with electronic equipment. FIG. 6A to FIG. 6C Each is a schematic diagram of the interior of a vehicle 1000 according to one or more embodiments of the present disclosure.

[0501] refer to Figure 5 , Fig. 6A , Figure 6B and Figure 6C The vehicle 1000 may refer to one or more suitable devices for moving an object to be transported, such as a person, an object, or an animal, from a starting point to a destination. The vehicle 1000 may include a vehicle traveling on a road or track, a ship moving on an ocean or a river, and / or an airplane flying in the sky using the action of air.

[0502] In one or more embodiments, the vehicle 1000 may travel on a road or track. The vehicle 1000 may move in a set or predetermined direction according to the rotation of at least one of its wheels. For example, the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover, a bicycle, or a train running on a track.

[0503] The vehicle 1000 may include a body having an interior and an exterior and a chassis in which mechanical equipment required for driving is installed as other components in addition to the body. The exterior of the body may include a front panel, a hood, a roof panel, a rear panel, a trunk, and / or a column provided at a boundary between doors, etc. The chassis of the vehicle 1000 may include a power generation device, a power transmission device, a drive device, a steering device, a brake device, a suspension device, a transmission device, a fuel device, and / or front and rear wheels, left and right wheels, etc.

[0504] The vehicle 1000 may include side windows 1100 , a front window 1200 , side mirrors 1300 , a cluster 1400 , a central instrument panel 1500 , a passenger seat instrument panel 1600 , and a display device 2 .

[0505] The side window glass 1100 and the front window glass 1200 may be separated by pillars disposed between the side window glass 1100 and the front window glass 1200 .

[0506] The side window glass 1100 may be mounted on a side of the vehicle 1000. In some embodiments, the side window glass 1100 may be mounted on a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided, and the plurality of side window glasses 1100 may face each other. In some embodiments, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In some embodiments, the first side window glass 1110 may be arranged adjacent to the cluster 1400. The second side window glass 1120 may be arranged adjacent to the passenger seat instrument panel 1600.

[0507] In one or more embodiments, the side window glass 1100 may be spaced apart from each other in the x-axis direction or the -x-axis direction (the direction opposite to the x-direction). For example, in some embodiments, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the x-axis direction or the -x-axis direction. In other words, the imaginary straight line L connecting the side window glass 1100 may extend in the x-axis direction or the -x-axis direction. For example, the imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 may extend in the x-axis direction or the -x-axis direction.

[0508] The front window glass 1200 may be installed at the front of the vehicle 1000. The front window glass 1200 may be disposed between the side window glasses 1100 facing each other.

[0509] The side view mirror 1300 can provide a rear view of the vehicle 1000. The side view mirror 1300 can be installed on the outside of the vehicle body. In some embodiments, a plurality of side view mirrors 1300 can be provided. Any one of the plurality of side view mirrors 1300 can be arranged outside the first side window glass 1110. Another one of the plurality of side view mirrors 1300 can be arranged outside the second side window glass 1120.

[0510] Cluster 1400 may be arranged in front of the steering wheel. Cluster 1400 may include a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge turn indicator, a high beam indicator, warning lights, a seat belt warning light, an odometer, a speedometer, an automatic shift selector indicator, a door open warning light, an engine oil warning light, and / or a low fuel warning light.

[0511] The center instrument panel 1500 may include a control panel on which a plurality of buttons for adjusting an audio device, an air conditioning device, and / or a heater of a seat are disposed. The center instrument panel 1500 may be disposed at one side of the cluster 1400 .

[0512] The passenger seat instrument panel 1600 may be spaced apart from the cluster 1400, with the center console instrument panel 1500 disposed therebetween. In some embodiments, the cluster 1400 may be disposed to correspond to the driver's seat, and the passenger seat instrument panel 1600 may be disposed to correspond to the passenger seat. In some embodiments, the cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat instrument panel 1600 may be adjacent to the second side window glass 1120.

[0513] In one or more embodiments, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be arranged inside the vehicle 1000. In some embodiments, the display device 2 may be arranged between side window glasses 1100 facing each other. The display device 2 may be arranged on at least one of the cluster 1400, the central control instrument panel 1500, and the passenger seat instrument panel 1600.

[0514] The display device 2 may include an organic light-emitting display device, an inorganic EL display device, and / or a quantum dot display device, etc. In the following, as a display device 2 according to one or more embodiments of the present disclosure, an organic light-emitting display device including an organic light-emitting device according to the present disclosure will be described as an example, but one or more suitable types (kinds) of display devices described above may be used in the embodiments of the present disclosure.

[0515] refer to Fig. 6A In one or more embodiments, the display device 2 may be arranged on the central control instrument panel 1500. In some embodiments, the display device 2 may display navigation information. In some embodiments, the display device 2 may display audio, video, or information about vehicle settings.

[0516] refer to Figure 6B In one or more embodiments, the display device 2 may be arranged on the cluster 1400. When the display device 2 is arranged on the cluster 1400, the cluster 1400 may display driving information and the like through the display device 2. For example, the cluster 1400 may be implemented digitally. The cluster 1400 may display vehicle information and driving information as images. For example, the needle and instrument of the tachometer and one or more suitable warning light icons may be displayed through digital signals.

[0517] refer to Figure 6CIn one or more embodiments, the display device 2 may be arranged on the passenger seat instrument panel 1600. The display device 2 may be embedded in the passenger seat instrument panel 1600 or arranged on the passenger seat instrument panel 1600. In some embodiments, the display device 2 arranged on the passenger seat instrument panel 1600 may display images related to the information displayed on the cluster 1400 and / or the information displayed on the central control instrument panel 1500. In one or more embodiments, the display device 2 arranged on the passenger seat instrument panel 1600 may display information different from the information displayed on the cluster 1400 and / or the information displayed on the central control instrument panel 1500.

