Heterocyclic compounds and organic light-emitting devices comprising the same

Abstract

The present application relates to an organic light emitting device including a heterocyclic compound represented by Formula 1, wherein A 11 is a group represented by one of Formula 10A to Formula 10D: The organic light emitting device including the heterocyclic compound can have improved efficiency and / or service life characteristics.

Description

[0001] Cross-reference to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2019-0150485, filed with the Korean Intellectual Property Office on November 21, 2019, the entire contents of which are incorporated herein by reference. Technical Field

[0003] One or more aspects of the embodiments of this disclosure relate to heterocyclic compounds and organic light-emitting devices comprising said heterocyclic compounds. Background Technology

[0004] Organic light-emitting devices are self-emitting devices that produce full-color images, and compared with devices in related technologies, they also have superior characteristics in terms of wide viewing angle, high contrast, short response time and / or brightness, driving voltage and / or response speed.

[0005] An organic light-emitting device may include a first electrode disposed on a substrate, and a hole transport region, an emitter layer, an electron transport region, and a second electrode sequentially disposed on the first electrode. Holes provided by the first electrode can move towards the emitter layer through the hole transport region, and electrons provided by the second electrode can move towards the emitter layer through the electron transport region. Charge carriers (e.g., holes and electrons) can recombine in the emitter layer to generate excitons. These excitons can transition from an excited state to a ground state, thereby generating light. Summary of the Invention

[0006] One or more aspects of the embodiments of this disclosure relate to heterocyclic compounds and organic light-emitting devices comprising said heterocyclic compounds.

[0007] Other aspects will be set forth in part in the description which follows, and will be apparent in part from the description, or may be learned by practicing embodiments of the present disclosure. One or more exemplary embodiments of the present disclosure provide an organic light-emitting device, comprising:

[0008] A first electrode; a second electrode; and an organic layer including an emission layer and located between the first electrode and the second electrode, and

[0009] At least one heterocyclic compound represented by Formula 1,

[0010] The first electrode comprises indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0011] The second electrode comprises lithium (Li), Ag, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, ITO, IZO, or any combination thereof:

[0012] <Formula 1>

[0013]

[0014] In Equation 1,

[0015] X 11 It is NR 15 , O, S or Se,

[0016] A 11 It is a group represented by one of formulas 10A to 10D.

[0017] Y 11 To Y 13 Each is a carbon atom in a group represented by one of formulas 10A to 10D.

[0018] A 12 To A 14 Each is independently C5-C 60 Carbocyclic group,

[0019] R 12 To R 15 Each group is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C. 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C7-C 60 Aryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 heteroaryl groups, substituted or unsubstituted C2-C 60Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thioyl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2),

[0020] b12 to b14 are each independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10.

[0021]

[0022]

[0023] Among them, in Equations 10A to 10D,

[0024] X 111 It is NR 114 , O, S or Se,

[0025] X 112 It is NR 115 , O, S or Se,

[0026] A 111 and A 112 Each is independently C5-C 60 Carbocyclic group,

[0027] Y 11 To Y 13 Each is a carbon atom in Formula 1.

[0028] R 111 To R 115 Each group is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C. 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C7-C 60 Aryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 heteroaryl groups, substituted or unsubstituted C2-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thioyl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2),

[0029] b111 and b112 are each independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10.

[0030] Selected from R 12 To R 15 and R 111 To R 115 Two adjacent groups in the C5-C may be connected to form a substituted or unsubstituted C5-C. 60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups,

[0031] Q1 to Q3 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 Aryl group, C7-C 60 Aryl group, C6-C 60 aryloxy group, C6-C60 Aryl thioyl group, C1-C 60 heteroaryl group, C2-C 60 Heteroaryl groups, C1-C 60 Heteroaryloxy group, C1-C 60 A heteroaryl thioyl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heterocyclic group, a C1-C group substituted with at least one of deuterium, -F and cyano groups. 60 The alkyl group is a C6-C group substituted with at least one of a deuterium, -F, or cyano group. 60 Aryl groups, biphenyl groups, and terphenyl groups, and

[0032] Two adjacent groups selected from Q1 to Q3 are optionally linked to form a substituted or unsubstituted C5-C. 60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups.

[0033] One or more exemplary embodiments of this disclosure provide an apparatus comprising: a thin-film transistor including a source electrode, a drain electrode, and an active layer, and the organic light-emitting device, wherein a first electrode of the organic light-emitting device is electrically connected to one of the source electrode and the drain electrode of the thin-film transistor.

[0034] One or more exemplary embodiments of this disclosure provide heterocyclic compounds represented by Formula 1:

[0035] Formula 1

[0036]

[0037] In Equation 1,

[0038] X 11 It can be NR 15 , O, S or Se,

[0039] A 11 It can be a group represented by one of formulas 10A to 10D.

[0040] Y 11 To Y 13 Each of these can be a carbon atom in a group represented by one of formulas 10A to 10D.

[0041] A 12 To A 14 Each can be C5-C independently. 60 Carbocyclic group,

[0042] R 12 To R 15Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C groups. 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C7-C 60 Aryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 heteroaryl groups, substituted or unsubstituted C2-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thioyl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2),

[0043] b12 to b14 can each be independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10.

[0044]

[0045] In Equations 10A to 10D,

[0046] X 111 It can be NR 114 , O, S or Se,

[0047] X 112 It can be NR 115 , O, S or Se,

[0048] A111 and A 112 Each can be C5-C independently. 60 Carbocyclic group,

[0049] Y 11 To Y 13 Each of them can be a carbon atom in Formula 1.

[0050] R 111 To R 115 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C groups. 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C7-C 60 Aryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 heteroaryl groups, substituted or unsubstituted C2-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thioyl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2),

[0051] b111 and b112 can each be independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10.

[0052] Selected from R 12 To R 15 and R111 To R 115 Two adjacent groups in the C5-C can be optionally linked to form substituted or unsubstituted C5-C. 60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups,

[0053] Q1 to Q3 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 Aryl group, C7-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Aryl thioyl group, C1-C 60 heteroaryl group, C2-C 60 Heteroaryl groups, C1-C 60 Heteroaryloxy group, C1-C 60 A heteroaryl thioyl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heterocyclic group, a C1-C group substituted with at least one of deuterium, -F and cyano groups. 60 The alkyl group is a C6-C group substituted with at least one of a deuterium, -F, or cyano group. 60 Aryl groups, biphenyl groups, and terphenyl groups, and

[0054] Two adjacent groups selected from Q1 to Q3 may optionally be linked to form a substituted or unsubstituted C5-C. 60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups. Attached Figure Description

[0055] The above and other aspects, features and advantages of certain embodiments of this disclosure will become more apparent from the following description taken in conjunction with the accompanying drawings, in which:

[0056] Figure 1 This is a schematic view of the organic light-emitting device according to the implementation plan;

[0057] Figure 2This is a schematic view of an organic light-emitting device according to another embodiment;

[0058] Figure 3 This is a schematic view of an organic light-emitting device according to another embodiment; and

[0059] Figure 4 This is a schematic view of an organic light-emitting device according to another embodiment. Detailed Implementation

[0060] Reference will now be made in more detail to the embodiments, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer throughout to the same elements and may not be described repeatedly. In this respect, the embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, the embodiments are described below only with reference to the accompanying drawings to explain aspects of the present description. As used herein, the term “and / or” includes any combination and all combinations of one or more of the relevant listed items. Throughout the disclosure, the expression “at least one of a, b, and c” may mean only a, only b, only c, both a and b (e.g., simultaneously), both a and c, both b and c, all of a, b, and c, or variations thereof.

[0061] As used herein, the singular forms “a”, “an”, and “the” are intended to also include the plural forms unless the context clearly indicates otherwise.

[0062] It should be further understood that the terms “includes,” “including,” “comprises,” and / or “comprising” used herein specify the presence of a defined feature or component, but do not exclude the presence or addition of one or more other features or components.

[0063] As used herein, expressions such as “at least one of…”, “one of…”, and “selected from” modify the entire column of elements when preceding a column of elements, and do not modify any individual element in that column. Furthermore, when describing embodiments of this disclosure, the use of “may” means “one or more embodiments of this disclosure”.

[0064] It should be understood that when a layer, area, or component is referred to as being "on" or "above" another layer, area, or component, it can be formed directly or indirectly on that other layer, area, or component. For example, there can be intermediate layers, areas, or components. When an element is referred to as being "directly on" another element, "directly connected to" another element, or "directly linked to" another element, there is no intermediate element.

[0065] For ease of explanation, the dimensions of the elements in the accompanying drawings may be enlarged. For example, since the dimensions and thicknesses of the components in the drawings are arbitrarily illustrated for ease of explanation, the following embodiments of this disclosure are not limited thereto.

[0066] One or more exemplary embodiments of this disclosure provide heterocyclic compounds represented by Formula 1:

[0067] Formula 1

[0068]

[0069] A in Formula 1 11 It can be a group represented by one of Formulas 10A to 10D:

[0070]

[0071]

[0072] Y in Equation 1 11 To Y 13 Each of the atoms can be a carbon atom and can correspond to Y selected from one of Formulas 10A to 10D. 11 To Y 13 .

[0073] X in Equation 1 11 It can be NR 15 Oxygen (O), sulfur (S) or selenium (Se).

[0074] X in Equations 10A to 10D 111 It can be NR 114 , O, S or Se.

[0075] X in Equations 10A to 10D 112 It can be NR 115 , O, S or Se.

[0076] A in Formula 1 12 To A 14 Each can be C5-C independently. 60 Carbon ring group.

[0077] A in Equations 10A to 10D 111 and A 112 Each can be C5-C independently. 60 Carbon ring group.

[0078] In some implementations, for example, A in Formula 1 and Formulas 10A to 10D 12 To A 14 A 111 and A112 Each group can be independently selected from phenyl groups, naphthyl groups, fluorene groups, spiro-difluorene groups, benzo[a]fluorene groups, dibenzo[a]fluorene groups, phenanthrene groups, anthracene groups, fluoranthene groups, benzo[a]phenanthrene groups, pyrene groups, etc. Groups and perylene groups.

[0079] In one embodiment, A in Formula 1 and Formulas 10A to 10D 12 To A 14 A 111 and A 112 Each group can be independently selected from phenyl groups, naphthyl groups, and fluorene groups.

[0080] In one embodiment, A in Formula 1 and Formulas 10A to 10D 12 To A 14 A 111 and A 112 Each can be an independent phenyl group.

[0081] R in Equation 1 12 To R 15 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C groups. 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C7-C 60 Aryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 heteroaryl groups, substituted or unsubstituted C2-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60Heteroaryl thioyl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2);

[0082] R in Equations 10A to 10D 111 To R 115 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C groups. 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C7-C 60 Aryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 heteroaryl groups, substituted or unsubstituted C2-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thioyl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2);

[0083] R selected from Equation 1 and Equations 10A to 10D 12 To R 15 and R111 To R 115 The two adjacent groups in the structure can be optionally linked to form a substituted or unsubstituted C5-C. 60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups,

[0084] Q1 to Q3 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 Aryl group, C7-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Aryl thioyl group, C1-C 60 heteroaryl group, C2-C 60 Heteroaryl groups, C1-C 60 Heteroaryloxy group, C1-C 60 A heteroaryl thioyl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heterocyclic group, a C1-C group substituted with at least one of deuterium, -F and cyano groups. 60 The alkyl group is a C6-C group substituted with at least one of a deuterium, -F, or cyano group. 60 Aryl groups, biphenyl groups, and terphenyl groups, and

[0085] Two adjacent groups selected from Q1 to Q3 may optionally be linked to form a substituted or unsubstituted C5-C. 60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups.

[0086] For example, R in Equation 1 and Equations 10A to 10D 15 R 114 and R 115 Each can be independently selected from hydrogen, deuterium, and C1-C. 10 Alkyl groups, C3-C 10 Cycloalkyl groups, C6-C 20 aryl group, C7-C 20 Aryl groups, C1-C20 heteroaryl groups, C2-C 20 Heteroaryl alkyl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups; and

[0087] Each is selected from deuterium, -F, cyano group, C1-C 10 alkyl groups and C3-C 10 At least one substituted C6-C group in the cycloalkyl group 20 aryl group, C7-C 20 Aryl groups, C1-C 20 heteroaryl groups, C2-C 20 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups; or

[0088] R 15 and R 14 R 15 and R 13 R 115 and R 112 R 115 and R 111 and / or R 114 and R 111 They can connect independently to form substituted or unsubstituted C5-C. 20 The carbocyclic group is either substituted or unsubstituted C1-C. 20 Heterocyclic groups.

[0089] In one embodiment, R in Formula 1 and Formulas 10A to 10D 15 R 114 and R 115 Each group can be independently selected from hydrogen, deuterium, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, benzyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, fluorenyl group, dibenzofuranyl group, dibenzothiophenyl group, and carbazoleyl group; and

[0090] Each of the following groups is substituted with at least one of the following groups: deuterium, -F, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl, consisting of a phenyl group, biphenyl group, terphenyl group, naphthyl group, benzyl group, pyridyl group, pyrazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, fluorenyl group, dibenzofuranyl group, dibenzothiophenyl group, and carbazoleyl group; or

[0091] R15 and R 14 R 15 and R 13 R 115 and R 112 R 115 and R 111 and / or R 114 and R 111 They can connect independently to form substituted or unsubstituted C5-C. 20 The carbocyclic group is either substituted or unsubstituted C1-C. 20 Heterocyclic groups.