[0518] Manufacturing method

[0519] The various layers included in the hole transport region, the emission layer, and the various layers included in the electron transport region can each be formed in a specific region by utilizing 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.

[0520] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are each formed by vacuum deposition, the deposition temperature may be within a range of about 100° C. to about 500° C. ... -8 Up to about 10 -3 Torr vacuum and at about To about The deposition is performed at a deposition rate of .

[0521] Definition of terms

[0522] As used herein, the term "C 3 -C 60 "Carbocyclyl" refers to a cyclic group that includes (e.g., consists of) only carbon as a ring-forming atom and has 3 to 60 carbon atoms, and the term "C 1 -C 60 The term "heterocyclic group" refers to a cyclic group having 1 to 60 carbon atoms and having a hetero atom as a ring-forming atom in addition to carbon. 3 -C 60 Carbocyclic and C 1 -C 60 The heterocyclic groups may each be a monocyclic group including one (eg, only one) ring (eg, consisting of one (eg, only one) ring), or a polycyclic group in which two or more rings are fused to each other. 1 -C 60 The heterocyclic group has 3 to 61 ring-forming atoms.

[0523] As used herein, the term "cyclic group" may include C 3 -C 60 Carbocyclic and C 1 -C 60 Heterocyclic group.

[0524] As used herein, the term "π-electron-rich C 3 -C 60 The term "cyclic group" refers to a cyclic group having 3 to 60 carbon atoms and not including *-N=*' as a ring-forming part, and the term "π-electron-deficient nitrogen-containing C 1 -C 60 The term "cyclic group" refers to a heterocyclic group having 1 to 60 carbon atoms and including *-N=*' as a ring-constituting part.

[0525] For example, C 3 -C 60 The carbocyclic group may be: i) a group T1; or ii) a fused cyclic group in which two or more groups T1 are fused to each other (e.g., cyclopentadienyl, adamantyl, norbornyl, phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, phenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, indenophenanthrenyl or indenoanthryl),

[0526] C 1 -C 60The heterocyclic group may be: i) a group T2; ii) a fused cyclic group in which two or more groups T2 are fused to each other; or iii) a fused cyclic group in which at least one group T2 and at least one group T1 are fused to each other (e.g., a pyrrolyl group, a thienyl group, a furyl group, an indolyl group, a benzindolyl group, a naphthoindolyl group, an isoindolyl group, a benzisoindolyl group, a naphthoisoindolyl group, a benzothiorolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzothiorolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an indenocarbazolyl group, an indolcarbazolyl group, a benzofuranocarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiorolocarbazolyl group, a benzoindolcarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthothiorolyl group, a benzofuranodibenzofuranyl group, benzofuranodibenzothienyl, benzothiophenodibenzothienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl , benzoquinolyl, benzisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazine, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiazolyl, azadibenzothiopheneyl, azadibenzofuranyl, etc.),

[0527] Pi-electron-rich C 3 -C 60 The cyclic group may be: i) a group T1; ii) a fused cyclic group in which two or more groups T1 are fused to each other; iii) a group T3; iv) a fused cyclic group in which two or more groups T3 are fused to each other; or v) a fused cyclic group in which at least one group T3 and at least one group T1 are fused to each other (e.g., C 3 -C 60 carbocyclic group, 1H-pyrrolyl, thiolyl, borocyclopentyl, 2H-pyrrolyl, 3H-pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiolyl, dibenzothiophenyl, dibenzofuranyl, indenocarbazolyl, indolcarbazolyl, benzofuranocarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzoindolcarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, benzonaphthothiolyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl, benzothiophenyldibenzothiophenyl, etc.),

[0528] π-electron-deficient nitrogen-containing C1 -C 60 The cyclic group may be: i) a group T4; ii) a fused cyclic group in which two or more groups T4 are fused to each other; iii) a fused cyclic group in which at least one group T4 and at least one group T1 are fused to each other; iv) a fused cyclic group in which at least one group T4 and at least one group T3 are fused to each other; or v) a fused cyclic group in which at least one group T4, at least one group T1 and at least one group T3 are fused to each other (e.g., pyrazolyl, imidazole, triazole, oxazole, isoxazole, oxadiazole, thiazolyl, isothiazole, thiadiazolyl, benzophenone ... pyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiazolyl, azadibenzothiophenyl, azadibenzofuranyl, etc.),

[0529] The radical T1 can be cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornane (or bicyclo[2.2.1]heptane) radical, norbornenyl, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane or phenyl,

[0530] The radical T2 can be furanyl, thienyl, 1H-pyrrolyl, thiolyl, borocyclopentyl, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathiolyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetraazinyl, pyrrolidinyl, imidazolidinyl, dihydropyrrolyl, piperidinyl, tetrahydropyridinyl, dihydropyridinyl, hexahydropyrimidinyl, tetrahydropyrimidinyl, dihydropyrimidinyl, piperazinyl, tetrahydropyrazinyl, dihydropyrazinyl, tetrahydropyridazinyl or dihydropyridazinyl,

[0531] The group T3 may be furyl, thienyl, 1H-pyrrolyl, thiole or borocyclopentadienyl, and

[0532] The group T4 can be 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathioyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl or tetrazinyl.

[0533] As used herein, the terms "cyclic group", "C 3 -C 60 Carbocyclic group, "C 1 -C 60 Heterocyclic group", "π-electron-rich C 3 -C 60 Cyclic group" or "π-electron-deficient nitrogen-containing C 1 -C 60 The "heterocyclic group" may refer to a group fused to any cyclic group, a monovalent group or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) according to the structure of the formula in which the corresponding term is used. For example, "phenyl" may be benzo, phenyl and / or phenylene, etc., which may be easily understood by a person of ordinary skill in the art based on the structure of the formula including "phenyl".

[0534] Depending on the context, in the present disclosure, a divalent group may refer to or be a multivalent group (eg, trivalent, tetravalent, etc., not just divalent), according to, for example, the structure of a formula associated with a term.

[0535] One Price C 3 -C 60 Carbocyclic groups and monovalent C 1 -C 60 Non-limiting examples of heterocyclic groups may include C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group. 3 -C 60 Carbocyclic groups and divalent C 1 -C 60 Non-limiting examples of heterocyclic groups may include C 3 -C 10 Cycloalkylene, C 1 -C 10 Heterocycloalkylene, C 3 -C10 Cycloalkenylene, C 1 -C 10 Heterocycloalkenylene, C 6 -C 60 Arylene, C 1 -C 60 a heteroarylene group, a divalent non-aromatic fused polycyclic group, and a divalent non-aromatic fused heteropolycyclic group.

[0536] As used herein, the term "C 1 -C 60 The term “alkyl” refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof may be methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl and tert-decyl. As used herein, the term “C 1 -C 60 "Alkylene" refers to 1 -C 60 The alkyl group has substantially the same structure as a divalent group.

[0537] As used herein, the term "C 2 -C 60 "Alkenyl" refers to 2 -C 60 The term "C" as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminal of the alkyl group, and non-limiting examples thereof may be vinyl, propenyl, and butenyl. 2 -C 60 "Alkenylene" refers to 2 -C 60 The alkenyl group has a divalent group having substantially the same structure.

[0538] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a C 2 -C 60 The term "C" as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminal of the alkyl group, and non-limiting examples thereof may include ethynyl and / or propynyl, etc. 2 -C 60 "Alkynylidene" refers to 2 -C 60 Alkynyl groups have substantially the same structure as a divalent group.

[0539] As used herein, the term "C 1 -C 60 "Alkoxy" refers to -OA 101 A univalent group represented by 101 It is C 1 -C 60 alkyl), and non-limiting examples thereof may include methoxy, ethoxy, and isopropoxy.

[0540] As used herein, the term "C 3 -C 10 The term "cycloalkyl" as used herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, and bicyclo[2.2.2]octyl. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hex 3 -C 10 "Cycloalkylene" refers to 3 -C 10 The cycloalkyl group has a divalent group having substantially the same structure.

[0541] As used herein, the term "C 1 -C 10 The term "heterocycloalkyl" as used herein refers to a monovalent cyclic group of 1 to 10 carbon atoms which includes at least one heteroatom as a ring-forming atom in addition to carbon atoms, and non-limiting examples thereof may be 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl, and tetrahydrothienyl. 1 -C 10 "Heterocycloalkylene" refers to a C 1 -C 10 The heterocycloalkyl group has substantially the same structure as a divalent group.

[0542] As used herein, the term "C 3 -C 10 The term "cycloalkenyl" as used herein refers to a monovalent cyclic group having 3 to 10 carbon atoms and having at least one carbon-carbon double bond in its ring and having no aromaticity, and non-limiting examples thereof may be cyclopentenyl, cyclohexenyl and cycloheptenyl. 3 -C 10 "Cycloalkenylene" refers to 3 -C 10 The cycloalkenyl group has a divalent group having substantially the same structure.

[0543] As used herein, the term "C 1 -C 10The term "heterocycloalkenyl group" refers to a monovalent cyclic group of 1 to 10 carbon atoms which includes at least one heteroatom as a ring-forming atom in addition to carbon atoms and has at least one double bond in its ring structure. 1 -C 10 Non-limiting examples of heterocycloalkenyl groups may include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. As used herein, the term “C 1 -C 10 "Heterocycloalkenylene" refers to 1 -C 10 The heterocycloalkenyl group has a divalent group having substantially the same structure.

[0544] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term "C 6 -C 60 "Arylene" refers to a divalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Non-limiting examples of aryl groups include phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, phenyl, peryl, pentaphenyl, heptaphenyl, tetraphenyl, peryl, hexyl, pentyl, rubidinyl, corynyl and ovalenyl. 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, these rings may be fused to each other.

[0545] As used herein, the term "C 1 -C 60 "Heteroaryl" refers to a monovalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms which includes at least one heteroatom as a ring atom in addition to carbon atoms. As used herein, the term "C 1 -C 60 The term "heteroarylene" refers to a divalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms and containing at least one heteroatom as a ring atom in addition to carbon atoms. 1 -C 60 Non-limiting examples of heteroaryl groups can be pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, and naphthyridinyl. 1 -C60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include two or more rings, these rings may be fused to each other.

[0546] The term "monovalent non-aromatic fused polycyclic radical" as used in this article refers to a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings fused to each other, only carbon atoms as ring atoms, and generally no aromaticity in its entire molecular structure. Non-limiting examples of monovalent non-aromatic fused polycyclic radicals are indenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, indenophenanthryl, and indenoanthryl. The term "divalent non-aromatic fused polycyclic radical" as used in this article refers to a divalent group having substantially the same structure as the monovalent non-aromatic fused polycyclic radical described above.

[0547] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings fused to each other which includes at least one heteroatom as a ring-constituting atom in addition to carbon atoms and has no aromaticity in its entire molecular structure as a whole. Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group may include pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiorolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiorolyl, dibenzothiophenyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzothiorolyl, azadibenzothiophenyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazole, thiazolyl, oxadiazole, thiadi ... The term "divalent non-aromatic condensed heteropolycyclic group" as used herein refers to a divalent group having substantially the same structure as a monovalent non-aromatic condensed heteropolycyclic group.