[0092] For example, R in Equation 1 and Equations 10A to 10D 12 To R 14 and R 111 To R 113 Each can be independently selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 10 Alkyl groups, C1-C 10 alkoxy group, C3-C 10 Cycloalkyl groups, C6-C 20 aryl group, C7-C 20 Aryl groups, C6-C 20 aryloxy group, C6-C 20 aryl thiol groups, C1-C 20 heteroaryl groups, C2-C 20 heteroaryl groups, C1-C 20 heteroaryloxy groups, C1-C 20 Heteroaryl thio groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups;

[0093] Each is selected from deuterium, -F, -Cl, -Br, -I, cyano groups, C1-C 10 Alkyl groups, C1-C 10 alkoxy group, C3-C 10 Cycloalkyl groups, C6-C 20 aryl group, C7-C 20 Aryl groups, C6-C 20 aryloxy group, C6-C 20 aryl thiol groups, C1-C 20 heteroaryl groups, C2-C 20 heteroaryl groups, C1-C 20 heteroaryloxy groups, C1-C 20 At least one of the following: a heteroaryl thio group, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heterocyclic group, is substituted with a C1-C group. 10Alkyl groups, C1-C 10 alkoxy group, C3-C 10 Cycloalkyl groups, C6-C 20 aryl group, C7-C 20 Aryl groups, C6-C 20 aryloxy group, C6-C 20 aryl thiol groups, C1-C 20 heteroaryl groups, C2-C 20 heteroaryl groups, C1-C 20 heteroaryloxy groups, C1-C 20 Heteroaryl thio groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups; and

[0094] -Si(Q1)(Q2)(Q3), -B(Q1)(Q2) and -N(Q1)(Q2),

[0095] Q1 to Q3 can each be independently hydrogen, deuterium, or C1-C. 10 Alkyl group, C3-C 10 Cycloalkyl groups, C6-C 20 Aryl group, C7-C 20 Aryl group, C1-C 20 heteroaryl group, C2-C 20 A heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heterocyclic group, a C1-C group substituted with at least one of deuterium, -F and cyano groups. 10 The alkyl group is a C6-C group substituted with at least one of a deuterium, -F, or cyano group. 20 aryl group, biphenyl group and terphenyl group, or

[0096] Q1 and Q2 can be connected to form substituted or unsubstituted C5-C. 20 The carbocyclic group is either substituted or unsubstituted C1-C. 20 Heterocyclic groups.

[0097] In one embodiment, R in Formula 1 and Formulas 10A to 10D 12 To R 14 and R 111 To R 113 Each can be selected independently from:

[0098] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, isobutoxy group, and tert-butoxy group;

[0099] Each of the following groups is substituted with at least one of the following groups: a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, a sec-butoxy group, an isobutoxy group, and a tert-butoxy group;

[0100] A group represented by one of formulas 3-1 to 3-3; and

[0101] A group represented by one of formulas 5-1 to 5-142:

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109] In equations 3-1 to 3-3 and equations 5-1 to 5-142

[0110] A 31 It can be selected from phenyl groups, naphthyl groups, phenanthrene groups, benzo[a]phenanthrene groups, and anthracene groups.

[0111] X 51 It can be selected from O, S, N(R) 51 ) and C(R 51 (R) 60 ),

[0112] X 52 It can be N or C(R) 52 ), X 53 It can be N or C(R) 53 ), X 54 It can be N or C(R) 54), X 55 It can be N or C(R) 55 ), X 56 It can be N or C(R) 56 ), X 57 It can be N or C(R) 57 ), X 58 It can be N or C(R) 58 ), and X 59 It can be N or C(R) 59 ),

[0113] R 31 To R 37 and R 51 To R 60 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, isobutoxy group, tert-butoxy group, phenyl group, biphenyl group, terp-phenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthrene group, anthracene group, fluoranthracene group, benzo[a]phenanthrene group, pyrene group, etc. Peryl group, peryl group, thiophene group, furanyl group, thiophene group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) and -P(=S)(Q 31 (Q) 32 );

[0114] Q 31 To Q 33 Each can be independently selected from C1-C 60 Alkyl groups, phenyl groups, biphenyl groups, and terphenyl groups,

[0115] b31 can be selected from 1, 2, 3, 4, 5, 6, 7, 8, and 9.

[0116] b51 can be selected from 1, 2, 3, 4, and 5.

[0117] b52 can be selected from 1, 2, 3, 4, 5, 6, and 7.

[0118] b53 can be selected from 1, 2, 3, 4, 5, 6, 7, 8, and 9.

[0119] b54 can be selected from 1, 2, 3, and 4.

[0120] b55 can be selected from 1, 2, and 3.

[0121] b56 can be selected from 1 and 2.

[0122] b57 can be selected from 1, 2, 3, 4, 5, and 6, and

[0123] * indicates a binding site with an adjacent atom.

[0124] In one embodiment, R in Formula 1 and Formulas 10A to 10D 12 To R 14 and R 111 To R 113 Each can be selected independently from:

[0125] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, isobutoxy group, and tert-butoxy group;

[0126] Each of the following groups is substituted with at least one methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, isobutoxy group, and tert-butoxy group; and

[0127] A group represented by one of formulas 6-1 to 6-163:

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135] In equations 6-1 to 6-163,

[0136] i-Pr can be an isopropyl group.

[0137] t-Bu can be a tert-butyl group.

[0138] Ph can be a phenyl group.

[0139] 1-Naph can be a 1-naphthyl group.

[0140] 2-Naph can be a 2-naphthyl group, and

[0141] * indicates a binding site with an adjacent atom.

[0142] In Equation 1, b12 to b14 represent the substituted R, respectively. 12 To R 14 The quantity, and b12 to b14 can each be determined according to R. 12 To R 14 The maximum number of substitutions at the substitution site is controlled. In one embodiment, b12 to b14 in Formula 1 can each be independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10.

[0143] In Equations 10A to 10D, b111 and b112 represent the substituted R, respectively. 111 and R 112 The quantity, and b111 and b112 can each be determined according to R. 111 and R 112 The maximum number of substitutions at the substitution location is controlled. In one embodiment, b111 and b112 in formulas 10A to 10D can each be independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10.

[0144] In one embodiment, the heterocyclic compound represented by Formula 1 can be represented by one of Formulas 1-1 to 1-3:

[0145] Formula 1-1

[0146]

[0147] Formula 1-2

[0148]

[0149] Formula 1-3

[0150]

[0151] In equations 1-1 to 1-3,

[0152] X 11 A 12 To A 14 R 12 To R 14 b12 to b14, X 111 X 112 A 111 A 112 R 111 To R 113 b111 and b112 can each be independently identical to those described with respect to Equations 1 and 10A to 10D.

[0153] For example, A in equations 1-1 to 1-3 12 To A 14 A 111 and A 112 Each group can be independently selected from phenyl groups, naphthyl groups, and fluorene groups.

[0154] In one or more embodiments, the heterocyclic compound represented by Formula 1 can be represented by Formulas 1-11:

[0155] Formula 1-11

[0156]

[0157] In Equation 1-11,

[0158] X 11 X 111 X 112 and R 113 Each can be independently described as identical to that described with respect to Equations 1 and 10A to 10D.

[0159] R 12a To R 12d R 13a To R 13c and R 14a To R 14d Each can be independently related to R in Equation 1 12 The same description, and

[0160] R 111a To R 111c and R 112a To R 112dEach can be independently related to R in Equation 10A 111 The descriptions are the same.

[0161] In one embodiment, the heterocyclic compound represented by Formula 1 may be represented by one of Formulas 1-21 to 1-24:

[0162] Formula 1-21

[0163]

[0164] Formula 1-22

[0165]

[0166] Formula 1-23

[0167]

[0168] Formula 1-24

[0169]

[0170] In equations 1-21 to 1-24,

[0171] X 11 X 111 and X 112 Each can be independently described as identical to that described with respect to Equations 1 and 10A to 10D.

[0172] R 12b R 13b and R 14a Each can be independently related to R in Equation 1 12 The same description, and

[0173] R 111b and R 112d Each can be independently related to R in Equation 10A 111 The descriptions are the same.

[0174] In one or more embodiments, the heterocyclic compound represented by Formula 1 may be selected from compounds of Group I:

[0175] Group I

[0176]

[0177]

[0178]

[0179]

[0180] The heterocyclic compound represented by Formula 1 can be designed to emit light of any suitable color, such as red, green, blue, etc. In one embodiment, the heterocyclic compound represented by Formula 1 can be designed to emit blue light. In one embodiment, the heterocyclic compound represented by Formula 1 can be designed to emit blue light with a maximum emission wavelength of about 430 nm to about 480 nm, but embodiments of this disclosure are not limited thereto.

[0181] As used herein, the term "maximum emission wavelength" can refer to the wavelength value of the maximum emission intensity in the photoluminescence (PL) spectrum of a solution or membrane sample of a compound.

[0182] Typically, it is desirable (e.g., should be satisfied) for a small energy difference (ΔE) between the lowest excited singlet level and the lowest excited triplet level. ST The large oscillator intensity (f) is used to enable the compound to effectively exhibit thermally activated delayed fluorescence (TADF). This is because of the small ΔE. ST Since there is an inverse relationship between f and large f (e.g., inverse correlation or correlation), it may be difficult to simultaneously (e.g., simultaneously) satisfy small ΔE. ST And large f. However, the heterocyclic compounds represented by Equation 1 can simultaneously (e.g., simultaneously) satisfy small ΔE due to the structural properties described below. ST Both the large f and the large f enable the effective realization of thermally activated delayed fluorescence process.

[0183] The heterocyclic compound represented by Formula 1 contains boron (B) in its core (e.g., in the central region of its fused-ring core). The nitrogen (N) atom in the core has an energy corresponding to the highest occupied molecular orbital (HOMO), the B atom has an energy corresponding to the lowest unoccupied molecular orbital (LUMO), and each carbon (C) atom adjacent to N and B alternately has an energy corresponding to either the HOMO or the LUMO due to resonance effects. In some embodiments, for example, the HOMO may be located on the N atom; the LUMO may be located on the B atom, and the electronic conjugation between them can be mediated via resonance through the aromatic carbon atom. Thus, in the case of the heterocyclic compound, the HOMO and LUMO can be separated at the atomic or molecular level, expressing TADF properties, and containing multiple N, O, and S atoms and two B atoms to provide multiple donors and acceptors, allowing for increased spacing between the HOMO and LUMO. Due to such TADF properties, organic light-emitting devices containing heterocyclic compounds can exhibit high efficiency.

[0184] Furthermore, because HOMO and LUMO overlap (conjugate) due to resonance effects in heterocyclic compounds, emission transitions can easily occur.

[0185] Heterocyclic compounds contain a carbazole ring (partially) in their core, and therefore possess a rigid structure. Typically, compounds may undergo structural changes when absorbing and transferring energy (e.g., by emitting light). Because heterocyclic compounds contain a carbazole ring, these structural changes can be minimized or reduced, resulting in a narrower full width at half maximum (FWHM) and suppression of vibrations, thus contributing to improved quantum efficiency. Reduced structural changes during electron transfer can lead to a decreased Stokes shift. Because heterocyclic compounds contain a carbazole ring in their core, the length or area of ​​the conjugated system can be increased, and the absorption band can shift to longer wavelengths. However, because the Stokes shift value is relatively small, the elongation of the emission wavelength can be suppressed or reduced. In this case, device stability can be improved because the host can be selected from hosts with relatively low lowest excited singlet levels (hosts emitting longer wavelengths of light). Therefore, the efficiency of organic light-emitting devices containing heterocyclic compounds can be improved, and high color purity can be provided.

[0186] For blue light emission, S1 and T1 should each be relatively high. The inclusion of a carbazole ring can give the compound a relatively high binding and dissociation energy. Therefore, because the heterocyclic compound contains a carbazole ring, it can have a high binding and dissociation energy, and this can improve the lifespan of organic light-emitting devices containing the heterocyclic compound.

[0187] Furthermore, because heterocyclic compounds possess relatively high charge (hole or electron) transport capabilities, the exciton formation ratio in the emitter layer of organic light-emitting devices using heterocyclic compounds represented by Formula 1 can be improved. Additionally, because the carbazole moiety is contained within the core, the HOMO level can be deepened (e.g., stabilized), and thus the mismatch with the host HOMO level can be reduced, thereby improving the device's lifetime. Therefore, organic light-emitting devices can exhibit low driving voltage, high efficiency, long lifetime, and / or high maximum quantum efficiency.

[0188] Furthermore, because heterocyclic compounds have relatively small ΔE ST Therefore, a relatively low T1 ratio can be maintained, allowing triplet-triplet annihilation (TTA), triplet-polaron quenching (TPQ), and other events (which occur at high T1 ratios) to occur relatively less frequently. Consequently, the roll-off characteristics of organic light-emitting devices containing heterocyclic compounds can be reduced or improved.