[0548] As used herein, the term "C 6 -C 60 Aryloxy" indicates -OA 102 (A 102 It is C 6 -C 60 aryl), and as used herein, the term "C6 -C 60 "Arylthio" refers to -SA 103 (A 103 It is C 6 -C 60 aryl).

[0549] As used herein, the term "C 7 -C 60 "Aralkyl" refers to -A 104 A 105 (A 104 Can be C 1 -C 54 Alkylene, and A 105 Can be C 6 -C 59 aryl), and as used herein, the term "C 2 -C 60 "Heteroaralkyl" refers to -A 106 A 107 (A 106 Can be C 1 -C 59 Alkylene, and A 107 Can be C 1 -C 59 heteroaryl).

[0550] As used herein, the term " 10a ” means:

[0551] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0552] C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -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 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof;

[0553] C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 heteroarylalkyl, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -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 )、-P(=O)(Q 21)(Q 22 ) or any combination thereof; or

[0554] -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 ) or -P(=O)(Q 31 )(Q 32 ).

[0555] The Q used in this paper 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic groups, each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl or any combination thereof; C 7 -C 60 Aralkyl; or C 2 -C 60 Heteroaralkyl.

[0556] As used herein, the term "heteroatom" refers to any atom other than carbon and hydrogen atoms. Non-limiting examples of heteroatoms may be O, S, N, P, Si, B, Ge, Se, and any combination thereof.

[0557] As used herein, "Ph" refers to phenyl, as used herein, "Me" refers to methyl, as used herein, "Et" refers to ethyl, as used herein, "tert-Bu" or "Bu" refers to ethyl. t " refers to tert-butyl, and "OMe" as used herein refers to methoxy.

[0558] As used herein, the term "biphenyl" refers to a "phenyl group substituted by a phenyl group". In some embodiments, a "biphenyl group" is a group having C 6 -C 60 A substituted phenyl group having an aryl group as a substituent.

[0559] As used herein, the term "terphenyl" refers to a "phenyl group substituted with a biphenyl group". In some embodiments, the "terphenyl group" is a group having a C 6 -C 60 Aryl substituted C 6 -C 60 A substituted phenyl group having an aryl group as a substituent.

[0560] In the present disclosure, the x-axis (x-axis direction), the y-axis (y-axis direction), and the z-axis (z-axis direction) are not limited to the three axes (directions) in the orthogonal coordinate system, and can be interpreted in a broad sense including these axes (directions). For example, the x-axis (x-axis direction), the y-axis (y-axis direction), and the z-axis (z-axis direction) may refer to axes (directions) that are orthogonal to each other, or may refer to axes (directions) that are not orthogonal to each other and are in different directions.

[0561] Unless otherwise defined, * and *' as used herein each refer to a binding site to an adjacent atom in the corresponding formula or moiety.

[0562] Hereinafter, compounds according to one or more embodiments and organic light-emitting devices according to one or more embodiments will be described in more detail with reference to synthesis examples and examples. The phrase "using B instead of A" used in describing the synthesis examples means using B instead of A in the same molar equivalent.

[0563] Synthesis Example

[0564] Synthesis Example 1: Synthesis of Compound 14

[0565] Compound 14 according to one or more embodiments can be synthesized, for example, by the following reaction.

[0566]

[0567] Synthesis of intermediate 14a

[0568] [1,1'-biphenyl]-4-amine (1.2 equivalents), 4-bromo-1,1'-biphenyl (1.0 equivalents), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.10 equivalents) and sodium tert-butoxide (1.5 equivalents) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with diethyl ether and water (e.g., extracted with diethyl ether and washed three times with water), and the resulting organic layer was filtered through MgSO 4 Drying, and then drying under reduced pressure. The resulting product was subjected to column chromatography to obtain Intermediate 14a. (Yield: 70%)

[0569] Synthesis of intermediate 14b

[0570] Intermediate 14a (1.0 equivalent), 1-bromo-4-chlorobenzene (1.0 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 The product was dried and then dried under reduced pressure. The obtained product was subjected to column chromatography to obtain Intermediate 14b. (Yield: 62%)

[0571] Synthesis of intermediate 14c

[0572] 3-Phenylnaphthalene-2-amine (1.2 equivalents), 2-chloro-5,9,9-trimethyl-9H-fluorene (1.0 equivalents), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.10 equivalents) and sodium tert-butoxide (1.5 equivalents) were dissolved in 50 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with diethyl ether and water, and the resulting organic layer was washed with MgSO 4 Drying, and then drying under reduced pressure. The resulting product was subjected to column chromatography to obtain Intermediate 14c. (Yield: 65%)

[0573] Synthesis of compound 14

[0574] Intermediate 14b (1.0 equivalent), Intermediate 14c (1.0 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 50 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4The resulting product was subjected to column chromatography to obtain Compound 14. (Yield: 73%)

[0575] Synthesis Example 2: Synthesis of Compound 33

[0576] Compound 33 according to one or more embodiments can be synthesized, for example, by the following reaction.

[0577]

[0578] Synthesis of intermediate 33a

[0579] Diphenylamine (1.2 equivalents), 1-bromo-3-chlorobenzene (1.0 equivalents), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.10 equivalents) and sodium tert-butoxide (1.5 equivalents) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 The product was dried and then dried under reduced pressure. The obtained product was subjected to column chromatography to obtain Intermediate 33a. (Yield: 68%)

[0580] Synthesis of intermediate 33b

[0581] 2-Bromo-9,9-dimethyl-9H-fluorene (1.0 equivalent), 1-phenylnaphthalene-2-amine (1.2 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 The product was dried and then dried under reduced pressure. The obtained product was subjected to column chromatography to obtain Intermediate 33b. (Yield: 65%)

[0582] Synthesis of compound 33

[0583] Intermediate 33a (1.0 equivalent), Intermediate 33b (1.0 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 The resulting product was subjected to column chromatography to obtain Compound 33. (Yield: 63%)

[0584] Synthesis Example 3: Synthesis of Compound 50

[0585] Compound 50 according to one or more embodiments can be synthesized, for example, by the following reaction.