[0189] Dexter energy transfer is the phenomenon in which electrons from triplet excitons are transferred directly from the acceptor to the donor, which is more likely to occur when the intermolecular distance is short. Because the heterocyclic compounds according to the embodiments have structures that extend the intermolecular distance, dexter energy transfer can be suppressed or reduced, and therefore the adverse effects caused by the movement of triplet excitons can be suppressed or reduced.

[0190] Furthermore, because heterocyclic compounds contain only a single carbazole moiety, the structural strain induced by the pentagonal ring of the carbazole structure is relatively smaller than that induced in heterocyclic compounds containing two or more carbazole structures. For example, in heterocyclic compounds containing two or more carbazole structures, deformation (e.g., distortion) may occur, in which the bond between boron (B) and carbon (C) becomes longer (e.g., longer than the average BC bond length) to accommodate the pentagonal ring of the carbazole structure. For this reason, heterocyclic compounds containing two or more carbazole structures can have lower stability than heterocyclic compounds represented by Formula 1.

[0191] Furthermore, because the heterocyclic compound contains two boron (B) atoms, the resonance effect can be relatively large. This can lead to a "short-range charge transfer" phenomenon, in which the HOMO / LUMO spacing is further increased due to atomic separation, and the molecules are extensively fused to expand charge delocalization, allowing for increased molecular polarization and resulting in an increase in the oscillator strength value (e.g., oscillator strength f). Therefore, the efficiency of organic light-emitting devices containing the heterocyclic compound can be improved. Moreover, because the heterocyclic compound has a robust linear molecular model, improved light extraction performance using transition dipoles can be expected.

[0192] The method for synthesizing the heterocyclic compound represented by Formula 1 should be apparent to those skilled in the art by referring to the following examples.

[0193] At least one of the heterocyclic compounds represented by Formula 1 can be used between a pair of electrodes in an organic light-emitting device. For example, the heterocyclic compound may be included in at least one selected from hole transport regions, electron transport regions, and emitter layers. In one or more embodiments, the heterocyclic compound represented by Formula 1 can be used as a material for a capping layer located outside a pair of electrodes in the organic light-emitting device.

[0194] One or more exemplary embodiments of this disclosure provide an organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the organic layer comprises at least one heterocyclic compound represented by Formula 1.

[0195] As used herein, the term "organic layer" can refer to a single layer and / or multiple layers disposed between the first and second electrodes of an organic light-emitting device. The materials contained in the "organic layer" are not limited to organic materials.

[0196] As used herein, the expression “(organic layer) contains at least one heterocyclic compound” can include cases where “(organic layer) contains the same heterocyclic compound represented by Formula 1” (e.g., the same compound) and cases where “(organic layer) contains two or more different heterocyclic compounds represented by Formula 1”.

[0197] For example, the organic layer may contain only compound 1 as a heterocyclic compound. In this respect, compound 1 may exist only (e.g., as the only heterocyclic compound) in the emitting layer of the organic light-emitting device. In one or more embodiments, the organic layer may contain both compound 1 and compound 2 as heterocyclic compounds. Here, compound 1 and compound 2 may exist in the same layer (e.g., both compound 1 and compound 2 may exist in the emitting layer simultaneously) or in different layers (e.g., compound 1 may exist in the emitting layer and compound 2 may exist in the electron transport layer).

[0198] In one embodiment, in the organic light-emitting device, the first electrode can be an anode, the second electrode can be a cathode, and the organic layer can further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode. The hole transport region can include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer or any combination thereof, and the electron transport region can include a hole blocking layer, an electron transport layer, an electron injection layer or any combination thereof.

[0199] In embodiments, the emitting layer may comprise a heterocyclic compound represented by Formula 1. In addition to the heterocyclic compound, the emitting layer may further comprise a host, and the amount of the heterocyclic compound in the emitting layer may be less than the amount of the host. For example, the heterocyclic compound may be a thermally activated delayed fluorescence emitter (TADF emitter), but embodiments of this disclosure are not limited thereto.

[0200] In one or more embodiments, the phosphorescent compound (e.g., a transition metal compound) may not be included in the emission layer (e.g., it may be excluded from the emission layer), and for example, the emission layer may contain a heterocyclic compound represented by Formula 1 and a host.

[0201] In one or more embodiments, at least one of the hole transport region and the emitter layer may comprise at least one of an arylamine-containing compound, an acridine-containing compound, and a carbazole-containing compound; and / or

[0202] At least one of the emitter layer and the electron transport region may contain at least one of the following: a silicon-containing compound, a phosphine oxide-containing compound, a sulfur oxide-containing compound, a phosphorus oxide-containing compound, a triazine-containing compound, a pyrimidine-containing compound, a pyridine-containing compound, a dibenzofuran-containing compound, and a dibenzothiophene-containing compound.

[0203] [ Figure 1 [Description]

[0204] Figure 1 This is a schematic view of an organic light-emitting device 10 according to an embodiment. The organic light-emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.

[0205] In the following text, we will discuss... Figure 1 The structure of the organic light-emitting device 10 according to the embodiment and the method of manufacturing the organic light-emitting device 10 are described.

[0206] [First Electrode 110]

[0207] refer to Figure 1 The substrate may additionally be located below the first electrode 110 and / or above the second electrode 190. The substrate may be a glass substrate and / or a plastic substrate, each possessing excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and / or water resistance.

[0208] The first electrode 110 can be formed by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 can be selected from materials with high work function to facilitate hole injection.

[0209] The first electrode 110 can be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material used to form the first electrode can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof, but the embodiments of this disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transparent electrode or a reflective electrode, the material used to form the first electrode can be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but the embodiments of this disclosure are not limited thereto.

[0210] The first electrode 110 may have a single-layer structure or a multi-layer structure comprising multiple layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited to this.

[0211] [Organic layer 150]

[0212] The organic layer 150 is located on the first electrode 110. The organic layer 150 may include an emitter layer.

[0213] The organic layer 150 may further include a hole transport region between the first electrode 110 and the emitter layer and an electron transport region between the emitter layer and the second electrode 190.

[0214] [Hole transport region in organic layer 150]

[0215] The hole transport region may have i) a single-layer structure comprising a single layer of a single material, ii) a single-layer structure comprising a single layer of multiple different materials, or iii) a multi-layer structure comprising multiple layers of multiple different materials.

[0216] The hole transport region may include at least one layer selected from the hole injection layer, hole transport layer, emission assist layer and electron blocking layer.

[0217] For example, the hole transport region may have a single-layer structure including a single layer containing a variety of different materials, or a multi-layer structure including a hole injection layer / hole transport layer, a hole injection layer / hole transport layer / emission auxiliary layer, a hole injection layer / emission auxiliary layer, a hole transport layer / emission auxiliary layer, or a hole injection layer / hole transport layer / electron blocking layer, wherein the constituent layers of each structure are stacked sequentially from the first electrode 110 in their respective prescribed order, but the structure of the hole transport region is not limited to this.

[0218] The hole transport region may contain at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), CzSi, TCTA, compounds represented by Formula 201, and compounds represented by Formula 202:

[0219]

[0220]

[0221] Formula 201

[0222]

[0223] Formula 202

[0224]

[0225] In equations 201 and 202,

[0226] L 201 To L 204 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 arylene groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0227] L 205 It can be selected from *-O-*', *-S-*', *-N(Q) 201 )-*', substituted or unsubstituted C1-C 20 alkylene groups, substituted or unsubstituted C2-C 20 alkenyl groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 arylene groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0228] xa1 to xa4 can each be an integer from 0 to 3 independently.

[0229] xa5 can be an integer from 1 to 10, and

[0230] R 201 To R 204 and Q 201 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.

[0231] For example, in equation 202, R 201 and R 202 They can optionally be linked to each other via single bonds, dimethyl-methylene groups, or diphenyl-methylene groups, and R 203 and R 204 They can be optionally linked together via single bonds, dimethyl-methylene groups, or diphenyl-methylene groups.

[0232] In one implementation, in formulas 201 and 202,

[0233] L 201 To L 205 Each can be selected independently from:

[0234] Phenylidene group, pentylene group, indenyl group, naphthyl group, chamomile cycloyl group, heptylene group, adamantyl group, acenaphthene group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenanthroline group, anthracene group, fluorenyl group, benzo[a]phenanthrene group, pyrene group, etc. Benzyl group, tetraphenyl group, puryl group, peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, rubidyl group, styrenyl group, furanyl group, carbazolyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzothiophenyl group and pyridylyl group; and

[0235] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1-C10 Alkyl-substituted phenyl groups, -F-substituted phenyl groups, pentanenyl groups, indole groups, naphthyl groups, chamomile cycloyl groups, heptenyl groups, indoleyl groups, acenaphthyl groups, fluorenyl groups, spiro-difluorenyl groups, benzo[a]fluorenyl groups, dibenzo[a]fluorenyl groups, phenanthrenyl groups, anthraceneyl groups, fluoranthraceneyl groups, benzo[a]phenanthreneyl groups, pyrene groups, Benzyl group, tetraphenyl group, furanyl group, perylyl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, rutinyl group, kosyl group, ovoidyl group, thiophenyl group, furanyl group, carbazoleyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group, dibenzocarbazoleyl group, dibenzothiophenyl group, pyridyl group, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 At least one substituted phenylene group, pentylene group, indenyl group, naphthyl group, chamomile cycloyl group, heptylene group, adamantyl group, acenaphthene group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenenthene group, anthracene group, fluorenyl group, benzo[a]phenanthrene group, pyrene group, etc. The following groups are listed: benzo[a]benzyl group, benzo[a]benzyl group, benzo[a]benzyl group, pentaphenyl group, benzo[a]hexaphenyl group, benzo[a]pentaphenyl group, benzo[a]benzyl group, benzo[a]benzyl group, benzo[a]benzyl group, benzo[a]benzyl group, benzo[a]benzyl group, benzo[a]benzyl group, benzo[a]benzyl group, benzo[a]benzyl group, benzo[a]benzyl group, benzo[a]benzyl group, benzo[a]thio[a]benzyl group, benzo[a]thio[a]benzyl group, benzo[a]thio[a]benzyl group, benzo[a]thio[a]benzyl group, and pyridyl group.

[0236] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl groups, C1-C 10 Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups.

[0237] In one or more implementations, xa1 to xa4 can each be 0, 1 or 2 independently.

[0238] In one or more implementations, xa5 can be 1, 2, 3 or 4.

[0239] In one or more implementations, R 201 To R 204 and Q 201 Each group can be independently selected from: phenyl group, biphenyl group, terphenyl group, pentanenyl group, indole group, naphthyl group, chamomile cycloyl group, heptenyl group, indoleyl group, acenaphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthyl group, anthraceneyl group, fluoranthraceneyl group, benzo[a]phenanthryl group, pyrene group, etc. Benzyl group, tetraphenyl group, furanyl group, perylyl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, rutinyl group, kosyl group, ovoidyl group, thiophenyl group, furanyl group, carbazoleyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group, dibenzocarbazoleyl group, dibenzothiophenyl group and pyridyl group; and

[0240] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 10 Alkyl-substituted phenyl groups, -F-substituted phenyl groups, pentanenyl groups, indole groups, naphthyl groups, chamomile cycloyl groups, heptenyl groups, indoleyl groups, acenaphthyl groups, fluorenyl groups, spiro-difluorenyl groups, benzo[a]fluorenyl groups, dibenzo[a]fluorenyl groups, phenanthrenyl groups, anthraceneyl groups, fluoranthraceneyl groups, benzo[a]phenanthreneyl groups, pyrene groups, Benzyl group, tetraphenyl group, furanyl group, perylyl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, rutinyl group, kosyl group, ovoidyl group, thiophenyl group, furanyl group, carbazoleyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group, dibenzocarbazoleyl group, dibenzothiophenyl group, pyridyl group, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32At least one substituted phenyl group, biphenyl group, terphenyl group, pentanenyl group, indole group, naphthyl group, chamomile cycloyl group, heptenyl group, indoleyl group, acenaphthenic group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthreneyl group, anthraceneyl group, fluoranthraceneyl group, benzo[a]phenanthreneyl group, pyreneyl group, The following groups are listed: alkyl group, tetraphenyl group, furanyl group, perylyl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, rutinyl group, kosyl group, ovoidyl group, thiophenyl group, furanyl group, carbazoleyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group, dibenzocarbazoleyl group, dibenzothiophenyl group, and pyridyl group.

[0241] Q 31 To Q 33 Each can be independently identical to the descriptions above.

[0242] In one or more embodiments, R selected from Formula 201 201 To R 203 At least one of them can be independently selected from:

[0243] Fluorenyl group, spiro-difluorenyl group, carbazole group, dibenzofuranyl group and dibenzothiophenyl group; and

[0244] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 10 At least one substituted fluorenyl group, spiro-difluorenyl group, carbazole group, dibenzofuranyl group, and dibenzothiophene group selected from the following groups: alkyl-substituted phenyl group, -F-substituted phenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, carbazole group, dibenzofuranyl group, and dibenzothiophene group.

[0245] However, the implementation of this disclosure is not limited to this.

[0246] In one or more implementations, in formula 202, i)R 201 and R 202 They can be connected to each other via a single key, and / or ii)R 203 and R 204They can be connected to each other via a single key.