[0586]

[0587] Synthesis of intermediate 50a

[0588] Aniline (1.2 equivalents), 4-bromo-1,1'-biphenyl (1.0 equivalents), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.10 equivalents) and sodium tert-butoxide (1.5 equivalents) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 The product was dried and then dried under reduced pressure. The obtained product was subjected to column chromatography to obtain Intermediate 50a. (Yield: 68%)

[0589] Synthesis of intermediate 50b

[0590] Intermediate 50a (1.0 equivalent), 1-bromo-3-chlorobenzene (1.0 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 The product was dried and then dried under reduced pressure. The obtained product was subjected to column chromatography to obtain Intermediate 50b. (Yield: 66%)

[0591] Synthesis of intermediate 50c

[0592] 1-Phenylnaphthalene-2-amine (1.2 equivalents), 2-chloro-5-methyl-9,9-diphenyl-9H-fluorene (1.0 equivalents), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.10 equivalents) and sodium tert-butoxide (1.5 equivalents) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 Drying, and then drying under reduced pressure. The resulting product was subjected to column chromatography to obtain Intermediate 50c. (Yield: 60%)

[0593] Synthesis of compound 50

[0594] Intermediate 50b (1.0 equivalent), Intermediate 50c (1.0 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 The resulting product was subjected to column chromatography to obtain Compound 50. (Yield: 70%)

[0595] Synthesis Example 4: Synthesis of Compound 62

[0596] Compound 62 according to one or more embodiments can be synthesized, for example, by the following reaction.

[0597]

[0598] Synthesis of intermediate 62a

[0599] Aniline (1.2 equivalents), 1-bromo-4-cyclohexylbenzene (1.0 equivalents), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.10 equivalents) and sodium tert-butoxide (1.5 equivalents) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 Drying, and then drying under reduced pressure. The resulting product was subjected to column chromatography to obtain Intermediate 62a. (Yield: 66%)

[0600] Synthesis of intermediate 62b

[0601] Intermediate 62a (1.0 equivalent), 1-bromo-3-chlorobenzene (1.0 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 Drying, and then drying under reduced pressure. The resulting product was subjected to column chromatography to obtain Intermediate 62b. (Yield: 70%)

[0602] Synthesis of intermediate 62c

[0603] 3-Phenylnaphthalene-2-amine (1.2 equivalents), 2-bromo-5,9-diphenyl-9H-carbazole (1.0 equivalents), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.10 equivalents) and sodium tert-butoxide (1.5 equivalents) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 Drying, and then drying under reduced pressure. The resulting product was subjected to column chromatography to obtain Intermediate 62c. (Yield: 63%)

[0604] Synthesis of compound 62

[0605] Intermediate 62b (1.0 equivalent), Intermediate 62c (1.0 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 The resulting product was subjected to column chromatography to obtain Compound 62 (yield: 58%).

[0606] Synthesis Example 5: Synthesis of Compound 86

[0607] Compound 86 according to one or more embodiments can be synthesized, for example, by the following reaction.

[0608]

[0609] Synthesis of intermediate 86a

[0610] Intermediate 62a (1.0 equivalent), 4,4"-dichloro-1,1':4',1"-terphenyl (1.1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was purified by MgSO 4 Drying, and then drying under reduced pressure. The resulting product was subjected to column chromatography to obtain Intermediate 86a. (Yield: 70%)

[0611] Synthesis of compound 86

[0612] Intermediate 86a (1.0 equivalent), Intermediate 50c (1.0 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 The resulting product was subjected to column chromatography to obtain Compound 86. (Yield: 70%)

[0613] Synthesis Example 6: Synthesis of Compound 99

[0614] Compound 99 according to one or more embodiments can be synthesized, for example, by the following reaction.

[0615]

[0616] Synthesis of intermediate 99a

[0617] Diphenylamine (1.0 equivalent), 3,3"-dichloro-1,1':4',1"-terphenyl (1.1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 The product was dried and then dried under reduced pressure. The obtained product was subjected to column chromatography to obtain Intermediate 99a. (Yield: 68%)

[0618] Synthesis of intermediate 99b

[0619] 3-Bromodibenzo[b,d]furan (1.0 equivalent), 1-phenylnaphthalene-2-amine (1.2 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 The product was dried and then dried under reduced pressure. The obtained product was subjected to column chromatography to obtain Intermediate 99b. (Yield: 60%)

[0620] Synthesis of compound 99

[0621] Intermediate 99a (1.0 equivalent), Intermediate 99b (1.0 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 The resulting product was subjected to column chromatography to obtain Compound 99. (Yield: 72%)

[0622] Synthesis Example 7: Synthesis of Compound 126

[0623] Compound 126 according to one or more embodiments can be synthesized, for example, by the following reaction.

[0624]

[0625] Synthesis of intermediate 126a

[0626] 4-Cyclohexyl-N-phenylaniline (1.0 equivalent), 4,4"-dichloro-1,1':3',1"-terphenyl (1.1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 Drying, and then drying under reduced pressure. The resulting product was subjected to column chromatography to obtain Intermediate 126a. (Yield: 60%)

[0627] Synthesis of compound 126

[0628] Intermediate 126a (1.0 equivalent), Intermediate 14c (1.0 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 The resulting product was subjected to column chromatography to obtain Compound 126. (Yield: 70%)

[0629] Synthesis Example 8: Synthesis of Compound 143

[0630] Compound 143 according to one or more embodiments can be synthesized, for example, by the following reaction.