[0247] In one or more embodiments, R in formula 202 201 To R 204 Each can be selected independently from:

[0248] Carbazolium group; and

[0249] Selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 10 At least one substituted carbazoyl group selected from the following groups: alkyl-substituted phenyl group, -F-substituted phenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, carbazoyl group, dibenzofuranyl group, and dibenzothiophenyl group.

[0250] However, the implementation of this disclosure is not limited to this.

[0251] The compound represented by formula 201 can be represented by formula 201-1:

[0252] Formula 201-1

[0253]

[0254] In one embodiment, the compound represented by formula 201 may be represented by formula 201-2, but the embodiments of this disclosure are not limited thereto:

[0255] Formula 201-2

[0256]

[0257] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201-2(1), but the embodiments of this disclosure are not limited thereto:

[0258] Equation 201-2(1)

[0259]

[0260] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A:

[0261] Formula 201A

[0262]

[0263] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A(1), but the embodiments of this disclosure are not limited thereto:

[0264] Formula 201A(1)

[0265]

[0266] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A-1, but the embodiments of this disclosure are not limited thereto:

[0267] Formula 201A-1

[0268]

[0269] In one embodiment, the compound represented by formula 202 can be represented by formula 202-1:

[0270] Formula 202-1

[0271]

[0272] In one or more embodiments, the compound represented by formula 202 can be represented by formula 202-1(1):

[0273] Equation 202-1(1)

[0274]

[0275] In one or more embodiments, the compound represented by formula 202 may be represented by formula 202A:

[0276] Formula 202A

[0277]

[0278] In one or more embodiments, the compound represented by formula 202 can be represented by formula 202A-1:

[0279] Formula 202A-1

[0280]

[0281] In equations 201-1, 201-2, 201-2(1), 201A, 201A(1), 201A-1, 202-1, 202-1(1), 202A, and 202A-1,

[0282] L 201 To L203 xa1 to xa3, xa5 and R 202 To R 204 Each can be independently identical to the descriptions above.

[0283] L 205 It can be selected from phenylene groups and fluorene groups.

[0284] X 211 It can be selected from O, S and N(R) 211 ),

[0285] X 212 It can be selected from O, S and N(R) 212 ),

[0286] R 211 and R 212 They can be independently related to R. 203 The same definition, and

[0287] R 213 To R 217 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 10 Alkyl-substituted phenyl groups, -F-substituted phenyl groups, pentanenyl groups, indole groups, naphthyl groups, chamomile cycloyl groups, heptenyl groups, indoleyl groups, acenaphthyl groups, fluorenyl groups, spiro-difluorenyl groups, benzo[a]fluorenyl groups, dibenzo[a]fluorenyl groups, phenanthrenyl groups, anthraceneyl groups, fluoranthraceneyl groups, benzo[a]phenanthreneyl groups, pyrene groups, The group includes benzo[a], tetraphenyl[b], furan[b], peryl[b], pentaphenyl[a], hexaphenyl[b], pentaphenyl[a], rutin[b], koj[b], ovoid[b], thiophen[b], furan[b], carbazo[b], indole[b], isoindole[b], benzofuran[b], benzothiophen[b], dibenzofuran[b], dibenzothiophen[b], benzocarbazo[b], dibenzocarbazo[b], dibenzothiophen[b], dibenzothiophen[b], and pyridyl[b]

[0288] The hole transport region may contain at least one compound selected from compounds HT1 to HT48, but embodiments of this disclosure are not limited thereto:

[0289]

[0290]

[0291]

[0292]

[0293]

[0294] The thickness of the hole transport region can be approximately to approximately For example, about to approximately When the hole transport region includes at least one selected from the hole injection layer and the hole transport layer, the thickness of the hole injection layer can be approximately to approximately And for example, about to approximately And the thickness of the hole transport layer can be approximately to approximately And for example, about to approximately When the thicknesses of the hole transport region, hole injection layer, and hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage.

[0295] The emission assist layer can increase the light emission efficiency of the device by compensating for the optical resonant distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block or reduce the flow of electrons from the electron transport region. The emission assist layer and the electron blocking layer can each independently contain the materials described above.

[0296] [p-dopant]

[0297] In addition to these materials, the hole transport region may further contain charge-generating materials to improve conductivity. The charge-generating materials may be uniformly or non-uniformly dispersed within the hole transport region.

[0298] The charge-generating material can be, for example, a p-doped agent.

[0299] In one embodiment, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of -3.5 eV or below -3.5 eV.

[0300] p-dopers may include at least one selected from quinone derivatives, metal oxides, and compounds containing cyano groups, but embodiments of this disclosure are not limited thereto.

[0301] For example, p-dopers may include at least one selected from the following: quinone derivatives (e.g., tetracyanoquinone dimethyl ether (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl ether (F4-TCNQ));

[0302] Metal oxides (e.g., tungsten oxide and / or molybdenum oxide);

[0303] 1,4,5,8,9,12-hexaazatriphenylene-hexamethylnitrile (HAT-CN); and

[0304] The compound represented by formula 221,

[0305] However, the implementation of this disclosure is not limited to this:

[0306]

[0307] Equation 221

[0308]

[0309] In Equation 221,

[0310] R 221 To R 223 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, wherein the group is selected from R 221 To R 223 At least one of them may have a C1-C group selected from cyano group, -F, -Cl, -Br, -I, or a C1-C group substituted with -F. 20 Alkyl groups, C1-C substituted with -Cl 20 Alkyl groups, C1-C substituted with -Br 20 Alkyl groups and C1-C substituted with -I 20 At least one substituent in an alkyl group.

[0311] [Emitting layer in organic layer 150]

[0312] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emitting layer can be patterned as a red emitting layer, a green emitting layer, or a blue emitting layer, depending on the sub-pixel. In one or more embodiments, the emitting layer may have a stacked structure of two or more layers selected from red, green, and blue emitting layers, wherein the two or more layers may be in contact with each other or may be spaced apart from each other. In one or more embodiments, the emitting layer may contain two or more materials selected from red-emitting materials, green-emitting materials, and blue-emitting materials, wherein the two or more materials are mixed with each other in a single layer to emit white light.

[0313] The emitter layer may comprise a host and a dopant. The dopant may comprise a heterocyclic compound represented by Formula 1.

[0314] In the emitter layer, based on 100 parts by weight of the host, the amount of dopant can be from about 0.01 parts by weight to about 30 parts by weight, but the embodiments of this disclosure are not limited thereto.

[0315] The thickness of the emission layer can be approximately to approximately For example, about to approximately When the thickness of the emitting layer is within these ranges, excellent light emission characteristics can be obtained without a significant increase in driving voltage.

[0316] [The main body in the emission layer]

[0317] In one or more embodiments, the body may include a compound represented by formula 301:

[0318] Formula 301

[0319] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21

[0320] In Equation 301,

[0321] Ar 301 It can be substituted or unsubstituted C5-C 60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups,

[0322] xb11 can be 1, 2, or 3.

[0323] L 301 It can be selected from substituted or unsubstituted C3-C 10Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 arylene groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0324] xb1 can be an integer from 0 to 5.

[0325] R 301 It can be selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C. 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -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 ) and -P(=O)(Q 301 (Q) 302 ),

[0326] xb21 can be an integer from 1 to 5, and

[0327] Q 301 To Q 303 Each can be independently selected from C1-C 10 Alkyl groups, C1-C 10 Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups, but embodiments of this disclosure are not limited thereto.

[0328] In one implementation, Ar in Formula 301 301 You can choose from:

[0329] Naphthalene group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[a]phenanthrene group, pyrene group, Groups, tetraphenyl groups, furan groups, perylene groups, pentaphenyl groups, indene-anthracene groups, dibenzofuran groups, and dibenzothiophene groups; and

[0330] Each is independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 At least one substituted naphthyl group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenatene group, anthracene group, fluoranthene group, benzo[a]phenanthrene group, pyrene group, Groups, tetraphenyl group, furan group, perylene group, pentaphenyl group, indene-anthracene group, dibenzofuran group and dibenzothiophene group,

[0331] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl groups, C1-C 10 Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups, but embodiments of this disclosure are not limited thereto.

[0332] When xb11 in equation 301 is 2 or greater than 2, there are two or more Ar... 301 It can be connected via a single key.

[0333] In one or more embodiments, the compound represented by formula 301 may be represented by formula 301-1 or formula 301-2:

[0334] Formula 301-1

[0335]

[0336] Formula 301-2

[0337]

[0338] In Equations 301-1 and 301-2,

[0339] A 301 To A 304 Each group can be independently selected from phenyl groups, naphthyl groups, phenanthrene groups, fluoranthene groups, benzo[a]phenanthrene groups, pyrene groups, etc. Groups, pyridine groups, pyrimidine groups, indene groups, fluorene groups, spiro-difluorene groups, benzo[a]fluorene groups, dibenzo[a]fluorene groups, indole groups, carbazole groups, benzo[a]carbazole groups, dibenzo[a]carbazole groups, furan groups, benzo[a]furan groups, dibenzo[a]furan groups, naphthofuran groups, benzo[a]naphthofuran groups, dinaphthofuran groups, thiophene groups, benzo[a]thiophene groups, dibenzo[a]thiophene groups, naphtho[a]thiophene groups, benzo[a]naphtho[a]thiophene groups, and dinaphtho[a]thiophene groups.

[0340] X 301 It can be O, S or N-[(L 304 ) xb4 -R 304 ],

[0341] R 311 To R 314 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q)31 ) and -P(=O)(Q 31 (Q) 32 ),

[0342] xb22 and xb23 can each be 0, 1, or 2 independently.

[0343] L 301 xb1, R 301 and Q 31 To Q 33 Each can be independently identical to the descriptions above.

[0344] L 302 To L 304 They can be independently related to L 301 The descriptions are the same.

[0345] xb2 to xb4 can each be independently identical to the description of xb1, and

[0346] R 302 To R 304 They can be independently related to R. 301 The descriptions are the same.

[0347] For example, in Equations 301, 301-1, and 301-2, L 301 To L 304 Each can be selected independently from:

[0348] Phenylidene group, naphthyl group, fluorenelidene group, spiro-difluorenelidene group, benzo[a]fluorenelidene group, dibenzo[a]fluorenelidene group, phenanthrenelidene group, anthracenelidene group, fluorenethracene group, benzo[a]phenanthrenelidene group, pyrene group, etc. Perylene group, pentaphenylene group, hexaphenylene group, pentaphenylene group, thiophene group, furanyl group, carbazolyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzothiophene group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiazolyl diazolyl group, oxadiazolyl group , pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolineyl group, isoquinolineyl group, benzoquinolineyl group, phthalazinyl group, naphridinyl group, quinoxalinyl group, quinoxalinyl group, phenanthrene-pyridinyl group, acridineyl group, phenanthrene-pyridinyl group, benzimidazoleyl group, isobenzothiazolyl group, benzimidazoleyl group, isobenzoxazoleyl group, isobenzoxazoleyl group, triazoleyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and zazacarbazolyl group; and

[0349] Each is independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group, triphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthrene group, anthracene group, fluoranthracene group, benzo[a]phenanthrene group, pyrene group, Peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, thiophene group, furanyl group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, pyridyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group Pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphridinyl group, quinoxalinyl group, quinazolinyl group, phenanthridineyl group, acridineyl group, phenanthroxolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, -Si(Q) 31 (Q)32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 At least one substituted phenylene group, naphthylene group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenanthrene group, anthracene group, fluorenyl anthracene group, benzo[a]phenanthrene group, pyrene group, etc. Perylene group, pentaphenylene group, hexaphenylene group, pentaphenylene group, thiophene group, furanyl group, carbazolyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzothiophene group, pyridylene group, imidazolyl group, pyrazolylene group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiazolyl diazolyl group, oxadiazolyl group The following groups are listed: pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolineyl group, isoquinolineyl group, benzo[a]quinolineyl group, phthalazinyl group, naphthidyl group, quinoxalinyl group, quinoxalinyl group, phenanthrene-pyridinyl group, acridineyl group, phenanthrene-pyridinyl group, benzimidazoleyl group, isobenzothiazolyl group, benzimidazoleyl group, isobenzoxazoleyl group, isobenzoxazoleyl group, triazoleyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and zazacarbazolyl group.

[0350] Q 31 To Q 33 Each can be independently identical to the descriptions above.

[0351] In one implementation, in formulas 301, 301-1, and 301-2, R 301 To R 304 Each can be selected independently from:

[0352] Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthryl group, anthraceneyl group, fluoranthraceneyl group, benzo[a]phenanthryl group, pyrene group, Peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, thiophene group, furanyl group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, pyridyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group Pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphridinyl group, quinoxalinyl group, quinazolinyl group, cyclophosphinyl group, phenanthridineyl group, acridineyl group, phenanthroxolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and azacarbazolyl group; and

[0353] Each is independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group, triphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthrene group, anthracene group, fluoranthracene group, benzo[a]phenanthrene group, pyrene group, Peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, thiophene group, furanyl group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, pyridyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group Pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphridinyl group, quinoxalinyl group, quinazolinyl group, phenanthridineyl group, acridineyl group, phenanthroxolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q)32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 At least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthryl group, anthraceneyl group, fluoranthraceneyl group, benzo[a]phenanthryl group, pyrene group, Peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, thiophene group, furanyl group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, pyridinyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group The following groups are listed: pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphridinyl group, quinoxalinyl group, quinazolinyl group, cyclophosphinyl group, phenanthridineyl group, acridineyl group, phenanthroxolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and azacarbazolyl group.