[0631]

[0632] Synthesis of intermediate 143a

[0633] Diphenylamine (1.0 equivalent), 3,3"-dichloro-1,1':3',1"-terphenyl (1.1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 The product was dried and then dried under reduced pressure. The obtained product was subjected to column chromatography to obtain Intermediate 143a. (Yield: 63%)

[0634] Synthesis of compound 143

[0635] Intermediate 143a (1.0 equivalent), Intermediate 50c (1.0 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 The resulting product was subjected to column chromatography to obtain Compound 143. (Yield: 71%)

[0636] Synthesis Example 9: Synthesis of Compound 165

[0637] Compound 165 according to one or more embodiments can be synthesized, for example, by the following reaction.

[0638]

[0639] Synthesis of intermediate 165a

[0640] (3-(Diphenylamino)phenyl)boronic acid (1.0 equivalent), 4-bromo-4"-chloro-1,1':4',1"-terphenyl (1.0 equivalent), tetrakis(triphenylphosphine)palladium (0.1 equivalent) and potassium carbonate (3.0 equivalent) were dissolved in 200 mL of toluene, 40 mL of ethanol and 80 mL of water, and then stirred at a temperature of 110° C. for 24 hours under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with diethyl ether and water, and the resulting organic layer was washed with MgSO 4 Drying, and then drying under reduced pressure. The resulting product was subjected to column chromatography to obtain Intermediate 165a. (Yield: 75%)

[0641] Synthesis of intermediate 165b

[0642] 2-Bromo-9-phenyl-9H-carbazole (1.0 equivalent), 3-phenylnaphthalene-2-amine (1.2 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 Drying, and then drying under reduced pressure. The resulting product was subjected to column chromatography to obtain Intermediate 165b. (Yield: 60%)

[0643] Synthesis of compound 165

[0644] Intermediate 165a (1.0 equivalent), Intermediate 165b (1.0 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 The resulting product was subjected to column chromatography to obtain Compound 165. (Yield: 70%)

[0645] Synthesis Example 10: Synthesis of Compound 173

[0646] Compound 173 according to one or more embodiments can be synthesized, for example, by the following reaction.

[0647]

[0648] Synthesis of intermediate 173a

[0649] Diphenylamine (1.0 equivalent), 4,4'-dichloro-1,1':2',1':2",1''-quadrphenyl (1.1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 Drying, and then drying under reduced pressure. The resulting product was subjected to column chromatography to obtain Intermediate 173a. (Yield: 60%)

[0650] Synthesis of compound 173

[0651] Intermediate 173a (1.0 equivalent), Intermediate 33b (1.0 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 The resulting product was subjected to column chromatography to obtain Compound 173. (Yield: 65%)

[0652] Synthesis Example 11: Synthesis of Compound 181

[0653] Compound 181 according to one or more embodiments can be synthesized, for example, by the following reaction.

[0654]

[0655] Synthesis of compound 181

[0656] Intermediate 33b (2.2 equivalents), intermediate 1,4-dibromobenzene (1.0 equivalents), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.10 equivalents) and sodium tert-butoxide (1.5 equivalents) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 The resulting product was subjected to column chromatography to obtain Compound 181. (Yield: 76%)

[0657] Synthesis Example 12: Synthesis of Compound 182

[0658] Compound 182 according to one or more embodiments can be synthesized, for example, by the following reaction.

[0659]

[0660] Synthesis of intermediate 182a

[0661] [1,1'-biphenyl]-4-amine (1.2 equivalents), 2-bromodibenzo[b,d]thiophene (1.0 equivalents), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.10 equivalents) and sodium tert-butoxide (1.5 equivalents) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4Drying, and then drying under reduced pressure. The resulting product was subjected to column chromatography to obtain Intermediate 182a. (Yield: 62%)

[0662] Synthesis of intermediate 182b

[0663] Intermediate 182a (1.0 equivalent), 1-bromo-4-chlorobenzene (1.0 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was purified by MgSO 4 The product was dried and then dried under reduced pressure. The obtained product was subjected to column chromatography to obtain Intermediate 182b. (Yield: 65%)

[0664] Synthesis of intermediate 182c

[0665] Naphthalene-2-amine (1.2 equivalents), 2-bromo-9-phenyl-9H-carbazole (1.0 equivalents), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.10 equivalents) and sodium tert-butoxide (1.5 equivalents) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 Drying, and then drying under reduced pressure. The resulting product was subjected to column chromatography to obtain Intermediate 182c. (Yield: 70%)

[0666] Synthesis of compound 182

[0667] Intermediate 182b (1.0 equivalent), Intermediate 182c (1.0 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.10 equivalent) and sodium tert-butoxide (1.5 equivalent) were dissolved in 100 mL of toluene and then stirred at 80° C. for 1 hour under a nitrogen atmosphere. Once the reaction was completed, the reaction product was washed three times with ether and water, and the resulting organic layer was washed with MgSO 4 The resulting product was subjected to column chromatography to obtain Compound 182. (Yield: 62%)

[0668] Example

[0669] Comparative Example 1

[0670] As an anode, a 15Ω / cm 2 The glass substrate of ITO electrode (Corning Inc. product) was cut into a size of 50 mm × 50 mm × 0.7 mm, ultrasonically treated in isopropanol and pure water for 5 minutes each, and then cleaned by ultraviolet irradiation and exposure to ozone for 30 minutes. Then, the obtained ITO glass substrate was mounted on a vacuum deposition device.

[0671] NPD is deposited on the anode to form a A hole injection layer having a thickness of , and then HT3 is deposited on the hole injection layer to form a A hole transport layer having a thickness of , and then CzSi is deposited on the hole transport layer to form a The thickness of the emission auxiliary layer is .