[0354] Q 31 To Q 33 Each can be independently identical to the descriptions above.

[0355] In one embodiment, the host may include an alkaline earth metal complex. For example, the host may be selected from Be complexes (e.g., compound H55) and Mg complexes. In some embodiments, the host may be a Zn complex.

[0356] The main component may include 9,10-bis(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), 9,10-bis-(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 3,3'-bis(9H-carbazolyl-9-yl)-1,1'-biphenyl (m-CBP), and 2,2'-bis(9H-carbazolyl-9-yl)biphenyl (o-CBP), 1,3-di-9-carbazolebenzene (mCP), 1,3,5-tris(carbazole-9-yl)benzene (TCP), bis(4-(9H-carbazole-9-yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenylphosphine oxide (POPCPA), DPEPO, and at least one of compounds H1 to H55, but embodiments of the present disclosure are not limited thereto:

[0357]

[0358]

[0359]

[0360] The subject can have any suitable modifications; for example, the subject can be contained in the form of a single compound, or it can be contained in the form of two or more different compounds.

[0361] [Dopant contained in the emitter layer of organic layer 150]

[0362] The dopant can be or includes heterocyclic compounds represented by Formula 1 as used herein. The heterocyclic compounds can be the same as those described above.

[0363] [Electron transport region in organic layer 150]

[0364] The electron transport region may have i) a single-layer structure comprising a single layer of a single material, ii) a single-layer structure comprising a single layer of multiple different materials, or iii) a multi-layer structure comprising multiple layers of multiple different materials.

[0365] The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but embodiments of the present disclosure are not limited thereto.

[0366] For example, the electron transport region can have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the constituent layers of each structure are stacked sequentially from the emitter layer. However, the implementation scheme of the electron transport region structure is not limited to this.

[0367] The electron transport region (e.g., a buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may contain a metal-free compound having a ring of nitrogen with at least one π electron depleted.

[0368] The term "a ring containing nitrogen with depleted π electrons" refers to a C1-C ring having at least one *-N=*' moiety as the cyclic part. 60 Heterocyclic groups.

[0369] For example, a "ring containing nitrogen with depleted π electrons" can be i) a 5- to 7-membered heterocyclic group having at least one *-N=*' moiety, ii) a heteropolycyclic group wherein two or more 5- to 7-membered heterocyclic groups, each having at least one *-N=*' moiety, are fused together, or iii) a 5- to 7-membered heterocyclic group having at least one *-N=*' moiety and at least one C5-C 60 A heterocyclic group with fused carbocyclic groups.

[0370] Non-limiting examples of nitrogen rings containing depleted π electrons include imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthidine, quinoxaline, quinazoline, cyclophosphine, phenanthridine, acridine, phenanthridine, phenazine, benzimidazole, isobenzothiazole, benzoxazole, isobenzoxazole, triazole, tetraazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole.

[0371] In some implementations, for example, the electron transport region may comprise a compound represented by formula 601:

[0372] Formula 601

[0373] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21

[0374] In Equation 601,

[0375] Ar 601 It can be substituted or unsubstituted C5-C 60The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups,

[0376] xe11 can be 1, 2, or 3.

[0377] L 601 It can be selected from substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 arylene groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0378] xe1 can be an integer from 0 to 5.

[0379] R 601 It can be selected from substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -Si(Q 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q) 601 ) and -P(=O)(Q 601 (Q) 602 ),

[0380] Q 601 To Q 603 Each can be C1-C independently. 10 Alkyl groups, C1-C 10 Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, or naphthyl groups, and

[0381] xe21 can be an integer from 1 to 5.

[0382] In one implementation, xe11 Ar 601 and xe21 R 601 At least one of them may contain a ring of nitrogen with depleted π electrons.

[0383] In one implementation, Ar in Formula 601 601 You can choose from:

[0384] Phenyl group, naphthyl group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[a]phenanthrene group, pyrene group, Groups, tetraphenyl group, styrene group, perylene group, pentaphenyl group, indene-anthracene group, dibenzofuran group, dibenzothiophene group, carbazole group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthidine group, quinoxaline group, quinazolinoline group, cyclophosphine group, phenanthridine group, acridine group, phenanthrene-rhein group, phenazine group, benzimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetraazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group and azacarbazole group; and

[0385] Each is independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q) 31 (Q) 32 (Q) 33 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 At least one substituted phenyl group, naphthyl group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[a]phenanthrene group, pyrene group, Groups, tetraphenyl group, styrene group, perylene group, pentaphenyl group, indene-anthracene group, dibenzofuran group, dibenzothiophene group, carbazole group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthidine group, quinoxaline group, quinazoline group, cinnamicin group, phenanthridine group, acridine group, phenanthrene-rhein group, phenazine group, benzimidazole group, isobenzothiazole group, benzooxazole group, isobenzooxazole group, triazole group, tetraazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, and azacarbazole group,

[0386] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl groups, C1-C 10 Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups.

[0387] When xe11 in equation 601 is 2 or greater than 2, there are two or more Ar... 601 They can be connected to each other via a single key.

[0388] In one or more embodiments, Ar in Formula 601 601 It can be an anthracene group.

[0389] In one or more embodiments, the compound represented by formula 601 may be represented by formula 601-1:

[0390] Formula 601-1

[0391]

[0392] In Equation 601-1,

[0393] X 614 It can be N or C(R) 614 ), X 615 It can be N or C(R) 615 ), X 616 It can be N or C(R) 616 ), and selected from X 614 To X 616 At least one of them can be N,

[0394] L 611 To L 613 They can be independently related to L 601 The descriptions are the same.

[0395] xe611 to xe613 can each be independently defined as being the same as xe1.

[0396] R 611 To R 613 They can be independently related to R. 601 The same description, and

[0397] R 614 To R 616 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups.

[0398] In one implementation, L in Formula 601 and Formula 601-1 601 and L 611 To L 613 Each can be selected independently from:

[0399] Phenylidene group, naphthyl group, fluorenelidene group, spiro-difluorenelidene group, benzo[a]fluorenelidene group, dibenzo[a]fluorenelidene group, phenanthrenelidene group, anthracenelidene group, fluorenethracene group, benzo[a]phenanthrenelidene group, pyrene group, etc. Perylene group, pentaphenylene group, hexaphenylene group, pentaphenylene group, thiophene group, furanyl group, carbazolyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzothiophene group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiazolyl diazolyl group, oxadiazolyl group , pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolineyl group, isoquinolineyl group, benzoquinolineyl group, phthalazinyl group, naphridinyl group, quinoxalinyl group, quinoxalinyl group, phenanthrene-pyridinyl group, acridineyl group, phenanthrene-pyridinyl group, benzimidazoleyl group, isobenzothiazolyl group, benzimidazoleyl group, isobenzoxazoleyl group, isobenzoxazoleyl group, triazoleyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and zazacarbazolyl group; and

[0400] Each is independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group, triphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthrene group, anthracene group, fluoranthracene group, benzo[a]phenanthrene group, pyrene group, Peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, thiophene group, furanyl group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, pyridyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinoline At least one substituted phenylene group, naphthidyl group, quinoxalinyl group, quinazolinyl group, phenanthrynyl group, acridineyl group, phenanthrolineyl group, phenazinyl group, benzimidazole group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazole group, tetrazolyl group, imidazopyridyl group, imidazopyrimidyl group, and azacarbazolyl group, naphthylene group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenanthrene group, anthracene group, fluorenyl anthracene group, benzo[a]phenanthrene group, pyrene group, etc., selected from the following groups: phenylene group, naphthylene group, naphthylene group, benzo[a]phenanthrene group, pyrene group, etc. Perylene group, pentaphenylene group, hexaphenylene group, pentaphenylene group, thiophene group, furanyl group, carbazolyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzothiophene group, pyridylene group, imidazolyl group, pyrazolylene group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiazolyl diazolyl group, oxadiazolyl group The following groups are listed: pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolineyl group, isoquinolineyl group, benzo[a]quinolineyl group, phthalazinyl group, naphthidyl group, quinoxalinyl group, quinoxalinyl group, phenanthrene-pyridinyl group, acridineyl group, phenanthrene-pyridinyl group, benzimidazoleyl group, isobenzothiazolyl group, benzimidazoleyl group, isobenzoxazoleyl group, isobenzoxazoleyl group, triazoleyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and zazacarbazolyl group.

[0401] However, the implementation of this disclosure is not limited to this.

[0402] In one or more embodiments, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 can each be 0, 1 or 2 independently.

[0403] In one or more embodiments, R in Formula 601 and Formula 601-1 601 and R 611 To R 613 Each can be selected independently from:

[0404] Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthryl group, anthraceneyl group, fluoranthraceneyl group, benzo[a]phenanthryl group, pyrene group, Peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, thiophene group, furanyl group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, pyridinyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group Groups, including pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphridinyl group, quinoxalinyl group, quinazolinyl group, cyclophosphinyl group, phenanthridineyl group, acridineyl group, phenanthroxolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and azacarbazolyl group;

[0405] Each is independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group, triphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthrene group, anthracene group, fluoranthracene group, benzo[a]phenanthrene group, pyrene group, Peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, thiophene group, furanyl group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, pyridyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinoline The following groups are substituted with at least one of the following groups: phthalazinyl group, naphthidyl group, quinoxalinyl group, quinazolinyl group, phenanthrynyl group, acridineyl group, phenanthrolineyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridyl group, imidazopyrimidyl group, and azacarbazolyl group; a substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[fluorenyl]fluorenyl group, dibenzo[fluorenyl]fluorenyl group, phenanthrene group, anthraceneyl group, fluoranthraceneyl group, benzo[phenanthreneyl]pyrene group. Peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, thiophene group, furanyl group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, pyridyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group Pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphridinyl group, quinoxalinyl group, quinazolinyl group, cyclophosphinyl group, phenanthridineyl group, acridineyl group, phenanthroxolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and azacarbazolyl group; and

[0406] -S(=O)2(Q 601 ) and -P(=O)(Q 601 (Q) 602 ),

[0407] Q 601 and Q 602 Each can be independently identical to the descriptions above.

[0408] The electron transport region may contain at least one compound selected from compounds ET1 to ET36, but embodiments of this disclosure are not limited thereto:

[0409]

[0410]

[0411]

[0412]

[0413] In one or more embodiments, the electron transport region may comprise at least one compound selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), NTAZ, diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1), TPBI, and DPEPO.

[0414]

[0415]

[0416] The thicknesses of the buffer layer, hole blocking layer, and electronic control layer can each be approximately [missing information]. to approximately For example, about to approximately When the thicknesses of the buffer layer, hole blocking layer, and electronic control layer are each within these ranges, the hole blocking layer or electronic control layer can have excellent hole blocking or electronic control characteristics without a significant increase in driving voltage.

[0417] The thickness of the electron transport layer can be approximately to approximately For example, about to approximately When the thickness of the electron transport layer is within the range described above, the electron transport layer can have satisfactory electron transport characteristics without a significant increase in driving voltage.

[0418] In addition to the materials described above, the electron transport region (e.g., the electron transport layer in the electron transport region) may further contain a metallic material.

[0419] The metal-containing material may include at least one selected from alkali metal complexes and alkaline earth metal complexes. Alkali metal complexes may contain metal ions selected from lithium (Li) ions, sodium (Na) ions, potassium (K) ions, rubidium (Rb) ions, and cesium (Cs) ions, and alkaline earth metal complexes may contain metal ions selected from beryllium (Be) ions, magnesium (Mg) ions, calcium (Ca) ions, strontium (Sr) ions, and barium (Ba) ions. The ligand coordinating with the metal ions of the alkali metal complex or alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenidine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but embodiments of this disclosure are not limited thereto.

[0420] For example, metal-containing materials may include Li complexes. Li complexes may include, for example, compounds ET-D1 (lithium hydroxyquinoline, LiQ) or ET-D2:

[0421]

[0422] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.

[0423] The electron injection layer can have i) a single-layer structure comprising a single layer containing a single material, ii) a single-layer structure comprising a single layer containing multiple different materials, or iii) a multi-layer structure comprising multiple layers containing multiple different materials.

[0424] The electron injection layer may contain alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof.

[0425] The alkali metal can be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal can be Li, Na, or Cs. In one or more embodiments, the alkali metal can be Li or Cs, but the embodiments of this disclosure are not limited thereto.

[0426] Alkaline earth metals can be selected from Mg, Ca, Sr, and Ba.

[0427] Rare earth metals can be selected from scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb), and gadolinium (Gd).

[0428] The alkali metal compound, alkaline earth metal compound, and rare earth metal compound can each independently be selected from oxides and halides (e.g., fluorides, chlorides, bromides, and / or iodides) of alkali metals, alkaline earth metals, and rare earth metals.

[0429] The alkali metal compound can be selected from alkali metal oxides (e.g., Li2O, Cs2O, and / or K2O) and alkali metal halides (e.g., LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, and / or RbI). In one embodiment, the alkali metal compound can be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, but the embodiments of the present disclosure are not limited thereto.

[0430] The alkaline earth metal compound can be selected from alkaline earth metal oxides (e.g., BaO, SrO, CaO, Ba x Sr 1-x O(0 < x < 1) and / or Ba x Ca 1-x O(0 < x < 1)). In one embodiment, the alkaline earth metal compound can be selected from BaO, SrO, and CaO, but the embodiments of the present disclosure are not limited thereto.

[0431] The rare earth metal compound can be selected from YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, and TbF3. In one embodiment, the rare earth metal compound can be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but the embodiments of the present disclosure are not limited thereto.

[0432] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex can respectively contain ions of alkali metals, alkaline earth metals, and rare earth metals as described above, and the ligands coordinated with the metal ions of the alkali metal complex, alkaline earth metal complex, or rare earth metal complex can be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.

[0433] The electron-injection layer may comprise (e.g., constituted by): alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof as described above. In one or more embodiments, the electron-injection layer may further comprise an organic material. When the electron-injection layer further comprises an organic material, the alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or combinations thereof may be uniformly or non-uniformly dispersed in the matrix comprising the organic material.

[0434] The thickness of the electron injection layer can be approximately to approximately For example, about to approximately When the thickness of the electron injection layer is within the range described above, the electron injection layer can have satisfactory electron injection characteristics without a significant increase in driving voltage.

[0435] [Second electrode 190]

[0436] The second electrode 190 can be disposed on the organic layer 150 having such a structure. The second electrode 190 can be a cathode serving as an electron injection electrode, and in this respect, the material used to form the second electrode 190 can be selected from metals, alloys, conductive compounds, and combinations thereof, each having a relatively low work function.

[0437] The second electrode 190 may contain at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, and IZO, but embodiments of this disclosure are not limited thereto. The second electrode 190 may be a transmission electrode, a semi-transmission electrode, or a reflection electrode.

[0438] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.

[0439] [ Figures 2 to 4 [Description]

[0440] Figure 2 This is a schematic view of an organic light-emitting device 20 according to an embodiment. The organic light-emitting device 20 includes a first cover layer 210, a first electrode 110, an organic layer 150, and a second electrode 190, which are stacked in this prescribed order. Figure 3This is a schematic view of an organic light-emitting device 30 according to an embodiment. The organic light-emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second cover layer 220, which are stacked in this prescribed order. Figure 4 This is a schematic view of an organic light-emitting device 40 according to an embodiment. The organic light-emitting device 40 includes a first cover layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second cover layer 220, which are stacked in this prescribed order.

[0441] about Figures 2 to 4 The first electrode 110, the organic layer 150, and the second electrode 190 can each independently interact with the electrode. Figure 1 The descriptions are the same.

[0442] In the organic layer 150 of each of the organic light-emitting devices 20 and 40, light generated in the emitting layer can pass outward through the first electrode 110 and the first capping layer 210, and the first electrode 110 can be a semi-transparent electrode or a transmissive electrode. In the organic layer 150 of each of the organic light-emitting devices 30 and 40, light generated in the emitting layer can pass outward through the second electrode 190 and the second capping layer 220, and the second electrode 190 can be a semi-transparent electrode or a transmissive electrode.

[0443] The first cover layer 210 and the second cover layer 220 can each increase the external luminous efficiency of the device according to the principle of constructive interference.

[0444] The first capping layer 210 and the second capping layer 220 can each be an organic capping layer containing organic materials, an inorganic capping layer containing inorganic materials, or a composite capping layer containing both organic and inorganic materials.

[0445] At least one of the first capping layer 210 and the second capping layer 220 may each independently comprise at least one material selected from carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphyrin derivatives, phthalocyanine derivatives, naphthylphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds, and amine-based compounds may each be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one of the first capping layer 210 and the second capping layer 220 may each independently comprise an amine-based compound.

[0446] In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently contain a compound represented by formula 201 and / or a compound represented by formula 202.

[0447] In one or more embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently comprise a compound selected from compounds HT28 to HT33 and compounds CP1 to CP5, but the embodiments of this disclosure are not limited thereto:

[0448]

[0449] In the above text, we have already discussed... Figures 1 to 4 An organic light-emitting device according to an embodiment is described, but the embodiments of this disclosure are not limited thereto.

[0450] The layers constituting the hole transport region, the emission layer, and the electron transport region can each be formed in the designated or predetermined region using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.

[0451] When the layers constituting the hole transport region, the emitter layer, and the electron transport region are each formed by vacuum deposition, the deposition temperature can be from about 100°C to about 500°C, depending on the material to be included in the layers to be formed and the structure of the layers to be formed, and the deposition time can be from about 10°C to about 500°C. -8 To about 10 -3 The vacuum degree and about to approximately Deposition occurs at a certain deposition rate.

[0452] When the layers constituting the hole transport region, the emitter layer, and the electron transport region are formed by spin coating, depending on the material to be included in the layers to be formed and the structure of the layers to be formed, spin coating can be performed at a coating rate of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80°C to 200°C.

[0453] [equipment]

[0454] Organic light-emitting devices can be included in any suitable equipment.

[0455] In an exemplary embodiment, the thin-film transistor device may include a source electrode, a drain electrode, and an active layer; and an organic light-emitting device. For example, a first electrode of the organic light-emitting device may be in electrical contact with one of the source electrode or the drain electrode of the thin-film transistor.

[0456] Thin-film transistors may further include gate electrodes, gate insulating layers, etc.

[0457] The active layer may include crystalline silicon, amorphous silicon, organic semiconductors, oxide semiconductors, etc., but the embodiments disclosed herein are not limited to these.

[0458] The device may further include a sealing component for sealing the organic light-emitting device. The sealing component allows imaging from the organic light-emitting device and can block or reduce the penetration of external air and / or moisture into the organic light-emitting device. The sealing component may be a sealing substrate comprising a transparent glass and / or a plastic substrate. The sealing component may be a thin-film encapsulation layer comprising multiple organic layers and / or multiple inorganic layers. When the sealing component is a thin-film encapsulation layer, the entire device can be flexible.

[0459] For example, the device can be a light-emitting device, a verification device, or an electronic device.

[0460] Light-emitting devices can be used as any suitable display, light source, etc.

[0461] The verification device can be, for example, a biometric verification device for verifying an individual using biometric information from a biometric body (e.g., fingertip, pupil, etc.). In addition to an organic light-emitting device, the verification device may further include a biometric information collector.

[0462] Electronic devices can be applied to personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, video game consoles, medical instruments (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram (ECG) displays, ultrasound diagnostic devices, or endoscopic displays), fish finders, various measuring instruments, meters (e.g., instruments for vehicles, aircraft, and ships), projectors, etc., but embodiments of this disclosure are not limited thereto.

[0463] [General definition of substituents]

[0464] As used in this article, the term "C1-C" 60 "alkyl group" refers to a straight-chain or branched monovalent aliphatic saturated hydrocarbon group having 1 to 60 carbon atoms, and non-limiting examples include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl groups. In some embodiments, C1-C 60 Alkyl groups can be C1-C 30 Alkyl groups, C1-C 20 alkyl groups or C1-C 10 Alkyl groups. As used in this document, "C1-C..." 60 "alkylene group" refers to a group that has a C1-C2 bond structure. 60 Alkyl groups are divalent groups with essentially the same structure.

[0465] As used in this article, the term "C2-C" 60"Alkenyl group" refers to the group located at C2-C. 60 The alkyl group is a hydrocarbon group having at least one carbon-carbon double bond at its middle or end, and non-limiting examples include vinyl groups, propenyl groups, and butenyl groups. In some embodiments, C2-C 60 The alkenyl group can be C2-C 30 alkenyl groups, C2-C 20 alkenyl groups or C2-C 10 Alkenyl group. As used in this article, "C2-C" 60 "Ideinyl group" refers to a group that has a C2-C... 60 Alkenyl groups are divalent groups with essentially the same structure.

[0466] As used in this article, the term "C2-C" 60 "Alkyne group" refers to the group located at C2-C. 60 The alkyl group is a hydrocarbon group having at least one carbon-carbon triple bond at its middle or end, and non-limiting examples include ethynyl and propynyl groups. In some embodiments, C2-C 60 The alkynyl group can be C2-C 30 alkynyl group, C2-C 20 alkynyl group or C2-C 10 Alkynyl group. As used in this article, "C2-C" 60 "Imyynyl group" refers to a group that has a C2-C... 60 Alkyne groups are divalent groups with essentially the same structure.

[0467] As used in this article, the term "C1-C" 60 "Alkoxy group" refers to the group consisting of -OA 101 (where A) 101 It is C1-C 60 The alkyl group is a monovalent group, and non-limiting examples of it include methoxy groups, ethoxy groups and isopropoxy groups.

[0468] As used in this article, the term "C3-C" 10 "Cycloalkyl group" refers to a monocyclic saturated hydrocarbon group having 3 to 10 carbon atoms, and non-limiting examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl groups. As used herein, the term "C3-C" is also relevant. 10 "Cycloalkylene group" refers to a group that has a C3-C6 bond structure. 10 Cycloalkyl groups are divalent groups with essentially the same structure.

[0469] As used in this article, the term "C1-C" 10"Heterocyclic alkyl group" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as the cyclic atom (e.g., 1 to 5 or 1 to 3 heteroatoms, such as 1, 2, 3, 4, or 5 heteroatoms) and 1 to 10 carbon atoms, and non-limiting examples include 1,2,3,4-oxatriazole alkyl groups, tetrahydrofuranyl groups, and tetrahydrothiophenyl groups. The term "C1-C" as used herein is also relevant. 10 "Heterocyclic alkyl groups" refers to groups with C1-C2 groups. 10 Heterocyclic alkyl groups are divalent groups with essentially the same structure.

[0470] As used in this article, the term "C3-C" 10 "Cycloalenyl group" refers to a monovalent monocyclic group having 3 to 10 carbon atoms in its ring, at least one carbon-carbon double bond, and no aromaticity, and non-limiting examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl groups. As used herein, the term "C3-C" is also relevant. 10 "Iridyl group" refers to a group that has a C3-C6 bond structure. 10 Cycloalkenyl groups are divalent groups with essentially the same structure.

[0471] As used in this article, the term "C1-C" 10 A "heterocyclic alkenyl group" refers to a monovalent monocyclic group having at least one heteroatom (e.g., 1 to 5 or 1 to 3 heteroatoms, such as 1, 2, 3, 4 or 5 heteroatoms) selected from N, O, Si, P and S as cyclic atoms, 1 to 10 carbon atoms, and at least one double bond in its ring. C1-C 10 Non-limiting examples of heterocyclic alkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl groups. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl group" refers to a group that has a C1-C2 bond structure. 10 Heterocyclic alkenyl groups are divalent groups with essentially the same structure.

[0472] As used in this article, the term "C6-C" 60 "Aryl group" refers to a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms, and as used herein, "C6-C..." 60 "Aromatic group" refers to a divalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms. In some embodiments, C6-C 60 The aryl group can be C6-C. 30 aryl group, C6-C 24 aryl group or C6-C 18 Aryl group. C6-C 60Non-limiting examples of aryl groups include phenyl groups, naphthyl groups, anthracene groups, phenanthrene groups, pyrene groups, and... Basic group. When C6-C 60 aryl groups and C6-C 60 When each of the aryl groups comprises two or more rings, the rings may be fused together.

[0473] As used in this article, the term "C7-C" 60 An "aryl group" refers to a group having 7 to 60 carbon atoms in which the alkyl group is replaced by an aryl group. (C7-C) 60 Non-limiting examples of aryl groups include benzyl groups, etc. In some embodiments, C7-C 60 Aryl groups can be C7-C 31 Aryl groups, C7-C 25 Aryl groups or C7-C 19 Aryl group.

[0474] As used in this article, the term "C1-C" 60 A "heteroaryl group" refers to a monovalent group in a carbocyclic aromatic system having at least one heteroatom (e.g., 1 to 5 or 1 to 3 heteroatoms, such as 1, 2, 3, 4, or 5 heteroatoms) selected from N, O, Si, P, and S as cyclic atoms, in addition to 1 to 60 carbon atoms. The term "C1-C" is used herein. 60 A "hybrid aryl group" refers to a divalent group in a carbocyclic aromatic system having at least one heteroatom (e.g., 1 to 5 or 1 to 3 heteroatoms, such as 1, 2, 3, 4, or 5 heteroatoms) selected from N, O, Si, P, and S as cyclic atoms, in addition to 1 to 60 carbon atoms. C1-C 60 Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl groups. In some embodiments, C1-C 60 The heteroaryl group can be C1-C 30 heteroaryl groups, C1-C 24 heteroaryl groups or C1-C 18 heteroaryl groups. When C1-C 60 heteroaryl groups and C1-C 60 When each of the heteroaryl groups comprises two or more rings, the rings can be fused together.