[0672] Host (HT-3 and ET-2), phosphorescent sensitizer (PS-2) and t-DABNA boron dopant were co-deposited on the emission auxiliary layer in a weight ratio of 42:42:15:1 to form a The emission layer is formed by depositing TSPO1 on the emission layer to form an A hole blocking layer with a thickness of 1000 mm is formed, and TPBi is deposited on the hole blocking layer to form a An electron transport layer having a thickness of , LiF is deposited on the electron transport layer to form a An electron injection layer having a thickness of , and Al is deposited on the electron injection layer to form a A cathode with a thickness of is formed, thereby completing the manufacture of the light-emitting device.

[0673]

[0674] Comparative Examples 2 to 9 and Examples 1 to 12

[0675] Organic light-emitting devices were each manufactured in substantially the same manner as in Comparative Example 1, except that each of the compounds shown in Table 1 was used instead of HT3 in forming the hole transport layer.

[0676] Evaluation example

[0677] In the evaluation results of each organic light emitting device manufactured according to Examples 1 to 12 and Comparative Examples 1 to 9, each of the driving voltage (V), emission wavelength (nm), luminous efficiency (cd / A), and emission color was measured by using Keithley MU 236 and a luminance meter PR650. 2 The luminous efficiency was measured at a current density of . According to "(T of each of the examples and comparative examples 95 value) / (T of Comparative Example 1 95 Lifespan ratio (T95 , reference ratio) refers to the time (h) required for the luminance to reach 95% of the initial luminance of each of the light-emitting devices of the above examples and comparative examples, expressed as a percentage (%) of the life of the light-emitting device of comparative example 1 set to 100. The results are shown in Table 1.

[0678] Table 1

[0679]

[0680]

[0681]

[0682]

[0683] It can be confirmed from Table 1 that, in substantially the same blue light range, the organic light emitting devices of Examples 1 to 12 each exhibit relatively lower driving voltage, higher efficiency, and longer lifespan than the organic light emitting devices of Comparative Examples 1 to 9.

[0684] The amine-containing compound may be included in a hole transport region of a light-emitting device, which may achieve higher efficiency and longer lifetime of the light-emitting device and a display apparatus.

[0685] An organic light emitting device including the amine-containing compound according to one or more embodiments may have improved device characteristics including high efficiency, low driving voltage, and long lifespan.

[0686] In one or more embodiments, high-quality electronic devices and electronic equipment may be manufactured by using the organic light emitting device.

[0687] In the present disclosure, it will be understood that the terms “include,” “comprises,” or “has” specify the presence of stated features, integers, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, and / or groups thereof.

[0688] Throughout this disclosure, when it is mentioned that a component such as a layer, film, region, or plate is located "on" another component, it will be understood that the component can be directly on the other component, or other components can be interposed between them. In some embodiments, "directly on..." can mean that there are no additional layers, films, regions, plates, etc. between the layer, film, region, plate, etc. and the other component. For example, "directly on..." can mean that two layers or two components are arranged without using additional components such as bonding components between them.

[0689] In the present disclosure, although the terms "first", "second", etc. may be used herein to describe one or more elements, components, regions and / or layers, these elements, components, regions and / or layers should not be limited by these terms. These terms are only used to distinguish one component from another component.

[0690] As used herein, the singular forms "a", "an", "an", and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. In addition, when describing embodiments of the present disclosure, the use of "may" refers to "one or more embodiments of the present disclosure."

[0691] As used herein, the terms "substantially," "approximately," or similar terms are used as terms of approximation rather than terms of degree, and are intended to account for the inherent deviations in measured or calculated values ​​that one of ordinary skill in the art would recognize. Taking into account the measurement in question and the errors associated with the measurement of a particular quantity (i.e., the limitations of the measurement system), "approximately" as used herein includes the stated value and means within an acceptable range of deviations of the particular value determined by one of ordinary skill in the art. For example, "approximately" can mean within one or more standard deviations, or within ±30%, ±20%, ±10%, or ±5% of the stated value.

[0692] Any numerical range described in this article is intended to include all sub-ranges of the same numerical precision contained in the range described. For example, the range of "1.0 to 10.0" is intended to include all sub-ranges between the minimum value 1.0 described and the maximum value 10.0 described (and including the endpoint values), that is, having 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 described in this article is intended to include all numerical lower limits included therein, and any minimum numerical limit described in this disclosure is intended to include all numerical upper limits included therein. Therefore, the applicant reserves the right to modify this disclosure (including claims) to explicitly describe any sub-ranges included in the range explicitly described in this article.

[0693] According to the organic light-emitting device, light-emitting device, display device, electronic device, electronic device or any other related device or component of the embodiment of the present disclosure described herein can be implemented using any suitable hardware, firmware (e.g., a dedicated integrated circuit), software or a combination of software, firmware and hardware. For example, the various components of the device can be formed on an integrated circuit (IC) chip or on a separate IC chip. In addition, the various components of the device can be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on a substrate. In addition, the various components of the device can be processes or threads running on one or more processors, in one or more computing devices, executing computer program instructions and interacting with other system components to perform the various functions described herein. The computer program instructions are stored in a memory, which can be implemented in a computing device using a standard storage device (e.g., a random access memory (RAM)). The computer program instructions can also be stored in other non-temporary computer-readable media (e.g., a compact disc read-only memory (CD-ROM) or a flash drive, etc.). In addition, those skilled in the art should recognize that, without departing from the scope of the embodiments of the present disclosure, the functions of various computing devices may be combined or integrated into a single computing device, or the functions of a particular computing device may be distributed on one or more other computing devices.