[0475] As used in this article, the term "C2-C" 60 "Heteroarylene alkyl group" refers to a group having 2 to 60 carbon atoms in which the alkyl group is replaced by a heteroarylene group. In some embodiments, C2-C 60The heteroaryl group can be C2-C 31 heteroaryl groups, C2-C 25 heteroaryl groups or C2-C 19 Heteroaryl groups.

[0476] As used in this article, the term "C6-C" 60 "Aryloxy group" refers to -OA 102 (where A) 102 It is C6-C 60 (aryl group), and as used herein by the term "C6-C" 60 "Aryl thio group" indicates -SA 103 (where A) 103 It is C6-C 60 (aryl group).

[0477] As used in this article, the term "C1-C" 60 "Heteroaryloxy group" refers to the group composed of -OA 104 (where A) 104 It is C1-C 60 Monovalent groups (represented by heteroaryl groups), and as used herein by the term "C1-C" 60 "Heteroary sulfide group" refers to -SA 105 (where A) 105 It is C1-C 60 (Heteroaryl groups).

[0478] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group having two or more rings fused together, with only carbon atoms as cyclic atoms (e.g., 8 to 60 carbon atoms, such as 8 to 30 or 8 to 24 carbon atoms), and lacking aromaticity throughout its molecular structure. A non-limiting example of a monovalent nonaromatic fused polycyclic group is the fluorene group. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having a structure substantially the same as that of a monovalent nonaromatic fused polycyclic group.

[0479] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a group having two or more rings fused together, with at least one heteroatom selected from N, O, Si, P, and S (e.g., 1 to 5 or 1 to 3 heteroatoms, e.g., 1, 2, 3, 4, or 5 heteroatoms) as a cyclic atom other than carbon atoms (e.g., 1 to 60 carbon atoms, such as 1 to 30 or 1 to 24 carbon atoms) as a cyclic atom, and without aromaticity throughout its molecular structure. A non-limiting example of a monovalent nonaromatic fused heterocyclic group is the carbazoyl group. As used herein, the term "divalent nonaromatic fused heterocyclic group" refers to a divalent group having a structure substantially the same as that of a monovalent nonaromatic fused heterocyclic group.

[0480] As used in this article, the term "C5-C" 60 A "carbocyclic group" refers to a monocyclic or polycyclic group that contains (e.g., consists of) 5 to 60 carbon atoms and contains only carbon as a cyclic atom. The term "C5-C" is also used herein. 60 "Carbocyclic group" refers to either an aromatic carbocyclic group or a non-aromatic carbocyclic group. C5-C 60 The carbocyclic group can be a ring (e.g., benzene), a monovalent group (e.g., a phenyl group), or a divalent group (e.g., a phenylene group). In one or more embodiments, depending on the linkage to C5-C... 60 The number of substituents in the carbocyclic group, C5-C 60 The carbocyclic group can be trivalent or tetravalent. In some embodiments, C5-C 60 The carbocyclic group can be C5-C 30 Carbocyclic groups, C5-C 24 Carbocyclic groups or C5-C 18 Carbon ring group.

[0481] As used in this article, the term "C1-C" 60 "Heterocyclic group" refers to a group that has a cyclic structure similar to C5-C6. 60 A group with a substantially similar structure to a carbocyclic group, but in addition to carbon (the number of carbon atoms can be 1 to 60, for example 1 to 30 or 1 to 24 carbon atoms), it uses at least one heteroatom selected from N, O, Si, P and S (for example 1 to 5 or 1 to 3 heteroatoms, for example 1, 2, 3, 4 or 5 heteroatoms) as the cyclic atom.

[0482] Replacement C5-C 60 Carbocyclic groups, substituted C1-C 60 Heterocyclic groups, substituted C1-C 60 Alkyl groups, substituted C2-C 60 alkenyl groups, substituted C2-C 60 alkynyl group, substituted C1-C 60 alkoxy groups, substituted C3-C 10 Cycloalkyl groups, substituted C1-C 10 Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkenyl groups, substituted C1-C 10 Heterocyclic alkenyl groups, substituted C6-C 60 aryl group, substituted C7-C 60 Aryl groups, substituted C6-C 60 aryloxy groups, substituted C6-C 60 aryl thiols, substituted C1-C 60heteroaryl groups, substituted C2-C 60 Heteroaryl groups, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 At least one of the substituents of the heteroaryl thio group, the substituted monovalent nonaromatic fused polycyclic group, and the substituted monovalent nonaromatic fused heterocyclic group may be selected from:

[0483] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl groups and C1-C 60 Alkoxy group;

[0484] Each is independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiol groups, C1-C 60 heteroaryl groups, C1-C 60 heteroaryloxy groups, C1-C 60 Heteroaryl thioyl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 ) and -P(=O)(Q 11 (Q) 12 At least one substituted C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl groups and C1-C 60 Alkoxy group;

[0485] C3-C 10 Cycloalkyl groups, C1-C10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiol groups, C1-C 60 heteroaryl groups, C1-C 60 heteroaryloxy groups, C1-C 60 Heteroaryl thio groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups;

[0486] Each is independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiol groups, C1-C 60 heteroaryl groups, C1-C 60 heteroaryloxy groups, C1-C 60 Heteroaryl thioyl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) and -P(=O)(Q 21 (Q) 22 At least one substituted C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C60 aryloxy group, C6-C 60 aryl thiol groups, C1-C 60 heteroaryl groups, C1-C 60 heteroaryloxy groups, C1-C 60 Heteroaryl thio groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups; and

[0487] -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 ),

[0488] Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 Aryl group, C1-C 60 heteroaryl groups, C1-C 60 Heteroaryloxy group, C1-C 60 A heteroaryl thioyl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heterocyclic group, a C1-C group substituted with at least one of deuterium, -F and cyano groups. 60 The alkyl group is a C6-C group substituted with at least one of a deuterium, -F, or cyano group. 60 Aryl groups, biphenyl groups, and terphenyl groups.

[0489] As used herein, the term "Ph" refers to a phenyl group, "Me" refers to a methyl group, "Et" refers to an ethyl group, and "t-Bu" or "Bu" refers to a t-Bu group. t "" refers to the tert-butyl group, and as used herein, the term "OMe" refers to the methyl methacrylate group.

[0490] As used in this article, the term "biphenyl group" refers to a "phenyl group substituted with a phenyl group." In other words, a "biphenyl group" is a group with a C6-C ratio. 60 The aryl group is a substituted phenyl group.

[0491] As used in this article, the term "terphenyl group" refers to a "phenyl group substituted with a biphenyl group." In other words, a "terphenyl group" is a phenyl group with a C6-C substituted group. 60 C6-C substituted with aryl group 60 The aryl group is a substituted phenyl group.

[0492] Unless otherwise defined, as used herein, * and *' each refer to the binding site with the adjacent atom in the corresponding formula.

[0493] The compounds according to the embodiments and the organic light-emitting devices according to the embodiments will be described in more detail below with reference to synthesis examples and embodiments. The phrase "using B instead of A" used to describe the synthesis examples means using an equimolar amount of B instead of A.

[0494] [Example]

[0495]

[0496] Synthesis Example 1: Synthesis of Compound 2

[0497]

[0498] (1) Synthesis of intermediate 2-1

[0499] 4-Bromo-9H-carbazole (1 equivalent), aniline (3 equivalents), tris(dibenzylacetone)dipalladium (0) (0.05 equivalents), tri-tert-butylphosphine (0.1 equivalents), and sodium tert-butoxide (3 equivalents) were dissolved in toluene and stirred at 100°C for 12 hours under a nitrogen atmosphere. After cooling, the organic layer was extracted three times with ethyl acetate and water, dried over anhydrous magnesium sulfate, and dried under reduced pressure. The obtained solid was purified by column chromatography to obtain intermediate 2-1 (yield: 75%).

[0500] (2) Synthesis of intermediate 2-2

[0501] Intermediate 2-1 (1 equivalent), 1,3-dibromo-5-fluorobenzene (1.5 equivalent), and K3PO4 (2 equivalent) were dissolved in DMF and then stirred at 160 °C for 12 hours. After cooling, the solvent was removed under reduced pressure, and the organic layer obtained by extraction three times with dichloromethane and water was dried over anhydrous magnesium sulfate and then under reduced pressure. The obtained solid was purified by column chromatography to obtain intermediate 2-2. (Yield: 65%)

[0502] (3) Synthesis of intermediate 2-3

[0503] Intermediate 2-2 (1 equivalent), diphenylamine (3 equivalents), tris(dibenzylacetone)dipalladium (0) (0.1 equivalents), tri-tert-butylphosphine (0.2 equivalents), and sodium tert-butoxide (4 equivalents) were dissolved in toluene and stirred at 100°C for 12 hours under a nitrogen atmosphere. After cooling, the organic layer was extracted three times with ethyl acetate and water, dried over anhydrous magnesium sulfate, and dried under reduced pressure. The obtained solid was purified by column chromatography to obtain intermediate 2-3. (Yield: 61%)

[0504] (4) Synthesis of intermediate 2-4

[0505] Intermediate 2-3 (1 equivalent), 3-bromo-5-phenoxy-N,N-diphenylaniline (1 equivalent), tris(dibenzylacetone)dipalladium (0) (0.05 equivalent), tri-tert-butylphosphine (0.1 equivalent), and sodium tert-butoxide (3 equivalent) were dissolved in toluene and stirred at 100°C for 12 hours under a nitrogen atmosphere. After cooling, the organic layer was extracted three times with ethyl acetate and water, dried over anhydrous magnesium sulfate, and dried under reduced pressure. The obtained solid was purified by column chromatography to obtain intermediate 2-4. (Yield: 55%)

[0506] (5) Synthesis of Compound 2

[0507] Intermediate 2-4 (1 equivalent) was dissolved in o-dichlorobenzene, and the flask was then cooled at 0°C under a nitrogen atmosphere. BBr3 (4 equivalents) was then slowly added. After the addition was complete, the temperature was raised to 150°C, and the resulting solution was stirred for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask until heating ceased to complete the reaction. Hexane was added to induce precipitation, and the resulting solid was obtained by filtration. The obtained solid was purified by silica gel filtration and then recrystallized from dichloromethane / hexane to obtain compound 2. (Yield: 25%)

[0508] Synthesis Example 2: Synthesis of Compound 3

[0509]

[0510] (1) Synthesis of intermediate 3-1

[0511] Intermediate 3-1 was obtained using 4-bromo-9H-carbazole (1 equivalent) and 5-fluoro-N1,N1,N3,N3-tetraphenylphenyl-1,3-diamine (1.5 equivalent) in essentially the same manner as that used to prepare intermediate 2-2. (Yield: 52%)

[0512] (2) Synthesis of intermediate 3-2

[0513] Intermediate 3-1 (1 equivalent), 3,5-bis(diphenylamino)phenol (1 equivalent), CuI (0.1 equivalent), 1,10-phenanthroline (0.1 equivalent), and K3PO4 (4 equivalent) were dissolved in DMF and then stirred at 165 °C for 36 hours. After cooling, the solvent was removed under reduced pressure, and the organic layer obtained by extraction three times with dichloromethane and water was dried over anhydrous magnesium sulfate and then under reduced pressure. The product was purified by column chromatography to obtain intermediate 3-2. (Yield: 45%)

[0514] (3) Synthesis of compound 3

[0515] Compound 3 was obtained using intermediate 3-2 in essentially the same manner as that used to prepare compound 2. (Yield: 29%)

[0516] Synthesis Example 3: Synthesis of Compound 4

[0517]

[0518] (1) Synthesis of intermediate 4-1

[0519] Intermediate 4-1 was obtained using intermediate 2-1 (1 equivalent) and 1-bromo-3-fluoro-5-phenoxybenzene (1.1 equivalent) in essentially the same manner as that used to prepare intermediate 2-2. (Yield: 66%)

[0520] (2) Synthesis of intermediate 4-2

[0521] Intermediate 4-2 was obtained using intermediate 4-1 (1 equivalent) and diphenylamine (2 equivalents) in essentially the same manner as that used to prepare intermediate 2-3. (Yield: 87%)

[0522] (3) Synthesis of intermediate 4-3

[0523] Intermediate 4-3 was synthesized using intermediate 4-2 and 5-chloro-N1,N1,N3,N3-tetraphenylphenyl-1,3-diamine in essentially the same manner as that used to prepare intermediate 2-4. (Yield: 69%)

[0524] (4) Synthesis of compound 4

[0525] Compound 4 was obtained using intermediate 4-3 in essentially the same manner as that used to prepare compound 2. (Yield: 27%)

[0526] Synthesis Example 4: Synthesis of Compound 6

[0527]

[0528] (1) Synthesis of intermediate 6-1

[0529] Intermediate 6-1 was obtained using 4-bromo-9H-carbazole (1 equivalent) and 3-bromo-5-phenoxy-N,N-diphenylaniline (1.5 equivalent) in essentially the same manner as that used to prepare intermediates 2-4. (Yield: 52%)

[0530] (2) Synthesis of intermediate 6-2

[0531] Intermediate 6-2 was synthesized using intermediate 6-1 (1 equivalent) and 3,5-bis(diphenylamino)phenol (1.1 equivalent) in essentially the same manner as that used to prepare intermediate 3-2. (Yield: 42%)

[0532] (3) Synthesis of compound 6

[0533] Compound 6 was obtained using intermediate 6-2 in essentially the same manner as that used to prepare compound 2. (Yield: 23%)

[0534] Synthesis Example 5: Synthesis of Compound 7

[0535]

[0536] (1) Synthesis of intermediate 7-1

[0537] Intermediate 7-1 was obtained using intermediate 4-2 (1 equivalent) and 3-bromo-5-phenoxy-N,N-diphenylaniline (1 equivalent) in essentially the same manner as that used to prepare intermediate 2-4. (Yield: 50%)

[0538] (2) Synthesis of compound 7

[0539] Compound 7 was obtained using intermediate 7-1 in essentially the same manner as that used to prepare compound 2. (Yield: 18%)

[0540] Synthesis Example 6: Synthesis of Compound 15

[0541]

[0542] (1) Synthesis of intermediate 15-1

[0543] Intermediate 15-1 was obtained in essentially the same manner as that used to prepare intermediate 6-1, but with 3-bromo-N,N-diphenyl-5-(phenylthio)aniline (1.5 equivalents) instead of 3-bromo-5-phenoxy-N,N-diphenylaniline. (Yield: 46%)

[0544] (2) Synthesis of intermediate 15-2

[0545] Intermediate 15-2 was obtained using intermediate 15-1 (1 equivalent) and 3-(diphenylamino)-5-(phenylthio)benzylthiophenol (1 equivalent) in essentially the same manner as that used to prepare intermediate 6-2. (Yield: 57%)

[0546] (3) Synthesis of compound 15

[0547] Compound 15 was obtained using intermediate 15-2 in essentially the same manner as that used to prepare compound 2. (Yield: 8%)

[0548] Synthesis Example 7: Synthesis of Compound 28

[0549]

[0550] (1) Synthesis of intermediate 28-1

[0551] Intermediate 28-1 was synthesized in essentially the same manner as that used to prepare intermediate 4-2, but with 1,2,3,4-tetrahydroquinoline used instead of diphenylamine. (Yield: 80%)

[0552] (2) Synthesis of intermediate 28-2

[0553] Intermediate 28-2 was synthesized using intermediate 28-1 and 1-(3-bromo-5-phenoxyphenyl)-1,2,3,4-tetrahydroquinoline in essentially the same manner as that used to prepare intermediate 2-4. (Yield: 83%)

[0554] (3) Synthesis of compound 28

[0555] Compound 28 was obtained using intermediate 28-2 in essentially the same manner as that used to prepare compound 2. (Yield: 33%)

[0556] Synthesis Example 8: Synthesis of Compound 51

[0557]

[0558] (1) Synthesis of intermediate 51-1

[0559] Intermediate 51-1 was synthesized using intermediates 4-2 and 3-bromo-N,N-diphenyl-5-(phenylthio)aniline in essentially the same manner as that used to prepare intermediate 2-4. (Yield: 73%)

[0560] (2) Synthesis of compound 51

[0561] Compound 51 was obtained using intermediate 51-1 in essentially the same manner as that used to prepare compound 2. (Yield: 13%)

[0562] The compounds synthesized in Synthetic Examples 1 to 8 1 The 1H NMR and molecular weight data are shown in Table 1:

[0563] [Table 1]

[0564]

[0565] Example 1

[0566] As the anode, Corning 15Ω / cm 2 The ITO / glass substrate was cut to a size of 50mm × 50mm × 0.7mm, ultrasonically treated with isopropanol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes. The ITO glass substrate was then fed into a vacuum deposition apparatus.

[0567] NPD is vacuum deposited on a glass substrate to form a structure with... A hole injection layer of a certain thickness is formed, and TCTA is vacuum-deposited on it to form a layer with [missing information]. A first hole transport layer of thickness. CzSi is vacuum-deposited onto the first hole transport layer to form a layer with... The second hole transport layer has a thickness of [missing information].

[0568] mCP (host) and compound 2 (dopant) were co-deposited on the second hole transport layer at a weight ratio of 99:1 to form a layer with... The thickness of the emission layer.

[0569] TSPO1 was vacuum deposited onto the emitter layer to form a structure with... A first electron transport layer of a certain thickness is formed, and TPBI is vacuum deposited on the first electron transport layer to form a layer with... A second electron transport layer of thickness is formed. LiF is vacuum deposited on the second electron transport layer to form a layer with... An electron-injected layer of a certain thickness is formed, and Al is vacuum-deposited on it to form a layer with [missing information]. A cathode electrode of a certain thickness is used to complete the fabrication of the organic light-emitting device.

[0570] Examples 2 to 8 and Comparative Examples 1 to 3

[0571] The organic light-emitting device was fabricated in essentially the same manner as in Example 1, but the corresponding compounds shown in Table 2 were used instead of compound 2 as dopants in the formation of the emission layer.

[0572] Evaluation Example 1

[0573] The driving voltage, current efficiency, external quantum luminescence efficiency, and emission color of the organic light-emitting devices manufactured according to Examples 1 to 8 and Comparative Examples 1 to 3 were measured using a Keithley SMU 236 and a luminance meter PR650, and the results are shown in Table 2:

[0574] [Table 2]

[0575]

[0576]

[0577]

[0578] As can be seen from Table 2, the organic light-emitting devices of Examples 1 to 8 emit blue light with a maximum emission wavelength of about 430 nm to about 480 nm, and, for example, have lower driving voltage, higher current efficiency and higher external quantum light-emitting efficiency compared with the organic light-emitting devices of Comparative Examples 1 to 3.

[0579] Organic light-emitting devices containing this heterocyclic compound can have improved efficiency and / or lifespan characteristics.

[0580] As used herein, the terms “substantially,” “about,” and similar terms are used as terms of approximation rather than as terms of degree, and are intended to explain the inherent biases in measurements or calculations that would be recognized by one of ordinary skill in the art.

[0581] Any numerical ranges listed herein are intended to include all subranges of the same numerical precision falling within the listed range. For example, the range “1.0 to 10.0” is intended to include all subranges between the listed minimum value of 1.0 and the listed maximum value of 10.0 (and inclusive), i.e., a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit listed herein is intended to include all lower numerical limits falling within it, and any minimum numerical limit listed in this specification is intended to include all higher numerical limits falling within it. Therefore, the applicant reserves the right to amend this specification (including the claims) to expressly list any subranges falling within the scope expressly listed herein.

[0582] It should be understood that the embodiments described herein are for descriptive purposes only and not for limiting purposes. The description of features or aspects in each embodiment should generally be considered as other similar features or aspects applicable to other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, those skilled in the art will understand that various changes in form and detail may be made herein without departing from the spirit and scope defined by the claims and their equivalents.

Claims

1. An organic light-emitting device, comprising: First electrode; The second electrode; and an organic layer including an emission layer and located between the first electrode and the second electrode; and At least one heterocyclic compound represented by Formula 1, The first electrode comprises ITO, IZO, SnO2, ZnO, Mg, Ag, Al, Al-Li, Ca, Mg-In, Mg-Ag, or any combination thereof, and The second electrode comprises Li, Ag, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, ITO, IZO, or any combination thereof: <Formula 1> , In Equation 1, X 11 is NR 15 , O, S or Se, A 11 is a group represented by formula 10A, Y 11 to Y 13 each is a carbon atom in a group represented by formula 10A, A 12 to A 14 each independently is a phenyl group, b12 and b14 are each independently selected from 1, 2, 3, and 4, while b13 is selected from 1, 2, and 3. <Form 10A> , In Equation 10A, X 111 is NR 114 , O, S or Se, X 112 is NR 115 , O, S or Se, A 111 and A 112 each independently is a phenyl group, Y 11 to Y 13 each is a carbon atom in Formula 1, R 12 , R 14 , R 112 , and R 113 are each independently selected from the group consisting of hydrogen, deuterium, C1-C 10 alkyl groups, and C1-C 10 alkoxy groups; R 15 , R 114 , and R 115 are each independently selected from the group consisting of C6-C 20 aryl groups; and each independently substituted with at least one substituent selected from the group consisting of deuterium and C1-C4alkyl; 10 C6-C10aryl group; each independently substituted with at least one substituent selected from the group consisting of deuterium and C1-C4alkyl; 20 C6-C10aryl group; each independently substituted with at least one substituent selected from the group consisting b111 is selected from 1, 2, and 3; b112 is selected from 1, 2, 3, and 4; and R 13 and R 111 is selected from the group represented by one of Formula 3-1 to Formula 3-3: In Equation 3-1, R 31 and R 32 are each independently selected from phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups; In equations 3-2 and 3-3, A 31 is a phenyl group, R 31 to R 37 each independently is selected from the group consisting of hydrogen, deuterium, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, a methoxy group, an ethoxy group, an n-propyloxy group, an i-propyloxy group, an n-butyloxy group, an s-butyloxy group, an i-butyloxy group, and a t-butyloxy group, b31 is selected from 1, 2, 3, and 4, and represents a binding site to an adjacent atom.

2. The organic light-emitting device as claimed in claim 1, wherein: The first electrode is the anode. The second electrode is the cathode. The organic layer includes a hole transport region between the first electrode and the emitter layer and / or an electron transport region between the emitter layer and the second electrode. The hole transport region includes a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof, and The electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

3. The organic light-emitting device of claim 1, wherein the emitting layer comprises the heterocyclic compound.

4. The organic light-emitting device of claim 1, wherein the emitting layer comprises the heterocyclic compound and the host, and The heterocyclic compound includes a thermally activated delayed fluorescent emitter.

5. The organic light-emitting device of claim 4, wherein the heterocyclic compound is in an amount of 0.01 parts by weight to 30 parts by weight, based on 100 parts by weight of the main body.

6. Equipment, including: A thin-film transistor, the thin-film transistor comprising a source electrode, a drain electrode, and an active layer; And the organic light-emitting device according to claim 1, The first electrode of the organic light-emitting device is electrically connected to one of the source electrode and the drain electrode of the thin-film transistor.

7. Heterocyclic compounds represented by Formula 1: <Formula 1> ， wherein In Equation 1, X 11 is NR 15 , O, S or Se, A 11 is a group represented by formula 10A, Y 11 to Y 13 each is a carbon atom in a group represented by formula 10A, A 12 to A 14 each independently a phenyl group, b12 and b14 are each independently selected from 1, 2, 3, and 4, while b13 is selected from 1, 2, and 3. <Form 10A> ， In Equation 10A, X 111 is NR 114 , O, S or Se, X 112 is NR 115 , O, S or Se, A 111 and A 112 each independently is a phenyl group, Y 11 to Y 13 each is a carbon atom in Formula 1, R 12 , R 14 , R 112 , and R 113 are each independently selected from the group consisting of hydrogen, deuterium, C1-C 10 alkyl groups, and C1-C 10 alkoxy groups; R 15 , R 114 , and R 115 are each independently selected from the group consisting of C6-C 20 aryl groups; and each independently substituted with at least one substituent selected from the group consisting of deuterium and C1-C4alkyl; 10 C6-C10aryl group; each independently substituted with at least one substituent selected from the group consisting of deuterium and C1-C4alkyl; 20 C6-C10aryl group; each independently substituted with at least one substituent selected from the group consisting b111 is selected from 1, 2, and 3; b112 is selected from 1, 2, 3, and 4; and R 13 and R 111 is selected from the group represented by one of Formula 3-1 to Formula 3-3: In Equation 3-1, R 31 and R 32 are each independently selected from phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups; In equations 3-2 and 3-3, A 31 is a phenyl group, R 31 to R 37 each independently is selected from the group consisting of hydrogen, deuterium, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, a methoxy group, an ethoxy group, an n-propyloxy group, an i-propyloxy group, an n-butyloxy group, an s-butyloxy group, an i-butyloxy group, and a t-butyloxy group, b31 is selected from 1, 2, 3, and 4, and represents a binding site to an adjacent atom.

8. The heterocyclic compound of claim 7, wherein R 15 , R 114 , and R 115 are each independently selected from the group consisting of: Phenyl group, biphenyl group, triphenyl group and naphthyl group; and Each of the following groups is independently selected from at least one substituted phenyl group, biphenyl group, terphenyl group, and naphthyl group selected from deuterium, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, and tert-butyl group.

9. The heterocyclic compound of claim 7, wherein R 12 , R 14 , R 112 , and R 113 are each independently selected from the group consisting of: hydrogen, deuterium, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a sec-butyl group, an i-butyl group, a t-butyl group, a methoxy group, an ethoxy group, an n-propyloxy group, an i-propyloxy group, an n-butyloxy group, a sec-butyloxy group, an i-butyloxy group, and a t-butyloxy group.

10. The heterocyclic compound according to claim 7, wherein the heterocyclic compound represented by Formula 1 is represented by Formula 1-21: <Formula 1-21> ， wherein In Formula 1-21, X 11 , X 111 and X 112 each independently is the same as described for Formula 1 and Formula 10A, R 12b and R 14a each independently is the same as described for R 12 in Formula 1, R 112d R 112 the same as described above in connection with R 112 in formula 10A, and R 13b and R 111b are the same as described for R 13 and R 111 respectively.

11. The heterocyclic compound according to claim 7, wherein the heterocyclic compound represented by Formula 1 is selected from the group I compounds: <group I> 。

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