[0694] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for the purpose of limitation. The description of features or aspects within each embodiment should generally be considered to be applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that one or more suitable changes in form and details may be made therein without departing from the spirit and scope defined by the appended claims and their equivalents.

Claims

1. An amine-containing compound represented by Formula 1, wherein: Formula 1 Among them, in formula 1, Ar 11 ,Ar 12 and Ar 21 Each independently is C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group, Ar 31 ,Ar 32 , L2 and L3 are each independently: unsubstituted or substituted with at least one R 10a Substituted C3-C 60 carbocyclyl; or unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, m2 is an integer from 0 to 5, When m2 is 0, then *-(L2) m2 The group represented by -*' is a single bond, m3 is 1, 3 or 4, X is C(R4)(R5), N(R6), O or S, R1, R2, R4, R5 and R6 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C3-C 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 10 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C3-C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryl, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10a A substituted monovalent non-aromatic fused polycyclic group, unsubstituted or substituted with at least one R 10a a substituted monovalent non-aromatic fused heteropolycyclic group, -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), or -P(=S)(Q1)(Q2), Two or more adjacent groups selected from R1, R2, R4, R5 and R6 are optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, n1 and n2 are each independently an integer from 0 to 15, When n1 is an integer of 2 or more, the plurality of R1 are the same as or different from each other, When n2 is an integer of 2 or more, the multiple R2 are the same or different from each other, R 10a for: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, -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 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof; C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy or C6-C 60 Arylthio, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, -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 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or -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 ) or -P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each independently represents: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 Alkoxy; or C3-C 60 Carbocyclic or C1-C 60 Heterocyclic groups, each unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 substituted with alkoxy, phenyl, biphenyl or any combination thereof, and * and *' each independently indicate a binding site to an adjacent atom.

2. The amine-containing compound according to claim 1, wherein Ar 11 and Ar 12 Each is independently phenyl, naphthyl, phenanthryl, fluoranthenyl, triphenylenyl, pyrene, 1-4-dime, 1-6-dime, 1-8 ...

3. The amine-containing compound according to claim 1, wherein The amine-containing compound represented by Formula 1 is a compound represented by any one selected from Formula 1-1 to Formula 1-4: Formula 1-1 Formula 1-2 Formula 1-3 Formula 1-4 And wherein, in Formula 1-1 to Formula 1-4, Ar 21 ,Ar 31 ,Ar 32 , L2, L3, m2, m3, X, R2 and n2 are the same as described in Formula 1, and R 11 To R 18 Each is independently the same as described with respect to R1 in Formula 1.

4. The amine-containing compound according to claim 1, wherein m2 is 0, 1 or 2.

5. The amine-containing compound according to claim 1, wherein Depend on The group represented is a group represented by Formula 2A or Formula 2B: Formula 2A Formula 2B and Wherein, in Formula 2A and Formula 2B, R 21 To R 28 are each independently the same as described with respect to R2 in Formula 1, and *Indicates the binding site with the neighboring atoms.

6. The amine-containing compound according to claim 5, wherein Depend on The group represented by is a group represented by Formula 2A, and R 21 or R 23 is unsubstituted or replaced by at least one R 10a Substituted C6-C 30 Aryl.

7. The amine-containing compound according to claim 1, wherein L3 is a group represented by any one selected from Formula 3A to Formula 3J: and Wherein, in Formula 3A to Formula 3J, Z 31 To Z 38 Each independently and with respect to R in Formula 1 10a Same as described, and * and *' each independently indicate a binding site to an adjacent atom.

8. The amine-containing compound according to claim 1, wherein m3 is not 2.

9. The amine-containing compound according to claim 1, wherein Ar 31 and Ar 32 are each independently unsubstituted or substituted with at least one R 10a Substituted C6-C 30 Aryl, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heteroaryl.

10. The amine-containing compound according to claim 1, wherein The amine-containing compound represented by Formula 1 is selected from Compound 1 to Compound 182:

11. An organic light emitting device, wherein: The organic light emitting device comprises: a first electrode; a second electrode, facing the first electrode; an intermediate layer between the first electrode and the second electrode and including an emission layer; and The amine-containing compound according to any one of claims 1 to 10.

12. The organic light emitting device according to claim 11, wherein: The first electrode is an anode, The second electrode is a cathode, The intermediate layer further includes a hole transport region between the first electrode and the emissive layer and an electron transport region between the emissive layer and the second electrode, The hole transport region includes at least one selected from a hole injection layer, a hole transport layer, a buffer layer, an emission auxiliary layer and an electron blocking layer, and The electron transport region includes at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.

13. The organic light emitting device according to claim 11, wherein: The amine-containing compound is in the intermediate layer.

14. The organic light emitting device according to claim 12, wherein: The amine-containing compound is in the hole transporting zone.

15. The organic light emitting device according to claim 12, wherein: The amine-containing compound is in the hole transport layer, and The hole transport layer is in direct contact with the emission layer.

16. The organic light emitting device according to claim 11, wherein: The organic light emitting device further comprises a covering layer outside the second electrode, Wherein, the amine-containing compound is in the covering layer.

17. The organic light emitting device according to claim 11, wherein: The organic light emitting device further comprises at least one of the following: A first covering layer, outside the first electrode; as well as a second covering layer, outside the second electrode, Wherein, at least one of the first covering layer and the second covering layer includes the amine-containing compound.

18. An electronic device, wherein: The electronic device comprises the organic light emitting device according to any one of claims 11 to 17.

19. The electronic device according to claim 18, wherein: The electronic device further comprises a thin film transistor, The thin film transistor includes a source electrode and a drain electrode, and 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.

20. An electronic device, wherein: The electronic equipment includes the organic light emitting device according to any one of claims 11 to 17.

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